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Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

$2,975,000

4 Beds ⋅ 4 Baths

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

23961 Lynnewood Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$2,500,000

205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images in photos). The beautiful front lawn provides a park-like setting with one-of-a-kind water-views overlooking St. Michaels Harbor. There is also a 2 bedroom, 2 bath guest cottage on the property. The property directly across the street (FKA The Hambeleton Inn) was purchased as a private residence and serves as a second home to its owner. This is a wonderful opportunity to own a landmark historic inn or primary or second home in the heart of St. Michaels.

5 Beds ⋅ 9 Baths

205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images in photos). The beautiful front lawn provides a park-like setting with one-of-a-kind water-views overlooking St. Michaels Harbor. There is also a 2 bedroom, 2 bath guest cottage on the property. The property directly across the street (FKA The Hambeleton Inn) was purchased as a private residence and serves as a second home to its owner. This is a wonderful opportunity to own a landmark historic inn or primary or second home in the heart of St. Michaels.

205 Cherry St, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Coldwell Banker Realty.

$2,450,000

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

4 Beds ⋅ 5 Baths

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

965 San Domingo, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS..... A treasure of vantage points and chic contemporary beauty, this Martingham waterfront retreat offers rare front-row views of Miles River happenings - including the historic Log Canoe Races, Fourth of July fireworks, daily passages of billowing sails,and, on crisp days, sightlines stretching for miles. Set on 2.32 acres with nearly 250 feet of sandy shoreline, life here moves with effortless rhythm; from morning beachfront strolls to afternoons shaped by regattas, summer pool partiesand in-town finds. Relax by the awe inspiring extra large 50 foot heated pool with jacuzzi with of space for sunbathing and relaxing. There is also a IGLUCRAFT sauna from Eastonia for the health concious resident. Within your home of contemporary coastal personality, 2,875 square feet are serene and elevated as walls of airy hues allow gridless-windows to compose ever-changing artwork of golden sunsets, lifting fog, and distant gliding hulls. Built-ins display collected shells and photographs from travels, while a glowing hearth anchors conversation with holiday guests. Spend unhurried Sundays in the landscaped-wrapped screened-in porch. Here, dream-up recipes for the weekend’s gatherings, while the kitchen’s updated stone surfaces and appliances prepare everything from perfect picnics to generous crab feasts. At day’s end, two and a half modern baths soothe, partnering with a main-level primary suite and two additional bedrooms—including airy loft. serving as a 4th bedroom. From your 125-foot pier with 8–10 feet MLW, welcome the seasonal residents that live on the Osprey platform, launch kayaks toward the picturesque edges of Long Haul Creek or set sail into the open reaches of the Chesapeake Bay. While on tour, spot sea glass along the shore, linger at the pier, and imagine the ease of your two-car garage. The dock - built by WHEEMS - offers 2 jet ski lifts, a 16K pound boatlift, electric and water and a platform area to sit over the water and relax . From home, St. Michaels charms just minutes away, where beloved shops, dining, and harbor life fill easy afternoons, while rounds at The Links at Perry Cabin, cycling routes, and scenic trails shape the days between. The roof has been replaced by MARASUN in 2022, new HVAC in 2021, pool build in 2022, new water heater 2023.

24830 Deepwater Point Dr, Saint Michaels

$2,435,000

DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS..... A treasure of vantage points and chic contemporary beauty, this Martingham waterfront retreat offers rare front-row views of Miles River happenings - including the historic Log Canoe Races, Fourth of July fireworks, daily passages of billowing sails,and, on crisp days, sightlines stretching for miles. Set on 2.32 acres with nearly 250 feet of sandy shoreline, life here moves with effortless rhythm; from morning beachfront strolls to afternoons shaped by regattas, summer pool partiesand in-town finds. Relax by the awe inspiring extra large 50 foot heated pool with jacuzzi with of space for sunbathing and relaxing. There is also a IGLUCRAFT sauna from Eastonia for the health concious resident. Within your home of contemporary coastal personality, 2,875 square feet are serene and elevated as walls of airy hues allow gridless-windows to compose ever-changing artwork of golden sunsets, lifting fog, and distant gliding hulls. Built-ins display collected shells and photographs from travels, while a glowing hearth anchors conversation with holiday guests. Spend unhurried Sundays in the landscaped-wrapped screened-in porch. Here, dream-up recipes for the weekend’s gatherings, while the kitchen’s updated stone surfaces and appliances prepare everything from perfect picnics to generous crab feasts. At day’s end, two and a half modern baths soothe, partnering with a main-level primary suite and two additional bedrooms—including airy loft. serving as a 4th bedroom. From your 125-foot pier with 8–10 feet MLW, welcome the seasonal residents that live on the Osprey platform, launch kayaks toward the picturesque edges of Long Haul Creek or set sail into the open reaches of the Chesapeake Bay. While on tour, spot sea glass along the shore, linger at the pier, and imagine the ease of your two-car garage. The dock - built by WHEEMS - offers 2 jet ski lifts, a 16K pound boatlift, electric and water and a platform area to sit over the water and relax . From home, St. Michaels charms just minutes away, where beloved shops, dining, and harbor life fill easy afternoons, while rounds at The Links at Perry Cabin, cycling routes, and scenic trails shape the days between. The roof has been replaced by MARASUN in 2022, new HVAC in 2021, pool build in 2022, new water heater 2023.

24830 Deepwater Point Dr, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home’s appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.

$2,200,000

4 Beds ⋅ 5 Baths

This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home’s appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.

962 San Domingo Ct, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for entertaining. Gleaming hardwood floors enhance the home's inviting ambiance. The primary suite is a serene escape with a stunning bath, while the upper level offers generous space ready to be transformed to match your vision. Outside, the property unfolds into a private waterfront playground, complete with a charming cottage ideal for guests or extended family, and a detached two-car garage with a one-bedroom apartment awaiting restoration. Bring your imagination! An exceptional opportunity for boating, entertaining, and relaxed coastal living. Just minutes from fabulous restaurants, boutique shopping, and the quaint charm of St. Michaels.

$2,200,000

4 Beds ⋅ 5 Baths

Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for entertaining. Gleaming hardwood floors enhance the home's inviting ambiance. The primary suite is a serene escape with a stunning bath, while the upper level offers generous space ready to be transformed to match your vision. Outside, the property unfolds into a private waterfront playground, complete with a charming cottage ideal for guests or extended family, and a detached two-car garage with a one-bedroom apartment awaiting restoration. Bring your imagination! An exceptional opportunity for boating, entertaining, and relaxed coastal living. Just minutes from fabulous restaurants, boutique shopping, and the quaint charm of St. Michaels.

