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Recently Sold Homes in 21663

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  • 109 W Chew Ave, Saint Michaels, MD 21663
    109 W Chew Ave, Saint Michaels, MD 21663
    109 W Chew Ave, Saint Michaels, MD 21663
    /39

    $662,500 Sold Jul 18, 2025

    • 1,824 Sq Ft
    • $363/SF
    • 21 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1920

    109 W Chew Ave, Saint Michaels, MD 21663

    Located in a prime location this 3-bedroom home is full of potential. Featuring a spacious yard, detached garage/workshop, and a breezy screened porch, it’s ready for your vision. Inside, you’ll find hardwood flooring, a beautiful formal dining room, den / office at the rear, and a eat-in kitchen with character-rich beamed ceilings. The second floor offers a large primary bedroom with private

    Barbara Watkins Benson & Mangold, LLC

    109 W Chew Ave, Saint Michaels, MD 21663
  • 106C Conner St, Saint Michaels, MD 21663
    106C Conner St, Saint Michaels, MD 21663
    106C Conner St, Saint Michaels, MD 21663
    /31

    $399,000 Sold Jul 18, 2025

    • 1,080 Sq Ft
    • $369/SF
    • 157 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1998

    106C Conner St, Saint Michaels, MD 21663

    Charming move in ready cottage in the center of St. Michaels. Enjoy very low electric bills due to 2 year old solar panels on the roof. This is an exceptional offering with a modern kitchen, equipped with 5-burner gas stove, white upgraded cabinetry and stainless steel appliances. Bright and open living space plus a dining area off the kitchen and an updated bathroom with walk in, custom glass

    Carolina Barksdale Benson & Mangold, LLC

    106C Conner St, Saint Michaels, MD 21663
  • 103 W Marengo St, Saint Michaels, MD 21663
    103 W Marengo St, Saint Michaels, MD 21663
    103 W Marengo St, Saint Michaels, MD 21663
    /39

    $545,000 Sold Jul 11, 2025

    • 1,209 Sq Ft
    • $451/SF
    • 51 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1940

    103 W Marengo St, Saint Michaels, MD 21663

    Quintessential St. Michaels Charm! Nestled in the heart of this historic and picturesque waterfront town, this adorable cedar shake home is straight out of Nantucket! With two bedrooms, one and a half baths, and classic coastal curb appeal, this home sits on a generous fenced lot backing up to alley way—perfect for outdoor entertaining, gardening, or simply soaking in the Chesapeake breeze.

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    103 W Marengo St, Saint Michaels, MD 21663
  • 400 Railroad Ave, Saint Michaels, MD 21663
    400 Railroad Ave, Saint Michaels, MD 21663
    400 Railroad Ave, Saint Michaels, MD 21663
    /35

    $505,000 Sold Jul 09, 2025

    • 1,674 Sq Ft
    • $302/SF
    • 62 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    400 Railroad Ave, Saint Michaels, MD 21663

    Nestled on a desirable corner lot in the historic waterfront town of St. Michaels, this 1930 bungalow blends classic architecture with modern comforts. Ideally located just a short distance from the Chesapeake Bay Maritime Museum, shops, restaurants, and the harbor, this home offers the best of in-town living. A spacious front porch welcomes you - perfect for morning coffee or casual

    Monica Penwell TTR Sotheby's International Realty

    400 Railroad Ave, Saint Michaels, MD 21663
  • 7896 Hart Glen Ct, Saint Michaels, MD 21663
    7896 Hart Glen Ct, Saint Michaels, MD 21663
    7896 Hart Glen Ct, Saint Michaels, MD 21663
    /70

    $795,000 Sold Jun 30, 2025

    • 3,038 Sq Ft
    • $262/SF
    • 14 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    7896 Hart Glen Ct, Saint Michaels, MD 21663

    Located at the end of a quiet cul-de-sac in the desirable Back Creek Landing neighborhood of St. Michaels, Maryland, this beautifully maintained home offers privacy, quality upgrades, and a fantastic Eastern Shore lifestyle. The large, inviting front porch sets the tone as you arrive. Step inside and you are welcomed by a warm, light-filled interior that immediately feels like home. The floor

