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

114 E Chew Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$1,135,000

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

2 Beds ⋅ 2 Baths

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

107 E Chestnut, Saint Michaels

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

Selling Office: RE/MAX Executive.

$1,130,000

Welcome to Old House Cove Waterfront Retreat in St. Michaels, MD Nestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of Maryland’s most beloved waterfront towns. Formerly owned by the poet and author Gilbert Byron who was often called “the Chesapeake Thoreau,” it is easy to see how the tranquil setting on Old House Cove inspired much of his writing. Originally built in 1965, the main house has been thoughtfully updated to blend classic Eastern Shore style with relaxed modern comfort. The open-concept kitchen, dining, and living area centers around a gas fireplace - all with sweeping water views. Added in 1993, the spacious primary suite features a walk-in closet and en-suite bath. The waterside screened porch is the perfect place to unwind, enjoy the gentle breeze off the water and watch sailboats glide across the cove toward San Domingo Creek. Connected to the main home by a charming pergola walkway, the large carriage house and garage—also constructed in 1993 —includes two bays, one with double doors for boat access. The upper-level guest suite feels like a private treehouse retreat, complete with its own deck and sweeping views of the cove. Together, the main residence and guest suite create an ideal opportunity to expand the property and craft the waterfront home of your dreams—offering privacy, flexibility, and direct access to the property’s stunning setting. Outdoor living is a true highlight of this property. A generous brick terrace provides the perfect space for alfresco dining or entertaining just steps from the water’s edge. The property features approximately 130 feet of rip-rapped shoreline, a sandy kayak launch area, and a private pier equipped with one slip and 2.5’ MLW—ideal easy access to the Bay. Beautiful mature trees, lush landscaping, and a circular drive create an estate-like approach. The property is served by two wells and two septic systems, and sits comfortably in Flood Zone X (no flood insurance required). The area has been approved for public sewer hookup, offering excellent potential for future expansion or reconfiguration to suit your vision. This is a rare opportunity to own a timeless waterfront retreat—where Eastern Shore charm, literary heritage, and modern comfort come together just minutes from the world-class dining, sailing, and small-town allure of St. Michaels, Maryland.

Welcome to Old House Cove Waterfront Retreat in St. Michaels, MD Nestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of Maryland’s most beloved waterfront towns. Formerly owned by the poet and author Gilbert Byron who was often called “the Chesapeake Thoreau,” it is easy to see how the tranquil setting on Old House Cove inspired much of his writing. Originally built in 1965, the main house has been thoughtfully updated to blend classic Eastern Shore style with relaxed modern comfort. The open-concept kitchen, dining, and living area centers around a gas fireplace - all with sweeping water views. Added in 1993, the spacious primary suite features a walk-in closet and en-suite bath. The waterside screened porch is the perfect place to unwind, enjoy the gentle breeze off the water and watch sailboats glide across the cove toward San Domingo Creek. Connected to the main home by a charming pergola walkway, the large carriage house and garage—also constructed in 1993 —includes two bays, one with double doors for boat access. The upper-level guest suite feels like a private treehouse retreat, complete with its own deck and sweeping views of the cove. Together, the main residence and guest suite create an ideal opportunity to expand the property and craft the waterfront home of your dreams—offering privacy, flexibility, and direct access to the property’s stunning setting. Outdoor living is a true highlight of this property. A generous brick terrace provides the perfect space for alfresco dining or entertaining just steps from the water’s edge. The property features approximately 130 feet of rip-rapped shoreline, a sandy kayak launch area, and a private pier equipped with one slip and 2.5’ MLW—ideal easy access to the Bay. Beautiful mature trees, lush landscaping, and a circular drive create an estate-like approach. The property is served by two wells and two septic systems, and sits comfortably in Flood Zone X (no flood insurance required). The area has been approved for public sewer hookup, offering excellent potential for future expansion or reconfiguration to suit your vision. This is a rare opportunity to own a timeless waterfront retreat—where Eastern Shore charm, literary heritage, and modern comfort come together just minutes from the world-class dining, sailing, and small-town allure of St. Michaels, Maryland.