24645 Long Haul, Saint Michaels

Listing courtesy of Coldwell Banker Realty. Contact:

Significant Price Improvement!!! Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully re-imagined through comprehensive renovations completed in 2023 and 2024. See virtual tours above. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms and 5 and a half baths, this home offers an elevated blend of sophistication, comfort, and timeless Eastern Shore charm— located on East Chew Street, the property is walking distance to the harbor, boutiques, and celebrated dining of St. Michaels. From the moment you enter, the quality is unmistakable. Clean sightlines and an open, interconnected floor plan create an ideal setting for both everyday living and effortless entertaining. Throughout the home, curated lighting, custom millwork, elegant crown molding, custom doors, and redesigned fireplaces reflect a commitment to thoughtful design and enduring craftsmanship. The main level features a primary suite with beautifully updated finishes and refined details, including a fully renovated primary bath. There is a second primary suite on the second level as well with a renovated bath. The main residence offers four en-suite bedrooms; all baths have been renovated each providing privacy and comfort for family and guests alike. A standout feature of the property is the fully independent renovated permitted apartment above the two-car heated garage. Complete with a full kitchen, bath, washer and dryer, office area, and sleeping loft, this versatile space is ideal for extended family, guests, a private studio, home office or potential rental income. At the heart of the home, with secure access to the main house from a two garage, providing off street parking and easy kitchen access, is both functional and thoughtful. The kitchen showcases high-end appliances with gas, exquisite finishes, and custom lighting. The kitchen flows seamlessly into the living and dining areas, where fireplaces add warmth and ambiance. Upstairs, an additional media lounge area, a second upper-level primary suite offers a serene retreat with updated bathroom cabinetry and fixtures, a fireplace, and a beautifully designed custom walk-in closet. A third en-suite bedroom along with a spacious laundry room adjacent to the media room, enhance convenience. The fourth en-suite bedroom is on the third level with additional living space and a renovated bathroom. Outside, professionally newly designed landscaping and a full irrigation system provide year-round beauty, while the blue slate terrace—framed by expertly trained David Austin climbing roses—a grilling area creates a private outdoor sanctuary for entertaining or quiet reflection. Modern conveniences include Wi-Fi broadband, advanced home monitoring systems, and a Hikvision doorbell with remote access, updated HVAC, Renaldi tankless hot water systems both add comfort and peace of mind. A concrete crawlspace with a dehumidification unit is part of this well-built home. Perfectly positioned near the waterfront and within easy reach of Easton and Oxford, this turnkey home is ideal as a full-time residence or a sophisticated weekend retreat. With flawless finishes, flexible living spaces, and an unrivaled location, this property represents the pinnacle of Eastern Shore living. Schedule your private showing and experience its exceptional character firsthand. On a price per sq. ft. basis this property represents an excellent value and the new two-level apartment above the heated garage is an exceptional rental investment opportunity, guest quarters, studio or office.

$2,125,000

5 Beds ⋅ 6 Baths

Significant Price Improvement!!! Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully re-imagined through comprehensive renovations completed in 2023 and 2024. See virtual tours above. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms and 5 and a half baths, this home offers an elevated blend of sophistication, comfort, and timeless Eastern Shore charm— located on East Chew Street, the property is walking distance to the harbor, boutiques, and celebrated dining of St. Michaels. From the moment you enter, the quality is unmistakable. Clean sightlines and an open, interconnected floor plan create an ideal setting for both everyday living and effortless entertaining. Throughout the home, curated lighting, custom millwork, elegant crown molding, custom doors, and redesigned fireplaces reflect a commitment to thoughtful design and enduring craftsmanship. The main level features a primary suite with beautifully updated finishes and refined details, including a fully renovated primary bath. There is a second primary suite on the second level as well with a renovated bath. The main residence offers four en-suite bedrooms; all baths have been renovated each providing privacy and comfort for family and guests alike. A standout feature of the property is the fully independent renovated permitted apartment above the two-car heated garage. Complete with a full kitchen, bath, washer and dryer, office area, and sleeping loft, this versatile space is ideal for extended family, guests, a private studio, home office or potential rental income. At the heart of the home, with secure access to the main house from a two garage, providing off street parking and easy kitchen access, is both functional and thoughtful. The kitchen showcases high-end appliances with gas, exquisite finishes, and custom lighting. The kitchen flows seamlessly into the living and dining areas, where fireplaces add warmth and ambiance. Upstairs, an additional media lounge area, a second upper-level primary suite offers a serene retreat with updated bathroom cabinetry and fixtures, a fireplace, and a beautifully designed custom walk-in closet. A third en-suite bedroom along with a spacious laundry room adjacent to the media room, enhance convenience. The fourth en-suite bedroom is on the third level with additional living space and a renovated bathroom. Outside, professionally newly designed landscaping and a full irrigation system provide year-round beauty, while the blue slate terrace—framed by expertly trained David Austin climbing roses—a grilling area creates a private outdoor sanctuary for entertaining or quiet reflection. Modern conveniences include Wi-Fi broadband, advanced home monitoring systems, and a Hikvision doorbell with remote access, updated HVAC, Renaldi tankless hot water systems both add comfort and peace of mind. A concrete crawlspace with a dehumidification unit is part of this well-built home. Perfectly positioned near the waterfront and within easy reach of Easton and Oxford, this turnkey home is ideal as a full-time residence or a sophisticated weekend retreat. With flawless finishes, flexible living spaces, and an unrivaled location, this property represents the pinnacle of Eastern Shore living. Schedule your private showing and experience its exceptional character firsthand. On a price per sq. ft. basis this property represents an excellent value and the new two-level apartment above the heated garage is an exceptional rental investment opportunity, guest quarters, studio or office.

203 Chew Ave E, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Monument Sotheby's International Realty.

$2,100,000

Nestled on a gorgeous waterfront lot just minutes from St. Michaels, this exceptional property offers the perfect blend of privacy, comfort, and convenience. Enjoy an easy bike ride into town while coming home to a peaceful setting surrounded by mature, established trees and beautifully landscaped grounds. Built with quality and designed for comfortable living, the home features two spacious primary suites, including one conveniently located on the first floor. Large walk-in closets provide abundant storage throughout. An attached in-law suite offers flexibility for extended family, guests, or multi-generational living. The impressive foyer welcomes you into a thoughtfully designed floor plan featuring mostly hardwood floors throughout. Enjoy a spacious dining room perfect for large family gatherings, a comfortable living room anchored by a cozy brick fireplace, dedicated office space, and a separate craft room. A large utility room provides exceptional functionality with space for an extra freezer and refrigerator, while multiple HVAC zones ensure comfortable heating and cooling throughout the home. Outdoor amenities are equally impressive. Relax by the pool, entertain on the waterfront, or take advantage of the private dock with approximately 4 feet of mean low water depth. The property also includes a substantial workshop with tractor storage, ideal for hobbyists, boaters, or those needing extra workspace. Recent improvements provide peace of mind, including a roof that is just two years old and a paved driveway completed within the last year. This is a rare opportunity to own a solidly built waterfront retreat offering space, functionality, and timeless Eastern Shore charm just moments from the shops, restaurants, and waterfront attractions of St. Michaels.

5 Beds ⋅ 6 Baths

Nestled on a gorgeous waterfront lot just minutes from St. Michaels, this exceptional property offers the perfect blend of privacy, comfort, and convenience. Enjoy an easy bike ride into town while coming home to a peaceful setting surrounded by mature, established trees and beautifully landscaped grounds. Built with quality and designed for comfortable living, the home features two spacious primary suites, including one conveniently located on the first floor. Large walk-in closets provide abundant storage throughout. An attached in-law suite offers flexibility for extended family, guests, or multi-generational living. The impressive foyer welcomes you into a thoughtfully designed floor plan featuring mostly hardwood floors throughout. Enjoy a spacious dining room perfect for large family gatherings, a comfortable living room anchored by a cozy brick fireplace, dedicated office space, and a separate craft room. A large utility room provides exceptional functionality with space for an extra freezer and refrigerator, while multiple HVAC zones ensure comfortable heating and cooling throughout the home. Outdoor amenities are equally impressive. Relax by the pool, entertain on the waterfront, or take advantage of the private dock with approximately 4 feet of mean low water depth. The property also includes a substantial workshop with tractor storage, ideal for hobbyists, boaters, or those needing extra workspace. Recent improvements provide peace of mind, including a roof that is just two years old and a paved driveway completed within the last year. This is a rare opportunity to own a solidly built waterfront retreat offering space, functionality, and timeless Eastern Shore charm just moments from the shops, restaurants, and waterfront attractions of St. Michaels.