    Kathleen Coale Benson & Mangold, LLC

    7896 Hart Glen Ct, Saint Michaels, MD 21663
  • 106 Boundary Ln, Saint Michaels, MD 21663
    106 Boundary Ln, Saint Michaels, MD 21663
    106 Boundary Ln, Saint Michaels, MD 21663
    /58

    $575,000 Sold Jun 27, 2025

    • 1,490 Sq Ft
    • $386/SF
    • 32 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1997

    106 Boundary Ln, Saint Michaels, MD 21663

    Nestled in the heart of St. Michaels, this beautifully maintained one-level home offers 2–3 bedrooms and 2 full bathrooms. A welcoming stone front porch leads to a foyer that opens into a bright, airy interior filled with natural light and wide plank wood floors throughout. The updated kitchen features quartz countertops, a farmhouse sink, tile backsplash and stainless steel appliances. Just off

    Kim Crouch Ozman Benson & Mangold, LLC

    106 Boundary Ln, Saint Michaels, MD 21663
  • 7171 Drum Point Rd, Saint Michaels, MD 21663
    7171 Drum Point Rd, Saint Michaels, MD 21663
    7171 Drum Point Rd, Saint Michaels, MD 21663
    /70

    $1,840,000 Sold Jun 25, 2025

    • 3,000 Sq Ft
    • $613/SF
    • 11 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1969

    7171 Drum Point Rd, Saint Michaels, MD 21663

    Your own private resort in St Michael’s Maryland!! This one has it all and then some! Dock with boat lift, swimming pool, tennis court, 4 to 5 bedrooms, beautiful baths, hardwood floors. Within the last five years the owners have put on a new roof and dormers, redone the kitchen, encapsulated the crawlspace, installed a boat lift, replaced the boiler and painted the exterior. Don’t miss your

    Larry Brennan TTR Sotheby's International Realty

    7171 Drum Point Rd, Saint Michaels, MD 21663
  • 9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    /41

    $435,000 Sold Jun 23, 2025

    • 1,752 Sq Ft
    • $248/SF
    • 33 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663

    DESIRABLE END UNIT TOWNHOME WITH 1ST FLOOR BEDROOM AND BATH, VERY PRIVATE VIEW OF THE GOLF COURSE PLANTINGS AND A SMALL WATER VIEW FROM THE 2ND FLOOR DECK OFF THE PRIMARY BEDROOM.THE KITCHEN HAS BEEN RENOVATED, WHITE CABINETS WITH STONE COUNTERTOPS, A LARGE GLASS DOOR OPENS TO THE TILE FLOORED SUN ROOM FROM THE KITCHEN AND FROM THE DINING ROOM, LETTING THE LIGHT FILL THE UNIT. THE SECOND

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
  • 9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663
    9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663
    9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663
    /65

    $335,000 Sold Jun 20, 2025

    • 1,800 Sq Ft
    • $186/SF
    • 221 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1973

    9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663

    Nestled amongst the prestigious ‘Links at Perry Cabin Golf Course,’ this desirable Martingham condo features 2 bedrooms and 2.5 baths. The home opens to a foyer and flows into a spacious living and dining area, complete with laminate wood floors and a wood-burning fireplace. The sunroom offers versatile living space, perfect as an office, sitting room or additional relaxation area and opens to a

    Kim Crouch Ozman Benson & Mangold, LLC

    9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663
  • 9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    /60

    $480,000 Sold Jun 19, 2025

    • 1,800 Sq Ft
    • $267/SF
    • 9 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1996

    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663

    This stunning three-bedroom, three-bath home is, without question, the nicest townhome in the very desirable Martingham Quail Hollow community. The home has been extensively upgraded with exquisite finishes, and it enjoys a beautiful, landscaped setting that backs onto the Links at Perry Cabin Golf Course. The spacious great room opens to the charming, landscaped patio with an automatic awning

    Eugene Smith TTR Sotheby's International Realty

    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
  • 23686 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23686 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23686 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    /50

