Pittsboro Homes with Outdoor Pool

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

196 Paces Mill Trl, Pittsboro
$2,900,000
3 Beds ⋅ 3 Baths ⋅ 10197637 MLS ⋅ ACTIVE Status
A Majestic Haven on the Haw. Welcome to an extraordinary riverside sanctuary less than 20 minutes from the heart of Chapel Hill and the University of North Carolina. This gated almost 22-acre estate, gracing the banks of the majestic Haw River, seamlessly blends luxury living with natural splendor. The property features nearly a mile of private riverside trails, perfect for hiking or accessing the river for canoeing, kayaking, and fishing--with abundant bass, carp, crappie, sunfish, and bluegill. This enchanting refuge teems with wildlife. Deer regularly graze the grounds, while otters and beavers make their home along the riverbank. Bird enthusiasts will marvel at the diverse avian population, including majestic bald eagles, great blue herons, ospreys, warblers, and kingfishers. You may never see such beautiful sunsets as you do right at the comfort of your own home. Your home is comparable to this natural environment's beauty. Built in 2020 and designed by acclaimed architect Arielle Schechter--recognized among Forbes Magazine's 200 Best Residential Architects of 2025--this contemporary masterpiece showcases sophisticated design that harmonizes with its stunning setting. Breathtaking views of what many consider the river's most picturesque section are displayed through expansive windows, seemingly dissolving the boundary between indoors and out. Environmental consciousness meets luxury in this near net-zero residence, featuring: * Rooftop solar array * Geothermal heating and cooling * Triple-glazed European passive house windows and doors * Advanced water catchment system with dual 5,000-gallon cisterns * Solar reflective shades The property's resort-like amenities include: * Infinity pool with spa * Sauna * Steam shower * Separate workshop building with exercise room and upstairs bonus room * Private yurt with fenced yard. This secluded residential resort offers an unparalleled living experience that must be seen to be truly appreciated.

196 Paces Mill Trl, Pittsboro
196 Mountaintop Cir, Pittsboro
$2,999,999
5 Beds ⋅ 6 Baths ⋅ 10193908 MLS ⋅ ACTIVE Status
Coming Soon! This 5-bedroom, 5.5-bathroom residence in The Summit offers substantial living space with nearly two acres of Land with mature Hardwood trees and a beautiful stream at the backside of the property. Your own private pool and surrounding patio areas create a most private estate. The four-car garage provides ample parking and storage for the discerning homeowner. Located near Apex, Chapel Hill and Pittsboro, this ultra-luxury home delivers the room and privacy many buyers seek when building lasting equity. The generous lot size creates a meaningful buffer from surrounding properties, while the multiple bedrooms and baths accommodate varied household needs and guest accommodations.

196 Mountaintop Cir, Pittsboro
417 Laurel Knoll Dr, Pittsboro
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 10193509 MLS ⋅ ACTIVE Status
Set on more than two private acres, this Pittsboro home feels like a retreat of its own while still being just minutes from Fearrington Village and downtown Pittsboro, and less than 20 minutes from Chapel Hill. Mature landscaping, a fully fenced backyard, and a peaceful setting create the kind of privacy that is increasingly hard to find. Step inside to a spacious foyer and dramatic two story living room, where abundant windows fill the home with natural light. The updated kitchen sits at the heart of the home, with a spacious dining room just off the kitchen offering plenty of room to gather and beautiful natural light. Thoughtfully selected designer lighting adds a custom feel throughout the home. With more than 3,700 total square feet, there is plenty of room to come together and space to spread out. The first floor primary suite offers the convenience of main level living, complete with a beautifully renovated primary bath and built in sound system. A second bedroom on the main floor is perfect for guests or can easily serve as a private home office. Upstairs, two additional bedrooms share a Jack and Jill bath, while the large bonus room offers even more flexibility for a media room, playroom, home office, or hangout space. Outside is where this home really shines. Start your morning with coffee on the screened porch, enjoy an extended pool season thanks to the heated saltwater pool, and end the day gathered around the outdoor fireplace or covered outdoor kitchen and bar. Surrounded by mature landscaping and more than two acres, the backyard feels like your own private escape with plenty of room to entertain, unwind, and simply enjoy the peace and quiet. Private without feeling remote, this is the kind of home that gives you room to breathe while keeping Fearrington Village, downtown Pittsboro, Chapel Hill, dining, shopping, and everyday conveniences within easy reach.

417 Laurel Knoll Dr, Pittsboro
450 Ryan Rd, Pittsboro
$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
89 Lauren Ct, 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
2946 Silk Hope Gum Springs Rd, 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
28 Old Post Ct, Pittsboro
$549,999
3 Beds ⋅ 3 Baths ⋅ 10185428 MLS ⋅ ACTIVE Status
Experience the charm and sophistication of this impeccably maintained French Provincial-style home, thoughtfully designed for both everyday comfort and elegant entertaining. Built in 2010, this stunning residence features 3 bedrooms, 2.5 bathrooms, a spacious bonus room. The luxurious main-level primary suite offers a private retreat, while beautiful hardwood floors enhance the main living spaces with warmth and character. Upstairs, you'll find two additional bedrooms, a full bath, walk-in attic spaces for storage and a versatile bonus room that can easily serve as a home office, media room, guest space, or hobby area. Relax and unwind on the inviting screened porch, perfect for enjoying your morning coffee or gathering with family and friends. Recent updates provide peace of mind, including a new lower HVAC system (2022), gas water heater (2026), epoxy-coated garage floor (2021), with electric garage heater for supplemental heat. Situated in a welcoming community with a pool, clubhouse, and pond, this home offers the perfect balance of neighborhood amenities and small-town charm. Enjoy being just minutes from historic downtown Pittsboro, where you'll find local dining, shopping, community events, and more. Convenient access to US 15/501, NC 87, and US 64 makes travel throughout Chatham County and the Triangle area easy. If you are seeking the convenience of first-floor living, thoughtful updates, and an exceptional Pittsboro location, 28 Old Post Court is a home you won't want to miss.

28 Old Post Ct, Pittsboro
213 Westhampton Dr, Pittsboro
$3,295,000
5 Beds ⋅ 6 Baths ⋅ 2542676 MLS ⋅ ACTIVE Status
Introducing Stella our Show Home is now for sale! - A Modern Ultra-Luxury Masterpiece in The Summit Stella is now complete and ready to impress in the prestigious Summit community. Thoughtfully positioned on one of the smoothest and most desirable home sites, this striking modern architectural design seamlessly blends sophisticated indoor living with resort-style outdoor amenities. Expansive patios, Sonos sound system, a beautifully designed optional saltwater pool, and multiple outdoor entertaining areas provide an exceptional lifestyle experience. The home's exterior is distinguished by authentic Rockford Estate stone, perfectly paired with warm natural textures and clean lines. Slatted natural oak acoustic panels accentuate the sleek linear fireplace inside, while Pennsylvania bluestone graces the rear deck--setting a serene tone around the covered porch and its cozy fireplace. Stella welcomes you with a grand entrance: a flagstone stoop and double 42'' x 8' tall aged-bronze steel front doors with electrified privacy glass. Step inside to a voluminous foyer that flows effortlessly into a dramatic great room and an ultra-luxurious Wolf/Sub-Zero chef's kitchen, complete with a fully equipped walk-in scullery. The main level is intelligently designed with two spacious bedrooms, a private den, a convenient laundry room, and a lavish primary suite featuring heated floors in the spa-like bathroom. Enjoy year-round outdoor living in the massive Phantom-screened porch that merges comfort with functionality. The upper level offers three additional bedrooms, a generous recreation room, a dedicated fitness center, a second laundry room, and an expansive walk-in storage space--ideal for long-term organization. Additional highlights include: A three-car smart garage with EV charging station Professionally designed, fully irrigated landscape Premium reverse osmosis water filtration system Stella is the perfect blend of cutting-edge design, luxurious comfort, and thoughtful craftsmanship--an exceptional opportunity in one of the area's most sought-after communities.

213 Westhampton Dr, Pittsboro
64 Mist Wood Ct, 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
191 High Ridge Ln, 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 .

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