Sherwood Homes for Sale

Sherwood Homes for Sale

Welcome to Sherwood, Maryland—a hidden gem nestled in the picturesque Talbot County. Known for its serene landscapes and charming community, Sherwood offers a perfect blend of rural tranquility and modern convenience. This quaint area is surrounded by lush greenery, scenic waterways, and a rich tapestry of history, making it an ideal locale for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

Sherwood boasts an inviting atmosphere, where neighbors become friends and community events bring everyone together. With its proximity to the Chesapeake Bay, outdoor enthusiasts will find endless opportunities for fishing, boating, and hiking. The area is also rich in local culture, featuring delightful shops, restaurants, and art galleries that reflect the unique character of this charming town.

For those considering making Sherwood their home, you're in luck! A variety of homes for sale are currently available, catering to diverse tastes and budgets. From cozy cottages perfect for first-time buyers to spacious family homes ideal for growing households, there’s something for everyone. Many properties feature beautiful yards, modern amenities, and easy access to the stunning natural surroundings that Sherwood is known for.

Whether you’re looking for a peaceful retreat or a vibrant community to settle down in, Sherwood, MD, offers a welcoming environment and a wealth of opportunities. Explore the homes for sale today and discover the perfect place to start your next chapter in this charming enclave of Talbot County!

Newest Sherwood Homes for Sale

$575,000
4 Beds ⋅ 3 Baths
Nestled on over 2 acres in the desirable water access community of Deep Harbor Farm, this beautiful Cape Cod beams with natural light. The home features over 2,400 sqft with 4 bedrooms and 2.5 baths. The welcoming foyer overlooks a spacious dining room and leads to an open kitchen complete with white cabinetry, stainless steel appliances, breakfast bar and a large table space. Just off the kitchen, the expansive family room serves as the heart of the home with a stunning whitewashed fireplace. The first-floor primary bedroom provides convenience, while an additional main-level bedroom, currently used as an office, offers flexibility and the potential to create a larger primary suite. Upstairs, you’ll find two generously sized bedrooms, a full bath and abundant storage including eve storage and walk-in attic space. An attached 2-car garage and large detached shed add even more functionality. Enjoy the private 2-acre setting, ideal for outdoor living, gardening, or play, along with community water access, including a dock for boating, kayaking, and paddleboarding with direct access to the Chesapeake Bay, waterfront dining and some of the area’s best fishing and crabbing around.

6705 Tilghman Island Rd, Sherwood

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$1,099,000
3 Beds ⋅ 3 Baths
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 lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

6670 Tilghman Island Rd, Sherwood

Listing courtesy of TTR Sotheby's International Realty. Contact:

$3,700,000
5 Beds ⋅ 7 Baths
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 pool and children's play area. Large garage/barn to store all the water toys and pool equipment. It's currently being used as a Vacation Rental. Showings will be staggered between use.

21721 Heavenly Haven Rd, Sherwood

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

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