    $3,300,000 Sold Jun 06, 2025

    • 4,090 Sq Ft
    • $807/SF
    • 4 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1998

    23686 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    You'll feel like you're on a continuous vacation in this spectacular 4-bedroom, 4.5 bath coastal style home that features breathtaking, panoramic views of Broad Creek and only 2.5 miles from charming historic St. Michaels. A setting that is truly "vacation like" with a stunning waterside pool/spa complex, outdoor fireplace, outdoor room with automatic screens, a large hardscaped patio, 300 feet

    Eugene Smith TTR Sotheby's International Realty

    23686 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
  • 24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
    /55

    $389,900 Sold May 28, 2025

    • 1,296 Sq Ft
    • $301/SF
    • 14 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1978

    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663

    Bright, open, and beautifully updated, this one-level condo offers spectacular views of the prestigious Links at Perry Cabin golf course. Featuring 2 bedrooms and 2 baths, this home boasts an inviting living room with wood floors, a cozy gas fireplace, crown molding and plantation shutters. The updated kitchen features white cabinetry, matte granite countertops, a stylish tile backsplash, a

    Kim Crouch Ozman Benson & Mangold, LLC

    24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663
  • 24981 Back Creek Dr, Saint Michaels, MD 21663
    24981 Back Creek Dr, Saint Michaels, MD 21663
    24981 Back Creek Dr, Saint Michaels, MD 21663
    /47

    $765,000 Sold May 19, 2025

    • 3,166 Sq Ft
    • $242/SF
    • 4 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2006

    24981 Back Creek Dr, Saint Michaels, MD 21663

    Fabulous 5 bedrooms, 3.5 bath home with sought after floorplan, a spacious screened porch and deck located in the desirable Back Creek Landing neighborhood on the Easton side of St. Michaels with 40 acres of community areas, trails, ponds, and water access to San Domingo Creek. The wooded rear yard offers privacy with easy access to trails, community areas, and water access kayak pier. The

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24981 Back Creek Dr, Saint Michaels, MD 21663
  • 104 W Chew Ave, Saint Michaels, MD 21663
    104 W Chew Ave, Saint Michaels, MD 21663
    104 W Chew Ave, Saint Michaels, MD 21663
    /18

    $1,310,000 Sold May 16, 2025

    • 2,654 Sq Ft
    • $494/SF
    • 2 Beds
    • 2 Baths
    • Built 1900

    104 W Chew Ave, Saint Michaels, MD 21663

    Sited on an unusually spacious 9000 square foot lot, this beautifully-restored c. 1900 home combines the best of historic charm with a modern, open floor plan. With heart pine floors throughout, three fireplaces, and lots of light, the home is warm and welcoming. During renovation, the house was raised and a new foundation was put in place. The yard is extensively landscaped and there is a large

    datacorrect BrightMLS Non Subscribing Office

    104 W Chew Ave, Saint Michaels, MD 21663
  • 103 N Harbor Rd, Saint Michaels, MD 21663
    103 N Harbor Rd, Saint Michaels, MD 21663
    103 N Harbor Rd, Saint Michaels, MD 21663
    /72

    $2,325,000 Sold May 09, 2025

    • 3,732 Sq Ft
    • $623/SF
    • 6 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1954

    103 N Harbor Rd, Saint Michaels, MD 21663

    Breathtaking views of the Miles River and Chesapeake Bay Maritime Museum. Once in a lifetime opportunity to buy a solidly built home on almost an acre, within a few short blocks of downtown historic St. Michaels. Located on the harbor and close to restaurants and shopping. This 4 bedroom home is currently undergoing renovations. The kitchen has cherry cabinets, Wolf appliances, Fisher&

    Barbara Watkins Benson & Mangold, LLC

    103 N Harbor Rd, Saint Michaels, MD 21663
  • 226 North St, Saint Michaels, MD 21663
    226 North St, Saint Michaels, MD 21663
    226 North St, Saint Michaels, MD 21663
    /12

