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Sherwood, Maryland: Country Homes, Houses, and Rural Real Estate

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$6,900,000 128.55 acres 5 Beds | 6 Baths | 10933 sqft
22020 BENDERS LANE, Sherwood, MD 21665 - Talbot County

128.55 acres Sherwood, MD

Bald Eagle Point - One of Talbot County's finest estates, featuring a magnificent 9,000+ sq. ft. home, designed by Alan Meyers, AIA. The 128 acres of land provides absolute privacy & over 1.5 miles of shoreline on Harris Creek & Dun Cove. The views are incredible! Private 1920' grass airstrip (very rare!), equestrian facilities, deep-water dock, 3-BR guest house, subdivision/donation potential.
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$5,225,000 153 acres 9 Beds | 7 Baths
7373 TILGHMAN ISLAND ROAD, Sherwood, MD 21665 - Talbot County

153 acres Sherwood, MD

The legacy of Langdon Farm can only compare to the guests that have graced its halls. It is beloved by all of its owners and all who have been a part of its magnificent history. Every detail of this estate and the grounds exude elegance and style. Four thousand feet of waterfront, with a protected deep water dock for yachting. Endless luxuries at one's disposal.
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$3,900,000 54 acres 5 Beds | 5 Baths
7350 CABIN COVE ROAD SOUTH, Sherwood, MD 21665 - Talbot County

54 acres Sherwood, MD

Elegant living on the Eastern Shore. Exceptional materials and craftsmanship, 54 acre private estate with ornate entrance foyer, gourmet kitchen, 5 ensuite bedrooms with heated bathroom floors, multiple fireplaces, heated pool w/fountains and outdoor kitchen, firepit on the beach with broad ever changing views of the Bay, pier w/boat lifts, 80 x 60 garage.
$3,500,000 50.57 acres 5 Beds | 6 Baths
7350 CABIN COVE RD S, Sherwood, MD 21665 - Talbot County

50.57 acres Sherwood, MD

PRIVATE & SECLUDED WATERFRONT PARADISE! Enjoy 50+Acres & 1,000 FT of Water frontage w/private pier, 2-slips, in-ground pool, patio courtyard ,outdoor kitchen & Rm, & 5 LUX EnSuite BRs inside! Entertain in GRAND style w/BEAUTIFUL Pvt Suites,Chef's Eat-in Kitch w/ Sub-Zero Fridge, Full Sub Zero Freezer & Dbl Prof. SS Appl.SPECTACULAR WATER VIEWS, & SUNSETS! Excellent Vacation Rental History!
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$2,900,000 20.02 acres 3 Beds | 4 Baths | 5028 sqft
7460 CABIN COVE ROAD SOUTH, Sherwood, MD 21665 - Talbot County

20.02 acres Sherwood, MD

Entertain poolside after a brilliant day on the water or explore nearby St. Michaels and Easton. This one level waterfront home sports a deep water private pier in protected Cabin Cove. Interior amenities include granite counters, hardwood floors, exercise room, 4 fireplaces and screened porch. Over 5000 sq ft home on 20+ acres. Submerse yourself in nature's beauty that is the Eastern Shore.
$2,900,000 20.02 acres 3 Beds | 4 Baths | 5028 sqft
7460 Cabin Cove Road South, Sherwood, MD 21665 - Talbot County

20.02 acres Sherwood, MD

Entertain poolside after a brilliant day on the water or explore nearby St. Michaels and Easton. This one level waterfront home sports a deep water private pier in protected Cabin Cove. Interior amenities include granite counters, hardwood floors, exercise room, 4 fireplaces and screened porch. Over 5000 sq ft home on 20+ acres. Submerse yourself in nature's beauty that is the Eastern Shore.
Private Lake
$1,595,000 4.98 acres 4 Beds | 4 Baths
21805 LANGDON FARM RD, Sherwood, MD 21665 - Talbot County

4.98 acres Sherwood, MD

Country setting on deep water Dunns Cove, 4 BR 3 bath cedar clapboard home,quality reproduction of an 18-century house, 2 fireplaces, antique wood floors, detached garage with huge unfinished space above, in ground pool, tree lined drive, Baileys dock w/boatlift ultimate privacy yet a short drive to St Michaels.
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$1,499,000 7.6 acres 4 Beds | 5 Baths
7630 FERRY COVE ROAD, Sherwood, MD 21665 - Talbot County

