Refine Search
Map
Sort by
$419,500
3 Beds ⋅ 3 Baths ⋅ 10191853 MLS ⋅ ACTIVE Status
Welcome to 299 Millennium Drive, a pristine 3-year-old townhouse in the highly sought-after Chatham Park community of Pittsboro, NC. Offered at the incredible price of $419,500, this home has been lovingly cared for, offering a turn-key, like-new living experience with premier upgrades and total convenience. Home Highlights & Custom Upgrades Move-In Ready Quality: Meticulously maintained 3-year-old construction with a walk-in pantry, epoxy-finished garage floor, and an active HVAC maintenance agreement for total peace of mind. EV-Ready Garage: Equipped with an outlet in the garage ready for your electric vehicle charger. Private Outdoor Retreat: Features a backyard and a side privacy fence that backs up to peaceful, serene woods. Enjoy quiet forest views from your screened-in back porch, plus plenty of room for pets to exercise. Location & Community Chatham Park Amenities: Situated in Chatham Park, giving you instant access to all the vibrant entertainment, parks, and events the development has to offer. Active Lifestyle: Located near Paddles Swim and Pickleball Club! Unbeatable Convenience: Tucked away in a private, quiet neighborhood while remaining convenient to Hwy 64 and just minutes from local restaurants, shopping, and charming downtown Pittsboro.

299 Millennium Dr, Pittsboro
$535,000
3 Beds ⋅ 3 Baths ⋅ 10191826 MLS ⋅ ACTIVE Status
BETTER THAN NEW HOME FOR SALE IN CHATHAM PARK! Built in 2022 by David Weekley Homes, and meticulously maintained by the original owners, this pet-free, smoke-free 3BR/2.5BA home offers an exceptional combination of modern efficiency, natural light and Chatham Park greenway living. The open-concept main level features a spacious kitchen flowing into the dining and living areas, plus a dedicated office/flex space. Upstairs, a generous loft provides a second living area surrounded by all 3 bedrooms. Relax on the covered rear porch overlooking the greenway and paved walking trail or enjoy the large covered front porch in this highly walkable Pittsboro community. Upgrades include a Kinetico K5 water filtration system with reverse osmosis, tankless gas water heater, encapsulated crawl space, whole-home surge protector, extended HVAC warranty and excellent garage storage. Remaining portion of the 10-year builder structural warranty conveys. ENERGY STAR®, EcoSelect Plus and Environments for Living® certified. Enjoy Chatham Park swimming, pickleball and trails, with Thales Academy within walking distance. Minutes to Jordan Lake for boating, hiking, fishing and camping and approximately 30 minutes to RDU International Airport and the Research Triangle. Why wait to build? Start enjoying the Chatham Park lifestyle in Pittsboro, NC today!

261 Mindees Ln, Pittsboro
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 10191808 MLS ⋅ ACTIVE Status
Welcome to 226 Evington Drive, an extraordinary custom property set on 2.3 acres in Riverstone Estates, one of Chatham County's most distinguished luxury communities, backing to protected North Carolina State Park land. This one-owner residence offers exceptional privacy, a serene natural backdrop and convenient access to Jordan Lake, Wake County, UNC-Chapel Hill, Duke and RDU International Airport. Originally built by Sadler Construction, the home makes a striking first impression with its timeless white-brick exterior, dark-framed windows and professionally designed grounds. Inside, 10-foot ceilings, site-finished white oak floors, white oak trim, extensive custom millwork, architectural arches, ceiling beams, specialty cabinetry and upgraded Emtek hardware reflect an extraordinary level of craftsmanship. Thoughtful universal-design features including wide passageways, zero-entry main-level living and garage access, accessible baths and planning for a future elevator allow the home to live beautifully through every season of life. At its heart, the chef's kitchen showcases custom Harrison Vintson cabinetry, quartz countertops and backsplash, a full Thermador appliance package, XO wine refrigeration, integrated wine storage and a hand-finished plaster range hood designed to coordinate with the living room fireplace. A beautifully appointed butler's pass-through and thoughtfully designed cabinetry make entertaining effortless. The living room is equally compelling, featuring a custom plaster fireplace, white oak built-ins, Dekton surfaces and integrated color-changing lighting. Oversized sliding doors reveal the home's signature indoor-outdoor sightline, extending from the living room to the vaulted screened porch, where continuing ceiling beams and warm cedar detailing create a seamless architectural connection. Two bedrooms are conveniently located on the main level, including a private guest suite with its own exterior entrance and en suite bath, ideal for multigenerational living, extended-stay guests or an au pair. The primary suite features remote-controlled Lutron shades, custom built-ins and a spa-inspired bath wrapped in floor-to-ceiling marble tile. Remote-controlled Phantom screens open to a private resort-style backyard anchored by a 40-by-20-foot saltwater pool with a tanning ledge, approximately seven-foot depth and app-controlled lighting. Electrical infrastructure is already in place for a future pool heater. A white-brick outdoor gas fireplace, custom patio flooring, generous lounging areas and an upper-level Trex deck overlooking the pool provide exceptional spaces for gathering, entertaining and relaxing. Approximately $150,000 in professionally designed landscaping surrounds the residence with remarkable beauty. Bermuda grass, drip irrigation, extensive landscape lighting, mature ornamental trees and layered flowering gardens create the atmosphere of a secluded retreat. Iron fencing, a fully enclosed backyard and the protected wooded backdrop provide a degree of privacy rarely found this close to the Triangle's major destinations. Additional highlights include a beautifully designed mudroom, an exceptionally appointed laundry room with an upstairs laundry chute, a playroom or flex space, professional-grade gym flooring, walk-in closets, abundant attic storage, a water softener, epoxy-finished garage floors, built-in garage storage, upgraded heavy-duty garage doors and electric-vehicle charging. 226 Evington Drive presents a rare opportunity to own a private Pittsboro luxury estate where architectural distinction, thoughtful accessibility, resort-caliber outdoor living and effortless Triangle connectivity come together.

226 Evington Dr, Pittsboro
$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
$639,500
2 Beds ⋅ 2 Baths ⋅ 10191033 MLS ⋅ ACTIVE Status
Timing is everything and you've hit the mark on this one! PRICED TO SELL --- $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
$545,000
4 Beds ⋅ 4 Baths ⋅ 10190524 MLS ⋅ ACTIVE Status
Welcome to easy living in the heart of Chatham Park, where a thoughtful floor plan, modern finishes, and inviting indoor-outdoor spaces come together beautifully. And the best part? It's practically brand new—so what could be better? The highly sought-after primary suite on the main level makes everyday living comfortable and convenient, while the open-concept kitchen, dining, and living areas create an easy flow for both everyday life and entertaining. Step outside to the screened-in porch, the perfect spot for morning coffee, dinner outside, or winding down at the end of the day. Upstairs, three additional bedrooms offer plenty of flexibility for family, guests, a home office, or whatever fits your lifestyle. With a two-car garage, a fantastic layout, and newer construction, you get all the benefits of a nearly new home without the wait of building from the ground up. Located in Chatham Park, one of Pittsboro's most exciting communities, you'll have trails, green spaces, community amenities, and everything that makes this growing area so special right at your fingertips. Primary down, three bedrooms up, a screened porch, and practically brand-new construction—this one checks all the boxes!

221 Beacon Dr, 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
$299,000
10190170 MLS ⋅ ACTIVE Status
Incredible vacant land opportunity in Chatham Co. Accessed by well maintained private road, this 8.417 acres of beautifully wooded rolling terrain can be your new homestead, mini farm, multi family compound, etc. Let your dreams go wild! Sellers have done a lot of the heavy lifting with recent survey, soil evaluation, and defined recorded access easement. The current R-1 zoning allows for a wide range of residential and agricultural uses. The land is sloping with a great mix of hardwoods and evergreens. What does your future dream look like on this amazing piece of property?

Redgate Rd, Pittsboro
$385,000
3 Beds ⋅ 2 Baths ⋅ 10190084 MLS ⋅ ACTIVE Status
Fabulous Fearrington! This end-unit townhome boasts hardwood floors throughout, a screened porch, main floor primary suite & a living room with vaulted ceiling & gas fireplace. Step into this Fearrington Village beauty and enjoy life the easy way. Just down the street from the Swim & Croquet club and the village shops, you can enjoy the quiet and convenience of townhome living on Whisperwood Close. Contemporary styling, recent hvac (2025), and gleaming white oak floors make this a welcoming space. The kitchen boasts tons of cabinet space, solid-surface tops, gas range, stainless fridge, and a bright breakfast nook. The main floor primary suite overlooks the front garden, and features an ensuite bath & oversized walk-in closet. Upstairs you will find 2 more bedrooms, guest bath, and a cozy balcony overlooking the spacious living room. Relax out back on your brick-floored screened porch overlooking blooming crepe myrtles. Detached garage (owned by HOA). Come see 334 Whisperwood Close today!

