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36 Rosefield Ct, Pittsboro
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 10161024 MLS ⋅ ACTIVE Status
A rare opportunity awaits in the exclusive Estates at Chapel Ridge. This distinguished Prewitt-Douglas custom home sits on nearly an acre -- one of the last remaining lots in this coveted enclave. Spanning over 3,500 square feet, the residence showcases high-end finishes throughout and a desirable main-level primary suite complete with dual walk-in closets. Four bedrooms and 3.5 baths offer ample space for comfortable everyday living and effortless entertaining. Residents enjoy access to Chapel Ridge's full suite of community amenities, providing year-round recreation for the entire family. Exceptional craftsmanship, a premier lot, and an unmatched location -- opportunities like this are few and far between.

36 Rosefield Ct, Pittsboro

55 Bob White, Pittsboro
$859,000
4 Beds ⋅ 4 Baths ⋅ 10146367 MLS ⋅ ACTIVE Status
Welcome to this beautifully appointed home in Chapel Ridge, part of the highly desirable Chatham Park community in Pittsboro. With an acceptable offer, the seller is offering up to $8,000 toward buyer closing costs, creating an exciting opportunity to make this exceptional home yours. Designed with both everyday comfort and entertaining in mind, this home features a thoughtful floor plan and elevated finishes throughout. The designer kitchen offers abundant cabinetry, premium appliances, and a spacious walk-in pantry, while the adjoining breakfast area flows effortlessly to the covered, screened-in porch for easy indoor-outdoor living. A separate formal dining room with a coffered ceiling provides an elegant space for hosting and special occasions. The main-level primary suite is a true retreat, featuring a generous walk-in closet with convenient direct access to the laundry room, complete with a utility sink. The spa-inspired en-suite bath includes a freestanding soaking tub, separate walk-in shower, and plenty of space to unwind. A dedicated powder room completes the main level. Upstairs, you'll find three additional bedrooms, a spacious bonus room, and a versatile loft—ideal for guests, a home office, playroom, media space, or additional living area. Additional features include a three-car garage and a sealed, temperature-controlled crawlspace offering exceptional storage and future possibilities. Enjoy the lifestyle that makes this location so special. Chapel Ridge offers resort-style amenities including a Fred Couples Signature golf course, clubhouse with dining, pro shop, swimming pool, fitness center, tennis and pickleball courts, walking trails, playgrounds, picnic areas, and community gathering spaces. Nearby Chatham Park adds even more opportunities for parks, trails, recreation, shopping, dining, community events, and green space, all with convenient access to downtown Pittsboro, Jordan Lake, Raleigh, and Durham.

55 Bob White, Pittsboro

154 Colonial Trail Ct, Pittsboro
$1,160,000
4 Beds ⋅ 4 Baths ⋅ 10160679 MLS ⋅ ACTIVE Status
Discover this beautifully crafted luxury custom home, built by an award-winning builder. Offering a thoughtfully designed layout and quality finishes throughout. The main level features a spacious primary bedroom suite along with an additional bedroom and full bath, providing flexible living arrangements. A dedicated study offers a private workspace or quiet retreat. The open living areas connect seamlessly to an outdoor deck and screened-in porch, creating inviting spaces for everyday living and entertaining. Upstairs, you'll find two additional bedrooms, each with access to a full bath, along with a large recreation room and separate media room. A substantial walk-in storage area provides ample space for organization. Located within a golf community, residents have access plentiful amenities to include a pool with water slide, fitness center, clubhouse, sports courts, and playground. For association documents please visit https://www.casnc.com/communities/chapel-ridge-community/