24318 Oakwood Park Rd, Saint Michaels

Listing courtesy of Compass. Contact:

Fabulous waterfront townhome in an exceptional St. Michaels setting, adjacent to the Inn at Perry Cabin with tranquil water views. Designed for comfort and easy living, this 2-bedroom, 2.5-bath residence offers a thoughtfully designed open layout with hardwood floors, fireplace, and sun-filled interiors throughout. Professional photos coming next week. The well-appointed kitchen features Silestone quartz countertops, stainless steel appliances and generous cabinetry, flowing seamlessly into the living and dining areas for effortless everyday living and entertaining. A sunroom with wet bar extends the interior living space and opens to waterside deck. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Recent updates include dual-zone HVAC systems. The property includes a deep-water boat slip (#320) , along with access to tennis courts lined for pickleball, deep-water docks with water and power, beach access, and a private waterfront walkway - ideal for boating, kayaking, paddleboarding and enjoying time on the water. Ideal location close to St. Michaels restaurants, shops and harbor!

$1,118,892

2 Beds ⋅ 3 Baths

Fabulous waterfront townhome in an exceptional St. Michaels setting, adjacent to the Inn at Perry Cabin with tranquil water views. Designed for comfort and easy living, this 2-bedroom, 2.5-bath residence offers a thoughtfully designed open layout with hardwood floors, fireplace, and sun-filled interiors throughout. Professional photos coming next week. The well-appointed kitchen features Silestone quartz countertops, stainless steel appliances and generous cabinetry, flowing seamlessly into the living and dining areas for effortless everyday living and entertaining. A sunroom with wet bar extends the interior living space and opens to waterside deck. The ensuite primary bedroom enjoys water views and a private bath, providing a peaceful retreat. Recent updates include dual-zone HVAC systems. The property includes a deep-water boat slip (#320) , along with access to tennis courts lined for pickleball, deep-water docks with water and power, beach access, and a private waterfront walkway - ideal for boating, kayaking, paddleboarding and enjoying time on the water. Ideal location close to St. Michaels restaurants, shops and harbor!

320 Perry Cabin, Saint Michaels

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

Selling Office: Keller Williams Select Realtors of Easton.

$1,012,000

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

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

925 Riverview Ter, Saint Michaels

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

Selling Office: Benson & Mangold, LLC.

$1,000,000

Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The kitchen was recently renovated and the heating/air conditioning was replaced in 2024. The yard is spacious, with a fenced oyster shell yard featuring a firepit and off street parking for two cars. This home is turnkey - all furnishings and short term rental supplies included. Don't miss this rare opportunity!

2 Beds ⋅ 3 Baths

Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The kitchen was recently renovated and the heating/air conditioning was replaced in 2024. The yard is spacious, with a fenced oyster shell yard featuring a firepit and off street parking for two cars. This home is turnkey - all furnishings and short term rental supplies included. Don't miss this rare opportunity!

100 Grace St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$969,000

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

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

504 Seymour Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

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

9792 Martingham Cir Unit B-4, Saint Michaels

$965,000

Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels! This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer. Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier golf course! This expansive unit offers premium upgraded finishes, a first floor ensuite bedroom, fireplace, and endless enhancements, including new windows and completely new HVAC system. Minutes to town for shopping or award winning dining experiences. This is truly the perfect waterfront, low maintenance getaway that is sure to check all of the boxes of a dream home!

Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels! This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer. Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier golf course! This expansive unit offers premium upgraded finishes, a first floor ensuite bedroom, fireplace, and endless enhancements, including new windows and completely new HVAC system. Minutes to town for shopping or award winning dining experiences. This is truly the perfect waterfront, low maintenance getaway that is sure to check all of the boxes of a dream home!

9792 Martingham Cir Unit B-4, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$947,000

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

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

360 Perry Cabin, Saint Michaels

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

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$926,000

Selling Office: Unrepresented Buyer Office.

