Homes with Pools for Sale in 21811, MD

180 homes

Sort:

Recommended

NEW 17 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in 21811, MD:
Welcome to this gorgeous, turnkey home in the amenity-rich community of Ocean Pines! Beautifully updated and thoughtfully maintained, this home offers a warm and inviting layout with stylish upgrades throughout. The spacious enclosed porch provides the perfect spot to relax and enjoy the surrounding scenery, while the brick steps and paved driveway add great curb appeal. Inside, you’ll find charming, exposed wood beams, a cozy fireplace, and beautiful finishes that make this home truly move-in ready. The two-car garage offers plenty of space for parking and storage. Out back, enjoy your own private retreat with a gazebo—perfect for entertaining or relaxing outdoors. Conveniently

$449,900

3 beds2.5 baths1,851 sq ft

7,700 sq ft lot • 2 garage spots • Community pool

50 Windjammer Rd, Ocean Pines, MD 21811

(443) 552-7579

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in 21811, MD:
Welcome to this gorgeous 5-bedroom, 3-full-bath single-family home offering over 3,000 square feet of beautifully designed one-level living, ideally situated on a quiet cul-de-sac in the heart of Ocean Pines! The spacious open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating the perfect space for relaxing with family in front of the cozy gas fireplace. The home also offers two separate study/office rooms, each featuring built-in bookcases and French doors, providing quiet and private spaces for working from home, studying, or hobbies. A dedicated game/movie room takes entertaining to the next level with a large-screen TV, custom bar area, and wall outle

$499,900

5 beds3 baths3,030 sq ft

0.35 acre lot • Garage • Community pool

30 Sloop Ln, Ocean Pines, MD 21811

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in 21811, MD:
Welcome to an exceptional waterfront retreat in the prestigious community of Bay Point Plantation, where refined coastal living, beautiful water views, and effortless access to the bay come together. This beautifully appointed 5-bedroom, 3.5-bath, three-story residence includes coveted Boat Slip #20, offering an incredible opportunity to embrace the waterfront lifestyle. From the moment you arrive, the home impresses with an oversized, finished two-car garage and a private backyard designed for relaxation and entertaining. Your own outdoor oasis features a swimming pool, spa, spacious patio, and fenced yard, creating an inviting setting for summer afternoons, evening gatherings, and weekend

$1,975,000

5 beds3.5 baths3,130 sq ft

Fenced yard • Private backyard • Spa

10312 Plantation Ln, Berlin, MD 21811

(410) 524-6400

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in 21811, MD:
Experience elevated, expansive waterfront living at this 3,300+ sq. ft. residence, perfectly positioned to capture panoramic, unobstructed views, and direct access to the Isle of Wight Bay. This 3-bedroom, 3.5-bath home offers a thoughtfully designed layout complemented by a whole-home audio system throughout. The second floor serves as the main living level, where soaring vaulted ceilings and an open-concept kitchen with an oversized island and gas range create an ideal space for entertaining—all framed by sweeping, elevated water views. This level also features a versatile office/flex space, allowing you to work or create while overlooking the water, alongside a spacious owner&rsquo

$819,900

3 beds3.5 baths3,342 sq ft

Private dock • Expansive waterfront • 0.35 acre lot

86 Boston Dr, Ocean Pines, MD 21811

(410) 524-6400

ABOUT THIS HOME
Home with a Pool for sale in 21811, MD:
Seller and family have work to remove their personal items collected over their many years of ownership and enjoyment. Some minor handyman work was done, and it is now ready to see and fall in love with. This is a Duane Maddy, Piney Island Builders, classic contemporary with all your "I wants". Formal Living room greets you as you enter and that leads to the large Family Room, kitchen and dining area. 12x12 screened porch and 20x12 deck for outdoor enjoyment. New roof in 2022 and Encapsulated Crawl space in 2017. In 2014, new kitchen granite countertops and all new appliances. An additional room was added that could be a Bunk Room or Office. Sold furnished with Inventory List avai

