28

Homes for Sale in 21663

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  • 205 E Chew Ave, Saint Michaels, MD 21663
    205 E Chew Ave, Saint Michaels, MD 21663
    205 E Chew Ave, Saint Michaels, MD 21663
    /28

    $1,275,000

    • 2 Beds
    • 1.5 Baths
    • 1,780 Sq Ft

    205 E Chew Ave, Saint Michaels, MD 21663

    The Arthur K. Easter House, St. Michaels, MarylandFrom the moment you arrive, it is clear: this is no ordinary house. Located on one of St. Michaels’ most sought-after streets, the circa 1889 Arthur K. Easter House seems to have stepped from the pages of a storybook—one filled with golden light, quiet elegance, and a sense of belonging. This stylish historic home was relocated to its current

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (866) 771-9340

    205 E Chew Ave, Saint Michaels, MD 21663
  • 222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    /38

    $2,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    222 E Chestnut St, Saint Michaels, MD 21663

    A unique opportunity to own a completely renovated home in the heart of town featuring four deep-water, dedicated boat slips. Located at the end of one of the most coveted, tree-lined streets in St. Michaels, this home is surrounded by beautifully restored historic properties and offers incredible views of St. Michaels Harbor. The current owners have thoughtfully renovated this 3-bedroom,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (844) 651-2546

    222 E Chestnut St, Saint Michaels, MD 21663
  • 100 Mulberry St, St. Michaels, MD 21663
    100 Mulberry St, St. Michaels, MD 21663
    100 Mulberry St, St. Michaels, MD 21663
    /6

    $950,000

    • Studio
    • 4,172 Sq Ft

    100 Mulberry St, St. Michaels, MD 21663

    Exceptional location with ample off-street parking—this spacious and well-maintained triplex is an ideal investment in the highly desirable St. Michaels community. The first floor features a spacious 3-bedroom, 3.5-bath unit with a large kitchen, a formal dining room with a cozy wood-burning fireplace, a generous living room, and a private laundry room.Upstairs, the second floor features two

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    (877) 846-5106

    100 Mulberry St, St. 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

    $1,695,000 Open Sun 11AM - 1PM

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

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Micheals Retreat, an extraordinary 6+/- acre property overlooking the Links at Perry Cabin Golf Course with direct water access to 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
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /99

    $1,249,000

    • 3 Beds
    • 3 Baths
    • 1,612 Sq Ft

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    St Michaels is just 2 miles away... Oakwood park known to be a slice of Eastern Shore heaven. This one story cottage with a dreamy porch and carriage house serves as the owners get away and vacation rental. Features are riprap shoreline and a boat ramp, the Carriage house with second floor guest and a balcony overlooking San Domingo Creek, a 2 car garage with workshop, laundry space and

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24318 Oakwood Park 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
  • 304 N Talbot St, Saint Michaels, MD 21663
    304 N Talbot St, Saint Michaels, MD 21663
    304 N Talbot St, Saint Michaels, MD 21663
    /42

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 2,028 Sq Ft

    304 N Talbot St, Saint Michaels, MD 21663

    The best of St. Michaels living.Step into the heart of St. Michaels and experience the ease of in-town living. Across from the iconic Inn at Perry Cabin and just a short stroll to the Maritime Museum, boutique shops, and waterfront dining, this home offers a rare blend of modern comfort and small-town charm. Built in 2021, the two-story residence was thoughtfully designed for both relaxation

    Wink Cowee Benson & Mangold, LLC

    304 N Talbot St, Saint Michaels, MD 21663
  • 24312 Oakwood Park Rd, Saint Michaels, MD 21663
    24312 Oakwood Park Rd, Saint Michaels, MD 21663
    24312 Oakwood Park Rd, Saint Michaels, MD 21663
    /54

    $825,000

    • 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
  • 113 Thompson St, Saint Michaels, MD 21663
    113 Thompson St, Saint Michaels, MD 21663
    113 Thompson St, Saint Michaels, MD 21663
    /61