334 Whisperwood Close, Pittsboro
$1,170,000
4 Beds ⋅ 4 Baths ⋅ 10189854 MLS ⋅ ACTIVE Status
Start checking boxes! Custom Craftsman tucked away from traffic. CHECK! Quiet 15.4 private wooded acres. CHECK! Covered RV or boat shelter. CHECK! This 4-bedroom, 3.5-bath, 3,221 sq ft home has been freshly updated with new carpet, new paint throughout, all recessed lighting converted to LED, and a completed pre-listing inspection with repairs made. CHECK! Primary suite and main living are all on the main level, with a finished walk-out lower level. Inside: abundant natural light, tray ceilings, custom cabinetry and display shelving, slate foyer, walk-in pantry, dual-fuel range, gas fireplace, central vacuum, radiant-heated primary bath floor, cedar closet, 7x14 laundry room, and ample attic and basement storage. Built for efficiency: passive and active solar, solar-charged battery backup power (batteries replaced 2022), a deep high-GPM well, water softener, metal roof, and recently replaced front windows. Flexible living spaces and handicap-accessible features suit a range of lifestyles. Outdoors: screened porch, multi-level deck and patio, fenced garden, two landscape ponds, and native low-maintenance landscaping, deer- and drought-resistant. Detached two-car garage, an RV or boat shelter with double doors and 14-foot clearance, plus an open carport. Shaded two-mile community walking trail. AT&T fiber. Less than 8 miles to Chapel Hill, close to RDU, RTP and 15/501. Come sit for a spell on the screened porch and see.

67 Bingham Ridge Dr, Pittsboro
$485,000
2 Beds ⋅ 2 Baths ⋅ 10189843 MLS ⋅ ACTIVE Status
Skip the wait for new construction and settle right into this like-new ranch home in the highly desirable 55+ community of Encore at Chatham Park. Designed with comfort and convenience in mind, this thoughtfully planned home offers 2 bedrooms, 2 full baths, and a dedicated office/den that's perfect for working from home, pursuing hobbies, or accommodating overnight guests. The open-concept layout makes everyday living and entertaining effortless. At the heart of the home, the gourmet kitchen features a large center island, abundant cabinet and counter space, a gas cooktop, and stainless steel appliances, all flowing seamlessly into the dining area and family room. A gas log fireplace creates a warm and inviting focal point in the spacious family room. The primary suite is a true retreat, featuring a generous walk-in closet with direct access to the laundry room, a double vanity, and a zero-entry tile shower. Additional upgrades include a convenient drop zone off the garage, epoxy-coated garage floors, and a covered rear patio that's perfect for enjoying North Carolina's beautiful seasons. Looking for extra space? The expansive walk-in attic has already been upgraded with additional insulation and includes a workbench, offering endless possibilities for a workshop, hobby room, or exceptional storage. Best of all, lawn maintenance is included through the HOA, leaving you more time to enjoy Encore's outstanding resort-style amenities. Residents have access to a stunning 5,000-square-foot clubhouse with fitness and gathering spaces, a resort-style pool and hot tub, putting green, cornhole area, tennis and pickleball courts, and a vibrant calendar of social activities. Located within walking distance of Mosaic at Chatham Park, you'll enjoy easy access to restaurants, breweries, a coffee shop, shopping, concerts, fitness classes, and community events. More than just a home, this is an opportunity to embrace an active and connected lifestyle.

200 Imagine Way, Pittsboro
$495,000
2 Beds ⋅ 2 Baths ⋅ 10189623 MLS ⋅ ACTIVE Status ⋅ David Weekley Homes BLDG.
MODEL HOME FOR SALE — MOVE-IN READY! Experience the beautifully designed Inspiration by David Weekley Homes in Encore at Chatham Park. This exceptional model home offers an open-concept layout with a sun-filled family and dining space, a chef's kitchen featuring a dine-up island, abundant cabinetry, plus a covered porch perfect for relaxing or entertaining. The spacious Owner's Retreat includes a luxurious en suite bath and walk-in closet, while the secondary bedroom enjoys convenient access to a full bath privately positioned in the front of the home for added comfort and privacy. Designed with flexibility and energy efficiency in mind, this home features EnergySaver™ innovations throughout. Best of all, the appliances and furniture are included, making this a truly move-in-ready opportunity to own a professionally appointed David Weekley Model Home in the highly desirable Encore at Chatham Park community.

