21

Sherwood, MD Homes for Sale with Acreage

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  • /72

    $759,000

    • 3 Beds
    • 2.5 Baths
    • 2,840 Sq Ft

    6660 Reeses Pride Rd, Sherwood, MD 21665

    Your Eastern Shore paradise awaits! This awesomely updated, meticulously maintained, classic colonial-style home is like a breath of fresh air. Located on a full 2 acre parcel, in the heart of the sought after Deep Harbour Farm community, custom features include a lovely private backyard oasis, designed around an 18’x32’ inground salt-water pool, and surrounded by all new, high-quality fencing,

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 431-3957

    6660 Reeses Pride Rd, Sherwood, MD 21665
  • /64

    $1,199,000

    • 3 Beds
    • 3 Baths
    • 3,853 Sq Ft

    6670 Tilghman Island Rd, Sherwood, MD 21665

    New Price! Waterfront home situated on Back Creek in Sherwood, offering direct access to the Chesapeake Bay and Choptank Rivers. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed

    Agent Photo

    Larry Brennan

    TTR Sotheby's International Realty

    (410) 881-8730

    6670 Tilghman Island Rd, Sherwood, MD 21665
  • /76

    $7,900,000

    • 8 Beds
    • 5.5 Baths
    • 9,051 Sq Ft

    8612 Tilghman Island Rd, Wittman, MD 21676

    "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 115-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated

    Laura Carney TTR Sotheby's International Realty

    8612 Tilghman Island Rd, Wittman, MD 21676
  • /44

    $1,499,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 3.5 Baths
    • 2,672 Sq Ft

    7650 Ferry Cove Rd, Sherwood, MD 21665

    Discover this stunning, custom-built waterfront Cape Cod nestled in Ferry Cove, Sherwood, a serene setting that is located right next door to a HGTV dream home! Newly constructed in 2024, this home offers the ultimate blend of luxury and comfort. Owners enjoy direct access to a beautiful sandy beach with 186 feet of waterfrontage on the Chesapeake Bay, creating the perfect space for both

    Krissy Curtis Coldwell Banker Realty

    7650 Ferry Cove Rd, Sherwood, MD 21665
  • /42

    $3,295,000

    • 5 Beds
    • 4.5 Baths
    • 4,843 Sq Ft

    5995 Elston Shore Rd, Neavitt, MD 21652

    "Fox Haven" Privately sited on almost 10 acres with 900+ feet of protected waterfront, this impressive retreat captures breathtaking wide water views from nearly every vantage point. Offering approximately 4,800 square feet of living space across three finished levels, the home is designed for comfort and versatility, with wood flooring, a well-appointed kitchen with island, and distinct living

    Wink Cowee Benson & Mangold, LLC

    5995 Elston Shore Rd, Neavitt, MD 21652
  • /40

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    6705 Tilghman Island Rd, Sherwood, MD 21665

    Nestled on over 2 acres in the desirable water access community of Deep Harbor Farm, this beautiful Cape Cod beams with natural light. The home features over 2,400 sqft with 4 bedrooms and 2.5 baths. The welcoming foyer overlooks a spacious dining room and leads to an open kitchen complete with white cabinetry, stainless steel appliances, breakfast bar and a large table space. Just off the

    Kim Crouch Ozman Benson & Mangold, LLC

    6705 Tilghman Island Rd, Sherwood, MD 21665
  • /48

    $595,000

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

    23201 Stewart Way, McDaniel, MD 21647

    Tucked away down a private lane, this stunning and fully renovated 3-bedroom, 2.5-bath Cape Cod sits on a serene 3.43± acre parcel, offering exceptional privacy and a truly remarkable setting. A covered front porch welcomes you home and provides the perfect place to relax while overlooking the tranquil setting that the property offers. Inside, luxury vinyl plank flooring flows throughout the

    Kim Crouch Ozman Benson & Mangold, LLC

    23201 Stewart Way, McDaniel, MD 21647
  • /57

    $590,000

    • 3 Beds
    • 1.5 Baths
    • 1,761 Sq Ft

    8000 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled along the peaceful waters of Swan Cove with access to Harris Creek, this circa 1890 farmhouse is full of Eastern Shore character and charm. Set on 1.38 private acres, the property offers the peace and serenity you’re seeking. The spacious enclosed front porch is accented with wood floors and a wood ceiling setting the tone of this charming home. The inviting foyer features original

    Kim Crouch Ozman Benson & Mangold, LLC

    8000 Bozman Neavitt Rd, Bozman, MD 21612
  • /39

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    21869 Albie Rd, Sherwood, MD 21665

