2,833

Saint Michaels, MD Homes

Section Image
    • 9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
      /51

      Est $887,737 Not Listed For Sale

      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft
      • Built 1990
      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663

      Last Sold Summary

      • 8% Above List Price
      • $386/SF
      • 22 Days On Market

      Last Sold Price $825,000

      Last Listing Agent Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

  • 9791 Pintail Place, Saint Michaels, MD 21663
    9791 Pintail Place, Saint Michaels, MD 21663
    9791 Pintail Place, Saint Michaels, MD 21663
    /80

    $3,475,000 Under Contract

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

    9791 Pintail Place, Saint Michaels, MD 21663

    Welcome to Rivermark - a true waterfront retreat in St. Michaels on the Eastern Shore. This custom-built home is an artistic masterpiece with five octagonal interconnected wings, creating distinct yet flowing spaces and breathtaking panoramic views of Porters Creek, Miles River, Wye River and the Eastern Bay from every room.With architecture inspired by the French West Indies, this home

    Kathleen Eder Compass

    9791 Pintail Place, Saint Michaels, MD 21663
  • 24989 Back Creek Dr, Saint Michaels, MD 21663
    24989 Back Creek Dr, Saint Michaels, MD 21663
    24989 Back Creek Dr, Saint Michaels, MD 21663
    /40

    $795,000 Sold Jul 31, 2025

    24989 Back Creek Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 3,098 Sq Ft
    • Built 2006

    Last Sold Summary

    • $257/SF
    • 0 Days On Market

    Current Estimated Value $769,374

    Last Listing Agent Kathleen Coale Benson & Mangold, LLC

    24989 Back Creek Dr, Saint Michaels, MD 21663
    • 24362 Widgeon Place Unit 6, Saint Michaels, MD 21663
      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663
      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663
      /35

      Est $432,307 Not Listed For Sale

      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 1,752 Sq Ft
      • Built 1986
      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663

      Last Sold Summary

      • 1% Below List Price
      • $248/SF
      • 178 Days On Market

      Last Sold Price $435,000

      Last Listing Agent Skipper Marquess Coldwell Banker (NRT-Southeast-MidAtlantic)

  • 912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    /11

    $219,000

    • Land
    • 0.25 Acre
    • $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
  • 9792 Martingham Cir, Saint Michaels, MD 21663
    9792 Martingham Cir, Saint Michaels, MD 21663
    9792 Martingham Cir, Saint Michaels, MD 21663
    /39

    $965,000 Sold Jan 30, 2026

    9792 Martingham Cir, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,135 Sq Ft
    • Built 1990

    Last Sold Summary

    • 1% Below List Price
    • $452/SF
    • 12 Days On Market

    Current Estimated Value $940,609

    Last Listing Agent Keith Hensley Meredith Fine Properties

    9792 Martingham Cir, Saint Michaels, MD 21663
    • 24360 Widgeon Place Unit 11, Saint Michaels, MD 21663
      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663
      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663
      /75

      Est $387,245 Not Listed For Sale

      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1986
      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663

      Last Sold Summary

      • 1% Below List Price
      • $217/SF
      • 78 Days On Market

      Last Sold Price $390,000

      Last Listing Agent David Boutin RE/MAX

  • 24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    /66

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    24912 Back Creek Dr, Saint Michaels, MD 21663

    Back Creek Landing home for sale in St. Michaels, MD — located in one of the town’s most desirable neighborhoods, known for its peaceful setting, friendly community, and proximity to downtown St. Michaels. This home is just minutes away by bike or golf cart, offering easy access to shops, restaurants, the harbor, and waterfront activities while still feeling private and serene. This beautifully

    Kathleen Coale Benson & Mangold, LLC

    24912 Back Creek Dr, Saint Michaels, MD 21663
  • 9235 Martingham Dr, Saint Michaels, MD 21663
    9235 Martingham Dr, Saint Michaels, MD 21663
    9235 Martingham Dr, Saint Michaels, MD 21663
    /30