154 Colonial Trail Ct, Pittsboro

115 Circle City Way, Pittsboro
$629,000
4 Beds ⋅ 4 Baths ⋅ 10145757 MLS ⋅ ACTIVE Status
New Large Price Improvement! Up to $6000 in lender paid closing costs or use to buy down the rate! Now the lowest dollar per sq ft single family home in Chatham Park, don't miss this opportunity! With its designer upgrades, beautiful backdrop and yard, custom details and in like-new condition, you can't go wrong. Having a recent large price adjustment, this pristine home won't last much longer! This like-new 2024 built home is both stunning and thoughtfully designed! Spacious with lots of storage and great views. This 4-bedroom, 3 and a half bath home is situated on a lot with a beautiful view and privacy. It offers both exceptional functionality and luxurious finishes throughout, showcasing an upgraded design. The flexible floor plan includes a main-level primary bedroom with an upgraded luxury bathroom. Also on the main level you will find a study, dedicated office nook, large dining area, half bath and spacious kitchen. Upstairs are 3 more bedrooms, 2 full bathrooms, 2 large walk-in storage rooms, and a large bonus room providing additional living or recreational space. The gourmet kitchen is well appointed with granite countertops, stainless steel appliances, under-sink reverse osmosis system, upgraded lighting and a large pantry, Additional custom trim work is featured within the home highlighting the high-end design. Situated on a beautiful lot, the outdoor spaces include a large deck, and screened-in porch, perfect to take in the view of the park, and further outdoor enjoyment. Situated to enjoy your sunrise view with your morning coffee! Even the crawlspace is conditioned and sealed for peace of mind. Located in Chatham Park, the community offers access to nature trails, parks, splash pad, dog park, and option to join the private swimming pool and pickleball courts. This beautiful home is located in close proximity to trails and the new YMCA. Custom features, great location, and the privacy to enjoy your beautiful home are just some of the key features.

115 Circle City Way, Pittsboro

92 Margaret Mann Way, Pittsboro
$800,000
4 Beds ⋅ 3 Baths ⋅ 10161964 MLS ⋅ ACTIVE Status
Completely Renovated, Move-In Ready, and Select Furnishings Available, this exceptional custom home offers a rare turnkey opportunity in the highly sought-after Manns Crossing community of Chatham County with no city taxes. Nestled on 1.2 beautifully landscaped acres just minutes from Chapel Hill, Pittsboro, Jordan Lake, and the thriving Chatham Park corridor, the sellers have invested approximately $300,000 in improvements, including more than $200,000 in interior renovations and over $100,000 in exterior enhancements and professional landscaping, creating a property that combines luxury, privacy, convenience, and effortless living. Thoughtfully designed for everyday living and entertaining, the home features desirable main-level living with three first-floor bedrooms, including a luxurious primary suite. A private upstairs guest suite with a fourth bedroom, full bath, and walk-in closet offers ideal space for guests, a home office, or multigenerational living. Sun-filled living spaces showcase hardwood floors, plantation shutters, extensive crown molding, exceptional millwork, and designer finishes throughout. The beautifully renovated gourmet kitchen features custom Integrity cabinetry, quartz countertops, a spacious center island, stainless steel appliances, and a 36-inch Café range. The adjoining family room centers around a striking German smear brick fireplace, while the inviting sunroom overlooks the breathtaking backyard retreat. The luxurious primary suite provides a spa-like escape with a freestanding soaking tub, custom-tiled walk-in shower, and thoughtfully designed custom closet. Step outside and discover your own private resort. Designed for year-round enjoyment, the outdoor living spaces include a screened porch, Trex deck, outdoor stone fireplace, stamped concrete patio, pergola, and professionally landscaped grounds surrounded by mature plantings for exceptional privacy. The fenced backyard offers additional usable land beyond the fence line and provides ample room for a future pool, further enhancing this extraordinary outdoor setting. Despite its 2,508 square feet, the home's thoughtful layout, expansive entertaining areas, private guest suite, and seamless indoor-outdoor flow allow it to live much larger than its size would suggest. Additional upgrades include a new roof, whole-house generator, renovated laundry room with custom cabinetry, custom garage doors, a fully organized garage with built-in cabinetry and Husky storage system, an encapsulated crawl space with standing storage, a premium Tuff Shed, and handcrafted solid wood front doors by Carolina Doors. Whether relocating to the area, searching for a luxury primary residence, or seeking an elegant retreat near Chapel Hill, Jordan Lake, and Chatham Park, this exceptional property offers a unique combination of craftsmanship, comfort, privacy, and value in one of Chatham County's most desirable communities.

