33

Sherwood, MD Houses for Sale

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  • /56

    $610,000

    • 2 Beds
    • 2.5 Baths
    • 1,232 Sq Ft

    5379 Anchor Rd, Tilghman, MD 21671

    Bay Breezes & Beautiful Views: Your Tilghman Island HavenWaterview Living with Room to Breathe on Maryland's Eastern ShoreStep into the good life at 5379 Anchor Road, where Chesapeake Bay magic meets everydaycomfort. This charming home in Tilghman's friendly beach neighborhood sits just ashort stroll from the community beach where neighbors gather and memories are made.Picture yourself unwinding

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 206-6165

    5379 Anchor Rd, Tilghman, MD 21671
  • /50

    $1,795,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 2,775 Sq Ft

    7285 Quaker Neck Rd, Bozman, MD 21612

    Welcome to this serene 3BR/2BA/2625 sq ft waterfront home perfectly sited on 4.52 private acres in Bozman, MD. With panoramic views of Broad Creek from nearly every room, this custom-built residence is the perfect blend of rustic charm and modern comfort. The home's chalet-like architecture features vaulted and two-story ceilings, three cozy fireplaces, a generous array of windows and skylights,

    Laura Carney TTR Sotheby's International Realty

    7285 Quaker Neck Rd, Bozman, MD 21612
  • /74

    $1,300,000

    • 4 Beds
    • 3 Baths
    • 3,315 Sq Ft

    9190 Pennywhistle Dr, McDaniel, MD 21647

    PARADISE FOUND! 3.5 Acres surrounded on 3 sides by water at the end of a private Cul-de-sac teeming with wildlife and immersed in the scenic beauty of mature trees and wetland grasses.  Enjoy morning coffee and watch the eagles, osprey and turtles nest in your backyard from your kitchen table!  The two-slip pier offers opportunities to fish and crab and serves as a gateway to time on the water

    George Howard George Howard Real Estate Inc.

    9190 Pennywhistle Dr, McDaniel, MD 21647
  • /57

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 2,642 Sq Ft

    22860 Middle Point Rd, Neavitt, MD 21652

    Welcome to this architecturally designed waterfront retreat, thoughtfully created to capture broad, breathtaking views and harmonize with its natural surroundings. Set in a quiet village near historic St. Michaels, this home offers a rare blend of tranquility, comfort, and convenience—just minutes from a public park and landing. Inside, the home features 3 spacious bedrooms, an office, and

    Wink Cowee Benson & Mangold, LLC

    22860 Middle Point Rd, Neavitt, MD 21652
  • /29

    $1,395,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 1.5 Baths
    • 1,272 Sq Ft

    23468 Berry Rd, Bozman, MD 21612

    Picturesque Waterfront Cottage minutes from St. Michaels! This craftsman is the perfect “Get-Away” nestled on Grace Creek with plenty of privacy and surrounded by nature. Home has been beautifully maintained and updated featuring all of the amenties you would expect including knotty pine flooring throughout, kitchen with center island, granite tops, huge 6-burner Viking Stove and oven, Subzero

    Brian Gearhart Benson & Mangold, LLC

    23468 Berry Rd, Bozman, MD 21612
  • /65

    $950,000

    • 4 Beds
    • 2 Baths
    • 1,724 Sq Ft

    22769 Almost Neavitt Rd, Bozman, MD 21612

    PUBLIC SEWER COMING THIS YEAR! Immerse yourself in luxurious Eastern Shore living at this breathtaking waterfront retreat! Expertly designed by renowned local architect Pam Gardener, this four-bedroom, two-bath sanctuary rests at the end of a private road on a .92-acre lot, perfectly balancing tranquil seclusion with panoramic beauty. Showcasing 78 feet of riprap-protected shoreline along

    Barbara McCaffrey Redfin Corp

    22769 Almost Neavitt Rd, Bozman, MD 21612
  • /83

    $629,000

    • 3 Beds
    • 2 Baths
    • 2,091 Sq Ft

    8000 Bozman Neavitt Rd, Bozman, MD 21612

    WELCOME TO BLUE MOON! Your Hideaway Vacation Retreat! Minutes From Historic Waterfront Town of St. Michaels! Tucked Away in The Unique Village of Bozman! Privacy and Seclusion! Fronts Picturesque Cove of Harris Creek! Leisure Crabbing, Fishing, Kayaking and Shallow-Draft Boating Experience! 12 Foot Boat without Motor and 4 Kayaks Included! TO GET A BETTER IDEA OF HIGH TIDE CONDITIIONS BE SURE TO

    Stanley Dill Maranatha Realty

    8000 Bozman Neavitt Rd, Bozman, MD 21612
  • /27

    $749,000

    • 4 Beds
    • 3 Baths
    • 4,164 Sq Ft

    6253 Middle Point Rd, Neavitt, MD 21652

    A myriad of possibilties come with this unique property. Two homes for the price of one. The main house has 3 BR’s and 2 full baths, and the attached smaller home has two BR’s and one full bath. Both have fireplaces and light filled rooms. Located on about 2.1 +/_ acres in a quiet country setting and just minutes to a Talbot County boat ramp.

