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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:

Selling Office: Meredith Fine Properties.

$2,200,000

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.

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:

"Whispering Pines" A beautiful waterfront escape on private 2.75 +/- acre lot located within walking and biking distance from historic downtown St Michaels. Spacious, light and airy 4000+ sq foot 3BR 3BA home, custom built in 1996 boasts a desirable large, entry-level, primary suite, 2 en-suite bathrooms upstairs, spacious family room with cathedral ceiling and cozy wood burning fireplace, open kitchen, den with beautiful built-ins, bonus room/4th bedroom above attached 2 car garage, and a terrific sun room. Shed with electric, outdoor lighting - including at driveway entrance. 260' +/- of protected shoreline with high elevation, 6-foot-wide pier with electric and water, 3+/-feet MLW , room for a pool. Backyard patio to enjoy amazing sunsets over Broad and Rolles Creek. Sewer line installation along primary road currently underway. Property sold as-is, inspections for informational purposes only.

$1,800,000

3 Beds ⋅ 4 Baths

"Whispering Pines" A beautiful waterfront escape on private 2.75 +/- acre lot located within walking and biking distance from historic downtown St Michaels. Spacious, light and airy 4000+ sq foot 3BR 3BA home, custom built in 1996 boasts a desirable large, entry-level, primary suite, 2 en-suite bathrooms upstairs, spacious family room with cathedral ceiling and cozy wood burning fireplace, open kitchen, den with beautiful built-ins, bonus room/4th bedroom above attached 2 car garage, and a terrific sun room. Shed with electric, outdoor lighting - including at driveway entrance. 260' +/- of protected shoreline with high elevation, 6-foot-wide pier with electric and water, 3+/-feet MLW , room for a pool. Backyard patio to enjoy amazing sunsets over Broad and Rolles Creek. Sewer line installation along primary road currently underway. Property sold as-is, inspections for informational purposes only.

23854 Mount Misery Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Welcome to Heron Cove Farm, a beautiful waterfront paradise situated on the banks of Broad Creek, just outside of Historic Saint Michaels, MD. This masterfully renovated home offers the convenience of one level living in a private setting of over 15 acres creating the feel of a peaceful escape, yet only two miles from the restaurants, shops and social network of town. Whether you enjoy relaxing on the deck, enjoying the pool, or spending the day boating along the Chesapeake Bay, this property is a complete show stopper! Three separate storage barns can store your toys and equipment, provide a base for horses, or create an opportunity for expansion. Bring your dreams and excitement alive for care free living!

$1,600,000

3 Beds ⋅ 2 Baths

Welcome to Heron Cove Farm, a beautiful waterfront paradise situated on the banks of Broad Creek, just outside of Historic Saint Michaels, MD. This masterfully renovated home offers the convenience of one level living in a private setting of over 15 acres creating the feel of a peaceful escape, yet only two miles from the restaurants, shops and social network of town. Whether you enjoy relaxing on the deck, enjoying the pool, or spending the day boating along the Chesapeake Bay, this property is a complete show stopper! Three separate storage barns can store your toys and equipment, provide a base for horses, or create an opportunity for expansion. Bring your dreams and excitement alive for care free living!

23869 New Land Dr, Saint Michaels

Listing courtesy of Meredith Fine Properties. 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:

Selling Office: Meredith Fine Properties.

$1,522,000

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.

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:

