49

Sherwood, MD Homes for Sale

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  • 5698 Leeward Ln, Tilghman, MD 21671
    5698 Leeward Ln, Tilghman, MD 21671
    5698 Leeward Ln, Tilghman, MD 21671
    /41

    $1,995,000

    • 5 Beds
    • 3.5 Baths
    • 3,906 Sq Ft

    5698 Leeward Ln, Tilghman, MD 21671

    Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat in Tilghman Island. Thoughtfully redesigned and updated in 2023, this exceptional property seamlessly blends refined coastal living with the tranquility and natural beauty of its extraordinary waterfront setting.Inside, the light-filled great room is the heart of the home, with

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    5698 Leeward Ln, Tilghman, MD 21671
  • 21406 Dogwood Cove Rd, Tilghman, MD 21671
    21406 Dogwood Cove Rd, Tilghman, MD 21671
    21406 Dogwood Cove Rd, Tilghman, MD 21671
    /68

    $410,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    21406 Dogwood Cove Rd, Tilghman, MD 21671

    Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    21406 Dogwood Cove Rd, Tilghman, MD 21671
  • 22101 Grafton Manour Ln, Wittman, MD 21676
    22101 Grafton Manour Ln, Wittman, MD 21676
    22101 Grafton Manour Ln, Wittman, MD 21676
    /134

    $7,800,000

    • 4 Beds
    • 4.5 Baths
    • 7,407 Sq Ft

    22101 Grafton Manour Ln, Wittman, MD 21676

    Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    22101 Grafton Manour Ln, Wittman, MD 21676
  • 5933 Tilghman Island Rd, Tilghman, MD 21671
    5933 Tilghman Island Rd, Tilghman, MD 21671
    5933 Tilghman Island Rd, Tilghman, MD 21671
    /35

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    5933 Tilghman Island Rd, Tilghman, MD 21671

    Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    5933 Tilghman Island Rd, Tilghman, MD 21671
  • 6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    /64

    $1,099,000

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

    6670 Tilghman Island Rd, Sherwood, MD 21665

    Reduced Price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. 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

    6670 Tilghman Island Rd, Sherwood, MD 21665
  • 0 Sinclair Ave, Tilghman Island, MD 21671
    0 Sinclair Ave, Tilghman Island, MD 21671
    0 Sinclair Ave, Tilghman Island, MD 21671
    /10

    $68,500

    $7K PRICE DROP
    • Land
    • 13,068 Sq Ft
    • $228,333 per Acre

    0 Sinclair Ave, Tilghman Island, MD 21671

    Build your dream home on beautiful Tilghman Island! This ideally located lot is within walkingdistance of Sinclair Community Park, local marinas, charming shops, and popular waterfrontrestaurants. Stroll to the end of your street to enjoy stunning Chesapeake Bay sunsets from thepark’s scenic shoreline.Tilghman Island is a beloved Eastern Shore destination known for its rich

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    0 Sinclair Ave, Tilghman Island, MD 21671
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /75

    $564,000

    $5K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,404 Sq Ft

    5559 Trafalgar Cir, Tilghman, MD 21671

    TILGHMAN ISLAND.Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    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

    $72,500

    $8K PRICE DROP
    • Land
    • 13,068 Sq Ft
    • $241,667 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

    21472 Willey Rd, Tilghman, MD 21671
  • 8612 Tilghman Island Rd, Wittman, MD 21676
    8612 Tilghman Island Rd, Wittman, MD 21676
    8612 Tilghman Island Rd, Wittman, MD 21676
    /72

    $5,995,000

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

    8612 Tilghman Island Rd, Wittman, MD 21676

    See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "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

    Laura Carney TTR Sotheby's International Realty

    8612 Tilghman Island Rd, Wittman, MD 21676
  • 21647 Camper Cir, Tilghman, MD 21671
    21647 Camper Cir, Tilghman, MD 21671
    21647 Camper Cir, Tilghman, MD 21671
    /25

