Pittsboro Real Estate Search

Pittsboro Properties for Sale

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Pittsboro Properties for Sale

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Newest Pittsboro Properties for Sale

383 Westhampton Dr, Pittsboro
$750,000
10137225 MLS ⋅ ACTIVE Status
This site is 2.974 Acres. County water, natural gas, fiber optics ready in place! Heavily Wooded. Also protected on one side with a 50 Vegetative Steam Buffer. Surpassing other luxury communities throughout Chatham, Orange, and Wake Counties. Home sites capable of accommodating some of the largest custom residences in the Triangle region, including the most sprawling ranch plans. Exceptional impervious surface allowances provide owners with the flexibility to create expansive outdoor living spaces, including pools, detached garages, guest houses, and accessory dwelling units and yes, even a pickle ball court or basketball court! Two fiber-optic internet providers available within the community. Municipal water service eliminates the need for private wells, with fire hydrants conveniently located throughout the neighborhood. Home sites are permitted for 5+ bedroom luxury plans. No city taxes. Whether large or small, every home is built to the highest standards of luxury, craftsmanship, and quality.County water, natural gas, fiber optics ready in place! This is a legacy home community with country estate living, while located close to many of the Triangle-area's top destinations. With home-sites ranging from one-acre to just under seven-acres and an elevation peak rising 600-feet above the community gas lit entrance, Summit offers a land plan that allows its homes to be gently stair-stepped into the mountainside for stunning views.. Summit is an exclusive new home community located just a couple miles from the Stunning Jordan Lake Preserve. Built by Sage Built Custom Homes, building legacy homes including many architectural styles and unlimited sizes, while located close to many of the Triangle-area's top destinations. We have nearly 30 Home-sites to choose from including Rolling Wooded Sites overlooking a Mountain Stream as well as well as open sites sitting high above the street and sites overlooking the Meadow. Each home is custom built to compliment the chosen site and will always include meticulous landscaping, Irrigation and low voltage lighting the driveways and even the mailboxes. The entryway design includes meticulously maintained areas, painted brick walls which welcome you to a truly magnificent place to build any legacy home with unlimited size and architectural designs. Located in an Excellent School District, including the New 74-million-dollar Seaforth High School only 6 Minutes away! Easy drive to RDU, Raleigh Executive Jetport, UNC Hospitals, and Campus, as well as RTP. The New I-540 is very convenient and the newest portion of the I-540 outer loop for easy access to I-40 towards the NC Coastal Areas and Great access to RDU and Durham.

383 Westhampton Dr, Pittsboro

297 Colonial Ridge Dr, Pittsboro
$1,650,000
5 Beds ⋅ 5 Baths ⋅ 10080780 MLS ⋅ ACTIVE Status
This stunning Modern English Tudor blends timeless architectural character with sophisticated modern finishes and exceptional indoor-outdoor living in the gated section of Chapel Ridge. Soaring 10' ceilings throughout the main level create an open, airy feel, while dramatic boxed beams and a sleek 60" linear fireplace make the Great Room an impressive centerpiece of the home. Designed for effortless entertaining, the open floor plan flows seamlessly to a gorgeous covered lanai featuring an outdoor fireplace and built-in grill. At the heart of the home is a showstopping ZLINE chef's kitchen, complete with a 48" professional-style range, 54" refrigerator/freezer, oversized waterfall island, and a cleverly designed hidden pantry that provides abundant storage while maintaining the kitchen's clean, sophisticated aesthetic. The thoughtfully designed main level also includes a second bedroom and a dedicated home office, offering flexibility for guests, multigenerational living, or working from home. An unfinished basement provides exceptional potential for future living and entertaining space, a home gym, theater, wine cellar, or additional bedrooms. Built to HERO energy-efficiency standards, this exceptional home combines distinctive Modern English Tudor style, luxury finishes, energy-conscious construction, and a floor plan designed for today's lifestyle. BUILDER HAS OTHER LOTS AND PLANS.

