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$1,250,000
4 Beds ⋅ 4 Baths ⋅ 10182398 MLS ⋅ ACTIVE Status
Perched atop a scenic hill in Cedar Mountain, this extraordinary custom retreat blends refined mountain-lodge architecture with breathtaking long-range views, exceptional craftsmanship, & thoughtfully designed outdoor living on 2.6 beautifully landscaped acres. A handcrafted stone moongate welcomes you through lush gardens filled with carefully selected plantings that provide year-round color & texture—from vibrant azaleas to yarrow & everything in between. A covered stone front porch with a vaulted cedar ceiling & impressive custom wood entry door sets the tone for the remarkable home within. The stunning great room features soaring vaulted wood ceilings accented by reclaimed pine beams salvaged from a historic 100-year-old local tobacco warehouse. A floor-to-ceiling stone fireplace with a holly wood mantel, creates a warm focal point, while an expansive wall of windows frames panoramic wooded vistas, spectacular sunsets, & the ever-changing beauty of the seasons. The sunroom offers a peaceful retreat with a vaulted cedar ceiling, tiled flooring, and 2 walls of windows that seamlessly connect the living area to the luxurious primary suite. The thoughtfully designed main level also includes 2 primary suites, providing exceptional flexibility for guests or multigenerational living. A dedicated office features custom built-in bookcases, elegant wainscoting, & a stained-glass transom, while a nearby hallway showcases a built-in glass curio cabinet. Designed for both everyday living & entertaining, the gourmet kitchen features rich knotty alder cabinetry, granite countertops, a Thermador 6-burner gas cooktop with pot filler, & a large stainless-steel center island that anchors the beautifully planned workspace. Adjacent to the kitchen, the spacious laundry and mudroom includes a built-in drop zone with bench, cubbies, and a pet door leading to the expansive rear porch. With its vaulted cedar ceiling, reclaimed wide-plank flooring, & dual ceiling fans, this inviting outdoor living area overlooks the breathtaking backyard. Upstairs, you'll find 2 additional bedrooms, a shared bath, a generous loft, & a charming "secret" reading nook sure to delight children & guests alike. A massive unfinished attic offers exceptional expansion potential. Already equipped with lighting, electrical outlets, plumbing for a future bath, and its own electrical panel, the space is ideal for a media room, recreation area, fitness studio, or additional living space. The oversized two-car garage includes a dedicated workshop area, insulated walls, insulated ultra-quiet garage doors, & an EV charging station. Outdoor amenities are truly exceptional. A spacious rear deck, partially shaded by a pergola, captures sweeping views & leads via a beautiful stone staircase to an expansive patio with a built-in fire pit & stone seating—perfect for gathering under the stars. The resort-style heated pool extends the swimming season & is complemented by a stunning pavilion featuring a ceiling fan, rustic built-in cabinetry & countertops, a gas line for grilling, & a dedicated storage room for pool equipment & outdoor gear. Massive stone patios, retaining walls with integrated seating & lighting create a private, peaceful setting unlike any other. Additional highlights include: Custom top-down/bottom-up shades throughout the front of the home, including a remote-controlled kitchen shade. Custom-built chicken coop with protected run. Hobby greenhouse with water service. Irrigation spigots conveniently placed throughout the property for effortless gardening. Dedicated garden area with a gabion stone wall. Extensive custom stonework—including planters, retaining walls, walkways, borders, patios, & outdoor living spaces—crafted primarily from stone harvested directly from the property. Every detail of this remarkable home has been carefully curated to create a private sanctuary where timeless craftsmanship, modern comfort, & unforgettable natural beauty come togethe

1624 Cedar Grove Rd, Pittsboro
$1,173,000
3 Beds ⋅ 3 Baths ⋅ 10182181 MLS ⋅ COMING SOON Status
Nestled on a beautifully landscaped lot of over one acre, this exceptional 3 bedroom, 2.5 bath executive home offers the perfect blend of luxury, comfort, and thoughtful design. From the stunning stone and fiber cement exterior to the impeccably maintained interior, every detail has been carefully crafted for elegant everyday living. The heart of the home is the gourmet cook's kitchen featuring granite countertops, a large center island with dual disposals, natural gas cooktop, built-in oven/microwave combination, Energy Star appliances, and a spacious walk-in pantry. Enjoy casual meals in the charming breakfast area overlooking the lot's wooded and private back yard or entertain guests in the separate formal dining room. Hardwood floors flow throughout the main level, leading into the inviting family room with custom built-in bookshelves and a cozy natural gas log fireplace. A second gas log fireplace enhances the screened porch, complete with custom shades for year-round enjoyment and relaxation. The exquisite owner's suite provides a luxurious retreat with a spa-inspired bath featuring a walk-in shower, soaking tub, and generous space for comfort and privacy. Additional highlights include ceiling fans, Plantation shutters, a convenient main-level utility room, low-flow plumbing fixtures, and a tankless water heater with circulating hot water system. Spacious and versatile, this beautifully designed home offers room for everyone with a thoughtfully finished lower level perfect for multi-generational living, entertaining or guest accommodations. Enjoy a large finished recreation room ideal for movie nights, game days, or a home gym, along with 2 spacious bedrooms and a full bath providing comfort and privacy for family or visitors. The lower level also features access to a huge unfinished storage area with endless possibilities - perfect for a workshop, hobby space, or fitness area. With abundant storage and flexible living spaces throughout, this home combines functionality and comfort in every detail. Outdoor living is equally impressive with a fenced backyard, irrigation system and ample space to enjoy nature's peaceful surroundings. Additional features include a sealed crawlspace, county water, community sewer, durable 30-year shingle roof warranty and natural gas fuel service. Designed by Home by Dickerson with future convenience in mind, the home's construction also incorporates space and options for a potential elevator installation if desired. This remarkable property combines timeless style, energy efficiency, and modern functionality in a serene setting you'll love coming home to.

4200 Henderson Pl, Pittsboro
$340,000
3 Beds ⋅ 2 Baths ⋅ 10181905 MLS ⋅ ACTIVE Status
Priced to sell! This 3-bedroom, 2-bath ranch offers 1,570 sq ft of comfortable living space on a 0.27-acre lot. Formal dining room, flat-surface countertops, a cozy gas fireplace, and a functional floor plan ready for your personal touches. Enjoy outdoor living with a covered front porch, spacious back deck, and fully fenced backyard. A/C system installed in 2025 provides added value and peace of mind. With a little updating, this home presents an excellent opportunity for homeowners or investors alike. Being sold as is and priced accordingly for a quick sale. Walkable to downtown Pittsboro.

8 Hawks Spiral Way, Pittsboro
$1,340,000
4 Beds ⋅ 4 Baths ⋅ 10181414 MLS ⋅ PENDING Status
Welcome home to over 3,700 square feet of thoughtfully designed living on a beautiful 1-acre wooded homesite just minutes from charming downtown Pittsboro, a short drive to Chapel Hill, and convenient to the outdoor recreation of Jordan Lake. This stunning 4-bedroom, 3.5-bath home offers the perfect blend of spacious living and peaceful surroundings. Enjoy generous gathering spaces, a well-appointed layout ideal for everyday living and entertaining, and the privacy of a large wooded lot. Experience the best of both worlds with a serene setting and convenient access to shopping, dining, recreation, and all that the growing Pittsboro area has to offer.

228 Rexford Ln, Pittsboro
$1,160,000
4 Beds ⋅ 5 Baths ⋅ 10181215 MLS ⋅ ACTIVE Status
Updated custom home in Henry's Ridge with a first-floor primary suite, designated office, formal dining room and oversized sunroom on 1.6 private acres. Offering 4 bedrooms, 3 full baths, 2 half baths, and 4,847 square feet, this home is conveniently located just off Hwy. 64 near Jordan Lake with easy access to Pittsboro, Chapel Hill, Apex, and Cary. Extensively updated in 2021 with a remodeled kitchen featuring custom cabinetry, quartz countertops, oversized 3-inch island, expanded pantry with appliance nook, custom mudroom, enlarged laundry room with built-in dog wash, refinished hardwood floors, fresh interior paint, and custom built-ins.Outdoor living is designed for entertaining with an in-ground pool, pool house, exterior half bath, renovated decks, professionally landscaped yard, irrigation system, and commercial-grade landscape lighting. Additional features include a tankless water heater, reverse osmosis water filtration system, generator wiring, and an additional water heater with recirculation. The flat, tree-lined lot backs to approximately 80 acres that are unlikely to be developed, providing exceptional long-term privacy. Parking for approximately 12 vehicles.

