2,830

Saint Michaels, MD Homes

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  • /16

    $889,800 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    704 Meadow St, Saint Michaels, MD 21663

    Fabulous St. Michaels location near Miles River, St. Michaels Marina, Inn & Spa, St, Michael’s Winery, area schools and so much more! Enjoy all the benefits of a coastal lifestyle in this charming & scenic historic town. Build your dream home on a attractive homesite minutes from everything and everywhere you want to be.The Pointe offers an impressive open kitchen with island, pantry and

    George Bailey Keller Williams Flagship

    704 Meadow St, 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 $613,650

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    231 Madison Ave, Saint Michaels, MD 21663
    • /51

      Est $809,430 Not Listed For Sale

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

      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663

      9792 Martingham Cir Unit 8, Saint Michaels, MD 21663
  • /44

    $549,900

    • 3 Beds
    • 2.5 Baths
    • 1,922 Sq Ft

    228 Tyler Ave, Saint Michaels, MD 21663

    This handsome home is nestled in the trees on a quiet cul de sac in Rio Vista. This popular neighborhood is five minutes from historic St. Michaels and offers public sewer and water with no town taxes. Rio Vista has a waterfront picnic area and boat slips for rent to residents for $225 per slip.This home has been very nicely maintained by the original owner. It offers one-level living, with a

    Debra Crouch Benson & Mangold, LLC

    228 Tyler Ave, 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 $782,963

    Last Listing Agent Kathleen Coale Benson & Mangold, LLC

    24989 Back Creek Dr, Saint Michaels, MD 21663
    • /35

      Est $440,215 Not Listed For Sale

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

      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663

      24362 Widgeon Place Unit 6, Saint Michaels, MD 21663
  • /57

    $470,000 Under Contract

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

    9529 Quail Hollow Dr Unit 504, Saint Michaels, MD 21663

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    9529 Quail Hollow Dr Unit 504, 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

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    9235 Martingham Dr, Saint Michaels, MD 21663
    • /75

      Est $385,993 Not Listed For Sale

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

      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663

      24360 Widgeon Place Unit 11, Saint Michaels, MD 21663
  • /10

    $149,999 Under Contract

    • Land
    • 0.14 Acre
    • $1,071,421 per Acre

    300 Perry St, Saint Michaels, MD 21663

    New price!...Great opportunity to own a buildable lot in one of Maryland's most charming waterfront towns. This spacious and level parcel offers the perfect canvas for your Eastern shore home. Nestled just blocks from the harbor, shops, restaurants, parks, marinas, and the Chesapeake Bay Maritime Museum. Walk to downtown restaurants and shops! The property combines small-town walkability with

    Tammy Durbin Long & Foster Real Estate, Inc.

    300 Perry St, 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 $881,154

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

    402 Railroad Ave, Saint Michaels, MD 21663
    • /34

      Est $405,599 Not Listed For Sale

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

      24375 Widgeon Place Unit 38, Saint Michaels, MD 21663

      24375 Widgeon Place Unit 38, 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
  • /28

    $395,000 Sold Feb 03, 2025

    9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 1973

    Last Sold Summary

    • $219/SF
    • 119 Days On Market

    Current Estimated Value $403,467

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663
    • /22

      Est $513,569 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,216 Sq Ft

      526 Tenant Cir, Saint Michaels, MD 21663

      526 Tenant Cir, Saint Michaels, MD 21663
  • /70

    $749,999

    • 4 Beds
    • 3.5 Baths
    • 3,010 Sq Ft

    24977 Back Creek Dr, Saint Michaels, MD 21663

    Discover a beautifully crafted custom home tucked within the peaceful St. Michaels community, where refined design meets everyday comfort. This exceptional residence offers 4 generously sized bedrooms and 3.5 thoughtfully designed bathrooms, filled with premium details throughout. The versatile gas fireplace anchors the inviting main living space, complemented by custom built-ins that add both

    Eddie Mangold Benson & Mangold, LLC

    24977 Back Creek Dr, 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
    • /29

      Est $480,602 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,552 Sq Ft

      924 Calvert Ave, Saint Michaels, MD 21663

      924 Calvert Ave, Saint Michaels, MD 21663
  • /34

    $749,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,518 Sq Ft

    23869 Mount Misery Rd, Saint Michaels, MD 21663

    Enjoy water-privileged living just minutes from downtown St. Michaels. This beautifully maintained one-level home sits on a well manicured lot directly across from the community’s waterfront parcel, offering water views and easy water access. A welcoming front porch leads into a bright foyer and on to the living room, featuring vaulted ceilings, hardwood floors and a gas fireplace. The kitchen