$525,000

3 beds3 baths1,948 sq ft

Large deck • Large family room • Screened porch

62 Martinique Cir, Ocean Pines, MD 21811

(410) 208-3500

Property at 60 Drawbridge Rd, Ocean Pines, MD 21811, 2 beds, 2.5 baths

$459,990

2 beds2.5 baths2,304 sq ft

60 Drawbridge Rd, Ocean Pines, MD 21811

(410) 543-4545

Property at 72 Newport Dr, Ocean Pines, MD 21811, 3 beds, 2 baths

$499,900

3 beds2 baths1,506 sq ft

72 Newport Dr, Ocean Pines, MD 21811

(302) 539-1777

Property at 202 Ocean Pkwy, Berlin, MD 21811, 3 beds, 1 bath

$310,000

3 beds1 bath1,080 sq ft

202 Ocean Pkwy, Berlin, MD 21811

(443) 992-4990

Property at 12418 Coastal Marsh Dr, Berlin, MD 21811, 4 beds, 2.5 baths

$657,500

4 beds2.5 baths3,722 sq ft

12418 Coastal Marsh Dr, Berlin, MD 21811

(443) 856-2211

Property at 7 Fishermans Dr, Berlin, MD 21811, 3 beds, 2 baths

$349,000

3 beds2 baths1,404 sq ft

7 Fishermans Dr, Berlin, MD 21811

(443) 552-7579

Property at 9828 Ocean Life Ln, Ocean City, MD 21842, 2 beds, 2 baths

$279,900

2 beds2 baths1,184 sq ft

9828 Ocean Life Ln, Ocean City, MD 21842

(443) 552-7579

Property at 1150 Ocean Pkwy, Ocean Pines, MD 21811, 4 beds, 3.5 baths

$724,900

4 beds3.5 baths2,200 sq ft

1150 Ocean Pkwy, Ocean Pines, MD 21811

(410) 524-6400

Property at 38 Battersea Rd, Ocean Pines, MD 21811, 4 beds, 3 baths

$899,900

4 beds3 baths3,896 sq ft

38 Battersea Rd, Ocean Pines, MD 21811

(410) 524-6400

Property at 1 Columbia Ave, Ocean Pines, MD 21811, 3 beds, 3 baths

$519,900

3 beds3 baths2,125 sq ft

1 Columbia Ave, Ocean Pines, MD 21811

(410) 208-3500

Property at 12394 Sea Oaks Ln, Berlin, MD 21811, 4 beds, 4 baths

$539,000

4 beds4 baths2,664 sq ft

12394 Sea Oaks Ln, Berlin, MD 21811

(443) 274-1900

Property at 152 Intrepid Ln #89, Berlin, MD 21811, 3 beds, 2.5 baths

$349,900

3 beds2.5 baths1,770 sq ft

152 Intrepid Ln #89, Berlin, MD 21811

(443) 552-7579

Property at 12452 Sea Oaks Ln #4, Berlin, MD 21811, 5 beds, 4.5 baths

$599,000

5 beds4.5 baths3,020 sq ft

12452 Sea Oaks Ln #4, Berlin, MD 21811

(443) 552-7579

Property at 386 Ocean Pkwy, Ocean Pines, MD 21811, 3 beds, 3 baths

$579,990

3 beds3 baths1,566 sq ft

386 Ocean Pkwy, Ocean Pines, MD 21811

(888) 860-7369

Property at 3 Links Ln, Berlin, MD 21811, 4 beds, 3 baths

$515,000

4 beds3 baths2,338 sq ft

3 Links Ln, Berlin, MD 21811

(302) 539-9040

Property at 84 Newport Dr, Ocean Pines, MD 21811, 3 beds, 3 baths

$875,000

3 beds3 baths2,501 sq ft

84 Newport Dr, Ocean Pines, MD 21811

(410) 524-6400

Property at 43 Birdnest Dr, Ocean Pines, MD 21811, 3 beds, 2 baths

$369,900

3 beds2 baths1,160 sq ft

43 Birdnest Dr, Ocean Pines, MD 21811

(410) 208-9200

Property at 3 Starboard Ct, Ocean Pines, MD 21811, 3 beds, 2 baths

$399,999

3 beds2 baths1,738 sq ft

3 Starboard Ct, Ocean Pines, MD 21811

(410) 213-7040

Property at 11 Seafarer Ln, Ocean Pines, MD 21811, 3 beds, 2 baths

$474,900

3 beds2 baths1,539 sq ft

11 Seafarer Ln, Ocean Pines, MD 21811

(302) 360-0300

Property at 180 Teal Cir, Ocean Pines, MD 21811, 3 beds, 3 baths

$499,900

3 beds3 baths1,638 sq ft

180 Teal Cir, Ocean Pines, MD 21811

(443) 856-2211

Property at 12903 Windy Dr, Ocean City, MD 21842, 6 beds, 4.5 baths

$9,500,000

6 beds4.5 baths8,638 sq ft

12903 Windy Dr, Ocean City, MD 21842

(410) 524-7700

Property at 1218 Ocean Pkwy, Ocean Pines, MD 21811, 3 beds, 2 baths

$364,900

3 beds2 baths1,284 sq ft

1218 Ocean Pkwy, Ocean Pines, MD 21811

(443) 552-7579

Property at 542 Ocean Pkwy, Ocean Pines, MD 21811, 4 beds, 2 baths

$499,000