297 Colonial Ridge Dr, Pittsboro

267 Bald Eagle Dr, Pittsboro
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 10151608 MLS ⋅ ACTIVE Status
**BACK ON THE MARKET within 4 days of going under contract, due to no fault of the sellers.** While many luxury homes in the Triangle are constrained by tight lot sizes, 267 Bald Eagle Drive stands apart with 5.67 acres of true privacy and purposeful outdoor living. Designed for those who love adventure, the property includes a dedicated on site boat/RV barn, with the convenience of being just five minutes from Jordan Lake. This eliminates the need for off site storage that many neighborhoods' restrictive HOA rules would prohibit. Nestled in a small community with large lots and thoughtful protective covenants, this tract ensures natural privacy and quiet, along with night skies. The backyard is an entertainer's dream, featuring a covered porch, open deck, 6-person hot tub, and fire pit, with ample space should a future owner wish to add a pool. For gardeners, the property is nothing short of exceptional. The grounds are beautifully landscaped with seasonal interest and custom lighting and include a fenced garden area with its own potter's shed, creating a perfect environment for growing, cultivating, and unwinding. This picturesque home sits atop a ridgeline among predominantly hardwood trees. Bordered by a seasonal roadside creek, the property offers a serene escape just minutes from downtown Pittsboro and a short drive to major highways with access to Chatham Park, Apex, and Chapel Hill within 10 to 25 minutes. Two of the 5.67 acres are fenced with a three-rail wood fence, and a gated asphalt driveway leads up to spacious cement parking and sidewalk. This custom-built 4,406-sf home boasts 4 bedrooms, 3.5 bathrooms, including the 1,103-sf finished basement with a gym, media, and bonus room alongside 543-sf of unfinished space. The house is complete with a new roof and HVAC systems, and is connected with Spectrum high-speed fiber internet with incredibly fast speeds. Interior highlights include oak hardwood and tile flooring, casement windows, solid wood doors and glass doors. This home showcases a gorgeous formal dining room, a living room with a 2-story natural stone, wood-burning fireplace, and a home office with custom cherry cabinetry and a natural stone, gas log fireplace. The kitchen features custom natural maple cabinets accented with under-cabinet lighting, granite countertops, a high-end Wolf gas range with two ovens and a griddle, and stainless steel appliances. Just off the kitchen, the spacious utility suite has a double-door pantry, housekeeping storage, cabinetry for kitchen and laundry needs, laundry appliances, countertops, a utility sink, and a bathroom. The primary suite has a vaulted ceiling, a glassed-in vaulted ceiling porch, a walk-in closet, and is equipped with a steam shower and a jetted tub. The home's exterior is detailed with cedar shakes and natural stone, which are complemented by low-maintenance Brazilian Ipe hardwood on the rear deck, covered porch off the breakfast room, and the primary suite's enclosed porch.

267 Bald Eagle Dr, Pittsboro

148 Tobacco Rd, Pittsboro
$950,000
4 Beds ⋅ 4 Baths ⋅ 10163447 MLS ⋅ ACTIVE Status
Tucked away on almost two private acres with room for a pool, this custom designed Craftsman estate blends timeless architecture with refined luxury. The MAIN FLOOR PRIMARY SUITE with vaulted ceilings, his & her walk-in closets and spa bath make for a wonderful retreat. Also on the MAIN FLOOR is an IN-LAW/GUEST SUITE with it's own spa bath, living area, kitchen and private entrance. The open concept layout on the main floor ensures easy flow and great site lines between the family room, chef's kitchen, dining area and the gorgeous, renovated sunroom. Upstairs are TWO additional bedrooms, a huge OFFICE with custom closet space and a large bonus room. There is even 43 x 37 feet of floored attic space! Rich architectural details, custom millwork, and expansive windows create a warm yet sophisticated atmosphere throughout this home. Outdoor living is equally impressive. Stone patio and fire pit, a covered front porch, deck space for grilling and a covered hot tub offer many opportunities for relaxation or entertaining with friends. In addition to the 2-car attached garage, there is a detached garage with lots of space for cars, boats or wood working toys! And upstairs is a finished and conditioned room to be used however your heart desires! Close to Chapel Hill and Pittsboro, 148 Tobacco Road is just minutes from shopping and restaurants. With luxury finishes at every turn and a layout that can accommodate family and guests easily - you don't want to miss the opportunity to become the next lucky owner!

148 Tobacco 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

298 E Salisbury St, Pittsboro
$525,000
3 Beds ⋅ 2 Baths ⋅ 10159806 MLS ⋅ ACTIVE Status
NEWLY REZONED O&I — RESIDENTIAL FLEXIBILITY WITH EXCITING COMMERCIAL POTENTIAL! Offered for the first time in 40 years, the historic Thomas Hackney House (c. 1899), recognized in The Architectural Heritage of Chatham County, presents a rare opportunity just three blocks from downtown Pittsboro's shops, restaurants, and growing business district. Now approved for O&I zoning, this distinctive property offers new possibilities for a variety of office and professional uses while retaining the flexibility and character of a residential setting. Whether envisioned as a private residence, professional office, boutique business, studio, or other permitted O&I use, the possibilities are exceptional. Set on a secluded 0.4-acre lot shaded by mature hardwoods, this timeless bright house offers approximately 2,100 square feet featuring 2 bedrooms plus a spacious office/studio that could easily serve as a third bedroom, 2 full baths, soaring 10' ceilings, formal parlor with fireplace, library, and beautiful original heart pine craftsmanship throughout. An expansive 40' front porch, screened side porch, custom two-car garage, hand-dug well, natural gas, whole-house fan, large floored attic, and numerous original architectural details preserve the home's historic character. With its newly approved O&I zoning, historic significance, walkable downtown location, ample parking/garage space, and continued residential appeal, this one-of-a-kind property offers a rare opportunity to create a home, business, or uniquely flexible combination of the two in the heart of Pittsboro.

298 E Salisbury St, Pittsboro

142 Autumn Gate St, Pittsboro
$1,175,000
4 Beds ⋅ 4 Baths ⋅ 10134874 MLS ⋅ ACTIVE Status
Attractive Brick Accented Elevation w/Relaxing Sunny Sunrise Front Porch!! Inviting Spacious Entry Foyer w/Window Accented Sun Lit Staircase! Large Formal Dining Rm w/Extensive Trim Accenting & Lighted Glass Butler Pantry!! Gourmet Kitchen w/Large Island!! Stainless Steel Appliances!! Nice Food Pantry!! Breakfast Nook w/door to Screen Porch Over Looking Grilling & Chilling Patio!! Generous Family Rm w/Built-ins Accenting FP & 4 Panel Slider Overlooking Screen Porch!! Large Trayed Primary on Main w/Great View & Champagne Bath w/Relaxing Free Standing Tub & Zero Entry Shower & Double Vanities w/Tower Cabinet in Center w/ Direct Access to WIC w/Custom Shelving & Built-in Mirror w/Pocket Door to Nice Laundry Rm w/Sink and Folding Area & Upper Cabinets!! Inviting Sunlit Loft at Top of Stairs Ideal for Study Area!! 3 Generous Size Bedrooms w/Great WICs & Direct Full Bath Access!! HUGE BONUS RM w/Double Door Entry to Perfect Home Office & Fantastic Storage Area!! Truck Worthy Garage Depth!! Private Relaxing Screen Porch w/Patio Perfect for Entertaining!! Eco Select Plus Certification!! Natural Gas Heat/Logs/Cooktop & Tankless H2O!! Sealed Crawlspace!! Very Nicely Landscaped on One of The Quietest Streets in Chatham Park!! Park w/Splash Pad, Play Ground, Dog Park, & Covered Dining Area!! Brand New YMCA Built in 2025 w/2 Exterior Pools! 4 Soccer Fields Coming too!! Sidewalks on Both Sides of the Streets!! Major Medical Campus being Build!! Trails Galore through community with Access from Autumn Gate Street!! Retail right around the corner at the Mosaic!! The #1Visited State Park Lake Jordan Minute Away!!

142 Autumn Gate St, Pittsboro

473 Westhampton Dr, Pittsboro
$725,000
10080219 MLS ⋅ ACTIVE Status
LIVE ABOVE....ON BURNETTE MOUNTAIN IN CHATHAM COUNTY WITH FAR-REACHING VIEWS OF CHAPEL HILL This 6.7 Acre lot is near the TOP! Surpassing other luxury communities throughout Chatham, Orange, and Wake Counties. Home sites capable of accommodating some of the largest custom residences in the Triangle region, including the most sprawling ranch plans. Exceptional impervious surface allowances provide owners with the flexibility to create expansive outdoor living spaces, including pools, detached garages, guest houses, and accessory dwelling units. Two fiber-optic internet providers available within the community. Municipal water service eliminates the need for private wells, with fire hydrants conveniently located throughout the neighborhood. Home sites are permitted for 5+ bedroom luxury plans. No city taxes. Whether large or small, every home is built to the highest standards of luxury, craftsmanship, and quality.County water, natural gas, fiber optics ready in place! The Summit is an exclusive new home community Built by Sage Built Custom Homes, building legacy homes including many architectural styles and unlimited sizes, while located close to many of the Triangle-areas top destinations. This home-site is over 5 Acres near the elevation peak rising 600-feet above the community's gas lit entrance The Summit offers a land plan that allows its homes to be gently stair-stepped into the mountainside for stunning views of the surrounding Area! We have nearly 30 Home-sites to choose from with Rolling Wooded Sites overlooking a Mountain Stream as well as well as open sites sitting high above the street and sites overlooking the Meadow. Each home is custom built to compliment the chosen site and will always include meticulous landscaping, Irrigation and low voltage lighting the driveways and even the mailboxes. The entryway design includes meticulously maintained areas, painted brick walls which welcome you to a truly magnificent place to build any legacy home with unlimited size and architectural designs. Located in an Excellent School District, including the New 74-million-dollar Seaforth High School only 6 Minutes away! Easy drive to RDU, Raleigh Executive Jetport, UNC Hospitals, and Campus, as well as RTP. The New I-540 is very convenient to the newest portion of the outer loop providing easy access to I-40 towards the NC Coastal Areas and West Towards RDU and Durham.