151 Prospect Pl, Pittsboro
$349,990
3 Beds ⋅ 3 Baths ⋅ 10189454 MLS ⋅ ACTIVE Status ⋅ Sampson BLDG.
NEW CONSTRUCTION IN CHATHAM PARK! Welcome to 72 Wandering Way, a designer-finished townhome offering the perfect blend of style, space, and low-maintenance living in one of the Triangle's most exciting master-planned communities. This thoughtfully designed home features 3 bedrooms, 2.5 baths, a spacious loft, and an open-concept main level designed for everyday living and entertaining. The upgraded kitchen is anchored by a large island and features designer cabinetry, stainless steel appliances, and generous counter space, flowing seamlessly into the dining and living areas. Luxury vinyl plank flooring, upgraded stair rails with stained treads and metal balusters, and a private brick courtyard add elevated details throughout. Upstairs, the flexible loft offers valuable additional living space—perfect for a home office, media room, fitness area, or playroom. The spacious primary suite provides a relaxing retreat, while two additional bedrooms offer plenty of flexibility. Enjoy a rear-load 2-car garage and the lifestyle that makes Chatham Park so desirable. Explore nearby parks, greenways and trails, the Chatham Park YMCA, NoVi Green, MOSAIC, Downtown Pittsboro, dining, entertainment, and year-round community events. Convenient to Chapel Hill, Apex, Holly Springs, RTP, and Jordan Lake, 72 Wandering Way puts work, recreation, and the best of the Triangle within easy reach. Brand-new construction, designer-selected finishes, and Chatham Park living—all ready for you. Schedule your private tour today and ask about available builder incentives and financing opportunities. NEW CONSTRUCTION IN CHATHAM PARK! Welcome to 72 Wandering Way, a designer-finished townhome offering the perfect blend of style, space, and low-maintenance living in one of the Triangle's most exciting master-planned communities. This thoughtfully designed home features 3 bedrooms, 2.5 baths, a spacious loft, and an open-concept main level designed for everyday living and entertaining. The upgraded kitchen is anchored by a large island and features designer cabinetry, stainless steel appliances, and generous counter space, flowing seamlessly into the dining and living areas. Luxury vinyl plank flooring, upgraded stair rails with stained treads and metal balusters, and a private brick courtyard add elevated details throughout. Upstairs, the flexible loft offers valuable additional living space—perfect for a home office, media room, fitness area, or playroom. The spacious primary suite provides a relaxing retreat, while two additional bedrooms offer plenty of flexibility. Enjoy a rear-load 2-car garage and the lifestyle that makes Chatham Park so desirable. Explore nearby parks, greenways and trails, the Chatham Park YMCA, NoVi Green, MOSAIC, Downtown Pittsboro, dining, entertainment, and year-round community events. Convenient to Chapel Hill, Apex, Holly Springs, RTP, and Jordan Lake, 72 Wandering Way puts work, recreation, and the best of the Triangle within easy reach. Brand-new construction, designer-selected finishes, and Chatham Park living—all ready for you. Schedule your private tour today and ask about available builder incentives and financing opportunities.

72 Wandering Way, Pittsboro
$975,000
4 Beds ⋅ 4 Baths ⋅ 10189348 MLS ⋅ ACTIVE Status
Welcome to this beautifully designed four bedroom, four bathroom home offering an inviting open-concept layout, abundant natural light, and beautiful hardwood floors throughout the main living areas. The spacious living room features a fireplace with impressive coffered ceiling that adds character and architectural detail. The bright kitchen offers white cabinetry, stainless steel appliances, ample counter space, and a large center island with seating, all flowing seamlessly into the dining and living spaces. Large windows showcase the peaceful, wooded surroundings, while mature landscaping enhances the home's curb appeal. With comfortable gathering spaces and thoughtful finishes throughout, this home is perfect for both everyday living and entertaining.

335 Sweet Pine Cir, Pittsboro
$440,000
3 Beds ⋅ 2 Baths ⋅ 10188737 MLS ⋅ ACTIVE Status
FULLY UPDATED. COMPLETELY TURN-KEY. Welcome to this beautifully updated home in the highly sought-after Fearrington community, perfectly designed for effortless main-level living. The main floor features a spacious primary suite and convenient laundry room, while the inviting living room serves as a cozy centerpiece with a warm fireplace and custom built-in shelving. At the heart of the home, the upgraded kitchen showcases sleek quartz countertops, stainless steel appliances, and a bright eat-in area. Home comes with a detached garage offering additional storage and parking. Beyond the home, enjoy an active and vibrant lifestyle with an array of community amenities just steps away, including a swimming pool, clubhouse, playground, and scenic walking trails.

