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Waterfront Homes for Sale in Saint Michaels, MD

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  • 228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    /119

    $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

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (877) 709-5322

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
  • 204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    /65

    $599,000 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Coming Soon to Saint Michael's - the perfect weekend getaway does exist — and it’s affordable. Escape the city / suburbs and spend your weekends in the quintessential Eastern Shore town of St. Michaels, known for its picturesque streets, quaint shops, vibrant dining scene, wineries, and distilleries. This charming waterfront community has everything you need to relax, recharge, and truly enjoy

    Agent Photo

    Gretchen Wichlinski

    Compass

    (844) 461-3815

    204 E Marengo St, Saint Michaels, MD 21663
  • 24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    /47

    $369,000

    • 2 Beds
    • 2.5 Baths
    • 1,486 Sq Ft

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663

    Price improvement! Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the home’s warm, inviting feel. The upper-level living area features shining hardwood floors, and the home

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (888) 352-1904

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
  • 1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    /14

    $525,000

    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1211 Washington Dr, Saint Michaels, MD 21663

    DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HELP PAYING FOR YOUR MORTGAGE. THESE DUPLEXES RARELY BECOME AVAILABLE.The duplex is located in a water access community with dock access through the owner's approved application and payment.The building consists of two units with mirrored floor plans. They offer a kitchen with small eating area, an open

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1211 Washington Dr, Saint Michaels, MD 21663
  • 1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    /30

    $525,000

    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1215 Washington Dr, Saint Michaels, MD 21663

    DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HELP PAYING FOR YOUR MORTGAGE. THESE DUPLEXES RARELY BECOME AVAILABLE. The duplex is located in a water access community with dock access through the owner's approved application and payment. The building consists of two units with mirrored floor plans. They offer a kitchen with small eating area, an open

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1215 Washington Dr, Saint Michaels, MD 21663
  • 24965 Back Creek Dr, Saint Michaels, MD 21663
    24965 Back Creek Dr, Saint Michaels, MD 21663
    24965 Back Creek Dr, Saint Michaels, MD 21663
    /64

    $739,000

    • 3 Beds
    • 2.5 Baths
    • 2,798 Sq Ft

    24965 Back Creek Dr, Saint Michaels, MD 21663

    Tucked into the heart of Back Creek Landing, this home offers the kind of layout and setting that just works—comfortable, well thought out, and connected to both nature and town. The main living space is designed around how people actually live. The kitchen is open and inviting, with a bright eat-in area and an elevated counter with seating—perfect for morning coffee, casual meals, or simply

    Kathleen Coale Benson & Mangold, LLC

    24965 Back Creek Dr, Saint Michaels, MD 21663
  • 938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    /60

    $2,390,000 Open House 4/04

    • 4 Beds
    • 5.5 Baths
    • 3,000 Sq Ft

    938 Marea Terrace, Saint Michaels, MD 21663

    Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and

    Carolina Barksdale Benson & Mangold, LLC

    938 Marea Terrace, Saint Michaels, MD 21663
  • 222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    /59

    $1,885,000

    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    222 E Chestnut St, Saint Michaels, MD 21663

    Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    222 E Chestnut St, Saint Michaels, MD 21663
  • 24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    /66

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    24912 Back Creek Dr, Saint Michaels, MD 21663

    Back Creek Landing home for sale in St. Michaels, MD — located in one of the town’s most desirable neighborhoods, known for its peaceful setting, friendly community, and proximity to downtown St. Michaels. This home is just minutes away by bike or golf cart, offering easy access to shops, restaurants, the harbor, and waterfront activities while still feeling private and serene. This beautifully