203 Mulberry, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$877,000

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

5 Beds ⋅ 5 Baths

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

24896 Back Crk, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Discover the perfect blend of privacy and waterfront living on this exceptional 2.73-acre wooded lot along scenic Broad Creek. With approximately 219 feet of shoreline, this property offers endless opportunities to build your dream home or weekend retreat, complete with stunning water views and direct access for boating, fishing, or kayaking. Surrounded by mature trees, the setting provides both tranquility and natural beauty while still being conveniently located just a few short minutes to St Michaels. Whether you’re envisioning a private getaway or a year-round residence, this rare waterfront gem offers the space, scenery, and shoreline you’ve been waiting for.

$800,000

Bozman Neavitt, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

$800,000

Experience modern living in the heart of St Michaels with this exquisitely renovated home. Completed in 2023, every aspect has been thoughtfully updated—from a chef’s kitchen and luxurious new bathrooms to pristine floors, a brand new roof, and new HVAC system. The expansive, open floorplan offers effortless flow for entertaining and everyday life. The main residence features three bedrooms and two and a half baths, complemented by a charming guest cottage with its own full bath—perfect for visitors or flexible use. Enjoy the convenience of being just steps away from boutique shops and acclaimed restaurants, making this home an unparalleled in-town retreat.

4 Beds ⋅ 4 Baths

Experience modern living in the heart of St Michaels with this exquisitely renovated home. Completed in 2023, every aspect has been thoughtfully updated—from a chef’s kitchen and luxurious new bathrooms to pristine floors, a brand new roof, and new HVAC system. The expansive, open floorplan offers effortless flow for entertaining and everyday life. The main residence features three bedrooms and two and a half baths, complemented by a charming guest cottage with its own full bath—perfect for visitors or flexible use. Enjoy the convenience of being just steps away from boutique shops and acclaimed restaurants, making this home an unparalleled in-town retreat.

207 Seymour Ave, Saint Michaels

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

Selling Office: Non Subscribing Office.

$787,500

This stately and well-constructed brick/wood cape cod majestically sits on a prime corner lot in the extremely desirable community of Martingham. The ideal floor-plan features a main floor primary bedroom and 3 second floor guest bedrooms. Beautiful hardwood flooring, custom built-ins, fireplace, 2 story foyer, screened porch , deck, covered front porch, circular driveway with extra parking pad, an over-sized 2 car attached garage, granite countertops , formal dining room and an inviting great room off the kitchen are all outstanding features that highlight this home's perfect design and craftsman.

This stately and well-constructed brick/wood cape cod majestically sits on a prime corner lot in the extremely desirable community of Martingham. The ideal floor-plan features a main floor primary bedroom and 3 second floor guest bedrooms. Beautiful hardwood flooring, custom built-ins, fireplace, 2 story foyer, screened porch , deck, covered front porch, circular driveway with extra parking pad, an over-sized 2 car attached garage, granite countertops , formal dining room and an inviting great room off the kitchen are all outstanding features that highlight this home's perfect design and craftsman.

24420 Mallard, Saint Michaels

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

Selling Office: Weichert, REALTORS.

$785,000

Located in the sought-after Martingham community and close proximity to downtown Saint Michaels, 24822 Swan Road offers the perfect balance of privacy, convenience, and Eastern Shore charm. Designed for comfortable single-level living, the home features 3 bedrooms and 3 full baths, including a spacious primary suite with a walk-in closet and an updated en-suite bath. The main living area is open-concept and features a family room with wood burning fireplace, parquet oak flooring leading into the recently renovated kitchen which serves as the heart of the home, blending style and functionality for everyday living and entertaining. There is also a sunroom which flanks the back of the house offering plenty of natural light and access to the covered back deck. A standout feature is the large detached two-car garage with a fully finished, conditioned space above, adding an additional 1,200 square feet of living space and bringing the total finished living area to 3,600 square feet. A workshop space is attached to the back of the garage, along with an additional 12' x 16' storage shed, providing even more room for a tractor, garden equipment, or general storage. There are peaceful water views from the back porch, creating an ideal backdrop for morning coffee or relaxed evenings outdoors. Residents enjoy access to a community waterfront park with a kayak launch, right down the street. With a brand-new roof being installed (2026), public water and sewer, mature landscaping, and a location minutes from waterfront dining, marinas, boutiques, and golf, this property delivers both lifestyle and peace of mind. Whether you are seeking a full-time residence or a weekend retreat near the water, 24822 Swan Road is a rare opportunity to enjoy the very best of Saint Michaels living. See documents for full list of updates.