    Jane Baker Benson & Mangold, LLC

    6253 Middle Point Rd, Neavitt, MD 21652
  • /35

    $699,000

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

    21486 Mission Rd, Tilghman, MD 21671

    History:"The Elms" is located on the Northeast corner of Mission Road and Route 33 in the village of Tilghman on Tilghman Island, Talbot County, MD. The house faces west, with the gable oriented on a north/south axis. Built around 1893. The Elms is clad in weatherboard and supported by a brick pier foundation. The roof of this two story frame home is covered in asphalt shingles. The five bay

    Daphne Cawley TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • /83

    $2,200,000 Open Sat 11:30AM - 1:30PM

    • 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
  • /42

    $369,900

    • 2 Beds
    • 1.5 Baths
    • 892 Sq Ft

    5934 Tilghman Island Rd, Tilghman, MD 21671

    Successful vacation rental in the past. **Current license through Talbot Co, but it does not transfer. ** Completely remodeled, this 2 BR 1.5 bath open concept home is waiting for you to live your dream of home ownership or investing. Front screened porch is perfect for relaxing while looking at the water views of Harris Creek, many types of boats, and the marina across the street. Back deck is

    Iva Herr Benson & Mangold, LLC

    5934 Tilghman Island Rd, Tilghman, MD 21671
  • /31

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    6403 Bozman Neavitt Rd, Neavitt, MD 21652

    Located in the historic village of Neavitt, this charming house was built in 1890. It was thoroughly renovated in 2011 and the layout adapted for modern living, with light-filled rooms and a cleverly updated floor plan. The first-floor public spaces include a sitting room/office/entry, a generous living/dining room combination, and a handsome kitchen with water views, terrific storage, and room

    Joan Wetmore TTR Sotheby's International Realty

    6403 Bozman Neavitt Rd, Neavitt, MD 21652
  • /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
  • /50

    $2,795,000

    • 7 Beds
    • 7 Baths
    • 6,377 Sq Ft

    6020 Sunset Ln, Tilghman, MD 21671

    Welcome to Tilghman Landing on the Chesapeake Bay! This unique waterfront property offers an incredible opportunity, featuring three separate homes, two of which include garages, as well as a charming crab shack and private dock, all situated on .625 acres of Chesapeake Bay shoreline.Home #1: 6020 Sunset LaneThis spacious residence offers breathtaking, unobstructed views of the Bay. It includes 3

    Melissa Tippett TTR Sotheby's International Realty

    6020 Sunset Ln, Tilghman, MD 21671
  • /31

    $350,000

    • 1 Bed
    • 2 Baths
    • 1,100 Sq Ft

    6375 Bozman Neavitt Rd, Neavitt, MD 21652

    Enjoy peaceful water views and classic Eastern Shore charm in this well-maintained home in the village of Neavitt, just minutes from St. Michaels. Step into the open-concept great room, where hardwood floors, soaring ceilings, and a pellet stove create a warm and inviting living space. Floor-to-ceiling windows capture stunning views of Duck Cove and lead directly to a large deck—ideal for

    Wink Cowee Benson & Mangold, LLC

    6375 Bozman Neavitt Rd, Neavitt, MD 21652
  • /85

    $3,250,000

    • 6 Beds
    • 4.5 Baths
    • 4,352 Sq Ft

    7421 Quaker Neck Rd, Bozman, MD 21612

    For the first time in over half a century, an extraordinary opportunity presents itself—a chance to claim a piece of history that has remained in the loving stewardship of one family for generations. Nestled on over 13 private acres, this breathtaking 6-bedroom, 4.5-bath waterfront estate offers an unparalleled living experience with 4,352 square feet of main living space plus an additional 1,500

    Barbara McCaffrey Redfin Corp

    7421 Quaker Neck Rd, Bozman, MD 21612
  • /43

    $359,000

    • 2 Beds
    • 2 Baths
    • 1,222 Sq Ft

    8858 Howeth Rd, Wittman, MD 21676

    Welcome to this delightful cottage nestled in the historic village of Wittman. This home offers a whimsical, unique, and creative lifestyle in an historic waterman's cottage. Situated on a charming corner lot, this home has been thoughtfully updated while preserving its historic character. The second level boasts a private en-suite primary bedroom, complete with a cozy nook ideal for a home

