25

Saint Michaels, MD Houses for Sale

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  • 9191 Deepwater Point Rd, Saint Michaels, MD 21663
    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    /103

    $3,300,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 4 Baths
    • 5,088 Sq Ft

    9191 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to 9191 Deepwater Point Road, a captivating waterfront estate set on over 12 acres nestled along the Miles River and Long-Haul Creek in St. Michaels, Maryland. Built in 1988, this 5,088 -square-foot home features 5 bedrooms and 4 full bathrooms, the convenient first-floor primary suite is spacious and includes a sauna, fireplace and sunroom with a vaulted ceiling, skylights and panoramic

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (866) 528-7062

    9191 Deepwater Point Rd, Saint Michaels, MD 21663
  • 1026 Riverview Terrace, Saint Michaels, MD 21663
    1026 Riverview Terrace, Saint Michaels, MD 21663
    1026 Riverview Terrace, Saint Michaels, MD 21663
    /70

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 2,535 Sq Ft

    1026 Riverview Terrace, Saint Michaels, MD 21663

    Experience luxury living in this newly renovated coastal-style home in St. Michaels. Situated on a double lot, this is an exceptional and rare offering, combining water views and water access with a high quality home, redone with incredible attention to detail and livability. The exterior is tastefully appointed with painted brick and shingle-style siding, and an inviting covered front porch

    Carolina Barksdale Benson & Mangold, LLC

    1026 Riverview Terrace, Saint Michaels, MD 21663
  • 9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    /41

    $1,795,000 Open Sun 1PM - 3PM

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

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Deepwater Retreat, an extraordinary 6+/- acre waterfront property overlooking the Links at Perry Cabin Golf Course with direct access to the Long Haul Creek and Miles River. Just moments to downtown Saint Michaels, fine dining, shopping, and entertainment, this stunning makeover offers 4,100 +/- sq. ft. of single-story living designed for endless indoor/outdoor entertainment. This

    Craig Linthicum Benson & Mangold, LLC

    9171 Deepwater Point Rd, Saint Michaels, MD 21663
  • 504 S Talbot St, Saint Michaels, MD 21663
    504 S Talbot St, Saint Michaels, MD 21663
    504 S Talbot St, Saint Michaels, MD 21663
    /51

    $895,000

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    504 S Talbot St, Saint Michaels, MD 21663

    Nestled in the heart of Historic St. Michaels, this beautifully renovated 1900’s home features, multiple fireplaces, hardwood floors and beams with natural light. This 3-bedroom, 2.5-bathroom residence is a perfect Eastern Shore retreat. A charming covered front porch welcomes you into the cozy living room highlighted by a wood-burning fireplace. The spacious, open-concept kitchen boasts granite

    Kim Crouch Ozman Benson & Mangold, LLC

    504 S Talbot St, Saint Michaels, MD 21663
  • 103 Mulberry St, Saint Michaels, MD 21663
    103 Mulberry St, Saint Michaels, MD 21663
    103 Mulberry St, Saint Michaels, MD 21663
    /69

    $875,000

    • 4 Beds
    • 1.5 Baths
    • 1,596 Sq Ft

    103 Mulberry St, Saint Michaels, MD 21663

    Known as, "The Mary Thomas House," circa 1860, this beautifully maintained and tastefully updated home is absolutely charming, inside and out...A very comfortable home! Centrally located in St. Michaels' Historic District, mid-way between the Harbor, two waterfront parks and Talbot Street (the town's main street), with it's many fine shops and restaurants. All the main attractions, including

    Tom Crouch Benson & Mangold, LLC

    103 Mulberry St, Saint Michaels, MD 21663
  • 7369 Drum Point Rd, Saint Michaels, MD 21663
    7369 Drum Point Rd, Saint Michaels, MD 21663
    7369 Drum Point Rd, Saint Michaels, MD 21663
    /41

    $1,995,000

    • 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
  • 216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, 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
  • Lot 2 Meadow St, Saint Michaels, MD 21663
    Lot 2 Meadow St, Saint Michaels, MD 21663
    Lot 2 Meadow St, Saint Michaels, MD 21663
    /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
  • Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    /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
  • 103 W Marengo St, Saint Michaels, MD 21663
    103 W Marengo St, Saint Michaels, MD 21663
    103 W Marengo St, Saint Michaels, MD 21663
    /10

    $600,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 1.5 Baths
    • 1,209 Sq Ft

    103 W Marengo St, Saint Michaels, MD 21663

    Quintessential St. Michaels Charm! Nestled in the heart of this historic and picturesque waterfront town, this adorable cedar shake home is straight out of Nantucket! With two bedrooms, one and a half baths, and classic coastal curb appeal, this home sits on a generous fenced lot backing up to alley way—perfect for outdoor entertaining, gardening, or simply soaking in the Chesapeake breeze.