Located in the sought-after Martingham community and close proximity to downtown Saint Michaels, 24822 Swan Road offers the perfect balance of privacy, convenience, and Eastern Shore charm. Designed for comfortable single-level living, the home features 3 bedrooms and 3 full baths, including a spacious primary suite with a walk-in closet and an updated en-suite bath. The main living area is open-concept and features a family room with wood burning fireplace, parquet oak flooring leading into the recently renovated kitchen which serves as the heart of the home, blending style and functionality for everyday living and entertaining. There is also a sunroom which flanks the back of the house offering plenty of natural light and access to the covered back deck. A standout feature is the large detached two-car garage with a fully finished, conditioned space above, adding an additional 1,200 square feet of living space and bringing the total finished living area to 3,600 square feet. A workshop space is attached to the back of the garage, along with an additional 12' x 16' storage shed, providing even more room for a tractor, garden equipment, or general storage. There are peaceful water views from the back porch, creating an ideal backdrop for morning coffee or relaxed evenings outdoors. Residents enjoy access to a community waterfront park with a kayak launch, right down the street. With a brand-new roof being installed (2026), public water and sewer, mature landscaping, and a location minutes from waterfront dining, marinas, boutiques, and golf, this property delivers both lifestyle and peace of mind. Whether you are seeking a full-time residence or a weekend retreat near the water, 24822 Swan Road is a rare opportunity to enjoy the very best of Saint Michaels living. See documents for full list of updates.

24822 Swan Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Waterman Realty.

$775,000

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

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

9359 Martingham, Saint Michaels

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

Selling Office: Unrepresented.

$775,000

Grace and Gratitude perfectly describe this charming historic home on Grace Street in the heart of St. Michaels! Grace St. is one of the few streets in town that isn't a through street to traffic. It starts at Talbot St & "Restaurant Row" & ends at the waterfront & walking trail off San Domingo Creek. The cozy front porch & classic Eastern Shore red front door are a prelude to the delightful interior spaces within. Beautifully renovated to include a more traditional living room which flows into a large open floor plan for the family room & dining room. The designer inspired kitchen with breakfast bar opens to the dining room & is close to the backdoor that leads out to the relaxing 12x14 screened porch. The porch overlooks a magical backyard that is an oasis for nature & centered around an adorable Victorian shed. Beautifully finished hardwood floors, moldings & gingerbread staircase make this a magazine quality home! The 2nd floor bedrooms are each unique & comfortable. Many recent improvements include: encapsulated crawlspace, bathroom renovation, On demand hot water, backyard irrigation, fireplace tile surround, electric car charger & a hot tub that's negotiable. Enjoy classic St. Michaels & all it has to offer in the enchanting neighborhood of Grace Street!

Grace and Gratitude perfectly describe this charming historic home on Grace Street in the heart of St. Michaels! Grace St. is one of the few streets in town that isn't a through street to traffic. It starts at Talbot St & "Restaurant Row" & ends at the waterfront & walking trail off San Domingo Creek. The cozy front porch & classic Eastern Shore red front door are a prelude to the delightful interior spaces within. Beautifully renovated to include a more traditional living room which flows into a large open floor plan for the family room & dining room. The designer inspired kitchen with breakfast bar opens to the dining room & is close to the backdoor that leads out to the relaxing 12x14 screened porch. The porch overlooks a magical backyard that is an oasis for nature & centered around an adorable Victorian shed. Beautifully finished hardwood floors, moldings & gingerbread staircase make this a magazine quality home! The 2nd floor bedrooms are each unique & comfortable. Many recent improvements include: encapsulated crawlspace, bathroom renovation, On demand hot water, backyard irrigation, fireplace tile surround, electric car charger & a hot tub that's negotiable. Enjoy classic St. Michaels & all it has to offer in the enchanting neighborhood of Grace Street!

106 Grace St, Saint Michaels

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

Selling Office: TTR Sotheby's International Realty.