449 Crossvine Close, Pittsboro
$700,000
3 Beds ⋅ 2 Baths ⋅ 10188676 MLS ⋅ ACTIVE Status
"Nature is not a place to visit, it is home." Set within the picturesque, walkable community of Fearrington Village, 4127 The Knolls Close embodies the serenity, charm, and timeless appeal of Carolina living. Tucked along a quiet street framed by mature trees and beautifully maintained landscapes, this welcoming residence offers an ideal setting for relaxed everyday living and effortless entertaining. Inside, a bright and thoughtfully designed one level layout lives comfortably and intuitively. Generous windows fill each room with natural light, creating warm, inviting spaces perfect for morning coffee, quiet reading, or gathering with friends. The main living area flows seamlessly into the dining and kitchen spaces, giving the home an easy, open feel. The spacious family room features tall ceilings, built ins, and a fireplace—an ideal backdrop for cozy evenings. The large kitchen will delight any cook with abundant cabinetry, ample workspace, granite counters, and stainless steel appliances. The well appointed primary suite offers a generous walk in closet and a beautifully updated bath with an expansive tiled shower. Two additional bedrooms provide flexibility for guests, hobbies, or a home office. Outdoor living is a highlight: a private screened porch overlooking lush greenery, plus a charming courtyard patio and garden that extend the home's peaceful ambiance. This homesite is borders dedicated greenspace. Life in Fearrington Village is truly unique—tree lined paths, friendly neighbors, and beloved amenities including the Fearrington House Inn & Restaurant, The Belted Goat, boutique shops, walking trails, and year round community events. All just minutes from Chapel Hill, Pittsboro, and Jordan Lake.

4127 The Knolls Cl, Pittsboro
$499,900
4 Beds ⋅ 3 Baths ⋅ 10188126 MLS ⋅ ACTIVE Status ⋅ Haddington BLDG.
*Ready in October* Lawncare included in the monthly at $78/mo dues. Located in brand new NoVi Chatham Park, this home offers a true lifestyle with community events on the lawn, including Saturday morning yoga, Games on the Green, and weekend coffee trucks. Enjoy views of the rolling hills of Pittsboro and easy access to trails, parks, the YMCA, and future resort-style amenities. Enjoy low-maintenance living with lawn care and landscaping included in the HOA dues. This stunning new construction home features a first-floor guest bedroom with full bath, open-concept layout, and designer finishes throughout. The chef's kitchen includes a large island, walk-in pantry, and abundant storage, flowing seamlessly into the bright family and dining areas. Upstairs, the Owner's Suite offers a spa-like bath with dual vanities and a large walk-in closet. Two additional bedrooms, a full bath, and a versatile loft provide flexible living space. Outdoor living includes a covered rear porch and breezeway connecting to the two-car garage--perfect for everyday convenience and relaxing evenings.

45 Hillway Rd, Pittsboro
$467,000
3 Beds ⋅ 3 Baths ⋅ 10188003 MLS ⋅ ACTIVE Status
Welcome to 552 Weathersfield, located in desirable Fearrington Village. This spacious and light-filled home offers a wonderful combination of character, flexibility, and exceptional storage. An open, flowing floor plan connects the main living spaces, while large windows throughout bring in abundant natural light and beautiful wooded views. The dramatic living room features a vaulted ceiling, fireplace, and built-in cabinetry and shelving, creating an inviting focal point for the home. Just beyond, a bright sunroom is surrounded by windows and topped with a skylight—an ideal spot for morning coffee, reading, hobbies, or simply enjoying the peaceful setting. Peering out the windows enjoy an abundance of green space and even a small pond with a stacked-stone surround. It is rare for a townhome in Fearrington to have this much privacy and green space! The dining area provides generous space for entertaining and flows easily into the kitchen and adjoining breakfast area. The kitchen offers an abundance of white shaker-style cabinetry, extensive counter space, a center island with cooktop, and a large walk-in pantry with built-in shelving. The sunny breakfast area features walls of windows, a vaulted ceiling, and a skylight, making everyday meals feel anything but ordinary. The spacious primary suite provides plenty of room for a sitting area and includes a private bath with a double vanity and an oversized tiled walk-in shower with frameless glass enclosure. The extensive walk-in closet is outfitted with a closet organizing system, and the stack washer-dryer is conveniently located in this space. Upstairs, find two additional large bedrooms; each feature their own walk-in closet with organizing systems, providing storage rarely found in secondary bedrooms. An attached bonus/flex room with built-in shelving and a window adds even more versatility—perfect for a home office, craft room, reading room, hobby space, or additional storage. Beautiful parquet flooring extends through much of the home, while built-ins, skylights, vaulted ceilings, generous room sizes, and an abundance of windows give the interior its distinctive character. With multiple gathering spaces and flexible rooms, this home offers plenty of opportunity to make each space your own. Located in the highly desirable Fearrington Village community, this is a home with the space, natural light, storage, and flexibility to accommodate the way you want to live. Fearrington has multiple clubs and social opportunities. Duke Center for Living is on the adjoining property, providing a convenient fitness center enjoyed by many Fearrington residents.