    Kathleen Coale Benson & Mangold, LLC

    24912 Back Creek Dr, Saint Michaels, MD 21663
  • 7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    /72

    $2,249,000 Open House 4/04

    • 3 Beds
    • 3 Baths
    • 3,017 Sq Ft

    7149 Drum Point Rd, Saint Michaels, MD 21663

    ST MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE BUZZLING TOWN OF ST MICHAELS AND ITS MANY RESTAURANTS, SHOPS , CAFES, THE MOTOR MUSEUM AND THE CHESAPEAKE BAY MARITIME MUSEUM. WHERE EVER YOU TURN YOU SEE WATER. FEEL THE BREEZES , LOUNGE BY THE POOL OR NAP IN YOUR HAMMOCK UNDER THE SHADY TREES BY THE SHORELINE. THIS THREE BEDROOM SOLID BRICK HOME WITH OPEN FLOORPLAN ,

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7149 Drum Point Rd, Saint Michaels, MD 21663
  • 23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    /70

    $3,100,000

    • 4 Beds
    • 3.5 Baths
    • 4,035 Sq Ft

    23961 Lynnewood Dr, Saint Michaels, MD 21663

    Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining

    Barbara Watkins Benson & Mangold, LLC

    23961 Lynnewood Dr, Saint Michaels, MD 21663
  • 24390 Oakwood Park Rd, Saint Michaels, MD 21663
    24390 Oakwood Park Rd, Saint Michaels, MD 21663
    24390 Oakwood Park Rd, Saint Michaels, MD 21663
    /68

    $1,825,000

    • 4 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    24390 Oakwood Park Rd, Saint Michaels, MD 21663

    Price Improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all

    Janet Larson Benson & Mangold, LLC

    24390 Oakwood Park Rd, Saint Michaels, MD 21663
  • 9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    /32

    $385,000

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

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663

    Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled within the famous "links at Perry Cabin " , one of the few units with a screened porch . Enjoy the beautiful golf course views from the second floor, the first floor is private with its landscaping. Bathroom and kitchen countertops are granite, the kitchen has a space for a breakfast table, Living and dining

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
  • 100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    /40

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    100 Bush Terrace, Saint Michaels, MD 21663

    Welcome to easy Eastern Shore living in the charming waterfront town of St. Michaels! This 3-bedroom, 2 bath, 1,232 sq. ft. home is located in the desirable community of Rio Vista offering direct access to the Miles River, complete with a community dock, boat slips, and boat ramp — perfect for boating, crabbing, paddleboarding, or sunset cruises. Enjoy the relaxed coastal lifestyle just minutes

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    100 Bush Terrace, Saint Michaels, MD 21663
  • 24645 Long Haul Rd, Saint Michaels, MD 21663
    24645 Long Haul Rd, Saint Michaels, MD 21663
    24645 Long Haul Rd, Saint Michaels, MD 21663
    /112

    $2,900,000 Open Sat 12PM - 3PM

    • 4 Beds
    • 4.5 Baths
    • 3,677 Sq Ft

    24645 Long Haul Rd, Saint Michaels, MD 21663

    Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for

    Donna Dickinson Coldwell Banker Realty

    24645 Long Haul Rd, Saint Michaels, MD 21663
  • 8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /60

    $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
  • 24977 Back Creek Dr, Saint Michaels, MD 21663
    24977 Back Creek Dr, Saint Michaels, MD 21663
    24977 Back Creek Dr, Saint Michaels, MD 21663
    /70

    $749,999

    • 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
  • 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
    /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, 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 bright and open living area with gas fireplace, custom built-ins,

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • 205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    /62

    $2,575,000

    • 5 Beds
    • 8.5 Baths
    • 4,394 Sq Ft

    205 Cherry St, St. Michaels, MD 21663

    205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are

    Robert Lacaze TTR Sotheby's International Realty

    205 Cherry St, St. Michaels, MD 21663
Maryland Talbot County Saint Michaels

Real Estate & Homes for Sale in Saint Michaels, MD

Home Trends in Saint Michaels, MD

On average, homes in Saint Michaels, MD sell after 72 days on the market compared to the national average of 55 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $795,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$795,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$470,000
Median 2 Bedroom Sale Price
$339,000
Average Price Per Sq Ft
$421
Number of Homes for Sale
38
Last 12 months Home Sales
71
Months of Supply
6.40
Median List Price
$799,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
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