Homes for Sale in 21663

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  /39

  $459,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  105 Seymour Ave, Saint Michaels, MD 21663

  REDUCED! SAINT MICHAELS CHARMING COTTAGE! Welcome Home to this Adorable Cottage perfectly situated in the desirable and walkable Historic Waterfront Town of Saint Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. A sizable .25 Acre lot with mature trees to include a pecan and walnut tree, mature flower gardens, zoysia grass and

  Pamela Ackermann-Doll RE/MAX Executive

  105 Seymour Ave, Saint Michaels, MD 21663
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  /2

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft

  203 Canton St, Saint Michaels, MD 21663

  Discover this ranch-style home located 1 block to the center of downtown, perfect for those seeking convenience to everything St Michaels has to offer. This 3-bedroom, 2-bathroom residence offers 1,364 sq. ft. of potential, set on a generous 0.17-acre lot. The rails to trails is located right at the end of the street. With a little creativity and vision, this property can be transformed into your

  Melanie Hopkins Coldwell Banker Chesapeake Real Estate Company

  203 Canton St, Saint Michaels, MD 21663
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  /103

  $2,449,000

  • 4 Beds
  • 4.5 Baths
  • 3,300 Sq Ft

  962 San Domingo Ct, Saint Michaels, MD 21663

  This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering

  Eugene Smith TTR Sotheby's International Realty

  962 San Domingo Ct, Saint Michaels, MD 21663
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  /2

  $499,999

  Open Fri 2PM - 4PM Coming Soon

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  24375 Widgeon Place Unit 37, Saint Michaels, MD 21663

  Want to live close to Historic Saint Michaels in a beautiful and low maintenance setting offering ample first floor living? Welcome to 24375 Widgeon Place, Unit 37, nestled in the picturesque Martingham Community just outside Historic St. Michaels . This desirable END UNIT property is the epitome of style and comfort, encapsulating all the charms of eastern shore coastal living. Featuring 3

  Tiffany Cloud Meredith Fine Properties

  24375 Widgeon Place Unit 37, Saint Michaels, MD 21663
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  /36

  $480,000

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

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

  Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a

  Barbara Watkins Benson & Mangold, LLC

  9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
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  /41

  $249,000

  • Land
  • 1.12 Acres
  • $222,321 per Acre

  0 Deepwater Point Dr, Saint Michaels, MD 21663

  ONE OF THE LAST LOTS IN MARTINGHAM ON DEEP WATER POINT DRIVE. LOCATED VERY CLOSE TO THE COMMUNITY WATERFRONT PARK WITH GAZEBO AND CHAIRS FOR PICKNICKS OR JUST RELAXING IN THE BREEZE WATCHING THE BOATS GO BY ; DROP YOUR KAYAK OR ENJOY THE SUNSETS, WALK OR BIKE THERE. THIS LOT IS CLEANED, HAS A BEAUTIFUL ENTRANCE , WATER METER, AND IS READY FOR YOU TO BUILT YOUR MAIN RESIDENCE OR WEEKEND GET AWAY.

  Cornelia Heckenbach Long & Foster Real Estate, Inc.

  0 Deepwater Point Dr, Saint Michaels, MD 21663
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  /91

  $1,985,000

  • 3 Beds
  • 3 Baths
  • 2,622 Sq Ft

  303 Manor St, Saint Michaels, MD 21663

  Welcome to "Mostly Porches" an exceptional coastal retreat with captivating views of the harbor, perfectly situated on a spacious .41 acre corner lot just around the corner from the shops and restaurants of St. Michaels. Built in 2018 with virtually maintenance-free construction, this beautifully designed home offers the ideal blend of comfort, style, and convenience in a rare St. Michaels

  Monica Penwell TTR Sotheby's International Realty

  303 Manor St, Saint Michaels, MD 21663
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  /50

  $2,100,000

  $500K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 4,492 Sq Ft

  7909 Church Neck Rd, Saint Michaels, MD 21663

  Set on 19.5 private acres just minutes from historic waterfront Saint Michaels, this exceptional 4,492 sq ft residence offers the perfect blend of space, privacy, and convenience. The home features four bedrooms and two and a half baths, with expansive living areas ideal for both everyday living and entertaining, including a well-appointed chef's kitchen. The thoughtfully designed layout includes

  Cheri Bruce-Phipps TTR Sotheby's International Realty

  7909 Church Neck Rd, Saint Michaels, MD 21663
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  /25

  $999,000

  New Construction

  • 3 Beds
  • 2.5 Baths

  108 Miles, Saint Michaels, MD 21663

  A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual

  Chuck Mangold Benson & Mangold, LLC

  108 Miles, Saint Michaels, MD 21663

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