$699,000

Set in one of St. Michaels’ most sought-after waterfront communities, this 3-bedroom, 3-bath Colonial offers a formal dining room, sitting room, living room with gas fireplace and built-ins, and a kitchen ready for your updates. In very good condition with solid construction, the home also includes a 2-car garage. An excellent opportunity to customize in a premier location, just minutes from historic downtown St. Michaels, waterfront dining, boutique shops, and marinas.

Set in one of St. Michaels’ most sought-after waterfront communities, this 3-bedroom, 3-bath Colonial offers a formal dining room, sitting room, living room with gas fireplace and built-ins, and a kitchen ready for your updates. In very good condition with solid construction, the home also includes a 2-car garage. An excellent opportunity to customize in a premier location, just minutes from historic downtown St. Michaels, waterfront dining, boutique shops, and marinas.

9235 Martingham Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Realty.

$685,000

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

4 Beds ⋅ 4 Baths

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

24977 Back Creek Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhanced with numerous upgrades. The owners added luxury vinyl plank flooring to the second level, Hunter Douglas plantation shutters with independent top and bottom operation, recessed lighting upstairs, and a high-end full-size Electrolux washer and dryer. Additional features include a smart home system with Nest locks, thermostats, doorbell camera, and smoke detectors, as well as an inground lawn irrigation system. Outdoors, the private backyard has been beautifully finished with professional landscaping, privacy fencing, and a Techno-Bloc custom paver patio. A welcoming front porch with flower boxes and rocking chairs sets the tone. Inside, the main level offers a cozy front foyer/den that opens to a spacious great room with living, dining, and kitchen areas. The gourmet kitchen boasts quartz countertops, a large island, gas range, pantry, and pendant lighting, with sliding doors that lead directly to the rear yard retreat. Upstairs, you’ll find four bedrooms and two full baths, including a primary suite with its own private bath. Set at the end of a non-through street just one block from the heart of St. Michaels, the location is ideal. Enjoy quiet evenings on the porch, gatherings in the backyard, or a few short blocks into town and the waterfront. From here, you can access shops, dining, the Chesapeake Bay Maritime Museum, and seasonal events. Even the town ice cream shop is only a few blocks away. Whether relaxing at home or exploring everything St. Michaels has to offer, this property provides the perfect blend of comfort, convenience, and small-town charm. Move-in ready and truly immaculate!

$675,000

This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhanced with numerous upgrades. The owners added luxury vinyl plank flooring to the second level, Hunter Douglas plantation shutters with independent top and bottom operation, recessed lighting upstairs, and a high-end full-size Electrolux washer and dryer. Additional features include a smart home system with Nest locks, thermostats, doorbell camera, and smoke detectors, as well as an inground lawn irrigation system. Outdoors, the private backyard has been beautifully finished with professional landscaping, privacy fencing, and a Techno-Bloc custom paver patio. A welcoming front porch with flower boxes and rocking chairs sets the tone. Inside, the main level offers a cozy front foyer/den that opens to a spacious great room with living, dining, and kitchen areas. The gourmet kitchen boasts quartz countertops, a large island, gas range, pantry, and pendant lighting, with sliding doors that lead directly to the rear yard retreat. Upstairs, you’ll find four bedrooms and two full baths, including a primary suite with its own private bath. Set at the end of a non-through street just one block from the heart of St. Michaels, the location is ideal. Enjoy quiet evenings on the porch, gatherings in the backyard, or a few short blocks into town and the waterfront. From here, you can access shops, dining, the Chesapeake Bay Maritime Museum, and seasonal events. Even the town ice cream shop is only a few blocks away. Whether relaxing at home or exploring everything St. Michaels has to offer, this property provides the perfect blend of comfort, convenience, and small-town charm. Move-in ready and truly immaculate!

408 Spinnaker Ln, Saint Michaels

Listing courtesy of Northrop Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

$640,000

This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth of July fireworks and thirsty Thursday with your new neighbors. Less than 3 miles to downtown St. Michaels Fine Dining and Shopping. MORE PHOTOS TO COME.

This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth of July fireworks and thirsty Thursday with your new neighbors. Less than 3 miles to downtown St. Michaels Fine Dining and Shopping. MORE PHOTOS TO COME.