473 Westhampton Dr, Pittsboro

372 Firefly Overlook Rd, Pittsboro
$2,150,000
5 Beds ⋅ 7 Baths ⋅ 10142171 MLS ⋅ ACTIVE Status
Your custom sanctuary in Firefly Overlook awaits. Discover the serenity and sophistication of Firefly Overlook at Jordan Lake—a premier new large-lot subdivision featuring just 30 exclusive homesites in the rapidly growing and highly desirable Chatham County. Perfectly positioned for effortless access to Apex, Pittsboro, Cary, and RDU Airport, this thoughtfully planned community places you moments from the pristine shores of Jordan Lake while offering a peaceful, nature-immersed retreat with rolling hills, panoramic views, and tranquil natural surroundings. This exceptional pre-sale opportunity on Lot 27—a beautifully central 1.55-acre homesite that enjoys prime visibility and prominence within the neighborhood—invites you to collaborate with renowned Triple A Homes to create your fully customized dream residence. The inspiring proposed design draws from Triple A Homes' award-winning plan, previously celebrated for its timeless elegance and innovative layout, and can be tailored entirely to your vision with personal selections, modifications, or unique enhancements. Envision this magnificent to-be-built custom home: a light-filled masterpiece featuring 5 luxurious bedrooms, including a serene primary suite and convenient main-level guest suite for ultimate comfort and privacy. The heart of the home is an expansive two-story great room with dramatic open-to-above volume, complemented by abundant oversized windows and large retractable doors that seamlessly blend indoor and outdoor living—flooding the spaces with natural light and creating the sensation of being enveloped by nature year-round. The gourmet designer kitchen flows into a dedicated scullery for effortless entertaining, while a bespoke wine cellar adds sophisticated charm. Step outside through the retractable doors to a spacious covered patio complete with a cozy fireplace—perfect for al fresco gatherings and quiet evenings under the stars. Lot 27's central location offers exceptional curb appeal and easy connection to the community's natural beauty, making your future home a standout landmark in this intimate enclave. Secure this rare central homesite today and partner with Triple A Homes to bring your personalized legacy residence to life. Construction timeline and customization details available upon inquiry.

372 Firefly Overlook Rd, Pittsboro

66 Romie Ct, Pittsboro
$1,095,000
5 Beds ⋅ 5 Baths ⋅ 10165584 MLS ⋅ ACTIVE Status
Now offered at $1,095,000: luxury living inside and an entertaining paradise outside, plus all the behind-the-scenes upgrades that allow function and beauty blend seamlessly. You won't want to miss the opportunity at this price! Now offered at $1,095,000: luxury living inside and an entertaining paradise outside, plus all the behind-the-scenes upgrades that allow function and beauty blend seamlessly. You won't want to miss the opportunity at this price! Tucked at the end of a quiet cul-de-sac in one of North Chatham's most coveted communities, 66 Romie Court (5 bedrooms, 4.5 baths) is the rare home that genuinely delivers on the promise of work-life balance without sacrificing a single luxury. Functional upgrades include a 24KW Generac whole-home generator, a whole-home reverse osmosis filtration system, an under-counter UV filtration tap, a robust Guardian home security system, a sealed crawlspace, a Rinnai tankless water heater, and hard-wired data ports throughout for seamless working, streaming, and gaming. Fresh interior paint and recessed lighting welcome you into a sunny, open downstairs floor plan designed for comfortable daily working, living, and effortless entertaining. The four-season room with large sliding glass doors off the main living area invites you to breathe deeply, slow down, and take in the wooded surroundings in every month of the year. A downstairs en-suite bedroom gives you a perfect place for guests or anyone who needs a more accessible space. Upstairs, a spacious primary suite with a second three-season room, brand new carpet, a soaking tub, and a huge walk-in closet echoes the calm of the space downstairs. Three additional upstairs bedrooms give everyone ample room to spread out. Head up to the third level for over 700 square feet of flex space to meet any need, including a built-in projector and sound bar for a luxe home entertainment experience. The 3-car garage and widened driveway make it easy to get in and out and provide tons of storage. When you're ready to get outdoors, head down to your 15'x30' deck-level pool, complete with a built-in stone grill, dining and lounge space, mature trees, and a privacy fence for total seclusion. Gardeners will love the bounty of 10+ mature blueberry bushes and two magnificent 30-foot "Fruit Cocktail" trees bearing plums, nectarines, peaches, and apricots throughout the year, and four raised garden beds with drip irrigation for easy, sustainable growing. With approximately 40 homes spread across 1+ acre lots, this North Chatham neighborhood offers the rare combination of true privacy and genuine community, all within easy reach of Chapel Hill, RTP, and growing downtown Pittsboro.