    $699,000 Sold Nov 13, 2025

    9235 Martingham Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,646 Sq Ft
    • Built 1995

    Last Sold Summary

    • $264/SF
    • 6 Days On Market

    Current Estimated Value $694,582

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    9235 Martingham Dr, Saint Michaels, MD 21663
    • 24375 Widgeon Place Unit 38, Saint Michaels, MD 21663
      24375 Widgeon Place Unit 38, Saint Michaels, MD 21663
      24375 Widgeon Place Unit 38, Saint Michaels, MD 21663
      /34

      Est $413,497 Not Listed For Sale

      24375 Widgeon Place Unit 38, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1986
      24375 Widgeon Place Unit 38, Saint Michaels, MD 21663

      Last Sold Summary

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

      Last Sold Price $430,000

      Last Listing Agent Larry Brennan TTR Sotheby's International Realty

  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /27

    $295,000

    • Land
    • 0.55 Acre
    • $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
  • 24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    /41

    $330,000 Sold Mar 17, 2026

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 1986

    Last Sold Summary

    • $183/SF
    • 136 Days On Market

    Current Estimated Value $346,870

    Last Listing Agent Amy Berry Meredith Fine Properties

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    • 526 Tenant Cir, Saint Michaels, MD 21663
      526 Tenant Cir, Saint Michaels, MD 21663
      526 Tenant Cir, Saint Michaels, MD 21663
      /22

      Est $519,507 Not Listed For Sale

      526 Tenant Cir, Saint Michaels, MD 21663

      • 3 Beds
      • 1 Bath
      • 1,216 Sq Ft
      • Built 1956
      526 Tenant Cir, Saint Michaels, MD 21663

      Last Sold Summary

      • 22% Above List Price
      • $350/SF
      • 8 Days On Market

      Last Sold Price $425,000

      Last Listing Agent Cornelia Heckenbach Long & Foster

  • 9262 Macks Ln, McDaniel, MD 21647
    9262 Macks Ln, McDaniel, MD 21647
    9262 Macks Ln, McDaniel, MD 21647
    /89

    $2,998,000 Pending

    • 4 Beds
    • 6 Baths
    • 5,400 Sq Ft

    9262 Macks Ln, McDaniel, MD 21647

    Just 5-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings

    Tom Crouch Benson & Mangold, LLC

    9262 Macks Ln, McDaniel, MD 21647
  • 100 Grace St, St. Michaels, MD 21663
    100 Grace St, St. Michaels, MD 21663
    100 Grace St, St. Michaels, MD 21663
    /46

    $1,000,000 Sold Feb 13, 2026

    100 Grace St, St. Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,445 Sq Ft
    • Built 1890

    Last Sold Summary

    • $692/SF
    • 28 Days On Market

    Current Estimated Value $1,089,391

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

    100 Grace St, St. Michaels, MD 21663
    • 10434 Claiborne Rd, Claiborne, MD 21624
      10434 Claiborne Rd, Claiborne, MD 21624
      10434 Claiborne Rd, Claiborne, MD 21624
      /50

      Est $487,692 Not Listed For Sale

      10434 Claiborne Rd, Claiborne, MD 21624

      • 4 Beds
      • 2 Baths
      • 2,880 Sq Ft
      • Built 1900
      10434 Claiborne Rd, Claiborne, MD 21624

      Last Sold Summary

      • 22% Above List Price
      • $139/SF
      • 99 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Darlene Wheatley Benson & Mangold, LLC

  • 23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    /82

    $3,100,000

    • 4 Beds
    • 3.5 Baths
    • 4,035 Sq Ft

    23961 Lynnewood Dr, Saint Michaels, MD 21663

    Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining

    Barbara Watkins Benson & Mangold, LLC

    23961 Lynnewood Dr, Saint Michaels, MD 21663
  • 402 Railroad Ave, Saint Michaels, MD 21663
    402 Railroad Ave, Saint Michaels, MD 21663
    402 Railroad Ave, Saint Michaels, MD 21663
    /50

    $875,000 Sold Mar 28, 2025

    402 Railroad Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,450 Sq Ft
    • Built 1900

    Last Sold Summary

    • $357/SF

    Current Estimated Value $881,381

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

    402 Railroad Ave, Saint Michaels, MD 21663
    • 24640 Yacht Club Rd, Saint Michaels, MD 21663
      24640 Yacht Club Rd, Saint Michaels, MD 21663
      24640 Yacht Club Rd, Saint Michaels, MD 21663
      /94