    $140,000 Sold May 09, 2025

    • Land
    • 0.21 Acre
    • $666,667 per Acre
    • 247 Days On Market

    226 North St, Saint Michaels, MD 21663

    40K PRICE REDUCTION! New Survey and Setback Requirements in document section of listing! Ready to build your custom home in the beautiful town of St. Michaels! PROPERTY IS UNDER R-1 and ALLOWS FOR A DUPLEX IF DESIRED. This is a larger lot, over 1/5 of an acre. Enjoy all the benefits of living in town, walk to the harbor, shops, restaurants, nature trail, library, ball park, community center

    Jennifer Pogoda Chesapeake Bay Real Estate Plus, LLC

    226 North St, Saint Michaels, MD 21663
  • 919 Riverview Terrace, Saint Michaels, MD 21663
    919 Riverview Terrace, Saint Michaels, MD 21663
    919 Riverview Terrace, Saint Michaels, MD 21663
    /40

    $739,000 Sold May 02, 2025

    • 2,948 Sq Ft
    • $251/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    919 Riverview Terrace, Saint Michaels, MD 21663

    Located just outside the Town limits of St. Michaels on a very popular street (Riverview Terrace), this attractive 2,948 sq. ft. home was constructed in 2005. Outstanding floor plan is a combination of open and traditional, with a large kitchen/breakfast room/family room combination w/vaulted ceiling and lots of glass to capture the views across the private, landscaped back yard. The downstairs

    Tom Crouch Benson & Mangold, LLC

    919 Riverview Terrace, Saint Michaels, MD 21663
  • 315 Dodson Ave, Saint Michaels, MD 21663
    315 Dodson Ave, Saint Michaels, MD 21663
    315 Dodson Ave, Saint Michaels, MD 21663
    /14

    $226,000 Sold Apr 30, 2025

    • 1,000 Sq Ft
    • $226/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1981

    315 Dodson Ave, Saint Michaels, MD 21663

    Do not miss this rancher style home in the town of St Michaels. This home offers over 1000 sq ft of living space and has an abundance of natural light. Featuring spacious living room that leads to the kitchen-dining combo and appliances, 3 bedrooms that provide privacy and relaxation, and a full bathroom. The outdoor space displays practical features such as a storage shed, driveway and widefront

    Gina Gargeu Century 21 Downtown

    315 Dodson Ave, Saint Michaels, MD 21663
  • 24256 Oakwood Park Rd, Saint Michaels, MD 21663
    24256 Oakwood Park Rd, Saint Michaels, MD 21663
    /2

    $1,500,000 Sold Apr 29, 2025

    • 2,702 Sq Ft
    • $555/SF
    • 18 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1954

    24256 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to your private retreat just moments to the charming, historic town of St. Michaels. This stunning, light- filled home boasts a perfect blend of elegance and comfort, complete with thoughtfully designed custom details throughout. Magnificent views overlooking San Domingo Creek from every room. Enjoy a waterside first floor primary suite with totally renovated ensuite bathroom with quartz

    Barbara Watkins Benson & Mangold, LLC

    24256 Oakwood Park Rd, Saint Michaels, MD 21663
  • 113 W Chestnut St, Saint Michaels, MD 21663
    113 W Chestnut St, Saint Michaels, MD 21663
    113 W Chestnut St, Saint Michaels, MD 21663
    /75

    $1,100,000 Sold Apr 24, 2025

    • 2,548 Sq Ft
    • $432/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1817

    113 W Chestnut St, Saint Michaels, MD 21663

    Nestled in the heart of the historic town of St. Michaels, this enchanting 3-bedroom, 2-1/2 baths historic home offers the perfect blend of modern comfort and timeless charm. Do not miss this rare opportunity to own a piece of St. Michaels' rich history. Whether you are seeking a weekend getaway or a forever home, 113 W Chestnut Street is a true gem on one of the most desirable and beautiful

    Carolina Barksdale Benson & Mangold, LLC

    113 W Chestnut St, Saint Michaels, MD 21663
  • 24393 Widgeon Place, Saint Michaels, MD 21663
    24393 Widgeon Place, Saint Michaels, MD 21663
    24393 Widgeon Place, Saint Michaels, MD 21663
    /53

    $750,000 Sold Mar 28, 2025

    • 2,459 Sq Ft
    • $305/SF
    • 11 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1973

    24393 Widgeon Place, Saint Michaels, MD 21663

    ONE STORY LIVING ON PARK LIKE SETTING CORNER LOT SURROUNDED BY THE PRESTIGEOUS LINKS AT PERRY CABIN AND JUST 5 MINUTES TO HISTORIC ST MICHAELS.THIS HOME FEATURES LOTS OF WINDOWS , TREES FILTERING THE BRIGHT SUNLIGHT, OPEN THE SLIDING DOOR AND STEP OUT TO SIT BY THE FIRE PIT AND ENJOY THE BEAUTIFUL LANDSCAPED GROUNDS. THERE IS A 4 SEASON SUNROOM TO ENJOY THE OUTDOORS IN COLDER WEATHER. THE

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24393 Widgeon Place, Saint Michaels, MD 21663
  • 402 Railroad Ave, Saint Michaels, MD 21663
    402 Railroad Ave, Saint Michaels, MD 21663
    402 Railroad Ave, Saint Michaels, MD 21663
    /50

    $875,000 Sold Mar 28, 2025

    • 2,450 Sq Ft
    • $357/SF
    • 3 Beds
    • 3 Baths
    • Built 1900

    402 Railroad Ave, Saint Michaels, MD 21663

    FABULOUS IN TOWN SPACIOUS CORNER LOT PROVIDES MANY EXPANSION OPTIONS. FULLY FENCED BACKYARD , LARGE INGROUND POOL, HOT TUB, AL FRESCO DINING ON THE PATIO WITH FIREPIT. 1 CAR GARAGE WITH STORAGE OPTIONS, MULTIPLE OFF STREET PARKING SPACES, PRIVATE GRAVEL DRIVEWAY, RAISED GARDEN BEDS.VERY UNIQUE OPPORTUNITY TO OWN THIS LIGHT FILLED HISTORIC VICTORIAN WITH 9 FOOT CEILINGS ON THE 1 ST FLOOR AND

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    402 Railroad Ave, Saint Michaels, MD 21663
  • 9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    /37

    $472,500 Sold Mar 18, 2025

    • 1,800 Sq Ft
    • $262/SF
    • 18 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1995

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663

    Located in the highly desirable Martingham community of Quail Hollow, this beautifully renovated 3-bedroom, 3-bath townhome is move-in ready after extensive updates between 2022 and 2024. The main level features stunning wood flooring throughout, a spacious great room with a gas fireplace, built-ins, and access to a peaceful rear patio that backs to open space.. The completely remodeled kitchen

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • 7930 Church Neck Rd, Saint Michaels, MD 21663
    7930 Church Neck Rd, Saint Michaels, MD 21663
    7930 Church Neck Rd, Saint Michaels, MD 21663
    /44

    $1,833,000 Sold Mar 14, 2025

    • 2,670 Sq Ft
    • $687/SF
    • 1 Day On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1982

    7930 Church Neck Rd, Saint Michaels, MD 21663

    Welcome to "Point of View" – Your Waterfront Sanctuary in St. Michaels, MD! Discover the perfect blend of elegance and tranquility in this stunning coastal-style home nestled on 4+/- acres with 220 feet of riprapped shoreline along picturesque Broad Creek. Boasting breathtaking southwesterly views and designed to capture the essence of serene waterfront living, this property is a rare gem in a

    Monica Penwell TTR Sotheby's International Realty

    7930 Church Neck Rd, Saint Michaels, MD 21663
  • 8080 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8080 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8080 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /80

    $900,000 Sold Feb 28, 2025

    • 5,869 Sq Ft
    • $153/SF
    • 9 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1960

    8080 Bozman Neavitt Rd, Saint Michaels, MD 21663

    SELLER TO REVIEW ALL OFFERS ON JANUARY 25, 20205 AT 6 O'CLOCK Charming WaterfrontProperty with Established Vacation Rental BusinessDiscover an extraordinary opportunity with this 1.5+ acre waterfront property on Harris Creek. Featuring eight fully equipped, one-bedroom cottages and a spacious main house, this turn-key operation has been a successful vacation rental business for