4 beds2 baths2,520 sq ft

542 Ocean Pkwy, Ocean Pines, MD 21811

(302) 539-1777

Property at 7 Royal Oaks Dr, Ocean Pines, MD 21811, 3 beds, 2.5 baths

$364,900

3 beds2.5 baths1,440 sq ft

7 Royal Oaks Dr, Ocean Pines, MD 21811

(410) 543-4545

Property at 8220 Skipjack Dr, Berlin, MD 21811, 2 beds, 1 bath

$269,900

2 beds1 bath748 sq ft

8220 Skipjack Dr, Berlin, MD 21811

(410) 641-1671

Property at 10 Stonemeadow Ct, Ocean Pines, MD 21811, 3 beds, 2 baths

$389,000

3 beds2 baths1,112 sq ft

10 Stonemeadow Ct, Ocean Pines, MD 21811

(410) 208-3500

Property at 582 Ocean Pkwy, Ocean Pines, MD 21811, 3 beds, 2.5 baths

$499,000

3 beds2.5 baths1,392 sq ft

582 Ocean Pkwy, Ocean Pines, MD 21811

(410) 520-2600

Property at 125 Skipjack Cir, Berlin, MD 21811, 2 beds, 1 bath

$224,900

2 beds1 bath748 sq ft

125 Skipjack Cir, Berlin, MD 21811

(410) 524-6400

Property at 2 Heron Isle Ct, Ocean Pines, MD 21811, 3 beds, 2 baths

$325,000

3 beds2 baths1,571 sq ft

2 Heron Isle Ct, Ocean Pines, MD 21811

(410) 524-1700

Property at 6 Briarcrest Dr, Ocean Pines, MD 21811, 2 beds, 2 baths

$399,000

2 beds2 baths1,380 sq ft

6 Briarcrest Dr, Ocean Pines, MD 21811

(410) 208-3500

Property at 23 Mallard Dr E, Ocean Pines, MD 21811, 5 beds, 5.5 baths

$2,790,000

5 beds5.5 baths9,200 sq ft

23 Mallard Dr E, Ocean Pines, MD 21811

(410) 524-0919

Property at 10001 Flotilla Ln, Berlin, MD 21811, 3 beds, 2.5 baths

$899,000

3 beds2.5 baths3,378 sq ft

10001 Flotilla Ln, Berlin, MD 21811

(410) 208-3500

Property at 10 Gloucester Rd, Ocean Pines, MD 21811, 3 beds, 2 baths

$375,000

3 beds2 baths1,456 sq ft

10 Gloucester Rd, Ocean Pines, MD 21811

(443) 856-2211

Property at 6 Weeping Willow Ct, Ocean Pines, MD 21811, 3 beds, 2 baths

$385,000

3 beds2 baths1,248 sq ft

6 Weeping Willow Ct, Ocean Pines, MD 21811

(410) 208-3500

Property at 3208 Points Reach #3208, Ocean Pines, MD 21811, 3 beds, 2 baths

$514,900

3 beds2 baths1,896 sq ft

3208 Points Reach #3208, Ocean Pines, MD 21811

(410) 486-4504

Property at 953 Yacht Club Dr, Ocean Pines, MD 21811, 3 beds, 2.5 baths

$479,900

3 beds2.5 baths1,784 sq ft

953 Yacht Club Dr, Ocean Pines, MD 21811

(443) 856-2211

Property at 42 Quarter Staff Pl, Ocean Pines, MD 21811, 3 beds, 2 baths

$425,000

3 beds2 baths1,252 sq ft

42 Quarter Staff Pl, Ocean Pines, MD 21811

(410) 524-6400

Viewing page 1 of 5

Homes with Pools for Sale in 21811

There are currently 180 homes with pools for sale in 21811 at a median listing price of $489K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21811 stay on the market for 74 days and receive 1 offers. This map is refreshed with the newest listings in 21811 every 15 minutes.

In the past month, 50 homes have been sold in 21811. In addition to houses in 21811, there were also 11 condos, 61 townhouses, and 1 multi-family unit for sale in 21811 last month. Find your dream home in 21811 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 21811 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21811. If you're looking to sell your home in the 21811 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21811 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for 21811, MD

Nearby Zip Codes

Cities

Nearby Zip Codes with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in 21811, MD

How to buy a house in 21811, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Buy the right home at the right price near 21811 with a local Redfin real estate agent.

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.