    Kim Crouch Ozman Benson & Mangold, LLC

    23869 Mount Misery Rd, 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 $660,577

    Last Listing Agent Ani Gonzalez-Brunet Coldwell Banker Realty

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

      Est $497,509 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,880 Sq Ft

      10434 Claiborne Rd, Claiborne, MD 21624

      10434 Claiborne Rd, Claiborne, MD 21624
  • /25

    $999,000 New Construction

    • 3 Beds
    • 2.5 Baths

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, 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 $1,490,202

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    24256 Oakwood Park Rd, Saint Michaels, MD 21663
    • /94

      Est $2,214,981 Not Listed For Sale

      • 10 Beds
      • 9.5 Baths
      • 6,433 Sq Ft

      24640 Yacht Club Rd, Saint Michaels, MD 21663

      24640 Yacht Club Rd, Saint Michaels, MD 21663
  • /37

    $479,999 Pending

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

    216 Brooks Ln, Saint Michaels, MD 21663

    Welcome to your future home in the heart of St. Michaels! Currently under construction, this brand-new rancher will showcase modern design and quality craftsmanship throughout. Featuring 3 spacious bedrooms and 2 full bathrooms, this single-level home is designed for comfort and convenience. Step inside to find beautiful LVP flooring, a large trim package, and a bright open layout. The kitchen

    Chance Stem LPT Realty, LLC

    216 Brooks Ln, 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 $757,770

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

    602 S Talbot St, Saint Michaels, MD 21663
    • /44

      Est $466,150 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft

      506 Railroad Ave, Saint Michaels, MD 21663

      506 Railroad Ave, Saint Michaels, MD 21663
  • /9

    $200,000

    • Land
    • 8.03 Acres
    • $24,907 per Acre

    00 New Rd, McDaniel, MD 21647

    8.037 Acres located just west of St. Michaels, MD. All wooded and has been used primarily for hunting and fire wood. There is one and possibly two approved perc sites though they may need to be updated. Access off of New Road and Walkers Turn road, there may be an opportunity to subdivide but would need to be discussed with County Planning and Zoning. Opportunity to build your home with a lot of

    James Bent Benson & Mangold, LLC

    00 New Rd, McDaniel, MD 21647
  • /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 $782,499

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

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

      Est $2,781,145 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 4,000 Sq Ft

      705 Riverview Terrace, Saint Michaels, MD 21663

      705 Riverview Terrace, 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 $1,026,365

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

    320 Perry Cabin Dr, Saint Michaels, MD 21663
    • /49

      Est $2,429,368 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 4,825 Sq Ft

      7920 Church Neck Rd, Saint Michaels, MD 21663

      7920 Church Neck Rd, 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

    Last Listing Agent Larry Brennan TTR Sotheby's International Realty

    207 Seymour Ave, Saint Michaels, MD 21663
    • /79

      Est $2,092,041 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,200 Sq Ft

      7135 Solitude Rd, Saint Michaels, MD 21663

      7135 Solitude Rd, Saint Michaels, MD 21663
  • /54

    $825,000 Sold Oct 28, 2025

    24312 Oakwood Park Rd, Saint Michaels, MD 21663

    • 2 Beds
    • 1 Bath
    • 836 Sq Ft
    • Built 1952

    Last Sold Summary

    • $987/SF
    • 25 Days On Market

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

    24312 Oakwood Park Rd, Saint Michaels, MD 21663
    • /3

      Est $2,146,785 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,881 Sq Ft

      24519 New Post Rd, Saint Michaels, MD 21663

      24519 New Post Rd, Saint Michaels, MD 21663
  • /53

    $750,000 Sold Mar 28, 2025

    24393 Widgeon Place, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,459 Sq Ft
    • Built 1973

    Last Sold Summary

    • $305/SF
    • 11 Days On Market

    Current Estimated Value $753,490

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

    24393 Widgeon Place, Saint Michaels, MD 21663
    • /32

      Est $1,663,980 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 2,152 Sq Ft

      8726 Mount Pleasant Ct, Saint Michaels, MD 21663

      8726 Mount Pleasant Ct, Saint Michaels, MD 21663
  • /37

    $472,500 Sold Mar 18, 2025

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

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • Built 1995

    Last Sold Summary

    • $262/SF
    • 18 Days On Market

    Current Estimated Value $473,712

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    • /43

      Est $1,819,488 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,301 Sq Ft

      1015 Riverview Terrace, Saint Michaels, MD 21663

      1015 Riverview Terrace, Saint Michaels, MD 21663

Showing Results 81 - 120, Page 3 of 18

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