2,828

Saint Michaels, MD Homes

Section Image
    • /41

      Est $417,648

      Not Listed For Sale

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

      • 3 Beds
      • 2 Baths
      • 1,752 Sq Ft
      • Built 1973
      9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663

      Last Sold Summary

      • 33 Days On Market

  • /56

    $995,000

    • 3 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    101 Seymour Ave, Saint Michaels, MD 21663

    Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive

    Henry Gibbons-Neff Meredith Fine Properties

    101 Seymour Ave, Saint Michaels, MD 21663
  • /39

    $630,000

    Sold Oct 10, 2025

    9560 Martingham Cir, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,350 Sq Ft
    • Built 2000

    Last Sold Summary

    • $268/SF
    • 61 Days On Market

    Current Estimated Value $625,128

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

    9560 Martingham Cir, Saint Michaels, MD 21663
    • /65

      Est $339,993

      Not Listed For Sale

      9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663

      • 2 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1973
      9531 Quail Hollow Dr Unit 403, Saint Michaels, MD 21663

      Last Sold Summary

      • 221 Days On Market

  • /43

    $799,900

    $60K 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
  • /37

    $785,000

    Sold Apr 30, 2026

    24822 Swan Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,439 Sq Ft
    • Built 1982

    Last Sold Summary

    • 5% Below List Price
    • $322/SF
    • 9 Days On Market

    Current Estimated Value $798,867

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    24822 Swan Rd, Saint Michaels, MD 21663
    • /57

      Est $840,594

      Not Listed For Sale

      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft
      • Built 1990
      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663

      Last Sold Summary

      • 37 Days On Market

  • /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
  • /47

    $619,000

    Sold Oct 20, 2025

    231 Madison Ave, Saint Michaels, MD 21663

    • 2 Beds
    • 2 Baths
    • 1,702 Sq Ft
    • Built 1972

    Last Sold Summary

    • $364/SF
    • 18 Days On Market

    Current Estimated Value $592,287

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    231 Madison Ave, Saint Michaels, MD 21663
    • /48

      Est $846,310

      Not Listed For Sale

      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,135 Sq Ft
      • Built 1990
      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663

      Last Sold Summary

      • 53 Days On Market

  • /89

    $1,049,000

    $151K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    504 Seymour Ave, Saint Michaels, MD 21663

    This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200

    Barbara Watkins Benson & Mangold, LLC

    504 Seymour Ave, 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 $963,962

    Last Listing Agent Keith Hensley Meredith Fine Properties

    9792 Martingham Cir, Saint Michaels, MD 21663
    • /31

      Est $932,223

      Not Listed For Sale

      9792 Martingham Cir, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,213 Sq Ft
      • Built 1990
      9792 Martingham Cir, Saint Michaels, MD 21663

      Last Sold Summary

      • 5 Days On Market

  • /71

    $2,149,000

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

    7149 Drum Point Rd, Saint Michaels, MD 21663

    NEW PRICE DO NOT MISS THIS ONENestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7149 Drum Point Rd, Saint Michaels, MD 21663
  • /66

    $765,000

    Sold Jun 03, 2026

    24912 Back Creek Dr, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft
    • Built 2004

    Last Sold Summary

    • $242/SF
    • 162 Days On Market

    Current Estimated Value $784,022

    Last Listing Agent Kathleen Coale Benson & Mangold, LLC

    24912 Back Creek Dr, Saint Michaels, MD 21663
    • /51

      Est $917,536

      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

      • 22 Days On Market

  • /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
  • /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 $691,677

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    9235 Martingham Dr, Saint Michaels, MD 21663
    • /35

      Est $413,846

      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

      • 178 Days On Market

  • /70

    $795,000

    • 4 Beds
    • 3 Baths
    • 1,988 Sq Ft

    9359 Martingham Cir, Saint Michaels, MD 21663

    Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St.

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9359 Martingham Cir, 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 $329,128

    Last Listing Agent Amy Berry Meredith Fine Properties

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    • /75

      Est $365,090

      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

      • 78 Days On Market

  • /68

    $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
  • /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 $949,337

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

    100 Grace St, St. Michaels, MD 21663
    • /22

      Est $523,636

      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

      • 8 Days On Market

  • /68

    $1,679,000

    • 4 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    24390 Oakwood Park Rd, Saint Michaels, MD 21663

    Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square

    Janet Larson Benson & Mangold, LLC

    24390 Oakwood Park Rd, Saint Michaels, MD 21663
  • /57

    $1,395,000

    Sold Jun 22, 2026

    121 W Chestnut St, St. Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,540 Sq Ft
    • Built 1890

    Last Sold Summary

    • $549/SF
    • 1 Day On Market

    Current Estimated Value $1,379,326

    Last Listing Agent Carolina Barksdale Benson & Mangold, LLC

    121 W Chestnut St, St. Michaels, MD 21663
    • /47

      Est $831,442

      Not Listed For Sale

      24981 Back Creek Dr, Saint Michaels, MD 21663

      • 5 Beds
      • 3.5 Baths
      • 3,166 Sq Ft
      • Built 2006
      24981 Back Creek Dr, Saint Michaels, MD 21663

      Last Sold Summary

      • 4 Days On Market

  • /3

    $849,800

    Under Contract
    • 5 Beds
    • 4.5 Baths
    • 3,452 Sq Ft

    24896 Back Creek Dr, Saint Michaels, MD 21663

    Welcome to 24896 Back Creek Drive Saint Michaels, a coastal home with one of the most beautiful back yard pond views available in the entire community! This property has so much a buyer may desire--modern, coastal design, open concept living, soaring ceilings, a large fenced back yard, broad views of a beautiful pond, water access approx 0.2 miles down the community pathway to San Domingo Creek

    Tiffany Cloud Meredith Fine Properties

    24896 Back Creek Dr, 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 $629,092

    Last Listing Agent Ani Gonzalez-Brunet Coldwell Banker Realty

    204 W Chew Ave, Saint Michaels, MD 21663
    • /50

      Est $611,935

      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

      • 99 Days On Market

  • /40

    $374,000

    $11K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

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

    REDUCED CLEAN UNIT ...CASUAL LIVING IN SOUTH AFTER "THE LINK AT PERRY CABIN " MARTINGHAM COMMUNITY Nestled within the prestigious Quail Hollow community in desirable Martingham, this exceptional residence enjoys a prime setting overlooking the renowned Links at Perry Cabin golf course. One of the few units featuring a screened porch, this home offers the perfect blend of elegance, comfort,

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, 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 $742,205

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

    602 S Talbot St, Saint Michaels, MD 21663
    • /94

      Est $2,346,783

      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

      • 31 Days On Market

  • /2

    $459,900

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

    104 Madison Ave, Saint Michaels, MD 21663

    This well-maintained duplex 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 currently 100%

    Chuck Mangold Benson & Mangold, LLC

    104 Madison Ave, Saint Michaels, MD 21663
  • /89

    $2,680,000

    Sold Apr 10, 2026

    9262 Macks Ln, McDaniel, MD 21647

    • 4 Beds
    • 6 Baths
    • 5,400 Sq Ft
    • Built 2000

    Last Sold Summary

    • $496/SF
    • 151 Days On Market

    Current Estimated Value $2,595,368

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    9262 Macks Ln, McDaniel, MD 21647
    • /44

      Est $443,352

      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

      • 34 Days On Market

  • /54

    $749,000

    $76K 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
  • /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 $755,803

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    103 Mulberry St, Saint Michaels, MD 21663
    • /72

      Est $2,700,679

      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

      • 12 Days On Market

Showing Results 81 - 120, Page 3 of 18

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