Pittsboro Homes with Private Pool

Welcome to Pittsboro, North Carolina – a charming town nestled in the heart of Chatham County, where Southern hospitality meets modern living. Known for its picturesque landscapes and rich history, Pittsboro offers a unique blend of small-town charm and vibrant community life. With its close proximity to the bustling cities of Chapel Hill and Raleigh, residents enjoy the tranquility of rural living while having easy access to urban amenities.

Pittsboro boasts a variety of recreational opportunities, including the scenic Jordan Lake State Recreation Area, perfect for picnicking, hiking, and water activities. The town is also home to a thriving arts scene, with local galleries and studios showcasing the work of talented artists. Farmers' markets, local festivals, and a strong sense of community make Pittsboro an inviting place to call home.

For those seeking a slice of paradise right in their backyard, Pittsboro offers a selection of stunning homes with private pools. Imagine basking in the sun by your own oasis, hosting summer barbecues, or enjoying a peaceful evening swim under the stars. These properties not only provide the luxury of a private pool but also come with spacious yards, perfect for family gatherings or simply enjoying the serene natural surroundings.

Whether you’re a first-time homebuyer or looking to settle down in a peaceful retreat, Pittsboro’s real estate market has something for everyone. Experience the perfect blend of comfort, community, and leisure in this delightful North Carolina town, where your dream home with a private pool awaits!

Newest Pittsboro Homes with Private Pool

$725,000

4 Beds ⋅ 3 Baths ⋅ 10191572 MLS ⋅ ACTIVE Status

Secluded Jordan Lake home, beautifully maintained 1.5-story living on a park-like 3.5 acres with a pool and hot tub. Freshly updated and painted, this exceptional custom-built residence features a gourmet chef's kitchen with a center island, rich hardwood floors, and a stunning stone fireplace that anchors the warm, inviting living space. Enjoy year-round relaxation on the expansive screened porch, the front porch with swing, or meals on the back-dining porch. The spacious primary suite offers direct access to the deck and pool area. With four bedrooms and permits in place for an additional bedroom, the home offers incredible flexibility--including potential for an ADU or multigenerational living. Immaculate condition throughout, with Spectrum fiber, Starlink, and dual-fuel generator. Step outside and experience a true outdoor sanctuary with a fenced vegetable garden and mature perennial irrigated landscaping. Entertain with ease in the resort-style backyard featuring a saltwater inground pool, 8-person hot tub, flagstone patio with fire pit, and a tranquil Koi pond with blooming lotuses. Walk to Jordan Lake on a private trail/easement and enjoy boating, wildlife sightings, hiking trails, and even a nearby bald eagle's nest. Two 24-hour boat/kayak ramps are only 5 minutes away. At the end of a peaceful gravel country road yet located just minutes from downtown Pittsboro and 30 minutes from Chapel Hill and RDU, this one-of-a-kind property offers the perfect blend of tranquil HOA-free rural living with convenient access to dining, shopping, and amenities. Inspection report, repairs/improvements and invoices available.

450 Ryan Rd, Pittsboro

$819,000

4 Beds ⋅ 4 Baths ⋅ 10191393 MLS ⋅ ACTIVE Status

Meticulously maintained 4-bedroom home tucked away in a private wooded setting, encompassed by mature trees, situated on over 2 acres of secluded land. This property offers a perfect blend of convenience, peaceful countryside living, and modern comfort with a dynamic combination of indoor and outdoor living. As you walk through the front door you'll be greeted by an open family room featuring gas fireplace and surround sound speakers with a sitting/reading nook. Newly updated kitchen with new SS appliances, wall oven+microwave, 5-burner gas range with range hood, Corian countertops, custom pantries and cabinets, large breakfast nook, formal dining room, and access to sunroom with HVAC and surround sound speakers. Main level primary suite with vaulted 14' ceilings, gas fireplace, large custom closets, surround sound speakers, custom built-ins, Brazilian cherry hardwood floors, and gorgeous spa bath with huge frameless walk-in-shower, towel heater bar, and dual vanity. Laundry room with cabinets, counters, sink, and powder room completes the main level. Upstairs you'll find a 2nd primary suite with en-suite bath and huge WIC, 2 additional bedrooms and shared full bath with skylights. Walk out basement with large entertainment/rec room featuring surround sound speakers, pool table and bar. Rec room can be converted into 2-car garage. Basement also includes 1 car garage with custom shelving, workshop, exercise/storage room, and newly encapsulated crawlspace. Pool table and fridge in rec room + safe in workshop convey with the home. Incredible outdoor living! Expansive back deck and brick wraparound patio with outdoor grill and composite decking tops, 24 ft diameter 15,000 gallon pool with water slide and zipline, poolside shower with hot and cold water, pool house, and also plumbed for heated pool! 2 more outbuildings on the property, all hooked up with electricity. Charming front porch with swing. Other features include: expansive parking for RV, boats, cars, etc. Private well water with filter and upgraded 1-hp pump. Water iron remover tank in workshop. CPI alarm system. Dimmer lights throughout home. Situated on a high pitch/elevation for flood and rainwater aversion. All natural gas appliances. All additions are permitted. Freshly graveled driveway. New interior paint. Natural gas generator. Invisible fence. Irrigation system. Trail with bridge around the lot for walking or biking. This home is truly a retreat, don't miss your chance, schedule a showing today!

89 Lauren Ct, Pittsboro

$945,000

4 Beds ⋅ 3 Baths ⋅ 10190273 MLS ⋅ ACTIVE Status

Pittsboro Custom Home with Pool & Spa on 2.67 Park-Like Acres Tucked into a wooded backdrop with a true sense of privacy, this home was designed for easy indoor-outdoor living. Step outside to the pool and spa, framed by peaceful, park-like acreage — the kind of setting that makes every afternoon feel like a retreat. Inside, 3,270 heated square feet offer thoughtful craftsmanship and multiple gathering spaces, including a spacious third-floor bonus room ready for movie nights, a home gym, or whatever you need it to be. The heart of the home is the kitchen and great room, seamlessly connected from the large island to the fireplace — made for everyday living and effortless entertaining alike. A guest suite on the main floor offers privacy for visitors, while the remaining bedrooms upstairs create quiet, separate retreats of their own. This is a home that welcomes you in — and welcomes everyone you invite to join you. Directions: A private drive leads to the home, intentionally set back from the road. Turning left onto Silk Hope Gum Spring Rd, the driveway will be on the right.

2946 Silk Hope Gum Springs Rd, Pittsboro

$549,999

3 Beds ⋅ 3 Baths ⋅ 10185428 MLS ⋅ ACTIVE Status

Experience timeless elegance in this immaculate French Provincial-style home, thoughtfully designed and meticulously maintained. Built in 2010, this stunning residence offers three spacious bedrooms, two-and-a-half bathrooms, a generous bonus room, an elegant formal dining room, and a charming breakfast area. The luxurious main-level primary suite provides a private retreat, while beautiful hardwood floors flow throughout the main living spaces. A screened-in porch creates the perfect setting for relaxing or entertaining. Enjoy access to the neighborhood pool and an exceptional location just minutes from historic downtown Pittsboro, dining, shopping, and more.

28 Old Post Ct, Pittsboro

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 10159461 MLS ⋅ ACTIVE Status

The pool is OPEN and this stunner is ready for Summer and outdoor entertaining! A private retreat on over 2 acres tucked away on a cul-de-sac in The Hamptons complete with covered outdoor grilling and dining area, a beautiful pool, outdoor stone fireplace, screened porch and owner's suite and guest bedrooms on the first floor with 2 additional bedrooms upstairs with a bonus. The perfect location that is convenient to Chapel Hill, Durham, Cary, Apex & RDU Int'l. W/D, Refrg, Comm Freezer in garage and garage shelving convey

417 Laurel Knoll Dr, Pittsboro

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Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .