Homes with Pools for Sale in 21638, MD

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ABOUT THIS HOME
Home with a Pool for sale in 21638, MD:
Nestled in the woods this home is in the sought after Grasonville community The Woods and is on the market for the first time since being built. Meticulously maintained, featuring a new kitchen, new primary bathroom, in ground & fully fenced pool, gorgeous vaulted ceilings, upstairs second living room loft, and an open floor plan perfect for entertaining. Minutes to 50/301 for the commuter!

$459,900

3 beds2 baths1,662 sq ft

Open floor plan • New kitchen • New primary bathroom

458 Timber Ln, Grasonville, MD 21638

(410) 758-0333

ABOUT THIS HOME
Home with a Pool for sale in 21638, MD:
Classic Colonial Overlooking the Golf Course in Prospect Bay. Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The s

$1,250,000

5 beds3 baths3,757 sq ft

First floor office • Covered awning • Heated swimming pool

4 Prospect Bay Dr W, Grasonville, MD 21638

(410) 263-8686

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in 21638, MD:
Professional Photo's Coming! Priced to sell quickly! Fabulous 2000 sq ft Townhome meticulously maintained by one owner with million dollar PANORAMIC WATER VIEWS down Eastern Bay. This beautiful 3 bedrooms 3.5 baths has views from everywhere! Your home also includes a 40' deep water slip in the North (protected ) Marina. Nice open kitchen , hardwood floors downstairs, and a wood burning fireplace that was barely used. This was a second home used as a quiet summer getaway. There are 2 new sliders and a newer (2023) HVAC! Ask me about the furnishings that could be available. Move right in and enjoy the rest of this summer. Walk / bike to many restaurants and tiki bars around the block.

$725,000

3 beds3.5 baths2,000 sq ft

40 deep water slip • New sliders • Open kitchen

1503 Oyster Cove Dr, Grasonville, MD 21638

(410) 505-9700

ABOUT THIS HOME
Home with a Pool for sale in 21638, MD:
Welcome to this beautiful custom home overlooking the 10th green in Prospect Bay. Set on a one-acre lot, this spacious home offers over 3,000 square feet with 4-5 bedrooms and a comfortable, flexible floor plan. A dramatic two-story foyer welcomes you inside, where tray and vaulted ceilings add character throughout. The bright kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, along with a separate dining room. Open to the kitchen, the family room offers bamboo flooring, a gas fireplace, custom built-ins, and access to the large deck overlooking the backyard and golf course. The spacious primary suite includes a large walk-in closet and private bath with s

$974,000

5 beds2.5 baths3,073 sq ft

Bright kitchen • One acre lot • Sunny morning room

14 Fairway Is, Grasonville, MD 21638

(410) 643-2244

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in 21638, MD:
LOCATION! LOCATION! LOCATION! PANAROMIC WATERFRONT VIEWS!!!! One of the best views in Oyster Cove! Eastern shore's best- kept secret is the beautiful, gated community at the Kent Narrows Bridge! VACATION where you live or work from your home office in this tranquil setting. Scenic entrance ponds with fountains. Grill on your spacious deck while entertaining friends & watch boats heading to St. Michaels/Annapolis, etc. This 3-level, interior townhome was just painted throughout. It offers 3 bedrooms including the loft and 3.5 baths. First floor has white pine floors and a FP w/ electric insert & built-ins. Updated, eat-in country kitchen features granite counters, b

$775,000

3 beds3.5 baths1,470 sq ft

Gated community • Large deck • Waterfront views

1107 Oyster Cove Dr, Grasonville, MD 21638

(443) 496-1367

Property at 116 Prospect Bay Dr W, Grasonville, MD 21638, 4 beds, 2.5 baths

$789,000

4 beds2.5 baths2,425 sq ft

116 Prospect Bay Dr W, Grasonville, MD 21638

(410) 505-9700

Property at 104 Port Ct, Grasonville, MD 21638, 4 beds, 2.5 baths

$1,275,000

4 beds2.5 baths3,069 sq ft

104 Port Ct, Grasonville, MD 21638

(410) 260-2800

Property at 130 Oyster Cove Dr #130, Grasonville, MD 21638, 3 beds, 2 baths

$749,900

3 beds2 baths— sq ft

130 Oyster Cove Dr #130, Grasonville, MD 21638

(410) 643-5005

Property at 24 Fairway Is, Grasonville, MD 21638, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths2,850 sq ft