    Mary Lapides Cummings & Co. Realtors

    8080 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 104 Mulberry St, Saint Michaels, MD 21663
    104 Mulberry St, Saint Michaels, MD 21663
    104 Mulberry St, Saint Michaels, MD 21663
    /72

    $1,295,000 Sold Feb 21, 2025

    • 1,938 Sq Ft
    • $668/SF
    • 3 Beds
    • 2.5 Baths
    • Built 1786

    104 Mulberry St, Saint Michaels, MD 21663

    Located in the heart of St. Michaels' Historic District, the "Keithley House," circa 1786, is one of the town's historic treasures. Records indicate the house was renovated and expanded between 1860 and 1870, when Victorian elements were incorporated, including a wonderful front porch. The house was extensively restored and updated in 2008, with care to preserve the 18th and 19th century charm.

    Tom Crouch Benson & Mangold, LLC

    104 Mulberry St, Saint Michaels, MD 21663
  • 0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663
    0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663
    0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663
    /6

    $685,000 Sold Feb 07, 2025

    • Land
    • 16 Acres
    • $42,653 per Acre
    • 16 Days On Market

    0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663

    Solitude Creek - 16 acres of beautiful pine forest offering seclusion and privacy within a short distance to St. Michaels. With 675 feet of shoreline on Solitude Creek with approximately four feet at mean low tide, this tidal waterway provides a sanctuary for wintering waterfowl. Previously perc approved for a 4 bedroom home.

    Coard Benson Benson & Mangold, LLC

    0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663
  • 9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    /25

    $880,000 Sold Feb 06, 2025

    • 4,102 Sq Ft
    • $215/SF
    • 8 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1992

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Exceptional Waterfront Living Near Historic St. Michaels. Discover a unique opportunity to own a stunning waterfront property situated on over 6 acres, just minutes from Historic St. Michaels and directly across from the prestigious Links at Perry Cabin Golf Course. This expansive 4,000 sq. ft. single-story residence is designed for both comfort and luxury. The thoughtfully designed floor plan

    Wink Cowee Benson & Mangold, LLC

    9171 Deepwater Point Rd, Saint Michaels, MD 21663
  • 9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663
    9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663
    9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663
    /28

    $395,000 Sold Feb 03, 2025

    • 1,800 Sq Ft
    • $219/SF
    • 119 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1973

    9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663

    Nestled in the desirable Martingham community and backing to the scenic 2nd hole at the Links of Perry Cabin, this charming 2-bedroom, 2.5-bathroom condo offers a perfect retreat for low-maintenance living. The open living and dining area, featuring a cozy wood-burning fireplace, flows seamlessly into the inviting sunroom, creating the ideal space for relaxation. The primary bedroom boasts a

    Chuck Mangold Benson & Mangold, LLC

    9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663
  • 1003 Riverview Terrace, Saint Michaels, MD 21663
    1003 Riverview Terrace, Saint Michaels, MD 21663
    1003 Riverview Terrace, Saint Michaels, MD 21663
    /50

    $2,600,000 Sold Jan 30, 2025

    • 4,320 Sq Ft
    • $602/SF
    • 3 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2006

    1003 Riverview Terrace, Saint Michaels, MD 21663

    Experience tranquil waterfront living in this stunning 4BR/4.5 BA home sited on .67 acres overlooking the Miles River. Built in 2006, this Craftsman-style home was thoughtfully designed by Lars Erickson and built by Don Foster to blend effortlessly with the beauty of the landscape. The exquisite architectural details are evident throughout and include vaulted ceilings, Australian Cypress

    Laura Carney TTR Sotheby's International Realty

    1003 Riverview Terrace, Saint Michaels, MD 21663
  • 202 Mulberry St, Saint Michaels, MD 21663
    202 Mulberry St, Saint Michaels, MD 21663
    202 Mulberry St, Saint Michaels, MD 21663
    /51

    $1,196,000 Sold Jan 21, 2025

    • 2,703 Sq Ft
    • $442/SF
    • 8 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1890

