Pittsboro Homes with Chatham County Schools High School

Pittsboro Homes with Chatham County Schools High School

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 is a hidden gem that perfectly blends small-town charm with modern conveniences. With a rich history dating back to the 18th century, this quaint town boasts a unique blend of historic architecture and contemporary developments, making it an ideal place for families, retirees, and everyone in between.

One of the standout features of Pittsboro is its commitment to education, highlighted by its affiliation with Chatham County Schools. Families will be pleased to know that homes in this area are served by an excellent school district, ensuring that children receive a high-quality education. The local high school is well-regarded, providing a variety of academic and extracurricular opportunities that cater to diverse interests and talents.

Beyond its educational offerings, Pittsboro is surrounded by natural beauty, with access to serene parks, hiking trails, and the picturesque Haw River. Residents enjoy a tight-knit community atmosphere, with local events, farmers' markets, and festivals that foster connections among neighbors. The downtown area is brimming with unique shops, cozy cafes, and delightful eateries that celebrate the local culture and cuisine.

Whether you're looking for a peaceful retreat or an active lifestyle, Pittsboro has something for everyone. Explore the inviting neighborhoods, discover your dream home, and become part of a community that truly feels like family. Experience the charm of Pittsboro, where every day feels like a new adventure!

Newest Pittsboro Homes with Chatham County Schools High 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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