242 Henrys Ridge Rd, Pittsboro
$1,049,000
3 Beds ⋅ 3 Baths ⋅ 10181175 MLS ⋅ PENDING Status
Back on the market due to change in job circumstance. Don't miss out on this special opportunity. Situated on a picturesque 1.33-acre homesite, 4233 Henderson Place offers the perfect blend of comfort, space, and lifestyle in the heart of Fearrington Village--a community celebrated for its charming village center, boutique shopping, dining, and scenic surroundings. This 3-bedroom, 2.5-bath home features a thoughtfully designed layout with a dedicated office and a large upstairs bonus room, ideal for a media space, playroom, or guest retreat. The main living areas are filled with natural light and flow seamlessly into a beautiful kitchen, designed to be both functional and inviting--perfect for everyday living and entertaining. A standout feature of the home is the living room's multi-fold doors, which open fully to the screened-in porch--creating a seamless indoor-outdoor living experience. Whether hosting guests or enjoying a quiet evening, this unique design allows the living space to expand effortlessly and brings the outdoors in. The spacious primary suite serves as a true retreat, highlighted by a large walk-in closet and a luxurious en-suite bath featuring an expansive walk-in shower. Each additional bedroom offers comfort and flexibility, while the home's layout provides room to grow and adapt to your needs. Upstairs, a generous walk-in attic presents excellent storage or the opportunity to create additional finished living space. A walk-in crawl space adds even more convenience and accessibility. Step outside to enjoy the peaceful setting and expansive yard, complete with an irrigation system to maintain the landscape year-round. Surrounded by natural beauty, it's not uncommon to spot deer and local wildlife passing through, adding to the serene, retreat-like atmosphere. Whether relaxing at home or exploring all that Fearrington Village has to offer, this property delivers a rare combination of privacy, charm, and modern comfort.

4233 Henderson Pl, Pittsboro
$615,000
4 Beds ⋅ 3 Baths ⋅ 10181040 MLS ⋅ ACTIVE Status
From the moment you step through the front door, you'll feel it—this is more than a house; it's a home where love has flourished, laughter has echoed through every room, tiny footsteps became confident strides, and countless memories have been made. Every space tells a story, and now it's ready for its next chapter with you. Beautifully and thoughtfully updated, this exceptional home combines timeless elegance with modern comfort. Rich Bellawood hardwood flooring flows throughout the entire first floor, creating warmth and continuity. The elegant dining room showcases a tray ceiling and classic wainscoting, perfect for hosting holiday dinners and special celebrations. The breathtaking great room welcomes you with soaring vaulted ceilings, custom built-in cabinetry, and a cozy gas-log fireplace with a blower that makes winter evenings especially inviting. The heart of the home—the kitchen—features premium KitchenAid stainless steel appliances and an inviting breakfast nook complete with a custom-built storage bench, creating the perfect place for morning coffee, family breakfasts, or helping with homework. Designed with privacy and comfort in mind, the split-bedroom floor plan offers a peaceful primary suite tucked away from the secondary bedrooms. The luxurious spa-inspired primary bath features a soaking tub, a separate shower with dual shower heads, and even its own dedicated water heater for added convenience. French doors from both the great room and the primary suite open onto an expansive deck, seamlessly blending indoor and outdoor living. Every lighting fixture throughout the home has been meticulously selected and updated, including elegant pendant lighting that gracefully frames the primary bedroom, adding warmth, sophistication, and designer appeal. Step outside, and you'll discover what many have described as a magical private park. This extraordinary backyard is a peaceful sanctuary surrounded by mature trees and beautifully curated landscaping. Relax in the hammock beneath the shade, gather fresh blueberries and blackberries, or stroll among blooming peonies, hydrangeas, and tulips. At its heart is your own tranquil pond with a graceful fountain and a Toro lantern, carefully brought from Japan, creating a setting that feels both serene and unforgettable. Upstairs offers incredible flexibility with an expansive bonus room complete with a closet, generous walk-in attic storage, a dedicated office or flex room, a beautifully remodeled full bathroom, and a spacious fourth bedroom with peaceful views overlooking the neighborhood pond. The location is just as impressive. Jordan Lake is only 10 minutes away, offering endless opportunities for boating, fishing, hiking, and recreation. The future Disney STORYLIVING community will be just five minutes away, bringing exciting new restaurants, shopping, entertainment, and amenities to the area. Families will appreciate the excellent educational options, including highly regarded public schools, Thales Academy, Haw River Christian Academy, Woods Charter School, and Chatham School of Science & Engineering. Every improvement has been made with care. Every room has been loved. Every corner invites you to imagine the memories still waiting to be made. Come experience this impeccable modern home for yourself—and prepare to fall in love.

438 May Farm Rd, 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
$1,199,000
3 Beds ⋅ 4 Baths ⋅ 10180831 MLS ⋅ ACTIVE Status
Nestled on a private, wooded 1.63-acre homesite just 3 miles from charming downtown Pittsboro, this stunning new construction home offers the perfect blend of tranquility and convenience. Designed for effortless living, this thoughtfully crafted single-level home features 3 bedrooms, 3.5 baths, and an open-concept floor plan with exceptional craftsmanship throughout. The gourmet kitchen boasts a large center island, walk-in pantry, and wet bar, flowing seamlessly into the spacious great room with soaring 12-foot ceilings and decorative beams. Retreat to the luxurious owner's suite featuring a vaulted ceiling, spa-inspired bath, and oversized walk-in closet. Each secondary bedroom includes its own en-suite bath, offering comfort and privacy for family or guests. Enjoy year-round outdoor living on the expansive covered rear porch overlooking the peaceful wooded setting. With a formal dining room, oversized laundry room, abundant storage, and a spacious 3-car garage, this home combines timeless design with modern convenience in one of Pittsboro's most desirable locations.

71 Caz Trce, Pittsboro
$789,000
4 Beds ⋅ 3 Baths ⋅ 10180739 MLS ⋅ ACTIVE Status
Behind the gates of Chapel Ridge Estates, this home offers 3 main-level bedrooms, including a primary suite with double vanity, walk-in shower with bench and handheld sprayer, walk-in closet and reverse-osmosis water spigot. The kitchen features granite counters, an island, gas cooking, stainless refrigerator, under-cabinet lighting and RO water at the sink. A tray-ceiling dining room, breakfast room, hardwood floors and family room with gas fireplace offer flexible gathering spaces. Relax on the screened porch or deck overlooking the fenced yard. Upstairs adds a bonus room, 4th bedroom, full bath and walk-in attic. The laundry room has a utility sink. A conditioned wine cellar occupies part of the 3rd garage bay and was designed for easy removal if needed. A 24 kW Generac provides whole-home backup power. Community perks include a pool, clubhouse, fitness center, courts, playground, golf, and bar and grill.

53 Spring Hollow Ct, Pittsboro
$498,000
3 Beds ⋅ 2 Baths ⋅ 10180426 MLS ⋅ ACTIVE Status
Welcome to 396 Lyndfield Close, a beautifully updated end-unit townhome in the highly sought-after Fearrington Village community of Pittsboro, NC. Offering 3 bedrooms, 2 fully renovated bathrooms, a desirable main-level primary suite, and a one-car garage. This meticulously maintained home blends timeless charm with thoughtful modern updates in one of Chatham County's most picturesque neighborhoods. Natural light pours through multiple skylights, illuminating the open-concept floor plan and gleaming hardwood floors throughout the main level. The inviting family room showcases custom built-in bookcases and bench seating, while the adjoining sunroom provides a peaceful retreat overlooking the private outdoor setting. The 2025 designer-renovated primary suite offers both luxury and functionality with a reimagined layout featuring an oversized tiled walk-in shower, built-in bench seating, frameless glass enclosure, comfort-height vanity, updated lighting, and thoughtfully integrated accessibility features, including reinforced grab bars for added peace of mind. The second full bathroom was also completely renovated in 2025, featuring a new tub surround, expanded entry allowing additional natural light from the skylight, new vanity, fixtures, lighting, and finishes. Step outside onto the oversized deck, refreshed in 2026 with replacement boards, updated railings, and a fresh stain—perfect for morning coffee or entertaining guests. Additional recent improvements include new landscape lighting, wiring and transformer, a new garbage disposal, replacement washer and dryer with new dryer vent, updated upstairs ceiling fan, replacement gas fireplace logs with wireless remote, and professionally cleaned windows, porch, and deck. Quarterly pest control service has been maintained since 2023, reflecting the exceptional care this home has received. The one-car garage provides secure parking and valuable storage space, while the HOA offers added peace of mind by maintaining the termite bond, landscaping, and exterior maintenance, Located in the award-winning Fearrington Village, residents enjoy beautifully landscaped grounds, scenic walking trails, boutique shopping, acclaimed restaurants, community events, and exceptional amenities including swimming, tennis, pickleball, croquet, and a thriving arts scene. Convenient to Chapel Hill, UNC, Jordan Lake, Pittsboro, and the entire Triangle, this move-in-ready home offers the perfect combination of low-maintenance living, modern updates, and an unmatched lifestyle. Beautifully updated. Exceptionally maintained. Perfectly located. Welcome home to Fearrington Village. Experience this incredible property and community here: https://vimeo.com/1210019068?share=copy&fl=sv&fe=ci