92 Margaret Mann Way, Pittsboro

114 Mountaintop Cir, Pittsboro
$7,689,900
5 Beds ⋅ 8 Baths ⋅ 10112060 MLS ⋅ ACTIVE Status ⋅ Overlook BLDG.
Welcome to the Overlook! This is Sage Built's most recent masterpiece show home ready for construction. A modern style home with true vistas of the surrounding nature. A Grand entry with covered porch welcomes you to the soaring foyer area and library. A chef inspired kitchen with 21' scullery opens to the family room and a 36' x 15' porch separated by a dual set of sliding glass doors. The screened deck features a motorized phantom screening system. The main level living includes an ensuite / guest haven with designer closet and fully equipped bath with shower. Walk up or travel by elevator to the second-floor lounge with access to the star gazing deck and grand suite terrace. The grand suite is 21' x 18' and features his and hers closets including the LG styler steam closet, a spa inspired Bath and networking room. Also enjoy access to the grand suite terrace with sliding doors. But wait...there is a private sunbathing balcony accessed through the spa! Across the hall you will find a generously appointed ensuite 3 and 4 each with full bath and easy access to the second laundry area. The entertainment mecca is located in the lower level featuring a bedroom with the 20 x 12 Au pair suite. Across the hall is the laundry/gift wrapping craft room as well as the exercise yoga studio with sports storage, sauna and locker room with shower. The main attraction to the lower level is the theater room and game areas serviced by a kitchen area and separate wine/cigar room. All of this has easy access to the 36' x 15' phantom screened porch and the oversized sunrise deck. Step off the sunrise deck to the infinity pool and outdoor living spaces. Lastly you will of course be thrilled with an oversized 3 car garage with dog washing station and EV charging. Come see this amazing home site of nearly two acres and personalize this custom one of a kind original plan and legacy home available only by Sage Built and the Summit Community located here overlooking beautiful Chatham County NC.

114 Mountaintop Cir, Pittsboro

20 Canvasback Ct, Pittsboro
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 10147914 MLS ⋅ ACTIVE Status
Stunning New Basement Home in Chapel Ridge. Welcome to luxury living in the highly sought-after Chapel Ridge community. Builder offering $25,000 in closing costs or to use on a rate buy-down. This exceptional home makes a statement from the moment you walk in, featuring dramatic cypress beams in the family room and soaring floor-to-ceiling windows that flood the space with natural light. Built by Capstone Builders, renowned for their exquisite craftsman trim work and attention to detail, this home is thoughtfully designed with upscale finishes throughout. The chef's kitchen offers abundant cabinetry, a beautifully appointed walk-in pantry, and a layout ideal for both everyday living and entertaining. The primary suite is truly a retreat, showcasing a spacious spa-like shower and an impressive walk-in closet that must be seen in person. A private main-floor office with French doors provides the perfect work-from-home space. Upstairs, you'll find three generously sized bedrooms, two full bathrooms, and a large loft area ideal for a media room, playroom, or second living space. The stylish drop zone and well-designed laundry room add both convenience and charm. Designed for entertaining, the home includes a surround sound system and double rear deck porches perfect for enjoying the outdoors. The full unfinished basement offers even more potential, already framed with plumbing roughed in--ready for you to complete with your vision. Located in the prestigious Chapel Ridge community, residents enjoy resort-style amenities including a Fred Couples-designed golf course, swimming pool, lighted tennis and basketball courts, fitness center, restaurant and bar, and beach volleyball. Live where every day feels like a getaway.

20 Canvasback Ct, Pittsboro

967 Bynum Rd, Pittsboro
$695,000
4 Beds ⋅ 2 Baths ⋅ 10093658 MLS ⋅ ACTIVE Status ⋅ The Snipes House BLDG.
This charming 4-bedroom, 2 bath home beautifully blends historic allure with contemporary updates. This delightful home boasts beautiful heart pine floors, stunning bead board accents, multiple fireplaces, custom cabinetry, & an array of additional features. Nestled in the delightful Bynum area, this property is a popular Air B&B. The general store/museum across the street offers live music on Friday evenings May to September & additional events. ''The Snipes House'' built in 1908, offers generous outdoor space with a one-acre lot, perfect for enjoying the great outdoors. Let this be your perfect family home or your next great investment. (This is a beautiful historic house. The square footage listed at 2460 does not include the delightful and useful 2nd floor flex room that is 399 square feet due to a partially low ceiling height. The useful, livable square footage of the home is 2859 sf. )

