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21825 Langdon Farm Rd, Sherwood
$2,125,000
3 Beds ⋅ 4 Baths
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 office, laundry room, mud room, and a grand family room, dining area and kitchen, Some notable features include: Cast iron farmhouse kitchen sink ; cast iron claw-foot bath-tub : 3/4 " solid white oak flooring; 3/4" tongue and groove ceilings; solid interior doors; Azek shaker siding; heated floors in all bathrooms; marble tile in Primary suite bathroom; ILVE 48" gas range; 150 ft. pier and a large waterside deck. Perfect home for either a primary residence or a vacation home. The prestigious Langdon farm location offers convenience to both St. Michaels and Tilghman. Owner is not responsible for any road maintenance as their lot is still on County Road.

21825 Langdon Farm Rd, Sherwood

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

Selling Office: Taylor Properties.

7650 Ferry Cove Rd, Sherwood
$1,505,000
3 Beds ⋅ 4 Baths
Discover this stunning, custom-built waterfront Cape Cod nestled in Ferry Cove, Sherwood, a serene setting that is located right next door to a HGTV dream home! Newly constructed in 2024, this home offers the ultimate blend of luxury and comfort. Owners enjoy direct access to a beautiful sandy beach with 186 feet of waterfrontage on the Chesapeake Bay, creating the perfect space for both relaxation and entertaining guests. Step into the modern kitchen, which features ample storage, an oversized island, and an eye-catching glass backsplash. The open floor plan is designed for seamless entertaining, while a cozy fireplace provides warmth and ambiance on chilly evenings. The main level primary suite boasts breathtaking water views and an owner's suite that is sure to impress. Upstairs, a spacious loft opens to a second balcony deck that overlooks Ferry Cove—perfect for watching sunsets on warm evenings. Each of the two bedrooms includes a private bath, and the second room features a large bonus room situated above the oversized two-car garage. This flexible space offers numerous possibilities to suit your lifestyle needs. Set on over 5.5 acres, the property delivers privacy, water access, and the luxury of your own private sandy beach. There is also plenty of space for storage for your hobbies with a 36x42 pole barn added to the property in 2025. Experience modern amenities and an inviting coastal lifestyle in this exceptional retreat. Whether you seek a year-round residence or a getaway, this property offers an idyllic setting to enjoy the best of waterfront living.

7650 Ferry Cove Rd, Sherwood

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Meredith Fine Properties.

6660 Reeses Pride Rd, Sherwood
$729,000
3 Beds ⋅ 3 Baths
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, mature landscaping and hardscaped patio with built in fire/grilling pit. Built in 2005, this home boasts an open floor plan and flow that welcomes you the moment you step inside. Rich hardwood floors add an elegant touch to the interior living spaces, which have all been freshly painted throughout. The kitchen includes a combination of warm wood cabinetry, granite countertops, and stylish modern appliances, creating a culinary haven for both everyday meals and entertaining. Adjacent to the kitchen, enjoy a spacious, sunlit dining area overlooking the pool and patio. Two additional living room areas complete the setting for endless year-round indoor/outdoor activities and gatherings. A convenient laundry/mudroom includes a large capacity, front-load, Maytag washer & Dryer w/pedestals and added built-in cabinets for extra kitchen storage, pool towels and more! A brand new 600 sq ft (pet friendly) family room is a huge bonus! Designed with low-maintenance wood look ceramic plank tile flooring, high ceilings, sun drenched windows, French doors and electric fireplace, this can easily provide the ideal space for a home studio, or be furnished as a traditional gathering place for holidays and special celebrations – providing direct access to a lush grass-filled, fenced yard area that leads to the side entrance to a custom designed oversized detached 24'x48' insulated garage with separate 200-amp electric service for recreational hobbies and/or storage needs. On the second floor of the home, discover a spacious primary suite, featuring two large walk-in closets and en-suite bath with plenty of natural light, a brand new double sink vanity and fixtures; tons of personal storage space, an oversized soaking tub, and a separate shower. Two additional bedrooms also include walk-in closets, and for those seeking versatility in their space, there is a bonus/play/gaming room with a separate area for study/small home office space. All interior spaces include new blinds and window treatments throughout. If you're dreaming of a waterfront lifestyle without the waterfront price...look no further. The Deep Harbour Farm waterfront community includes a multi-slip boat dock for exclusive use by residents (slips subject to availability each year) and kayak/SUP launch and storage racks. Additional highlights of this property include solar panels which keep electric costs at a minimum. All new dual Air-Conditioning units; fully encapsulated crawl space; expansive attic space; charming covered front porch; brand-new separate 10’x20’ Amish-built garden shed just to name a few! Don’t miss out on this rare opportunity to settle into a prime coastal community and the unique lifestyle of the Eastern Shore, where history and modern amenities truly come together. Conveniently located a short distance from the Village of St. Michaels, within minutes of marinas and public boat ramps offering access to the Chesapeake Bay and the surrounding tributaries where you can enjoy miles of open bike trails, deep water fishing, crabbing and all that life on the Bay has to offer. --

6660 Reeses Pride Rd, Sherwood

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Coldwell Banker Realty - Washington.

21939 Sherwood Landing Rd, Sherwood
$700,000
3 Beds ⋅ 2 Baths
OPEN HOUSE CANCELED. Homes like these rarely come along in Talbot County: a totally updated cottage with a beautiful in-ground saltwater swimming pool and every update imaginable – all less than 300 feet from the Sherwood Landing pier, where you might launch your kayak, take a morning swim, or even dock your boat for the season. You’ll enjoy greeting neighbors on sunny mornings and cool afternoon naps on the lovely screened porch. Just inside, you’ll find a beautiful living room with so many original early 1900’s details, including an antiqued farmhouse staircase, hardwood floors, and a beautiful mantle and fireplace (propane-fired but easily converted back to wood). There is also a cozy family room that can easily be used as a first-floor bedroom, a powder room, a laundry closet, and a gorgeous kitchen fully remodeled in 2019. The kitchen features a large center island hub, granite counters, new cabinetry, and replaced appliances, including a gas cooking range, plus an enlarged Pella bay window above the sink that offers sunny views of the backyard and pool. Just off the kitchen is a dining area with banquette seating and a neat wet bar, easily accessed through replaced Pella sliders to the expansive rear deck. This home is built for entertaining! Upstairs, you will be pleased to find 3 nicely proportioned bedrooms, all with hardwood flooring and two of which have views over Harris Creek’s Waterhole Cove. A full bath features more original detailing along with a jetted bathtub. A small basement with an encapsulated crawl space houses many of the home’s systems, including the water heater, a sump pump, and a zoned hybrid fuel heat pump (2023) with oil-fired backup. A second heat pump (2010) in the attic services the top floor. While the interior of this home offers so much charm and character, along with every thoughtful amenity possible, the real star of the show is the fenced rear yard. The sellers have invested years of sweat equity into creating a beautifully landscaped backyard oasis complete with a kidney-shaped saltwater concrete pool with travertine decking. The gardens burst all season with hydrangea, verbena, hibiscus, crepe myrtle, and many native perennials. The large deck offers multiple dining and entertaining areas for summer cookouts and crab feasts. Bonus! A single bay garage provides ample storage for all your bikes, boats, tools, and yard and pool equipment. A full list of updates and upgrades is available, including but not limited to: 50 year architectural shingle roof (2025), front porch (2025), heat pump (2023), blown in hardpack insulation (2018), chimney liners and flue (2021), whole house water treatment system (2021), oil tank (2021), kitchen (2019) and over $35,000 of landscaping and hardscaping. The list goes on and on. Life in Talbot County's quaint Village of Sherwood doesn't get much better than this. You’ll be nestled solidly on the banks of Waterhole Cove on the Harris Creek and in the heart of this small community of approximately 20 turn-of-the-Century homes. An 8-minute drive from Saint Michaels, Sherwood is known for its friendly, caring neighbors, beautiful sunrises, community pier enjoyed by residents, and a wonderful 4th of July celebration.

21939 Sherwood Landing Rd, Sherwood

Listing courtesy of Compass. Contact:

Selling Office: Non Subscribing Office.

21869 Albie Rd, Sherwood
$495,000
3 Beds ⋅ 2 Baths
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 washer and dryer. Located at the end of a cul de sac with mature trees and a great water view of Harris Creek and Sherwood landing. A truly unique opportunity!

21869 Albie Rd, Sherwood

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

7651 Main St, Sherwood
$385,000
2 Beds ⋅ 2 Baths
Located in the heart of historic Sherwood Village, this beautifully restored Eastern Shore home blends classic architecture with thoughtful modern updates. The charming façade, covered entry, and detached garage/workshop with electric set the tone, while inside you’ll find sun-filled rooms, warm wood floors, shiplap accents, exposed beams, and a brick hearth with gas stove insert. The dining room opens through French doors to a spacious screened porch, creating effortless indoor-outdoor living. The kitchen features cherry cabinetry, granite countertops, and generous storage. A first-floor full bath offers a subway-tiled walk-in shower, while upstairs two comfortable bedrooms share a bath with walk-in shower and clawfoot tub. Recent improvements include an encapsulated crawlspace, 2025 standing seam metal roof, new BAT septic system, new well, updated HVAC, and Rinnai tankless hot water heater. Mature landscaping provides privacy, and residents enjoy access to the nearby community dock with slips, floating dock, kayak launch, and sweeping sunset views over Harris Creek. Just a short drive to St. Michaels and Tilghman Island, this property offers timeless village charm with modern reliability.

7651 Main St, Sherwood

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Washington Fine Properties.

7683 Tilghman Island Rd, Sherwood
$375,000
3 Beds ⋅ 2 Baths
This Sherwood home truly has it all—history, charm, and modern updates. Included is the Historic Sherwood Store, which served the community for more than 160 years. A detached two-bay garage adds even more room for parking, storage, or workshop space. Just around the corner, you’ll also find a public dock and kayak launch on Harris Creek, Where you can moor your boat or jump in for a swim. It also offers easy access to the Choptank River and Chesapeake Bay. This beautiful home welcomes you with a large front porch and features 3 bedrooms and 1.5 baths. One bedroom includes a bonus space ideal for a walk-in closet, nursery, or office. A convenient laundry closet with washer and dryer is included in another bedroom. Upstairs, a full bath showcases a charming stained-glass window, while a half bath downstairs adds everyday convenience. The spacious first floor provides plenty of room to relax or entertain, complete with a cozy gas fireplace in the den. Outside, the peaceful backyard is enclosed with a custom cedar fence and garden arbors, creating a beautiful safe space for children or pets. The side deck is perfect for gatherings or quiet evenings, and the large fenced garden has been a thriving vegetable garden in the past. Lush landscaping and beautiful hydrangeas complete the setting. Thoughtful updates have been done to this historic property, including new roofs on both the house and garage, a new heating/cooling system, a custom kitchen, refinished original flooring, refurbished siding on the accessory building, and fresh interior and exterior paint (approx. 2020). This is a unique opportunity to own a piece of Talbot County’s history in a scenic waterfront community—now at a fantastic value. Note: some pictures are virtual staged

7683 Tilghman Island Rd, Sherwood

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: Benson & Mangold, LLC.

21907 Sherwood Landing Rd, Sherwood
$200,000
3 Beds ⋅ 2 Baths
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 easy access to the best of Eastern Shore living. A small office nook offers a cozy workspace, while a spacious detached garage provides ample storage for boats, bikes, and outdoor gear—perfect for those who love adventure and the water. Whether you're seeking a peaceful weekend getaway or a full-time residence, this rare opportunity combines an unbeatable location, historic charm, and generous storage. Don’t miss your chance to own a piece of Sherwood history.

21907 Sherwood Landing Rd, Sherwood

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: EXP Realty, LLC.

Cabin Cove Rd (, Sherwood
$165,000
We all know that buildable lots are getting harder and harder to find. Consider taking a look at the last lot available in Langdon Farms, with a perc that has been recently updated and is ready to go. Very nice community with established homesites, close to marinas, St. Michaels, Tilghman and the Chesapeake Bay.

Cabin Cove Rd (, Sherwood

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

Holly Woods Rd, Sherwood
$165,000
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.

Holly Woods Rd, Sherwood

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Meredith Fine Properties.

21891 Sherwood Landing Rd, Sherwood
$152,500
2 Beds ⋅ 1 Baths
Nestled in the quaint waterfront village of Sherwood, this charming 2-bedroom, 1-bath cottage offers a wonderful opportunity to enjoy the relaxed lifestyle of Maryland's Eastern Shore. The enclosed front porch with its classic brick floor provides a welcoming entry and flows seamlessly into the living room. The dining room sits conveniently between the living room and kitchen, creating an easy layout for everyday living. The first-floor bedroom enjoys direct access to the sunroom overlooking the backyard, an ideal spot to enjoy your morning coffee, read a book or simply take in the peaceful surroundings. Upstairs, you'll find a spacious second bedroom with two closets, along with a versatile bonus room perfect for a home office, hobby room or walk-in closet. Outside, the backyard offers space to relax and unwind. A gazebo, shed and two small ponds on the property offer the potential to be restored. Just down the street, the public landing provides a kayak launch and long dock, making it easy to get out on the water for boating, crabbing, fishing, kayaking and enjoy all the Chesapeake Bay has to offer. Less than a mile away, Buddy's on the Bay invites you to enjoy waterfront dining, spectacular sunset views, refreshing drinks and live local music. Ideally located, the property is less than 4 miles from Tilghman Island and less than 10 miles from Historic Downtown St. Michaels, offering easy access to boutique shopping, restaurants, marinas, museums and year-round community events. Whether you're looking for a weekend retreat or a year-round residence, this cottage is a wonderful opportunity to experience the charm and beauty of Maryland's Eastern Shore.

21891 Sherwood Landing Rd, Sherwood

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Realty.

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