2,823

Saint Michaels, MD Homes

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  • /47

    $765,000 Sold May 19, 2025

    • 3,166 Sq Ft
    • $242/SF
    • 4 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2006

    24981 Back Creek Dr, Saint Michaels, MD 21663

    Fabulous 5 bedrooms, 3.5 bath home with sought after floorplan, a spacious screened porch and deck located in the desirable Back Creek Landing neighborhood on the Easton side of St. Michaels with 40 acres of community areas, trails, ponds, and water access to San Domingo Creek. The wooded rear yard offers privacy with easy access to trails, community areas, and water access kayak pier. The

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24981 Back Creek Dr, Saint Michaels, MD 21663
    • /14

      Est $264,277 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      313 Dodson Ave, Saint Michaels, MD 21663

      313 Dodson Ave, Saint Michaels, MD 21663
  • /40

    $1,295,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,320 Sq Ft

    204 Mulberry St, Saint Michaels, MD 21663

    Step into history at the Thomas-Kirby House (c.1860), a charming renovated colonial in the heart of town with picturesque street views toward Saint Michaels Harbor. This light-filled historic residence showcases beautiful hardwood floors, two staircases, detailed millwork, and rich wood accents throughout. The welcoming foyer with its 'Seaport' hand painted mural wallpaper opens to a cozy study

    Laura Carney TTR Sotheby's International Realty

    204 Mulberry St, Saint Michaels, MD 21663
  • /18

    $1,310,000 Sold May 16, 2025

    • 2,654 Sq Ft
    • $494/SF
    • 2 Beds
    • 2 Baths
    • Built 1900

    104 W Chew Ave, Saint Michaels, MD 21663

    Sited on an unusually spacious 9000 square foot lot, this beautifully-restored c. 1900 home combines the best of historic charm with a modern, open floor plan. With heart pine floors throughout, three fireplaces, and lots of light, the home is warm and welcoming. During renovation, the house was raised and a new foundation was put in place. The yard is extensively landscaped and there is a large

    datacorrect BrightMLS Non Subscribing Office

    104 W Chew Ave, Saint Michaels, MD 21663
    • /57

      Est $779,980 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,069 Sq Ft

      909 Riverview Terrace, Saint Michaels, MD 21663

      909 Riverview Terrace, Saint Michaels, MD 21663
  • /47

    $619,000 Pending

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

    231 Madison Ave, Saint Michaels, MD 21663

    Welcome to 231 Madison Avenue, a beautifully renovated one-level home located in the water access community of Rio Vista, just minutes from downtown historic St. Michaels. Offering 2 bedrooms and 2 full baths, this home has been thoughtfully updated throughout, combining modern design with classic design in this rancher. With its open floor plan, the heart of the home is the gourmet kitchen

    Monica Penwell TTR Sotheby's International Realty

    231 Madison Ave, Saint Michaels, MD 21663
  • /72

    $2,325,000 Sold May 09, 2025

    • 3,732 Sq Ft
    • $623/SF
    • 6 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1954

    103 N Harbor Rd, Saint Michaels, MD 21663

    Breathtaking views of the Miles River and Chesapeake Bay Maritime Museum. Once in a lifetime opportunity to buy a solidly built home on almost an acre, within a few short blocks of downtown historic St. Michaels. Located on the harbor and close to restaurants and shopping. This 4 bedroom home is currently undergoing renovations. The kitchen has cherry cabinets, Wolf appliances, Fisher&

    Barbara Watkins Benson & Mangold, LLC

    103 N Harbor Rd, Saint Michaels, MD 21663
    • /106

      Est $859,708 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,289 Sq Ft

      24993 Back Creek Dr, Saint Michaels, MD 21663

      24993 Back Creek Dr, Saint Michaels, MD 21663
  • /54

    $825,000 Pending

    • 2 Beds
    • 1 Bath
    • 836 Sq Ft

    24312 Oakwood Park Rd, Saint Michaels, MD 21663

    Dappled in shade along the tranquil shores of San Domingo Creek, this picturesque Oakwood Park cottage is a serene waters-edge haven blending refined renewal with carefree charm. Originally constructed in 1952 and reimagined from its frame in 2024, the home’s tailored Eastern Shore character boasts 836 square feet of soft hues, wide-planked floors, and finishes of delightful simplicity. Within,