396 Lyndfield Close, Pittsboro
$950,000
5 Beds ⋅ 4 Baths ⋅ 10180348 MLS ⋅ ACTIVE Status
Experience luxury living overlooking the 9th hole of Chapel Ridge Golf Course in this exceptional custom home. A grand entry with soaring 10-foot ceilings sets the tone for the elegant finishes found throughout. The thoughtfully designed main level features a private home office with a coffered ceiling and French doors, a secondary first-floor bedroom with an adjoining full bath, and a luxurious primary suite complete with a tray ceiling, dual walk-in closets, and a spa-inspired bath featuring a generous soaking tub, oversized tiled shower, and dual vanities. Designed for both everyday living and entertaining, the gourmet kitchen showcases a 5-burner gas cooktop, wall oven, built-in microwave, farmhouse sink, walk-in pantry, and convenient butler's pantry, all flowing seamlessly into the formal dining room and expansive family room with a cozy gas fireplace. A well-appointed laundry room with a utility sink and drop zone adds everyday convenience. Upstairs, you'll find three spacious bedrooms, two full bathrooms, and an oversized bonus room offering endless possibilities for recreation, media, or guest space. Engineered hardwood flooring extends throughout most of the main floor and the second-floor hallway, while custom millwork enhances the home's refined character. Relax year-round on the expansive screened porch and enjoy peaceful views of the golf course and the tranquil surroundings. Irrigation and a Generac generator completes this remarkable home that combines timeless craftsmanship, sophisticated design, and an unbeatable golf course setting to create an extraordinary place to call home.

39 High Ridge Ln, Pittsboro
$2,900,000
4 Beds ⋅ 6 Baths ⋅ 10180014 MLS ⋅ ACTIVE Status
A rare opportunity to build your custom dream home in the sought-after Stonecrest at Norwood community. This lovely proposed custom home features universal design features to help you age in place. Two primary bedroom suites, the ability to add an elevator and more. One of the last remaining estate lots available, this stunning 2.63-acre homesite offers exceptional privacy, accessed by a long, meandering driveway that sets the tone for the retreat that awaits. Picturesque Wilkinson Creek runs along the property, providing tranquil views and soothing natural ambiance. Embrace the natural beauty of the surrounding woods. Stonecrest at Norwood strikes the perfect balance of peaceful, private living with convenient access to surrounding amenities. Community features include scenic walking trails and a beautifully appointed pavilion with a fireplace -- an idyllic setting from the moment you arrive. Other plans available. This lot is also available for private sale without home construction.

93 Kenwood Ln, Pittsboro
$815,000
4 Beds ⋅ 3 Baths ⋅ 10179814 MLS ⋅ ACTIVE Status
Welcome to this stunning Cape Cod-inspired traditional home nestled on 2.81 private acres, offering over 4,000 square feet of beautifully designed living space. With 4 bedrooms, 3 full bathrooms, and an exceptional floor plan, this home combines timeless elegance with modern comfort. Step inside to discover soaring cathedral ceilings, beautiful hardwood floors, extensive crown molding, recessed lighting, and custom built-in bookshelves that add warmth and character throughout. The spacious living room is anchored by an electric fireplace, creating a cozy gathering space for family and friends. The beautifully appointed kitchen is designed for both function and style, featuring granite countertops, stainless steel appliances, and generous workspace for preparing meals and entertaining guests. A rare and highly desirable feature, this home offers two primary suites, providing flexibility for multi-generational living, extended family, or private guest accommodations The second floor features finished bonus rooms, offering endless possibilities for a home office, media room, playroom, fitness space, or additional guest accommodations. Enjoy peaceful mornings on the inviting rocking chair front porch complete with a porch swing, or relax year-round on the screened porch overlooking the peaceful wooded surroundings. The property also includes an attached double garage along with a detached garage/workshop, providing abundant space for vehicles, hobbies, storage, or projects. Recent improvements offer added peace of mind, including a new roof installed in 2025 and both heat pumps replaced in 2026. Additional features include a Ring® doorbell and security camera system. Conveniently located with easy access to Highway 64, this property offers the perfect balance of privacy, convenience, and country living.

26 Shadymont Dr, Pittsboro
$610,000
4 Beds ⋅ 4 Baths ⋅ 10179531 MLS ⋅ ACTIVE Status
Experience the award-winning 'No Little Plans' Garman Homes floor plan, celebrated for its thoughtful design and exceptional livability. This versatile home features a first-floor guest suite with a full bath and double doors that lead you straight from the suite to the covered front porch! Across the hall, you can find a flex room with a custom shiplap accent wall enclosed with French doors, ideal for a home office, playroom, or additional living space. Designed for both everyday living and entertaining, the open-concept layout centers around a gourmet kitchen featuring quartz countertops, stainless steel appliances, a spacious walk-in pantry, and a convenient pocket office. The kitchen flows into the family room and upgraded screened porch, creating a seamless indoor-outdoor living space. Large sliding glass doors open to the screened porch and fenced backyard, perfect for relaxing or entertaining. Durable LVP flooring extends throughout the main level, stairs, and upstairs hallways, adding warmth and continuity throughout the home. Upstairs, you'll find three additional bedrooms including a spacious primary suite with a private sitting area filled with beautiful natural light. All appliances convey with this home! The thoughtfully designed mudroom off the 2 car garage offers built-in cubbies, hooks, and additional storage, creating a functional drop zone to keep everyday essentials neatly organized. Located in sought-after Chatham Park, residents enjoy an unmatched lifestyle surrounded by miles of greenways, parks, playgrounds, community events, dining, and more! The location is hard to beat, with the newly opened YMCA, Thales Academy, and Knight Farm Community Park all just minutes away and connected by paved, extra-wide greenways throughout the community. Enjoy the convenience of easy access to Downtown Pittsboro, Jordan Lake, Chapel Hill, Apex, and the greater Triangle area, with quick connections to major routes including Highway 64 and 15-501. Experience the amenities and vibrant lifestyle that make Chatham Park one of the Triangle's most desirable places to call home!

51 Millennium Dr, Pittsboro
$300,000
3 Beds ⋅ 2 Baths ⋅ 10176262 MLS ⋅ ACTIVE Status
Updated & Remodeled Home in a Peaceful Wooded Setting! This move-in ready home has been extensively updated over the past 18 months, offering modern finishes and worry-free living. Recent improvements include a new roof, HVAC system, luxury vinyl plank flooring, interior paint, painted cabinetry, light fixtures, range hood, countertops, and appliances. The bathrooms have been beautifully refreshed with new vanities, toilets, mirrors, and refinished tubs/showers. Outside, you'll appreciate the fresh exterior paint and new gravel driveway that create excellent curb appeal. Enjoy outdoor living from the welcoming front porch or relax around the private patio firepit surrounded by attractive landscaping and accent lighting. Additional recent upgrades include a 120" drop-down projector screen in the living room, Tesla EV charger, and a storage shed. With no HOA and no restrictions, you'll have the freedom to enjoy your property your way. Conveniently located just minutes from Jordan Lake, Pittsboro, and Chapel Hill, with easy access to US-15/501 and US-64 for commuting to Raleigh, Cary, and surrounding areas. Plus, the elementary and middle schools are only about a mile away. Modern updates, privacy, convenience, and freedom—all in one exceptional property!

424 Forest Creek Dr, Pittsboro
$735,000
3 Beds ⋅ 3 Baths ⋅ 10175732 MLS ⋅ PENDING Status
Nestled on 2 private acres in one of Pittsboro's most convenient locations, 101 Kentview Drive offers a rare combination of peaceful surroundings, thoughtful updates, and everyday comfort. Enjoy the quiet feel of a nature-filled setting while being just minutes from Fearrington Village, Chapel Hill, UNC, and downtown Pittsboro. The inviting covered front porch welcomes you into a warm, functional layout with generous living spaces and beautifully updated areas, including the kitchen, primary bathroom, and upstairs bathrooms. Additional updates include a new roof (2024), new upstairs carpet (2025), and upstairs HVAC (2025). Outside, the fenced backyard, screened porch, and firepit area make it easy to relax, gather, and enjoy life at home. Located in an established neighborhood with a wonderful sense of community, this home offers the kind of peaceful setting that feels tucked away without feeling isolated.

