Pittsboro Homes with Chatham - Jordan Matthews High High School

Welcome to Pittsboro, North Carolina—a charming town nestled in the heart of Chatham County. Known for its rich history, vibrant community, and stunning natural landscapes, Pittsboro offers a unique blend of small-town charm and modern conveniences. With its picturesque downtown area, lined with quaint shops, local eateries, and friendly faces, it’s no wonder that residents feel a deep sense of belonging here.

One of the standout features of Pittsboro is its strong commitment to education, particularly for families seeking quality schooling options. Homes in Pittsboro fall within the Chatham - Jordan Matthews High School district, renowned for its dedication to academic excellence and fostering a supportive learning environment. This makes Pittsboro not just a place to live, but a place where families can thrive and children can flourish.

Outdoor enthusiasts will appreciate the abundance of recreational opportunities, including nearby parks, hiking trails, and scenic waterways. The area is also home to various community events and festivals that bring residents together, celebrating the rich cultural tapestry of Pittsboro.

Whether you’re a first-time homebuyer or looking to relocate, Pittsboro offers a diverse range of housing options, from historic homes to modern builds, all set against a backdrop of stunning North Carolina landscapes. With its friendly atmosphere, strong educational foundation, and vibrant community life, Pittsboro is more than just a place to live—it’s a place to call home. Come discover the charm of Pittsboro, where your dream home awaits!

Newest Pittsboro Homes with Chatham - Jordan Matthews High High School

$640,000

3 Beds ⋅ 4 Baths ⋅ 10189120 MLS ⋅ ACTIVE Status

Need room to breathe? Welcome to 535 Poplar Forest Ln, a spacious home located on more than 2.5 acres in popular Bobcat Point! This home welcomes you with a long driveway & gracious wrap-around front porch. On the 1st floor you'll find 9-ft ceilings, site finished hardwoods, & an updated kitchen. The kitchen, family room, & breakfast room are bathed in natural light in this south-facing home, & the half-bath has been updated with all new fixtures. On the 2nd floor there is a large primary suite & three additional rooms w/closets that can be used as bedrooms, home offices, or bonus space. On the 3rd floor you'll find a full bath & two more rooms, perfect for a guest or teen suite. Outside enjoy the screened porch & deck overlooking the fenced back yard w/plenty of sun for gardening. Roof replaced in 2026, all appliances convey, AND Fiber internet connected. The total package!

535 Poplar Forest Ln, Pittsboro

$150,400

10119404 MLS ⋅ ACTIVE Status

Build Your Custom Home! Nestled on a serene 1.99-acre parcel w/ a 4-bedroom perk in place, this beautiful lot offers the perfect blend of privacy and convenience. Located just off Highway 64, you'll enjoy easy access to Siler City, Chapel Hill, Apex, and Cary—making your daily commute a breeze while still coming home to peace and quiet. Whether you're envisioning a cozy retreat or a spacious estate, Lot 3 is ready for your vision and you can bring your own builder. Set in a thriving community, this property invites you to build your forever home in a location that truly has it all.

2865 Silk Hope Gum Springs Rd, Pittsboro

$2,075,000

10112548 MLS ⋅ ACTIVE Status

**Showings by Appointment Only** Increasing rare opportunity to own 62.87 acres +/- of land in Pittsboro, NC! This secluded land is comprised of three lots (all with road frontage) on the quiet country Henderson Tanyard Road. The property boasts beautiful natural features and scenic sights. Potential house seats sit atop the backside of the property, offering panoramic views of timber, wildlife, and the hayfield/pasture below. This property is a blank canvas for someone looking to create their own homestead, farm/horse farm, or weekend getaway. Seclusion and privacy do not mean you have to live several hours from conveniences, this land is just a short commute from the following: Pittsboro - 13 mins Apex - 30 mins Siler City 15 mins Chapel Hill - 23 mins Greensboro - 45 mins Raleigh - 45 mins Although no septic permits have been applied for or issued, each comprising lot has been evaluated by a soil scientist for septic suitability for residential housing. With development pushing in from every direction, do not waste any time securing this property and making it your own!

Henderson Tanyard Rd, Pittsboro

$759,000

10142077 MLS ⋅ ACTIVE Status

Discover 13+ acres of versatile land in a prime Pittsboro location, offering both privacy and convenience. An established easement provides driveway access to the majority of the property, creating a smooth path for building your dream home or exploring subdivision potential. With gently rolling terrain and ample space to design your ideal layout, this tract is well‑suited for a single private residence, a family compound, or multiple homesites. The setting feels peaceful and tucked away, yet you're just minutes from Highway 87 and US‑64, making commuting and everyday errands remarkably easy. Opportunities like this—size, flexibility, and location—don't come along often in Pittsboro. Bring your vision and make the most of this expansive, well‑positioned property.

Silk Hope Gum Springs Rd, Pittsboro

$400,000

3 Beds ⋅ 2 Baths ⋅ 10156977 MLS ⋅ ACTIVE Status

*Calling all Cash Buyers* 2 parcels - 5.99 acres in total! Discover a unique investment and lifestyle opportunity with this dual-home property offering flexibility, income potential, and rural charm. Situated on a SHARED WELL, this property includes a spacious primary residence and a singlewide home--both being sold together as one package! The primary home provides comfortable living with ample space for a family, featuring 3 bedrooms, 2 bathrooms and a whole house generator on 4.36 acres. It could use some updating and TLC but whether you're looking for a peaceful retreat or a place to put down roots, this home delivers both comfort and functionality. Gas logs in fireplace will need to be serviced but are in working condition. In need of storage or want some animals? There's a covered shelter behind the home. Parcel# 0010598 Just steps away, the singlewide offers a fantastic opportunity for rental income, multigenerational living, or guest accommodations with 2 bedrooms, 2 bathrooms situated on 1.63 acres. Live in the primary home and rent out the singlewide, or use it as a private space for extended family. Parcel #0089788 Again, both homes share a well and have storage buildings out back at each. The primary home has a carport and offers plenty of outdoor space for gardening, recreation, or future improvements. If you're seeking versatility, value, and income potential all in one property, this is a rare find you won't want to miss. Schedule your showing today and explore the possibilities!

2251 Castle Rock Farm Rd, Pittsboro

$949,800

4 Beds ⋅ 4 Baths ⋅ 10119230 MLS ⋅ ACTIVE Status

Ready for YOU to MOVE IN!! This stunning quality built house of 4-bedroom, 3.5-bath home offers over 3,200 square feet, well designed living space, nestled on a serene 2-acre parcel. NO HOA'S! Perched gently atop a hill, the property enjoys elevated views and a sense of quiet retreat--while still being just minutes from town. Step onto the inviting front porch and into a light-filled interior where soaring ceilings, expansive windows, and a cozy fireplace create a warm, open atmosphere. CUSTOM HARDWOOD FLOORS, throughout the entire home---NO CARPET. The heart of the home features brand-new appliances and sleek finishes, blending modern convenience with classic comfort. Whether you're sipping morning coffee on the screened-in back porch or hosting guests in the spacious living areas, this home is built for both relaxation and connection. With generous bedrooms, well-appointed primary suite, and seamless indoor-outdoor flow, it's a perfect match for those seeking peaceful, country living without sacrificing accessibility.

2817 Silk Hope Gum Springs Rd, Pittsboro

$259,900

10119955 MLS ⋅ ACTIVE Status

Truly a special location, tucked away on 3.79 wooded acres, this property offers a tranquil escape surrounded by mature trees and lush greenery. It's the kind of place where morning coffee comes with birdsong and evening walks feel like a retreat into nature. Despite its serene setting, you're just minutes from townâ€"giving you the best of both worlds: privacy and proximity. Whether you're planning to build your forever home or invest in land with lasting value, this lot delivers. 4-bedroom conventional perc already approved, High-speed fiber optics available via Randolph Communications & the freedom to choose your own builder to bring your vision to life.

2953 Silk Hope Gum Spring 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 .