Homes with Pools for Sale in Bishopville, MD

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ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
Nearly 19 private acres, minutes from the water, in a part of Bishopville where land like this almost never comes up. Mature trees screen the property from the road and the neighbors, and that privacy sets the tone before you even reach the front door. A large porch with wood-beamed ceilings and a stone patio gives you a place to sit outside well after dark. Step through the front door into a grand foyer with soaring ceilings, oversized windows, and enough open space for a full seating area of its own, where a glass sliding door straight ahead frames your first look at the pool outside. Crown molding and recessed lighting carry through much of the main level, catching light from windows in

$1,699,000

5 beds5.5 baths6,864 sq ft

11914 Back Creek Rd, Bishopville, MD 21813

18.98 acre lot • 6 garage spots • Pool

(484) 406-3004

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
Now, on to this beautiful home. This is a Custom brick-front contemporary on 1.43 wooded acres in Piney Island, one of Bishopville's most sought-after neighborhoods: a quiet, established community of custom homes on large wooded lots, most of them on the water, tucked well off Route 113 with bay views at the end of the street. Minutes from the Delaware line and about 15 minutes to Ocean City. Roughly 6,300 finished square feet on three levels: 5 bedrooms, 4 full baths, 1 half bath, a main-level primary suite, an oversized 3-car garage, an in-ground pool with automatic pool cover, and something almost nobody on the Lower Shore has, a full finished walk-out basement. The two-story foyer opens

$1,399,900

5 beds4.5 baths6,347 sq ft

10703 Piney Island Dr, Bishopville, MD 21813

In-ground pool • Formal dining room • Two-story foyer

(888) 400-2513

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
ONCE UPON A TIME in a sweeping coastal vista with an architectural world-class design, there is a TIMELESS, premiere Lighthouse Sound estate. Truly an unparalleled level of both privacy and prestige. Fashioned in the classic Shingle-Style design, otherwise known as "Coastal Seaside Architecture". .. MANY EXPENSIVE HOMES ARE LARGE, BUT FEW EXPENSIVE HOMES ARE PROPORTIONED THIS WELL. The symmetry here creates a feeling of both permanence and luxury. The (installed summer 2026) roof is exceptionally interesting with its multiple gables that adds both character and ceiling height inside. Copper accent roofs feature standing seams. The rooftop Widow's Watch, or observation deck, (OR cr

$3,599,000

6 beds7.5 baths8,241 sq ft

12353 Southhampton Dr, Bishopville, MD 21813

Multiple gables • Walnut floors • 20 feet high windows

(302) 537-2616

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
Introducing 13374 Cove Landing Rd. —a canal-front opportunity in the desirable Bayview Estates community, offering private dock access and exceptional coastal potential. While this home carries a Bishopville, MD address, it is located within Bayview Estates and accessed through the Delaware side of the community, offering the convenience of coastal Maryland and Delaware living. Nestled on nearly a half-acre corner lot, this waterfront retreat provides tranquil canal-front living with a private dock. Due to seasonal tides, the dock is best suited for launching smaller craft or short-term tie-ups, while the nearby community boat ramp provides convenient access for larger vessels. From h

$575,000

4 beds2 baths2,340 sq ft

13374 Cove Landing Rd, Bishopville, MD 21813

Community boat ramp • Private dock access • Waterfront retreat

(302) 539-2900

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
Welcome to 10220 Shingle Landing Road, an impressive estate offering over 5,600 square feet of living space on more than 4.5 beautifully landscaped acres. Located in an exclusive setting of just five estate-sized homesites, this exceptional property offers privacy, space, and versatility—all just a few miles from the beaches of Ocean City. This expansive home features 6 bedrooms and 5.5 bathrooms, along with an attached 3-car garage and a separate 3-car detached garage. The detached garage includes a spacious second floor offering tremendous potential for a game room, home office, studio, recreation space, or other future use. The outdoor living area is truly a highlight, featuring a