    Monica Penwell TTR Sotheby's International Realty

    8858 Howeth Rd, Wittman, MD 21676
  • /62

    $600,000

    • 5 Beds
    • 3.5 Baths
    • 3,404 Sq Ft

    5559 Trafalgar Cir, Tilghman, MD 21671

    Welcome to this beautiful, spacious 5-bedroom, 3 1/2-bathroom single-family home located in the sought-after Tilghman on Chesapeake community. This property offers the perfect blend of modern comfort and serene island living, featuring an open-concept floor plan with plenty of natural light and elegant finishes. Each bedroom offers ample space and comfort with the Primary Suite offering 2

    Becky Wibberley Coldwell Banker Realty

    5559 Trafalgar Cir, Tilghman, MD 21671
  • /67

    $1,998,000

    • 4 Beds
    • 3 Baths
    • 2,628 Sq Ft

    7705 Quaker Neck Rd, Bozman, MD 21612

    This architecturally charming waterfront home sits on 5.6-acres of well-elevated land that offers an exceptional secluded setting and panoramic, wide views of Broad Creek. Located just minutes from Historic St. Michaels, this lovely home was thoughtfully expanded by the Easton architectural firm, Atelier 11 in a way that honors its distinctive New England “Bow House” architectural style while

    Eugene Smith TTR Sotheby's International Realty

    7705 Quaker Neck Rd, Bozman, MD 21612
  • /34

    $259,900

    • 3 Beds
    • 1.5 Baths
    • 1,336 Sq Ft

    21907 Sherwood Landing Rd, Sherwood, MD 21665

    First time offered in 60 years! Nestled in the heart of a charming waterfront village, this classic 3-bedroom, 1.5-bath Eastern Shore home exudes timeless appeal. With rich historic character and warm wood floors throughout, it’s ready for your personal touch to bring it back to life.Enjoy partial water views and the convenience of a county pier and kayak launch just down the street, providing

    Wink Cowee Benson & Mangold, LLC

    21907 Sherwood Landing Rd, Sherwood, MD 21665
  • /47

    $2,495,000

    • 3 Beds
    • 3.5 Baths
    • 3,847 Sq Ft

    21825 Langdon Farm Rd, Sherwood, MD 21665

    It doesn't get any better than this ! Stunning brand-new ,one-story coastal residence with a contemporary flair! As soon as you enter this magnificent home, you will be captivated by 20'+ ceilings, superb craftsmanship , an extremely well-designed open floor-plan; breathtaking water-views on Dun Cove and a luxurious yet inviting kitchen. There are a total of 3 en-suite bedrooms as well as an

    Robert Lacaze TTR Sotheby's International Realty

    21825 Langdon Farm Rd, Sherwood, MD 21665
  • /33

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,570 Sq Ft

    6394 Bozman Neavitt Rd, Neavitt, MD 21652

    If you like old houses, you will love this one! Built by a member of the Neavitt family c. 1870, it has been extensively renovated by the present owner. The light-filled first floor boasts a charming living room with built-ins and original chimney, spacious dining room, small sunny bedroom/office, full bath, and lovely kitchen opening to a patio. A spacious bedroom with a glimpse of Balls Creek

    Joan Wetmore TTR Sotheby's International Realty

    6394 Bozman Neavitt Rd, Neavitt, MD 21652
  • /58

    $560,000

    • 3 Beds
    • 2.5 Baths
    • 2,110 Sq Ft

    5582 Trafalgar Cir, Tilghman, MD 21671

    The Nottingham, (elevation Z) is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2-car garage with entry through a mudroom that leads to an expansive Great Room area that opens to the Kitchen. The Kitchen is ready for entertaining and cooking comforting meals for family and friends. An open dinette and large kitchen island offer a plethora of space for informal dining. You can take

    Stacie Luhrman Benson & Mangold, LLC

    5582 Trafalgar Cir, Tilghman, MD 21671
  • /22

    $189,900

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft

    8034 Bozman Neavitt Rd, Bozman, MD 21612

    Great opportunity to buy below market value. House needs work, but opportunity is endless. Sold strictly AS IS. Seller and listing agent do not guarantee accuracy in this listing. Buyer must do their own due diligence before submitting an offer. Cash or Hard Money only. Seller prefers New World Title Company.

    Alex Fox Allfirst Realty, Inc.

