2,828

Saint Michaels, MD Homes

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  • /6

    $779,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    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
  • /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

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

    9560 Martingham Cir, Saint Michaels, MD 21663
    • /75

      Est $390,945 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
  • /16

    $889,800 New Construction

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

    704 Meadow St, Saint Michaels, MD 21663

    Welcome to Saint Michaels. Located near the historic district, close to the harbor and 2 waterfront parks,and the numerous quaint shops and eating establishments as well as the museums. Lacrosse homes is proud to present The Midshore. This 4 bedroom 4.5 bath home with open floor plan is designed for everyday enjoyment or the perfect second home. Every bedroom has its own private bathroom. The

    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

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    231 Madison Ave, Saint Michaels, MD 21663
    • /34

      Est $408,980 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
  • /33

    $859,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,027 Sq Ft

    807 Radcliff Ave, Saint Michaels, MD 21663

    Home is currently under construction with an estimated completion date of Feb-March 2026. Photos are of a similar home with comparable finishes by the same builder. This 3BR, 2.5BA Arts & Crafts home sits on a quaint lot in beautiful Saint Michaels and will be clad with high end finishes throughout. The luxurious kitchen will feature stylish pistachio and linen shaker cabinetry with satin bronze

    Adam Ellison Long & Foster Real Estate, Inc.

    807 Radcliff 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 $782,606

    Last Listing Agent Kathleen Coale Benson & Mangold, LLC

    24989 Back Creek Dr, Saint Michaels, MD 21663
    • /22

      Est $520,444 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
  • /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
  • /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
    • /29

      Est $463,220 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
  • /40

    $1,635,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 4,102 Sq Ft

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Michaels Retreat—an extraordinary 6-acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and the Miles River. Just minutes from downtown Saint Michaels, this stunningly renovated residence offers over 4,100 sq. ft. of one-level living, thoughtfully designed for effortless indoor and outdoor entertaining. Inside, expansive

    Laura Carney TTR Sotheby's International Realty

    9171 Deepwater Point Rd, 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 $878,180

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

    402 Railroad Ave, Saint Michaels, MD 21663
    • /50

      Est $491,869 Not Listed For Sale

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

      10434 Claiborne Rd, Claiborne, MD 21624

      10434 Claiborne Rd, Claiborne, MD 21624
  • /4

    $895,000 Pending

    • Land
    • 2.73 Acres
    • $327,839 per Acre

    0 Bozman Neavitt Rd Unit MDTA2011976, Saint Michaels, MD 21663

    Discover the perfect blend of privacy and waterfront living on this exceptional 2.73-acre wooded lot along scenic Broad Creek. With approximately 219 feet of shoreline, this property offers endless opportunities to build your dream home or weekend retreat, complete with stunning water views and direct access for boating, fishing, or kayaking. Surrounded by mature trees, the setting provides both

    Chuck Mangold Benson & Mangold, LLC

    0 Bozman Neavitt Rd Unit MDTA2011976, 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 $403,661

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663
    • /94

      Est $2,182,295 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
  • /10

    $149,999

    • 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

    Tammy Durbin Long & Foster Real Estate, Inc.

    300 Perry 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
    • /44

      Est $460,096 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
  • /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
  • /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

    Last Listing Agent Ani Gonzalez-Brunet Coldwell Banker Realty

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

      Est $2,863,302 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
  • /36

    $499,000

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    105 Seymour Ave, Saint Michaels, MD 21663

    SAINT MICHAELS CHARMER! Welcome Home to this Cozy Cottage perfectly situated in the desirable, walkable Historic Town of St. Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. A sizable .25 Acre lot with mature trees, flower gardens and an inground pool potential are a rare commodity with "in-town" living! Step inside to find a

    Pamela Ackermann-Doll RE/MAX Executive

    105 Seymour Ave, Saint Michaels, MD 21663
  • /64

    $1,550,000 Sold Dec 20, 2024

    8288 Bozman Neavitt Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 3,282 Sq Ft
    • Built 1998

    Last Sold Summary

    • $472/SF
    • 189 Days On Market

    Current Estimated Value $1,577,589

    Last Listing Agent Debra Crouch Benson & Mangold, LLC

    8288 Bozman Neavitt Rd, Saint Michaels, MD 21663
    • /49

      Est $2,470,774 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
  • /44

    $499,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    207 Dodson Ave, Saint Michaels, MD 21663

    Fabulous 1910 Bungalow with welcoming front porch that has been renovated throughout. All main level living with beautiful primary suite offers room for king bed and ample closet space. Primary tiled bath offers luxury walk-in shower with sliding glass doors. Corner guest room with pocket door leading into guest bathroom. Living room has vaulted ceiling with skylight and opens to spacious dining

    Debra Crouch Benson & Mangold, LLC

    207 Dodson Ave, 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 $1,491,646

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    24256 Oakwood Park Rd, Saint Michaels, MD 21663
    • /79

      Est $2,021,062 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
  • /69

    $1,850,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 2,717 Sq Ft

    23869 New Land Dr, St. Michaels, MD 21663

    Welcome to Heron Cove Farm, a beautiful waterfront paradise situated on the banks of Broad Creek, just outside of Historic Saint Michaels, MD. This masterfully renovated home offers the convenience of one level living in a private setting of over 15 acres creating the feel of a peaceful escape, yet only two miles from the restaurants, shops and social network of town. Whether you enjoy relaxing

    Keith Hensley Meredith Fine Properties

    23869 New Land Dr, St. 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

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

    602 S Talbot St, Saint Michaels, MD 21663
    • /3

      Est $2,243,408 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
  • /6

    $999,000 New Construction

    • 3 Beds
    • 2.5 Baths

    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
  • /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 $788,462

    Last Listing Agent Tom Crouch Benson & Mangold, LLC

    103 Mulberry St, Saint Michaels, MD 21663
    • /32

      Est $1,595,490 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

    $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
  • /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

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

    320 Perry Cabin Dr, Saint Michaels, MD 21663
    • /43

      Est $1,909,607 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
  • /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

Showing Results 81 - 120, Page 3 of 18

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