2,827

Saint Michaels, MD Homes

Section Image
  • /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
    • /65

      Est $1,588,391 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,579 Sq Ft

      417 Water St, Saint Michaels, MD 21663

      417 Water St, Saint Michaels, MD 21663
  • /56

    $1,899,000

    • 4 Beds
    • 3.5 Baths
    • 3,575 Sq Ft

    216 E Chew Ave, Saint Michaels, MD 21663

    Experience and enjoy captivating views of the St Michaels Harbor from every room in the house. Conveniently situated in the heart of downtown St Michaels within walking distance to casual and fine dining. The floorplan includes 4 bedrooms, 3 full baths and 1 half bath. Total bedroom and bath count includes a separate guest suite with full kitchen. The newer addition is an octagon great room with

    Daphne Cawley TTR Sotheby's International Realty

    216 E Chew Ave, 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
    • /60

      Est $1,643,711 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,644 Sq Ft

      10536 Miracle House Cir, Claiborne, MD 21624

      10536 Miracle House Cir, Claiborne, MD 21624
  • /17

    $889,800 New Construction

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

    Lot 2 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

    Lot 2 Meadow St, 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
    • /27

      Est $950,762 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,213 Sq Ft

      9792 Martingham Cir Unit B1, Saint Michaels, MD 21663

      9792 Martingham Cir Unit B1, Saint Michaels, MD 21663
  • /24

    $799,000 New Construction

    • 4 Beds
    • 2.5 Baths

    Lot 16A Meadow St, Saint Michaels, MD 21163

    Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe.Time to make your personal selections.Make this home your personal staement.Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more.Make this

    George Bailey Keller Williams Flagship

    Lot 16A Meadow St, Saint Michaels, MD 21163
  • /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
    • /57

      Est $813,461 Not Listed For Sale

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

      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663

      9792 Martingham Cir Unit B5, Saint Michaels, MD 21663
  • /70

    $795,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,038 Sq Ft

    7896 Hart Glen Ct, Saint Michaels, MD 21663

    Located at the end of a quiet cul-de-sac in the desirable Back Creek Landing neighborhood of St. Michaels, Maryland, this beautifully maintained home offers privacy, quality upgrades, and a fantastic Eastern Shore lifestyle. The large, inviting front porch sets the tone as you arrive. Step inside and you are welcomed by a warm, light-filled interior that immediately feels like home. The floor

    Kathleen Coale Benson & Mangold, LLC

    7896 Hart Glen Ct, 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
    • /48

      Est $867,973 Not Listed For Sale

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

      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663

      9794 Martingham Cir Unit D5, Saint Michaels, MD 21663
  • /40

    $795,000 Under Contract

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

    24989 Back Creek Dr, Saint Michaels, MD 21663

    Set in the welcoming Back Creek Landing neighborhood, this bright and beautifully updated home offers the best of Eastern Shore living—just moments from the shops, restaurants, and waterfront of downtown St. Michaels.A classic front porch invites you into a thoughtfully designed interior, where natural light and an easy floor plan make everyday living effortless. The open-concept kitchen and

    Kathleen Coale Benson & Mangold, LLC

    24989 Back Creek Dr, 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
    • /56

      Est $468,841 Not Listed For Sale

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

      24360 Widgeon Place Unit 7, Saint Michaels, MD 21663

      24360 Widgeon Place Unit 7, Saint Michaels, MD 21663
  • /46

    $875,000 Under Contract

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

    602 S Talbot St, Saint Michaels, MD 21663

    PRICE IMPROVEMENT..... MUST SEE THIS Charming 4-Bedroom Home with Guest Cottage in Saint Michaels, MDNestled in the picturesque town of Saint Michaels, this enchanting property offers a unique blend of classic charm and modern comfort. The main residence features four bedrooms, providing ample space for families or those seeking room to grow. With meticulous attention to detail, the interior

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    602 S Talbot St, 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
    • /31

      Est $934,899 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,213 Sq Ft

      9792 Martingham Cir, Saint Michaels, MD 21663

      9792 Martingham Cir, Saint Michaels, MD 21663
  • /80

    $3,475,000

    • 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 has been

    Kathleen Eder Compass

    9791 Pintail Place, 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
    • /51

      Est $861,642 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
  • /58

    $699,000

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

    204 W Chew Ave, Saint Michaels, MD 21663

    Big things come in small packages! A St. Michaels treasure! Absolutely charming, completely renovated historic property only steps to the waterfront park & a block into town. This beautiful home has been renovated from top to bottom & has been designed to offer style & historic charm. Featuring a new, lifetime blue metal roof, gardens, patios, & relaxing, covered front porch to watch the world

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

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

    $1,295,000 Sold Feb 21, 2025

    • 1,938 Sq Ft
    • $668/SF
    • 3 Beds
    • 2.5 Baths
    • Built 1786

    104 Mulberry St, Saint Michaels, MD 21663

    Located in the heart of St. Michaels' Historic District, the "Keithley House," circa 1786, is one of the town's historic treasures. Records indicate the house was renovated and expanded between 1860 and 1870, when Victorian elements were incorporated, including a wonderful front porch. The house was extensively restored and updated in 2008, with care to preserve the 18th and 19th century charm.

    Tom Crouch Benson & Mangold, LLC

    104 Mulberry St, Saint Michaels, MD 21663
    • /35

      Est $452,509 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
  • /43

    $720,000

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

    24749 Swan Rd, Saint Michaels, MD 21663

    Located in Martingham, home of the newly redesigned Pete Dye golf course, The Links at Perry Cabin. This 3BR/2.5BA Colonial style home is situated on an open 1.13ac lot with a tree lined backyard for privacy. Inside you will enjoy a spacious floor plan, and updated island kitchen, and a large family room highlighted by a wood burning fireplace and a beam ceiling. Upstairs you will find the

    Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, Saint Michaels, MD 21663
  • /6

    $685,000 Sold Feb 07, 2025

    • Land
    • 16 Acres
    • $42,653 per Acre
    • 16 Days On Market

    0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663

    Solitude Creek - 16 acres of beautiful pine forest offering seclusion and privacy within a short distance to St. Michaels. With 675 feet of shoreline on Solitude Creek with approximately four feet at mean low tide, this tidal waterway provides a sanctuary for wintering waterfowl. Previously perc approved for a 4 bedroom home.

    Coard Benson Benson & Mangold, LLC

    0 Pea Neck Rd Unit MDTA2008994, Saint Michaels, MD 21663
    • /35

      Est $426,753 Not Listed For Sale

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

      24360 Widgeon Place Unit 10, Saint Michaels, MD 21663

      24360 Widgeon Place Unit 10, 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

    • 1,800 Sq Ft
    • $219/SF
    • 119 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1973

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

    Nestled in the desirable Martingham community and backing to the scenic 2nd hole at the Links of Perry Cabin, this charming 2-bedroom, 2.5-bathroom condo offers a perfect retreat for low-maintenance living. The open living and dining area, featuring a cozy wood-burning fireplace, flows seamlessly into the inviting sunroom, creating the ideal space for relaxation. The primary bedroom boasts a

    Chuck Mangold Benson & Mangold, LLC

    9539 Quail Hollow Dr Unit 302, Saint Michaels, MD 21663
    • /34

      Est $432,032 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
  • /51

    $659,000 Open Sat 12PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft

    901 S Talbot St, Saint Michaels, MD 21663

    St. Michaels English style Cottage – This Adorable 3-bedroom 2 bath home offers a first-floor primary bedroom, updated kitchen and baths, formal dining room, rear sunroom, and a fenced side and rear patio thoughtfully landscaped. The yard is irrigated. Long sweeping gables and roof peaks, prominent front facing chimney and entrance vestibule standout as architectural features of this 1930’s

    Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, Saint Michaels, MD 21663
  • /50

    $2,600,000 Sold Jan 30, 2025

    • 4,320 Sq Ft
    • $602/SF
    • 3 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2006

    1003 Riverview Terrace, Saint Michaels, MD 21663

    Experience tranquil waterfront living in this stunning 4BR/4.5 BA home sited on .67 acres overlooking the Miles River. Built in 2006, this Craftsman-style home was thoughtfully designed by Lars Erickson and built by Don Foster to blend effortlessly with the beauty of the landscape. The exquisite architectural details are evident throughout and include vaulted ceilings, Australian Cypress

    Laura Carney TTR Sotheby's International Realty

    1003 Riverview Terrace, Saint Michaels, MD 21663
    • /26

      Est $452,277 Not Listed For Sale

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

      9551 Quail Hollow Dr Unit 102, Saint Michaels, MD 21663

      9551 Quail Hollow Dr Unit 102, Saint Michaels, MD 21663
  • /108

    $8,875,000

    • 7 Beds
    • 7.5 Baths
    • 10,240 Sq Ft

    10770 Rich Neck Rd, Claiborne, MD 21624

    Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

    Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
  • /51

    $1,196,000 Sold Jan 21, 2025

    • 2,703 Sq Ft
    • $442/SF
    • 8 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1890

    202 Mulberry St, Saint Michaels, MD 21663

    Discover this charming historic home in the heart of St. Michaels, built circa 1890, where classic craftsmanship and timeless elegance come together. Starting with the expansive wrap-around porch, you can see this home is a traditional gem. Highlights of the home include 9ft. ceilings, hardwood floors throughout and original architectural details that define the craftsmanship. and charm. The

    Monica Penwell TTR Sotheby's International Realty

    202 Mulberry St, Saint Michaels, MD 21663
    • /22

      Est $450,571 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
  • /18

    $350,000

    • Land
    • 0.55 Acre
    • $636,364 per Acre

    108 Miles, Saint Michaels, MD 21663

    Build your dream home on this one-of-a- kind, half+ acre (24,082 sf) wooded lot in the heart ofSaint Michaels. Offering a tranquil, park-like setting, this rare property provides both privacy andconvenience, a five-minute walk to the town’s charming restaurants, coffeeshops, events and shopping. Located just outside the historic district line, this unusuallylarge lot (3 times the average lot size

    Jana Meredith Meredith Fine Properties

    108 Miles, Saint Michaels, MD 21663
  • /37

    $250,000 Sold Jan 14, 2025

    • Land
    • 6 Acres
    • $44,326 per Acre
    • 480 Days On Market

    0 Oakwood Park Rd, Saint Michaels, MD 21663

    Indulge in the allure of Eastern Shore living with this exquisite premium building site, situated in the esteemed Estate area of Oakwood Park. Just a stone's throw from the historic charm of downtown St. Michaels, this parcel offers a serene escape surrounded by nature's beauty. Picture-perfect views of San Domingo Creek adorn this tranquil lot, dotted with mature trees. Anticipate the

    Connie Loveland Benson & Mangold, LLC

    0 Oakwood Park Rd, Saint Michaels, MD 21663

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home