101 Kentview Dr, Pittsboro
$1,000,000
1 Beds ⋅ 1 Baths ⋅ 10175240 MLS ⋅ ACTIVE Status ⋅ Full Bloom & Galaxy BLDG.
NEW GREAT PRICE- These two homes are sold as a package with their two other counterparts BEE HIVE & OASIS in MLS # 10174990 for a total of four homes for the one asking price. Each home is 1030 htsqft ( 2nd home noted below as Det living area for MLS entry purposes ). Located in Pittsboro, NC and tucked within a peaceful woodland near Chapel Hill and Jordan Lake, Elevate Treehouse was designed as a collection of individually themed luxury retreats, each home blending creative design, modern amenities, and immersed in it's natural surroundings. Each home offers a spacious living area, full kitchen, private bedroom, sleeping loft, and a spa-inspired bath featuring a freestanding soaking tub and oversized walk-in shower. The efficient layout makes excellent use of the home's footprint while still feeling bright and comfortable. Features Include: • Custom bee mural • Oversized luxury shower • Loft sleeping area • Private covered porch • Swing structure • Fire pit access • Starlink internet • Mini-split HVAC • Granite & quartz countertops • Metal Roof Stainless steel appliances Outside, a private deck overlooks the surrounding forest, creating the perfect place to slow down and reconnect with nature. Beyond the homes, Elevate Treehouse Community features walking trails, fire pit gathering areas, water features, picnic spaces, and thoughtfully curated artwork throughout the property. The open-concept layout makes efficient use of every square foot while maintaining a bright, airy feel throughout. The home's spa-inspired bathroom serves as the centerpiece of the experience, featuring a freestanding soaking tub, oversized walk-in shower, and carefully selected finishes. Vaulted ceilings and large windows allow natural light to flow throughout the home while creating a strong connection to the surrounding landscape.Investment Highlights: • Established rental history • 3.72 acres •Walking trails and community amenities • Minutes from Chapel Hill and Jordan Lake. Full Bloom Home- Full Bloom is both bright, cheerful, and full of character and connected to nature. The private deck overlooks the surrounding woodland setting and provides a peaceful place to enjoy the sights and sounds of the property. There are community trails and water features to enjoy. Floral-inspired details and colorful accents create a space that feels welcoming without sacrificing comfort. Large windows allow natural light to fill the home throughout the day, while the open layout helps every room feel connected and easy to enjoy. There are two spacious living areas, full kitchen, private bedroom, loft sleeping space adds flexibility to the floorplan, and luxury bath. The hanging lounge chairs are a favorite feature. The floral details throughout the home give the space a playful energy while still feeling polished and comfortable. Every inch has been designed to feel comfortable, functional, and memorable. The result is a home that feels uplifting, creative, and easy to settle into. Galaxy Home- Your Little Corner of the Universe.One of the best things about Galaxy is the contrast between what's inside and what's outside. A private deck overlooks the surrounding woods & provides a quiet place to begin or end the day. Walking trails, large hammock, outdoor swinging benches & fire pit under a canopy of trees are of this home's private features. Galaxy is truly out of this world. Bold design choices, dramatic finishes, and custom details give the home a personality unlike any other treehouse in the community. Despite its unique look, the home remains comfortable, functional, and easy to enjoy. This home features spacious living areas, full kitchen, private bedroom, loft sleeping area, and oversized luxury shower with celestial themes. Large windows bring natural light into the home and balance the darker design elements throughout.Celestial artwork and custom details contin NEW GREAT PRICE These two homes on this property will be sold with as a package with MLS # 10174990 for this price listed.- four homes total for this one asking price. Each home was professionally measured as 1030+- HtSqFt. The Det Storage building services all 4 homes.

286 Stone Wall Rd, Pittsboro
$2,100,000
4 Beds ⋅ 3 Baths ⋅ 10175188 MLS ⋅ ACTIVE Status
There's a new MARSHALL in town!! :) An exceptional opportunity to acquire 33+ STUNNING ACRES with remarkable lifestyle appeal and long-term investment potential! This unique destination property offers the rare combination of privacy, flexibility, and convenience in a growing area that still preserves a peaceful country atmosphere. With multiple approved 5-bedroom perk sites (potentially more) already in place, significant value has been established for multi-generational living, future homesites, rental income opportunities, subdivision potential, or strategic long-term investment. The property already showcases an impressive blend of renovated living spaces, newer and updated structures, farming and gardening areas, pasture(s), fencing, pond(s), trails, and thoughtfully designed separation options. Whether your vision includes a private family compound, income-producing retreat, hobby farm, estate property, or future development venture, this property provides the space, infrastructure, and versatility to bring those plans to life while maximizing future value. The current main residence, situated in the heart of the property, features 3 bedrooms / 1 full bath and has been updated throughout with comfortable, move-in-ready living spaces, rocking chair front porch and side deck. Additional improvements include an incredible oversized 3-car garage with workshop space and an attached studio-style living area offering 1 bedroom and 1 full bath—ideal for guests, extended family, rental income, or a private office. A separate "small home" adds even greater flexibility, featuring another 1 bedroom, 1 full bath, kitchen/living room, and even a picturesque window bedroom overlooking the pond & fountain, creating an inviting setting for guests, tenants, peaceful retreats, or creative pursuits. Further contributing to its appeal is a 2-stall horse barn with tack room, other small buildings and an additional 2nd large garage/storage building for RV, tractor and/or other farm toys. Properties offering this level of acreage, infrastructure, flexibility, and future upside are increasingly difficult to find, especially in a high-growth location. Enjoy an extraordinary country lifestyle today, while positioning yourself for future appreciation and income possibilities. With approved perk sites and extensive improvements already in place, many of the key steps have been completed, making this a compelling opportunity for buyers seeking both immediate enjoyment and lasting value. Owners are currently renting all 3 living areas on a month-to-month basis for a total of $2,900/month - see LA for details - could be all moved out by closing or potentially stay pending buyer preference. Opportunities like this are rare—don't miss the chance to secure a property that can serve your family, your goals, and future generations to come!

865 Marshall Rd, Pittsboro
$1,000,000
1 Beds ⋅ 1 Baths ⋅ 10174990 MLS ⋅ ACTIVE Status ⋅ Bee Hive Tree House And Oasis Tree House BLDG.
NEW GREAT PRICE These homes are sold as a package with their counterparts Full Bloom & Galaxy in MLS # 10175240 - four homes for this one asking price . Each home is 1030 htsqft ( 2nd home noted below as Det living area for MLS entry purposes ).Located in Pittsboro, NC and tucked within a peaceful woodland near Chapel Hill and Jordan Lake, Elevate Treehouse was designed as a collection of individually themed luxury retreats, each home blending creative design, modern amenities, and immersed in it's natural surroundings. Each home offers a spacious living area, full kitchen, private bedroom, sleeping loft, and a spa-inspired bath featuring a freestanding soaking tub and oversized walk-in shower. The efficient layout makes excellent use of the home's footprint while still feeling bright and comfortable. Features Include: • Custom bee mural • Oversized luxury shower • Loft sleeping area • Private covered porch • Swing structure • Fire pit access • Starlink internet • Mini-split HVAC • Granite & quartz countertops • Metal Roof Stainless steel appliances Outside, a private deck overlooks the surrounding forest, creating the perfect place to slow down and reconnect with nature. Beyond the homes, Elevate Treehouse Community features walking trails, fire pit gathering areas, water features, picnic spaces, and thoughtfully curated artwork throughout the property. BEE HIVE Your Hive Away From Home Inspired by the honeybee and the sense of community it represents, Beehive was designed for gathering, relaxing, and spending time together. Thoughtful details, playful touches, and a peaceful outdoor setting create a stay that's both memorable and cozy. The custom bee mural immediately catches your attention and gives the home a sense of fun that carries throughout the experience. Custom artwork, warm finishes, and thoughtful details give the home a character all its own while maintaining the comfort and functionality guests expect from a luxury retreat. Large windows bring in natural light throughout the day, and the open-concept layout helps every space feel connected One of the best parts of Beehive is that the experience doesn't stop when you step outside. The swing structure and large wooden beehive provide memorable features guests naturally gravitate towards. The private deck offers a peaceful place to enjoy the surrounding woods, while the nearby swing structure has become a favorite gathering spot. OASIS H20 A Water Inspired Woodland Retreat Inspired by the calming movement of water, Oasis H20 offers a peaceful retreat designed for rest, renewal, and connection. Thoughtfully crafted with spa-inspired finishes, soaring ceilings, and woodland views, this unique treehouse experience invites you to slow down and recharge. Drawing inspiration from the calming movement of water, it's soft blue tones, natural textures, and abundant natural light create a space designed for relaxation and renewal. The open-concept layout makes efficient use of every square foot while maintaining a bright, airy feel throughout. The home's spa-inspired bathroom serves as the centerpiece of the experience, featuring a freestanding soaking tub, oversized walk-in shower, and carefully selected finishes. Vaulted ceilings and large windows allow natural light to flow throughout the home while creating a strong connection to the surrounding landscape.Investment Highlights: • Established rental history • 3.72 acres •Walking trails and community amenities • Minutes from Chapel Hill and Jordan Lake • Distinct themed guest experiences These two homes on this property will be sold with as a package with MLS # 10175240- four homes for this one asking price . Each home was professionally measured as 1030+- HtSqFt. The Det Storage building services all 4 homes.