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    103 W Marengo St, Saint Michaels, MD 21663
  • 400 Railroad Ave, Saint Michaels, MD 21663
    400 Railroad Ave, Saint Michaels, MD 21663
    400 Railroad Ave, Saint Michaels, MD 21663
    /35

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    400 Railroad Ave, Saint Michaels, MD 21663

    Nestled on a desirable corner lot in the historic waterfront town of St. Michaels, this 1930 bungalow blends classic architecture with modern comforts. Ideally located just a short distance from the Chesapeake Bay Maritime Museum, shops, restaurants, and the harbor, this home offers the best of in-town living. A spacious front porch welcomes you - perfect for morning coffee or casual

    Monica Penwell TTR Sotheby's International Realty

    400 Railroad Ave, Saint Michaels, MD 21663
  • 901 S Talbot St, Saint Michaels, MD 21663
    901 S Talbot St, Saint Michaels, MD 21663
    901 S Talbot St, Saint Michaels, MD 21663
    /51

    $659,000 Open Sun 12PM - 2PM

    • 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
  • 10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    /91

    $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
  • 204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    /40

    $675,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Coastal charm meets small-town living in this beautifully updated cottage, just one block from the Historic District and 1.5 blocks from water access, including a marina and boat ramp, and downtown Saint Michaels!?This home exudes a true vacation vibe, offering main-level living with sun-filled spaces designed for relaxation. The completely remodeled full bathroom adds modern comfort, while the

    Jennifer Chino Compass

    204 E Marengo St, Saint Michaels, MD 21663
  • 112 Mitchell St, Saint Michaels, MD 21663
    112 Mitchell St, Saint Michaels, MD 21663
    112 Mitchell St, Saint Michaels, MD 21663
    /19

    $303,500

    • 3 Beds
    • 1 Bath
    • 1,368 Sq Ft

    112 Mitchell St, Saint Michaels, MD 21663

    Located in Saint Michaels Maryland. Within close proximity to everything fun this local town has to offer. Great seafood, boating, at a price that allows you to make it your own. Currently 3 bedrooms and 1 bath. With a very easy remodel, you could make it a 4 bedroom 2 bath. Large rear yard and paved driveway. Full time, weekend home, or rental. OWNER IS READY TO SELL… Let’s see your offer…

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    112 Mitchell St, Saint Michaels, MD 21663
  • 106C Conner St, Saint Michaels, MD 21663
    106C Conner St, Saint Michaels, MD 21663
    106C Conner St, Saint Michaels, MD 21663
    /33

    $399,000

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

    106C Conner St, Saint Michaels, MD 21663

    Charming updated cottage in the center of St. Michaels. Move in ready. Modern kitchen with 5-burner gas stove, white cabinetry and stainless steel appliances. Bright and open living space plus a dining area off the kitchen and an updated bathroom with walk in, custom glass enclosed large shower. The house offers bedrooms and a den. Lots of windows on all sides let in light everywhere. The front

    Carolina Barksdale Benson & Mangold, LLC

    106C Conner St, Saint Michaels, MD 21663
  • 1221 Washington Dr, Saint Michaels, MD 21663
    1221 Washington Dr, Saint Michaels, MD 21663
    1221 Washington Dr, Saint Michaels, MD 21663
    /89

    $525,000

    • 4 Beds
    • 3 Baths
    • 1,848 Sq Ft

    1221 Washington Dr, Saint Michaels, MD 21663

    ASSUMABLE USDA LOAN AT 3.25%! Charm meets modern luxury in this beautifully appointed Cape Cod nestled in the desirable Rio Vista community of historic Saint Michaels. This thoughtfully designed 4 bedroom, 3 full bath two-story home is situated on a .34 acre setting and seamlessly blends traditional architecture with contemporary amenities, creating an inviting space perfect for both everyday

    Barbara McCaffrey Redfin Corp

    1221 Washington Dr, Saint Michaels, MD 21663
  • 25070 Hurley Ln, Saint Michaels, MD 21663
    25070 Hurley Ln, Saint Michaels, MD 21663
    25070 Hurley Ln, Saint Michaels, MD 21663
    /28

    $499,000

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

    25070 Hurley Ln, Saint Michaels, MD 21663

    Welcome to 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 residence boasts an inviting open floor plan, the perfect ambiance for relaxation. The modern kitchen has been expertly remodeled with upgrades and

    Stephany Barrett Long & Foster Real Estate, Inc.

    25070 Hurley Ln, Saint Michaels, MD 21663
  • 10376 Claiborne Rd, Claiborne, MD 21624
    10376 Claiborne Rd, Claiborne, MD 21624
    10376 Claiborne Rd, Claiborne, MD 21624
    /57

    $269,900 Open Sun 1PM - 3PM

    • 3 Beds
    • 1 Bath
    • 1,282 Sq Ft

    10376 Claiborne Rd, Claiborne, MD 21624

    Looking for a sweet little cottage in a waterfront town minutes from Saint Michaels? The cottage has a brand-new septic system, just installed new toilet, vanity, stove, and refrigerator, hardwood floors, fireplace, large porch off the back, and short walk to Eastern Bay or Tilghman Creek. This home is ready to be loved by its next owner. This property is being sold "as is." Call today for

    Jana Meredith Meredith Fine Properties

    10376 Claiborne Rd, Claiborne, MD 21624
  • 100 Lee St, Saint Michaels, MD 21663
    100 Lee St, Saint Michaels, MD 21663
    100 Lee St, Saint Michaels, MD 21663
    /18

    $399,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    100 Lee St, Saint Michaels, MD 21663

    This low-maintenance two-bedroom cottage, located across from the Inn at Perry Cabin at the corner of Talbot and Lee Streets, has been fully renovated with luxury vinyl plank flooring, board & batten siding, updated fixtures, recessed lighting, crown molding, tile shower surround, and a front-loading washer/dryer. It's ideal for a weekend retreat or as an investment property. The landscaping has

    Stacie Luhrman Benson & Mangold, LLC

    100 Lee St, Saint Michaels, MD 21663
  • 9791 Pintail Place, Saint Michaels, MD 21663
    9791 Pintail Place, Saint Michaels, MD 21663
    9791 Pintail Place, Saint Michaels, MD 21663
    /122

    $3,495,000

    • 5 Beds
    • 6 Baths
    • 7,300 Sq Ft

    9791 Pintail Place, Saint Michaels, MD 21663

    Inspired by the architecture of the French West Indies, this unique 7,300 +/- square foot waterfront retreat features five octagonal wings linked together, offering stunning panoramic views of the Miles River from nearly every room. Step into the luxurious interiors of Rivermark and you'll find yourself immersed in a world of exquisite craftsmanship and timeless elegance. Every detail has been

    Alicia Gannon Dulin Benson & Mangold, LLC

    9791 Pintail Place, Saint Michaels, MD 21663
  • 204 W Chew Ave, Saint Michaels, MD 21663
    204 W Chew Ave, Saint Michaels, MD 21663
    204 W Chew Ave, Saint Michaels, MD 21663
    /61

    $725,000

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

    204 W Chew Ave, Saint Michaels, MD 21663

    Price improvement, bring offers! Small house with big heart! 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 & coastal feel all while retaining it’s historic charm. Featuring a new, lifetime blue metal roof,

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    204 W Chew Ave, Saint Michaels, MD 21663
  • 24629 Beverly Rd, Saint Michaels, MD 21663
    24629 Beverly Rd, Saint Michaels, MD 21663
    24629 Beverly Rd, Saint Michaels, MD 21663
    /93

    $9,950,000

    • 5 Beds
    • 7 Baths
    • 10,309 Sq Ft

    24629 Beverly Rd, Saint Michaels, MD 21663

    Travel down a mature, holly tree-lined drive and One Beverly reveals itself with understated Eastern Shore elegance. Situated on the 9 acre original farmstead of the 1867 Beverly Manor, this Georgian home provides a southwestern view overlooking San Domingo and Broad Creeks. The 5-bedroom main house, first occupied in 2003, is a traditional Georgian design meticulously built according to

    Clifford Meredith Meredith Fine Properties

    24629 Beverly Rd, Saint Michaels, MD 21663
  • 8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /60

    $9,950,000

    • 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
  • 110 Lee St, Saint Michaels, MD 21663
    110 Lee St, Saint Michaels, MD 21663
    110 Lee St, Saint Michaels, MD 21663
    /37

    $499,900 New Construction

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

    110 Lee St, Saint Michaels, MD 21663

    A NEW BUILD FOR UNDER $500,000. Welcome to your dream home in an adorable small town! This NEW rancher comes with elegance and comfort. Featuring a well-designed Open floor plan, this home offers spacious living areas ideal for both relaxation and entertaining.As you step inside, you'll be greeted by the warm ambiance of the inviting living room, perfect for cozy gatherings with loved ones. The

    Chance Stem LPT Realty, LLC

    110 Lee St, Saint Michaels, MD 21663
Maryland Saint Michaels

Houses for Sale in Saint Michaels, MD

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In Saint Michaels, there are currently 25 houses for sale, offering an array of options for potential buyers. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Saint Michaels, MD and find the perfect place to call home.

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