8240 Tricefield, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and cultural amenities—no car required. Designed for both comfort and entertaining, the light filled interior features an open floor plan with high ceilings, a well-appointed chef’s kitchen, and a welcoming fireplace. Four private bedroom suites – including a primary suite on the main level - make it a breeze to accommodate larger family gatherings and visiting friends. A spacious screened waterside porch, heated inground pool, deck and Bocce Court extend the living space to the outdoors for seasonal entertaining and warmer weather fun. A separate pool house/studio, connected by the screened porch and breezeway, includes a full bath and offers flexibility for use as a home office, creative space or additional guest quarters. The 2.3 acres lot is located at the edge of the San Domingo Cove community and is adjacent to protected woodlands, providing privacy, and offers with public water and sewer and a fully fenced backyard. Boating enthusiasts will appreciate the dock (shared with one neighboring property), offering two dedicated slips and a floating dock per owner and water depths of approximately 4–4.5 feet at the slips and 3 feet at the floating dock. From here it is easy to boat to Tilghman Island and Oxford, and San Domingo Creek is also great for kayaking and canoeing. An exceptional and rare opportunity to enjoy refined, in town waterfront living in one of Talbot County’s most sought after communities.

$2,000,000

4 Beds ⋅ 6 Baths

Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and cultural amenities—no car required. Designed for both comfort and entertaining, the light filled interior features an open floor plan with high ceilings, a well-appointed chef’s kitchen, and a welcoming fireplace. Four private bedroom suites – including a primary suite on the main level - make it a breeze to accommodate larger family gatherings and visiting friends. A spacious screened waterside porch, heated inground pool, deck and Bocce Court extend the living space to the outdoors for seasonal entertaining and warmer weather fun. A separate pool house/studio, connected by the screened porch and breezeway, includes a full bath and offers flexibility for use as a home office, creative space or additional guest quarters. The 2.3 acres lot is located at the edge of the San Domingo Cove community and is adjacent to protected woodlands, providing privacy, and offers with public water and sewer and a fully fenced backyard. Boating enthusiasts will appreciate the dock (shared with one neighboring property), offering two dedicated slips and a floating dock per owner and water depths of approximately 4–4.5 feet at the slips and 3 feet at the floating dock. From here it is easy to boat to Tilghman Island and Oxford, and San Domingo Creek is also great for kayaking and canoeing. An exceptional and rare opportunity to enjoy refined, in town waterfront living in one of Talbot County’s most sought after communities.

938 Marea Ter, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Washington Fine Properties, LLC.

$1,950,000

The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A What's special The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A long, pine-lined entrance drive carries you toward a first glimpse of Harris Creek ahead — water framed by tall pines, open and still. Then the drive sweeps gently to the left, and then, almost as a surprise, the cottage — modest, elegant, perfectly placed. It makes no attempt to impress. It doesn’t need to. The cottage is quiet and handsome — simply elegant in the way that only genuine character produces. Nothing oversized, nothing imposing. Just a well-proportioned, beautifully maintained home that belongs exactly where it sits. That first view of the house — unhurried, understated, perfectly at home in its setting — tells you everything about what kind of place this is. THE PROPERTY Few waterfront properties in Talbot County can offer what Rose’s Garden delivers: 6.87 private acres along Harris Creek, with approximately 400 feet of rip-rap shoreline in excellent condition. That kind of scale — within the Saint Michaels area — is simply not available anymore. And the west-facing orientation means sunsets over open water every evening, looking out across largely undeveloped land on the opposite shore. The views are clean, natural, and remarkably unspoiled. For a property this close to Saint Michaels, that is genuinely extraordinary. A private dock with 4 feet of water provides direct access to the creek and the Chesapeake Bay beyond. The home has been comprehensively renovated — new roof, refinished hardwood floors, updated kitchen, two fully remodeled baths, and complete HVAC throughout. A buyer arrives to something turnkey, not a project. THE LIFESTYLE Morning coffee on the primary bedroom deck with the creek glassy and still, nothing but natural shoreline across the water. Afternoons in the saltwater pool with the scent of pines and the sound of the water nearby. Evenings at the waterside pavilion as the sky turns orange over Harris Creek — unobstructed, undeveloped, all yours to take in. The rose garden and large, beautiful mature trees spread across the property give the grounds a park-like, tended quality that simply cannot be manufactured — it accumulates over decades, and here it already exists. At night, subtle landscape lighting illuminates those trees from below, casting the grounds in a quiet, warm glow. It is the kind of lighting that enhances rather than announces — a property that is just as inviting after dark as it is at sunset. And yet Saint Michaels — its restaurants, the Chesapeake Bay Maritime Museum, the Miles River Yacht Club — is just minutes away. The seclusion is real. The convenience is too. That combination is what makes Rose’s Garden so difficult to replicate. WHY THIS PROPERTY IS RARE Properties like Rose’s Garden do not come together by accident. The acreage, the frontage, the dock, the unspoiled views, the mature landscape — each of these alone would make a property noteworthy. Together, and this close to Saint Michaels, they represent something that simply does not come to market often. The renovation means a buyer inherits none of the headaches that typically accompany older waterfront homes — the deferred maintenance, the aging systems, the compromises. The work is done and done well. Rose’s Garden is ready for its next chapter. AT A GLANCE 6.87 private acres — Saint Michaels area — Waterside pavilion — Pine-lined entrance drive w/ creek views — New roof — Large mature trees throughout grounds — Primary bedroom deck w/ water views — Subtle up lighting on mature trees — Full HVAC — central + mini-splits — Unspoiled views — largely undeveloped opposite shore — Both baths fully remodeled — 400 ft Harris Creek frontage — Refinished hardwood floors — Rip-rap shoreline — excellent condition — Updated kitchen w/

The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A What's special The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A long, pine-lined entrance drive carries you toward a first glimpse of Harris Creek ahead — water framed by tall pines, open and still. Then the drive sweeps gently to the left, and then, almost as a surprise, the cottage — modest, elegant, perfectly placed. It makes no attempt to impress. It doesn’t need to. The cottage is quiet and handsome — simply elegant in the way that only genuine character produces. Nothing oversized, nothing imposing. Just a well-proportioned, beautifully maintained home that belongs exactly where it sits. That first view of the house — unhurried, understated, perfectly at home in its setting — tells you everything about what kind of place this is. THE PROPERTY Few waterfront properties in Talbot County can offer what Rose’s Garden delivers: 6.87 private acres along Harris Creek, with approximately 400 feet of rip-rap shoreline in excellent condition. That kind of scale — within the Saint Michaels area — is simply not available anymore. And the west-facing orientation means sunsets over open water every evening, looking out across largely undeveloped land on the opposite shore. The views are clean, natural, and remarkably unspoiled. For a property this close to Saint Michaels, that is genuinely extraordinary. A private dock with 4 feet of water provides direct access to the creek and the Chesapeake Bay beyond. The home has been comprehensively renovated — new roof, refinished hardwood floors, updated kitchen, two fully remodeled baths, and complete HVAC throughout. A buyer arrives to something turnkey, not a project. THE LIFESTYLE Morning coffee on the primary bedroom deck with the creek glassy and still, nothing but natural shoreline across the water. Afternoons in the saltwater pool with the scent of pines and the sound of the water nearby. Evenings at the waterside pavilion as the sky turns orange over Harris Creek — unobstructed, undeveloped, all yours to take in. The rose garden and large, beautiful mature trees spread across the property give the grounds a park-like, tended quality that simply cannot be manufactured — it accumulates over decades, and here it already exists. At night, subtle landscape lighting illuminates those trees from below, casting the grounds in a quiet, warm glow. It is the kind of lighting that enhances rather than announces — a property that is just as inviting after dark as it is at sunset. And yet Saint Michaels — its restaurants, the Chesapeake Bay Maritime Museum, the Miles River Yacht Club — is just minutes away. The seclusion is real. The convenience is too. That combination is what makes Rose’s Garden so difficult to replicate. WHY THIS PROPERTY IS RARE Properties like Rose’s Garden do not come together by accident. The acreage, the frontage, the dock, the unspoiled views, the mature landscape — each of these alone would make a property noteworthy. Together, and this close to Saint Michaels, they represent something that simply does not come to market often. The renovation means a buyer inherits none of the headaches that typically accompany older waterfront homes — the deferred maintenance, the aging systems, the compromises. The work is done and done well. Rose’s Garden is ready for its next chapter. AT A GLANCE 6.87 private acres — Saint Michaels area — Waterside pavilion — Pine-lined entrance drive w/ creek views — New roof — Large mature trees throughout grounds — Primary bedroom deck w/ water views — Subtle up lighting on mature trees — Full HVAC — central + mini-splits — Unspoiled views — largely undeveloped opposite shore — Both baths fully remodeled — 400 ft Harris Creek frontage — Refinished hardwood floors — Rip-rap shoreline — excellent condition — Updated kitchen w/

8670 Bozman Neavitt, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Nestled on 2.3 private acres in the sought-after Martingham neighborhood, this beautifully updated waterfront home offers one level living with the perfect blend of comfort, style, and outdoor living. Overlooking Porter Creek, the property features a private pier with lift and rip-rapped shoreline, where you can enjoy breathtaking sunsets, and endless days enjoying the water. Inside, the open floor plan flows effortlessly from the spacious living areas, open dining area, to the fully renovated kitchen, complete with quartz countertops, custom cabinetry, and modern appliances. The expansive waterside owner’s suite has a luxurious bathroom with heated tile floors, and generous closet space. Two additional bedrooms, plus a den that could serve as a fourth bedroom and custom bathroom. Step outside to a screened porch with awning or lounge beside the tiled gunite heated saltwater pool, Pebblesheen finish and surrounded by a custom deck—perfect for entertaining or quiet relaxation. Additional highlights include a two-car garage with attic storage, a laundry room with utility sink, stacked washer/dryer, and a 4-ton Legacy heat pump for year-round comfort. This is a rare opportunity to own a meticulously maintained home in one of St. Michaels’ most desirable communities, where privacy, luxury, and a waterfront lifestyle come together beautifully. Experience life alongside one of Maryland’s finest golf courses - across the street of the award-winning Links at Perry Cabin Golf Course—a premier golf destination designed by the legendary Pete Dye.

$1,840,000

4 Beds ⋅ 3 Baths

Nestled on 2.3 private acres in the sought-after Martingham neighborhood, this beautifully updated waterfront home offers one level living with the perfect blend of comfort, style, and outdoor living. Overlooking Porter Creek, the property features a private pier with lift and rip-rapped shoreline, where you can enjoy breathtaking sunsets, and endless days enjoying the water. Inside, the open floor plan flows effortlessly from the spacious living areas, open dining area, to the fully renovated kitchen, complete with quartz countertops, custom cabinetry, and modern appliances. The expansive waterside owner’s suite has a luxurious bathroom with heated tile floors, and generous closet space. Two additional bedrooms, plus a den that could serve as a fourth bedroom and custom bathroom. Step outside to a screened porch with awning or lounge beside the tiled gunite heated saltwater pool, Pebblesheen finish and surrounded by a custom deck—perfect for entertaining or quiet relaxation. Additional highlights include a two-car garage with attic storage, a laundry room with utility sink, stacked washer/dryer, and a 4-ton Legacy heat pump for year-round comfort. This is a rare opportunity to own a meticulously maintained home in one of St. Michaels’ most desirable communities, where privacy, luxury, and a waterfront lifestyle come together beautifully. Experience life alongside one of Maryland’s finest golf courses - across the street of the award-winning Links at Perry Cabin Golf Course—a premier golf destination designed by the legendary Pete Dye.

9788 Pintail Pl, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come By Chance’s, design team. Across living spaces, you’ll enjoy quiet refinement of the original 1996 construction as hand-scraped hardwoods, tailored millwork, crisp coastal hues, and light-filled windows frame seasonal harbor moments. Host visiting guests near your wood-burning hearth where built-ins hold favorite reads, collected shells, and travel mementos. Here, both curated and comfortably lived-in personality mirror mornings with coffee and dinner aromas from your breezy kitchen of high-end appliances, stone surfaces, and a central island. While everything from simple breakfasts to generous crab feasts overlook nautical views from your sunlit sitting room, you’re sure to linger long after meals from either of the double balconies. Here, let casual conversation entertain, then settle within either of your three serene bedrooms letting two full and one half baths refresh. Outside, toss yard toys for a four legged friend, cast off kayaks towards quiet coves, or set sail into the open expanse of the Chesapeake Bay. Closer to home, afternoons unfold, just a stroll’s-distance away toward daily discoveries within nearby St. Michaels shops, cafés, museums, and the yacht club.

$1,825,000

Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come By Chance’s, design team. Across living spaces, you’ll enjoy quiet refinement of the original 1996 construction as hand-scraped hardwoods, tailored millwork, crisp coastal hues, and light-filled windows frame seasonal harbor moments. Host visiting guests near your wood-burning hearth where built-ins hold favorite reads, collected shells, and travel mementos. Here, both curated and comfortably lived-in personality mirror mornings with coffee and dinner aromas from your breezy kitchen of high-end appliances, stone surfaces, and a central island. While everything from simple breakfasts to generous crab feasts overlook nautical views from your sunlit sitting room, you’re sure to linger long after meals from either of the double balconies. Here, let casual conversation entertain, then settle within either of your three serene bedrooms letting two full and one half baths refresh. Outside, toss yard toys for a four legged friend, cast off kayaks towards quiet coves, or set sail into the open expanse of the Chesapeake Bay. Closer to home, afternoons unfold, just a stroll’s-distance away toward daily discoveries within nearby St. Michaels shops, cafés, museums, and the yacht club.