    202 Mulberry St, Saint Michaels, MD 21663

    Discover this charming historic home in the heart of St. Michaels, built circa 1890, where classic craftsmanship and timeless elegance come together. Starting with the expansive wrap-around porch, you can see this home is a traditional gem. Highlights of the home include 9ft. ceilings, hardwood floors throughout and original architectural details that define the craftsmanship. and charm. The

    Monica Penwell TTR Sotheby's International Realty

    202 Mulberry St, Saint Michaels, MD 21663
  • 7536 Quaker Neck Rd, Bozman, MD 21612
    7536 Quaker Neck Rd, Bozman, MD 21612
    7536 Quaker Neck Rd, Bozman, MD 21612
    /50

    $4,000,000 Sold Jan 21, 2025

    • 3,670 Sq Ft
    • $1090/SF
    • 33 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    7536 Quaker Neck Rd, Bozman, MD 21612

    Welcome to this private paradise on Maryland's Eastern Shore with a slip for two boats. Ideal for outdoor enthusiasts, with 1400' of views oriented towards the water. The residence features an open floor plan with a spacious living and separate dining area with a fireplace, leading to the gourmet kitchen. The main floor also offers two bedrooms and a full bathroom. Upstairs is a primary bedroom

    Danielle Naeve TTR Sotheby's International Realty

    7536 Quaker Neck Rd, Bozman, MD 21612
  • 0 Oakwood Park Rd, Saint Michaels, MD 21663
    0 Oakwood Park Rd, Saint Michaels, MD 21663
    0 Oakwood Park Rd, Saint Michaels, MD 21663
    /37

    $250,000 Sold Jan 14, 2025

    • Land
    • 6 Acres
    • $44,326 per Acre
    • 480 Days On Market

    0 Oakwood Park Rd, Saint Michaels, MD 21663

    Indulge in the allure of Eastern Shore living with this exquisite premium building site, situated in the esteemed Estate area of Oakwood Park. Just a stone's throw from the historic charm of downtown St. Michaels, this parcel offers a serene escape surrounded by nature's beauty. Picture-perfect views of San Domingo Creek adorn this tranquil lot, dotted with mature trees. Anticipate the

    Connie Loveland Benson & Mangold, LLC

    0 Oakwood Park Rd, Saint Michaels, MD 21663
  • 23857 Ebb Point Rd, Bozman, MD 21612
    23857 Ebb Point Rd, Bozman, MD 21612
    23857 Ebb Point Rd, Bozman, MD 21612
    /67

    $1,040,000 Sold Jan 03, 2025

    • 2,250 Sq Ft
    • $462/SF
    • 65 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1986

    23857 Ebb Point Rd, Bozman, MD 21612

    Nestled on 2.5+/- wooded acres along Broad Creek, this contemporary four-bedroom, two-and-a-half-bath Lindal Cedar Home offers stunning water views from most rooms. Relax on the expansive waterside deck or enjoy the serenity of the screened porch with skylights. Surrounded by mature trees, this private retreat is perfect for nature lovers, with frequent sightings of wildlife and birds. Inside,

    Jane Baker Benson & Mangold, LLC

    23857 Ebb Point Rd, Bozman, MD 21612
  • 107 Carpenter St, Saint Michaels, MD 21663
    107 Carpenter St, Saint Michaels, MD 21663
    107 Carpenter St, Saint Michaels, MD 21663
    /30

    $820,000 Sold Jan 02, 2025

    • 1,228 Sq Ft
    • $668/SF
    • 2 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1900

    107 Carpenter St, Saint Michaels, MD 21663

    Don't miss this St. Michaels gem! The perfect Captain's house in the ideal location. Situated in the heart of historic St. Michaels, it is in easy walking distance to the waterfront, shopping, dining, and the beloved Carpenter Street Saloon. The property is an active short term rental (airbnb). New owners will need to renew the rental license should they wish to continue to operate the