24 Fairway Is, Grasonville, MD 21638

(410) 643-2244

Property at 801 Chester River Dr, Grasonville, MD 21638, 3 beds, 1 bath

$599,000

3 beds1 bath1,256 sq ft

801 Chester River Dr, Grasonville, MD 21638

(855) 885-4663

Property at 1 Bunker, Grasonville, MD 21638, 4 beds, 3 baths

$724,999

4 beds3 baths2,604 sq ft

1 Bunker, Grasonville, MD 21638

(410) 304-2250

Property at 116 Oyster Cove Dr Unit 1D, Grasonville, MD 21638, 3 beds, 2 baths

$599,000

3 beds2 baths1,651 sq ft

116 Oyster Cove Dr Unit 1D, Grasonville, MD 21638

(443) 274-1900

Property at 108 Prospect Bay Dr W, Grasonville, MD 21638, 4 beds, 2.5 baths

$819,000

4 beds2.5 baths2,552 sq ft

108 Prospect Bay Dr W, Grasonville, MD 21638

(410) 643-2244

Property at 109 Bayview, Grasonville, MD 21638, 3 beds, 3.5 baths

$425,000

3 beds3.5 baths2,044 sq ft

109 Bayview, Grasonville, MD 21638

(410) 224-2200

Property at 114 Bayview, Grasonville, MD 21638, 3 beds, 3.5 baths

$525,000

3 beds3.5 baths2,044 sq ft

114 Bayview, Grasonville, MD 21638

(703) 378-8810

Property at 105 Port Ct, Grasonville, MD 21638, 4 beds, 4.5 baths

$1,325,000

4 beds4.5 baths4,600 sq ft

105 Port Ct, Grasonville, MD 21638

(410) 255-3690

Property at 118 Bayview, Grasonville, MD 21638, 2 beds, 2.5 baths

$579,999

2 beds2.5 baths2,031 sq ft

118 Bayview, Grasonville, MD 21638

(877) 366-2213

Property at 111 Beach Harbor F, Grasonville, MD 21638, 2 beds, 1 bath

$70,000

2 beds1 bath950 sq ft

111 Beach Harbor F, Grasonville, MD 21638

(443) 250-4707

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ABOUT THIS HOME
Home with a Pool for sale in 21638, MD:
TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches and repairs, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware

$549,900

4 beds2.5 baths2,262 sq ft

Full in-law suite • Easy commutes • Waterviews

161 Greenwood Creek Rd, Queenstown, MD 21658

(410) 643-4663

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in 21638, MD:
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass

$4,995,000

5 beds4.5 baths6,156 sq ft

17.97 acre lot • 5 garage spots • Pool

2800 Bennett Point Rd, Queenstown, MD 21658

(410) 673-3344

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in 21638, MD:
Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U. K. , and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has bee

$4,700,000

6 beds5.5 baths8,180 sq ft

2.29 acre lot • 3 garage spots • Pool

200 Wye Rd, Queenstown, MD 21658

(410) 280-5600

Homes with Pools for Sale in 21638

There are currently 18 homes with pools for sale in 21638 at a median listing price of $639K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21638 stay on the market for 77 days and receive 3 offers. This map is refreshed with the newest listings in 21638 every 15 minutes.

In the past month, 11 homes have been sold in 21638. In addition to houses in 21638, there were also 5 condos, 9 townhouses, and 2 multi-family units for sale in 21638 last month. Find your dream home in 21638 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21638 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21638. If you're looking to sell your home in the 21638 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21638 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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