    $600,000

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft

    113 Thompson St, Saint Michaels, MD 21663

    Nestled in the heart of the St. Michaels Historic District, this charming 3-bedroom, 2-bath home is a designated historic landmark that beautifully blends classic character with modern convenience. Step inside to find refinished original wood floors (2021), stunning historic details like a pocket door between the hallway and living room, coffered ceiling and back staircase up to the

    Kim Lally EXP Realty, LLC

    113 Thompson St, Saint Michaels, MD 21663
  • 300 Perry St, Saint Michaels, MD 21663
    300 Perry St, Saint Michaels, MD 21663
    300 Perry St, Saint Michaels, MD 21663
    /10

    $160,000

    • Land
    • 0.14 Acre
    • $1,142,857 per Acre

    300 Perry St, Saint Michaels, MD 21663

    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
  • 510 Tenant Cir, Saint Michaels, MD 21663
    510 Tenant Cir, Saint Michaels, MD 21663
    510 Tenant Cir, Saint Michaels, MD 21663
    /56

    $675,000

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

    510 Tenant Cir, Saint Michaels, MD 21663

    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 gotten some great updates over the years,

    Larry Brennan TTR Sotheby's International Realty

    510 Tenant Cir, Saint Michaels, MD 21663
  • 23857 Ebb Point Rd, Bozman, MD 21612
    23857 Ebb Point Rd, Bozman, MD 21612
    23857 Ebb Point Rd, Bozman, MD 21612
    /94

    $2,100,000

    • 4 Beds
    • 3.5 Baths
    • 2,250 Sq Ft

    23857 Ebb Point Rd, Bozman, MD 21612

    Experience elevated coastal living in this impeccably renovated 2,250 sq ft post-and-beam home, reimagined as a coastal modern contemporary masterpiece by interior designer Hollace Kutay. Known as Oyster Cove for its picturesque 2.5 acre location on Broad Creek, this home is perfectly situated for boaters and kayakers seeking both adventure and tranquility. Enjoy expansive water views from nearly

    Hollace Kutay Meredith Fine Properties

    23857 Ebb Point Rd, Bozman, MD 21612
  • 9560 Martingham Cir, Saint Michaels, MD 21663
    9560 Martingham Cir, Saint Michaels, MD 21663
    9560 Martingham Cir, Saint Michaels, MD 21663
    /39

    $659,000

    • 3 Beds
    • 2.5 Baths
    • 2,350 Sq Ft

    9560 Martingham Cir, Saint Michaels, MD 21663

    Located in the popular Martingham community just beyond historic St. Michaels, this well-built one-level home has a prime location, with The Links at Perry Cabin golf course right behind it. The open, spacious floor plan features a large primary suite at one end and two bedrooms and bath at the other for maximum privacy. The owners added a sunroom with a grilling deck off the side. The kitchen

    Debra Crouch Benson & Mangold, LLC

    9560 Martingham Cir, Saint Michaels, MD 21663
  • 900 Riverview Terrace, Saint Michaels, MD 21663
    900 Riverview Terrace, Saint Michaels, MD 21663
    900 Riverview Terrace, Saint Michaels, MD 21663
    /38

    $2,845,000

    • 3 Beds
    • 2.5 Baths
    • 3,393 Sq Ft

    900 Riverview Terrace, Saint Michaels, MD 21663

    Welcome to this stunning brick one -story house on Riverview Terrace that you've always admired. From the moment that the front door opens, you will be captivated by the breathtaking views of the Miles River. This home offers an open floor-plan with a large great-room, dining room; kitchen, a primary bedroom suite , 2 guest rooms sharing a full bathroom,, an office and a powder room. Lovely

