Pittsboro Homes with Chatham - Margaret B Pollard Middle School

Welcome to Pittsboro, North Carolina—a charming town nestled in the heart of Chatham County that beautifully blends small-town charm with modern conveniences. With its picturesque landscapes, friendly community, and rich history, Pittsboro is an ideal destination for families, retirees, and anyone looking to enjoy a vibrant lifestyle in a serene setting.

One of the standout features of Pittsboro is its strong commitment to education, highlighted by the presence of the esteemed Margaret B. Pollard Middle School. This institution is known for its dedicated faculty, innovative curriculum, and a welcoming atmosphere that fosters growth and learning. Families seeking homes in this area will find a community that prioritizes the educational needs of its children, making it a perfect choice for young families.

Pittsboro itself is a treasure trove of local attractions, from quaint shops and delightful eateries to scenic parks and recreational opportunities. The nearby Haw River offers a chance for outdoor enthusiasts to enjoy kayaking, fishing, and hiking, while the historic downtown area invites residents to explore its unique boutiques and farmer's markets.

With a variety of housing options available, from charming single-family homes to modern townhouses, Pittsboro provides something for everyone. Whether you are drawn to the vibrant community spirit or the beautiful landscapes that surround this lovely town, Pittsboro is ready to welcome you home. Experience the perfect blend of tranquility and community right here in Chatham County!

Newest Pittsboro Homes with Chatham - Margaret B Pollard Middle School

$520,000

3 Beds ⋅ 2 Baths ⋅ 10191548 MLS ⋅ ACTIVE Status

Imagine waking up to the tranquil sound of a gentle creek flowing just beyond your back door, sipping morning coffee from your sun-drenched dining space, and ending the day immersed in pure relaxation. Set in desired Fearrington Village, this turnkey retreat offers an elevated, low-maintenance lifestyle where you can easily stroll to village shops, seasonal markets, and enjoy all the vibrant community amenities, like the creekside walking trail right outside your door. Inside, natural light pours through expanded windows onto seamless LVP flooring and a cozy fireplace featuring a custom granite surround and live-edge mantel. The kitchen is designed for effortless living with granite countertops and instant hot water, while the primary suite serves as a true sanctuary with sliding barn doors, plantation shutters, and a spa-like bath with a corner jetted tub. Outdoor living is framed by nature—relax on the screened-in porch or entertain on the expansive Trex deck with custom privacy screening overlooking the woods. You will also love the rare, fully sealed walk-in lower level providing vast, clean, and dry storage space. Please see the complete list of major improvements in MLS docs, as there are too many upgrades to fit here! Don't just imagine this life—come feel the peace and fall in love with your new home today.

50 Trestle Leaf, Pittsboro

$819,000

4 Beds ⋅ 4 Baths ⋅ 10191393 MLS ⋅ ACTIVE Status

Meticulously maintained 4-bedroom home tucked away in a private wooded setting, encompassed by mature trees, situated on over 2 acres of secluded land. This property offers a perfect blend of convenience, peaceful countryside living, and modern comfort with a dynamic combination of indoor and outdoor living. As you walk through the front door you'll be greeted by an open family room featuring gas fireplace and surround sound speakers with a sitting/reading nook. Newly updated kitchen with new SS appliances, wall oven+microwave, 5-burner gas range with range hood, Corian countertops, custom pantries and cabinets, large breakfast nook, formal dining room, and access to sunroom with HVAC and surround sound speakers. Main level primary suite with vaulted 14' ceilings, gas fireplace, large custom closets, surround sound speakers, custom built-ins, Brazilian cherry hardwood floors, and gorgeous spa bath with huge frameless walk-in-shower, towel heater bar, and dual vanity. Laundry room with cabinets, counters, sink, and powder room completes the main level. Upstairs you'll find a 2nd primary suite with en-suite bath and huge WIC, 2 additional bedrooms and shared full bath with skylights. Walk out basement with large entertainment/rec room featuring surround sound speakers, pool table and bar. Rec room can be converted into 2-car garage. Basement also includes 1 car garage with custom shelving, workshop, exercise/storage room, and newly encapsulated crawlspace. Pool table and fridge in rec room + safe in workshop convey with the home. Incredible outdoor living! Expansive back deck and brick wraparound patio with outdoor grill and composite decking tops, 24 ft diameter 15,000 gallon pool with water slide and zipline, poolside shower with hot and cold water, pool house, and also plumbed for heated pool! 2 more outbuildings on the property, all hooked up with electricity. Charming front porch with swing. Other features include: expansive parking for RV, boats, cars, etc. Private well water with filter and upgraded 1-hp pump. Water iron remover tank in workshop. CPI alarm system. Dimmer lights throughout home. Situated on a high pitch/elevation for flood and rainwater aversion. All natural gas appliances. All additions are permitted. Freshly graveled driveway. New interior paint. Natural gas generator. Invisible fence. Irrigation system. Trail with bridge around the lot for walking or biking. This home is truly a retreat, don't miss your chance, schedule a showing today!

