Pittsboro Homes with Chatham - Seaforth High School

Welcome to Pittsboro, North Carolina, a charming town nestled in the heart of Chatham County. Known for its rich history and vibrant community, Pittsboro offers a delightful blend of small-town charm and modern conveniences. Surrounded by the breathtaking beauty of the North Carolina countryside, this picturesque town is a haven for outdoor enthusiasts, with ample opportunities for hiking, fishing, and exploring the serene landscapes.

One of the standout features of Pittsboro is its commitment to education, particularly with the presence of the highly regarded Chatham - Seaforth High School. Families seeking quality education for their children will find a welcoming environment here, where academic excellence and extracurricular activities thrive. The school is known for its dedicated faculty and a strong sense of community, making it an ideal choice for families looking to settle down in the area.

The real estate market in Pittsboro is as diverse as its residents, offering a variety of homes that cater to different lifestyles and budgets. From charming historic houses with character to modern new builds with all the latest amenities, there’s something for everyone. Many homes are conveniently located near Chatham - Seaforth High School, providing easy access for students and peace of mind for parents.

As you explore the neighborhoods of Pittsboro, you’ll discover friendly neighbors, local shops, and delightful eateries that make this town feel like home. Whether you’re looking to buy your first home or searching for a peaceful retreat, Pittsboro is a place where you can truly thrive. Come and experience the warmth and charm of this hidden gem in North Carolina!

Newest Pittsboro Homes with Chatham - Seaforth High 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

$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

$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

$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

$3,075,000

5 Beds ⋅ 6 Baths ⋅ 10188976 MLS ⋅ ACTIVE Status

Dream Home on Top of the Hill — Luxury Presale Opportunity A rare presale opportunity to create an extraordinary modern estate by Dunning Custom Homes, beautifully positioned atop more than 10 acres in one of Chatham County's most stunning settings. Close to the lake and overlooking acres of natural beauty, this exceptional homesite offers the seclusion and serenity of a mountain retreat while remaining convenient to the Triangle and rapidly growing Chatham Park. Designed with dramatic architectural details and sophisticated finishes, the home will feature a stunning wood-clad ceiling anchoring the great room, complemented by a commanding black stone fireplace. The chef's kitchen is designed for both everyday living and entertaining with a professional-grade range, expansive waterfall stone island with seating, and a dedicated scullery providing additional prep and storage space. The formal dining room, with gallery-quality proportions, connects seamlessly to an impressive covered outdoor living area featuring a built-in stone grill kitchen and peaceful views into the surrounding tree canopy. The main-level primary suite is designed as a private retreat, with a wall of windows bringing the outdoors in. The spa-inspired bath will showcase a dramatic matte-black freestanding soaking tub, while the designer walk-in closet features custom built-in cabinetry and a distinctive library ladder. One of the home's architectural signatures, a striking circular staircase, descends to the finished daylight lower level, where the exceptional entertaining and guest spaces continue. Plans include a stone-accented wet bar, spacious family room, private study, and additional bedrooms with en-suite baths. An oversized three-car side-entry garage provides generous parking and storage while maintaining the home's impressive approach and architectural presence. Because construction has not yet begun, a buyer who chooses to build with Dunning Custom Homes will have the opportunity to fully customize the floor plan and selections from top to bottom, creating a home uniquely suited to their vision and lifestyle. The current pricing reflects an estimated cost for a buyer choosing to build this home as presented, using the builder's standard level of quality, products, and finishes. 10+ acres. Privacy. Views. Architectural distinction. Luxury new construction. All within convenient reach of the Triangle and the exciting growth of Chatham County. A remarkable opportunity to make this Dream Home on Top of the Hill your own.

388 Talon Dr, 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

$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

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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 .