    $295,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 1 Bath
    • 1,262 Sq Ft

    21647 Camper Cir, Tilghman, MD 21671

    Welcome to 21647 Camper Circle in the charming waterfront community of Tilghman Island. This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features

    Heather Brummell Keller Williams Realty

    21647 Camper Cir, Tilghman, MD 21671
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /43

    $529,888

    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
  • 6394 Bozman Neavitt Rd, Neavitt, MD 21652
    6394 Bozman Neavitt Rd, Neavitt, MD 21652
    6394 Bozman Neavitt Rd, Neavitt, MD 21652
    /29

    $515,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,570 Sq Ft

    6394 Bozman Neavitt Rd, Neavitt, MD 21652

    Just 12 miles from St Michaels, this house is in a quiet community of 60+ homes at the end of a lovely peninsula. A public landing is at the end of Bozman Neavitt Road, and a community center and park are in the heart of the village.This property has been renovated and updated from the studs out. Features now include 2-3 Bedrooms 2 Full baths Living room with built-ins Light-filled kitchen

    Joan Wetmore TTR Sotheby's International Realty

    6394 Bozman Neavitt Rd, Neavitt, MD 21652
  • 6403 Bozman Neavitt Rd, Neavitt, MD 21652
    6403 Bozman Neavitt Rd, Neavitt, MD 21652
    6403 Bozman Neavitt Rd, Neavitt, MD 21652
    /30

    $435,500

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

    6403 Bozman Neavitt Rd, Neavitt, MD 21652

    Located about 12 miles from St Michaels, this home is in Neavitt, a charming village of 60+ houses at the end of a peninsula. It's in another, quieter world. The village has its own park and playground, a public landing with a launch for canoes, and an active community association. 6403 was renovated and expanded in 2011 and the layout adapted for modern living, with light-filled rooms, a

    Joan Wetmore TTR Sotheby's International Realty

    6403 Bozman Neavitt Rd, Neavitt, MD 21652
  • 7090 Cooper Point Rd, Bozman, MD 21612
    7090 Cooper Point Rd, Bozman, MD 21612
    7090 Cooper Point Rd, Bozman, MD 21612
    /86

    $6,800,000

    $700K PRICE DROP
    • 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
  • 8805 Cummings Rd, Wittman, MD 21676
    8805 Cummings Rd, Wittman, MD 21676
    8805 Cummings Rd, Wittman, MD 21676
    /39

    $375,000

    $10K PRICE DROP
    • 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
  • 21642 Chicken Point Rd, Tilghman, MD 21671
    21642 Chicken Point Rd, Tilghman, MD 21671
    21642 Chicken Point Rd, Tilghman, MD 21671
    /144

    $2,475,000

    $220K PRICE DROP
    • 7 Beds
    • 5.5 Baths
    • 4,151 Sq Ft

    21642 Chicken Point Rd, Tilghman, MD 21671

    "Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21642 Chicken Point Rd, Tilghman, MD 21671
  • 7543 Bozman Neavitt Rd, Bozman, MD 21612
    7543 Bozman Neavitt Rd, Bozman, MD 21612
    7543 Bozman Neavitt Rd, Bozman, MD 21612
    /104

    $2,750,000

    • 4 Beds
    • 3 Baths
    • 6,361 Sq Ft

    7543 Bozman Neavitt Rd, Bozman, MD 21612

    This stunning waterfront estate is located just minutes from Historic downtown St. Michaels and offers breathtaking views across Leadenham Creek. Set on 47± picturesque acres, the property combines a beautifully renovated main residence, guest house, private dock, waterside pool and expansive open land in one exceptional Eastern Shore offering. Renovated in 2017, the 3,500± sqft brick residence