24555 Deepwater Pt, Saint Michaels

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

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

24561 Deepwater Point Dr, Saint Michaels

$620,000

Select photos have been virtually staged to help visualize room layout and design possibilities. Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bath rancher features a light-filled, easy-flow floorplan with two ensuite bedrooms for added privacy and versatility. The home offers a garage and separate laundry room and opens to a charming backyard deck - ideal for morning coffee or evening gatherings. The spacious backyard provides ample room for a pool, enhancing the home's outdoor living potential. Comfortable, functional and perfectly suited for enjoying the Eastern Shore lifestyle.

Select photos have been virtually staged to help visualize room layout and design possibilities. Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bath rancher features a light-filled, easy-flow floorplan with two ensuite bedrooms for added privacy and versatility. The home offers a garage and separate laundry room and opens to a charming backyard deck - ideal for morning coffee or evening gatherings. The spacious backyard provides ample room for a pool, enhancing the home's outdoor living potential. Comfortable, functional and perfectly suited for enjoying the Eastern Shore lifestyle.

24561 Deepwater Point Dr, Saint Michaels

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

Selling Office: RE/MAX Executive.

$610,000

This is a rare chance to secure meaningful savings and a beautiful home in one of the Eastern Shore’s most desirable communities. Welcome to Martingham—home to the newly redesigned Pete Dye course, The Links at Perry Cabin, and just minutes from the heart of historic St. Michaels. Enjoy world-class dining, boutique shopping, and waterfront charm, all right at your fingertips. Set on 1.13 open acres with a tree-lined backdrop for privacy, this 3BR/2.5BA Colonial offers the space, setting, and lifestyle buyers are searching for. Inside, you’ll find a bright and spacious floor plan, an updated island kitchen, and a large family room featuring a wood-burning fireplace and beautiful beam ceiling. Upstairs, the generously sized primary suite includes a private balcony overlooking the backyard—a perfect retreat. Two additional oversized bedrooms offer flexibility for guests, office space, or hobbies. Outdoor living shines here: a large deck flows to the fire pit and expansive, level backyard—ideal for gatherings, relaxing, or simply enjoying nature. With its incredible location, valuable seller credit, and inviting living spaces, this home is an exceptional opportunity. Don’t miss your chance to tour it and experience the Martingham lifestyle for yourself.

This is a rare chance to secure meaningful savings and a beautiful home in one of the Eastern Shore’s most desirable communities. Welcome to Martingham—home to the newly redesigned Pete Dye course, The Links at Perry Cabin, and just minutes from the heart of historic St. Michaels. Enjoy world-class dining, boutique shopping, and waterfront charm, all right at your fingertips. Set on 1.13 open acres with a tree-lined backdrop for privacy, this 3BR/2.5BA Colonial offers the space, setting, and lifestyle buyers are searching for. Inside, you’ll find a bright and spacious floor plan, an updated island kitchen, and a large family room featuring a wood-burning fireplace and beautiful beam ceiling. Upstairs, the generously sized primary suite includes a private balcony overlooking the backyard—a perfect retreat. Two additional oversized bedrooms offer flexibility for guests, office space, or hobbies. Outdoor living shines here: a large deck flows to the fire pit and expansive, level backyard—ideal for gatherings, relaxing, or simply enjoying nature. With its incredible location, valuable seller credit, and inviting living spaces, this home is an exceptional opportunity. Don’t miss your chance to tour it and experience the Martingham lifestyle for yourself.

