Pittsboro Homes with Chatham - Jordan Matthews High High School

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

3477 Castle Rock Farm Rd, Pittsboro
$1,300,000
4 Beds ⋅ 2 Baths ⋅ 10198647 MLS ⋅ ACTIVE Status
RARE FIND! A peaceful retreat in Chatham County! This beautiful 42+ acre property offers the perfect combination of privacy, convenience, and endless possibilities, located just 25 minutes from Chapel Hill, 20 minutes from downtown Pittsboro and Chatham Park, and 5 minutes from Chapel Ridge Golf Course. This updated 4-bedroom home is move-in ready and offers beautiful views from nearly every window. The main level features two guest bedrooms, an inviting living room with a woodburning fireplace and soaring ceilings overlooking the deck and private, tree-lined backyard, formal dining area, and an updated kitchen with new appliances. Upstairs you'll find the spacious primary bedroom with a sitting area, large walk in closet and a "secret" room, an additional guest bedroom, and office space overlooking the serene front yard. Recent updates include fresh interior paint, new downstairs HVAC, updated bathrooms. There is abundant storage and a water treatment system. Outside, the property offers fenced pastures, mature hardwood trees, open acreage, road frontage, and multiple existing structures. The possibilities are truly exceptional. The property could lend itself to a multigenerational setup, private family compound, equestrian or agricultural use, guest accommodations, "barndominium" event or retreat space, short-term rental opportunities, or simply a peaceful private homestead. The existing accessory dwelling offers additional potential and includes its own well and septic (this second septic needs repair), washer/dryer hookups, and a charming claw foot tub. The pole barn provides additional storage and could potentially be converted into a large garage, workshop, equipment storage, or collector's space. Enjoy the main home today while taking your time to envision the future of this remarkable property. Whether you're looking for room to spread out, space for animals, additional living options, or a property with long-term potential, this is a rare opportunity to own 42+ acres in a beautiful and convenient Chatham County setting. A property with this much land, privacy, infrastructure, and versatility doesn't come along often! Don't let this little slice of paradise slip away schedule your private tour today! There is no for sale sign look for the red mailbox.

3477 Castle Rock Farm Rd, Pittsboro
Tbd 3 Henderson Tanyard, Pittsboro
$649,450
10197938 MLS ⋅ ACTIVE Status
Showings by Appointment Only. Tract 3 offers 20.95 +/- acres with a beautiful combination of open pasture and wooded acreage, giving you space, privacy, and plenty of possibilities. Potential homesites toward the back of the property offer an elevated setting with views overlooking the pasture, woods, and surrounding countryside. With nearly 21 acres to work with, there's plenty of room to bring your plans to life. Build your home farther off the road for added privacy, create a homestead or farm, bring the horses, or simply enjoy having your own piece of the country. And while the setting feels private, you're still within an easy drive of Pittsboro, Chapel Hill, Apex, Siler City, Raleigh, and Greensboro. The property has been evaluated by a soil scientist for septic suitability for residential use; however, no septic permit has been applied for or issued. And if 20.95 acres isn't quite enough, there's room to think bigger. Adjoining Tracts 1 and 2 are also being offered separately, giving buyers the option to purchase additional acreage and create a larger property. Buy one tract, combine two, or explore the opportunity to purchase all three.

Tbd 3 Henderson Tanyard, Pittsboro
Tbd 2 Henderson Tanyard Rd, Pittsboro
$670,400
10197923 MLS ⋅ ACTIVE Status
Showings by Appointment Only. Tract 2 offers 20.95 +/- acres with a beautiful combination of open pasture and wooded acreage, giving you space, privacy, and plenty of possibilities. Potential homesites toward the back of the property offer an elevated setting with views overlooking the pasture, woods, and surrounding countryside. With nearly 21 acres to work with, there's plenty of room to bring your plans to life. Build your home farther off the road for added privacy, create a homestead or farm, bring the horses, or simply enjoy having your own piece of the country. And while the setting feels private, you're still within an easy drive of Pittsboro, Chapel Hill, Apex, Siler City, Raleigh, and Greensboro. The property has been evaluated by a soil scientist for septic suitability for residential use; however, no septic permit has been applied for or issued. And if 20.95 acres isn't quite enough, there's room to think bigger. Adjoining Tracts 1 and 3 are also being offered separately, giving buyers the option to purchase additional acreage and create a larger property. Buy one tract, combine two, or explore the opportunity to purchase all three.

Tbd 2 Henderson Tanyard Rd, Pittsboro
Tbd 1 Henderson Tanyard Rd, Pittsboro
$691,350
10196249 MLS ⋅ ACTIVE Status
Showings by Appointment Only Tract 1 offers 20.95 +/- acres with a beautiful combination of open pasture and wooded acreage, giving you space, privacy, and plenty of possibilities. Potential homesites toward the back of the property offer an elevated setting with views overlooking the pasture, woods, and surrounding countryside. With nearly 21 acres to work with, there's plenty of room to bring your plans to life. Build your home farther off the road for added privacy, create a homestead or farm, bring the horses, or simply enjoy having your own piece of the country. And while the setting feels private, you're still within an easy drive of Pittsboro, Chapel Hill, Apex, Siler City, Raleigh, and Greensboro. The property has been evaluated by a soil scientist for septic suitability for residential use; however, no septic permit has been applied for or issued. And if 20.95 acres isn't quite enough, there's room to think bigger. Adjoining Tracts 2 and 3 are also being offered separately, giving buyers the option to purchase additional acreage and create a larger property. Buy one tract, combine two, or explore the opportunity to purchase all three.

Tbd 1 Henderson Tanyard Rd, Pittsboro
2251 Castle Rock Farm Rd, Pittsboro
$290,000
3 Beds ⋅ 2 Baths ⋅ 10193707 MLS ⋅ ACTIVE Status
*Listed BELOW appraisal value* Discover the possibilities with this 3-bedroom, 2-bath brick ranch nestled on 4.36 acres. Offering plenty of room to spread out, this property provides a great opportunity for someone looking for acreage, privacy, and a home they can make their own. The home could use some updating and TLC, making it a great candidate for buyers who want to add their personal style and improvements over time. The spacious layout includes a fireplace with gas logs; the gas logs are in working condition but will need to be serviced. Outside, the property offers plenty of flexibility. A covered shelter behind the home could provide storage or be useful for those wanting to keep animals. A carport offers covered parking, while the expansive acreage gives you room for gardening, recreation, outdoor projects, or simply enjoying the surrounding space. Additional features include a whole-house generator for added peace of mind and a shared well. If you're looking for a brick ranch with acreage and the opportunity to build equity through updates, this property is ready for its next chapter. This property was previously listed together with 2225 Castle Rock Farm Road but is now being offered separately. The sellers have established a well easement for 2251 Castle Rock Farm Road. The property shares a well with 2225 Castle Rock Farm Road. Come see the potential and imagine what you can create here!

2251 Castle Rock Farm Rd, Pittsboro
755 Arrowhead Loop, Pittsboro
$1,400,000
3 Beds ⋅ 4 Baths ⋅ 10193626 MLS ⋅ ACTIVE Status
Set in an established equestrian neighborhood, this thoughtfully updated 15-acre mini farm offers country living with exceptional recreational and homesteading amenities. Fresh interior paint and newly refinished hardwoods complement the open floor plan and newly built pantry area. Enjoy the backyard oasis with a pool, hot tub and gas fire pit, plus a convenient pool house with bathroom. The property also features an irrigation system, fenced pastures, stables, double-gated chicken coops and a duck house. The custom four-stall barn has been rebuilt and enhanced with two storage rooms. Electricity serves the barn, stables, coops and pool house. Additional upgrades include HVAC, a whole-house generator, water filtration, crawl-space protection, French drains, expanded propane capacity and a separate garage/storage building. With no HOA or city taxes, this property is a dream come true.

755 Arrowhead Loop, Pittsboro
535 Poplar Forest Ln, Pittsboro
$599,000
3 Beds ⋅ 4 Baths ⋅ 10189120 MLS ⋅ ACTIVE Status
NEW PRICE! Come home to this beautiful property on more than 2.5 acres with brand new ROOF! Enjoy the gracious wrap-around front porch, 9-ft ceilings, site finished hardwoods, & updated kitchen with new cabinets and quartz counters. Host Thanksgiving in the spacious dining room with a large bay window. 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. Fiber internet connected and all appliances convey!

535 Poplar Forest Ln, Pittsboro
2865 Silk Hope Gum Springs Rd, 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 within a few miles of 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! Country Living in Chatham County, NC! 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 within a few miles of 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! Country Living in Chatham County, NC!

2865 Silk Hope Gum Springs Rd, Pittsboro
Henderson Tanyard Rd, Pittsboro
$1,950,000
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
Silk Hope Gum Springs 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—doesn't come along often in Pittsboro. Bring your vision and make the most of this expansive, positioned property.

Silk Hope Gum Springs Rd, Pittsboro
2817 Silk Hope Gum Springs Rd, Pittsboro
$949,800
4 Beds ⋅ 4 Baths ⋅ 10119230 MLS ⋅ ACTIVE Status
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! 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. Move in Ready! Be the First Homeowner of this Custom Built Home!! 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! 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. Move in Ready! Be the First Homeowner of this Custom Built Home!!

2817 Silk Hope Gum Springs Rd, Pittsboro
2953 Silk Hope Gum Spring Rd, Pittsboro
$259,900
10119955 MLS ⋅ ACTIVE Status
Build your Custom Dream Home!! 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 town, 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 Dreams to Life!!! Build your Custom Dream Home!! 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 town, 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 Dreams 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 .

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