260 Stone Wall Rd, Pittsboro
$530,000
3 Beds ⋅ 3 Baths ⋅ 10173282 MLS ⋅ PENDING Status
This move-in ready home in the beautiful and well-maintained neighborhood of Potterstone Village is tucked away at the end of a cul-de-sac. With 3 bedrooms and 3 full bathrooms, this home features the primary suite and a secondary bedroom on the main level. Upstairs, you'll find a private retreat with a third bedroom, full bath, bonus room, and a large unfinished attic ready to meet your storage needs or become future finished space. Updates include roof (in process 7/26), HVAC (2025), Dishwasher (2026), Microwave (2025), Downstairs carpet (2025), Exterior paint (2023), Water heater (2021), Fresh paint throughout much of the home, 2" Levolor blinds throughout (2025), Custom Bali motorized blind in foyer (2026). This allergen friendly, pet free home has recently had air ducts cleaned and a whole house UV air filter added. While the stove is currently electric, if gas is preferred, a line for hook-up is already in place. Washer and dryer convey adding to the home's move-in ready convenience. The backyard backs up to the Town of Pittsboro greenway, providing a peaceful wooded backdrop and added privacy. Beyond the home itself, residents enjoy access to neighborhood amenities including a community pool, clubhouse, and catch-and-release pond. Ideally located near historic downtown, schools, parks, shopping, and dining, this home combines small-town charm with everyday convenience.

61 Buttonwood Ct, Pittsboro
$574,900
3 Beds ⋅ 3 Baths ⋅ 10172837 MLS ⋅ ACTIVE Status
Tucked among the trees in the heart of historic Fearrington Village, this striking 3-bedroom, 2½-bath contemporary home offers modern design, exceptional craftsmanship, and serene wooded views from nearly every room. With its clean architectural lines and abundant natural light, the home lives like a private modern treehouse--peaceful, elevated, and beautifully connected to nature. Inside, thoughtful design meets everyday functionality. The kitchen features custom cabinetry, granite countertops, stainless steel appliances, tile flooring, and generous windows that fill the space with natural light. Custom cabinetry continues throughout the home in the bathrooms, closets, and laundry, creating a cohesive aesthetic and abundant storage. The spacious living areas showcase vaulted ceilings, skylights, hardwood floors, and a fireplace, all framed by expansive windows overlooking the surrounding woods. The flexible third bedroom offers endless possibilities--ideal as a home office, library, gym, craft room, or music studio. A two-car garage and a walk-in crawl space with a wine cellar provide exceptional storage options rarely found in homes of this size. Beyond the home itself, the lifestyle is what truly sets this property apart. Fearrington Village is consistently recognized as one of the Triangle's most desirable communities, offering a rare blend of charm, connection, and natural beauty. Residents enjoy the village shops and restaurants, the Tennis and Pickleball Association, and the opportunity to join the swim and croquet club. Outdoor living here is a way of life. Scenic walking trails and beautifully maintained gardens wind throughout the village. Visit the beloved Belted Barnyard animals or take a short drive to Jordan Lake for boating, swimming, hiking, and eagle-spotting. The nearby Haw River offers additional opportunities for kayaking, fishing, and peaceful exploration. Whether you prefer an active afternoon outdoors or a quiet morning walk among the trees, the options are abundant. Equally special is the sense of community. Fearrington Village is home to dozens of resident-run clubs spanning interests from arts and literature to fitness and travel, creating countless opportunities to connect and engage. The Fearrington Cares organization, founded to support the health and daily living needs of residents, further reflects the thoughtful and supportive spirit of the neighborhood. This is more than a home--it is a modern retreat set within a vibrant, connected community where nature, lifestyle, and neighborly warmth come together beautifully.

246 Fox Ridge Rd, Pittsboro
$1,475,000
4 Beds ⋅ 5 Baths ⋅ 10172726 MLS ⋅ ACTIVE Status
Timeless architecture meets modern luxury in this exceptional custom residence by The Rexford Group, located within the prestigious estate community of Corbett Landing. Inspired by classic European country estates, this thoughtfully designed 3,825-square-foot home showcases striking brick architecture, dramatic rooflines, expansive windows, and exceptional craftsmanship throughout. Designed for both everyday living and elegant entertaining, the home features a sought-after first-floor primary suite, dedicated home office, spacious bonus room, and 4.5 beautifully appointed baths. The heart of the home is the impressive great room with soaring vaulted ceilings, creating a grand yet welcoming atmosphere filled with natural light. Thoughtfully designed living spaces flow seamlessly throughout, offering comfort, functionality, and timeless appeal. Situated on a generous 1.59-acre homesite surrounded by preserved natural beauty, mature hardwoods, and rolling topography, the property provides a rare combination of privacy and community. A three-car garage offers ample storage and convenience, while the home's setting creates a true sense of retreat. Residents of Corbett Landing enjoy exceptional community amenities, including a resort-style pool, fitness center, preserved open spaces, and thoughtfully planned natural surroundings. Ideally located near Chapel Hill, Durham, Raleigh, Chatham Park, and historic downtown Pittsboro, the community offers the perfect balance of tranquility and accessibility. Timeless architecture meets modern luxury in this exceptional custom residence by The Rexford Group, located within the prestigious estate community of Corbett Landing. Inspired by classic European country estates, this thoughtfully designed 3,825-square-foot home showcases striking brick architecture, dramatic rooflines, expansive windows, and exceptional craftsmanship throughout. Designed for both everyday living and elegant entertaining, the home features a sought-after first-floor primary suite, dedicated home office, spacious bonus room, and 4.5 beautifully appointed baths. The heart of the home is the impressive great room with soaring vaulted ceilings, creating a grand yet welcoming atmosphere filled with natural light. Thoughtfully designed living spaces flow seamlessly throughout, offering comfort, functionality, and timeless appeal. Situated on a generous 1.59-acre homesite surrounded by preserved natural beauty, mature hardwoods, and rolling topography, the property provides a rare combination of privacy and community. A three-car garage offers ample storage and convenience, while the home's setting creates a true sense of retreat. Residents of Corbett Landing enjoy exceptional community amenities, including a resort-style pool, fitness center, preserved open spaces, and thoughtfully planned natural surroundings. Ideally located near Chapel Hill, Durham, Raleigh, Chatham Park, and historic downtown Pittsboro, the community offers the perfect balance of tranquility and accessibility.

307 August Trace Dr, Pittsboro
$771,000
3 Beds ⋅ 2 Baths ⋅ 10172497 MLS ⋅ CLOSED Status
Welcome to this rare gem in the highly desirable Fearrington Village community of Pittsboro, NC. This immaculately maintained 3 bed, 2 bath single-family home sits on a quiet cul-de-sac, just a short walk from Fearrington Village's shops, restaurants, and amenities. Inside, the home features high ceilings, an open floor plan, and top-quality finishes throughout. Energy-efficient appliances keep the home comfortable and cost-conscious, while a glassed-in, climate-controlled sunroom offers a year-round retreat overlooking the backyard. With plentiful room to gather both indoors and out, it's an entertainer's dream. Outside, you'll find a meticulously cared-for garden and an extended two-car garage with ample space for vehicles, storage, and projects. Don't miss your chance to join this wonderful community, where walking paths, beautiful landscaping, and social clubs abound!

4321 Millcreek Cir, Pittsboro
$1,269,000
4 Beds ⋅ 5 Baths ⋅ 10171816 MLS ⋅ CLOSED Status
Move in just in time for summer and enjoy your own private resort—this exceptional "like new" luxury estate with a heated PebbleTec pool, hot tub, sauna, and ultimate privacy on 1.27 wooded acres is the staycation you've been dreaming of. Nestled within the gated Estates at Chapel Ridge, this custom-built masterpiece by Absolut Construction showcases exceptional craftsmanship, thoughtful design, and high-end finishes throughout. Offering 4 bedrooms, 4 full baths, and 1 half bath, every detail has been carefully curated to create a home that is as functional as it is beautiful. From the moment you arrive, the stunning custom front doors with handcrafted wrought iron detailing set the tone for the elegance that awaits inside. Soaring beamed ceilings, extensive molding, and rich architectural details add warmth and character throughout the home's spacious living areas. The luxurious main-level primary suite serves as a private retreat, complete with heated floors, a spa-inspired steam shower, soaking tub, oversized walk-in closet, and premium finishes designed for everyday comfort. A private main-floor guest suite offers ideal accommodations for visitors or multigenerational living. At the heart of the home, the gourmet eat-in kitchen features custom cabinetry, stainless steel appliances, a hooded range, and a large center island perfect for gathering with family and friends. Hidden behind custom cabinetry, a spacious walk-in pantry provides exceptional storage while maintaining the kitchen's clean, elegant design. The kitchen flows seamlessly into the formal dining room and inviting living spaces, while the screened porch offers the perfect setting to enjoy morning coffee or unwind while overlooking the pool and tranquil wooded backdrop. Designed for both convenience and recreation, the home also features an oversized three-car garage with a dedicated mini-split system for year-round comfort, an installed EV charger, an expansive laundry room and drop zone, a private fitness room with premium rubber flooring, and a relaxing in-home sauna. The expansive walkout lower level offers incredible flexibility with a dedicated office, two additional bedrooms, two full baths, a wine bar, sink, and custom cabinetry that could easily be converted into a full second kitchen. Whether accommodating extended guests, multigenerational living, or entertaining on a grand scale, this space is ready to adapt to your needs. Step outside and discover the true centerpiece of the property—an extraordinary backyard retreat featuring a heated PebbleTec pool, hot tub, covered patio, fenced yard, and mature trees that create a sense of complete privacy. Whether hosting summer gatherings or enjoying a quiet evening under the stars, this resort-inspired outdoor oasis delivers year-round enjoyment. Additional highlights include a lower-level workshop/garage perfect for hobbies and storage, abundant storage throughout the home, and a whole-home generator for added peace of mind. This one-of-a-kind estate offers the perfect combination of luxury, comfort, and privacy within one of the Triangle's most sought-after gated golf course communities.

59 Berry Patch Ln, Pittsboro
$260,000
3 Beds ⋅ 3 Baths ⋅ 10170979 MLS ⋅ CLOSED Status
This property has a private drive that is a shared driveway. There is no written road maintenance agreement. There is a perpetual 60 foot easement attached to this property. There are no well septic records for this property, the town could not locate the records from 1974.

278 Hillcrest Dr, Pittsboro
$700,000
3 Beds ⋅ 3 Baths ⋅ 10170371 MLS ⋅ CLOSED Status
Settle into Chatham County on 12 private acres designed for walking, gardening and gathering. A half-mile perimeter trail, long gravel drive, generous circular driveway, cleared and fenced backyard with patio, and fenced front garden area make the property feel private, usable, and easy to enjoy. Inside, the main level offers an easy flow with an open kitchen and dining area, living room with built-ins and a wood stove, sunroom overlooking the backyard, office/flex room, laundry with a half bath, and a separate front living room. Upstairs are three bedrooms and two baths, including a spacious primary suite with a walk-in closet and en suite bathroom. The current owners made nearly $90k in thoughtful improvements over the last four years, including both HVAC units, new windows throughout, new stainless appliances, a primary bathroom renovation, backyard patio, clearing and fencing, a new circular driveway, and more. Only two homes have sold on Shady Grove Road in the last 22 years - a reflection of a neighborhood where people tend to put down roots. The current owners improved the property with that same long-term vision in mind.

195 Shady Grove Rd, Pittsboro
$1,225,000
4 Beds ⋅ 4 Baths ⋅ 10170349 MLS ⋅ CLOSED Status
Enjoy the peace and tranquility of country living while remaining just a short drive to Pittsboro and Chapel Hill. Nestled on 15 private acres surrounded by trees and nature, this outdoor haven offers the perfect blend of relaxation and luxury. Spend the aftrenoons on the oversized screened porch complete with TV, the mornings on the dock overlooking the stocked pond and evenings around the outdoor firepit. A charming greenhouse adds to the property's appeal for gardening enthusiasts. The impressive workshop is a craftsman's dream featuring AC, bathroom and electricity--ideal for hobbies, projects, or additional workspace. Inside, this true custom home showcases exquisite finishes and timeless Old World charm throughout. Designed for main floor living, the home features a spacious primary suite, private office, and beautiful library on the main level. Upstairs, the flexible craft/flex room with private deck and stunning pond views could easily serve as a 2nd primary/4th bedroom. This one-of-a-kind property is filled with special details and thoughtful craftsmanship--see feature sheet for the full list of upgrades and amenities!

774 Running Springs Dr, Pittsboro
$990,000
4 Beds ⋅ 4 Baths ⋅ 10170344 MLS ⋅ PENDING Status
Nestled in Monterrane, one of Chatham County's most coveted neighborhoods, this exceptional custom-built home blends timeless English cottage charm with warm, inviting living spaces designed for comfort and connection. Featuring 4 bedrooms, 2 full and 2 half baths, and situated on just under 3 private acres, this cedar shake-sided home with an architectural roof showcases quality construction and attention to detail throughout with extensive custom built ins, 2 masonary fireplaces, chef's kitchen offering double Viking wall ovens, JennAir gas cooktop and ample quartz countertops. The main floor primary retreat has direct access to the brick screened porch overlooking the patio with firepit and lush private grounds that radiate peace and tranquility. Additional highlights include second floor with 2 bedrooms sharing jack and jill bath and another large bedroom/bonus with ensuite 1/2 bath, huge walk-in attic adding to the already abundant storage, irrigation and security systems and Generac whole house generator. Plus CUSTOM conditioned WORKSHOP that is ''to die for'' (currently used for high end woodworking) that offers many possibilities. A truly special property where character, craftsmanship, and nature come together in one exceptional setting. Explore neighborhood trails in this thoughtfully developed subdivision. This impeccably maintained home offers a rare opportunity. Convenient access to Chapel Hill, Pittsboro, Apex, Cary... Great location!

443 Valley Ln, Pittsboro
$2,150,000
5 Beds ⋅ 6 Baths ⋅ 10169823 MLS ⋅ ACTIVE Status
Move-In Ready Custom Masterpiece by Wagoner Homes at Firefly Overlook - 316 Firefly Overlook, Pittsboro, NC MOVE IN READY! Step into this brand-new, completed custom home by award-winning Wagoner Homes, nestled on a private 1.55-acre homesite (Homesite 28) in the exclusive Firefly Overlook community at Jordan Lake. This exquisite residence spans 4,897 square feet of thoughtfully designed heated living space, featuring 5 spacious bedrooms, 5.5 luxurious bathrooms, and exceptional storage throughout. The open-concept layout is filled with abundant natural light, showcasing impeccable craftsmanship and high-end finishes that are ready for immediate enjoyment.  Surrounded by mature hardwoods, this serene retreat offers privacy and natural beauty while being just steps from the tranquil shores of Jordan Lake. As part of an intimate boutique community of only 30 acreage homesites, it perfectly balances seclusion with convenience. Pittsboro is experiencing exciting growth with major developments on the horizon, including the transformative Chatham Park master-planned community. This expansive project will bring new homes, commercial spaces, schools, amenities, and infrastructure, enhancing the area's appeal and long-term value.  Skip the wait and uncertainties of new construction--this Wagoner Homes masterpiece is fully completed and move-in ready today. Don't miss this rare opportunity to own a luxury custom home in a prime location.

