Saint Michaels, MD Homes for Sale

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  $1,995,000

  • 6 Beds
  • 6 Baths
  • 4,089 Sq Ft

  228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663

  Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a

  Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

  228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
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  $1,379,800

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,332 Sq Ft

  7865 Pea Neck Rd, Saint Michaels, MD 21663

  Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan

  Jana Meredith Meredith Fine Properties

  7865 Pea Neck Rd, Saint Michaels, MD 21663
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  $649,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,144 Sq Ft

  24561 Deepwater Point Dr, Saint Michaels, MD 21663

  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,

  Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

  24561 Deepwater Point Dr, Saint Michaels, MD 21663
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  $8,495,000

  • 6 Beds
  • 11 Baths
  • 17,402 Sq Ft

  8620 Bozman Neavitt Rd, Saint Michaels, MD 21663

  NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green,

  Doc Keane Washington Fine Properties, LLC

  8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
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  $474,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  105 Seymour Ave, Saint Michaels, MD 21663

  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 an

  Pamela Ackermann-Doll RE/MAX Executive

  105 Seymour Ave, Saint Michaels, MD 21663
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  $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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  $2,449,000

  Open Thu 10AM - 12PM

  • 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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  $699,999

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,010 Sq Ft

  24977 Back Creek Dr, Saint Michaels, MD 21663

  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

  Eddie Mangold Benson & Mangold, LLC

  24977 Back Creek Dr, Saint Michaels, MD 21663
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  $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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  $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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  $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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  $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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