    Barely lived in totally maintenance free rancher on a 3+/- acre lot with broad water views. Freshly painted with new landscaping it is vacant and available for immediate occupancy! Main area has beautiful wood laminate flooring with carpet in all bedrooms. Bonus room to be used as an office/family room, granite counters with wine refrigerator and all nearly new appliances with utility room and

    Bill Wieland Benson & Mangold, LLC

    21869 Albie Rd, Sherwood, MD 21665
  • /43

    $1,995,000 Open Sat 10AM - 12PM

    • 5 Beds
    • 3.5 Baths
    • 4,310 Sq Ft

    22707 Marshall Ln, Wittman, MD 21676

    Private Harris Creek waterfront with pool, pier boat lift and deep water access—ideal for boating kayaking and quiet days on the water. Five bedrooms and three-and-a-half baths designed for a relaxed yet refined Eastern Shore lifestyle. Featuring sun-filled interiors feature red oak floors custom built-ins multiple fireplaces and wide water views. The kitchen is designed for gathering with

    Kathy Christensen TTR Sotheby's International Realty

    22707 Marshall Ln, Wittman, MD 21676
  • /116

    $7,500,000

    • 6 Beds
    • 8 Baths
    • 8,476 Sq Ft

    7508 Cooper Point Rd, Bozman, MD 21612

    Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of

    Kim Crouch Ozman Benson & Mangold, LLC

    7508 Cooper Point Rd, Bozman, MD 21612
  • /71

    $3,100,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 4,035 Sq Ft

    23961 Lynnewood Dr, Saint Michaels, MD 21663

    Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining

    Barbara Watkins Benson & Mangold, LLC

    23961 Lynnewood Dr, Saint Michaels, MD 21663
  • /32

    $549,000

    • 9 Beds
    • 2.5 Baths
    • 5,389 Sq Ft

    21486 Mission Rd, Tilghman, MD 21671

    This historic property known as "The Elms" was built in 1900 and originally used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water and consists of three buildings which are: The original main building, the detached garage and a shed/storage building. The buildings hold virtually no value unless an extensive historic renovation were completed, but the

    Monica Penwell TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • /60

    $3,650,000 Open House 4/11

    • 5 Beds
    • 5.5 Baths
    • 6,487 Sq Ft

    8781 Tilghman Island Rd, Wittman, MD 21676

    A magnificent, stately, Daffin-built, Chesapeake Bay Brick Estate exudes excellent design and craftsmanship in this 5 bedroom (suites) , 5.5 bath 6,500 sq. ft brick home that majestically sits on 21.7 acres facing the Chesapeake Bay. Excellent construction quality and design are evident throughout this magnificent estate. Geothermal system on 1st and 2nd floors; Heat Pump for the 3rd floor;

    Robert Lacaze TTR Sotheby's International Realty

    8781 Tilghman Island Rd, Wittman, MD 21676
  • /46

    $3,700,000

    • 5 Beds
    • 7 Baths
    • 5,554 Sq Ft

    21721 Heavenly Haven Rd, Sherwood, MD 21665

    GENEROUS PRICE REDUCTION!!!! This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21721 Heavenly Haven Rd, Sherwood, MD 21665
  • /86

    $7,500,000

    • 5 Beds
    • 6 Baths
    • 10,000 Sq Ft

    7090 Cooper Point Rd, Bozman, MD 21612

    Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a

    Laura Carney TTR Sotheby's International Realty

    7090 Cooper Point Rd, Bozman, MD 21612
  • /88

    $1,895,000

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

    23857 Ebb Point Rd, Bozman, MD 21612

    *Furniture and decor included in sale*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

    Tiffany Cloud Meredith Fine Properties

    23857 Ebb Point Rd, Bozman, MD 21612
  • /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
  • /11

    $475,000 Coming Soon

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

    22539 Indian Point Rd, Bozman, MD 21612

    Great opportunity to own a lovely home in a great location! Additional pictures and details coming soon.

    James Schaecher Keller Williams Flagship

    22539 Indian Point Rd, Bozman, MD 21612
  • /22

    $2,300,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    Set on 19.5 private acres just minutes from historic waterfront Saint Michaels, this exceptional 4,492 sq ft residence offers the perfect blend of space, privacy, and convenience. The home features four bedrooms and two and a half baths, with expansive living areas ideal for both everyday living and entertaining, including a well-appointed chef's kitchen. The thoughtfully designed layout includes

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, Saint Michaels, MD 21663
  • /83

    $1,200,000

    • 5 Beds
    • 2.5 Baths
    • 4,214 Sq Ft

    5520 Leeward Ln, Tilghman, MD 21671

    Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a

    Samantha Jackson Keller Williams Realty

    5520 Leeward Ln, Tilghman, MD 21671
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