Sherwood Real Estate

Sherwood Real Estate

Welcome to Sherwood, Maryland, a hidden gem nestled in the heart of Talbot County! This charming community offers a unique blend of serene rural landscapes and vibrant local culture, making it an ideal place for those seeking a peaceful yet engaging lifestyle.

Sherwood is renowned for its picturesque scenery, characterized by lush greenery, tranquil waterways, and a rich tapestry of wildlife. Residents and visitors alike can enjoy leisurely strolls along the scenic trails or take advantage of the nearby Chesapeake Bay for boating, fishing, and other outdoor activities. The area is perfect for nature lovers, offering a sense of tranquility that is hard to find in more urban settings.

Despite its small-town charm, Sherwood is conveniently located just a short drive from Easton, the county seat, where you can find a variety of shopping, dining, and entertainment options. The town boasts a close-knit community atmosphere, where neighbors become friends and local events bring everyone together. From farmers' markets to seasonal festivals, there’s always something happening in Sherwood that fosters a strong sense of community.

For families, Sherwood offers access to quality schools and recreational facilities, ensuring that children have the resources they need to thrive. The area is also rich in history, with nearby historical sites that tell the story of Maryland’s past.

If you’re looking for a place that combines the beauty of nature with a warm community spirit, Sherwood, MD, is the perfect choice. Come explore all that this delightful town has to offer, and discover your next home in this charming corner of Talbot County!

Newest Listings in Sherwood

$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:

Start Your Search