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24312 Oakwood Park Rd, Saint Michaels, MD 21663
  • /53

    $547,000 Sold May 09, 2025

    • 2,652 Sq Ft
    • $206/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    23203 Stewart Way, McDaniel, MD 21647

    Don't miss this charming, light filled 3BR, 2 1/2 BA spacious Cape Cod situated in its own wooded wonderland on more than 3 acres down a private road. Nestled in the trees on a quiet lane, this welcoming home greets you with a gorgeous front porch. The Large Living room with fireplace opens to the spacious kitchen with large island with granite countertops leading to a screened porch and deck

    Becky Wibberley Coldwell Banker Realty

    23203 Stewart Way, McDaniel, MD 21647
    • /38

      Est $818,389 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,781 Sq Ft

      115 W Chew Ave, Saint Michaels, MD 21663

      115 W Chew Ave, Saint Michaels, MD 21663
  • /3

    $299,000 Pending

    • Land
    • 2 Acres
    • $149,500 per Acre

    0 Pea Neck Rd Map 32 Parcel 76 Lot 2, Saint Michaels, MD 21663

    Incredible opportunity to build just minutes from downtown Saint Michaels. Public Sewer hookup is available. Buyer will be responsible for paying for hookupThis property was just sub divided and recorded. The property is 7841 Pea Neck Rd tax Map 32 Parcel 76 Lot 2. 2 acre lot. Public sewer hookup is available. One acre of the property is in forest conservation. Plat is available.

    Dennis Covey Meredith Fine Properties

    0 Pea Neck Rd Map 32 Parcel 76 Lot 2, Saint Michaels, MD 21663
  • /12

    $140,000 Sold May 09, 2025

    • Land
    • 0.21 Acre
    • $666,667 per Acre
    • 247 Days On Market

    226 North St, Saint Michaels, MD 21663

    40K PRICE REDUCTION! New Survey and Setback Requirements in document section of listing! Ready to build your custom home in the beautiful town of St. Michaels! PROPERTY IS UNDER R-1 and ALLOWS FOR A DUPLEX IF DESIRED. This is a larger lot, over 1/5 of an acre. Enjoy all the benefits of living in town, walk to the harbor, shops, restaurants, nature trail, library, ball park, community center

    Jennifer Pogoda Chesapeake Bay Real Estate Plus, LLC

    226 North St, Saint Michaels, MD 21663
    • /46

      Est $692,578 Not Listed For Sale

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

      220 Tyler Ave, Saint Michaels, MD 21663

      220 Tyler Ave, Saint Michaels, MD 21663
  • /52

    $1,695,000 Under Contract

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

    23854 Mount Misery Rd, Saint Michaels, MD 21663

    "Whispering Pines" A beautiful waterfront escape on private 2.75 +/- acre lot located within walking and biking distance from historic downtown St Michaels. Spacious, light and airy 4000+ sq foot 3BR 3BA home, custom built in 1996 boasts a desirable large, entry-level, primary suite, 2 en-suite bathrooms upstairs, spacious family room with cathedral ceiling and cozy wood burning fireplace, open

    Brian Petzold Benson & Mangold, LLC

    23854 Mount Misery Rd, Saint Michaels, MD 21663
  • /40

    $739,000 Sold May 02, 2025

    • 2,948 Sq Ft
    • $251/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    919 Riverview Terrace, Saint Michaels, MD 21663