89 Lauren Ct, Pittsboro

$2,700,000

5 Beds ⋅ 7 Baths ⋅ 10191313 MLS ⋅ ACTIVE Status

This offering totals 26.71 acres across 4 combined parcels, with 2 developed residences, two septic systems, 1 shared well, and 2 buildable 3+ acre lots. From the moment you step inside, cathedral ceilings and floor-to-ceiling windows open every room to views of the land, so the changing seasons, deer moving through the meadow, and fireflies at dusk become part of everyday life rather than something you have to leave home to see. 319 Wrights Way (10.39 acres) is a 5,466 SF, 4-bedroom, 4.5-bath home, featured in NC Modernist Homes, engineered from eight inches of precast concrete, virtually indestructible, with passive solar design, radiant heated concrete floors, a wood stove, and a main-floor primary suite with forest and creek views. Custom cabinetry throughout was handcrafted by a local master woodworker, and details like reclaimed hardwood floors, stained glass, and recycled bottle-glass tile add warmth throughout, up to a lookout tower reached by a ship's hatch. The walkout level adds a media/game room, a gym with infrared sauna, and a creekside hot tub alcove. 321 Wrights Way (10.08 acres) adds a 1,655 SF guest residence backed by a verified five-year short-term rental history, with 1 bedroom, a spacious loft, and 1.5 baths, a four-car garage/workshop wired for a car lift, and a private office. Two additional buildable parcels (3.24 and 3 acres) round out the offering, ideal for a family compound or future income property; all four convey together. Nearly 1,600 feet of frontage runs along Terrell's Creek, with miles of wooded trails, a cleared meadow, a 4,000-square-foot fenced garden and chicken coop, daily sightings of deer, bunnies, and salamanders, and rarer visits from turkeys, turtles and even a black bear. A private drive keeps the setting quiet and secluded, minutes from Pittsboro, Chapel Hill/Carrboro, and Jordan Lake. Wrights Way is a rare kind of home, one you can live in every day and still admire like a piece of fine art. No picture does it justice. Schedule your private tour today.

319 Wrights Way, Pittsboro

$1,125,000

3 Beds ⋅ 3 Baths ⋅ 10191158 MLS ⋅ ACTIVE Status

This beautiful ''Henderson Farmhouse'' model is located on .98/acres in coveted Fearrington Village. Sliding glass doors open to the spacious screened porch overlooking the wooded and private back yard. The owner's suite, 2 guest rooms, and 2.5 baths are on the main level. Quartz counter tops and large island in the kitchen, upgraded appliances, beautiful open floor plan!The huge bonus room on the second level is ideal TV or game room! Over 1800 sq. ft. of walk-in, unfinished storage/attic space off second floor; walk-in closets, whole house generator and water filtration system, Plantation shutters, hardwood floors, Tankless hot water heater, sealed crawl space too! Professional landscaping completed in 2026. Carpeting and home professionally cleaned 9/2026.

4246 Henderson Pl, Pittsboro

$1,168,000

4 Beds ⋅ 3 Baths ⋅ 10191052 MLS ⋅ ACTIVE Status ⋅ Custom Build BLDG.

Privately positioned at the end of a quiet cul-de-sac beneath a mature wooded canopy, this exceptional custom home represents a rare opportunity to create a truly personalized luxury residence on four private acres within Pittsboro's intimate Fox Oak neighborhood. With construction beginning soon, there is a limited opportunity to reflect your personal tastes, in collaboration with this award-winning design/build custom builder. Inspired by timeless modern farmhouse architecture and elevated with sophisticated estate influences, the residence is thoughtfully designed for elegant entertaining and effortless everyday living, with beautifully proportioned living spaces filled with natural light. At the heart of the home, a 21'x17' Grand Room with 12' ceiling flows seamlessly into an impressive chef's kitchen with island and walk in pantry. The luxurious primary suite is designed as a serene private sanctuary, with a spa-inspired bath featuring dual vanities, soaking tub, walk-in shower, and his and custom walk-in closet with built-in wood shelving. Beyond the residence, the four-acre setting offers remarkable privacy and an extraordinary canvas for a private retreat. Set at the back of the cul de sac in Fox Oak, an established enclave of distinctive custom homes, this exceptional property combines the presence of an estate style setting with a short window to personalize your home as it comes to life. A rare opportunity to create something truly your own—where timeless architecture, exceptional craftsmanship, four private acres, and thoughtfully curated design come together in desirable Pittsboro.

97 Fox Oak Trl, Pittsboro

$645,000

2 Beds ⋅ 2 Baths ⋅ 10191033 MLS ⋅ ACTIVE Status

Timing is everything and you've hit the mark on this one! $40,000 in Upgrades & Improvements! FLEXIBLE FLOOR PLAN to suit your lifestyle -- whether it's 2/2 + office, 3/2 or 2/2 + dining room! This beautifully updated ONE-LEVEL home has the most amazing light bathing the space in sunshine. The high ceilings and casement windows offer a clear view to the wooded backyard and surrounding private cul-de-sac. NEW water heater, NEW furnace and AC. STAINLESS KITCHEN appliances - KitchenAid refrigerator and dishwasher, GE built-in wall oven, separate built-in microwave and electric cooktop on the kitchen island. Bathrooms were UPDATED with tiled flooring; Guest Bath now has a beautiful tub and handsome tiled surround. And, the Primary Bathroom has a WALK-IN TILED SHOWER with a bench. CUSTOM SHELVING in the walk-in kitchen pantry and primary closet. ENGINEERED HARDWOODS through most of the home with carpet in the primary closet. The BRICK-FLOORED SUNROOM is both heated and cooled for year-round use. It's the perfect space to have your morning coffee or entertain friends while you're grilling outside under the awning, enjoying your FENCED private backyard. 4055 Sampson is close to Fearrington Village center to enjoy all of the shops, restaurants and events going on. It's an easy walk to the park to visit with friends, have pizza at The Roost or listen to live music. Don't sleep on this one, it won't last long!

4055 Sampson, Pittsboro

$1,595,000

4 Beds ⋅ 5 Baths ⋅ 10190841 MLS ⋅ ACTIVE Status

Luxury awaits at 67 Rolling Woods Court! Set on a beautifully landscaped homesite in The Hamptons of Pittsboro, this highly amenitized custom home offers more than 4,000 square feet designed for comfortable everyday living and easy entertaining. Site-finished hardwoods, extensive trimwork and abundant natural light carry throughout the main level, where the spacious kitchen opens seamlessly to the dining and family rooms. A large center island, custom cabinetry and walk-in pantry make the kitchen as functional as it is inviting, while the family room's fireplace and built-ins create a natural gathering place. The main-level primary suite is a retreat of its own with a generous walk-in closet, dual vanities and zero-entry shower. A second main-level bedroom and full bath offer added flexibility for guests, an office or whatever life calls for next. An elevator provides convenient access between levels, where three additional bedrooms, a dedicated home theater, flex space and multiple walk-in closets provide plenty of room to spread out. Outside, the covered veranda with phantom screen and expansive patio with linear gas fireplace overlook a beautifully maintained backyard with space to gather, entertain and unwind. Every upgrade imaginable: whole home generator, sealed crawlspace, HVAC replaced in 2024 with dehumidifier, Moen smart auto-temp in primary shower, centralized surge protector, reverse osmosis water filtration, and the list goes on. A side-load three-car garage, and abundant storage complete this thoughtfully designed home, tucked into a peaceful Pittsboro setting with convenient access to Chapel Hill and Apex.

67 Rolling Woods Ct, Pittsboro

$849,500

4 Beds ⋅ 4 Baths ⋅ 10190765 MLS ⋅ ACTIVE Status

Set on more than two wooded acres, this custom-built home offers privacy and quality finishes at every turn. Fresh interior paint and new carpet complement the home's already-rich hardwood floors, detailed trim, and crown molding. The kitchen anchors the main floor w/ stainless appliances, granite counters, custom cabinetry, a center island with bar seating, spacious pantry, and a breakfast nook that catches the morning sun. A see-through gas fireplace opens the kitchen and breakfast area to the two-story family room, where a wall of windows keeps the whole space bright. The dining room and living room/office add flexibility to this level. A guest bedroom and full bath round out the first floor, along with a laundry room w/ cabinets, utility sink, and tile floors. Upstairs, the owner's suite has hardwood floors, crown molding, a walk-in closet with custom shelving, and a bath with a double vanity, jetted tub, walk-in shower, and separate water closet. Bedrooms three and four share a Jack-and-Jill bath with two vanities; bedroom five has its own walk-in closet and direct access to the hall bath. The third floor adds a bonus room with two closets and access to floored attic storage. The backyard oasis has a large deck, stone patio, and gazebo tucked into the trees. Behind the property, an additional 2.7 acres of HOA-owned open space includes a 1.5-2 mile trail, reachable from the garden at the top of the yard. This one-owner home has been well-cared for and now move-in ready. Downtown Pittsboro, Chapel Hill, and Jordan Lake are all a short drive away!

