2,823

Saint Michaels, MD Homes

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    • /65

      Est $1,541,526 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,579 Sq Ft

      417 Water St, Saint Michaels, MD 21663

      417 Water St, Saint Michaels, MD 21663
  • /44

    $524,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    207 Dodson Ave, Saint Michaels, MD 21663

    Fabulous 1910 Bungalow with welcoming front porch that has been renovated throughout. All main level living with beautiful primary suite offers room for king bed and ample closet space. Primary tiled bath offers luxury walk-in shower with sliding glass doors. Corner guest room with pocket door leading into guest bathroom. Living room has vaulted ceiling with skylight and opens to spacious

    Debra Crouch Benson & Mangold, LLC

    207 Dodson Ave, Saint Michaels, MD 21663
  • /79

    $1,210,000 Sold Sep 12, 2025

    • 2,535 Sq Ft
    • $477/SF
    • 123 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1954

    1026 Riverview Terrace, Saint Michaels, MD 21663

    Experience luxury living in this newly renovated coastal-style home in St. Michaels. Situated on a double lot, this is an exceptional and rare offering, combining water views and water access with a high quality home, redone with incredible attention to detail and livability. The exterior is tastefully appointed with painted brick and shingle-style siding, and an inviting covered front porch

    Carolina Barksdale Benson & Mangold, LLC

    1026 Riverview Terrace, Saint Michaels, MD 21663
    • /34

      Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,652 Sq Ft

      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663

      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663
  • /4

    $895,000

    • Land
    • 2.73 Acres
    • $327,839 per Acre

    0 Bozman Neavitt Rd Unit MDTA2011976, Saint Michaels, MD 21663

    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

    Chuck Mangold Benson & Mangold, LLC

    0 Bozman Neavitt Rd Unit MDTA2011976, Saint Michaels, MD 21663
  • /56

    $220,000 Sold Sep 01, 2025

    • 1,282 Sq Ft
    • $172/SF
    • 358 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1960

    10376 Claiborne Rd, Claiborne, MD 21624

    Looking for a sweet little cottage in a waterfront town minutes from Saint Michaels? The cottage has a brand-new septic system, just installed new toilet, vanity, stove, and refrigerator, hardwood floors, fireplace, large porch off the back, and short walk to Eastern Bay or Tilghman Creek. This home is ready to be loved by its next owner. This property is being sold "as is." Call today for

    Jana Meredith Meredith Fine Properties

    10376 Claiborne Rd, Claiborne, MD 21624
    • /60

      Est $1,789,084 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,644 Sq Ft

      10536 Miracle House Cir, Claiborne, MD 21624

      10536 Miracle House Cir, Claiborne, MD 21624
  • /44

    $585,000

    • 3 Beds
    • 2.5 Baths
    • 1,922 Sq Ft

    228 Tyler Ave, Saint Michaels, MD 21663

    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

    Debra Crouch Benson & Mangold, LLC

    228 Tyler Ave, Saint Michaels, MD 21663
  • /137

    $3,105,000 Sold Aug 28, 2025

    • 2,649 Sq Ft
    • $1,172/SF
    • 5 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1965

    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    Coastal Point Perfection – A re-imagined, fully furnished, and turn-key, short-term rental, second home, or primary residence waterfront retreat opportunity within walking and biking distance of the Town of Saint Michael's. Tucked at the end of a private, tree-lined lane and wrapped in over 700 feet of panoramic waterfront, this exceptional property has been completely transformed from its 1965

    Kimberly Kepnes Monument Sotheby's International Realty

    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    • /27

      Est $944,752 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,213 Sq Ft

      9792 Martingham Cir Unit B1, Saint Michaels, MD 21663

      9792 Martingham Cir Unit B1, Saint Michaels, MD 21663
  • /11

    $229,000

    • Land
    • 0.25 Acre
    • $916,000 per Acre

    912 Calvert Ave, Saint Michaels, MD 21663

    One of the few remaining building lots in the St. Michaels area. This is a prime building lot, 75' x 150', ready for someone to design and construct a new home. Public water/sewer and high-speed internet available for hookup. Calvert Avenue is a convenient address, near schools, banks, grocery stores, boat ramps and St. Michaels' many fine shops, museums and restaurants. A public waterfront park

