Pittsboro Homes with In Ground Pool

Pittsboro Homes with In Ground Pool

Welcome to Pittsboro, North Carolina – a charming town nestled in the heart of Chatham County that beautifully blends small-town charm with modern conveniences. Known for its rich history and vibrant community, Pittsboro is surrounded by stunning natural landscapes, making it an ideal place for those who appreciate the great outdoors. With its quaint downtown area filled with unique shops, delightful eateries, and local art galleries, Pittsboro offers a warm, inviting atmosphere that feels like home.

For those seeking a touch of luxury and relaxation, Pittsboro boasts an impressive selection of homes featuring in-ground pools. Imagine stepping out into your backyard oasis, where you can unwind under the warm North Carolina sun or host summer gatherings with friends and family. These properties provide the perfect backdrop for a lifestyle that embraces leisure and entertainment.

The real estate market in Pittsboro is diverse, offering everything from charming historic homes to modern builds, all designed to meet the needs of today’s homeowners. With the added allure of in-ground pools, these homes not only provide a refreshing retreat but also enhance your outdoor living experience.

Living in Pittsboro means enjoying the best of both worlds – a peaceful, rural setting with easy access to larger cities like Chapel Hill and Raleigh. Whether you’re looking to settle down or invest in a vacation home, Pittsboro’s inviting community and stunning properties with in-ground pools are sure to captivate your heart. Come explore the possibilities that await you in this delightful North Carolina town!

Newest Pittsboro Homes with In Ground Pool

$2,150,000
4 Beds ⋅ 4 Baths ⋅ 10191808 MLS ⋅ ACTIVE Status
Welcome to 226 Evington Drive, an extraordinary custom property set on 2.3 acres in Riverstone Estates, one of Chatham County's most distinguished luxury communities, backing to protected North Carolina State Park land. This one-owner residence offers exceptional privacy, a serene natural backdrop and convenient access to Jordan Lake, Wake County, UNC-Chapel Hill, Duke and RDU International Airport. Originally built by Sadler Construction, the home makes a striking first impression with its timeless white-brick exterior, dark-framed windows and professionally designed grounds. Inside, 10-foot ceilings, site-finished white oak floors, white oak trim, extensive custom millwork, architectural arches, ceiling beams, specialty cabinetry and upgraded Emtek hardware reflect an extraordinary level of craftsmanship. Thoughtful universal-design features including wide passageways, zero-entry main-level living and garage access, accessible baths and planning for a future elevator allow the home to live beautifully through every season of life. At its heart, the chef's kitchen showcases custom Harrison Vintson cabinetry, quartz countertops and backsplash, a full Thermador appliance package, XO wine refrigeration, integrated wine storage and a hand-finished plaster range hood designed to coordinate with the living room fireplace. A beautifully appointed butler's pass-through and thoughtfully designed cabinetry make entertaining effortless. The living room is equally compelling, featuring a custom plaster fireplace, white oak built-ins, Dekton surfaces and integrated color-changing lighting. Oversized sliding doors reveal the home's signature indoor-outdoor sightline, extending from the living room to the vaulted screened porch, where continuing ceiling beams and warm cedar detailing create a seamless architectural connection. Two bedrooms are conveniently located on the main level, including a private guest suite with its own exterior entrance and en suite bath, ideal for multigenerational living, extended-stay guests or an au pair. The primary suite features remote-controlled Lutron shades, custom built-ins and a spa-inspired bath wrapped in floor-to-ceiling marble tile. Remote-controlled Phantom screens open to a private resort-style backyard anchored by a 40-by-20-foot saltwater pool with a tanning ledge, approximately seven-foot depth and app-controlled lighting. Electrical infrastructure is already in place for a future pool heater. A white-brick outdoor gas fireplace, custom patio flooring, generous lounging areas and an upper-level Trex deck overlooking the pool provide exceptional spaces for gathering, entertaining and relaxing. Approximately $150,000 in professionally designed landscaping surrounds the residence with remarkable beauty. Bermuda grass, drip irrigation, extensive landscape lighting, mature ornamental trees and layered flowering gardens create the atmosphere of a secluded retreat. Iron fencing, a fully enclosed backyard and the protected wooded backdrop provide a degree of privacy rarely found this close to the Triangle's major destinations. Additional highlights include a beautifully designed mudroom, an exceptionally appointed laundry room with an upstairs laundry chute, a playroom or flex space, professional-grade gym flooring, walk-in closets, abundant attic storage, a water softener, epoxy-finished garage floors, built-in garage storage, upgraded heavy-duty garage doors and electric-vehicle charging. 226 Evington Drive presents a rare opportunity to own a private Pittsboro luxury estate where architectural distinction, thoughtful accessibility, resort-caliber outdoor living and effortless Triangle connectivity come together.

226 Evington Dr, 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
$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
$2,999,000
5 Beds ⋅ 6 Baths ⋅ 10176685 MLS ⋅ ACTIVE Status
Set on nearly 1.8 wooded acres in The Hamptons Summit, this exceptional custom home offers a rare combination of sophisticated design, remarkable space and privacy. All just minutes from Jordan Lake and convenient to Chapel Hill, Pittsboro and the Triangle. Built in 2024 and offering approximately 5,744 square feet, the home was thoughtfully designed for both everyday living and effortless entertaining. Expansive windows fill the main living spaces with natural light while framing the surrounding trees, creating a sense of privacy and connection to the outdoors. At the heart of the home is a beautifully appointed chef's kitchen featuring a Wolf gas range, Wolf wall oven and Wolf microwave, an oversized island, abundant custom cabinetry and generous gathering space. A separate second kitchen provides additional prep, cooking and storage space; an exceptional feature for entertaining, hosting family and friends, or simply keeping the main kitchen beautifully organized. The main level offers two bedroom suites, including a spacious primary retreat with a spa inspired bath and generous walk-in closet. A second main-level bedroom with its own private bath provides flexibility for guests, multi-generational living or a private home office. Upstairs, additional bedrooms are complemented by an expansive bonus room, loft/flex space and access to an upper-level balcony, providing plenty of room to spread out, work, relax or entertain. Adding to the home's thoughtful functionality are two separate laundry rooms - one on each floor; making everyday living remarkably convenient in a home of this scale. Outside, the private setting becomes an extension of the living space. Surrounded by mature trees, the backyard features a swimming pool and generous areas for gathering, relaxing and enjoying the peaceful surroundings. With nearly two acres, the property offers a level of privacy increasingly difficult to find while remaining connected to everything the Triangle has to offer. A four car garage, EV charging capability, extensive storage and thoughtful details throughout complete a home that is as functional as it is beautiful. 196 Mountaintop Circle isn't simply about square footage or finishes; it is a home designed for how people truly want to live: room to gather, room to retreat, exceptional spaces for entertaining and a private setting that feels worlds away without being far from anything.

196 Mountaintop Cir, Pittsboro
$965,000
4 Beds ⋅ 4 Baths ⋅ 10084591 MLS ⋅ ACTIVE Status
Beautiful custom home in the highly desirable Chapel Ridge neighborhood. The primary suite and guest bedroom are on the first floor with two additional bedrooms upstairs. This wonderful open floor plan gives you plenty of room to entertain. Walking distance to the many community amenities including the pool, golf and tennis.

829 Chapel Ridge Dr, 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
$1,230,000
4 Beds ⋅ 9 Baths ⋅ 10159657 MLS ⋅ ACTIVE Status
Exceptional Prewitt-Douglas custom home overlooking Chapel Ridge golf course. This 3,365 SF residence offers 4 bedrooms, 4.5 baths, a 2-car garage, and a dedicated golf viewing room ideal for entertaining. Quality craftsmanship throughout with sweeping golf course views. A rare find in a premier setting -this one won't last long.

227 Deep Crk, 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
$1,290,000
4 Beds ⋅ 5 Baths ⋅ 10161733 MLS ⋅ ACTIVE Status
Beautiful Prewitt-Douglas Custom 4 bedroom 4.5 bath custom built golf course home on the 14th fairway. Enjoy expansive views from the rear porch and the many amenities in Chapel Ridge including pool, tennis, pickle ball, volleyball, and golf.

774 Golfers Vw, 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 .