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$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
$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
$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
$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
$1,179,000
5 Beds ⋅ 4 Baths ⋅ 10188438 MLS ⋅ ACTIVE Status
Welcome home to this stunning Homes by Dickerson "Henderson Craftsman" executive residence, perfectly situated on a beautifully landscaped 1.57-acre wooded lot in the sought-after Henderson Place community. Thoughtfully designed for comfortable everyday living and effortless entertaining, this exceptional 5-bedroom, 3.5-bath ranch-style home offers elegant finishes, energy-efficient construction, and peaceful natural surroundings. The inviting front entry opens to a spacious home office and an open-concept floor plan featuring rich hardwood flooring, extensive crown molding, custom lighting, and abundant natural light. The gourmet kitchen is a chef's dream, showcasing Cambria quartz countertops, a stylish glass tile backsplash, a new tiled backsplash, a massive custom island with abundant storage, a large walk-in pantry, and a 5-burner Frigidaire Professional natural gas range. The kitchen flows seamlessly into the expansive family room, highlighted by a striking 48-inch Majestic Echelon II linear gas fireplace. The luxurious main-level owner's suite offers a private retreat with a spa-inspired bath featuring a large walk-in shower, Jacuzzi tub, and an oversized custom walk-in closet. Two additional bedrooms on the main floor provide flexible space for guests, multigenerational living, or additional home offices. Upstairs, you'll find a spacious bonus room, two generously sized bedrooms, a full bath, and walk-in closets with plentiful storage throughout. Designed to bring the outdoors in, the family room opens through dramatic cantilevered sliding glass doors to a large screened porch with skylights overlooking the serene wooded backyard. Enjoy spectacular seasonal blooms, colorful autumn foliage, and exceptional privacy while relaxing on the screened porch or secluded back deck. Additional premium features include: New roof (2023) Tankless water heater Central vacuum system with four ports Solar tubes providing natural light in two interior bathrooms High-performance bathroom exhaust fans Custom window shades throughout Upgraded plumbing fixtures Smoke alarms throughout Two-car garage with additional storage HERS-rated energy-efficient construction with a sealed crawl space Outdoor Living & Community The professionally landscaped 1.57-acre homesite offers both manicured outdoor living spaces and a preserved natural wooded area. Gutters with gutter guards have been installed on all roofed areas for easy maintenance. Located on a quiet street with minimal traffic, Henderson Place offers a peaceful setting while providing access to wonderful neighborhood amenities. The HOA maintains beautifully landscaped common areas, including Lizzie's Meadow and John's Lookout, inviting gathering spaces for neighbors and guests alike. Just minutes away, you'll enjoy convenient access to the Fearrington Marketplace, restaurants, tennis courts, shopping, and other community amenities.

4235 Henderson Pl, Pittsboro
$735,000
3 Beds ⋅ 2 Baths ⋅ 10185946 MLS ⋅ ACTIVE Status
MOVE IN READY HOME! LIST OF UPDATES AVAILABLE. A Private, Modern Retreat backing to 247 Acres of Forever Protected Woods. Some homes feel tucked away, this one feels like a world of it's own. Set on a private homesite and backing directly to 247 acres of permanently protected Triangle Land Conservancy land, this updated one-level home delivers the kind of wooded view you simply cannot replicate and will never lose. Step into the tree-top deck and you're surrounded by quiet, filtered light, and the sense that nature is part of your everyday life. Inside, the home is bright, open and move-in ready: 3 Bedrooms, 2 updated baths, fresh paint, smooth ceilings, new skylights, and a long list of improvements that have been thoughtfully documented for buyers who appreciate quality. The layout lives comfortably and efficiently, with natural light pouring in from every angle. A standout bonus: the oversized garage with its own mini-split system, giving you a heated and cooled flex space for hobbies, workouts, storage, or the workshop you've always wanted. And while the setting feels private, you're still in the heart of the community everyone loves. Here, you are minutes from: Our Village Center with restaurants, the greatest independent bookstore, and a weekend pub with live music. Walking trails and paths that weave through the neighborhood. The park and lake, perfect for morning walks or sunset strolls. And of course, our iconic Belted Cows and Goats that make this place feel like nowhere else . It's the kind of neighborhood where you truly have everything you need and never feel the need to leave. A modern, move-in ready home. A forever wooded backdrop. A community with a heart. This is the lifestyle buyers are searching for and it's waiting right here.

686 Spindlewood, Pittsboro
$700,000
3 Beds ⋅ 3 Baths ⋅ 10185538 MLS ⋅ ACTIVE Status
Enjoy wooded, forest-like views from this updated one-level contemporary home in Fearrington Village's "The Woods" section. Set on a .84-acre lot with mature trees and natural landscaping, the home offers a flexible floor plan suited to a variety of needs. The spacious main living room features a high ceiling, fireplace, and ample space for both dining and additional seating. The remodeled kitchen includes a walk-in pantry. A quiet office or flex space with two walls of windows is ideal for working from home or reading, while the enclosed porch functions well as either a screened porch or sunroom. The primary bedroom includes two walk-in closets and a private bath. A second full bedroom also has a private bath, and a third smaller bedroom or study is served by a third bathroom. Large front porch. Additional features include an oversized two-car garage and paved driveway.

672 Spindlewood, Pittsboro
$427,500
3 Beds ⋅ 2 Baths ⋅ 10181660 MLS ⋅ ACTIVE Status
Beautifully designed contemporary home on a naturally wooded lot in Fearrington Village. Vaulted ceilings, skylights, and abundant windows fill the home with natural light and frame views of the wooded setting. The front door opens to an entry foyer, leading to a living room with a fireplace and a dining area with sliding glass doors to the rear deck. The spacious kitchen includes a pantry and gas stove, with an adjoining laundry room that offers a second pantry. The main-level primary bedroom features a walk-in closet and full bathroom. Upstairs are two additional bedrooms and another full bath. Recent updates include fresh interior paint and new bedroom carpet. Exterior storage closet included.

4 Matchwood, Pittsboro
$875,000
3 Beds ⋅ 3 Baths ⋅ 10180964 MLS ⋅ ACTIVE Status
Exceptional custom home offering a fantastic single-level floor plan with a full basement, ideally situated on a private wooded cul-de-sac shared by only three homes in desirable Fearrington Village. Hardwood, parquet, and carpeted flooring combine warmth and character throughout the home.The spacious primary suite features an extraordinary 11' x 11' walk-in closet complete with a custom organization system and center island. The inviting family room is anchored by a fireplace and framed by two full walls of custom built-in cabinetry, providing abundant storage and display space. Designed for both everyday living and entertaining, the expansive kitchen offers a large center island with storage on all sides, extensive cabinetry, and a beautiful furniture-style cabinet featuring glass display doors and a plate rack. A remarkable custom pantry includes wall-to-wall cabinetry with roll-out lower drawers, a full countertop, and an additional sink for exceptional storage and workspace. The well-appointed laundry room is equally impressive with a full wall of upper and lower cabinetry, an organization system, and a utility sink. Enjoy outdoor living on the screened porch and adjoining grilling deck overlooking a peaceful wooded setting that provides exceptional privacy with minimal yard maintenance. The walk-out lower level offers an additional 1,164 square feet of finished space featuring a kitchenette with dining area, flex space, two bedrooms, and a full bath. This finished area was completed without permits and is not included in the home's reported living square footage. The lower level also includes an abundance of unfinished storage, multiple workshop areas, and a utility sink, making it ideal for hobbies, projects, or additional storage. Additional features include a new roof (2025), new water heater (2023), plantation shutters throughout, wide doorways designed for aging in place, and numerous storage closets throughout the home. Fearrington Village is renowned for its vibrant social atmosphere, walking trails, beautiful surroundings, and community amenities. Galloway Ridge Fitness is conveniently located on the adjoining property, offering additional wellness opportunities just steps away.

862 Hatfield, Pittsboro
$699,000
4 Beds ⋅ 3 Baths ⋅ 10179343 MLS ⋅ ACTIVE Status
Tucked away on a cul-de-sac backing to undeveloped land, this beautiful one-level home in.the Bradford Place neighborhood within Fearrington Village offers the perfect combination of comfort, flexibility, and peaceful surroundings. Freshly painted throughout with brand-new carpet as well! The light-filled interior features an inviting, open layout with vaulted ceilings and skylights, custom built-ins, and a fireplace that creates a warm gathering space for family and friends. Large windows frame serene views of the natural landscape, bringing the outdoors inside. A standout feature is the detached guest cottage, offering exceptional versatility for visiting family and friends, a private home office, art studio, fitness space, or hobby room. The spacious primary suite provides a relaxing retreat, while additional living spaces offer room to spread out and entertain with ease. Step outside to enjoy the quiet setting and privacy of a backyard that borders undeveloped land, creating a peaceful backdrop that's increasingly hard to find. The front features a private courtyard. You'll enjoy easy access to walking trails, parks, shops, restaurants, and all the charm this award-winning community has to offer, while remaining just minutes from Pittsboro, Chapel Hill, and the greater Triangle. Flexible living spaces, and an exceptional setting make this a rare opportunity in one of Chatham County's most sought-after communities. Come take a look today.

1379 Bradford Pl, 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 .