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Saint Michaels, MD Homes for Sale

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  • 24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
    /36

    $368,000

    $7K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft

    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663

    All resonable offers considered! Move in ready! Meticulously maintained 2 bedroom, 2.5 bath townhome offers comfort, privacy, and inviting living spaces throughout. The galley kitchen features a charming breakfast nook and flows into the dining and living area, highlighted by a wood-burning fireplace. Just beyond, a cozy sitting area opens to a brick patio overlooking a lovely backyard bordered

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    24362 Widgeon Place Unit 5, 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

    $539,900

    $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Just reduced - Priced to sell! The perfect weekend getaway does exist—and it's more attainable than you might think.Escape the city and discover the charm of St. Michaels, one of the Eastern Shore's most beloved waterfront towns. Known for its picturesque streets, waterfront dining, boutique shopping, wineries, marinas, and laid-back coastal lifestyle, St. Michaels offers the perfect

    Agent Photo

    Gretchen Wichlinski

    Compass

    204 E Marengo St, Saint Michaels, MD 21663
  • 109 W Marengo St, Saint Michaels, MD 21663
    109 W Marengo St, Saint Michaels, MD 21663
    109 W Marengo St, Saint Michaels, MD 21663
    /32

    $995,000

    $54K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,250 Sq Ft

    109 W Marengo St, Saint Michaels, MD 21663

    This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area

    Chuck Mangold Benson & Mangold, LLC

    109 W Marengo St, Saint Michaels, MD 21663
  • 9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    /20

    $339,900

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663

    Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached

    Chuck Mangold Benson & Mangold, LLC

    9531 Quail Hollow Dr Unit 402, 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

    Extraordinary waterfront living on 3+ acres with more than 500 feet of stunning water views—offering the privacy of being miles from civilization, yet just 1 mile from famed, historic downtown St. Michaels. Extensively renovated and meticulously cared for, this exceptional one-level living residence provides relaxed comfort, thoughtful design and effortless living in a a resort-like setting. Its

    Carrie Mock Engel & Völkers Annapolis

    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
  • 9521 Quail Hollow Dr Unit 605, Saint Michaels, MD 21663
    9521 Quail Hollow Dr Unit 605, Saint Michaels, MD 21663
    9521 Quail Hollow Dr Unit 605, Saint Michaels, MD 21663
    /34

    $490,000

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

    9521 Quail Hollow Dr Unit 605, Saint Michaels, MD 21663

    With extensive updating done less than three years ago, this home in the popular Martingham community shows beautifully! The spacious, open living room with hardwood floors and fireplace overlooks a pavered patio and lots of greenspace beyond. The kitchen is up to date and well designed, and a pocket door separates it from the first floor bedroom suite, which could also be a den or office.

    Debra Crouch Benson & Mangold, LLC

    9521 Quail Hollow Dr Unit 605, 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
  • 9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    /66

    $1,685,000

    • 5 Beds
    • 5 Baths
    • 4,728 Sq Ft

    9180 Saint Michaels Rd, Saint Michaels, MD 21663

    UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL .ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9180 Saint Michaels Rd, Saint Michaels, MD 21663
  • 111 Chesapeake Ave, Saint Michaels, MD 21663
    111 Chesapeake Ave, Saint Michaels, MD 21663
    111 Chesapeake Ave, Saint Michaels, MD 21663
    /40

    $949,000

    Open Sat 12PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft

    111 Chesapeake Ave, Saint Michaels, MD 21663

    Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated

    Jana Meredith Meredith Fine Properties

    111 Chesapeake 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
  • Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    /25

    $799,000

    New Construction
    • 4 Beds
    • 2.5 Baths

    Lot 16A Meadow St, Saint Michaels, MD 21163

    Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe.Time to make your personal selections. Make this home your personal statement.Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more.Make this

    George Bailey Keller Williams Flagship

    Lot 16A Meadow St, Saint Michaels, MD 21163
  • 210 Brooks Ln, Saint Michaels, MD 21663
    210 Brooks Ln, Saint Michaels, MD 21663
    /2

    $279,000

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft

    210 Brooks Ln, Saint Michaels, MD 21663

    Discover a prime investment opportunity in the desirable St. Michaels community. This 3-bedroom, 2-bathroom ranch-style home, built in 1960, boasts a spacious 1,340 sq. ft. of potential. With its classic vinyl siding, this property is ready for some TLA and future enhancements. The roof is less than 10 years old and layout offers flexibility, making it easy to adapt the space. The 0.17-acre lot

    Marla Baines Meredith Fine Properties

    210 Brooks Ln, Saint Michaels, MD 21663
  • 912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    /11

    $199,000

    $30K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $796,000 per Acre

    912 Calvert Ave, Saint Michaels, MD 21663

    One of the few remaining building lots in the St. Michaels area. This is a prime building lot, 75' x 150', ready for someone to design and construct a new home. Public water/sewer and high-speed internet available for hookup. Calvert Avenue is a convenient address, near a public waterfront park on the Miles River, St. Michaels Harbor, boat ramps, schools, banks, grocery stores and St. Michaels'

    Tom Crouch Benson & Mangold, LLC

    912 Calvert Ave, Saint Michaels, MD 21663
  • 105 W Marengo St, Saint Michaels, MD 21663
    105 W Marengo St, Saint Michaels, MD 21663
    105 W Marengo St, Saint Michaels, MD 21663
    /4

    $299,900

    $49K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,656 Sq Ft

    105 W Marengo St, Saint Michaels, MD 21663

    INVESTOR SPECIAL – PRIME IN-TOWN ST. MICHAELS OPPORTUNITY! Bring your contractor, vision, and renovation plans to 105 W Marengo St. This circa-1890 home offers approximately 1,656 square feet and presents an excellent value-add opportunity for an investor, renovator, or buyer looking for a substantial project in highly desirable St. Michaels.The property is ready for renovation, providing

    Arlene Reading Witz Realty, LLC

    105 W Marengo St, Saint Michaels, MD 21663
  • 9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    /38

    $399,900

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    9818 Tilghman Island Rd, McDaniel, MD 21647

    Wonderful price for a wonderful property! Don't miss out ! The Perfect Blend of Space & Proximity. Loved by one family, this 4 bedroom 2 1/2 bath home is ready for the next owner. Situated on a beautiful1-acre parcel, this property is framed by magnificent, beautifully spaced mature trees and a cool gazebo to enjoy the park-like setting. Located in desirable McDaniel, you enjoy the ultimate

    Valerie Brown Coldwell Banker Realty

    9818 Tilghman Island Rd, McDaniel, MD 21647
  • 24700 Deepwater Unit 20, Saint Michaels, MD 21663
    24700 Deepwater Unit 20, Saint Michaels, MD 21663
    24700 Deepwater Unit 20, Saint Michaels, MD 21663
    /55

    $385,000

    $14K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,477 Sq Ft

    24700 Deepwater Unit 20, Saint Michaels, MD 21663

    Whether you are looking for a full-time residence, weekend retreat, or investment property, this unit is truly move-in ready. Situated in Martingham community just minutes from St. Michaels, shops, restaurants and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship,

    Monica Penwell TTR Sotheby's International Realty

    24700 Deepwater Unit 20, 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
  • 807 Radcliff Ave, Saint Michaels, MD 21663
    807 Radcliff Ave, Saint Michaels, MD 21663
    807 Radcliff Ave, Saint Michaels, MD 21663
    /41

    $775,000

    $85K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,027 Sq Ft

    807 Radcliff Ave, Saint Michaels, MD 21663

    ***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze

    Adam Ellison Long & Foster Real Estate, Inc.

    807 Radcliff Ave, Saint Michaels, MD 21663
  • 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
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /27

    $295,000

    • Land
    • 23,958 Sq Ft
    • $536,364 per Acre

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot,

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    /56

    $1,195,000

    • 4 Beds
    • 4 Baths
    • 3,528 Sq Ft

    114 W Chestnut St, St. Michaels, MD 21663

    Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant

    Robert Lacaze TTR Sotheby's International Realty

    114 W Chestnut St, St. 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
  • 7963 Pond Haven Ct, Saint Michaels, MD 21663
    7963 Pond Haven Ct, Saint Michaels, MD 21663
    7963 Pond Haven Ct, Saint Michaels, MD 21663
    /65

    $655,000

    • 3 Beds
    • 2.5 Baths
    • 3,010 Sq Ft

    7963 Pond Haven Ct, Saint Michaels, MD 21663

    Charming Coastal Retreat with Endless Potential in Backcreek LandingWelcome to this beautiful two-story home in the highly sought-after Backcreek Landing neighborhood, just minutes from historic St. Michaels. Blending coastal elegance with incredible value, this property features a brand-new roof with lifetime shingles and is attractively priced, leaving you budget flexibility to update the

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7963 Pond Haven Ct, Saint Michaels, MD 21663
  • 407 Seymour Ave, Saint Michaels, MD 21663
    407 Seymour Ave, Saint Michaels, MD 21663
    407 Seymour Ave, Saint Michaels, MD 21663
    /31

    $799,950

    • 4 Beds
    • 3.5 Baths
    • 2,154 Sq Ft

    407 Seymour Ave, Saint Michaels, MD 21663

    Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light

    Barbara Watkins Benson & Mangold, LLC

    407 Seymour Ave, Saint Michaels, MD 21663
  • 101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    /38

    $1,129,000

    Open Sat 1PM - 3PM $155K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    101 Mulberry St, Saint Michaels, MD 21663

    Dramatic Price Drop!!! Seller ready to sell this beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway

    Jana Meredith Meredith Fine Properties

    101 Mulberry St, 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 10/03 Coming Soon Oct 3
    • 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
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /25

    $779,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, 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
  • 7964 Pond Haven Ct, Saint Michaels, MD 21663
    7964 Pond Haven Ct, Saint Michaels, MD 21663
    7964 Pond Haven Ct, Saint Michaels, MD 21663
    /23

    $795,000

    • 4 Beds
    • 3.5 Baths
    • 2,955 Sq Ft

    7964 Pond Haven Ct, Saint Michaels, MD 21663

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7964 Pond Haven Ct, Saint Michaels, MD 21663
  • 7865 Pea Neck Rd, Saint Michaels, MD 21663
    7865 Pea Neck Rd, Saint Michaels, MD 21663
    7865 Pea Neck Rd, Saint Michaels, MD 21663
    /61

    $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
  • 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
    /36

    $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

    Barbara Watkins Benson & Mangold, LLC

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

Showing Results 1 - 40, Page 1 of 2

Maryland Talbot County

Real Estate & Homes for Sale in Saint Michaels, MD

Why Live in Saint Michaels

Saint Michaels retains much of its historic charm from its origins as a 17th-century Eastern Shore seaport and still draws visitors from around the region to its landmarks and cruises on Miles River. Buyers can search for historic homes that are ...

Learn more about living in Saint Michaels

Saint Michaels, MD Home Prices

Saint Michaels, MD
Median Home Price
$799,999
Median Sale Price
$800,000
+1% YoY
Avg. Price per Square Foot
$425
Median Single Family Price
$901,500
Median Townhouse Price
$457,450
Median Condo Price
$339,000
Total Active Listings
44 listings
Market Conditions
5 Months of Supply
Balanced Market

Frequently Asked Questions

What is the average home price in Saint Michaels, MD?
Homes for sale in Saint Michaels, MD have an average home price of $1,149,536.
Are home prices dropping in Saint Michaels?
Yes, home prices in Saint Michaels are down 5% in the last 12 months.
How many homes have sold over the last 12 months in Saint Michaels, MD?
83 homes have sold in Saint Michaels, MD over the last 12 months.
What is the average household income in Saint Michaels, MD?
The average household income in Saint Michaels, MD is $97K.
What are the most popular zip codes in Saint Michaels, MD?
The most popular zip codes in Saint Michaels, MD include 21663, 21612, 21601, 21662 and 21676.
How much do you need to make to afford a house in Saint Michaels?
The median home price in Saint Michaels is $799,999. If you put a 20% down payment of $160,000 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $4,240 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $182K a year to afford the median home price in Saint Michaels. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Saint Michaels is $97K.
How are the schools in Saint Michaels, MD?
Saint Michaels, MD has highly rated public and private schools. Some of the best schools in Saint Michaels based on Niche Grades are Easton High School, St. Michaels Elementary School and St. Michaels Middle/High School. Browse all the schools in Saint Michaels, MD to learn more.
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