21665, MD homes for sale & real estate

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ABOUT THIS HOME
21665, MD Homes for Sale
Waterfront home situated on Back Creek in Sherwood, offering direct access to the Chesapeake Bay and Choptank Rivers. 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 spac

$1,299,000

3 beds3 baths3,853 sq ft

6670 Tilghman Island Rd, Sherwood, MD 21665

Waterfront home • Gas fireplace • Swimming pool

(410) 745-2596

$4,750,000

5 beds5.5 baths5,554 sq ft

21721 Heavenly Haven Rd, Sherwood, MD 21665

15.54 acre lot • 6 parking spots • Pool

(410) 829-3603

ABOUT THIS HOME
21665, MD Homes for Sale
Escape to Eastern Shore Living! Welcome to this spacious 4-bedroom, 2.5-bath gem nestled in a sought-after water-access community. Enjoy an open-concept layout flooded with natural light, perfect for entertaining or relaxing. The kitchen features stainless steel appliances, while the cozy living room includes a fireplace for year-round comfort and a bedroom on the main level. Three additional bedrooms provide room for guests on the upper level, a home office, or hobbies. Outside, unwind in the private backyard or take a short stroll to the community boat dock for kayaking, boating, crabbing, or serene sunset views. Located minutes from charming shops, local eateries, and everything the East

$585,000

4 beds2.5 baths2,424 sq ft

6705 Tilghman Island Rd, Sherwood, MD 21665

2.05 acre lot • 2 garage spots • Built 1990

(443) 574-1600

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ABOUT THIS HOME
21665, MD Homes for Sale
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; heate

$2,395,000

3 beds3.5 baths3,847 sq ft

21825 Langdon Farm Rd, Sherwood, MD 21665

4.16 acre lot • Garage • Built 2023

(410) 745-2596

ABOUT THIS HOME
21665, MD Homes for Sale
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!

$575,000

3 beds2 baths1,680 sq ft

21869 Albie Rd, Sherwood, MD 21665

2.05 acre lot • Built 2020 • Listed 72 days

(410) 822-6665

Property at 7683 Tilghman Island Rd, Sherwood, MD 21665, 3 beds, 1.5 baths

$400,000

3 beds1.5 baths5,344 sq ft

7683 Tilghman Island Rd, Sherwood, MD 21665

(410) 972-4000

Property at Cabin Cove Road ( Lot 7) Rd, Sherwood, MD 21665

$180,000

— beds— baths— sq ft

Cabin Cove Road ( Lot 7) Rd, Sherwood, MD 21665

(410) 476-2201

Property at Holly Woods Rd, Sherwood, MD 21665

$174,900

— beds— baths— sq ft

Holly Woods Rd, Sherwood, MD 21665

(410) 714-9166

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ABOUT THIS HOME
21665, MD Homes for Sale
ENJOY Stunning SUNSETS and WATER VIEWS!! Tastefully Renovated, this 3 BR, 2 BA home is perfectly situated on 1.09 peaceful Acres overlooking the tranquil Waters of Cummings Creek. Offering true ONE LEVEL living, this turnkey property has been thoughtfully UPDATED from top to bottom in 2025! Step inside to find NEW flooring, fresh paint, stylish trim and all new interior doors with new hardware. The Eat-In Kitchen features NEW Quartz countertops, NEW GE Cafe Stainless Steel Appliances, New stainless sink, NEW White Cabinets and a new reverse osmosis system. Both Bathrooms are fully updated with stylish finishes and the spacious Primary Suite includes a huge walk-in closet! Cozy up by the woo

$499,000

3 beds2 baths1,680 sq ft

22571 Crescendo Cir, Wittman, MD 21676

1.09 acre lot • Garage • Car-dependent

(443) 274-1900

ABOUT THIS HOME
21665, MD Homes for Sale
The Ultimate Harris Creek Retreat—Unrivaled Views. Room to Spread Out. Sunsets You’ll Never Forget. Welcome to your family’s forever getaway: a fully renovated waterfront estate on 2.4 acres with 240+ feet of direct water frontage. Perfectly positioned for stunning western views over Harris Creek, this exceptional property includes a reimagined main residence, newly constructed three-bay garage with guest suite, and a thoughtfully designed pool house for seamless indoor-outdoor living. Enjoy water views from nearly every room. Inside, a welcoming foyer leads to a dramatic great room with panoramic vistas and open flow ideal for entertaining. The sleek kitchen features an o

$2,998,000

5 beds6.5 baths4,711 sq ft

22540 Hardcastle Ln, Bozman, MD 21612

2.41 acre lot • 2 garage spots • Pool

(202) 319-1303

ABOUT THIS HOME
21665, MD Homes for Sale
UNIQUE COTTAGE IN A GREAT VILLAGE SETING WITH A DOCK PROVIDING ACCESS TO BALL CREEK AND QUICK ACCES TO THE CHESAPEAKE WITH GREAT FISHING AND SAILING! Ready for an updating with good bones this would be a wonderful weekender or short term rental. Typical Eastern Shore rural village with great folks it can even be replaced with the home of your dreams. Dock offers a 3 foot channel and has some rip rap with a stable shoreline. Nearly new septic with all of the requirements. Anticipated County sewer system in the works. SUPER LOCATION MINUTES FROM RESTURANTS, SHOPPING, AND THE BAY. SELLER WILL CONSIDER FINANCIG WITH AN ACCEPTABLE CONTRACT AT ATTRACTIVE TERMS

