Pittsboro Homes with Fenced Pool

Pittsboro Homes with Fenced Pool

Welcome to Pittsboro, North Carolina, a charming town nestled in the heart of Chatham County. Known for its picturesque landscapes and vibrant community spirit, Pittsboro offers a perfect blend of small-town charm and modern conveniences. With a rich history dating back to the late 18th century, this quaint locale is surrounded by rolling hills, beautiful farmland, and serene waters, making it a haven for nature lovers and outdoor enthusiasts alike.

Pittsboro is not just a place to live; it’s a lifestyle. Residents enjoy a welcoming atmosphere, with local shops, farmers' markets, and delightful eateries that showcase the region's culinary delights. The town's commitment to preserving its historical roots while embracing growth is evident in its thriving arts scene and community events, fostering a sense of belonging for all who call this place home.

For those seeking the perfect family retreat, our listings in Pittsboro feature stunning homes with fenced pools, ideal for both relaxation and entertainment. Imagine hosting summer barbecues or enjoying a quiet evening under the stars by your private pool, all within the safety of a fenced yard. These homes are designed with modern amenities while maintaining a cozy, inviting ambiance, perfect for creating lasting memories with loved ones.

Whether you're looking to settle down in a vibrant community or seeking a peaceful escape from the hustle and bustle, Pittsboro offers an array of options to suit your lifestyle. Come explore the charm of Pittsboro and discover your dream home with a fenced pool today!

Newest Pittsboro Homes with Fenced Pool

$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
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
$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
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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 .