66 Romie Ct, Pittsboro

45 Quail Pt, Pittsboro
$1,299,950
4 Beds ⋅ 5 Baths ⋅ 10160405 MLS ⋅ ACTIVE Status
Grading is complete and permits are in place now is your chance to have your dream home overlooking Hole #2 of the highly sought-after Fred Couples Signature 18-hole golf course in the next 12 months. This thoughtfully designed 4,323 sqft home features an open and airy layout with 10 ft and 19 ft ceilings on the main level and 9 ft ceilings on the second floor, creating a bright and expansive feel throughout. The home offers 4 spacious bedrooms and 4.5 bathrooms, all secondary bedrooms are en-suite for ultimate comfort and privacy. The chef's kitchen is a true centerpiece, showcasing ceiling-height cabinetry, quartz countertops, stainless steel Bosch appliances, and a 36-inch gas range. A separate scullery kitchen adds both functionality and elegance. The kitchen flows seamlessly into the main living area, highlighted by a 48-inch gas fireplace and large sliding patio doors that open to a backyard with beautiful golf course views. Additional features include hardwood flooring throughout the main living areas, carpet in the bedrooms, and a tankless water heater for efficiency. A dedicated gym or media room and a spacious loft overlooking the main level provide flexible living and entertainment spaces. Situated on a private homesite, the property also includes a 3-car garage. Located in Chapel Ridge, residents enjoy resort-style amenities including a clubhouse, pool, fitness center, pickleball courts, tennis courts, volleyball, basketball, a soccer field, and, of course, championship golf.

45 Quail Pt, Pittsboro

17 Firefly Overlook, Pittsboro
$319,000
10164648 MLS ⋅ ACTIVE Status
Discover the serenity and sophistication of Firefly Overlook at Jordan Lake--a premier new large-lot subdivision in the rapidly growing and highly desirable Chatham County. This thoughtfully planned community is progressing beautifully, with 10+ homes already under construction by our Exclusive Builder Team and new residents beginning to call it home. Perfectly positioned at the intersection of N. Pea Ridge Rd and Seaforth Rd with direct access from HWY-64, Firefly Overlook delivers exceptional convenience to Apex, Pittsboro, Chapel Hill, Cary, and RDU Airport--while offering an effortless walk, bike ride, or golf-cart trip to nearby Vista Point Park, complete with boat launch, hiking trails, beach, and picnic areas. Within the community, residents enjoy a breathtaking mountain-like landscape of rolling hills, sweeping panoramic views, and peaceful natural creeks that create an unparalleled sense of escape. These inspiring homesites are designed for custom residences crafted by our distinguished Exclusive Builder Team: Hurst Home Company, Triple A Homes, Wagoner Homes, Poythress Construction, and Hearthstone Luxury Homes. Lot 1 presents a rare opportunity to establish the gateway to Firefly Overlook. As the premier showcase homesite at the front of the community, this expansive 1.57-acre parcel offers unmatched convenience and a commanding presence. Framed by mature hardwoods, the property extends back to a peaceful perennial stream and natural buffer, providing a beautiful balance of accessibility and natural tranquility. With preliminary house, well, and septic locations already thoughtfully mapped out, this picturesque lot is primed for construction. Its prominent positioning ensures your future custom residence will serve as a defining landmark of the neighborhood, setting the tone for the community that lies beyond. Secure this standout homesite now and collaborate with one of our exclusive builders to design the custom residence you've always envisioned. Contact us today for detailed maps, septic permit information, HOA guidelines, and available builder packages. Your legacy home in Firefly Overlook awaits.

17 Firefly Overlook, 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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