      Est $2,348,583 Not Listed For Sale

      24640 Yacht Club Rd, Saint Michaels, MD 21663

      • 10 Beds
      • 9.5 Baths
      • 6,433 Sq Ft
      • Built 1910
      24640 Yacht Club Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 16% Below List Price
      • $435/SF
      • 31 Days On Market

      Last Sold Price $2,800,000

      Last Listing Agent Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

  • 9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    /32

    $385,000

    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663

    Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled within the famous "links at Perry Cabin " , one of the few units with a screened porch . Enjoy the beautiful golf course views from the second floor, the first floor is private with its landscaping. Bathroom and kitchen countertops are granite, the kitchen has a space for a breakfast table, Living and dining

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
  • 106C Conner St, Saint Michaels, MD 21663
    106C Conner St, Saint Michaels, MD 21663
    106C Conner St, Saint Michaels, MD 21663
    /31

    $399,000 Sold Jul 18, 2025

    106C Conner St, Saint Michaels, MD 21663

    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1998

    Last Sold Summary

    • $369/SF
    • 157 Days On Market

    Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

    106C Conner St, Saint Michaels, MD 21663
    • 506 Railroad Ave, Saint Michaels, MD 21663
      506 Railroad Ave, Saint Michaels, MD 21663
      506 Railroad Ave, Saint Michaels, MD 21663
      /44

      Est $454,810 Not Listed For Sale

      506 Railroad Ave, Saint Michaels, MD 21663

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1972
      506 Railroad Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 1% Above List Price
      • $468/SF
      • 34 Days On Market

      Last Sold Price $449,000

      Last Listing Agent Monica Penwell TTR Sotheby's International Realty

  • 24749 Swan Rd, Saint Michaels, MD 21663
    24749 Swan Rd, Saint Michaels, MD 21663
    24749 Swan Rd, Saint Michaels, MD 21663
    /43

    $630,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,496 Sq Ft

    24749 Swan Rd, Saint Michaels, MD 21663

    This is a rare chance to secure meaningful savings and a beautiful home in one of the Eastern Shore’s most desirable communities.Welcome to Martingham—home to the newly redesigned Pete Dye course, The Links at Perry Cabin, and just minutes from the heart of historic St. Michaels. Enjoy world-class dining, boutique shopping, and waterfront charm, all right at your fingertips.Set on 1.13

    Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, Saint Michaels, MD 21663
  • 204 W Chew Ave, Saint Michaels, MD 21663
    204 W Chew Ave, Saint Michaels, MD 21663
    204 W Chew Ave, Saint Michaels, MD 21663
    /76

    $660,000 Sold Sep 16, 2025

    204 W Chew Ave, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1890

    Last Sold Summary

    • $440/SF
    • 4 Days On Market

    Current Estimated Value $664,679

    Last Listing Agent Ani Gonzalez-Brunet Coldwell Banker Realty

    204 W Chew Ave, Saint Michaels, MD 21663
    • 705 Riverview Terrace, Saint Michaels, MD 21663
      705 Riverview Terrace, Saint Michaels, MD 21663
      705 Riverview Terrace, Saint Michaels, MD 21663
      /72

      Est $2,767,031 Not Listed For Sale

      705 Riverview Terrace, Saint Michaels, MD 21663

      • 4 Beds
      • 4 Baths
      • 4,000 Sq Ft
      • Built 1960
      705 Riverview Terrace, Saint Michaels, MD 21663

      Last Sold Summary

      • 7% Below List Price
      • $742/SF
      • 12 Days On Market

      Last Sold Price $2,970,000

      Last Listing Agent Barbara Watkins Benson & Mangold, LLC

  • 24354 Widgeon Place Unit 20, Saint Michaels, MD 21663
    24354 Widgeon Place Unit 20, Saint Michaels, MD 21663
    24354 Widgeon Place Unit 20, Saint Michaels, MD 21663
    /57

    $350,000

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    24354 Widgeon Place Unit 20, Saint Michaels, MD 21663