    8034 Bozman Neavitt Rd, Bozman, MD 21612
  • /17

    $550,000

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    6343 Bozman Neavitt Rd, Neavitt, MD 21652

    Rustic Charm on Balls Creek - Wake up to sunrise views over Balls Creek from this charming 2-bedroom waterfront cottage. With nearly 200 feet of water frontage and a private pier, this serene retreat is perfect for weekend escapes filled with fishing, kayaking, or simply unwinding by the water’s edge. The cozy, nostalgic layout features a living room with wood floors, a dining area, and an

    Kathy Christensen TTR Sotheby's International Realty

    6343 Bozman Neavitt Rd, Neavitt, MD 21652
  • /46

    $495,000

    • 3 Beds
    • 3.5 Baths
    • 1,504 Sq Ft

    8013 Ruby Harrison Rd, Bozman, MD 21612

    What a transformation this Victorian beauty has undergone! With high ceilings, new windows, and gorgeous engineered wide plank wood floors, the downstairs is open and light. A stylish kitchen with island overlooks the dining area and large sliders open to a private side yard, where glimpses of nearby Harris Creek may be seen. The front room provides a comfortable seating area. Upstairs are

    Debra Crouch Benson & Mangold, LLC

    8013 Ruby Harrison Rd, Bozman, MD 21612
  • /134

    $1,599,900

    • 4 Beds
    • 3 Baths
    • 2,731 Sq Ft

    9175 Mallard Point Ct, McDaniel, MD 21647

    PROFESSIONAL PHOTOS TO COME!Experience luxury at its finest on Harris Creek with this stunning newly remodeled 4 bedroom, 3 bathroom custom home designed and meticulously remodeled by RBCI, Inc., an award-winning custom home builder. No expense was spared in creating this 2,731 sq. ft. masterpiece on over 1.5 acres of magnificent waterfront living. New flooring, counter tops, appliances,

    Ann Holtz Coldwell Banker Realty

    9175 Mallard Point Ct, McDaniel, MD 21647
  • /41

    $499,000

    • 3 Beds
    • 1.5 Baths
    • 5,344 Sq Ft

    7683 Tilghman Island Rd, Sherwood, MD 21665

    BACK ON MARKET-by no fault of Seller. Welcome to this beautifully updated 3-bedroom, 1.5-bath home, offering both charm and versatility. The home features three spacious bedrooms, including one with an attached area that can serve as a walk-in closet, nursery, or home office—perfect for adapting to your needs. With 1.5 bathrooms, you'll enjoy the convenience of a full bath and an additional half

    Katie Mister Keller Williams Select Realtors of Cambridge

    7683 Tilghman Island Rd, Sherwood, MD 21665
  • /21

    $309,500

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    8898 New Rd, Wittman, MD 21676

    Welcome to this charming 3-bedroom, 2-bathroom stick built rancher nestled in the heart of beautiful Talbot County, Maryland. Situated on a spacious, landscaped lot, this home offers a perfect blend of modern comforts and classic appeal. The open floor plan features a light-filled living area that seamlessly flows into a cozy dining space, making it ideal for gatherings. The updated kitchen

    BJ Kilby EXIT On The Bay

    8898 New Rd, Wittman, MD 21676
  • /2

    $102,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    9681 Macks Ln, McDaniel, MD 21647

    Please don’t enter the home. The value is in the land.

    Lesley Jackson EXIT Sunshine Realty

    9681 Macks Ln, McDaniel, MD 21647
  • /14

    $509,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    5654 Trafalgar Cir, Tilghman, MD 21671

    The New Castle is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2 car garage with drop zone entry, attached to a laundry room, that leads through to the Kitchen. The Kitchen has a large amount of space, plenty of cabinets, and a pantry, making storage and organization plentiful and manageable. The well-equipped kitchen is ready for entertaining and with family and friends. The open

    Mary Ann Hammel Mary Ann Hammel

    5654 Trafalgar Cir, Tilghman, MD 21671
  • /10

    $425,000 Open House 6/14

    • 2 Beds
    • 3 Baths
    • 1,776 Sq Ft

    7651 Main St, Sherwood, MD 21665

    CHARMING SHERWOOD VILLAGE WITH ITS RICH HISTORY. ONE OF THE BEST KEPT SECRETS.STEP BACK IN TIME, WONDER PAST BEAUTIFUL GARDENS UNDER SHADE TREES, GET GREETED BY THE PEACEFUL SETTING . THE COMMUNITY DOCK WITH MULTIPLE SLIPS AND FLOATING DOCK , THE KAYAK LANDING, IS A NEIGHBORHOOD HANG OUT, VERY POPULAR AT SUNSET TIME TO ENJOY GLORIOUS SUNSETS WITH WIDE OPEN VIEWS OVER HARRIS CREEK.THIS HOME HAS

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7651 Main St, Sherwood, MD 21665
  • /15

    $165,000

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    6369 Neavitt Manor Rd, Neavitt, MD 21652

    Price adjustment! Opportunity abounds in this lovely 2 Bedroom 1 Bath detached home located in the picturesque waterfront town of Neavitt. This home boasts central air, attic space, a large yard, a shed and much more. Close to St. Michales and Tilghman Island this is a boaters and bird lovers paradise with a public boat ramp about a 1/2 mile away plus stores, shops , dining and

    Richard Perrera Century 21 Downtown

    6369 Neavitt Manor Rd, Neavitt, MD 21652
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