$495,500

2 beds1 bath960 sq ft

6343 Bozman Neavitt Rd, Neavitt, MD 21652

0.26 acre lot • Car-dependent

(410) 822-6665

NEW CONSTRUCTION

ABOUT THIS HOME
21665, MD Homes for Sale
The New Castle is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2 car garage with drop zone entry, attached to a laundry room, that leads through to the Kitchen. The Kitchen has a large amount of space, plenty of cabinets, and a pantry, making storage and organization plentiful and manageable. The well-equipped kitchen is ready for entertaining and with family and friends. The open dining area and long kitchen island offer a plethora of space for informal dining. The kitchen flows effortlessly into the two-story Great Room, which is spacious and is sure to be the center of activity and comfort in the home. The owner's suite is an expansive bedroom with a large walk-in closet a

$499,888

3 beds2 baths1,710 sq ft

5654 Trafalgar Cir, Tilghman, MD 21671

0.23 acre lot • $82 HOA • 2 garage spots

(410) 705-2565

ABOUT THIS HOME
21665, MD Homes for Sale
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 and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leis

$1,200,000

4 beds2.5 baths3,040 sq ft

21477 Island Club Rd, Tilghman, MD 21671

0.58 acre lot • $206 HOA • 2 garage spots

(410) 745-2596

ABOUT THIS HOME
21665, MD Homes for Sale
Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on Maryland's Chesapeake Bay. The backyard pool is a highlight, offering a tranquil setting that is worth the price of admission. Relax poolside after a day spent fishing, crabbing, or sailing. Additionally, a large shed provides ample storage for all your needs. This property also presents a great investment

$399,000

2 beds1 bath864 sq ft

6135 Summit St, Tilghman, MD 21671

0.26 acre lot • Pool • Car-dependent

(410) 714-9166

Property at 21749 Camper Cir, Tilghman, MD 21671, 3 beds, 1 bath

$295,000

3 beds1 bath1,224 sq ft

21749 Camper Cir, Tilghman, MD 21671

(410) 714-9166

Property at 6050 Sunset Ln, Tilghman, MD 21671, 3 beds, 3 baths

$1,275,000

3 beds3 baths3,232 sq ft

6050 Sunset Ln, Tilghman, MD 21671

(410) 829-3603

Property at 5648 Trafalgar Cir, Tilghman, MD 21671, 3 beds, 2 baths

$544,888

3 beds2 baths2,068 sq ft

5648 Trafalgar Cir, Tilghman, MD 21671

(410) 705-2565

Property at 7651 Main St, Sherwood, MD 21665, 2 beds, 2 baths

$425,000

2 beds2 baths1,776 sq ft

7651 Main St, Sherwood, MD 21665

(410) 745-0283

Property at 5520 Leeward Ln, Tilghman, MD 21671, 5 beds, 2.5 baths

$1,200,000

5 beds2.5 baths4,214 sq ft

5520 Leeward Ln, Tilghman, MD 21671

(302) 360-0300

Property at 22860 Middle Point Rd, Neavitt, MD 21652, 3 beds, 2 baths

$1,150,000

3 beds2 baths2,642 sq ft

22860 Middle Point Rd, Neavitt, MD 21652

(410) 745-0415

Property at 6403 Bozman Neavitt Rd, Neavitt, MD 21652, 3 beds, 2 baths

$469,500

3 beds2 baths1,834 sq ft

6403 Bozman Neavitt Rd, Neavitt, MD 21652

(410) 745-2596

Property at 6020 Sunset Ln, Tilghman, MD 21671, 6 beds, 5 baths

$1,745,000

6 beds5 baths4,397 sq ft

6020 Sunset Ln, Tilghman, MD 21671

(410) 673-3344

Property at 22769 Almost Neavitt Rd, Bozman, MD 21612, 4 beds, 2 baths

$859,000

4 beds2 baths1,724 sq ft

22769 Almost Neavitt Rd, Bozman, MD 21612

Property at 5559 Trafalgar Cir, Tilghman, MD 21671, 5 beds, 3.5 baths

$600,000

5 beds3.5 baths3,404 sq ft

5559 Trafalgar Cir, Tilghman, MD 21671

(410) 224-2200

Property at 6394 Bozman Neavitt Rd, Neavitt, MD 21652, 2 beds, 2 baths

$550,000

2 beds2 baths1,570 sq ft

6394 Bozman Neavitt Rd, Neavitt, MD 21652

(410) 745-2596

Property at 5582 Trafalgar Cir, Tilghman, MD 21671, 3 beds, 2.5 baths

$554,999

3 beds2.5 baths2,110 sq ft

5582 Trafalgar Cir, Tilghman, MD 21671

(410) 745-0415

Property at 21472 Willey Rd, Tilghman, MD 21671

$80,000

— beds— baths— sq ft

21472 Willey Rd, Tilghman, MD 21671

(410) 714-9166

Property at Sinclair Ave, Tilghman, MD 21671

$75,000

— beds— baths— sq ft

Sinclair Ave, Tilghman, MD 21671

(410) 714-9166

Average home prices near 21665, MD

Cities

Zip Codes

21665, MD real estate trends

$559K

Sale price

-17.7%
since last year

$253

Sale $/sq ft

-16.3%
since last year

Over list price

Days on market

Down payment

—

Total homes sold

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