    Located just outside the Town limits of St. Michaels on a very popular street (Riverview Terrace), this attractive 2,948 sq. ft. home was constructed in 2005. Outstanding floor plan is a combination of open and traditional, with a large kitchen/breakfast room/family room combination w/vaulted ceiling and lots of glass to capture the views across the private, landscaped back yard. The downstairs

    Tom Crouch Benson & Mangold, LLC

    919 Riverview Terrace, Saint Michaels, MD 21663
    • /10

      Est $394,670 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 920 Sq Ft

      209 E Maple Ave, Saint Michaels, MD 21663

      209 E Maple Ave, Saint Michaels, MD 21663
  • /57

    $780,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 2,068 Sq Ft

    106 Grace St, Saint Michaels, MD 21663

    Grace and Gratitude perfectly describe this charming historic home on Grace Street in the heart of St. Michaels! Grace St. is one of the few streets in town that isn't a through street to traffic. It starts at Talbot St & "Restaurant Row" & ends at the waterfront & walking trail off San Domingo Creek. The cozy front porch & classic Eastern Shore red front door are a prelude to the delightful

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    106 Grace St, Saint Michaels, MD 21663
  • /14

    $226,000 Sold Apr 30, 2025

    • 1,000 Sq Ft
    • $226/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1981

    315 Dodson Ave, Saint Michaels, MD 21663

    Do not miss this rancher style home in the town of St Michaels. This home offers over 1000 sq ft of living space and has an abundance of natural light. Featuring spacious living room that leads to the kitchen-dining combo and appliances, 3 bedrooms that provide privacy and relaxation, and a full bathroom. The outdoor space displays practical features such as a storage shed, driveway and widefront

    Gina Gargeu Century 21 Downtown

    315 Dodson Ave, Saint Michaels, MD 21663
    • /43

      Est $883,467 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,452 Sq Ft

      24896 Back Creek Dr, Saint Michaels, MD 21663

      24896 Back Creek Dr, Saint Michaels, MD 21663
  • /41

    $495,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    25028 Maplewood Dr, Saint Michaels, MD 21663

    Nestled on a quiet cul-de-sac just outside the picturesque waterfront town of St. Michaels, this beautifully renovated 3 bedroom 2.5-bath traditional Cape Cod home has transformed classic charm with modern luxury. Every detail has been thoughtfully updated beginning with the wood floors and carry through the new kitchen and baths. The stunning contemporary kitchen includes new appliances,,

    Monica Penwell TTR Sotheby's International Realty

    25028 Maplewood Dr, Saint Michaels, MD 21663
  • /2

    $1,500,000 Sold Apr 29, 2025

    • 2,702 Sq Ft
    • $555/SF
    • 18 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1954

    24256 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to your private retreat just moments to the charming, historic town of St. Michaels. This stunning, light- filled home boasts a perfect blend of elegance and comfort, complete with thoughtfully designed custom details throughout. Magnificent views overlooking San Domingo Creek from every room. Enjoy a waterside first floor primary suite with totally renovated ensuite bathroom with quartz

    Barbara Watkins Benson & Mangold, LLC

    24256 Oakwood Park Rd, Saint Michaels, MD 21663
    • /7

      Est $443,648 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 844 Sq Ft

      200 E Marengo St, Saint Michaels, MD 21663

      200 E Marengo St, Saint Michaels, MD 21663
  • /56

    $625,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    510 Tenant Cir, Saint Michaels, MD 21663

    major price reduction!! Motivated seller! Location! You really can’t beat this spot! Just head a few houses left and you’ll hit the Rio Vista waterfront park on the beautiful Miles River. Go a few houses to the right and you’re at the Rio Vista community dock—super handy if you have a boat. With this water-privileged location, you get easy access to both the park and the dock. This place has

    Larry Brennan TTR Sotheby's International Realty

    510 Tenant Cir, Saint Michaels, MD 21663
  • /75

    $1,100,000 Sold Apr 24, 2025

    • 2,548 Sq Ft
    • $432/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1817