    Tom Crouch Benson & Mangold, LLC

    912 Calvert Ave, Saint Michaels, MD 21663
  • /93

    $7,000,000 Sold Aug 28, 2025

    • 10,309 Sq Ft
    • $679/SF
    • 472 Days On Market
    • 5 Beds
    • 7 Baths
    • Built 2002

    24629 Beverly Rd, Saint Michaels, MD 21663

    Travel down a mature, holly tree-lined drive and One Beverly reveals itself with understated Eastern Shore elegance. Situated on the 9 acre original farmstead of the 1867 Beverly Manor, this Georgian home provides a southwestern view overlooking San Domingo and Broad Creeks. The 5-bedroom main house, first occupied in 2003, is a traditional Georgian design meticulously built according to

    Clifford Meredith Meredith Fine Properties

    24629 Beverly Rd, Saint Michaels, MD 21663
    • /53

      Est $401,085 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft

      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663

      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663
  • /89

    $3,250,000

    • 4 Beds
    • 6 Baths
    • 5,400 Sq Ft

    9262 Macks Ln, McDaniel, MD 21647

    Just 4.9-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings

    Tom Crouch Benson & Mangold, LLC

    9262 Macks Ln, McDaniel, MD 21647
  • /10

    $182,500 Sold Aug 26, 2025

    • Land
    • 0.13 Acre
    • $1,403,846 per Acre
    • 178 Days On Market

    0 Radcliff Ave Unit MDTA2007626, Saint Michaels, MD 21663

    Build your dream home in Saint Michaels! Only steps away from the YMCA and Saint Michaels school, this lot (approx 75 x 75 ft), situated on the corner of Parsonage and Radcliffe in Bentley Hay, is perfectly located for convenience. Within minutes by foot, you are in the heart of town enjoying the local cuisine and quaint shops. Or take a stroll down the road to enjoy the expansive views of the

    Tiffany Cloud Meredith Fine Properties

    0 Radcliff Ave Unit MDTA2007626, Saint Michaels, MD 21663
    • /18

      Est $384,508 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft

      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663

      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663
  • /44

    $2,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,248 Sq Ft

    25500 Chance Farm Rd, Royal Oak, MD 21662

    Welcome to this exceptional waterfront retreat on 3.5 acres overlooking Solitude Creek in Royal Oak. From the moment you enter, expansive water views set the tone for gracious living. Renovated in 2023 and thoughtfully decorated by Bountiful Home in Easton, this 3,248 sq. ft. residence offers 4 bedrooms and 3.5 baths, including a main-level waterside primary suite with spa-like bath. The gourmet

    Laura Carney TTR Sotheby's International Realty

    25500 Chance Farm Rd, Royal Oak, MD 21662
  • /69

    $800,000 Sold Aug 15, 2025

    • 1,596 Sq Ft
    • $501/SF
    • 149 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1860

    103 Mulberry St, Saint Michaels, MD 21663

    Known as, "The Mary Thomas House," circa 1860, this beautifully maintained and tastefully updated home is absolutely charming, inside and out...A very comfortable home! Centrally located in St. Michaels' Historic District, mid-way between the Harbor, two waterfront parks and Talbot Street (the town's main street), with it's many fine shops and restaurants. All the main attractions, including

    Tom Crouch Benson & Mangold, LLC

    103 Mulberry St, Saint Michaels, MD 21663
    • /57

      Est $854,392 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft

      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663

      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663
  • /41

    $353,900

    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    Welcome to Martingham, a premier golf course and waterfront community located just a mile from historic St. Michaels. This Widgeon Place condo offers two en-suite bedrooms and a half bath, with a thoughtful two-level layout designed for comfort and convenience. The main level features a kitchen with a charming breakfast nook, hardwood floors, a gas fireplace, and an open-concept living area. A

