2,828

Saint Michaels, MD Homes

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  • /23

    $514,000

    Sold Jun 03, 2026

    23266 Mallard Point Rd, McDaniel, MD 21647

    • 3 Beds
    • 2 Baths
    • 1,744 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Above List Price
    • $295/SF
    • 8 Days On Market

    Current Estimated Value $505,559

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    23266 Mallard Point Rd, McDaniel, MD 21647
    • /50

      Est $694,678

      Not Listed For Sale

      111 Dodson Ave, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 2,015 Sq Ft
      • Built 2021
      111 Dodson Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 106 Days On Market

  • /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
  • /23

    $1,202,000

    Sold Feb 19, 2026

    7361 Solitude Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 2,012 Sq Ft
    • Built 1967

    Last Sold Summary

    • 1% Above List Price
    • $597/SF
    • 4 Days On Market

    Current Estimated Value $1,146,429

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    7361 Solitude Rd, Saint Michaels, MD 21663
    • /56

      Est $775,847

      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

  • /64

    $739,000

    Under Contract
    • 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
  • /61

    $580,000

    Sold Oct 31, 2025

    113 Thompson St, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1900

    Last Sold Summary

    • $370/SF
    • 69 Days On Market

    Current Estimated Value $586,547

    Last Listing Agent Kim Lally EXP Realty, LLC

    113 Thompson St, Saint Michaels, MD 21663
    • /71

      Est $3,663,084

      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

  • /75

    $1,195,000

    $155K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,528 Sq Ft

    114 W Chestnut St, St. Michaels, MD 21663

    Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides

    Wink Cowee Benson & Mangold, LLC

    114 W Chestnut St, St. Michaels, MD 21663
  • /18

    $425,000

    Sold Jun 15, 2026

    1206 Washington Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft
    • Built 1986

    Last Sold Summary

    • 15% Below List Price
    • $176/SF
    • 20 Days On Market

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    1206 Washington Dr, Saint Michaels, MD 21663
    • /72

      Est $1,224,178

      Not Listed For Sale

      104 Mulberry St, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 1,938 Sq Ft
      • Built 1786
      104 Mulberry St, Saint Michaels, MD 21663

      Last Sold Summary

  • /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
  • /2

    $2,100,000

    Sold Jul 27, 2026

    8240 Tricefield Rd, Saint Michaels, MD 21663

    • 5 Beds
    • 6 Baths
    • 5,611 Sq Ft
    • Built 1989

    Last Sold Summary

    • 14% Below List Price
    • $374/SF

    Current Estimated Value $2,433,584

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

    8240 Tricefield Rd, Saint Michaels, MD 21663
    • /30

      Est $873,530

      Not Listed For Sale

      120 W Chestnut St, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,218 Sq Ft
      • Built 1840
      120 W Chestnut St, Saint Michaels, MD 21663

      Last Sold Summary

      • 37 Days On Market

  • /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
  • /2

    $865,000

    Sold Aug 12, 2025

    109 Chesapeake Ave, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Built 2022

    Last Sold Summary

    • $399/SF
    • 2 Days On Market

    Current Estimated Value $823,450

    Last Listing Agent Christopher Coppola Compass

    109 Chesapeake Ave, Saint Michaels, MD 21663
    • /53

      Est $1,133,950

      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

  • /93

    $2,195,000

    $343K PRICE DROP Pending
    • 5 Beds
    • 5.5 Baths
    • 4,673 Sq Ft

    203 E Chew Ave, Saint Michaels, MD 21663

    Significant Price Improvement!!! Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully re-imagined through comprehensive renovations completed in 2023 and 2024. See virtual tours above. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms and 5 and a half baths, this home offers

    Richard Minchik Benson & Mangold, LLC

    203 E Chew Ave, Saint Michaels, MD 21663
  • /80

    $3,200,000

    Sold Jul 15, 2026

    9791 Pintail Place, Saint Michaels, MD 21663

    • 5 Beds
    • 6 Baths
    • 7,300 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Below List Price
    • $438/SF
    • 55 Days On Market

    Current Estimated Value $3,735,696

    Last Listing Agent Kathleen Eder Compass

    9791 Pintail Place, Saint Michaels, MD 21663
    • /65

      Est $1,568,671

      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

  • /11

    $219,000

    $10K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $876,000 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 schools, banks, grocery stores, boat ramps and St. Michaels' many fine shops, museums and restaurants. A public waterfront park

    Tom Crouch Benson & Mangold, LLC

    912 Calvert Ave, Saint Michaels, MD 21663
  • /57

    $1,152,500

    Sold Jun 10, 2026

    114 E Chew Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,336 Sq Ft
    • Built 1890

    Last Sold Summary

    • 16% Below List Price
    • $493/SF
    • 76 Days On Market

    Current Estimated Value $1,227,146

    Last Listing Agent Wink Cowee Benson & Mangold, LLC

    114 E Chew Ave, Saint Michaels, MD 21663
    • /55

      Not Listed For Sale

      24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1978
      24580 Deepwater Point Dr Unit 4, Saint Michaels, MD 21663