    113 W Chestnut St, Saint Michaels, MD 21663

    Nestled in the heart of the historic town of St. Michaels, this enchanting 3-bedroom, 2-1/2 baths historic home offers the perfect blend of modern comfort and timeless charm. Do not miss this rare opportunity to own a piece of St. Michaels' rich history. Whether you are seeking a weekend getaway or a forever home, 113 W Chestnut Street is a true gem on one of the most desirable and beautiful

    Carolina Barksdale Benson & Mangold, LLC

    113 W Chestnut St, Saint Michaels, MD 21663
    • /45

      Est $529,161 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,080 Sq Ft

      23201 Stewart Way, McDaniel, MD 21647

      23201 Stewart Way, McDaniel, MD 21647
  • /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
  • /59

    $855,000 Sold Apr 17, 2025

    • 1,790 Sq Ft
    • $478/SF
    • 36 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1955

    23014 Claiborne Landing Rd, Claiborne, MD 21624

    Welcome to the charming village of Claiborne. This house was once the ticket office for the old ferries that carried people and farm goods from ports on Chesapeake Bay. Remnants of the old railroad are found on the northside of the property. The cottage faces west over Eastern Bay. Private dock, rip-rapped shoreline and year-round sunsets, large trees and a patio with hot tub to entertain.

    Ray Stevens Benson & Mangold, LLC

    23014 Claiborne Landing Rd, Claiborne, MD 21624
    • /46

      Est $836,415 Not Listed For Sale

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

      24912 Back Creek Dr, Saint Michaels, MD 21663

      24912 Back Creek Dr, Saint Michaels, MD 21663
  • /41

    $1,995,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 3,562 Sq Ft

    7369 Drum Point Rd, Saint Michaels, MD 21663

    This brick, French Provincial home is ideally situated minutes from downtown St. Michaels and rests on 4.8 acres along Barrett Cove off Edge Creek and the scenic Choptank River. This serene retreat boasts over 500 feet of riprapped shoreline, a kayak launch, and dock with 2.5'+ MLW and an electric boat lift.The bright and airy main house offers the ease of one-level living. The primary

    Clifford Meredith Meredith Fine Properties

    7369 Drum Point Rd, Saint Michaels, MD 21663
  • /53

    $750,000 Sold Mar 28, 2025

    • 2,459 Sq Ft
    • $305/SF
    • 11 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1973

    24393 Widgeon Place, Saint Michaels, MD 21663

    ONE STORY LIVING ON PARK LIKE SETTING CORNER LOT SURROUNDED BY THE PRESTIGEOUS LINKS AT PERRY CABIN AND JUST 5 MINUTES TO HISTORIC ST MICHAELS.THIS HOME FEATURES LOTS OF WINDOWS , TREES FILTERING THE BRIGHT SUNLIGHT, OPEN THE SLIDING DOOR AND STEP OUT TO SIT BY THE FIRE PIT AND ENJOY THE BEAUTIFUL LANDSCAPED GROUNDS. THERE IS A 4 SEASON SUNROOM TO ENJOY THE OUTDOORS IN COLDER WEATHER. THE

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24393 Widgeon Place, Saint Michaels, MD 21663
    • /34

      Est $938,422 Not Listed For Sale

      • 3 Beds
      • 5 Baths
      • 2,497 Sq Ft

      23863 Mount Misery Rd, Saint Michaels, MD 21663

      23863 Mount Misery Rd, Saint Michaels, MD 21663
  • /28

    $439,999 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,505 Sq Ft

    25070 Hurley Ln, Saint Michaels, MD 21663

    HUGE PRICE DROP in St. MIchaels! This gorgeous home just became an unbeatable deal in one of Marylands most charming waterfront towns! Don't miss your chance! This stunning 3-Bedroom, 2.5 Bath home nestled in a tranquil, private cul-de-sac in a charming St. Michaels neighborhood. Be dazzled by the 30 foot vaulted ceiling, loft overlook and wood burning Fireplace. This beautifully maintained

    Stephany Barrett Long & Foster Real Estate, Inc.

    25070 Hurley Ln, Saint Michaels, MD 21663
  • /50

    $875,000 Sold Mar 28, 2025

    • 2,450 Sq Ft
    • $357/SF
    • 3 Beds
    • 3 Baths
    • Built 1900

    402 Railroad Ave, Saint Michaels, MD 21663

    FABULOUS IN TOWN SPACIOUS CORNER LOT PROVIDES MANY EXPANSION OPTIONS. FULLY FENCED BACKYARD , LARGE INGROUND POOL, HOT TUB, AL FRESCO DINING ON THE PATIO WITH FIREPIT. 1 CAR GARAGE WITH STORAGE OPTIONS, MULTIPLE OFF STREET PARKING SPACES, PRIVATE GRAVEL DRIVEWAY, RAISED GARDEN BEDS.VERY UNIQUE OPPORTUNITY TO OWN THIS LIGHT FILLED HISTORIC VICTORIAN WITH 9 FOOT CEILINGS ON THE 1 ST FLOOR AND

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    402 Railroad Ave, Saint Michaels, MD 21663
    • /49

      Est $969,294 Not Listed For Sale

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

      114 E Chew Ave, Saint Michaels, MD 21663

      114 E Chew Ave, Saint Michaels, MD 21663
  • /37

    $472,500 Sold Mar 18, 2025

    • 1,800 Sq Ft
    • $262/SF
    • 18 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1995

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

    Located in the highly desirable Martingham community of Quail Hollow, this beautifully renovated 3-bedroom, 3-bath townhome is move-in ready after extensive updates between 2022 and 2024. The main level features stunning wood flooring throughout, a spacious great room with a gas fireplace, built-ins, and access to a peaceful rear patio that backs to open space.. The completely remodeled kitchen

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    • /48

      Est $1,715,400 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,694 Sq Ft

      201 E Chew Ave, Saint Michaels, MD 21663

      201 E Chew Ave, Saint Michaels, MD 21663
  • /44

    $1,833,000 Sold Mar 14, 2025

    • 2,670 Sq Ft
    • $687/SF
    • 1 Day On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1982

    7930 Church Neck Rd, Saint Michaels, MD 21663

    Welcome to "Point of View" – Your Waterfront Sanctuary in St. Michaels, MD! Discover the perfect blend of elegance and tranquility in this stunning coastal-style home nestled on 4+/- acres with 220 feet of riprapped shoreline along picturesque Broad Creek. Boasting breathtaking southwesterly views and designed to capture the essence of serene waterfront living, this property is a rare gem in a

    Monica Penwell TTR Sotheby's International Realty

    7930 Church Neck Rd, Saint Michaels, MD 21663
    • /76

      Est $771,759 Not Listed For Sale

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

      24997 Back Creek Dr, Saint Michaels, MD 21663

      24997 Back Creek Dr, Saint Michaels, MD 21663
  • /80

    $900,000 Sold Feb 28, 2025

    • 5,869 Sq Ft
    • $153/SF
    • 9 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1960

    8080 Bozman Neavitt Rd, Saint Michaels, MD 21663

    SELLER TO REVIEW ALL OFFERS ON JANUARY 25, 20205 AT 6 O'CLOCK Charming WaterfrontProperty with Established Vacation Rental BusinessDiscover an extraordinary opportunity with this 1.5+ acre waterfront property on Harris Creek. Featuring eight fully equipped, one-bedroom cottages and a spacious main house, this turn-key operation has been a successful vacation rental business for

    Mary Lapides Cummings & Co. Realtors

    8080 Bozman Neavitt Rd, Saint Michaels, MD 21663

Showing Results 121 - 160, Page 4 of 18

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