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Waterfront Homes for Sale in Saint Michaels, MD

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  • 602 Landing Rd, Saint Michaels, MD 21663
    602 Landing Rd, Saint Michaels, MD 21663
    602 Landing Rd, Saint Michaels, MD 21663
    /57

    $1,725,000

    • 3 Beds
    • 2.5 Baths
    • 3,078 Sq Ft

    602 Landing Rd, Saint Michaels, MD 21663

    Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (866) 970-6336

    602 Landing Rd, Saint Michaels, MD 21663
  • 314 Cove View Dr, Saint Michaels, MD 21663
    314 Cove View Dr, Saint Michaels, MD 21663
    314 Cove View Dr, Saint Michaels, MD 21663
    /8

    $498,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    314 Cove View Dr, Saint Michaels, MD 21663

    Cozy Waterview Townhome Discover serene living in this charming townhome located in the peaceful Cove View Condominium Community. Enjoy breathtaking waterfront views and exclusive access to the community pier, ideal for boating enthusiasts. Situated on a tranquil street, this residence offers the perfect blend of quiet privacy and convenient proximity to local attractions.Inside, you’ll find

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    (877) 708-6124

    314 Cove View Dr, 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
    /72

    $599,000

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

    204 E Marengo St, Saint Michaels, MD 21663

    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 life on Maryland’s Eastern Shore -

    Agent Photo

    Gretchen Wichlinski

    Compass

    (844) 461-3815

    204 E Marengo St, 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
    /108

    $2,249,000

    • 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
  • 7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    /73

    $2,249,000

    • 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
    /68

    $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

    $1,679,000

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

    24390 Oakwood Park Rd, Saint Michaels, MD 21663

    Significant 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

    Janet Larson Benson & Mangold, LLC

    24390 Oakwood Park Rd, 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

    $2,550,000

    • 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
  • 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
  • 204 Lincoln Ave, Saint Michaels, MD 21663
    204 Lincoln Ave, Saint Michaels, MD 21663
    204 Lincoln Ave, Saint Michaels, MD 21663
    /27

    $598,000

    • 3 Beds
    • 2 Baths
    • 2,348 Sq Ft

    204 Lincoln Ave, Saint Michaels, MD 21663

    RIO VISTA COMMUNITY - NO TOWN TAX - WATER FRONT PARK AT THE MILES RIVER FOR RESIDENTS ONLY.GREAT NEIGHBORHOOD RIGHT OUTSIDE OF THE BUZZING HISTORIC ST MICHAELS , GROCERY STORE , HARDWARE STORE, RESTAURANTS, BEAUTY SALON, PILATES ,YMCA , GARDEN CENTER - ALL IS JUST AROUND THE CORNER PRACTICALLY.THE HOME IS CURRENTLY RENTED, 24 HOURS SHOWING APPOINTMENT IS NEEDED.HARDWOOD FLOORS, WOOD

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    204 Lincoln Ave, 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 Open Sat 11AM - 1PM

    • 4 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
  • 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

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    24700 Deepwater Point Dr Unit 1, 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
  • 10554 Miracle House Cir, Claiborne, MD 21624
    10554 Miracle House Cir, Claiborne, MD 21624
    10554 Miracle House Cir, Claiborne, MD 21624
    /25

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 2,170 Sq Ft

    10554 Miracle House Cir, Claiborne, MD 21624

    Quality construction throughout. This Custom Coastal Home has all the bells and whistles ..... hardwood cherry floors, masonry fireplace, 1st floor primary suite, double porches to enjoy the sunsets over Eastern Bay. Gourmet kitchen with stainless steel appliances. Two screened in porches for dining or sleeping. Very private with professional landscaping. Easy walk to Claiborne boat ramp, beach

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    10554 Miracle House Cir, Claiborne, MD 21624
  • 100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    /40

    $470,000

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

    100 Bush Terrace, Saint Michaels, MD 21663

    This home allows for a 3.12% FHA Assumable Loan! 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.

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    100 Bush Terrace, Saint Michaels, MD 21663
  • 8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    /33

    $993,000

    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    8090 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled behind spectacular Japanese Red Maples is a cozy 3 bedroom, 2 bath cottage overlooking Harris Creek with panoramic sunsets! Along with a large family room, dining room enjoy spectacular water views from the screened porch. Property is in excellent condition with a new roof, heat pump and well pump. Offered as a “turn key” investment with all furniture and fixtures. Located in historic St.

    Bill Wieland Benson & Mangold, LLC

    8090 Bozman Neavitt Rd, Bozman, MD 21612
  • 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

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    228 Perry Cabin Dr Unit 228 / 226, 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
  • 962 San Domingo Ct, Saint Michaels, MD 21663
    962 San Domingo Ct, Saint Michaels, MD 21663
    962 San Domingo Ct, Saint Michaels, MD 21663
    /103

    $2,449,000 Open Sat 11AM - 1PM

    • 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
  • 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, 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
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 81 days on the market compared to the national average of 57 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $770,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$770,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$470,000
Median 2 Bedroom Sale Price
$349,500
Average Price Per Sq Ft
$414
Number of Homes for Sale
45
Last 12 months Home Sales
72
Months of Supply
7.50
Median List Price
$795,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
How to Buy a Home How to Finance a Home How to Sell a Home

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