    Widgeon Place is a charming townhome enclave within the desirable Martingham community, offering effortless comfort and nearly maintenance-free living. Just minutes from the historic waterfront town of St. Michaels, this home is ideally suited for year-round living, a relaxing weekend retreat, or a smart investment opportunity. Martingham overlooks the renowned Links at Perry Cabin Golf

    Monica Penwell TTR Sotheby's International Realty

    24354 Widgeon Place Unit 20, Saint Michaels, MD 21663
  • 24256 Oakwood Park Rd, Saint Michaels, MD 21663
    24256 Oakwood Park Rd, Saint Michaels, MD 21663
    /2

    $1,500,000 Sold Apr 29, 2025

    24256 Oakwood Park Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,702 Sq Ft
    • Built 1954

    Last Sold Summary

    • $555/SF
    • 18 Days On Market

    Current Estimated Value $1,476,140

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    24256 Oakwood Park Rd, Saint Michaels, MD 21663
    • 7920 Church Neck Rd, Saint Michaels, MD 21663
      7920 Church Neck Rd, Saint Michaels, MD 21663
      7920 Church Neck Rd, Saint Michaels, MD 21663
      /49

      Est $2,466,707 Not Listed For Sale

      7920 Church Neck Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 3.5 Baths
      • 4,825 Sq Ft
      • Built 1997
      7920 Church Neck Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 3% Below List Price
      • $528/SF

      Last Sold Price $2,550,000

      Last Listing Agent datacorrect BrightMLS Non Subscribing Office

  • 100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    /40

    $500,000

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

    100 Bush Terrace, Saint Michaels, MD 21663

    Welcome to easy Eastern Shore living in the charming waterfront town of St. Michaels! This 3-bedroom, 2 bath, 1,232 sq. ft. home is located in the desirable community of Rio Vista offering direct access to the Miles River, complete with a community dock, boat slips, and boat ramp — perfect for boating, crabbing, paddleboarding, or sunset cruises. Enjoy the relaxed coastal lifestyle just minutes

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    100 Bush Terrace, Saint Michaels, MD 21663
  • 602 S Talbot St, Saint Michaels, MD 21663
    602 S Talbot St, Saint Michaels, MD 21663
    602 S Talbot St, Saint Michaels, MD 21663
    /46

    $740,000 Sold Oct 02, 2025

    602 S Talbot St, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,433 Sq Ft
    • Built 1890

    Last Sold Summary

    • 33% Below List Price
    • $304/SF
    • 844 Days On Market

    Current Estimated Value $762,241

    Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

    602 S Talbot St, Saint Michaels, MD 21663
    • 7135 Solitude Rd, Saint Michaels, MD 21663
      7135 Solitude Rd, Saint Michaels, MD 21663
      7135 Solitude Rd, Saint Michaels, MD 21663
      /79

      Est $2,017,321 Not Listed For Sale

      7135 Solitude Rd, Saint Michaels, MD 21663

      • 4 Beds
      • 4.5 Baths
      • 3,200 Sq Ft
      • Built 1969
      7135 Solitude Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 6% Below List Price
      • $672/SF
      • 33 Days On Market

      Last Sold Price $2,150,000

      Last Listing Agent Eugene Smith TTR Sotheby's International Realty

  • 113 Gloria Ave, Saint Michaels, MD 21663
    113 Gloria Ave, Saint Michaels, MD 21663
    113 Gloria Ave, Saint Michaels, MD 21663
    /36

    $615,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    113 Gloria Ave, Saint Michaels, MD 21663

    Situated on a corner lot just minutes from downtown St. Michaels, this 3-bedroom, 2-bath home offers easy access to local shops, restaurants, and the Maritime Museum. Inside, the living room is filled with natural light from a large bay window and features LVP flooring, recessed lighting, and updated fixtures throughout. The kitchen and dining area provide an open, functional layout with direct

    Peter Stark Benson & Mangold, LLC

    113 Gloria Ave, 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

    $800,000 Sold Aug 15, 2025

    103 Mulberry St, Saint Michaels, MD 21663

    • 4 Beds
    • 1.5 Baths
    • 1,596 Sq Ft
    • Built 1860

    Last Sold Summary

    • $501/SF
    • 149 Days On Market

    Current Estimated Value $771,825

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    103 Mulberry St, Saint Michaels, MD 21663
    • 24519 New Post Rd, Saint Michaels, MD 21663
      24519 New Post Rd, Saint Michaels, MD 21663
      24519 New Post Rd, Saint Michaels, MD 21663
      /3

