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

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
755 Arrowhead Loop, Pittsboro
$1,400,000
3 Beds ⋅ 4 Baths ⋅ 10193626 MLS ⋅ ACTIVE Status
Set in an established equestrian neighborhood, this thoughtfully updated 15-acre mini farm offers country living with exceptional recreational and homesteading amenities. Fresh interior paint and newly refinished hardwoods complement the open floor plan and newly built pantry area. Enjoy the backyard oasis with a pool, hot tub and gas fire pit, plus a convenient pool house with bathroom. The property also features an irrigation system, fenced pastures, stables, double-gated chicken coops and a duck house. The custom four-stall barn has been rebuilt and enhanced with two storage rooms. Electricity serves the barn, stables, coops and pool house. Additional upgrades include HVAC, a whole-house generator, water filtration, crawl-space protection, French drains, expanded propane capacity and a separate garage/storage building. With no HOA or city taxes, this property is a dream come true.

755 Arrowhead Loop, Pittsboro
226 Evington Dr, Pittsboro
$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
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
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
227 Deep Crk, 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
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
774 Golfers Vw, 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
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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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