Pittsboro Homes with Chatham County Schools Middle School

Pittsboro Homes with Chatham County Schools Middle School

Welcome to Pittsboro, North Carolina – a charming town nestled in the heart of Chatham County! Known for its rich history and vibrant community, Pittsboro offers a perfect blend of small-town charm and modern conveniences. With its picturesque landscapes and friendly atmosphere, it’s no wonder that families and individuals alike are drawn to this delightful area.

Pittsboro is not just a place to call home; it’s a community that fosters connection and growth. The town is surrounded by lush greenery and serene landscapes, making it an ideal spot for outdoor enthusiasts. Whether you prefer hiking along the Haw River or exploring the local parks, there’s no shortage of natural beauty to enjoy.

Families will be pleased to know that Pittsboro is served by Chatham County Schools, providing quality education options for children of all ages. The commitment to academic excellence and community involvement makes these schools a cornerstone of the town, ensuring that your family has access to the resources they need to thrive.

In terms of real estate, Pittsboro offers a variety of homes that cater to diverse tastes and budgets. From charming historic houses to modern new builds, there’s something for everyone. The welcoming neighborhoods are perfect for raising a family, making friends, and creating lasting memories.

Experience the warmth of Pittsboro for yourself and discover why it’s a hidden gem in North Carolina. With its strong sense of community, beautiful surroundings, and excellent educational opportunities, you may just find that Pittsboro is the perfect place to call home.

Newest Pittsboro Homes with Chatham County Schools Middle School

33 Imagine Way, Pittsboro
$799,900
3 Beds ⋅ 3 Baths ⋅ 10201385 MLS ⋅ ACTIVE Status
Feels Better Than New! Nearly 2,700 square feet—all on one level, with three bedrooms, three full baths, and accessible features including a zero-entry primary shower. Add a dedicated craft room, a 10-foot kitchen island, and outdoor living backed by woods, and 33 Imagine Way offers space to gather, create, and settle in at Pittsboro's premier 55+ Encore at Chatham Park. Built in 2024, the home puts everyday living on the same floor without asking every room to do double duty. The craft room lets you leave a project in progress. A separate sitting room offers a quiet place to read or recharge. Three bedrooms keep space available for guests. The primary suite pairs practical comfort with personal style: a custom-organized walk-in closet, quartz-topped double vanity, and a tray ceiling accented in gold. Its zero-entry shower features ceiling-height tile, two shower heads, and transom windows. The kitchen deserves a closer look. Chestnut oak wraps the substantial island and coordinating vent hood, bringing warmth to the quartz countertops, custom backsplash, and Currey & Co. pendants. Cabinet pull-outs, a coffee bar, walk-in pantry, five-burner gas cooktop, and wall oven make the space work as well as it looks. Open sightlines connect it to the great room, while the adjoining dining area has its own focal point: a stone-enclosed Valor fireplace and custom chestnut oak wrapped hardwood display cabinet. Outside, stone walls frame the front garden. The covered rear porch extends to a permeable patio with a sitting wall, water feature, and fig tree. Take dinner outside. Let the conversation run long. Encore's clubhouse, fitness center, pool, hot tub, pickle ball, tennis, and putting green expand the possibilities, with dining, shopping, and entertainment nearby at MOSAIC. An attached two-car garage adds an EV charger and attic storage. Bring the hobbies, host the dinner, keep a guest room ready. There's room for it here.

33 Imagine Way, 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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