$1,495,000

6 beds5.5 baths5,649 sq ft

10220 Shingle Landing Rd, Bishopville, MD 21813

Hot tub hookup • Irrigation system • In ground pool

(410) 535-6291

Property at 12105 Salt Point Rd, Bishopville, MD 21813, 4 beds, 4.5 baths

$1,149,950

4 beds4.5 baths3,290 sq ft

12105 Salt Point Rd, Bishopville, MD 21813

(302) 360-0300

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ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
Welcome to 75 Cresthaven Drive, a charming A-frame home located in the desirable Ocean Pines community! This unique 3-bedroom, 2-bath home offers 1,128 square feet of living space and sits on a spacious 10,700-square-foot lot. Whether you're searching for a beach getaway, full-time residence, or investment property, this home offers plenty of possibilities. Currently generating approximately $35,000–$38,000 in annual rental income, it provides an excellent opportunity for buyers looking for a proven vacation rental. The distinctive A-frame design gives the home plenty of coastal character, while the large front deck provides the perfect place to relax and enjoy the outdoors. Out back,

$415,000

3 beds2 baths1,296 sq ft

75 Cresthaven Dr, Ocean Pines, MD 21811

Entertainment area • Fire pit • Large front deck

(410) 535-6291

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
This is the location in The Parke you've been waiting for, tucked away for serene privacy on a large 12,858 square foot, cul-de-sac lot backing to woods! This Royal Tern floor plan offers 2,587 sq. ft. of comfortable living space, 3 bedrooms/2 full baths downstairs, and an additional 4th bedroom and full bath upstairs with loft area. The main level features a spacious living room with cathedral ceiling, ceiling fan and a “sun tunnel” style skylight lets in extra natural light. A double-sided gas fireplace with blower creates a warm connection to the adjoining spaces. The kitchen offers numerous upgrades just completed in 2025—including a JennAir gas cooktop, new quartz cou

$549,900

4 beds3 baths2,587 sq ft

7 Brush Island Ct, Ocean Pines, MD 21811

Cul-de-sac lot • Custom cabinetry • Quartz countertops

(410) 524-6400

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
Coastal Luxury, Bay Views & Proven Rental Potential in Midtown Ocean City Welcome to 109 70th Street, a beautifully maintained, fully furnished coastal retreat in Broad Marsh, one of Midtown Ocean City’s desirable bayfront communities. This spacious three-level, 4-bedroom, 3.5-bath townhome offers an exceptional combination of coastal living, beautiful bay views, community amenities, and proven short-term rental potential. Currently operated as a successful vacation rental generating approximately $55,000 in annual rental revenue, this property offers an established rental history and an exciting opportunity for buyers seeking both a personal beach retreat and an income-producin

$830,000

4 beds3.5 baths2,000 sq ft

109 70th St Unit D, Ocean City, MD 21842

Custom backsplash • Upgraded countertops • Bay views

(833) 335-7433

NEW 18 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
Discover an exceptional investment opportunity in the heart of the Carousel Condominiums, where luxury meets coastal living. This stunning 2-bedroom, 2-bathroom unit boasts an open floor plan, accentuated by crown moldings and elegant ceramic tile and luxury vinyl plank flooring. The spacious kitchen features a central island, perfect for entertaining, while the combination dining and living area invites relaxation with ocean views that inspire tranquility. Enjoy the convenience of in-unit laundry facilities and stainless-steel appliances, including a dishwasher, electric oven/range, and refrigerator, ensuring a seamless living experience. The property is furnished, allowing for immediate r

$555,555

2 beds2 baths912 sq ft

11700 Coastal Hwy #1109, Ocean City, MD 21842

Fitness center • Heated indoor pool • Tennis courts

(443) 632-3000

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
Welcome to The Parke in Ocean Pines! This wonderful 4 bedroom, 3 full bath home has been tastefully renovated with a new dual-zone heat pump system, new gas water heater, new carpet in bedrooms, new LVP, new paint throughout house and garage, new bathroom fixtures, new kitchen appliances, new ceiling fans and other finishing touches to provide a move-in-ready experience. Property highlights include a double-sided gas fireplace between the living room and sunroom, cathedral ceiling in the living room, kitchen and breakfast area and a large loft overlooking the living area and a large primary bedroom/bathroom on the 1st level. All of this on a 0.23 +/- acre parcel adjacent to a peaceful wood

$564,900

4 beds3 baths2,587 sq ft

1 Freeport Ln, Berlin, MD 21811

Large loft • Peaceful wooded area • Cathedral ceiling

(855) 687-2765

ABOUT THIS HOME
Home with a Pool for sale in Bishopville, MD:
This property offers a front row seat to resort style luxury every day with breathtaking, panoramic views of the nicely manicured golf course and shimmering ponds. Large windows perfectly frame this picturesque backdrop, offering a feeling of vast space and privacy. Enjoy your morning coffee or evening cocktails on the deck, while watching the sun shine on the peaceful waters in your own backyard oasis. The entire interior has been tastefully remodeled to include luxury vinyl plank flooring, tub showers, built-in shelving, stainless steel appliances, upgraded countertops, up-to-date ceiling fan, ship lap and bead-board walls, all while maintaining the original aesthetics such as wooden beam

