40

Newest Homes for Sale in Sherwood, MD

Section Image Section Image Section Image
  • 22707 Marshall Ln, Wittman, MD 21676
    22707 Marshall Ln, Wittman, MD 21676
    22707 Marshall Ln, Wittman, MD 21676
    /43

    $2,195,000

    • 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
  • 22769 Almost Neavitt Rd, Bozman, MD 21612
    22769 Almost Neavitt Rd, Bozman, MD 21612
    /2

    $799,000 Coming Soon

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

    22769 Almost Neavitt Rd, Bozman, MD 21612

    THE BEST EASTERN SHORE WATERFRONT VALUEstay tuned for professional photos next week as well as detailled description for this fabulous buy. Four bedroom charming cottage with quality renovation , exceptionally cared for and constantly upgraded for worry free enjoyment. 2026 is the planned year for the public sewer hook up which will enable the new owner to build a pool and expand adding more

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    22769 Almost Neavitt Rd, Bozman, MD 21612
  • 7508 Cooper Point Rd, Bozman, MD 21612
    7508 Cooper Point Rd, Bozman, MD 21612
    7508 Cooper Point Rd, Bozman, MD 21612
    /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
  • 21384 Coopertown Rd, Tilghman, MD 21671
    21384 Coopertown Rd, Tilghman, MD 21671
    21384 Coopertown Rd, Tilghman, MD 21671
    /25

    $5,200,000

    • 20 Beds
    • 24 Baths
    • 14,035 Sq Ft

    21384 Coopertown Rd, Tilghman, MD 21671

    *A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* NOTE: Has public sewer and well. Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance,

    Agent Photo

    Angela Simonelli

    Compass

    (410) 200-0414

    21384 Coopertown Rd, Tilghman, MD 21671
  • 6369 Neavitt Manor Rd, Neavitt, MD 21652
    6369 Neavitt Manor Rd, Neavitt, MD 21652
    6369 Neavitt Manor Rd, Neavitt, MD 21652
    /11

    $150,000

    • 1 Bed
    • 1 Bath
    • 832 Sq Ft

    6369 Neavitt Manor Rd, Neavitt, MD 21652

    Nice location, in small water front community, 15 min to St Michaels. Corner lot and drive way for parking, would make nice weekend get away or summer home. Check it out

    Bill Griffin Results Realty Inc.

    6369 Neavitt Manor Rd, Neavitt, MD 21652
  • 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
  • 5744 Johns Way, Tilghman, MD 21671
    5744 Johns Way, Tilghman, MD 21671
    5744 Johns Way, Tilghman, MD 21671
    /41

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft

    5744 Johns Way, Tilghman, MD 21671

    2 year old cottage located on Tilghman Island. 3 bedrooms and 2.5 baths, this property is perfect for full time residents or for weekend getaways. Property is located on a quite cul-de-sac and backs up to trees. Large open living room, dining area and kitchen provides enough space for family gatherings or entertaining friends. Kitchen has granite counters and stainless appliances along with a

    Rebecca Biggs

    Tilghman Island Realty Inc

    (667) 245-9539

    5744 Johns Way, Tilghman, MD 21671
  • 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 Open House 1/17

    • 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
  • 8805 Cummings Rd, Wittman, MD 21676
    8805 Cummings Rd, Wittman, MD 21676
    8805 Cummings Rd, Wittman, MD 21676
    /39

    $385,000

    • 2 Beds
    • 1.5 Baths
    • 1,364 Sq Ft

    8805 Cummings Rd, Wittman, MD 21676

    Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas and 2 office spaces . Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Meticulous renovations by a

    Wink Cowee Benson & Mangold, LLC

    8805 Cummings Rd, Wittman, MD 21676
  • 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
  • 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
  • 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
  • 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
  • 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

    $1,155,000

    • 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
  • 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
  • 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
  • 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
  • 6343 Bozman Neavitt Rd, Neavitt, MD 21652
    6343 Bozman Neavitt Rd, Neavitt, MD 21652
    6343 Bozman Neavitt Rd, Neavitt, MD 21652
    /23

    $495,500

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    6343 Bozman Neavitt Rd, Neavitt, MD 21652

    UNIQUE COTTAGE IN A GREAT VILLAGE SETING WITH A DOCK PROVIDING ACCESS TO BALL CREEK AND QUICK ACCES TO THE CHESAPEAKE WITH GREAT FISHING AND SAILING! Ready for an updating with good bones this would be a wonderful weekender or short term rental. Typical Eastern Shore rural village with great folks it can even be replaced with the home of your dreams.Dock offers a 3 foot channel and has

    Bill Wieland Benson & Mangold, LLC

    6343 Bozman Neavitt Rd, Neavitt, MD 21652
  • 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
  • 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
  • 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
  • 22349 Cooper Ln, Wittman, MD 21676
    22349 Cooper Ln, Wittman, MD 21676
    22349 Cooper Ln, Wittman, MD 21676
    /22

    $245,000

    • 2 Beds
    • 1 Bath
    • 1,270 Sq Ft

    22349 Cooper Ln, Wittman, MD 21676

    Charming farmhouse with approximately 1300 sq feet of living space on a large, picturesque lot. Perfect weekend retreat close to St. Michaels, investment property or full time residence. The second level has two bedrooms, walk-in closet, a cozy nook ideal for a home office and a recently fully renovated bathroom. First floor includes a front room suited for an office or additional full bathroom.