    Robert Lacaze TTR Sotheby's International Realty

    900 Riverview Terrace, Saint Michaels, MD 21663
  • 24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    /53

    $368,500

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

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    Martingham, a golf course and waterfront community just a mile outside of Historic St. Michaels with all of its amenities. This Widgeon Place condo is a two-story condo with two en-suite bedrooms and a half bath on the first floor. Living room and dining room are an open floor plan with hardwood floors and fireplace. From the sunroom you can step onto a brick patio which looks out to treed

    Jane Baker Benson & Mangold, LLC

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
  • 24977 Back Creek Dr, Saint Michaels, MD 21663
    24977 Back Creek Dr, Saint Michaels, MD 21663
    24977 Back Creek Dr, Saint Michaels, MD 21663
    /70

    $779,500

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

    24977 Back Creek Dr, Saint Michaels, MD 21663

    Discover this exquisite custom-built retreat in the serene St. Michaels community, a perfect blend of luxury and comfort with 4 spacious bedrooms and 3.5 well-appointed bathrooms, packed with premium features for an elevated lifestyle. Cozy up to the versatile gas fireplace, while enjoying a spacious layout enhanced with numerous built-ins for style and function. The expansive primary suite

    Eddie Mangold Benson & Mangold, LLC

    24977 Back Creek Dr, Saint Michaels, MD 21663
  • 24749 Swan Rd, Saint Michaels, MD 21663
    24749 Swan Rd, Saint Michaels, MD 21663
    24749 Swan Rd, Saint Michaels, MD 21663
    /43

    $650,000

    • 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
  • 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

    $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
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /18

    $350,000

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

    108 Miles, Saint Michaels, MD 21663

    Price Improved! 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

    Jana Meredith Meredith Fine Properties

    108 Miles, Saint Michaels, MD 21663
  • 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

    $629,000

    • 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
  • 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
  • 24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    /57

    $349,000

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft

    24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663

    Two bedroom, two bath home overlooking the Links at Perry Cabin. The spacious unit offers a living room with brick hearth fireplace, kitchen with table space and separate dining area. Relax on the rear patio overlooking a scenic community area and golf course. Minutes from downtown St. Michaels with boutique shops and restaurants.

    Jane Baker Benson & Mangold, LLC

    24560 Deepwater Point Dr Unit 1, 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

    $459,900

    • 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
  • 602 S Talbot St, Saint Michaels, MD 21663
    602 S Talbot St, Saint Michaels, MD 21663
    602 S Talbot St, Saint Michaels, MD 21663
    /46

    $850,000

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

    602 S Talbot St, Saint Michaels, MD 21663

    BACK ON THE MARKET-PRICE IMPROVEMENT..... MUST SEE THIS Charming 4-Bedroom Home with Guest Cottage in Saint Michaels, MDHome was under contract with a lovely couple trying to move their family to St. Michaels. WE GET IT- It's a Great place to live. Unfortunately, after waiting, and waiting and giving multiple extensions because the seller understood they really loved this home-- They just

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    602 S Talbot St, 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
    /16

    $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
  • 109 Bush Terrace, Saint Michaels, MD 21663
    109 Bush Terrace, Saint Michaels, MD 21663
    109 Bush Terrace, Saint Michaels, MD 21663
    /56

    $519,000 Coming Soon

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

    109 Bush Terrace, Saint Michaels, MD 21663

    St Michaels immaculate three bedroom just recently renovated. All new floors, bathrooms, new kitchen, redesigned first floor plan. Fabulous primary suite on first floor with gorgeous bathroom and large walk in closet . Welcoming laundry room and half a bath with accent wall. The large shady screened porch will be your second living and dining room in summer. There is a patio with privacy

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    109 Bush Terrace, Saint Michaels, MD 21663
  • 231 Madison Ave, Saint Michaels, MD 21663
    231 Madison Ave, Saint Michaels, MD 21663
    231 Madison Ave, Saint Michaels, MD 21663
    /30

    $649,000 Coming Soon

    • 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
Maryland Talbot County Saint Michaels 21663

Real Estate & Homes for Sale in 21663

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