25

Sherwood, MD Homes for Sale with Garage

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  • 6660 Reeses Pride Rd, Sherwood, MD 21665
    6660 Reeses Pride Rd, Sherwood, MD 21665
    6660 Reeses Pride Rd, Sherwood, MD 21665
    /72

    $765,000

    • 3 Beds
    • 2.5 Baths
    • 2,240 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
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /43

    $544,888 New Construction

    • 3 Beds
    • 2 Baths
    • 2,068 Sq Ft

    5648 Trafalgar Cir, Tilghman, MD 21671

    Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center

    Kim Crouch Ozman Benson & Mangold, LLC

    5648 Trafalgar Cir, Tilghman, MD 21671
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /44

    $1,195,000

    • 3 Beds
    • 3 Baths
    • 2,085 Sq Ft

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to Old House Cove Waterfront Retreat in St. Michaels, MDNestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of

    Kathleen Eder Compass

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
  • 6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    /64

    $1,299,000

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

    6670 Tilghman Island Rd, Sherwood, MD 21665

    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 lighting.

    Larry Brennan TTR Sotheby's International Realty

    6670 Tilghman Island Rd, Sherwood, MD 21665
  • 21825 Langdon Farm Rd, Sherwood, MD 21665
    21825 Langdon Farm Rd, Sherwood, MD 21665
    21825 Langdon Farm Rd, Sherwood, MD 21665
    /47

    $2,395,000

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

    Laura Carney TTR Sotheby's International Realty

    7090 Cooper Point Rd, Bozman, MD 21612
  • 21907 Sherwood Landing Rd, Sherwood, MD 21665
    21907 Sherwood Landing Rd, Sherwood, MD 21665
    21907 Sherwood Landing Rd, Sherwood, MD 21665
    /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
  • 22707 Marshall Ln, Wittman, MD 21676
    22707 Marshall Ln, Wittman, MD 21676
    22707 Marshall Ln, Wittman, MD 21676
    /43

    $2,195,000 Coming Soon

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

    22707 Marshall Ln, Wittman, MD 21676

    Exceptional custom waterfront home on Harris Creek offering an ideal setting for boating, kayaking, paddleboarding and relaxed days on the water. Perfectly suited for a discerning second-home buyer or full-time Eastern Shore living, this five-bedroom, three-and-a-half-bath residence blends thoughtful design with an effortless waterfront lifestyle. A dramatic two-story foyer welcomes you into

    Kathy Christensen TTR Sotheby's International Realty

    22707 Marshall Ln, Wittman, MD 21676
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /62

    $575,000

    • 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
  • 5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    /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
  • 6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    /74

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 3,232 Sq Ft

    6050 Sunset Ln, Tilghman, MD 21671

    Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    6050 Sunset Ln, Tilghman, MD 21671
  • 9262 Macks Ln, McDaniel, MD 21647
    9262 Macks Ln, McDaniel, MD 21647
    9262 Macks Ln, McDaniel, MD 21647
    /89

    $2,998,000

    • 4 Beds
    • 6 Baths
    • 5,400 Sq Ft

    9262 Macks Ln, McDaniel, MD 21647

    Just 5-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings

    Tom Crouch Benson & Mangold, LLC

    9262 Macks Ln, McDaniel, MD 21647
  • 23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    /81

    $3,100,000

    • 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
  • 21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    /83

    $2,499,000

    • 5 Beds
    • 4.5 Baths
    • 4,303 Sq Ft

    21485 Island Club Rd, Tilghman, MD 21671

    Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting.

    Alicia Gannon Dulin Benson & Mangold, LLC

    21485 Island Club Rd, Tilghman, MD 21671
  • 7651 Main St, Sherwood, MD 21665
    7651 Main St, Sherwood, MD 21665
    7651 Main St, Sherwood, MD 21665
    /35

    $425,000

    • 2 Beds
    • 2 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

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7651 Main St, Sherwood, MD 21665
  • 5489 Rude Ave, Tilghman, MD 21671
    5489 Rude Ave, Tilghman, MD 21671
    5489 Rude Ave, Tilghman, MD 21671
    /65

    $850,000

    • 4 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    5489 Rude Ave, Tilghman, MD 21671

    Spacious 3,000 sqft two-story waterfront home on 3/4 acre parcel on Harris Creek where it joins the Choptank River for an 11-mile view to Cambridge. House is brick and block on the first level with redwood siding on the second level in board and batten style. 150ft heavily built and reinforced bulkhead waterfront with recently renovated 75ft long dock. Second floor includes four bedrooms with

    Leo Kuneman Meredith Fine Properties

    5489 Rude Ave, Tilghman, MD 21671
  • 8781 Tilghman Island Rd, Wittman, MD 21676
    8781 Tilghman Island Rd, Wittman, MD 21676
    8781 Tilghman Island Rd, Wittman, MD 21676
    /60

    $3,795,000

    • 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
  • 21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    /50

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 3,040 Sq Ft

    21477 Island Club Rd, Tilghman, MD 21671

    Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    21477 Island Club Rd, Tilghman, MD 21671
  • 21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    /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 used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water. The buildings hold virtually no value unless and extensive historic renovation were completed. Tilghman is an historic waterfront town that features a waterman's museum, marina, many restaurants, established

    Monica Penwell TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • 5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    /49

    $499,888 New Construction

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

    5654 Trafalgar Cir, Tilghman, MD 21671

    Kim Crouch Ozman Benson & Mangold, LLC

    5654 Trafalgar Cir, Tilghman, MD 21671
  • 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
  • 6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    /47

    $1,745,000

    • 6 Beds
    • 6 Baths
    • 4,397 Sq Ft

    6020 Sunset Ln, Tilghman, MD 21671

    Welcome to Tilghman Landing on the Chesapeake Bay! This unique waterview property offers an incredible opportunity, featuring two separate homes with garages with unbelievable views of the Bay!Home #1: 6020 Sunset LaneThis spacious residence offers breathtaking, unobstructed views of the Bay. It includes 3 bedrooms and 2.5 bathrooms, and showcases an open-concept main level with a living

    Melissa Tippett TTR Sotheby's International Realty

    6020 Sunset Ln, Tilghman, MD 21671
  • 22314 Pot Pie Rd, Wittman, MD 21676
    22314 Pot Pie Rd, Wittman, MD 21676
    22314 Pot Pie Rd, Wittman, MD 21676
    /14

    $325,000

    • 3 Beds
    • 2 Baths
    • 3,924 Sq Ft

    22314 Pot Pie Rd, Wittman, MD 21676

    Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84± commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment,

    Shawn Moore Meredith Fine Properties

    22314 Pot Pie Rd, Wittman, MD 21676
Maryland Talbot County Sherwood

Homes for Sale with Garage in Sherwood, MD

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In Sherwood, there are currently 25 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Sherwood, MD and find the perfect place to call home.

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