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    107 Carpenter St, Saint Michaels, MD 21663
  • 1110 Jefferson Ave, Saint Michaels, MD 21663
    1110 Jefferson Ave, Saint Michaels, MD 21663
    1110 Jefferson Ave, Saint Michaels, MD 21663
    /64

    $400,000 Sold Dec 30, 2024

    • 1,600 Sq Ft
    • $250/SF
    • 175 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1984

    1110 Jefferson Ave, Saint Michaels, MD 21663

    Welcome to this updated ranch-style home in the water-privileged community of Rio Vista. Nestled near downtown St. Michaels, this charming residence offers access to a community marina and boat ramp on Spencer Creek and park with picnic area on the scenic Miles River. Enjoy the convenience of local shops and waterfront dining just moments away. The home’s exterior boasts a covered front porch and

    Christie Bishop Northrop Realty

    1110 Jefferson Ave, Saint Michaels, MD 21663
  • 8288 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8288 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8288 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /64

    $1,550,000 Sold Dec 20, 2024

    • 3,282 Sq Ft
    • $472/SF
    • 189 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1998

    8288 Bozman Neavitt Rd, Saint Michaels, MD 21663

    This substantial brick home with gorgeous sunset views across Harris Creek is a private retreat just five miles from St. Michaels' shops and restaurants. Sited on 4.7 mostly-wooded acres, the home features a first floor primary suite with waterside sitting area, a family room with woodburning fireplace and a striking stone accent wall, dining room, spacious eat-in kitchen, den and screened porch.

    Debra Crouch Benson & Mangold, LLC

    8288 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 409 Seymour Ave, Saint Michaels, MD 21663
    409 Seymour Ave, Saint Michaels, MD 21663
    409 Seymour Ave, Saint Michaels, MD 21663
    /36

    $485,000 Sold Dec 18, 2024

    • 2,016 Sq Ft
    • $241/SF
    • 7 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    409 Seymour Ave, Saint Michaels, MD 21663

    We are in receipt of multiple offers on 409 Seymour Avenue, St Michaels. An offer deadline of Monday, December 2 at 4p.m has been set. Great St Michaels location just a short stroll to Sam Shore Park on the Miles River and downtown St. Michaels. Perfectly charming, impeccably maintained 3 Bedroom, 2/1 Bath Cape Cod home. Main level Primary Suite. Formal Living Room with French doors to formal

    Karen Hubble Bisbee Hubble Bisbee Christie's International Real Estate

    409 Seymour Ave, Saint Michaels, MD 21663
  • 803 New Ln, Saint Michaels, MD 21663
    803 New Ln, Saint Michaels, MD 21663
    803 New Ln, Saint Michaels, MD 21663
    /15

    $277,500 Sold Dec 18, 2024

    • 1,288 Sq Ft
    • $215/SF
    • 3 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1952

    803 New Ln, Saint Michaels, MD 21663

    Cute Bungalow in the town of Saint Michaels and just a few blocks to the town center and waterfront. House needs some work and is offered for sale " as is ". Great opportunity for a fun remodel and refresh. SELLER WILL BE REVIEWING OFFERS MONDAY, PLEASE SUBMIT BY NOVEMBER 11 , 12 NOON. THANK YOU

    Kelly Showell Benson & Mangold, LLC

    803 New Ln, Saint Michaels, MD 21663
  • 9794 Martingham Cir, Saint Michaels, MD 21663
    9794 Martingham Cir, Saint Michaels, MD 21663
    9794 Martingham Cir, Saint Michaels, MD 21663
    /34

    $935,000 Sold Nov 19, 2024

    • 2,135 Sq Ft
    • $438/SF
    • 10 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1990

    9794 Martingham Cir, Saint Michaels, MD 21663

    Waterfront Townhouse in St Michaels. Highly sought-after community of Martingham, minutes to historic downtown St. Michaels. Home features an entry level Bedroom with en-Suite bathroom, open floorplan featuring living and dining room, a wood burning fireplace (can be converted to gas), open kitchen with breakfast bar and table space. The second floor Guest Bedroom with private bath and an Large

    Brian Gearhart Benson & Mangold, LLC

    9794 Martingham Cir, Saint Michaels, MD 21663

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