Bishopville Homes with Pool

Bishopville Homes with Pool

Welcome to Bishopville, Maryland – a hidden gem nestled in Worcester County that perfectly marries small-town charm with the beauty of nature. Just a stone's throw away from the bustling beaches of Ocean City, Bishopville offers residents a tranquil escape while still being conveniently close to the vibrant coastal lifestyle. This quaint town is known for its friendly community, lush landscapes, and rich history, making it an ideal place for families, retirees, and anyone looking to enjoy the best of Maryland living.

One of the most appealing features of homes in Bishopville is the abundance of properties with pools. Imagine stepping outside your back door to a serene oasis, where you can unwind under the sun, host summer barbecues, or simply enjoy a refreshing dip after a long day. These homes with pools not only provide a perfect spot for relaxation but also enhance your outdoor living experience, making every day feel like a vacation.

Bishopville is also home to several parks and recreational areas, perfect for outdoor enthusiasts. Whether you enjoy hiking, fishing, or picnicking, the natural beauty surrounding this town is sure to inspire. With a strong sense of community and a variety of local events, residents of Bishopville enjoy a lifestyle that is both vibrant and peaceful.

If you're looking to make a move, consider the charming homes with pools in Bishopville, MD. Here, you can create lasting memories in a picturesque setting that offers both leisure and adventure. Experience the warmth of this delightful town – your dream home awaits!

Newest Bishopville Homes with Pool

$1,035,000
4 Beds ⋅ 3 Baths
Discover exceptional waterfront living in Bayview Estates. Perfectly positioned on a picturesque creek with a private dock and easy access to the bay, this meticulously maintained home offers timeless coastal elegance and an effortless indoor-outdoor lifestyle. The thoughtfully designed floor plan features three bedrooms in the main residence, including a main-level primary suite with a walk-in closet and spa-like bath. A vaulted great room with a wet bar, spacious family room, screened porch, and expansive waterfront decks create the perfect setting for entertaining or relaxing while taking in the breathtaking water views. A detached two-car garage with a finished bonus room provides an ideal fourth bedroom, guest retreat, or private office. An outdoor shower, generous driveway, and beautifully maintained grounds complete this exceptional property. Bayview Estates offers a clubhouse, pool, tennis courts, and a private boat ramp—all with a low $375 annual HOA fee. Experience the finest in coastal waterfront living at 12101 Salt Point Road.

12101 Salt Point Rd, Bishopville

Listing courtesy of Monument Sotheby's International Realty. Contact: 4437087074
$3,599,000
6 Beds ⋅ 8 Baths
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 crow's nest!) is an amazing feature- especially when YOU are up there taking a good look at the 360-degree views of the bay, or fireworks displays, or enjoying your favorite beverage. All rooms in this house feature exquisite hand-crafted architectural elements and views of the natural, coastal habitats. Enter into the main hall and your eyes will be immediately drawn to the direct view of the water. ** Moving forward into the LIVING ROOM, or great hall, is a complete wall of windows soaring 20 feet high. An aged-glass mirror adorns the limestone woodburning fireplace beneath. (mirror included) Most of the floors throughout are walnut, finished on site and stained. (Refinished July 2026!) **The BILLIARD ROOM and adjoining den/MEDIA ROOM showcases brilliant walls of Honduran mahogany. A solid wood pocket door separates the two rooms, if desired. A full wet bar area with granite counters grace the side of the billiard room, including an under counter fridge. Adjoining the billiard room is a side porch with a "cat-slide" roof, adding yet additional character to the overall design. Speaking of design, the Becker-Morgan Group in Salisbury, MD were the architect engineers of this project along with collaboration from both Washington, D.C. And New York City design teams. The **DINING ROOM displays custom wallpaper that was hand painted and depicts the natural elements and scenes from the ponds and surrounding environments. The dining room features a grand bay window, framing magnificent sunsets for guests to admire. **The chef-inspired KITCHEN is appointed with premier Wolf appliances and striking Carrara Italian marble. It features an exquisite copper tile backsplash framing the six-burner gas range and griddle, complemented by an integrated, refined sitting area for elegant entertaining. The floor is limestone from Paris Ceramics. Color is called Irish Blue but shows as black. **A BUTLER'S PANTRY offers granite counters, a 120 bottle wine refrigerator, a copper sink and a beverage refrigerator. The three-story TURRET overlooks the gated 40 X 16 heated swimming pool and hot tub. First floor of the turret is a wonderful and bright SUNROOM, while the second level of the turret is the YOGA ROOM located next to the immense PRIMARY BEDROOM SUITE that features a sprawling "dressing room", or could easily be converted into a nursery. The primary bedroom features a gas fireplace plus an additional adjoining sitting room overlooking the bay and offers access out to the private primary bedroom's balcony. The PRIMARY BATH features marble counters, Thassos 12 X 12 white natural marble floor, quarried in Greece, and the third floor of the turret showcases an office tower/observatory/office. INCREDIBLE architecture and INCREDIBLE views from this 1.47 acre lot! There are SO MANY additional custom features in this spacious home, we've added a special list for you to review upon your request. Although encompassing more than 8,200 square feet, this storybook waterfront residence is gracious in scale but intimate in how it lives. Rarely will you ever find such an enchanted home to call your own. Here's your opportunity to LIVE HAPPILY EVER AFTER. **Current furnishings and décor may differ from those shown in the photographs.