$339,900

3 beds2 baths1,418 sq ft

438 Ocean Pkwy #18, Ocean Pines, MD 21811

Backyard oasis • Panoramic views • Built-in shelving

(410) 208-9200

Property at 13214 Peachtree Rd, Ocean City, MD 21842, 3 beds, 2 baths

$549,000

3 beds2 baths1,356 sq ft

13214 Peachtree Rd, Ocean City, MD 21842

(410) 250-3020

Property at 204 S Heron Dr Unit 202 G, Ocean City, MD 21842, 2 beds, 2 baths

$499,900

2 beds2 baths1,125 sq ft

204 S Heron Dr Unit 202 G, Ocean City, MD 21842

(443) 856-2211

Property at 6803 Atlantic Ave Unit 4H, Ocean City, MD 21842, 1 bed, 1 bath

$425,000

1 bed1 bath756 sq ft

6803 Atlantic Ave Unit 4H, Ocean City, MD 21842

(443) 856-2211

Property at 80 Cresthaven Dr, Ocean Pines, MD 21811, 1 bed, 1 bath

$409,000

1 bed1 bath1,326 sq ft

80 Cresthaven Dr, Ocean Pines, MD 21811

(302) 539-9040

Property at 721-C Bradley Rd Unit 2C, Ocean City, MD 21842, 2 beds, 2 baths

$379,000

2 beds2 baths858 sq ft

721-C Bradley Rd Unit 2C, Ocean City, MD 21842

(410) 524-7000

Property at 13100 Coastal Hwy #110602, Ocean City, MD 21842, 2 beds, 2 baths

$465,000

2 beds2 baths1,015 sq ft

13100 Coastal Hwy #110602, Ocean City, MD 21842

(410) 543-4545

Property at 192 Timberline Cir, Berlin, MD 21811, 2 beds, 1 bath

$259,000

2 beds1 bath748 sq ft

192 Timberline Cir, Berlin, MD 21811

(302) 539-9040

Property at 4601-B Coastal Hwy #403, Ocean City, MD 21842, 3 beds, 3.5 baths

$674,990

3 beds3.5 baths1,830 sq ft

4601-B Coastal Hwy #403, Ocean City, MD 21842

(888) 860-7369

Property at 13110 Coastal Hwy #41201, Ocean City, MD 21842, 2 beds, 2 baths

$529,900

2 beds2 baths908 sq ft

13110 Coastal Hwy #41201, Ocean City, MD 21842

(410) 524-0919

Property at Undisclosed address, Ocean City, MD 21842, 2 beds, 2 baths

$12,500

2 beds2 baths1,104 sq ft

Undisclosed address, Ocean City, MD 21842

(443) 552-7579

Property at 111 Jamestown Rd Unit B4, Ocean City, MD 21842, 3 beds, 2 baths

$399,999

3 beds2 baths912 sq ft

111 Jamestown Rd Unit B4, Ocean City, MD 21842

(302) 360-0300

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

$619,000

3 beds2 baths2,198 sq ft

10 Mist Flower Rd, Ocean Pines, MD 21811

(888) 400-2513

Property at 39144 New Providence Ln, Fenwick Island, DE 19944, 4 beds, 3.5 baths

$1,299,000

4 beds3.5 baths2,400 sq ft

39144 New Providence Ln, Fenwick Island, DE 19944

Property at 101 123rd St Unit 228C3, Ocean City, MD 21842, 1 bed, 1 bath

$238,000

1 bed1 bath585 sq ft

101 123rd St Unit 228C3, Ocean City, MD 21842

Homes with Pools for Sale in Bishopville

There are currently 6 homes with pools for sale in Bishopville at a median listing price of $496K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Bishopville stay on the market for 58 days. This map is refreshed with the newest listings in Bishopville every 15 minutes.

In the past month, 1 home has been sold in Bishopville. Find your dream home in Bishopville 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 Bishopville are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Bishopville. Our Bishopville real estate stats and trends will give you more information about home buying and selling trends in Bishopville. If you're looking to sell your home in the Bishopville area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Bishopville with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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