7.6 acres Sherwood, MD

Sunsets & summer breezes on this 7.6 acre architect designed waterfront home featuring custom state of the art kitchen with formal and casual entertaining spaces. Waterside pool and rip-rapped shore with private beach near marina. This four bedroom home is professionally landscaped and maintained. Totally remodeled in 2014.
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$1,290,000 21.97 acres 3 Beds | 3 Baths
7550 CABIN COVE ROAD, Sherwood, MD 21665 - Talbot County

21.97 acres Sherwood, MD

Absolutely breathtaking & rare expansive point of land with 3000 ft of waterfront on 21 acres! Stunning, gorgeous vistas all around this solid, spacious, bright & newly renovated Daffin built home. 2 fireplaces, garage, pier w/ 3.5 ft mlw. Beach w/ boat ramp, wetlands, coves & plenty of acreage for expansion. Natures paradise! Recent appraisal on file. Must see to believe!
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$785,000 2.16 acres 3 Beds | 3 Baths
21750 DEEP HARBOR FARM RD, Sherwood, MD 21665 - Talbot County

2.16 acres Sherwood, MD

Fabulous waterfront property on 2+ acres close to St Michaels. Brick colonial with 3-car garage features chef's kitchen, custom finishes, hardwood floors throughout, master suite overlooking the water, large bonus room and an office/exercise room on the third floor. Lots of amenities for indoor and outdoor enjoyment; in-ground pool, patio, and dock with boat lift plus kayak launch. Must see!
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$749,000 3.6 acres 3 Beds | 3 Baths
6650 TILGHMAN ISLAND ROAD, Sherwood, MD 21665 - Talbot County

3.6 acres Sherwood, MD

Sunset views abound in this contemporary 3 BDR, 2.5 BTH Back Creek gem built to maximize nature~s beauty! The 2nd floor great room & gourmet kitchen offer endless views & an open floor plan.The home features 3rd floor bonus room, 1st floor bedrooms, 2nd galley kitchen, beautiful landscaping, generator & dock. An oversized 2 car garage w/workshop, studio & 1/2 bath make the perfect artists retreat
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$650,000 6.78 acres 5 Beds | 3 Baths
21584 PUNCH POINT ROAD, Sherwood, MD 21665 - Talbot County

6.78 acres Sherwood, MD

Looking for a tranquil waterfront haven to enjoy nature away from the hustle & bustle of daily life? Look no further! It's 6.78 acres offering 475' of waterfront this home's Geo-Thermal and Solar Systems provide economy & comfort! The possible 1st floor bedroom & full bath offers flexibility for mobility challenged visitors. This quiet, peaceful setting just a short boat ride to the bay!
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$599,000 3.61 acres
7610 FERRY COVE ROAD, Sherwood, MD 21665 - Talbot County

3.61 acres Sherwood, MD

Between St. Michaels and Tilghman Island...Private 3.6 acre waterfront lot w/367' of natural "living shoreline". Facing due west, this beautiful site provides sunset views across Cabin Cove and Chesapeake Bay. Lot is well-elevated and the new FEMA Maps confirm flood insurance is not required on this property (designated low risk "X" Zone). Ag taxes have been paid! A wildlife-lover's paradise!
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$495,000 33.15 acres
DONNELL JONES ROAD, Sherwood, MD 21665 - Talbot County

33.15 acres Sherwood, MD

CHESAPEAKE BAY WATERFRONT ACREAGE - Broad Water Panoramic View Home-site fronting on CHESAPEAKE BAY and Poplar Straights. 30 plus primarily wooded acres with notable wildlife, 10 minutes from St. Michaels; a natural setting ready for your personal mark. Recent ~Residential Feasibility Analysis~ including estimated development costs available to serious-minded Buyer.
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$369,000 2.09 acres 3 Beds | 4 Baths
21845 ALBIE ROAD, Sherwood, MD 21665 - Talbot County

2.09 acres Sherwood, MD

Open & spacious, this attractive Cape features a large living room with vaulted ceilings and gas fireplace; first floor master suite; an office off the kitchen; sheetrocked, unheated space over garage with fixed staircase; and deck with waterviews. Large fenced yard and huge workshop with half bath, second floor storage, and covered storage bay.