967 Bynum Rd, Pittsboro

304 Wrights Way, Pittsboro
$675,000
4 Beds ⋅ 3 Baths ⋅ 10165183 MLS ⋅ ACTIVE Status
Complete privacy in highly sought-after North Chatham, where peace and tranquility define everyday living--yet you're just a short drive to Pittsboro, Carrboro, Chapel Hill, and Chatham Park. Designed to embrace its serene surroundings, the home offers exceptional outdoor living with a welcoming wraparound porch and a spacious screened porch--perfect for relaxing, entertaining, and taking in the natural beauty. Inside, enjoy convenient main-level living with two bedrooms and a dedicated office on the first floor, all complemented by an open-concept layout filled with natural light. Upstairs, you'll find two generously sized bedrooms with large closets, along with abundant storage throughout the home. The expansive property provides ample opportunity to customize, with plenty of space to add a garage, workshop, or additional outbuildings. A rare combination of privacy, flexibility, and proximity--this is North Chatham living at its finest.

304 Wrights Way, Pittsboro

2310 Jones Ferry Rd, Pittsboro
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 10152729 MLS ⋅ ACTIVE Status
PROPOSED NEW CONSTRUCTION Your private sanctuary awaits! Imagine waking up every morning surrounded by towering trees and the soothing sounds of nature on your very own 3 acre retreat. This is country living at its finest, and it is closer than you think, just 9 miles from Chapel Hill with easy access to vibrant dining, shopping, cultural events, live music, and university sports in Chapel Hill, Carrboro, Chatham Park, and downtown Pittsboro. No HOA, no restrictions, just the freedom to bring your dream home to life exactly the way you envision it! Make that dream a reality with Paragon Custom Homes, proudly selected as the Triangle's builder member in the exclusive Southern Living Custom Builder Network. This prestigious program brings together a select group of highly respected builders across the South, recognized for exceptional craftsmanship and thoughtful design that reflects the timeless character of Southern living. Paragon is known for incorporating Adaptive Design principles, creating homes that are elegant, intuitive, and thoughtfully designed to support the way you live today and for every season of life that follows. Two adjacent lots are also available, offering the rare opportunity to create a private family compound or secluded retreat. This is more than a homesite. It is the beginning of a home designed to serve you beautifully for a lifetime. This is Quality for Life.''

2310 Jones Ferry Rd, Pittsboro

2354 Jones Ferry Rd, Pittsboro
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 10152743 MLS ⋅ ACTIVE Status
Your private sanctuary awaits on this wooded 3-acre retreat, just 9 miles from Chapel Hill. Enjoy the peace of country living with quick access to dining, shopping, cultural events, live music, and university sports in Chapel Hill, Carrboro, Chatham Park, and downtown Pittsboro. With no HOA and no restrictions, you have the freedom to design the home and lifestyle you truly want. Make that dream a reality with Paragon Custom Homes, proudly selected as the Triangle's builder member in the exclusive Southern Living Custom Builder Network. This prestigious program brings together a select group of highly respected builders across the South, recognized for exceptional craftsmanship and thoughtful design that reflects the timeless character of Southern living. Paragon is known for incorporating Adaptive Design principles, creating homes that are elegant, intuitive, and thoughtfully designed to support the way you live today and for every season of life that follows. Two adjacent lots are also available, offering the rare opportunity to create a private family compound or secluded retreat. This is more than a homesite. It is the beginning of a home designed to serve you beautifully for a lifetime. This is Quality for Life.''

2354 Jones Ferry Rd, 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

191 High Ridge Ln, Pittsboro
$955,000
4 Beds ⋅ 4 Baths ⋅ 10132755 MLS ⋅ ACTIVE Status
Exceptional custom home in the sought-after Chapel Ridge community. This thoughtfully designed 4 bedroom, 4 bath residence offers an ideal layout with a main-level primary suite and secondary bedroom, perfect for single-level convenience. The open-concept living area flows seamlessly into a beautifully appointed kitchen, creating an inviting space for everyday living and entertaining. Upstairs, two additional bedrooms each feature private en suite baths, while a bonus room and flexible flex space provide endless possibilities for work, play, or relaxation. All of this set within Chapel Ridge -- a premier community offering resort-style amenities just moments from your door. A rare combination of thoughtful design, quality craftsmanship, and an unmatched lifestyle.