    Brian Petzold Benson & Mangold, LLC

    22349 Cooper Ln, Wittman, MD 21676
  • 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
  • 21721 Heavenly Haven Rd, Sherwood, MD 21665
    21721 Heavenly Haven Rd, Sherwood, MD 21665
    21721 Heavenly Haven Rd, Sherwood, MD 21665
    /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
  • 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
  • 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
  • 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
  • 9681 Macks Ln, McDaniel, MD 21647
    9681 Macks Ln, McDaniel, MD 21647
    9681 Macks Ln, McDaniel, MD 21647
    /3

    $92,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    9681 Macks Ln, McDaniel, MD 21647

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

    Lesley Jackson EXIT Sunshine Realty

    9681 Macks Ln, McDaniel, MD 21647
  • 6403 Bozman Neavitt Rd, Neavitt, MD 21652
    6403 Bozman Neavitt Rd, Neavitt, MD 21652
    6403 Bozman Neavitt Rd, Neavitt, MD 21652
    /31

    $469,500

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

    6403 Bozman Neavitt Rd, Neavitt, MD 21652

    Neavitt is a village of +/-seventy houses located at the end of a peninsula surrounded by water. About 12 miles from the shops and restaurants of St Michaels, it is in another, much more peaceful world, with its own park and playground, a public landing with a launch for canoes, and an active community association. Most residents have retired or plan to retire from professional jobs in

    Joan Wetmore TTR Sotheby's International Realty

    6403 Bozman Neavitt Rd, Neavitt, MD 21652
  • 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
  • 0 Holly Woods Rd, 5, Bay Hundred, MD 21665
    0 Holly Woods Rd, 5, Bay Hundred, MD 21665
    0 Holly Woods Rd, 5, Bay Hundred, MD 21665
    /24

    $174,900

    • Land
    • 2.49 Acres
    • $70,241 per Acre

    0 Holly Woods Rd, 5, Bay Hundred, MD 21665

    Deep Harbour Farm Sherwood 2.49. Acre Building Lot.This is one of the last remaining building lots available in this wonderful water privileged community.Located at the end of a cul-de-sac on Holly Woods Road just steps away from the community waterfront pier & boat dock. Great opportunity to build the home of your own design now or in the future.

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 222-5571

    0 Holly Woods Rd, 5, Bay Hundred, MD 21665
  • 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
  • 21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    /10

    $80,000

    • Land
    • 0.3 Acre
    • $266,667 per Acre

    21472 Willey Rd, Tilghman, MD 21671

    Tilghman Island. Clear level building lot with public sewer available. The perfect spot for your new vacation / retirement home. Excellent opportunity to make your island dream come true.

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 382-8747

    21472 Willey Rd, Tilghman, MD 21671
  • 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
  • 8034 Bozman Neavitt Rd, Bozman, MD 21612
    8034 Bozman Neavitt Rd, Bozman, MD 21612
    8034 Bozman Neavitt Rd, Bozman, MD 21612
    /22

    $179,900

    • 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
  • 0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    /12

    $75,000

    • Land
    • 0.3 Acre
    • $250,000 per Acre

    0 Sinclair Rd, Tilghman Island, MD 21671

    Sinclair Ave. Tilghman Island. Clear level building lot with public sewer. This lot is ready for you to make your dream of island life come true.Enjoy the best sunsets at the end of the street at Sinclair Community Park .

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 297-6839

    0 Sinclair Rd, Tilghman Island, MD 21671
  • 00 New Rd, McDaniel, MD 21647
    00 New Rd, McDaniel, MD 21647
    00 New Rd, McDaniel, MD 21647
    /9

    $200,000

    • Land
    • 8.03 Acres
    • $24,907 per Acre

    00 New Rd, McDaniel, MD 21647

    8.037 Acres located just west of St. Michaels, MD. All wooded and has been used primarily for hunting and fire wood. There is one and possibly two approved perc sites though they may need to be updated. Access off of New Road and Walkers Turn road, there may be an opportunity to subdivide but would need to be discussed with County Planning and Zoning. Opportunity to build your home with a lot of

    James Bent Benson & Mangold, LLC

    00 New Rd, McDaniel, MD 21647
Maryland Talbot County Sherwood

Newest Listings for Sale in Sherwood, MD

Frequently Asked Questions

What are the most popular zip codes in Sherwood, MD?
The most popular zip codes in Sherwood, MD include 21665, 21676, 21612, 21671 and 21624.
What are the most popular neighborhoods near Sherwood, MD?
The most popular neighborhoods near Sherwood, MD are Romancoke, Selby-on-the-Bay and Harwood.
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group