Welcome to Saint Michaels Retreat—an extraordinary 6-acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and the Miles River. Just minutes from downtown Saint Michaels, this stunningly renovated residence offers over 4,100 sq. ft. of one-level living, thoughtfully designed for effortless indoor and outdoor entertaining. Inside, expansive living and dining areas feature 12-foot ceilings and abundant light. The custom kitchen and family room with gas fireplace anchor the home, while the welcoming foyer, formal living/dining rooms, and serene primary suite—with walk-in closet, built-ins, and a spa-like bath—all open to sweeping views of the pool, patio, and gardens. The gourmet kitchen showcases an oversized island with farm sink, walk-in pantry, wine cooler, extensive cabinetry, and top-of-the-line appliances, creating the perfect setting for both everyday living and memorable gatherings. Three additional bedrooms are well-appointed and share a spacious full hall bath. A private office with additional storage provides a quiet retreat for work or study. A mudroom with custom cabinetry and cedar closet, laundry room with new washer/dryer and utility sink, powder room, and a three-car garage provide both comfort and convenience. Renovated inside and out, the home highlights new flooring, upgraded fixtures and lighting, high-efficiency HVAC and water heater, and large Andersen windows that bathe each room in light. Outdoor living is equally inviting with a gunite pool (new filter and pump), expansive covered patio, pergola, paver-lined walkways, and a pool closet, plus a large shed for extra storage. A full bath just off the family room provides easy access to the pool area. Mature landscaping, a double-access driveway, and private pier (perfect for kayaking or paddle-boarding) complete the property. This remarkable home invites you to embrace the Eastern Shore lifestyle and all the beauty it has to offer. *A list of improvements is available in documents.

$1,500,000

4 Beds ⋅ 4 Baths

Welcome to Saint Michaels Retreat—an extraordinary 6-acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and the Miles River. Just minutes from downtown Saint Michaels, this stunningly renovated residence offers over 4,100 sq. ft. of one-level living, thoughtfully designed for effortless indoor and outdoor entertaining. Inside, expansive living and dining areas feature 12-foot ceilings and abundant light. The custom kitchen and family room with gas fireplace anchor the home, while the welcoming foyer, formal living/dining rooms, and serene primary suite—with walk-in closet, built-ins, and a spa-like bath—all open to sweeping views of the pool, patio, and gardens. The gourmet kitchen showcases an oversized island with farm sink, walk-in pantry, wine cooler, extensive cabinetry, and top-of-the-line appliances, creating the perfect setting for both everyday living and memorable gatherings. Three additional bedrooms are well-appointed and share a spacious full hall bath. A private office with additional storage provides a quiet retreat for work or study. A mudroom with custom cabinetry and cedar closet, laundry room with new washer/dryer and utility sink, powder room, and a three-car garage provide both comfort and convenience. Renovated inside and out, the home highlights new flooring, upgraded fixtures and lighting, high-efficiency HVAC and water heater, and large Andersen windows that bathe each room in light. Outdoor living is equally inviting with a gunite pool (new filter and pump), expansive covered patio, pergola, paver-lined walkways, and a pool closet, plus a large shed for extra storage. A full bath just off the family room provides easy access to the pool area. Mature landscaping, a double-access driveway, and private pier (perfect for kayaking or paddle-boarding) complete the property. This remarkable home invites you to embrace the Eastern Shore lifestyle and all the beauty it has to offer. *A list of improvements is available in documents.

9171 Deepwater Point Rd, Saint Michaels

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

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$1,400,000

Welcome to this enchanting waterfront retreat, beautifully sited on 6.2 acres overlooking Old House Cove with scenic passage out to San Domingo Creek. Designed in a coastal style and offering 3,340 sq. ft., this 4-bedroom, 2.5-bath residence blends timeless comfort with the natural beauty of the Eastern Shore. A charming front porch sets the tone, leading into sunlit living spaces with soaring vaulted ceilings and gleaming American Cherry hardwood floors. The main-level primary suite is a serene haven with a private sitting area and spa-like bath. Upstairs, a loft lounge overlooks the living room and connects to three additional bedrooms and a shared hall bath. The gourmet kitchen, outfitted with premium appliances, flows seamlessly into the dining area, living room with cozy gas fireplace, and waterside sunroom that opens to a deck with sweeping views. A private office, versatile bonus room, and attached 2-car garage add convenience and flexibility. Outdoors, the private pier( with electricity and water) offers two slips and electric lift, inviting endless days on the water, while mature trees, lush landscaping, and native flora frame this idyllic setting. Countless updates further enhance this exceptional St. Michaels offering and a recent survey shows room for pool.

4 Beds ⋅ 3 Baths

Welcome to this enchanting waterfront retreat, beautifully sited on 6.2 acres overlooking Old House Cove with scenic passage out to San Domingo Creek. Designed in a coastal style and offering 3,340 sq. ft., this 4-bedroom, 2.5-bath residence blends timeless comfort with the natural beauty of the Eastern Shore. A charming front porch sets the tone, leading into sunlit living spaces with soaring vaulted ceilings and gleaming American Cherry hardwood floors. The main-level primary suite is a serene haven with a private sitting area and spa-like bath. Upstairs, a loft lounge overlooks the living room and connects to three additional bedrooms and a shared hall bath. The gourmet kitchen, outfitted with premium appliances, flows seamlessly into the dining area, living room with cozy gas fireplace, and waterside sunroom that opens to a deck with sweeping views. A private office, versatile bonus room, and attached 2-car garage add convenience and flexibility. Outdoors, the private pier( with electricity and water) offers two slips and electric lift, inviting endless days on the water, while mature trees, lush landscaping, and native flora frame this idyllic setting. Countless updates further enhance this exceptional St. Michaels offering and a recent survey shows room for pool.

8095 Church Neck Rd, Saint Michaels

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

Selling Office: Coldwell Banker Realty.

$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 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:

Don’t miss this rare opportunity to own one of the most prominent retail locations in St. Michaels. Located at the high-traffic corner of Talbot Street (Route 33) and Railroad Avenue, this property offers approximately 6,000 square feet of space and generous off-street parking. Positioned in the heart of town and close to the marina, restaurants, ice cream shop, and the renowned Maritime Museum.

$1,300,000

100 N Talbot, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

$1,295,000

One of the most admired buildings is St. Michaels is now offered for sale. 202 S. Talbot Street is the tallest building in town with prominent front windows. The 3 story building is currently occupied by one of St. Michael's finest retailers, "Come By Chance". The 2nd and 3rd floor offer incredible potential for the savvy investor as possible options include short term rental units, apartments, and office space. This a timely and great opportunity for an end-user or investor.

202 Talbot, Saint Michaels

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

Selling Office: Meredith Fine Properties.

$1,250,000

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.

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:

7361 Solitude Road, a single-family waterfront rancher set on 2.4 private acres along Solitude Creek, offering approximately 3’ mean low water, a private dock with boat lift, and a secluded setting just minutes from downtown St. Michaels. The home is designed for comfortable single-story living, featuring hardwood floors throughout, a gas fireplace in the main living area, and a primary suite on waterside. The kitchen and living room also overlook the creek, filling the home with natural light and scenic views enhanced by the southeastern exposure. A sunroom off the primary suite leads directly to a composite deck, creating an easy transition to outdoor living. Exterior highlights include an endless pool, waterside decking, and ample space to enjoy boating, kayaking, and the natural setting. Additional features include a paved driveway, two-car garage and a full basement ideal for storage or future use and a detached shed with electric. Offering first-floor living, quality waterfront, and an unbeatable location near St. Michaels, this Eastern Shore retreat is perfectly suited as a full-time residence or weekend escape.

$1,202,000

3 Beds ⋅ 2 Baths

7361 Solitude Road, a single-family waterfront rancher set on 2.4 private acres along Solitude Creek, offering approximately 3’ mean low water, a private dock with boat lift, and a secluded setting just minutes from downtown St. Michaels. The home is designed for comfortable single-story living, featuring hardwood floors throughout, a gas fireplace in the main living area, and a primary suite on waterside. The kitchen and living room also overlook the creek, filling the home with natural light and scenic views enhanced by the southeastern exposure. A sunroom off the primary suite leads directly to a composite deck, creating an easy transition to outdoor living. Exterior highlights include an endless pool, waterside decking, and ample space to enjoy boating, kayaking, and the natural setting. Additional features include a paved driveway, two-car garage and a full basement ideal for storage or future use and a detached shed with electric. Offering first-floor living, quality waterfront, and an unbeatable location near St. Michaels, this Eastern Shore retreat is perfectly suited as a full-time residence or weekend escape.

7361 Solitude Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,187,500