    Kim Crouch Ozman Benson & Mangold, LLC

    7543 Bozman Neavitt Rd, Bozman, MD 21612
  • 0 Quaker Neck Rd, Bozman, MD 21612
    0 Quaker Neck Rd, Bozman, MD 21612
    0 Quaker Neck Rd, Bozman, MD 21612
    /6

    $800,000

    • Land
    • 10.48 Acres
    • $76,336 per Acre

    0 Quaker Neck Rd, Bozman, MD 21612

    This exceptional 10.48 acre parcel of land offers a rare opportunity to embrace an exclusive lifestyle. With an impressive 461+/- feet of waterfront along the picturesque Sandy Point Cove leading to Broad Creek, this property is a haven for privacy. Enjoy private access to the water, ideal for fishing, canoeing, and kayaking. The expansive lot offers ample space for the creation of a luxurious

    Melissa Tippett TTR Sotheby's International Realty

    0 Quaker Neck Rd, Bozman, MD 21612
  • 8658 Cummings Rd, Wittman, MD 21676
    8658 Cummings Rd, Wittman, MD 21676
    8658 Cummings Rd, Wittman, MD 21676
    /45

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    8658 Cummings Rd, Wittman, MD 21676

    Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry,

    Kim Crouch Ozman Benson & Mangold, LLC

    8658 Cummings Rd, Wittman, MD 21676
  • 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
  • 9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    /38

    $449,900

    • 4 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    9818 Tilghman Island Rd, McDaniel, MD 21647

    The Perfect Blend of Space & Proximity. Loved by one family, this 4 bedroom 2 1/2 bath home is ready for the next owner. Situated on a beautiful1-acre parcel, this property is framed by magnificent, beautifully spaced mature trees and a cool gazebo to enjoy the park-like setting. Located in desirable McDaniel, you enjoy the ultimate Eastern Shore lifestyle: peaceful rural privacy, no HOA, and a

    Valerie Brown Coldwell Banker Realty

    9818 Tilghman Island Rd, McDaniel, MD 21647
  • 9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /32

    $1,995,000

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

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663

    Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long,

    Tom Crouch Benson & Mangold, LLC

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    /68

    $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
  • 21560 Chicken Point Rd, Tilghman, MD 21671
    21560 Chicken Point Rd, Tilghman, MD 21671
    21560 Chicken Point Rd, Tilghman, MD 21671
    /78

    $845,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,314 Sq Ft

    21560 Chicken Point Rd, Tilghman, MD 21671

    Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21560 Chicken Point 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

    $1,950,000

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

    21485 Island Club Rd, Tilghman, MD 21671

    Back on the market due to Buyers unable to fulfill home sale contingency- 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

    Alicia Gannon Dulin Benson & Mangold, LLC

    21485 Island Club Rd, Tilghman, MD 21671
  • 21869 Albie Rd, Sherwood, MD 21665
    21869 Albie Rd, Sherwood, MD 21665
    21869 Albie Rd, Sherwood, MD 21665
    /39

    $519,000

    $56K PRICE DROP
    • 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
  • 7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    /59

    $1,795,000

    Open House 8/08 $200K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,352 Sq Ft

    7421 Quaker Neck Rd, Bozman, MD 21612

    Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents arare opportunity to own an expansive estate with exceptional shoreline frontage. With more than960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offeringdirect access to the creek and surrounding natural landscape. A tree-lined private

    Chuck Mangold Benson & Mangold, LLC

    7421 Quaker Neck Rd, Bozman, MD 21612
  • 6390 Bozman Neavitt Rd, Neavitt, MD 21652
    6390 Bozman Neavitt Rd, Neavitt, MD 21652
    6390 Bozman Neavitt Rd, Neavitt, MD 21652
    /39

    $449,000

    $66K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft

    6390 Bozman Neavitt Rd, Neavitt, MD 21652

    The perfect renovated, water view cottage, dating back to circa 1890. Has been meticulously maintained and thoughtfully expanded over the years. Located in the waterfront Village of Neavitt (+/- 70 homes). Move-in mint condition with numerous recent upgrades. First floor primary bedroom, first floor renovated full bathroom, two additional bedrooms and full bathroom upstairs. Outdoor Living: A

