Pittsboro Homes with Community Pool

Welcome to Pittsboro, North Carolina—a charming town nestled in the heart of Chatham County that perfectly blends small-town charm with modern conveniences. Known for its rich history and vibrant community spirit, Pittsboro offers a welcoming atmosphere for families, retirees, and everyone in between. With its picturesque landscapes and friendly neighbors, it’s no wonder that many are drawn to call this delightful town home.

One of the standout features of Pittsboro is its array of beautiful homes that come with access to community pools. Imagine spending hot summer days lounging by the water, enjoying a refreshing swim, or hosting barbecues with friends and family in a serene, well-maintained environment. These community pools not only provide a perfect escape from the summer heat but also foster a sense of camaraderie among residents, making it easy to forge lasting friendships.

Pittsboro is not just about the homes; it’s about the lifestyle. With an array of local shops, delicious eateries, and outdoor recreational opportunities, there’s always something to explore. Whether you’re hiking along the scenic trails of nearby parks or savoring a meal at a local café, you’ll find that Pittsboro is a place where community and nature thrive together.

If you’re seeking a home in a place where you can enjoy both comfort and connection, look no further than Pittsboro, NC. With its welcoming community and homes that feature access to community pools, you’ll find the perfect setting to create lasting memories. Come discover the charm of Pittsboro today!

Newest Pittsboro Homes with Community Pool

$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

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 10161024 MLS ⋅ ACTIVE Status

A rare opportunity awaits in the exclusive Estates at Chapel Ridge. This distinguished Prewitt-Douglas custom home sits on nearly an acre -- one of the last remaining lots in this coveted enclave. Spanning over 3,500 square feet, the residence showcases high-end finishes throughout and a desirable main-level primary suite complete with dual walk-in closets. Four bedrooms and 3.5 baths offer ample space for comfortable everyday living and effortless entertaining. Residents enjoy access to Chapel Ridge's full suite of community amenities, providing year-round recreation for the entire family. Exceptional craftsmanship, a premier lot, and an unmatched location -- opportunities like this are few and far between.

36 Rosefield 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

$824,900

3 Beds ⋅ 3 Baths ⋅ 10165069 MLS ⋅ ACTIVE Status

Set on one of the most coveted homesites in Encore at Chatham Park, this exceptional residence offers refined, single-level living at its finest. The largest single level ''Moorefield'' model in the community, the home spans approximately 2,668 square feet and is enhanced by a thoughtfully added 175-square-foot flex or craft room, providing both elegance and versatility. Designed with a keen eye for detail, the home features three spacious bedrooms and three beautifully appointed full bathrooms. The dining room is anchored by a sophisticated Valor fireplace, creating a warm yet elevated ambiance ideal for entertaining. The gourmet kitchen is a true centerpiece, showcasing upgraded cabinetry, a custom designer backsplash, striking countertops, and an impressive 10-foot chestnut oak hardwood-wrapped island--perfect for gatherings both intimate and grand. Outdoors, the property is equally captivating. Lush, meticulously curated landscaping graces both the front and rear grounds, complemented by a charming stone wall that enhances the home's distinguished presence. A mature, fruit-bearing fig tree adds a rare and delightful touch, completing this one-of-a-kind offering in one of Pittsboro's most desirable communities.

33 Imagine Way, 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

Start Your Search

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 .