24749 Swan Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$600,000

NEW PRICE — EXCEPTIONAL VALUE IN DESIRABLE MARTINGHAM! Welcome to 9206 Martingham Drive, a truly distinctive contemporary residence offering spacious living with 4 bedrooms, 2 full and one half bathrooms, abundant natural light, and timeless architectural character in one of Saint Michaels' most sought-after communities. Competitively priced and thoughtfully designed, this unique home features an open floor plan, soaring vaulted ceilings, exposed beams, and expansive east- and west-facing windows that fill the home with natural light while capturing stunning sunrises and sunsets throughout the year. A wood-burning fireplace with a high-efficiency insert and circulating fan creates a warm and inviting focal point, while three dedicated HVAC systems and energy-efficient double-pane windows provide year-round comfort and efficiency. This exceptional property is nestled within the desirable Martingham community, known for its scenic surroundings, golf course lifestyle, and proximity to everything Saint Michaels has to offer. Less than five minutes from downtown Saint Michaels, residents enjoy easy access to waterfront attractions, marinas, boutique shopping, dining, and the very best of Eastern Shore living. The generous living spaces are ideal for both everyday living and entertaining. A spacious two-car garage with built-in shelving provides excellent storage, while the expansive deck—accessible from the sunroom, kitchen, and garage—seamlessly extends the living space outdoors, creating the perfect setting for relaxing or hosting guests. The spacious primary suite on the main floor offers a private retreat, featuring dual walk-in closets and brand-new carpeting installed in 2024. Encapsulated crawlspace for improved moisture control and energy efficiency. Recent capital improvements completed in 2024 include a new roof and gutter system, totaling more than $90,000 in upgrades. Work with our preferred lender to get $2,500 lender credit towards your closing costs! Whether you're searching for a primary residence, a weekend retreat, or an investment opportunity, this one-of-a-kind property delivers exceptional value, space, and location. Don't miss your chance to own a special home in one of Saint Michaels' premier golf course communities.

NEW PRICE — EXCEPTIONAL VALUE IN DESIRABLE MARTINGHAM! Welcome to 9206 Martingham Drive, a truly distinctive contemporary residence offering spacious living with 4 bedrooms, 2 full and one half bathrooms, abundant natural light, and timeless architectural character in one of Saint Michaels' most sought-after communities. Competitively priced and thoughtfully designed, this unique home features an open floor plan, soaring vaulted ceilings, exposed beams, and expansive east- and west-facing windows that fill the home with natural light while capturing stunning sunrises and sunsets throughout the year. A wood-burning fireplace with a high-efficiency insert and circulating fan creates a warm and inviting focal point, while three dedicated HVAC systems and energy-efficient double-pane windows provide year-round comfort and efficiency. This exceptional property is nestled within the desirable Martingham community, known for its scenic surroundings, golf course lifestyle, and proximity to everything Saint Michaels has to offer. Less than five minutes from downtown Saint Michaels, residents enjoy easy access to waterfront attractions, marinas, boutique shopping, dining, and the very best of Eastern Shore living. The generous living spaces are ideal for both everyday living and entertaining. A spacious two-car garage with built-in shelving provides excellent storage, while the expansive deck—accessible from the sunroom, kitchen, and garage—seamlessly extends the living space outdoors, creating the perfect setting for relaxing or hosting guests. The spacious primary suite on the main floor offers a private retreat, featuring dual walk-in closets and brand-new carpeting installed in 2024. Encapsulated crawlspace for improved moisture control and energy efficiency. Recent capital improvements completed in 2024 include a new roof and gutter system, totaling more than $90,000 in upgrades. Work with our preferred lender to get $2,500 lender credit towards your closing costs! Whether you're searching for a primary residence, a weekend retreat, or an investment opportunity, this one-of-a-kind property delivers exceptional value, space, and location. Don't miss your chance to own a special home in one of Saint Michaels' premier golf course communities.

9206 Martingham Dr, Saint Michaels

Listing courtesy of Samson Properties. Contact:

Selling Office: Benson & Mangold, LLC.

$539,500

Situated on a corner lot just minutes from downtown St. Michaels, this 3-bedroom, 2-bath home offers easy access to local shops, restaurants, and the Maritime Museum. Inside, the living room is filled with natural light from a large bay window and features LVP flooring, recessed lighting, and updated fixtures throughout. The kitchen and dining area provide an open, functional layout with direct access to the backyard through sliding glass doors. Both bathrooms have been remodeled, and additional updates include new electrical outlets and switches, a 2024 electric panel, HVAC (2025), and a 2026 hot water heater. Outside, the fenced yard includes a patio, sodded lawn, professional landscaping, and an irrigation system. A 14’x20’ insulated shed with electric and heating/air offers flexible use as a workshop or studio. The home also features a newer roof, siding, gutters, and downspouts (2 years), plus a 5-year-old encapsulated crawlspace with sump pump and dehumidifier. Complete with a private driveway and well-maintained exterior, this property combines convenience, updates, and location.

