Pittsboro Homes with See Remarks Pool

Welcome to Pittsboro, North Carolina—a charming town nestled in the heart of Chatham County, where Southern hospitality meets a vibrant community spirit. Known for its picturesque landscapes and rich history, Pittsboro offers a unique blend of small-town charm and modern conveniences. With a population that embraces its roots while welcoming new residents, this delightful town is perfect for those seeking a peaceful yet engaging lifestyle.

Pittsboro boasts a variety of outdoor activities, from exploring the scenic trails of the nearby Jordan Lake State Recreation Area to enjoying the local farmers' market, where you can find fresh produce and handmade goods. The town is also home to several parks, providing ample opportunities for family picnics, leisurely strolls, and community events.

For those considering a move to this enchanting town, you'll be pleased to discover a selection of homes that feature stunning pools, perfect for soaking up the warm North Carolina sun. Imagine hosting summer barbecues or enjoying a relaxing evening by the water in your own backyard oasis. These homes with pools not only offer a luxurious lifestyle but also serve as a gathering place for family and friends, making every day feel like a vacation.

Whether you're drawn to the historic charm of Pittsboro's downtown area or the tranquility of its surrounding nature, this town is sure to capture your heart. Explore the possibilities of finding your dream home in Pittsboro, where comfort, community, and a refreshing pool await you!

Newest Pittsboro Homes with See Remarks 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

$2,150,000

5 Beds ⋅ 7 Baths ⋅ 10142171 MLS ⋅ ACTIVE Status

Your custom sanctuary in Firefly Overlook awaits. Discover the serenity and sophistication of Firefly Overlook at Jordan Lake—a premier new large-lot subdivision featuring just 30 exclusive homesites in the rapidly growing and highly desirable Chatham County. Perfectly positioned for effortless access to Apex, Pittsboro, Cary, and RDU Airport, this thoughtfully planned community places you moments from the pristine shores of Jordan Lake while offering a peaceful, nature-immersed retreat with rolling hills, panoramic views, and tranquil natural surroundings. This exceptional pre-sale opportunity on Lot 27—a beautifully central 1.55-acre homesite that enjoys prime visibility and prominence within the neighborhood—invites you to collaborate with renowned Triple A Homes to create your fully customized dream residence. The inspiring proposed design draws from Triple A Homes' award-winning plan, previously celebrated for its timeless elegance and innovative layout, and can be tailored entirely to your vision with personal selections, modifications, or unique enhancements. Envision this magnificent to-be-built custom home: a light-filled masterpiece featuring 5 luxurious bedrooms, including a serene primary suite and convenient main-level guest suite for ultimate comfort and privacy. The heart of the home is an expansive two-story great room with dramatic open-to-above volume, complemented by abundant oversized windows and large retractable doors that seamlessly blend indoor and outdoor living—flooding the spaces with natural light and creating the sensation of being enveloped by nature year-round. The gourmet designer kitchen flows into a dedicated scullery for effortless entertaining, while a bespoke wine cellar adds sophisticated charm. Step outside through the retractable doors to a spacious covered patio complete with a cozy fireplace—perfect for al fresco gatherings and quiet evenings under the stars. Lot 27's central location offers exceptional curb appeal and easy connection to the community's natural beauty, making your future home a standout landmark in this intimate enclave. Secure this rare central homesite today and partner with Triple A Homes to bring your personalized legacy residence to life. Construction timeline and customization details available upon inquiry.

372 Firefly Overlook Rd, 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 .