222 Chestnut, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Nestled beneath a canopy of mature pines along the protected waters of Solitude Creek, this beautifully renovated waterfront retreat captures the timeless appeal of Maryland's Eastern Shore. Occupying approximately 2.745 private acres with nearly 200 feet of shoreline, the property offers an exceptional blend of privacy, boating, and relaxed luxury—just minutes from the historic waterfront town of St. Michaels. Renovated in 2020, the residence pairs classic coastal architecture with bright, contemporary interiors designed to embrace natural light and peaceful water views. Spanning approximately 2,100 square feet, the home offers four bedrooms and two-and-a-half baths, all arranged on a single level for effortless everyday living. Warm hardwood floors, custom millwork, and an inviting fireplace create an atmosphere that is both elegant and welcoming, while expansive windows frame the surrounding landscape and shimmering creek beyond. At the heart of the home, a beautifully appointed gourmet kitchen features custom cabinetry, granite countertops, a generous center island, and vaulted ceilings that flow seamlessly into open dining and living spaces. Created for gathering with family and friends, these light-filled interiors extend naturally onto an expansive waterside composite deck—an ideal setting for morning coffee, sunset cocktails, or alfresco dinners overlooking the water. The primary suite offers a beautifully finished bath, while three additional guest bedrooms provide comfortable accommodations for family and visitors. Every room reflects a timeless aesthetic that complements the property's serene waterfront surroundings. A private pier with a 9,000-pound boat lift and approximately 6 feet of mean low water offers exceptional boating for a wide variety of vessels. The property's seamless connection to the Choptank River and surrounding tributaries creates a waterfront lifestyle defined by both privacy and adventure. Whether arriving by boat or by car, few locations offer such a remarkable balance of seclusion, convenience, and direct access to some of the Eastern Shore's most celebrated waterways. A detached two-car garage with loft space above provides abundant storage and flexibility for hobbies, a workshop, or future possibilities. Mature landscaping, towering pines, and exceptional privacy complete this rare waterfront offering. The adjacent 3.21± acre waterfront lot to the north is also available for purchase at $895,000. Additional information is available from the listing agent upon request

$1,595,000

4 Beds ⋅ 3 Baths

Nestled beneath a canopy of mature pines along the protected waters of Solitude Creek, this beautifully renovated waterfront retreat captures the timeless appeal of Maryland's Eastern Shore. Occupying approximately 2.745 private acres with nearly 200 feet of shoreline, the property offers an exceptional blend of privacy, boating, and relaxed luxury—just minutes from the historic waterfront town of St. Michaels. Renovated in 2020, the residence pairs classic coastal architecture with bright, contemporary interiors designed to embrace natural light and peaceful water views. Spanning approximately 2,100 square feet, the home offers four bedrooms and two-and-a-half baths, all arranged on a single level for effortless everyday living. Warm hardwood floors, custom millwork, and an inviting fireplace create an atmosphere that is both elegant and welcoming, while expansive windows frame the surrounding landscape and shimmering creek beyond. At the heart of the home, a beautifully appointed gourmet kitchen features custom cabinetry, granite countertops, a generous center island, and vaulted ceilings that flow seamlessly into open dining and living spaces. Created for gathering with family and friends, these light-filled interiors extend naturally onto an expansive waterside composite deck—an ideal setting for morning coffee, sunset cocktails, or alfresco dinners overlooking the water. The primary suite offers a beautifully finished bath, while three additional guest bedrooms provide comfortable accommodations for family and visitors. Every room reflects a timeless aesthetic that complements the property's serene waterfront surroundings. A private pier with a 9,000-pound boat lift and approximately 6 feet of mean low water offers exceptional boating for a wide variety of vessels. The property's seamless connection to the Choptank River and surrounding tributaries creates a waterfront lifestyle defined by both privacy and adventure. Whether arriving by boat or by car, few locations offer such a remarkable balance of seclusion, convenience, and direct access to some of the Eastern Shore's most celebrated waterways. A detached two-car garage with loft space above provides abundant storage and flexibility for hobbies, a workshop, or future possibilities. Mature landscaping, towering pines, and exceptional privacy complete this rare waterfront offering. The adjacent 3.21± acre waterfront lot to the north is also available for purchase at $895,000. Additional information is available from the listing agent upon request

6905 Pea Nck, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Lndg, Saint Michaels

$1,550,000

3 Beds ⋅ 2 Baths

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Lndg, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact:

PRICE REDUCED: Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is "move in ready" and ready to enjoy the Summer in Saint Michaels. 216 E Chew Ave. is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2-car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the "Conservatory". It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for spacious ground floor master suite as double closets and laundry plumbing already exist in addition to plumbing for a wet bar. Two sets of French doors open to either the front lawn or side yard for entertaining and outdoor grilling and dining. The side yard has a southern exposure and paver patios for a dining set and a fire pit. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the beautiful sunrises and sunsets. Now offered at a REDUCED PRICE, this home also has the lowest price per square foot for a Luxury, Waterview, in town home (under $450), making it a comparatively excellent value. This rare combination of location, quality, amenities and value cannot be replicated in the Saint Michaels market. Do not miss the opportunity to enjoy all that is special about Saint Michaels that comes with this special home.

$1,522,000

4 Beds ⋅ 4 Baths

PRICE REDUCED: Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is "move in ready" and ready to enjoy the Summer in Saint Michaels. 216 E Chew Ave. is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2-car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the "Conservatory". It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for spacious ground floor master suite as double closets and laundry plumbing already exist in addition to plumbing for a wet bar. Two sets of French doors open to either the front lawn or side yard for entertaining and outdoor grilling and dining. The side yard has a southern exposure and paver patios for a dining set and a fire pit. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the beautiful sunrises and sunsets. Now offered at a REDUCED PRICE, this home also has the lowest price per square foot for a Luxury, Waterview, in town home (under $450), making it a comparatively excellent value. This rare combination of location, quality, amenities and value cannot be replicated in the Saint Michaels market. Do not miss the opportunity to enjoy all that is special about Saint Michaels that comes with this special home.

216 E Chew Ave, Saint Michaels

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub, and double vanity. Upstairs, enjoy a private balcony with elevated water views, while the rear composite deck provides the perfect setting for everyday living and entertaining, all overlooking the Miles River. The outdoor space is designed to impress, complete with hardscaped pavers, a gas-connected grill, pizza oven, and propane fire table. A private dock offers direct water access, ideal for boating, kayaking, or simply enjoying the waterfront lifestyle. Additional highlights include new LVP flooring, a new furnace, encapsulated crawlspace, and a newly installed irrigation system to maintain the home’s mature landscaping and hydrangeas. A detached garage and access to a nearby community dock within walking distance further enhance the lifestyle this property offers. Tax record indicates wrong square footage, actual square footage of the home is 3,076 square feet of living space. *** Settlement cannot occur before September 10th, 2026***

$1,500,000

Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub, and double vanity. Upstairs, enjoy a private balcony with elevated water views, while the rear composite deck provides the perfect setting for everyday living and entertaining, all overlooking the Miles River. The outdoor space is designed to impress, complete with hardscaped pavers, a gas-connected grill, pizza oven, and propane fire table. A private dock offers direct water access, ideal for boating, kayaking, or simply enjoying the waterfront lifestyle. Additional highlights include new LVP flooring, a new furnace, encapsulated crawlspace, and a newly installed irrigation system to maintain the home’s mature landscaping and hydrangeas. A detached garage and access to a nearby community dock within walking distance further enhance the lifestyle this property offers. Tax record indicates wrong square footage, actual square footage of the home is 3,076 square feet of living space. *** Settlement cannot occur before September 10th, 2026***

602 Landing Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.

$1,395,000

121 West Chestnut Street is a true gem among the historic houses in St. Michaels. First time offered in a decade, the 1890 colonial embodies all the desirable features of an older home on the exterior – an inviting covered front porch, wood shingle siding, a two-bay center hall two story architecture, bracing chimneys on each end and true divided double hung windows in the front. Once inside, this home surprises with a light filled open interior and a seamlessly flowing floor plan. The important historic features, such as wood flooring, built ins and fireplace have been well preserved, but with its well thought out renovations and a sizable addition, the house now features large open rooms, an impressive gourmet kitchen and an attractive modern primary bedroom with walk-in closet and bath. The kitchen opens to the back yard and features a large island with seating for five, farm sink, five burner gas cooktop with faucet, wall oven and convection microwave, ample cabinet space, and granite and quartz counters. The adjacent dining room includes built ins with a beverage refrigerator and a decorative fireplace that could be converted to electric or gas. The living room is anchored by a gas fireplace, built in cabinets, and shelving. The home offers four bedrooms, one of which currently serves as an office, accessible from both the primary and secondary staircase. The living area is rounded out by a dedicated laundry room with access to the backyard, and a sitting room. The lot has alley access from the back and while currently not in place, could have parking at the rear. A sizable outbuilding offers plenty of space for storage. This home is just steps away from the park and public dock on San Domingo Creek, and the St. Michaels Nature Trail.

121 W Chestnut, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

The owner must approve all showings, advance notice is preferred. REAL ESTATE ONLY FOR SALE. Positioned in the heart of downtown St. Michaels, 208 N Talbot Street offers a rare opportunity to acquire a premier mixed-use commercial property in one of the Eastern Shore’s most desirable waterfront communities. This 4,111-square-foot building features outstanding visibility along Talbot Street, benefiting from strong pedestrian traffic and close proximity to the waterfront, marinas, boutique shops, and established dining destinations. The property is ideally suited for a restaurant or hospitality concept, featuring a fully built-out commercial kitchen and an impressive total seating capacity of approximately 158 guests across indoor and outdoor dining areas. This allows a new owner to open and operate with minimal additional build-out—an increasingly rare opportunity in this market. A standout feature is the inclusion of 12 dedicated parking spaces, a significant advantage in downtown St. Michaels, enhancing accessibility for both customers and staff. The second level, which has outside access, offers a spacious three-bedroom, three-bathroom apartment, providing excellent flexibility for owner occupancy or future rental income. The apartment kitchen is currently unfinished, needs some remodelling, upstairs offering the opportunity for customization while adding additional long-term value once completed. Whether positioned as a signature dining establishment, boutique hospitality concept, or mixed-use investment, this property delivers a compelling combination of location, infrastructure, and upside potential in a market where inventory remains limited. The property is sold as is. Recommend each individual buyer check with the Town Office for uses for 2nd level.

$1,250,000

208 N Talbot, Saint Michaels

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

Selling Office: Non Subscribing Office.

$1,225,000

Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore’s most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern conveniences throughout. Inside, a bright open-concept floor plan creates an inviting atmosphere ideal for both everyday living and entertaining. The beautifully designed kitchen with all-new appliances flows seamlessly into the main living spaces, while tastefully updated bathrooms and carefully curated details reflect the quality of this full-scale restoration. The home offers the comfort and efficiency of geothermal HVAC, a central vacuum system, new roof, and a fully encapsulated crawl space, providing peace of mind alongside modern performance. The primary suite is a private retreat, featuring a luxurious bathroom, plenty of closet space, and a walk-out rooftop deck overlooking the backyard—the perfect place to enjoy quiet mornings with coffee or unwind under the evening sky. Outdoors, the property continues to impress with a generous yard enhanced by natural walkways, native plants, and thoughtfully designed landscaping, creating a serene garden-like setting. Additional highlights include a one-car garage with workbench and storage, along with a separate workshop that offers flexible space for hobbies, studio use, or potential guest accommodations. Ideally located within walking distance to St. Michaels’ charming harbor, boutique shops, galleries, and renowned restaurants, this home offers the rare opportunity to enjoy historic town living with the comfort of a completely modernized residence. A truly exceptional offering in the heart of St. Michaels.

2 Beds ⋅ 3 Baths

Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore’s most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern conveniences throughout. Inside, a bright open-concept floor plan creates an inviting atmosphere ideal for both everyday living and entertaining. The beautifully designed kitchen with all-new appliances flows seamlessly into the main living spaces, while tastefully updated bathrooms and carefully curated details reflect the quality of this full-scale restoration. The home offers the comfort and efficiency of geothermal HVAC, a central vacuum system, new roof, and a fully encapsulated crawl space, providing peace of mind alongside modern performance. The primary suite is a private retreat, featuring a luxurious bathroom, plenty of closet space, and a walk-out rooftop deck overlooking the backyard—the perfect place to enjoy quiet mornings with coffee or unwind under the evening sky. Outdoors, the property continues to impress with a generous yard enhanced by natural walkways, native plants, and thoughtfully designed landscaping, creating a serene garden-like setting. Additional highlights include a one-car garage with workbench and storage, along with a separate workshop that offers flexible space for hobbies, studio use, or potential guest accommodations. Ideally located within walking distance to St. Michaels’ charming harbor, boutique shops, galleries, and renowned restaurants, this home offers the rare opportunity to enjoy historic town living with the comfort of a completely modernized residence. A truly exceptional offering in the heart of St. Michaels.

106 Chestnut St E, Saint Michaels

Listing courtesy of Taylor Properties. Contact:

$1,187,500

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

344 Perry Cabin Dr, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$1,152,500

The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not subject to St. Michaels Historic District regulations. The home features an exceptional main-level primary suite with vaulted ceiling, three walk-in closets, en suite bath, and serene views of the private yard; an updated kitchen with large center island, granite countertops, stainless steel appliances, abundant storage, and casual dining overlooking the gardens; three main-level living spaces including a bright sunroom/library, spacious family room with brick fireplace, and the original welcoming living room; along with a formal dining room and powder room. Upstairs are two additional bedrooms and a full bath. The fenced backyard offers a patio beneath a magnificent magnolia, and a detached structure with a half bath provides the perfect space for a private office, studio, or creative retreat, complemented by a potting shed and additional storage. Off-street parking from both New Lane and E. Chew completes this exceptional in-town offering.

The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not subject to St. Michaels Historic District regulations. The home features an exceptional main-level primary suite with vaulted ceiling, three walk-in closets, en suite bath, and serene views of the private yard; an updated kitchen with large center island, granite countertops, stainless steel appliances, abundant storage, and casual dining overlooking the gardens; three main-level living spaces including a bright sunroom/library, spacious family room with brick fireplace, and the original welcoming living room; along with a formal dining room and powder room. Upstairs are two additional bedrooms and a full bath. The fenced backyard offers a patio beneath a magnificent magnolia, and a detached structure with a half bath provides the perfect space for a private office, studio, or creative retreat, complemented by a potting shed and additional storage. Off-street parking from both New Lane and E. Chew completes this exceptional in-town offering.

114 E Chew Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$1,135,000

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

2 Beds ⋅ 2 Baths

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

107 E Chestnut, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: RE/MAX Executive.

$1,012,000

Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bentley Hay neighborhood just minutes from historic downtown St. Michaels. This beautifully renovated & meticulously maintained home offers Miles River views, a saltwater pool, 1st floor primary bedroom, attached 2 car garage, screened in porch, hardwood floors, gardens, home office, fiber optic cable, new roof, new HVAC & encapsulated crawlspace. Enter the impressive two-story foyer and enjoy a direct view through the home to the pool beyond. The open living room features a dramatic vaulted shiplap ceiling, built in bookcases, entertainment cabinet & gas fireplace. Off the living room is a custom 2 desk, dedicated office with storage cabinets. Enjoy cooking in the elegantly renovated kitchen with French Blue cabinetry, granite & marble countertops, cutting board topped island, stainless steel appliances including a CAFE range with copper handles. The first-floor primary suite is open & spacious with high ceilings with views of the pool & backyard. The primary bathroom has designer tile walk-in shower & flooring with a double sink vanity with marble countertop. The 2nd floor features a wonderful family room with oversize windows & waterviews over the Miles River, 2 large, lovely bedrooms, full bath & walk in attic. Enjoy the screened-in porch overlooking the inviting saltwater pool with durable Trex decking, relax in your private, fenced backyard, with raised gardens & vegetable beds—perfect for entertaining, gardening, or simply enjoying the Eastern Shore lifestyle. The property is zoned to allow short-term rentals with County approval, offering added flexibility as a primary residence, second home, or investment opportunity. This home checks all the boxes!

Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bentley Hay neighborhood just minutes from historic downtown St. Michaels. This beautifully renovated & meticulously maintained home offers Miles River views, a saltwater pool, 1st floor primary bedroom, attached 2 car garage, screened in porch, hardwood floors, gardens, home office, fiber optic cable, new roof, new HVAC & encapsulated crawlspace. Enter the impressive two-story foyer and enjoy a direct view through the home to the pool beyond. The open living room features a dramatic vaulted shiplap ceiling, built in bookcases, entertainment cabinet & gas fireplace. Off the living room is a custom 2 desk, dedicated office with storage cabinets. Enjoy cooking in the elegantly renovated kitchen with French Blue cabinetry, granite & marble countertops, cutting board topped island, stainless steel appliances including a CAFE range with copper handles. The first-floor primary suite is open & spacious with high ceilings with views of the pool & backyard. The primary bathroom has designer tile walk-in shower & flooring with a double sink vanity with marble countertop. The 2nd floor features a wonderful family room with oversize windows & waterviews over the Miles River, 2 large, lovely bedrooms, full bath & walk in attic. Enjoy the screened-in porch overlooking the inviting saltwater pool with durable Trex decking, relax in your private, fenced backyard, with raised gardens & vegetable beds—perfect for entertaining, gardening, or simply enjoying the Eastern Shore lifestyle. The property is zoned to allow short-term rentals with County approval, offering added flexibility as a primary residence, second home, or investment opportunity. This home checks all the boxes!

925 Riverview Ter, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200 sf main level offers beautiful open large living room with fireplace and dining room for entertainment, which leads to fabulous sunroom overlooking the back yard garden. Modern kitchen off the dining room that leads to cozy breakfast room and back porch and patio. The Master suite has a completely remodeled bath with free standing soaker tub, walk in shower, his and hers vanities, as well as laundry. The key to this home is the second floor. This 800 SF space offers unimaginable flexibility. It can be various spaces based on your needs. A private space for your guests when visiting, a space for family and grandchildren, an in-law suite, or as a rental apartment with private entrance. Space is built to accommodate all the above with out any changes required. At present it has a living room, dining room, kitchen, bedroom and full bath with laundry, and under eave storage. The space, with the addition of one wall can add an additional bedroom making the property with all the aforementioned, a 3-bedroom home. In the backyard you will find self-contained workshop with HVAC, hot and cold running water, and attic, a Williamsburg garden shed, and parking for 3-4 cars. Home has encapsulated crawl space, and 2 zoned HVAC system.

$969,000

This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200 sf main level offers beautiful open large living room with fireplace and dining room for entertainment, which leads to fabulous sunroom overlooking the back yard garden. Modern kitchen off the dining room that leads to cozy breakfast room and back porch and patio. The Master suite has a completely remodeled bath with free standing soaker tub, walk in shower, his and hers vanities, as well as laundry. The key to this home is the second floor. This 800 SF space offers unimaginable flexibility. It can be various spaces based on your needs. A private space for your guests when visiting, a space for family and grandchildren, an in-law suite, or as a rental apartment with private entrance. Space is built to accommodate all the above with out any changes required. At present it has a living room, dining room, kitchen, bedroom and full bath with laundry, and under eave storage. The space, with the addition of one wall can add an additional bedroom making the property with all the aforementioned, a 3-bedroom home. In the backyard you will find self-contained workshop with HVAC, hot and cold running water, and attic, a Williamsburg garden shed, and parking for 3-4 cars. Home has encapsulated crawl space, and 2 zoned HVAC system.

504 Seymour Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$947,000

Professional photos coming. Welcome to historic St. Michaels on the Miles River. This 3 bedroom, 2.5 bath townhouse comes with a designated deep water ( 6 Ft. MLW) boat slip ( #360). Enjoy the tranquil views from your back deck or the balcony off the primary bedroom. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Downstairs flooring is hardwood, the living room has a wood burning fireplace for cozy evenings, there is a separate laundry room and an eat in kitchen. The community offers access to tennis courts lined for pickleball, deep-water docks with water and power, beach access, and a private waterfront walkway - ideal for boating, kayaking, paddleboarding and enjoying time on the water. This unit is ideally located for the best views and privacy. Ideal location close to St. Michaels restaurants, shops and harbor. Take advantage of the Inn at Perry Cabin for dining and the luxurious spa! Minutes away is the Links at Perry Cabin premier golf destination designed by the legendary Pete Dye. This 18-hole championship course offers a challenging and picturesque experience.

Professional photos coming. Welcome to historic St. Michaels on the Miles River. This 3 bedroom, 2.5 bath townhouse comes with a designated deep water ( 6 Ft. MLW) boat slip ( #360). Enjoy the tranquil views from your back deck or the balcony off the primary bedroom. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Downstairs flooring is hardwood, the living room has a wood burning fireplace for cozy evenings, there is a separate laundry room and an eat in kitchen. The community offers access to tennis courts lined for pickleball, deep-water docks with water and power, beach access, and a private waterfront walkway - ideal for boating, kayaking, paddleboarding and enjoying time on the water. This unit is ideally located for the best views and privacy. Ideal location close to St. Michaels restaurants, shops and harbor. Take advantage of the Inn at Perry Cabin for dining and the luxurious spa! Minutes away is the Links at Perry Cabin premier golf destination designed by the legendary Pete Dye. This 18-hole championship course offers a challenging and picturesque experience.

360 Perry Cabin, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$877,000

Welcome to 24896 Back Creek Drive Saint Michaels, a coastal home with one of the most beautiful back yard pond views available in the entire community! This property has so much a buyer may desire--modern, coastal design, open concept living, soaring ceilings, a large fenced back yard, broad views of a beautiful pond, water access approx 0.2 miles down the community pathway to San Domingo Creek for kayaking/paddleboarding, an abundance of space, a kitchen with a spectacular gas stove and two ovens, a gas fireplace, recently planted privacy trees, an encapsulated crawl space and so much more! You will be the envy of family and/or friends as you all sit around the enormous 90" flat screen television over the fireplace to take in sporting events or shows (television conveys with the property) or when you sit around the new hardscape fire pit boasting a new, large pellet/wood burning stove (which also conveys, along with the four new Adirondack chairs)! If you prefer to take in the spectacular water view from the nice deck or the large four season sunroom, either is an excellent option! The primary suite is on the main floor with all other bedrooms upstairs. There is an option to have an upstairs primary en suite if you prefer being on the same floor as other bedrooms. This property has sold in past listed as a five bedroom property so is listed as such again. Please be advised two of the five bedrooms do not have closets; wardrobes have been used in past listing of the property. Closets can easily be built in those two bedrooms--there is tremendous space to do so. Recent seller upgrades include a newly paved driveway, fire pit hardscape and pellet/wood fire pit (which conveys with the sale of the property), kitchen cabinet handles/pulls, entire exterior of the home was power washed, The crawl space is encapsulated. This property is very close to a grocery store, coffee place, bank and gas station. St Michaels' Historic District can be reached in mere minutes by car or on foot. The Y, community pool, Miles River Yacht Club, Chesapeake Bay Maritime Museum, Inn at Perry Cabin, golf, are all in proximity.

5 Beds ⋅ 5 Baths

Welcome to 24896 Back Creek Drive Saint Michaels, a coastal home with one of the most beautiful back yard pond views available in the entire community! This property has so much a buyer may desire--modern, coastal design, open concept living, soaring ceilings, a large fenced back yard, broad views of a beautiful pond, water access approx 0.2 miles down the community pathway to San Domingo Creek for kayaking/paddleboarding, an abundance of space, a kitchen with a spectacular gas stove and two ovens, a gas fireplace, recently planted privacy trees, an encapsulated crawl space and so much more! You will be the envy of family and/or friends as you all sit around the enormous 90" flat screen television over the fireplace to take in sporting events or shows (television conveys with the property) or when you sit around the new hardscape fire pit boasting a new, large pellet/wood burning stove (which also conveys, along with the four new Adirondack chairs)! If you prefer to take in the spectacular water view from the nice deck or the large four season sunroom, either is an excellent option! The primary suite is on the main floor with all other bedrooms upstairs. There is an option to have an upstairs primary en suite if you prefer being on the same floor as other bedrooms. This property has sold in past listed as a five bedroom property so is listed as such again. Please be advised two of the five bedrooms do not have closets; wardrobes have been used in past listing of the property. Closets can easily be built in those two bedrooms--there is tremendous space to do so. Recent seller upgrades include a newly paved driveway, fire pit hardscape and pellet/wood fire pit (which conveys with the sale of the property), kitchen cabinet handles/pulls, entire exterior of the home was power washed, The crawl space is encapsulated. This property is very close to a grocery store, coffee place, bank and gas station. St Michaels' Historic District can be reached in mere minutes by car or on foot. The Y, community pool, Miles River Yacht Club, Chesapeake Bay Maritime Museum, Inn at Perry Cabin, golf, are all in proximity.

24896 Back Crk, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles River—a treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electric vehicle charging station in the garage Invisible pet fence surrounding the yard The serene setting, spectacular views, and extensive updates create a rare opportunity to enjoy a low-maintenance lifestyle in a premier St. Michaels location. Whether relaxing on the patio overlooking the pond and golf course or enjoying the community's private waterfront park, this home offers the perfect blend of luxury, comfort, and convenience. A truly turnkey property where every detail has been thoughtfully updated and impeccably maintained.

$775,000

4 Beds ⋅ 3 Baths

Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles River—a treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electric vehicle charging station in the garage Invisible pet fence surrounding the yard The serene setting, spectacular views, and extensive updates create a rare opportunity to enjoy a low-maintenance lifestyle in a premier St. Michaels location. Whether relaxing on the patio overlooking the pond and golf course or enjoying the community's private waterfront park, this home offers the perfect blend of luxury, comfort, and convenience. A truly turnkey property where every detail has been thoughtfully updated and impeccably maintained.

9359 Martingham, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Discover a beautifully crafted custom home tucked within the peaceful St. Michaels community, where refined design meets everyday comfort. This exceptional residence offers 4 generously sized bedrooms and 3.5 thoughtfully designed bathrooms, filled with premium details throughout. The versatile gas fireplace anchors the inviting main living space, complemented by custom built-ins that add both character and functionality. The expansive primary suite is a true retreat, featuring an oversized walk-in closet and a spa-inspired bathroom with a large custom shower and new fixtures. A second-floor en suite bedroom provides an ideal option for guests or multigenerational living. Outdoor living shines on the sprawling Trex deck, complete with a Sunsetter awning and a fully fenced backyard—perfect for entertaining or unwinding in privacy. Additional highlights include a large walk-in storage attic with the potential to convert into a fifth bedroom, office, or media room. Recent upgrades such as a newer first-floor HVAC system, a brand-new second-floor HVAC, an updated 80-gallon hot water heater, and a freshly painted interior ensure comfort, efficiency, and move-in readiness. Set within a tranquil 40-acre enclave featuring walking trails, ponds, and waterfront access along scenic San Domingo Creek, this home offers a rare blend of natural beauty and convenience. Enjoy easy access to downtown St. Michaels while benefiting from no town taxes. A truly special home that delivers relaxed luxury, space to grow, and an exceptional Eastern Shore lifestyle.

$685,000

4 Beds ⋅ 4 Baths

Discover a beautifully crafted custom home tucked within the peaceful St. Michaels community, where refined design meets everyday comfort. This exceptional residence offers 4 generously sized bedrooms and 3.5 thoughtfully designed bathrooms, filled with premium details throughout. The versatile gas fireplace anchors the inviting main living space, complemented by custom built-ins that add both character and functionality. The expansive primary suite is a true retreat, featuring an oversized walk-in closet and a spa-inspired bathroom with a large custom shower and new fixtures. A second-floor en suite bedroom provides an ideal option for guests or multigenerational living. Outdoor living shines on the sprawling Trex deck, complete with a Sunsetter awning and a fully fenced backyard—perfect for entertaining or unwinding in privacy. Additional highlights include a large walk-in storage attic with the potential to convert into a fifth bedroom, office, or media room. Recent upgrades such as a newer first-floor HVAC system, a brand-new second-floor HVAC, an updated 80-gallon hot water heater, and a freshly painted interior ensure comfort, efficiency, and move-in readiness. Set within a tranquil 40-acre enclave featuring walking trails, ponds, and waterfront access along scenic San Domingo Creek, this home offers a rare blend of natural beauty and convenience. Enjoy easy access to downtown St. Michaels while benefiting from no town taxes. A truly special home that delivers relaxed luxury, space to grow, and an exceptional Eastern Shore lifestyle.

24977 Back Creek Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: