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Waterfront Homes for Sale in Saint Michaels, MD

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  • 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

    $525,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Priced to Sell - Huge Price Improvement! Your St. Michaels weekend escape may be more attainable than you think.Trade the traffic and weekly routine for weekends in one of the Eastern Shore’s most beloved waterfront towns. 204 E Marengo Street offers the perfect combination of location, low-maintenance living, and your own private backyard oasis—ideal as a weekend retreat or primary

    Agent Photo

    Gretchen Wichlinski

    Compass

    204 E Marengo St, 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

    $499,000

    $26K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1211 Washington Dr, Saint Michaels, MD 21663

    Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application

    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

    $499,000

    $26K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1215 Washington Dr, Saint Michaels, MD 21663

    RDesirable Rio Vista Duplex – Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with

    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 Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    204 Lincoln Ave, Saint Michaels, MD 21663
  • 23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    /64

    $3,000,000

    • 4 Beds
    • 3 Baths
    • 2,815 Sq Ft

    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    FALL IN LOVE WITH LIFE IN ST. MICHAELS!As summer fades, the Eastern Shore becomes even more captivating. Just one mile from vibrant downtown St. Michaels, this meticulously renovated waterfront residence offers easy access to seasonal festivals, exceptional dining, charming boutiques and year-round waterfront activities.Designed for effortless one-level living, the home combines

    Carrie Mock Engel & Völkers Annapolis

    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
  • 214 Madison Ave, Saint Michaels, MD 21663
    214 Madison Ave, Saint Michaels, MD 21663
    214 Madison Ave, Saint Michaels, MD 21663
    /23

    $375,000

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,743 Sq Ft

    214 Madison Ave, Saint Michaels, MD 21663

    Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout and plenty of potential for its next owner. The main level features beautiful hardwood floors, a galley kitchen, a separate dining room, and comfortable living spaces. Outside, you'll find a spacious yard with a storage shed, providing plenty of room for outdoor activities, gardening, or future

    Shelley Baden Berkshire Hathaway HomeServices PenFed Realty

    214 Madison Ave, Saint Michaels, MD 21663
  • 806 Calvert Ave, Saint Michaels, MD 21663
    806 Calvert Ave, Saint Michaels, MD 21663
    806 Calvert Ave, Saint Michaels, MD 21663
    /27

    $525,000

    • 2 Beds
    • 2 Baths
    • 851 Sq Ft

    806 Calvert Ave, Saint Michaels, MD 21663

    Located in Bentley Hay and within walking distance of Historic St. Michaels, this charming cottage would make an exceptional pied-à-terre. Enjoy two bedrooms and two bathrooms on separate levels, with tremendous privacy and rear alley access. Easy access to nearby parks is perfect for leisurely strolls. Convenient public services and amenities are just a stone's throw away, making daily errands a

    Schuyler Benson Benson & Mangold, LLC

    806 Calvert Ave, Saint Michaels, MD 21663
  • 1002 Wades Farm Ln, McDaniel, MD 21647
    1002 Wades Farm Ln, McDaniel, MD 21647
    1002 Wades Farm Ln, McDaniel, MD 21647
    /90

    $2,995,000

    • 6 Beds
    • 6.5 Baths
    • 4,656 Sq Ft

    1002 Wades Farm Ln, McDaniel, MD 21647

    With huge sunset views across Eastern Bay, this stylishly-updated property is the perfect retreat! The main house with three en-suite bedrooms overlooks a large waterside deck, saltwater pool and screened pool house. A wisteria-covered pergola leads the the 1920's two-bedroom guest house with wrap-around porch at the water's edge. The one-bedroom carriage house completes the compound. Great

    Debra Crouch Benson & Mangold, LLC

    1002 Wades Farm Ln, McDaniel, MD 21647
  • 9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /32

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 3,028 Sq Ft

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663

    Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long,

    Tom Crouch Benson & Mangold, LLC

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 104 Mulberry St, Saint Michaels, MD 21663
    104 Mulberry St, Saint Michaels, MD 21663
    104 Mulberry St, Saint Michaels, MD 21663
    /74

    $1,399,000

    $71K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,938 Sq Ft

    104 Mulberry St, Saint Michaels, MD 21663

    This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while

    Barbara Best RE/MAX One

    104 Mulberry 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
    /53

    $2,149,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,017 Sq Ft

    7149 Drum Point Rd, Saint Michaels, MD 21663

    BACK ON THE MARKET WITH A NEW PRICE — DON’T MISS THIS EXCEPTIONAL WATERFRONT OPPORTUNITY!Tucked away in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront retreat offers a rare combination of privacy, comfort, and quintessential Eastern Shore charm—all just minutes from the heart of town.Formerly a successful vacation rental, this beautifully

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7149 Drum Point Rd, Saint Michaels, MD 21663
  • 9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    /3

    $435,000

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

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663

    Enjoy the charm of St. Michaels from this end-unit townhome in Martingham. Offering three bedrooms and two full baths, the home features a flexible layout with a first-floor bedroom and full bath—well suited for guests, a home office, or convenient main-level living. The renovated kitchen has white cabinetry and stone countertops, with a glass door opening to a bright, tile-floored sunroom. A

    Kaitlyn Collins Benson & Mangold, LLC

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
  • 202 E Chestnut St, Saint Michaels, MD 21663
    202 E Chestnut St, Saint Michaels, MD 21663
    202 E Chestnut St, Saint Michaels, MD 21663
    /50

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 2,052 Sq Ft

    202 E Chestnut St, Saint Michaels, MD 21663

    Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated

    Wink Cowee Benson & Mangold, LLC

    202 E Chestnut St, Saint Michaels, MD 21663
  • 104 Madison Ave, Saint Michaels, MD 21663
    104 Madison Ave, Saint Michaels, MD 21663
    /2

    $459,900

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

    104 Madison Ave, Saint Michaels, MD 21663

    This well-maintained duplex with new roof in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units

    Chuck Mangold Benson & Mangold, LLC

    104 Madison Ave, 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
    /54

    $725,000

    $100K PRICE DROP
    • 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
  • 8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    /73

    $939,000

    $54K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    8090 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled in the serene enclave of Bozman, on Harris Creek this exquisite 1940s style bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers along with fantastic sunset views and a sheltered cove. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed

    Bill Wieland Benson & Mangold, LLC

    8090 Bozman Neavitt Rd, Bozman, MD 21612
  • 24580 Deepwater Point Dr Unit 3, Saint Michaels, MD 21663
    24580 Deepwater Point Dr Unit 3, Saint Michaels, MD 21663
    24580 Deepwater Point Dr Unit 3, Saint Michaels, MD 21663
    /43

    $398,000

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

    24580 Deepwater Point Dr Unit 3, Saint Michaels, MD 21663

    Nestled in the serene enclave of Gull Wing Villas, this exquisite bungalow-style townhouse offers a harmonious blend of comfort and relaxation. Step inside to discover an inviting open floor plan that seamlessly combines the dining and living areas, perfect for both relaxation and entertaining. The warmth of wood floors and the charm of a brick gas fireplace create an ambiance that feels like

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24580 Deepwater Point Dr Unit 3, Saint Michaels, MD 21663
  • 301 Lincoln Ave, Saint Michaels, MD 21663
    301 Lincoln Ave, Saint Michaels, MD 21663
    301 Lincoln Ave, Saint Michaels, MD 21663
    /16

    $474,900

    Open House 10/10 Coming Soon Oct 9
    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft

    301 Lincoln Ave, Saint Michaels, MD 21663

    Coming soon in St. Michaels! **OPEN HOUSE Saturday October 3rd 11AM-1PM** This charming cottage-styled home is beautifully maintained and truly pristine inside and out. Hardwood floors, a cozy wood-burning fireplace, spacious bedrooms, updated bathrooms and a bright and airy sunroom create a home that feels warm and inviting from the moment you step inside. Outside, enjoy a large private backyard

    Crystal Smith RE/MAX Executive

    301 Lincoln Ave, Saint Michaels, MD 21663
  • 24575 Deepwater Point Dr, Saint Michaels, MD 21663
    24575 Deepwater Point Dr, Saint Michaels, MD 21663
    24575 Deepwater Point Dr, Saint Michaels, MD 21663
    /30

    $660,000

    • 3 Beds
    • 2.5 Baths
    • 2,796 Sq Ft

    24575 Deepwater Point Dr, Saint Michaels, MD 21663

    Sprawling, 3 bedroom, 2 full bath, 1 half bath contemporary ranch home with an oversized 2-car attached garage, rear sunroom overlooking a rear patio, fish pond and gazebo. All of this on a 1.28 +/- acre parcel that backs to a pond/green of the Links at Perry Cabin Golf Course. This home has access to said golf club (membership required), scenic walking and biking trails, a nearby waterfront

    John Fifer Brokers Realty Group, LLC

    24575 Deepwater Point Dr, 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
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    /119

    $1,945,000

    $50K PRICE DROP
    • 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
  • 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
    /30

    $455,000

    $25K PRICE DROP
    • 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

Real Estate & Homes for Sale in Saint Michaels, MD

Home Prices in Saint Michaels, MD

The median home sale price in Saint Michaels, MD is $786,250, down 1% year-over-year. Homes in Saint Michaels sell in 76 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$786,250
Median Single Family Sale Price
$937,500
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$399,000
Average Price Per Sq Ft
$420
Number of Homes for Sale
22
Last 12 months Home Sales
86
Months of Supply
5.40
Median List Price
$799,475
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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