316 Firefly Overlook Rd, Pittsboro
$1,499,500
4 Beds ⋅ 5 Baths ⋅ 10168964 MLS ⋅ ACTIVE Status ⋅ Easterling Benson Fine Homes 2, Llc BLDG.
Experience luxury living in this move-in ready custom home - a 2025 Parade of Homes Gold Medal winner. Thoughtfully designed with exceptional craftsmanship and resort-style outdoor living, this home is truly a must-see. A sprawling front porch overlooks the stocked pond with tranquil water feature, creating the perfect setting to relax and unwind. Inside, the open-concept floor plan is filled with natural light and showcases stunning views from both the front and back of the home. Designed for everyday living and effortless entertaining, the chef's kitchen features high-end finishes, a spacious scullery, and walk-in pantry. The main-floor primary suite offers a private retreat, while the dedicated office on the first floor provides ideal work-from-home flexibility. Step outside and discover your own private oasis. The backyard was made for year-round enjoyment with a pool, oversized screened porch with retractable screens and heaters, and a built-in grill perfect for entertaining in every season. Additional highlights include an oversized 2-car garage plus convenient access from the pool area to a full bath and sauna. Every detail of this award-winning custom home was carefully curated to combine luxury, comfort, and functionality.

49 Harrison Pond Dr, Pittsboro
$857,000
3 Beds ⋅ 3 Baths ⋅ 10168889 MLS ⋅ ACTIVE Status
Rustically handsome and rich with character, 205 Anolis offers approximately 2,700 square feet of living space set on 12 remarkable acres in the Redbud community. Tucked at the end of a gravel road, the property unfolds into a beautiful mix of hardwood and pine forest, rolling pasture, and an intermittent stream that feeds into Temple Creek, a tributary of the Haw River. A vernal pool in the lower pasture has even served as a field study site for naturalists from the NC Museum of Natural History, where spring peepers and chorus frogs can be observed in their native habitat. The home itself is a thoughtful blend of craftsmanship and history. The original section, built in 1993, incorporates hand-adzed logs repurposed from three historic barns in Hillsborough, complemented by custom-cut timbers. A 2005 addition seamlessly integrates with the original structure and features flooring, trim, and built-in cabinetry milled on site from solid white and red oak harvested directly from the land. A striking masonry fireplace, built by well known and adored local artisan Joe Kenlan, serves as both a focal point and a highly functional heat source, capable of warming the entire home using wood from the property. Equestrian and outdoor enthusiasts will appreciate the well-planned features, including a horse barn, detached garage, and fenced pasture with Cameo high-tensile horse safety fencing. The riding ring is thoughtfully constructed with a crushed stone base and gravel surface for excellent drainage and year-round usability. The lower portion of the land, known as ''The Nursery,'' was once part of Mellow Marsh Farm, and still retains its terraces and pathways. The property has been maintained without herbicides or pesticides, preserving a healthy and natural environment. Wildlife is abundant, with frequent sightings of songbirds, raptors--including Cooper's Hawks and Barred Owls--wild turkeys, deer, foxes, and more. Black vultures have even returned to nest in the barn, and Eastern Box Turtles and Green Anoles are common sights in warmer months. From Redbud, nearby trails connect to the Haw Slopes Natural Area and the Haw River, offering the rare opportunity to hike for miles--even all the way to Bynum--without crossing a road. Landowners' covenants are in place to preserve the peace, quiet, and natural beauty of the area. 205 Anolis is a truly special property--private, storied, and deeply connected to the surrounding landscape.

205 Anolis Dr, Pittsboro
$962,500
4 Beds ⋅ 4 Baths ⋅ 10166061 MLS ⋅ CLOSED Status
The lifestyle you want and deserve awaits you in this premier 2022 ICG home in one of Pittsboro's most sought after communities, Chapel Ridge. With a refined, resort style setting including a Fred Couples golf course, inviting clubhouse and grill, beautifully maintained pool, fitness center, tennis, pickleball and scenic trails, you'll instantly feel at home in this quiet and friendly neighborhood surrounded by rolling hills and mature trees. Set privately along the 11th hole, this nearly 3,300 sq/ft ranch style home was intentionally positioned farther back on the lot to enhance privacy. A wide, upgraded driveway leads you to a distinguished double door entry. Comfortably luxurious, this home offers high ceilings, warm tones, and thoughtful upgrades. The main level features a formal dining room, a chef's kitchen with double ovens, a five burner gas range, upgraded quartz tops, plus a custom coffee bar - all opening to a bright living area with a graceful fireplace, built ins and open shelves. Wide sliders extend the living space to a large screened porch, manicured and fenced yard plus an expanded patio, all overlooking the fairway. Three main floor bedrooms include a private oversized primary suite featuring a spa like bath and tremendous custom closet. Two additional bedrooms sit separately and share a well appointed adjoining bathroom. Enter from the massive three-car garage with epoxied floors, EV charger & utility sink, and you'll find a generous drop-zone and large laundry room for your convenience. Upstairs offers a sunlit bonus room, two bedrooms, and walk in attic storage. Fully paid premium solar panels add exceptional efficiency to this stunning, serene, move-in ready home, close to downtown Pittsboro, Chapel Hill, Lake Jordan, the Haw River State Natural Area and quick ride to RTP and RDU. Whether you're looking for relaxation or a space for entertaining, Cabin Creek offers you the lifestyle you've been looking for.

119 Cabin Creek Crk, Pittsboro
$393,000
3 Beds ⋅ 3 Baths ⋅ 2540727 MLS ⋅ CLOSED Status
Chatham Forest Cottage with high-end updates in the kitchen and master bath located just a bike ride away from the hustle and bustle of downtown Pittsboro! 3 bed/2.5 bath with Master down and an upstairs bonus room perfect for your home office all on a large landscaped lot priced UNDER 400K!!! Walk to Chatham Marketplace, eclectic shopping, great eats, live music, and more! Come see for yourself why Pittsboro is truly the Heart of NC.

245 Chatham Forest Dr, Pittsboro
$459,900
2 Beds ⋅ 2 Baths ⋅ 10040081 MLS ⋅ CLOSED Status ⋅ The Inspiration BLDG.
Incredible location within the heart of Encore. The Inspiration by David Weekley presents optimized gathering spaces and the versatility to adapt to your lifestyle. Sunlight filters in through the impressive sliding glass doors to shine on the open-concept family and dining areas. The chef's kitchen provides a dine-up island, 5-burner gas cooktop and plenty of storage and prep space. A lovely screened porch adds a great place to spend time with good company and pursue leisure activities. Begin and end each day in the paradise of your Owner's Retreat, which features an en suite bathroom, super shower with roll in access and walk-in closet. The spare bedroom rests next to a full bathroom privately located in its own area of the home. Thrive in one-level living with access to a stunning Clubhouse and pool in additional to a full time, on-site lifestyle director!

79 Prospect Pl, Pittsboro
$1,500,000
5 Beds ⋅ 7 Baths ⋅ 10029982 MLS ⋅ CLOSED Status
True custom home-owner builder-so many unique features. Ideal for entertaining both in & out. Gourmet kitchen, dining & living open to 500 sq ft tiled screened porch. Wood burning fireplace both inside & out. Chef's dream-10' island, warming drawer, 6 burner gas range, built in coffee maker, ice maker, huge pantry. 1st floor office has stunning view. Primary suite has 2-sided fireplace to bedroom/bathroom, jetted tub, large shower, oversized closet. Walk out basement features custom wine wall, bedroom, flex room, 2 full baths, gym, rec room w/pool table & dart board. Step outside to flagstone patio w/stone columns. 10' ceilings, 6 zone wired music system in & out, 5'' site finished floors, builtins on each floor, solid core doors, window coverings, intercom, outdoor shower. 1950 sq ft detached garage w/4 10' garage doors-center door drive through. Upstairs-1500 sq ft apt-1 bedroom, kitchen, deck, fenced yard. 5th bedroom is in detached garage apt. Apt above garage can't be rented-primary residence use only. Seller licensed broker. PICTURES/VIDEO 5/24

151 Hawfields Dr, Pittsboro
$980,000
4 Beds ⋅ 3 Baths ⋅ 2517245 MLS ⋅ CLOSED Status
This stunning four-bedroom, three-bathroom custom home sits on a cul-de-sac lot in Chapel Ridge, adjacent to expansive undeveloped land. Experience peaceful evenings at their finest! Key features include a first-floor primary suite, open kitchen and living areas, a first-floor guest suite, an expansive screened-in porch, and a patio for outdoor relaxation. As a bonus, with an acceptable offer, you'll receive $10,000 to use as you wish!

72 Hazelwood, Pittsboro
$464,300
3 Beds ⋅ 3 Baths ⋅ 2522244 MLS ⋅ CLOSED Status
The Lakanwood! The right side of the paired villa is named for a camp owned by the family of one of our Rock Stars! Appropriately named for its lake and expansive foliage. Take a breath of fresh air in the open living space. Enjoy the convenience of a first floor Primary Suite. Retreat upstairs to find two additional bedrooms, a bathroom, and spacious loft.

