Pittsboro Homes with Outdoor Pool

Welcome to Pittsboro, North Carolina—a charming town nestled in the heart of Chatham County, where Southern hospitality meets natural beauty. Known for its rich history and vibrant community, Pittsboro is a hidden gem that offers a delightful blend of rural charm and modern conveniences. With a population that embraces a close-knit atmosphere, residents enjoy the warm, welcoming spirit that defines this picturesque town.

One of the standout features of Pittsboro is its stunning natural landscapes, perfect for outdoor enthusiasts. The area is dotted with scenic parks, serene lakes, and lush greenery, making it an ideal backdrop for a variety of recreational activities. Whether you enjoy hiking, fishing, or simply soaking in the beauty of nature, Pittsboro has something for everyone.

For those seeking a home that enhances their lifestyle, Pittsboro offers a range of properties with outdoor pools, providing the perfect oasis for relaxation and entertainment. Imagine basking in the sun on warm summer days, hosting lively barbecues, or enjoying a refreshing swim—all from the comfort of your own backyard. These homes not only offer luxurious amenities but also create a space where family and friends can gather and create lasting memories.

With its unique blend of small-town charm and modern living, Pittsboro is more than just a place to live; it’s a community where you can truly thrive. Discover your dream home with an outdoor pool in this enchanting town, and experience the best that North Carolina has to offer. Your oasis awaits in Pittsboro!

Newest Pittsboro Homes with Outdoor 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

$599,900

2 Beds ⋅ 2 Baths ⋅ 10187353 MLS ⋅ ACTIVE Status

Elegance meets everyday comfort in The Carroway, a floor plan designed to make every day feel effortless. At its heart is a glamorous kitchen, anchored by a multi-function island and opening onto sunlit living and dining spaces — perfect for cooking, entertaining, or simply gathering together. The Owner's Retreat offers a true escape, featuring an en suite bathroom and spacious walk-in closet for a private, restorative haven. A well-appointed guest room with its own bathroom ensures visitors enjoy comfort and privacy of their own. Step outside to the covered porch, an inviting extension of the home ideal for quiet evenings or lively gatherings with friends and family.

39 Englehart Ct, 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

$2,999,000

5 Beds ⋅ 6 Baths ⋅ 10176685 MLS ⋅ ACTIVE Status

Luxury, privacy, and timeless elegance come together in this extraordinary custom-built estate on 2 private acres just minutes from Jordan Lake. Designed to impress at every turn, this one-of-a-kind home is filled with natural light from stunning oversized windows that showcase every beautiful space. Offering 5 spacious bedrooms and 5.5 bathrooms, including a luxurious primary suite and private mother-in-law suite on the main level, this home was thoughtfully designed for both everyday living and unforgettable entertaining. The chef's kitchen, complete with a butler's kitchen, flows effortlessly into the open living spaces, while the upstairs loft, oversized bonus room, and private balcony provide endless room to relax, work, or play. Step outside to your own resort-style backyard featuring a sparkling pool, peaceful surroundings, and the privacy you've been searching for. Every detail has been carefully crafted to create a home that feels like a private retreat while keeping you just minutes from Jordan Lake and everyday conveniences. This is more than a place to live. It is the kind of home you'll never outgrow, never want to leave, and never forget.

196 Mountaintop Cir, Pittsboro

$1,285,000

4 Beds ⋅ 4 Baths ⋅ 10161265 MLS ⋅ ACTIVE Status

Exceptional Prewitt-Douglas custom home situated on a quiet cul-de-sac in the prestigious Chapel Ridge community. This 4 bedroom, 3.5 bath residence boasts an open, expansive floor plan designed for effortless entertaining -- both indoors and out. Thoughtfully crafted with generous living spaces and outstanding attention to detail throughout. Residents enjoy access to world-class community amenities including golf, tennis, and a resort-style pool. A rare opportunity to own a distinguished home in one of the area's most coveted neighborhoods -- this one will not last.

64 Mist Wood Ct, Pittsboro

$955,000

4 Beds ⋅ 4 Baths ⋅ 10132755 MLS ⋅ ACTIVE Status

Exceptional custom home in the sought-after Chapel Ridge community. This thoughtfully designed 4 bedroom, 4 bath residence offers an ideal layout with a main-level primary suite and secondary bedroom, perfect for single-level convenience. The open-concept living area flows seamlessly into a beautifully appointed kitchen, creating an inviting space for everyday living and entertaining. Upstairs, two additional bedrooms each feature private en suite baths, while a bonus room and flexible flex space provide endless possibilities for work, play, or relaxation. All of this set within Chapel Ridge -- a premier community offering resort-style amenities just moments from your door. A rare combination of thoughtful design, quality craftsmanship, and an unmatched lifestyle.

191 High Ridge Ln, 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 .