93 Wild Rose Ln, Pittsboro

$685,000

4 Beds ⋅ 4 Baths ⋅ 10190411 MLS ⋅ ACTIVE Status ⋅ Alpha Omega Homes BLDG.

3 Private Acres + Attached Apartment — Minutes from Carrboro Set on 3 private, wooded acres just minutes from Carrboro, this spacious home offers an unusual combination of privacy, versatility, and potential. One of its most significant features is the attached apartment, providing a separate living space that greatly expands the ways this property can be used. Whether for extended family, multigenerational living, adult children, long-term guests, a caregiver, or a private work-from-home arrangement, this additional space adds tremendous flexibility and value to the property. The main home offers generous living areas, hardwood flooring, abundant natural light, and plenty of room to create something special. The kitchen, baths, and some finishes are dated, and rather than completing renovations simply to bring the property to market, the seller has chosen to offer the home as-is and price it accordingly. That creates an opportunity for the next owner to invest in the improvements they want and choose their own finishes, rather than paying a premium for someone else's renovations. The pricing has been positioned with those anticipated improvements in mind, allowing a buyer to update and personalize the home while keeping their overall investment more in line with other homes in the community. Outside, mature trees surround the home, creating a peaceful and private setting across approximately 3 acres. An attached two-car garage provides convenient parking and storage, while the location offers the best of both worlds—a wooded, tucked-away setting with Carrboro and Chapel Hill just minutes away. The exterior was originally Masonite siding, with the front elevation replaced with fiber-cement siding. For a buyer who needs more than just a traditional single-family home, the combination of acreage, privacy, an attached apartment, generous living space, and the ability to renovate to their own taste makes this property a particularly compelling opportunity.

475 Deer Mountain Rd, Pittsboro

$225,000

2 Beds ⋅ 1 Baths ⋅ 10190403 MLS ⋅ ACTIVE Status

This charming end-unit offers a hard-to-find combination of privacy, character, convenience, and low-maintenance living at an affordable price in booming Chatham County! Enjoy an open floor plan with vaulted ceilings, abundant natural light, and fresh interior paint. The ranch-style layout provides easy one-level living. The spacious primary bedroom features an expansive walk-in closet. Unique details like stained glass, ceramic knobs, and custom hardware add warmth and character to the home. Outside, low-maintenance features include a metal roof, vinyl siding, encapsulated crawlspace, private gravel driveway, and recently refinished patio. Surrounded by 4+ acres of HOA maintained greenspace, the property feels like a private wooded oasis and lives much more like a single-family home than a traditional townhome or condo. Conveniently located along Manns Chapel Road near popular Briar Chapel and with direct access to Chapel Hill and Pittsboro, this unique property is ideally positioned in one of the Triangle's fastest growing areas. Whether you are looking for a primary residence, downsizing opportunity, or easy-to-maintain investment, this property offers an exceptional combination of privacy, location, and value. See Documents for a complete list of recent upgrades and improvements. See Documents for a complete list of recent upgrades and improvements.

82 Mannsfield Crescent Way, Pittsboro

$185,000

2 Beds ⋅ 1 Baths ⋅ 10190355 MLS ⋅ ACTIVE Status

Move in Ready One level living, Vaulted Ceilings, New LVP flooring thru out, Freshly Painted, New Heat Pump-6/2026, Quartz counters, Charming home convenient to Chapel Hill & Pittsboro! Mannsfield Condo community has about 8 buildings each with 2 units. HOA is managed by the homeowners. Each building has its own septic system and there is a shared well - no water/sewer bill. Don't miss this affordable home on a quiet cul-de-sac. Reasonable HOA monthly dues $150/monthly. Call listing agent with any questions.

85 B Mannsfield Crescent Way Unit B, Pittsboro

$399,999

2 Beds ⋅ 2 Baths ⋅ 10190275 MLS ⋅ ACTIVE Status

Welcome to this beautifully renovated jewel box in the heart of desirable Fearrington Village. Thoughtfully updated and move in ready, this charming home offers the ease of one floor living with two bedrooms conveniently located on the main level. The renovated kitchen shines with new quartz countertops, while the updated bathrooms feature coordinating quartz surfaces and fresh, modern finishes. New LVP flooring and new carpet add to the crisp, updated feel throughout the home. Enjoy the distinctive lifestyle that makes Fearrington Village so special, with its picturesque walking trails, beautiful green spaces, shops, dining, community activities, and the charm of Fearrington Village Center just moments away. A wonderful combination of style, comfort, convenience, and location, this is truly a jewel box you will not want to miss.

482 Beechmast, 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 .