    Amy Berry Meredith Fine Properties

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
  • /41

    $925,000 Sold Aug 11, 2025

    • 3,069 Sq Ft
    • $301/SF
    • 1 Day On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2008

    7841 Pea Neck Rd, Saint Michaels, MD 21663

    Discover refined country living in this impeccably designed modern farmhouse, nestled on 2.34 private acres along prestigious Pea Neck Road in St. Michaels. Offering over 3,000 square feet of thoughtfully curated living space, this property blends high-end finishes with the ease of open-concept living.Step inside to sun-drenched interiors with wide-plank hardwood flooring and soaring

    Dennis Covey Meredith Fine Properties

    7841 Pea Neck Rd, Saint Michaels, MD 21663
    • /48

      Est $850,505 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft

      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663

      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663
  • /89

    $379,000

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663

    Located in the desirable Martingham Quail Hollow Community and nestled alongside the prestigious *Links at Perry Cabin* golf course, this well-maintained 1,800 sq. ft. townhouse has been freshly painted throughout. The home welcomes you with a foyer featuring laminate wood floors that flow into the kitchen and dining area. The spacious living room offers a wood-burning fireplace and room to

    Kim Crouch Ozman Benson & Mangold, LLC

    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663
  • /2

    $600,000 Sold Aug 08, 2025

    • 1,660 Sq Ft
    • $361/SF
    • 82 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    901 S Talbot St, Saint Michaels, MD 21663

    St. Michaels English style Cottage – This Adorable 3-bedroom 2 bath home offers a first-floor primary bedroom, updated kitchen and baths, formal dining room, rear sunroom, and a fenced side and rear patio thoughtfully landscaped. The yard is irrigated. Long sweeping gables and roof peaks, prominent front facing chimney and entrance vestibule standout as architectural features of this 1930’s

    Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, Saint Michaels, MD 21663
    • /56

      Est $476,636 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,752 Sq Ft

      24360 Widgeon Place Unit 7, Saint Michaels, MD 21663

      24360 Widgeon Place Unit 7, Saint Michaels, MD 21663
  • /10

    $149,999

    • Land
    • 0.14 Acre
    • $1,071,421 per Acre

    300 Perry St, Saint Michaels, MD 21663

    New price!...Great opportunity to own a buildable lot in one of Maryland's most charming waterfront towns. This spacious and level parcel offers the perfect canvas for your Eastern shore home. Nestled just blocks from the harbor, shops, restaurants, parks, marinas, and the Chesapeake Bay Maritime Museum. Walk to downtown restaurants and shops! The property combines small-town

    Tammy Durbin Long & Foster Real Estate, Inc.

    300 Perry St, Saint Michaels, MD 21663
  • /63

    $625,000 Sold Aug 07, 2025

    • 1,945 Sq Ft
    • $321/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1988

    9217 Martingham Dr, Saint Michaels, MD 21663

    *NEW AERIAL PHOTOS ADDED* Welcome to 9217 Martingham Drive, St Michaels - A beautifully maintained 3-bedroom, 2.5-bath rancher nestled in the sought-after Martingham community. This inviting home sits on a wooded lot offering privacy and serene natural surroundings, while enjoying a prime location off the 10th fairway of The Links at Perry Cabin golf course. Inside you'll find a thoughtfully

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    9217 Martingham Dr, Saint Michaels, MD 21663
    • /31

      Est $962,124 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,213 Sq Ft

      9792 Martingham Cir, Saint Michaels, MD 21663

      9792 Martingham Cir, Saint Michaels, MD 21663
  • /33

    $825,000

    • 4 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    24420 Mallard Place, Saint Michaels, MD 21663

    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

    Robert Lacaze TTR Sotheby's International Realty

    24420 Mallard Place, Saint Michaels, MD 21663
  • /59

    $830,000 Sold Aug 01, 2025

    • 2,910 Sq Ft
    • $285/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    9240 Martingham Dr, Saint Michaels, MD 21663