      Last Sold Summary

      • 14 Days On Market

  • /59

    $1,885,000

    Pending
    • 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
  • /17

    $465,000

    Sold Jun 12, 2026

    314 Cove View Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • Built 1985

    Last Sold Summary

    • 7% Below List Price
    • $302/SF
    • 3 Days On Market

    Current Estimated Value $501,979

    Last Listing Agent Tracy Higgs-Wagner Meredith Fine Properties

    314 Cove View Dr, Saint Michaels, MD 21663
    • /34

      Not Listed For Sale

      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,652 Sq Ft
      • Built 1979
      24700 Deepwater Point Dr Unit 8, Saint Michaels, MD 21663

      Last Sold Summary

      • 54 Days On Market

  • /63

    $2,250,000

    $250K PRICE DROP Under Contract
    • 5 Beds
    • 2 Baths
    • 4,706 Sq Ft

    8209 Tricefield Rd, Saint Michaels, MD 21663

    Experience the best of Eastern Shore Living at this stunning waterfront retreat. Set on 8+ private acres, this solid brick Dutch Colonial offers timeless architecture, exceptional privacy and spectacular waterfrontage on San Domingo Creek. A long tree lined drive welcomes you to over 4400 square feet of thoughtfully designed living space. Additional highlights include a 2 car garage, paved

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    8209 Tricefield Rd, Saint Michaels, MD 21663
  • /77

    $1,135,000

    Sold Jul 27, 2026

    107 E Chestnut St, Saint Michaels, MD 21663

    • 2 Beds
    • 2 Baths
    • 2,024 Sq Ft
    • Built 1880

    Last Sold Summary

    • 3% Below List Price
    • $561/SF
    • 19 Days On Market

    Current Estimated Value $1,148,306

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    107 E Chestnut St, Saint Michaels, MD 21663
    • /6

      Not Listed For Sale

      0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663

      0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663

      Last Sold Summary

      • 16 Days On Market

  • /38

    $430,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    9818 Tilghman Island Rd, McDaniel, MD 21647

    Improved Price!! 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 Eastern Shore lifestyle:

    Valerie Brown Coldwell Banker Realty

    9818 Tilghman Island Rd, McDaniel, MD 21647
  • /137

    $3,105,000

    Sold Aug 28, 2025

    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    • 4 Beds
    • 4.5 Baths
    • 2,649 Sq Ft
    • Built 1965

    Last Sold Summary

    • $1,172/SF
    • 5 Days On Market

    Current Estimated Value $2,891,007

    Last Listing Agent Kimberly Kepnes Monument Sotheby's International Realty

    23762 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    • /60

      Est $1,470,739

      Not Listed For Sale

      10536 Miracle House Cir, Claiborne, MD 21624

      • 3 Beds
      • 3.5 Baths
      • 3,644 Sq Ft
      • Built 1900
      10536 Miracle House Cir, Claiborne, MD 21624

      Last Sold Summary

      • 31 Days On Market

  • /64

    $1,300,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft

    344 Perry Cabin Dr, Saint Michaels, MD 21663

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    344 Perry Cabin Dr, Saint Michaels, MD 21663
  • /2

    $600,000

    Sold Aug 08, 2025

    901 S Talbot St, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft
    • Built 1930

    Last Sold Summary

    • $361/SF
    • 82 Days On Market

    Current Estimated Value $568,394

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, Saint Michaels, MD 21663
    • /53

      Est $355,911

      Not Listed For Sale

      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1986
      24345 Widgeon Place Unit 27, Saint Michaels, MD 21663

      Last Sold Summary

      • 18 Days On Market

  • /58

    $385,000

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

    24700 Deepwater Unit 20, Saint Michaels, MD 21663

    Situated in the established community of Martingham, 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, energy efficiency, and long-term durability. The redesigned open floor plan creates a seamless flow throughout the main living areas, complemented by updated

    Monica Penwell TTR Sotheby's International Realty

    24700 Deepwater Unit 20, Saint Michaels, MD 21663
  • /52

    $1,800,000

    Sold Nov 14, 2025

    23854 Mount Misery Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3.5 Baths
    • 4,012 Sq Ft
    • Built 1996

    Last Sold Summary

    • $449/SF
    • 1 Day On Market

    Current Estimated Value $1,803,591

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    23854 Mount Misery Rd, Saint Michaels, MD 21663
    • /18

      Est $363,853

      Not Listed For Sale

      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663

      • 2 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1978
      24580 Deepwater Point Dr Unit 7, Saint Michaels, MD 21663

      Last Sold Summary

      • 118 Days On Market

  • /43

    $600,000

    $30K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft

    9206 Martingham Dr, Saint Michaels, MD 21663

    NEW PRICE — EXCEPTIONAL VALUE IN DESIRABLE MARTINGHAM!Welcome to 9206 Martingham Drive, a truly distinctive contemporary residence offering spacious living with 4 bedrooms, 2 full and one half bathrooms, abundant natural light, and timeless architectural character in one of Saint Michaels' most sought-after communities. Competitively priced and thoughtfully designed, this unique home features

    Salar Hakimi Samson Properties

    9206 Martingham Dr, Saint Michaels, MD 21663
  • /33

    $236,000

    Sold Mar 31, 2026

    209 Webb Ln, Saint Michaels, MD 21663

    • 2 Beds
    • 1 Bath
    • 932 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Above List Price
    • $253/SF
    • 44 Days On Market

    Current Estimated Value $227,832

    Last Listing Agent Harry Kaiser Coldwell Banker Realty

    209 Webb Ln, Saint Michaels, MD 21663

Showing Results 41 - 80, Page 2 of 18

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