Pittsboro Homes with Guilford - George Moses Horton Middle School

Welcome to Pittsboro, North Carolina—a charming town steeped in rich history and surrounded by the stunning natural beauty of Chatham County. Nestled just a short drive from the bustling city of Chapel Hill, Pittsboro offers a perfect blend of small-town charm and modern conveniences. With its picturesque downtown area, residents enjoy a vibrant community atmosphere, complete with local shops, delightful eateries, and annual festivals that celebrate the town’s heritage.

One of the highlights of living in Pittsboro is its proximity to excellent educational opportunities. Homes in this area are served by the highly regarded Guilford - George Moses Horton Middle School, known for its commitment to academic excellence and fostering a supportive learning environment. Families will appreciate the school’s focus on innovation and character development, ensuring that students are well-prepared for their future endeavors.

The real estate landscape in Pittsboro is diverse, offering something for everyone—from cozy single-family homes to spacious properties with sprawling yards. Many homes boast stunning views of the surrounding countryside, providing a tranquil retreat from the hustle and bustle of city life. Whether you are a first-time homebuyer or looking to settle down in a serene community, Pittsboro has a variety of options to suit your needs.

With its rich cultural heritage, community spirit, and access to quality education, Pittsboro is not just a place to live—it's a place to thrive. Explore the charm of this hidden gem in North Carolina, where your dream home awaits!

Newest Pittsboro Homes with Guilford - George Moses Horton Middle School

$410,000

3 Beds ⋅ 3 Baths ⋅ 10163581 MLS ⋅ ACTIVE Status

This beautifully maintained end-unit townhome in the highly sought-after Chatham Park community still feels brand new, owned by its original 2023 owners. Designed with an open and inviting layout, the home features luxury vinyl plank flooring on the main level, hardwood stairs, and a cozy electric fireplace that anchors the living space. The kitchen is both stylish and functional, showcasing quartz countertops, a tile backsplash, gas cooktop, and built-in wall oven-perfect for everyday living and entertaining alike. Upstairs, the spacious primary suite offers a spa-like bathroom with a large walk-in tile shower, double vanities, and generous walk-in closet. Secondary bedrooms include walk-in closets, providing ample storage throughout. Step outside to enjoy the oversized front courtyard, while the rear-facing garage offers a long driveway with additional parking. The garage itself is immaculate, featuring durable polyurea flooring, built-in storage, an EV charger for electric vehicles, a dedicated 20-amp outlet, & a velcro garage bug net. Since purchasing, the owners have thoughtfully enhanced the home with custom upgrades including elegant window moldings, a built-in spice rack and kitchen shelving, and added cabinetry in the bathroom and laundry areas. This home is truly move-in ready and impeccably maintained-an exceptional opportunity in one of the area's most desirable communities.

277 Wendover Pkwy, Pittsboro

$699,000

3 Beds ⋅ 3 Baths ⋅ 10157338 MLS ⋅ ACTIVE Status

There are homes... and then there are lifestyles. Welcome to the one that gives you both. And now even better! Built by the highly regarded Homes By Dickerson, this Green Certified ranch in Chatham Park is where thoughtful design meets effortless living. From the moment you walk in, you feel it, the warmth of engineered hardwood floors stretching across the main level, the natural flow of an open layout, and the kind of light that makes every space feel inviting. At the heart of the home, a true chef's kitchen steals the show: crisp white cabinetry, a striking gray island, quartz countertops, and stainless steel appliances, all perfectly positioned to keep you connected to the dining area and living room with custom built-ins. The main-level owner's suite is more than just a bedroom, it's your private retreat. Think spa-like bath, designer tile, and an oversized walk-in shower that makes everyday routines feel elevated. Add a second bedroom and a dedicated office on the first floor, and you have the flexibility today's buyers are searching for. Upstairs offers even more: a private bedroom and full bath, plus a massive unfinished storage area, ready to become whatever your future needs demand (bonus room, gym, studio... you name it). And then there's the porch. Screened, serene, and overlooking the woods. Your own quiet escape for morning coffee or evening unwinding. Living in Chatham Park means stepping into one of the Triangle's most exciting and thoughtfully planned communities. Enjoy parks, playgrounds, splash pad, dog park, sports fields, zip line, pickleball courts, a private pool, and over 30 miles of greenways. All just minutes from Jordan Lake State Recreation Area, downtown Pittsboro, and easy access to University of North Carolina at Chapel Hill. This isn't just a home! it's the next chapter you've been waiting for.

52 Shergold Dr, Pittsboro

$925,000

4 Beds ⋅ 4 Baths ⋅ 10161198 MLS ⋅ ACTIVE Status

Newly completed and ready to welcome you home, The Mattie Plan by Pine State Construction Group is a stunning custom residence nestled on 1.33 private acres in Pittsboro, just 2 miles off HWY 64. Surrounded by mature hardwoods and just minutes from the charm of downtown Pittsboro, this exceptional home blends timeless craftsmanship with elevated modern design. Designed for everyday living and effortless entertaining, the open-concept family room features a cozy gas fireplace framed by custom built-ins and floating shelves. At the center of the home, the designer kitchen is truly unforgettable, featuring a striking sage green island topped with luxurious Taj Mahal quartz that continues seamlessly up the backsplash. An apron-front farmhouse sink, elegant gold bridge faucet, stained cabinetry, custom painted vent hood, and thoughtfully designed coffee bar with open shelving complete this one-of-a-kind gathering space. The main-level owner's retreat offers a private sanctuary with a spa-inspired bath featuring dual vanities, quartz countertops, designer gold fixtures, illuminated mirrors, and carefully selected finishes throughout. A guest suite and dedicated home office on the main floor provide exceptional flexibility, while the second level offers additional living space for family and guests. Expansive bi-parting sliding doors open to a covered rear deck overlooking peaceful wooded views, creating a seamless connection between indoor and outdoor living. Offering privacy, luxury finishes, and custom craftsmanship on over an acre of land, this completed home delivers the perfect balance of peaceful country living with the convenience of being less than 10 minutes from historic downtown Pittsboro, dining, shopping, and the growing Chatham Park Comes Complete with front load washer and dryer, Bosch range, and dishwasher. https://www.enbridgegas.com/chathamcountysystemexpansion Embridge Natural Gas Expanding to Chatham County. See Documents attached.

2317 Alex Cockman 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 .