Situated on a corner lot just minutes from downtown St. Michaels, this 3-bedroom, 2-bath home offers easy access to local shops, restaurants, and the Maritime Museum. Inside, the living room is filled with natural light from a large bay window and features LVP flooring, recessed lighting, and updated fixtures throughout. The kitchen and dining area provide an open, functional layout with direct access to the backyard through sliding glass doors. Both bathrooms have been remodeled, and additional updates include new electrical outlets and switches, a 2024 electric panel, HVAC (2025), and a 2026 hot water heater. Outside, the fenced yard includes a patio, sodded lawn, professional landscaping, and an irrigation system. A 14’x20’ insulated shed with electric and heating/air offers flexible use as a workshop or studio. The home also features a newer roof, siding, gutters, and downspouts (2 years), plus a 5-year-old encapsulated crawlspace with sump pump and dehumidifier. Complete with a private driveway and well-maintained exterior, this property combines convenience, updates, and location.

113 Gloria, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$530,000

Rare opportunity to own a commercial property in the heart of historic downtown St Michaels. Situated on a prime, high-visibility corner lot, this turn-of-the-century building offers approximately 2,100+/- square feet of space with strong foot traffic and excellent exposure. Off-street parking and climate controlled outbuilding for additional storage adds convenience. Enjoy flexibility for a variety of uses.

312 S Talbot, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$528,000

This handsome home is nestled in the trees on a quiet cul de sac in Rio Vista. This popular neighborhood is five minutes from historic St. Michaels and offers public sewer and water with no town taxes. Rio Vista has a waterfront picnic area and boat slips for rent to residents for $225 per slip. This home has been very nicely maintained by the original owner. It offers one-level living, with a primary suite and laundry on the first floor. The kitchen overlooks the breakfast area and family room, which features a vaulted ceiling and gas fireplace. Upstairs are two additional bedrooms plus an office that could be a fourth bedroom (no closet). An attached garage adds to the convenience.

This handsome home is nestled in the trees on a quiet cul de sac in Rio Vista. This popular neighborhood is five minutes from historic St. Michaels and offers public sewer and water with no town taxes. Rio Vista has a waterfront picnic area and boat slips for rent to residents for $225 per slip. This home has been very nicely maintained by the original owner. It offers one-level living, with a primary suite and laundry on the first floor. The kitchen overlooks the breakfast area and family room, which features a vaulted ceiling and gas fireplace. Upstairs are two additional bedrooms plus an office that could be a fourth bedroom (no closet). An attached garage adds to the convenience.

228 Tyler Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$480,000

Welcome to your future home in the heart of St. Michaels! Currently under construction, this brand-new rancher will showcase modern design and quality craftsmanship throughout. Featuring 3 spacious bedrooms and 2 full bathrooms, this single-level home is designed for comfort and convenience. Step inside to find beautiful LVP flooring, a large trim package, and a bright open layout. The kitchen will be appointed with quartz countertops and stylish finishes, making it the perfect space for cooking and entertaining. This home also comes with the peace of mind of a 1-year builder-backed warranty. Please note: no alterations or customizations will be made until after settlement. Don’t miss the opportunity to own a new construction home in the highly desirable St. Michaels area—close to shops, dining, and the charm of the Chesapeake Bay.

Welcome to your future home in the heart of St. Michaels! Currently under construction, this brand-new rancher will showcase modern design and quality craftsmanship throughout. Featuring 3 spacious bedrooms and 2 full bathrooms, this single-level home is designed for comfort and convenience. Step inside to find beautiful LVP flooring, a large trim package, and a bright open layout. The kitchen will be appointed with quartz countertops and stylish finishes, making it the perfect space for cooking and entertaining. This home also comes with the peace of mind of a 1-year builder-backed warranty. Please note: no alterations or customizations will be made until after settlement. Don’t miss the opportunity to own a new construction home in the highly desirable St. Michaels area—close to shops, dining, and the charm of the Chesapeake Bay.

216 Brooks, Saint Michaels

Listing courtesy of LPT Realty, LLC. Contact: