2,706

Saint Michaels, MD Homes

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  • 601 Cove Rd, Saint Michaels, MD 21663
    601 Cove Rd, Saint Michaels, MD 21663
    601 Cove Rd, Saint Michaels, MD 21663
    /39

    $3,250,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 3,289 Sq Ft

    601 Cove Rd, Saint Michaels, MD 21663

    Experience tranquil waterfront living in this stunning 4BR/4.5 BA home sited on .68 acres overlooking the Miles River.This cottage-style home was completely renovated by Focus ConstructionFeaturing exquisite architectural and interior design details throughout and include custom built-ins, and a large dual-sided gas fireplace. The open floor plan offers breathtaking river views from

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    601 Cove Rd, Saint Michaels, MD 21663
  • 217 Dodson Ave, Saint Michaels, MD 21663
    217 Dodson Ave, Saint Michaels, MD 21663
    217 Dodson Ave, Saint Michaels, MD 21663
    /10

    $2,300 Per Month

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • House for Rent

    217 Dodson Ave, Saint Michaels, MD 21663

    Embrace the quintessential Saint Michaels lifestyle in this beautifully renovated Classic Tidewater Cottage, ideally positioned in the heart of one of Maryland’s most beloved waterfront towns. Stroll to local restaurants, boutique shops, galleries, marinas, and the scenic harbor, then return home to relax on the porch or gather in the rear garden for effortless outdoor

    Michael Dillon Benson & Mangold, LLC

    217 Dodson Ave, Saint Michaels, MD 21663
  • 24345 Widgeon Place Unit 25, Saint Michaels, MD 21663
    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663
    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663
    /36

    $418,000

    Sold Apr 07, 2026

    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 1,752 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $239/SF
    • 17 Days On Market

    Current Estimated Value $417,943

    Last Listing Agent Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    24345 Widgeon Place Unit 25, Saint Michaels, MD 21663
    • 110 Lee St, Saint Michaels, MD 21663
      110 Lee St, Saint Michaels, MD 21663
      110 Lee St, Saint Michaels, MD 21663
      /49

      Not Listed For Sale

      110 Lee St, Saint Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 2024
      110 Lee St, Saint Michaels, MD 21663

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Chance Stem LPT Realty, LLC

  • 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
  • 24700 Deepwater Unit 1, Saint Michaels, MD 21663
    24700 Deepwater Unit 1, Saint Michaels, MD 21663
    24700 Deepwater Unit 1, Saint Michaels, MD 21663
    /24

    $2,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • Townhouse for Rent

    24700 Deepwater Unit 1, Saint Michaels, MD 21663

    GREAT RENTAL OPPORTUNITY !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

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24700 Deepwater Unit 1, Saint Michaels, MD 21663
  • 109 Bush Terrace, Saint Michaels, MD 21663
    109 Bush Terrace, Saint Michaels, MD 21663
    109 Bush Terrace, Saint Michaels, MD 21663
    /56

    $525,000

    Sold Sep 26, 2025

    109 Bush Terrace, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • Built 1998

    Last Sold Summary

    • $284/SF
    • 4 Days On Market

    Current Estimated Value $507,527

    Last Listing Agent Cornelia Heckenbach Long & Foster Real Estate, Inc.

    109 Bush Terrace, Saint Michaels, MD 21663
    • 312 N Talbot St, Saint Michaels, MD 21663
      312 N Talbot St, Saint Michaels, MD 21663
      312 N Talbot St, Saint Michaels, MD 21663
      /42

      Est $532,121

      Not Listed For Sale

      312 N Talbot St, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,080 Sq Ft
      • Built 2022
      312 N Talbot St, Saint Michaels, MD 21663

      Last Sold Summary

      • 527 Days On Market

      Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

  • 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
  • 101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    /38

    $3,900 Per Month

    • 0.5 Baths
    • 1,500 Sq Ft
    • House for Rent

    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
  • 204 Mulberry St, Saint Michaels, MD 21663
    204 Mulberry St, Saint Michaels, MD 21663
    204 Mulberry St, Saint Michaels, MD 21663
    /40

    $1,350,000

    Sold Oct 27, 2025

    204 Mulberry St, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,320 Sq Ft
    • Built 1860

    Last Sold Summary

    • $582/SF
    • 2 Days On Market

    Current Estimated Value $1,319,715

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    204 Mulberry St, Saint Michaels, MD 21663
    • 202 Mulberry St, Saint Michaels, MD 21663
      202 Mulberry St, Saint Michaels, MD 21663
      202 Mulberry St, Saint Michaels, MD 21663
      /51

      Est $1,162,303

      Not Listed For Sale

      202 Mulberry St, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 2,703 Sq Ft
      • Built 1890
      202 Mulberry St, Saint Michaels, MD 21663

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Monica Penwell TTR Sotheby's International Realty

  • 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
  • 105 Bush Terrace, Saint Michaels, MD 21663
    105 Bush Terrace, Saint Michaels, MD 21663
    /2

    $1,950 Per Month

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • House for Rent

    105 Bush Terrace, Saint Michaels, MD 21663

    Suzanne Silverstein Benson & Mangold, LLC

    105 Bush Terrace, Saint Michaels, MD 21663
  • 10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    /109

    $6,000,000

    Sold Apr 15, 2026

    10770 Rich Neck Rd, Claiborne, MD 21624

    • 8 Beds
    • 5 Baths
    • 10,240 Sq Ft
    • Built 1824

    Last Sold Summary

    • $586/SF
    • 291 Days On Market

    Current Estimated Value $5,954,392

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
    • 112 Conner St, St. Michaels, MD 21663
      112 Conner St, St. Michaels, MD 21663
      112 Conner St, St. Michaels, MD 21663
      /24

      Est $488,549

      Not Listed For Sale

      112 Conner St, St. Michaels, MD 21663

      • 4 Beds
      • 2 Baths
      • 2,016 Sq Ft
      • Built 1997
      112 Conner St, St. Michaels, MD 21663

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

  • 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
  • 103 Douglas Ln, Saint Michaels, MD 21663
    103 Douglas Ln, Saint Michaels, MD 21663
    103 Douglas Ln, Saint Michaels, MD 21663
    /6

    $2,400 Per Month

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • House for Rent

    103 Douglas Ln, Saint Michaels, MD 21663

    St. Michaels Cape. First floor offers living room with fireplace, dining area/kitchen combo, 2 bedrooms and bath. 2nd floor features 2 bedrooms and bath. Rear deck overlooking private backyard. Storage shed. Walking distance to downtown amenities, shopping and restaurants. Rented unfurnished. No pets. Non-smokers. Credit check and references required. One year + lease. Immediate occupancy.

    Judy Moore Benson & Mangold, LLC

    103 Douglas Ln, 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

    $680,000

    Sold Sep 15, 2026

    24965 Back Creek Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,798 Sq Ft
    • Built 2006

    Last Sold Summary

    • 8% Below List Price
    • $243/SF
    • 129 Days On Market

    Current Estimated Value $727,600

    Last Listing Agent Kathleen Coale Benson & Mangold, LLC

    24965 Back Creek Dr, Saint Michaels, MD 21663
    • 107 Carpenter St, Saint Michaels, MD 21663
      107 Carpenter St, Saint Michaels, MD 21663
      107 Carpenter St, Saint Michaels, MD 21663
      /30

      Est $744,615

      Not Listed For Sale

      107 Carpenter St, Saint Michaels, MD 21663

      • 2 Beds
      • 2 Baths
      • 1,228 Sq Ft
      • Built 1900
      107 Carpenter St, Saint Michaels, MD 21663

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 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
  • 7491 Beach Ave Unit 3, Saint Michaels, MD 21163
    7491 Beach Ave Unit 3, Saint Michaels, MD 21163
    7491 Beach Ave Unit 3, Saint Michaels, MD 21163
    /32

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 1,020 Sq Ft
    • House for Rent

    7491 Beach Ave Unit 3, Saint Michaels, MD 21163

    Charming Second-Floor Two-Bedroom Apartment with Miles River Views Enjoy beautiful views of the Miles River from this charming second-floor two-bedroom apartment, located on a quiet, peaceful street. Set in a well-maintained four-unit building, this home offers a comfortable and welcoming atmosphere with plenty of character. The apartment features lovely wood floors,, and an efficiently equipped

    Mary Lapides Cummings & Co. Realtors

    7491 Beach Ave Unit 3, Saint Michaels, MD 21163
  • 24420 Mallard Place, Saint Michaels, MD 21663
    24420 Mallard Place, Saint Michaels, MD 21663
    24420 Mallard Place, Saint Michaels, MD 21663
    /33

    $787,500

    Sold Jan 15, 2026

    24420 Mallard Place, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,493 Sq Ft
    • Built 1988

    Last Sold Summary

    • $316/SF
    • 97 Days On Market

    Current Estimated Value $787,887

    Last Listing Agent Robert Lacaze TTR Sotheby's International Realty

    24420 Mallard Place, Saint Michaels, MD 21663
    • 107 Chesapeake Ave, Saint Michaels, MD 21663
      107 Chesapeake Ave, Saint Michaels, MD 21663
      107 Chesapeake Ave, Saint Michaels, MD 21663
      /56

      Est $686,136

      Not Listed For Sale

      107 Chesapeake Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,026 Sq Ft
      • Built 2022
      107 Chesapeake Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 103 Days On Market

      Last Listing Agent Jennifer Pogoda Redfin Corp

  • 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
  • 102 Locust St, Saint Michaels, MD 21663
    102 Locust St, Saint Michaels, MD 21663
    102 Locust St, Saint Michaels, MD 21663
    /19

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • 3,166 Sq Ft
    • House for Rent

    102 Locust St, Saint Michaels, MD 21663

    Nestled in the charming Historic St. Michaels, this exquisite 3-bedroom, 2-bathroom colonial home exudes timeless elegance and modern comfort. Step inside to discover a beautifully designed interior featuring rich hardwood floors and a cozy brick fireplace, perfect for intimate gatherings. The heart of the home is the spacious eat-in kitchen, complete with stainless steel appliances, an island,

    Joan Voss JPAR Preferred Properties

    102 Locust St, Saint Michaels, MD 21663
  • 7312 Solitude Rd, Saint Michaels, MD 21663
    7312 Solitude Rd, Saint Michaels, MD 21663
    7312 Solitude Rd, Saint Michaels, MD 21663
    /43

    $1,800,000

    Sold Oct 09, 2025

    7312 Solitude Rd, Saint Michaels, MD 21663

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft
    • Built 1920

    Last Sold Summary

    • $544/SF
    • 1 Day On Market

    Current Estimated Value $1,821,739

    Last Listing Agent Larry Brennan TTR Sotheby's International Realty

    7312 Solitude Rd, Saint Michaels, MD 21663
    • 8941 Bozman Neavitt Rd, Saint Michaels, MD 21663
      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663
      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663
      /71

      Est $4,404,077

      Not Listed For Sale

      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663

      • 4 Beds
      • 4.5 Baths
      • 4,459 Sq Ft
      • Built 2001
      8941 Bozman Neavitt Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

  • 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
  • 205 Railroad Ave Unit A, Saint Michaels, MD 21663
    205 Railroad Ave Unit A, Saint Michaels, MD 21663
    205 Railroad Ave Unit A, Saint Michaels, MD 21663
    /10

    $1,899 Per Month

    • 2 Beds
    • 1 Bath
    • House for Rent

    205 Railroad Ave Unit A, Saint Michaels, MD 21663

    For rent is the upper floor apartment in a 2-apartment building in the Historic District of St. Michaels. Apartment is bright with high ceilings, wood flooring, 2 bedrooms, 1 bath, spacious modern kitchen and an attractive upper deck oriented to the back yard. Off street parking. Pets are strictly case by case. 12 months lease. Good credit and references required.

    Carolina Barksdale Benson & Mangold, LLC

    205 Railroad Ave Unit A, Saint Michaels, MD 21663
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /44

    $1,130,000

    Sold Feb 06, 2026

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,085 Sq Ft
    • Built 1968

    Last Sold Summary

    • $542/SF
    • 73 Days On Market

    Current Estimated Value $1,129,761

    Last Listing Agent Kathleen Eder Compass

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    • 103 Mulberry St, Saint Michaels, MD 21663
      103 Mulberry St, Saint Michaels, MD 21663
      103 Mulberry St, Saint Michaels, MD 21663
      /69

      Est $763,752

      Not Listed For Sale

      103 Mulberry St, Saint Michaels, MD 21663

      • 4 Beds
      • 1.5 Baths
      • 1,596 Sq Ft
      • Built 1860
      103 Mulberry St, Saint Michaels, MD 21663

      Last Sold Summary

      • 149 Days On Market

      Last Listing Agent Tom Crouch Benson & Mangold, LLC

  • 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
  • 215 E Chew Ave, Saint Michaels, MD 21663
    215 E Chew Ave, Saint Michaels, MD 21663
    215 E Chew Ave, Saint Michaels, MD 21663
    /41

    $4,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,304 Sq Ft
    • House for Rent

    215 E Chew Ave, Saint Michaels, MD 21663

    Custom-built in 2019, this home masterfully blends the charm of a historic replica with today’s modern conveniences. Ideally located just a short walk from shops, restaurants, the historic St. Michaels Harbor, and the Chesapeake Bay Maritime Museum, it offers the perfect balance of comfort and lifestyle.Inside, the home features an inviting open-concept living, family, and dining area

    Jana Meredith Meredith Fine Properties

    215 E Chew Ave, Saint Michaels, MD 21663
  • 106 E Chestnut St, Saint Michaels, MD 21663
    106 E Chestnut St, Saint Michaels, MD 21663
    106 E Chestnut St, Saint Michaels, MD 21663
    /39

    $1,225,000

    Sold Jun 05, 2026

    106 E Chestnut St, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 2,282 Sq Ft
    • Built 1830

    Last Sold Summary

    • 8% Below List Price
    • $537/SF
    • 49 Days On Market

    Current Estimated Value $1,234,934

    Last Listing Agent Justin Pokrywka Taylor Properties

    106 E Chestnut St, Saint Michaels, MD 21663
    • 122 W Chestnut St, Saint Michaels, MD 21663
      122 W Chestnut St, Saint Michaels, MD 21663
      122 W Chestnut St, Saint Michaels, MD 21663
      /53

      Est $1,097,777

      Not Listed For Sale

      122 W Chestnut St, Saint Michaels, MD 21663

      • 4 Beds
      • 3.5 Baths
      • 1,890 Sq Ft
      • Built 1975
      122 W Chestnut St, Saint Michaels, MD 21663

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Wink Cowee Benson & Mangold, LLC

  • 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
  • 113 Fremont St, Saint Michaels, MD 21663
    113 Fremont St, Saint Michaels, MD 21663
    /2

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    113 Fremont St, Saint Michaels, MD 21663

    Enjoy the charm of St. Michaels from this inviting 2-bedroom, 1-bath apartment located at 113 Fremont Street. Situated within walking distance of downtown, this convenient location makes it easy to enjoy the restaurants, boutique shops, galleries, waterfront attractions, and historic streets that make St. Michaels one of the Eastern Shore’s most desirable destinations. Stroll into town for

    Jarnell Foster Samson Properties

    113 Fremont St, Saint Michaels, MD 21663
  • 934 Calvert Ave, Saint Michaels, MD 21663
    934 Calvert Ave, Saint Michaels, MD 21663
    /2

    $499,000

    Sold Jul 20, 2026

    934 Calvert Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 2001

    Last Sold Summary

    • $317/SF
    • 14 Days On Market

    Current Estimated Value $496,104

    Last Listing Agent Will Stone Benson & Mangold, LLC

    934 Calvert Ave, Saint Michaels, MD 21663
    • 417 Water St, Saint Michaels, MD 21663
      417 Water St, Saint Michaels, MD 21663
      417 Water St, Saint Michaels, MD 21663
      /65

      Est $1,552,208

      Not Listed For Sale

      417 Water St, Saint Michaels, MD 21663

      • 3 Beds
      • 3.5 Baths
      • 2,579 Sq Ft
      • Built 1880
      417 Water St, Saint Michaels, MD 21663

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Clifford Meredith Meredith Fine Properties

Showing Results 1 - 40, Page 1 of 18

Maryland Talbot County

Real Estate & Homes

Home Prices in Saint Michaels, MD

The median home sale price in Saint Michaels, MD is $787,500, down 1% year-over-year. Homes in Saint Michaels sell in 71 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$787,500
Median Single Family Sale Price
$901,500
Median Townhouse Sale Price
$457,450
Median 2 Bedroom Sale Price
$410,000
Average Price Per Sq Ft
$421
Number of Homes for Sale
2,706
Last 12 months Home Sales
85
Months of Supply
5.20
Median List Price
$799,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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