552 Weathersfield, Pittsboro
$395,000
3 Beds ⋅ 3 Baths ⋅ 10187805 MLS ⋅ ACTIVE Status
Spacious townhouse in a wooded enclave of just three units. The home offers generously sized rooms and ample closet space. The front door opens to an entry hall leading to the living and dining rooms. The living room features a vaulted ceiling, skylights, a fireplace, and built ins. A den/sunroom opens to the back porch. The bright kitchen includes a breakfast area and pantry/laundry room. The main-level primary bedroom suite has a private bath and large walk-in closet. There is also a main floor powder room for guests. Upstairs, a hallway landing/flex space leads to two large bedrooms, both with walk-in closets, a full bath, and a small bonus room ideal for a study or craft room. Zoned HVAC keeps both levels comfortable. One-car garage with storage space.

486 Beechmast, Pittsboro
$635,000
2 Beds ⋅ 2 Baths ⋅ 10187535 MLS ⋅ ACTIVE Status
Truly better than new! Just ten months old, this beautiful David Weekley home offers the best of new construction without the wait, hassle, or added expense—with upgrades that are already complete. Located in the beautiful Encore at Chatham Park, the Triangles premier 55+ active adult community. This home feels warm and sophisticated, and the Mosley floor plan balances open-concept living with private retreats. French doors open to a dedicated study, or additional guest room when needed. Gorgeous rich wood plantation shutters throughout. The kitchen is the heart of the home and is as beautiful as it is functional, with Quartz countertops, a striking glass tile backsplash, and SS appliances that are nearly new and remain under warranty. With decorative pendant lighting, a generous center island, and a walk-in corner pantry this space is designed for both everyday living and effortless entertaining. The porch provides another "room" for entertaining, with finished epoxy floor, overlooking the fenced backyard and peaceful views of mature trees, your private sanctuary. The primary suite, situated at the back of the home provides a quiet escape. The luxurious bath features a zero-entry walk-in shower, and the newly done, professionally designed custom closet is a standout, complete with built-in cabinetry, dresser drawers, and exceptional shoe storage—thoughtfully designed to maximize both beauty and function. The spacious laundry room is impressive, offering built-in cabinetry, generous countertop workspace, a dedicated folding station, drop zone, storage closet, and nearly new washer and dryer that convey. Even the garage has been elevated with professionally painted walls, durable epoxy flooring, and is already wired for an EV charging station. With a tankless water heater, there isn't anything that was missed in this gorgeous home. Exceptional value with thousands invested in thoughtful post construction upgrades. Skip the construction. Skip the projects. Simply move in and enjoy!

236 Aspen Ave, Pittsboro
$599,900
2 Beds ⋅ 2 Baths ⋅ 10187353 MLS ⋅ ACTIVE Status
Elegance meets everyday comfort in The Carroway, a floor plan designed to make every day feel effortless. At its heart is a glamorous kitchen, anchored by a multi-function island and opening onto sunlit living and dining spaces — perfect for cooking, entertaining, or simply gathering together. The Owner's Retreat offers a true escape, featuring an en suite bathroom and spacious walk-in closet for a private, restorative haven. A well-appointed guest room with its own bathroom ensures visitors enjoy comfort and privacy of their own. Step outside to the covered porch, an inviting extension of the home ideal for quiet evenings or lively gatherings with friends and family.

39 Englehart 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 .