    ST MICHAELS LIVING AT ITS BEST! MOVE IN READY STUNNING HOME ON GORGEOUS LANDSCAPED AND IRRIGATED LOT WITH ALL THE NEEDED AMENETIES. HIGH CEILING, THE FIREPLACE IN THE LIVING ROOM FRAMED BY LARGE WINDOWS DISPLAYING THE PARK LIKE YARD. THE GOURMET KITCHEN WITH WINE COOLER, ICE MAKER, SIX BURNER GOURMET STOVE WITH HOOD, SUB ZERO FRIDGE, KITCHEN ISLAND AND A VIEW FROM THE KITCHEN SINK. STEP FROM

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9240 Martingham Dr, Saint Michaels, MD 21663
    • /51

      Est $865,621 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft

      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663

      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
  • /88

    $8,875,000

    • 7 Beds
    • 7.5 Baths
    • 10,240 Sq Ft

    10770 Rich Neck Rd, Claiborne, MD 21624

    Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

    Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
  • /40

    $795,000 Sold Jul 31, 2025

    • 3,098 Sq Ft
    • $257/SF
    • 0 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    24989 Back Creek Dr, Saint Michaels, MD 21663

    Set in the welcoming Back Creek Landing neighborhood, this bright and beautifully updated home offers the best of Eastern Shore living—just moments from the shops, restaurants, and waterfront of downtown St. Michaels.A classic front porch invites you into a thoughtfully designed interior, where natural light and an easy floor plan make everyday living effortless. The open-concept kitchen

    Kathleen Coale Benson & Mangold, LLC

    24989 Back Creek Dr, Saint Michaels, MD 21663
    • /35

      Est $460,530 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,752 Sq Ft

      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663

      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663
  • /53

    $368,500

    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    Martingham, a golf course and waterfront community just a mile outside of Historic St. Michaels with all of its amenities. This Widgeon Place condo is a two-story condo with two en-suite bedrooms and a half bath on the first floor. Living room and dining room are an open floor plan with hardwood floors and fireplace. From the sunroom you can step onto a brick patio which looks out to treed

    Jane Baker Benson & Mangold, LLC

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
  • /52

    $850,000 Sold Jul 31, 2025

    • 2,072 Sq Ft
    • $410/SF
    • 76 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1900

    504 S Talbot St, Saint Michaels, MD 21663

    Nestled in the heart of Historic St. Michaels, this beautifully renovated 1900’s home features, multiple fireplaces, hardwood floors and beams with natural light. This 3-bedroom, 2.5-bathroom residence is a perfect Eastern Shore retreat. A charming covered front porch welcomes you into the cozy living room highlighted by a wood-burning fireplace. The spacious, open-concept kitchen boasts granite

    Kim Crouch Ozman Benson & Mangold, LLC

    504 S Talbot St, Saint Michaels, MD 21663
    • /75

      Est $407,816 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft

      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663

      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663
  • /43

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 2,496 Sq Ft

    24749 Swan Rd, Saint Michaels, MD 21663

    Located in Martingham, home of the newly redesigned Pete Dye golf course, The Links at Perry Cabin. This 3BR/2.5BA Colonial style home is situated on an open 1.13ac lot with a tree lined backyard for privacy. Inside you will enjoy a spacious floor plan, and updated island kitchen, and a large family room highlighted by a wood burning fireplace and a beam ceiling. Upstairs you will find the

    Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, Saint Michaels, MD 21663
  • /19

    $275,000 Sold Jul 31, 2025

    • 1,368 Sq Ft
    • $201/SF
    • 126 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1984

    112 Mitchell St, Saint Michaels, MD 21663

    Located in Saint Michaels Maryland. Within close proximity to everything fun this local town has to offer. Great seafood, boating, at a price that allows you to make it your own. Currently 3 bedrooms and 1 bath. With a very easy remodel, you could make it a 4 bedroom 2 bath. Large rear yard and paved driveway. Full time, weekend home, or rental. OWNER IS READY TO SELL... Let’s see your offer...

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    112 Mitchell St, Saint Michaels, MD 21663
    • /35

      Est $411,440 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft

      24360 Widgeon Place Unit 10, Saint Michaels, MD 21663

      24360 Widgeon Place Unit 10, Saint Michaels, MD 21663

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