      Est $2,129,995 Not Listed For Sale

      24519 New Post Rd, Saint Michaels, MD 21663

      • 4 Beds
      • 3.5 Baths
      • 2,881 Sq Ft
      • Built 2001
      24519 New Post Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 1% Above List Price
      • $729/SF
      • 0 Days On Market

      Last Sold Price $2,100,000

      Last Listing Agent Amy Berry Meredith Fine Properties

  • 101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    /19

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    101 Brooks Ln, Saint Michaels, MD 21663

    Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‐level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced

    Stacie Luhrman Benson & Mangold, LLC

    101 Brooks Ln, Saint Michaels, MD 21663
  • 320 Perry Cabin Dr, Saint Michaels, MD 21663
    320 Perry Cabin Dr, Saint Michaels, MD 21663
    320 Perry Cabin Dr, Saint Michaels, MD 21663
    /16

    $1,000,000 Sold Oct 08, 2025

    320 Perry Cabin Dr, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,557 Sq Ft
    • Built 1988

    Last Sold Summary

    • $642/SF
    • 1 Day On Market

    Current Estimated Value $1,048,102

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

    320 Perry Cabin Dr, Saint Michaels, MD 21663
    • 8726 Mount Pleasant Ct, Saint Michaels, MD 21663
      8726 Mount Pleasant Ct, Saint Michaels, MD 21663
      8726 Mount Pleasant Ct, Saint Michaels, MD 21663
      /32

      Est $1,561,449 Not Listed For Sale

      8726 Mount Pleasant Ct, Saint Michaels, MD 21663

      • 2 Beds
      • 2 Baths
      • 2,152 Sq Ft
      • Built 1976
      8726 Mount Pleasant Ct, Saint Michaels, MD 21663

      Last Sold Summary

      • 10% Above List Price
      • $662/SF
      • 0 Days On Market

      Last Sold Price $1,425,000

      Last Listing Agent Angela Simonelli Compass

  • 24645 Long Haul Rd, Saint Michaels, MD 21663
    24645 Long Haul Rd, Saint Michaels, MD 21663
    24645 Long Haul Rd, Saint Michaels, MD 21663
    /112

    $2,900,000

    • 4 Beds
    • 4.5 Baths
    • 3,677 Sq Ft

    24645 Long Haul Rd, Saint Michaels, MD 21663

    Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for

    Donna Dickinson Coldwell Banker Realty

    24645 Long Haul Rd, Saint Michaels, MD 21663
  • 207 Seymour Ave, Saint Michaels, MD 21663
    207 Seymour Ave, Saint Michaels, MD 21663
    207 Seymour Ave, Saint Michaels, MD 21663
    /38

    $800,000 Sold Nov 17, 2025

    207 Seymour Ave, Saint Michaels, MD 21663

    • 4 Beds
    • 3.5 Baths
    • 1,983 Sq Ft
    • Built 1949

    Last Sold Summary

    • $403/SF
    • 17 Days On Market

    Current Estimated Value $792,518

    Last Listing Agent Larry Brennan TTR Sotheby's International Realty

    207 Seymour Ave, Saint Michaels, MD 21663
    • 1015 Riverview Terrace, Saint Michaels, MD 21663
      1015 Riverview Terrace, Saint Michaels, MD 21663
      1015 Riverview Terrace, Saint Michaels, MD 21663
      /43

      Est $1,816,144 Not Listed For Sale

      1015 Riverview Terrace, Saint Michaels, MD 21663

      • 5 Beds
      • 4 Baths
      • 3,301 Sq Ft
      • Built 1958
      1015 Riverview Terrace, Saint Michaels, MD 21663

      Last Sold Summary

      • 3% Below List Price
      • $568/SF
      • 24 Days On Market

      Last Sold Price $1,875,000

      Last Listing Agent Laura Carney TTR Sotheby's International Realty

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