12353 Southhampton Dr, Bishopville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3025372616
$1,199,950
4 Beds ⋅ 5 Baths
Welcome to 12105 Salt Point Road, a newly constructed coastal residence completed in 2024 by Euro Homes. Set within Bay View Estates, this 3,200+ square foot home captures something truly rare: uninterrupted water on two sides and near 360-degree bay views, where virtually every window becomes its own vantage point. The ground level is designed for real life by the water, featuring a spacious living and recreation area, a flexible room ideal as a den, office, or additional bedroom, and a full bath with walk-in shower thoughtfully customized as a dog wash. A generously sized laundry and mudroom adds everyday functionality, while direct access to the insulated two-car garage keeps everything seamless. Upstairs, the home opens in a way that feels both expansive and intentional. Natural light pours into a dramatic two-story family room, where floor-to-ceiling windows, a statement shiplap fireplace, and coffered ceilings stained to match the flooring create a striking focal point. The chef’s kitchen, outfitted with high-end Café appliances, centers the space with an oversized waterfall island designed for gathering. From here, the home flows effortlessly into the dining area, complete with a butler’s counter and pantry, and out through full-view French doors to an expansive deck, where indoor and outdoor living blend seamlessly against a backdrop of water views. An en-suite bedroom with a private bath and direct access to the deck offers a perfect retreat for guests, while a well-appointed half bath and an additional flexible front-facing space provide options for a sitting area, office, or quiet escape. The third level introduces a sense of architectural presence, with a catwalk overlooking the living space below. The primary suite is a true retreat, defined by cathedral ceilings, an expansive walk-in closet, and a spa-like bath, complete with a private balcony overlooking the bay. Two additional bedrooms, including one with its own private balcony, a full bath, and a second laundry area complete the level. Multiple balconies extend the living experience outward, including a private balcony at the stair landing, offering additional vantage points throughout the home. Dual-zone air conditioning ensures comfort across all three levels. Outdoors, a fully fenced yard adds both privacy and peace of mind, creating a secure space ideal for children and pets while maintaining the home’s open coastal feel. The ability to add a private dock creates direct access to boating, kayaking, and paddleboarding. Set within Bay View Estates, just moments from the area’s beaches, dining, and local attractions, the home balances privacy with proximity.

12105 Salt Point Rd, Bishopville

Listing courtesy of Keller Williams Realty. Contact: steve@srarealty.com
$1,795,000
5 Beds ⋅ 6 Baths
11914 Back Creek Road | Bishopville, MD Why buy this instead of waterfront? Waterfront gets you a view — and a long list of trade-offs that come with it: tiny lots, tidal restrictions, flood insurance, no room to expand, and neighbors close enough to hear. This property flips the equation. Nearly 19 private acres, a 6,864 square-foot custom residence, a resort-style pool, and a massive flex/warehouse building most waterfront buyers never even get offered — all just minutes from the water everyone else is paying a premium to sit next to. If what you actually want is space, privacy, and the freedom to use your property exactly how you want, this estate delivers what waterfront, at this price point, simply cannot. The Estate: Set back on nearly 19 acres of cleared and wooded grounds, this 2019-built estate was designed for buyers who want room to breathe — and room to grow. Five bedrooms and six bathrooms are arranged across a thoughtfully laid-out floor plan with soaring ceiling heights and a clean, cohesive architectural style throughout. The kitchen anchors the home with quartz countertops, premium cabinetry, and a substantial island built for real cooking and real entertaining. Living and gathering spaces unfold generously from there, giving the home the kind of scale that's genuinely rare to find this close to the coast. Resort-Style Living, No HOA Required Step outside to a private pool and patio built for entertaining — think fire pit evenings, weekend gatherings, and the kind of outdoor living waterfront lots rarely have the acreage to support. Mature landscaping and privacy fencing keep the grounds secluded, so you get the resort feel without the resort crowd. The Flex/Warehouse Building: The Game-Changer: This is where the property truly separates itself from anything on the water. A massive flex/warehouse building gives you room for a serious workshop, boat and RV storage, a car collection, a home business, or all of the above. It's the kind of infrastructure waterfront zoning almost never allows — and it instantly makes this property useful in ways a bulkhead and a dock never will be. Location: All the Coast, None of the Compromise: Minutes from Ocean City, Berlin, and Assateague Island, this property puts the beach, the boat ramp, the golf course, and the region's best restaurants within easy reach — without asking you to sacrifice acreage, privacy, or flexibility to get there. The Bottom Line: Waterfront buys you a view. This estate buys you nearly 19 acres, a 6,864 square-foot custom home, a resort-style pool, and a warehouse building with more real-world utility than most commercial properties — all minutes from the same beaches, boating, and restaurants waterfront buyers pay a premium for. Space. Privacy. Flexibility. Lifestyle. This is what waterfront, at this price, can't offer.

11914 Back Creek Rd, Bishopville

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$580,000
4 Beds ⋅ 2 Baths
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 here, enjoy boating through Grey’s Creek to Assawoman Bay and waterfront dining destinations, with Ocean City’s inlet approximately 25 minutes away by water. By land, you are just six miles from both Ocean City and Fenwick Island beaches and minutes from Bayside Golf Resort, shopping, and dining. Inside, the welcoming floor plan features a bright breakfast room entry, a spacious eat-in kitchen with abundant cabinetry and prep space, and a sun-filled living room connected by a wide pass-through ideal for entertaining. The main level includes a primary bedroom with hall bath access and an additional guest bedroom. Upstairs, two additional bedrooms with charming dormer details provide flexible living space, along with a large bonus room spanning the length of the garage—perfect for a family room, game room, or home gym—opening to a Juliet balcony overlooking the canal and yard. An oversized two-car garage offers exceptional storage for vehicles, tools, and coastal gear. Being sold as-is, this property presents an excellent opportunity to create your dream waterfront retreat in an unbeatable coastal location, and for added peace of mind the seller is also offering a home warranty.

13374 Cove Landing Rd, Bishopville

Listing courtesy of Northrop Realty. Contact: (302) 539-2900
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