    Brian Petzold Benson & Mangold, LLC

    6390 Bozman Neavitt Rd, Neavitt, MD 21652
  • 5480 Windward Dr, Tilghman, MD 21671
    5480 Windward Dr, Tilghman, MD 21671
    5480 Windward Dr, Tilghman, MD 21671
    /59

    $1,250,000

    • 4 Beds
    • 3 Baths
    • 1,936 Sq Ft

    5480 Windward Dr, Tilghman, MD 21671

    Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting

    Kim Crouch Ozman Benson & Mangold, LLC

    5480 Windward Dr, Tilghman, MD 21671
  • 8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    /33

    $993,000

    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    8090 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled in the serene enclave of Bozman, this exquisite 1940s bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed with high-end finishes that elevate everyday living. The country-style kitchen

    Bill Wieland Benson & Mangold, LLC

    8090 Bozman Neavitt Rd, Bozman, MD 21612
  • 21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    /50

    $1,150,000

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

    21477 Island Club Rd, Tilghman, MD 21671

    PRICE IMPROVEMENT*** 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

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    21477 Island Club Rd, Tilghman, MD 21671
  • 21552 Chicken Point Rd, Tilghman, MD 21671
    21552 Chicken Point Rd, Tilghman, MD 21671
    21552 Chicken Point Rd, Tilghman, MD 21671
    /71

    $945,000

    $50K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,655 Sq Ft

    21552 Chicken Point Rd, Tilghman, MD 21671

    Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor primary suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21552 Chicken Point Rd, Tilghman, MD 21671
  • 8000 Bozman Neavitt Rd, Bozman, MD 21612
    8000 Bozman Neavitt Rd, Bozman, MD 21612
    8000 Bozman Neavitt Rd, Bozman, MD 21612
    /57

    $479,000

    $111K PRICE DROP
    • 3 Beds
    • 2 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
  • 5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    /49

    $489,888

    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
  • 21524 Chicken Point Rd, Tilghman, MD 21671
    21524 Chicken Point Rd, Tilghman, MD 21671
    21524 Chicken Point Rd, Tilghman, MD 21671
    /55

    $339,000

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,761 Sq Ft

    21524 Chicken Point Rd, Tilghman, MD 21671

    Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your

    Debbie Lipscomb Benson & Mangold, LLC

    21524 Chicken Point Rd, Tilghman, MD 21671
  • 8612 Tilghman Island Rd, Wittman, MD 21676
    8612 Tilghman Island Rd, Wittman, MD 21676
    8612 Tilghman Island Rd, Wittman, MD 21676
    /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 114+-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
  • 22582 Pot Pie Rd, Wittman, MD 21676
    22582 Pot Pie Rd, Wittman, MD 21676
    22582 Pot Pie Rd, Wittman, MD 21676
    /33

    $399,900

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,556 Sq Ft

    22582 Pot Pie Rd, Wittman, MD 21676

    Set on nearly an acre in the heart of Wittman, this cedar shake–sided home offers space, character, and a relaxed Eastern Shore lifestyle. Built in 1900, the 3-bedroom, 1.5-bath residence blends timeless charm with thoughtful updates for comfortable everyday living. Hardwood flooring runs throughout, complemented by a sun-filled dining room and a cozy living room with a gas fireplace and built-in

    Chuck Mangold Benson & Mangold, LLC

    22582 Pot Pie Rd, Wittman, MD 21676
  • 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

Showing Results 1 - 40, Page 1 of 2

Maryland Talbot County

Real Estate & Homes 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 21663.
What are the most popular neighborhoods near Sherwood, MD?
The most popular neighborhoods near Sherwood, MD are Romancoke and Selby-on-the-Bay.
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