191 High Ridge Ln, 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

81 Loggers Run, Pittsboro
$1,195,000
4 Beds ⋅ 5 Baths ⋅ 10166299 MLS ⋅ ACTIVE Status ⋅ Brighton BLDG.
Homes By Dickerson is building the Brighton in Corbett Landing, ideally situated on a coveted cul-de-sac lot adjacent to a neighborhood pocket park. This custom luxury home features a main-level primary suite and study, along with a powder room and laundry room with sink. The second floor offers three bedrooms, three full bathrooms, and a spacious rec room. The main living areas showcase a vaulted kitchen and dining space with exposed beams, opening to a screened porch with fireplace. Thoughtful details include custom trim work in the study, built-in bookcases flanking the family room fireplace, and a scullery complete with base and wall cabinetry, sink, and beverage refrigerator. Additional highlights include lockers in the owner's entry, designer wallpaper in the powder room, and hard surface flooring throughout the main level. The home is finished with custom features throughout and a fully landscaped yard with irrigation.

81 Loggers Run, 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

154 Birdie Ct, Pittsboro
$625,000
3 Beds ⋅ 3 Baths ⋅ 10162363 MLS ⋅ ACTIVE Status
Welcome to this beautifully maintained custom home nestled on the golf course in the sought-after Chapel Ridge community in Pittsboro. Perfectly situated on a quiet cul-de-sac within the renowned Chapel Ridge Golf Club--a Fred Couples-designed course--this home offers both tranquility, scenic views and accessibility. Designed for easy single-level living, all bedrooms are conveniently located on the main floor. The open-concept layout is filled with natural light and spacious living area, and a large kitchen perfect for entertaining. An office area provides the ideal work-from-home space, while the expansive upstairs bonus room with a half bath offers endless possibilities for a media room, guest retreat, or playroom. Additional highlights include a two-car garage, abundant storage throughout, and conveniently located near downtown Pittsboro, with easy access to Chapel Hill, Apex, and Raleigh, Enjoy resort-style living with neighborhood amenities such as a pool, pickleball courts, tennis courts, and fitness center--all just steps from your door. This is golf course living at its finest--peaceful, private, and move-in ready!

154 Birdie Ct, 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

431 Fieldstone Ln, Pittsboro
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 10079735 MLS ⋅ ACTIVE Status
Build your new custom home in the established and sought after neighborhood of Fieldstone located minutes from Chapel Hill/Carrboro and Pittsboro. Build this plan, one of the builder's other plans or bring your own! This floorplan features the primary suite on the main level along with his and hers closets, family room with gas fireplace and access to the screened porch, study with access to the large front porch, eat in kitchen with pantry, sunroom, mud room and laundry. Upstairs are three additional bedrooms each with access to a full bath. The sizeable loft is perfect for a bonus room. With a flexible floorplan many options exist. The study on the main floor adjoining the half bath could be converted to a second bedroom with a fullbath. The sunroom could be used as a breakfast room or office. The unfinished attic could be partially or fully finished for more living area - second bonus room, gym, office space, etc. Possibilities are endless!

431 Fieldstone Ln, Pittsboro

60 Willow Creek Ct, Pittsboro
$1,595,000
4 Beds ⋅ 4 Baths ⋅ 10160197 MLS ⋅ ACTIVE Status
This stunning Prewitt-Douglas Custom Homes 2026 Parade Home offers over 4,000 square feet of luxurious living space on a picturesque 1.5-acre lot in the gated community of Chapel Ridge Estates. Elegant design and extensive trim work create a distinctive backdrop for everyday living and memorable entertaining. Four spacious bedrooms and 3½ baths provide room to unwind, while the inviting hearth room offers a comfortable gathering space. A hidden pantry and scullery bring thoughtful functionality to the kitchen, keeping preparation and storage conveniently tucked away. An outdoor kitchen extends the entertaining possibilities, and a three-car garage completes this exceptional home. Experience custom craftsmanship, refined details, and generous living spaces in a beautiful Pittsboro setting.

60 Willow Creek Ct, Pittsboro

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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