39 S Explorer Ln Unit 79, Pittsboro
$330,000
3 Beds ⋅ 2 Baths ⋅ 10073442 MLS ⋅ CLOSED Status
Small-town living at its finest, come settle down in the dreamy town of Pittsboro! Only a short 15-minute walk from downtown, you'll find this 3 bed/2 bath bungalow with farmhouse charm and a big personality. With ample space to entertain, both inside and out, and enjoy hosting in the largest Dining Room you will find in its class. The kitchen features a breakfast nook, painted cabinets, and new appliances. Play, relax, and raise chickens on this large fenced-in lot and take in these breathtaking pasture views. A large, oversized garage provides ample storage, and do not miss this list of updates: New Water Heater and Deck in 2023; Roof, Kitchen Appliances, and paver Patio in 2024; and several new fixtures throughout. Revel in the charm AND the excitement of a town that has doubled its population since 2000, and for good reason; only 30 minutes from both Chapel Hill and Apex and made replete with local shops, restaurants, and community events. Your next best decision awaits!

85 W Cornwallis St, Pittsboro
$439,500
1 Beds ⋅ 1 Baths ⋅ 10066997 MLS ⋅ ACTIVE Status
Investors Welcome! The Opal is Tessera's Large 1 bedroom modern, amenity-rich condominium featuring 2 separate balconies to enjoy views of Mosaic! Interior finishes include soaring 11 ft. ceilings in main living areas highlighted by black-framed windows, luxe kitchens with Quartz countertops, soft-close wood cabinetry, expansive island, Smart appliances, LVP luxury flooring, decorative lighting with mini can lights, bathroom w tile floors & shower, designer bedroom closet, and so much more! Master with private balcony. Parking space is p-9. Storage in basement included. Roof top club house!

120 Mosaic Blvd Unit 307, Pittsboro
$1,025,000
4 Beds ⋅ 4 Baths ⋅ 10147142 MLS ⋅ CLOSED Status
Picturesque Southern Plantation-style home set on 7.134 beautiful acres in Pittsboro where stunning sunrises and glowing sunsets can be enjoyed from the second-floor walk-out balcony. Bring the horses to this manicured pasture that is almost completely fenced. 4-bedrooms, 3.5-bath home that has been recently refreshed with new paint and beautifully refinished hardwood floors as well as new carpeting in the secondary bedrooms. Inside, you'll find flexible living spaces including a dedicated office on the main floor. Great flex spaces too perfect for remote work, hobbies, or guests. Metal Roof and fiber-cement siding. Outside is a charming 20×40 wired charming red barn with overhangs on a concrete slab provides endless possibilities for horses, woodworking, gardening, or homesteading. A strong 30-GPM well supports your outdoor and household needs with ease. Randolph Fiber internet service. Peacefully tucked away--yet still conveniently located--you'll be surrounded by local agribusiness charm, including orchards, wineries, seasonal attractions, and more. With convenient access to Highways 64 and 421, this property blends peaceful country living with accessibility--an ideal retreat offering space, beauty, and versatility.

1116 Jay Shambley Rd, Pittsboro
$612,000
3 Beds ⋅ 2 Baths ⋅ 2530769 MLS ⋅ CLOSED Status
$50,000 price adjustment. More than a neighborhood, Fearrington is a lifestyle. Shops, restaurants, farm and inn located in a Colonial Williamsburg style village with all of the modern amenities that you want and need. Join a club, take a dip in the pool (optional membership), enjoy the paved trails, view the animals, visit the Farmer's Market or play in one of the many parks. This well appointed single level ranch home has an outstanding layout, expansive kitchen, new carpets, hardwood floors in the main living areas, screened porch, nearly a half acre with a wooded buffer and HOA maintained lawn and exterior cleaning. The dining room is large enough to accommodate the biggest of dining room tables, so holiday celebrations are going to be hosted here. Master bedroom has a huge walk in closet and a large shower with low threshold entry. Stainless steel refrigerator (1 year old), washer, dryer and garage storage shelves are all included. Crawlspace was recently serviced and has a new vapor barrier and dehumidifier. Check out the virtual tour. No For Sale sign in front of the house. Schedule a showing today.

4080 Woodleigh, Pittsboro
$800,000
4 Beds ⋅ 4 Baths ⋅ 10090704 MLS ⋅ CLOSED Status
Located in part of the most scenic areas of Chatham County! Relax on the wraparound front porch, you'll find plenty of elbow room on the 2+acres for gardening and bird watching. Inside you'll find a large kitchen with a huge island & pantry, airy breakfast nook, formal dining and gleaming hardwood floors on the main level. Home has 4 bedrooms and 3.5 baths. The primary bedroom is located on the main floor. There is a large rec room with wet bar and two secondary bedrooms with a jack and jill bath on the second floor. The third floor is a perfect work from home office with it's own full bath. Randolph Fiber High Speed Internet. 40 GPM Well. RV Carport with it's own concrete driveway and a great storage building, fenced yard and pretty fruit trees in the front yard. Generac 26 watt whole house generator, Leaf filter gutter guards, Permaseal 25 yr warranty sealer on porches and deck

1023 Laura Johnson Rd, Pittsboro
$1,013,457
4 Beds ⋅ 4 Baths ⋅ 10029282 MLS ⋅ CLOSED Status
Gorgeous pre-sale custom 3323 square foot, two story home built by Prewitt-Douglas Custom Homes entered for comp purposes.

44 Barn Owl, Pittsboro
$537,000
4 Beds ⋅ 3 Baths ⋅ 10104594 MLS ⋅ CLOSED Status
Notice the new price, recently reduced by the motivated sellers of 322 Bellemont Road. It is a stunning 4 bed/3 bath, nearly 3,000 sq ft home built in 2006, nestled in the coveted Chatham Forest neighborhood of Pittsboro. This residence offers a thoughtfully designed open floor plan, great features like a first-floor primary suite with tray ceilings, spacious closets, soaking tub and separate shower. Gourmet kitchen equipped with quartz countertops, stainless-steel appliances, and a large pantry perfect for large meals and entertaining. Hardwood floors gracing most of the main level, adding warmth and elegance. Inviting screened porch with gas-log fireplace, flanked by a deck and patio ideal for al fresco gatherings year-round. Bonus spaces galore: an office/den, upstairs loft, and a huge bonus room, all on over a half-acre lot. Pittsboro's quaint downtown, anchored by the historic Chatham County Courthouse (circa 1881), is just a short stroll away. Explore charming boutiques, local eats, and cultural events including the beloved Fall Festival and Christmas Parade. For literary lovers, McIntyre's Books in nearby Fearrington Village is recognized as one of the South's top independent bookstores. For outdoor adventure, residents enjoy easy access to Jordan Lake's boat ramps and hiking trails, as well as Deep River Park's scenic riverfront trails and historic bridge. Music and arts lovers will appreciate the Shakori Hills GrassRoots Festival just minutes away in scenic woods outside town. Pittsboro Elementary, Horton and Pollard Middle Schools, Northwood and Seaforth High Schools, plus Central Carolina Community College. Commuters enjoy easy highway access to Chapel Hill (17 mi), Raleigh (34 mi), and beyond. 322 Bellemont Road blends functional elegance with community charm. With spacious living spaces, modern amenities, abundant bonus rooms, and a peaceful wooded lot, this home is ideal for both day-to-day living and hosting gatherings. Best of all, it's only steps from parks, trails, downtown delights, and cultural venues. Schedule your showing today and make this Pittsboro treasure your home!

322 Bellemont Rd, Pittsboro
$2,100,000
4 Beds ⋅ 6 Baths ⋅ 10084663 MLS ⋅ CLOSED Status
This modern private estate is a true embodiment of the Tony Frazier Design philosophy where every element is crafted with intention and artistry. ''Our bespoke process is rooted in meticulous attention to detail—from live sketching with clients to carefully considering the topography of the land to sourcing only the finest high-grade materials.'' From the moment you arrive, you're welcomed by striking stucco Dutch parapets and a floating staircase that sets the tone for the home's architectural brilliance. Inside, 5-inch hardwood floors and abundant natural light lead you through an open, airy layout designed for both everyday comfort and elegant entertaining. The exceptional chef's kitchen features built-in maple shelving, premium Café appliances, a Thermador range, and an incredible butler's pantry equipped with a second fridge and ice maker. Step outside to a spacious deck that overlooks a serene, landscaped backyard—complete with a UV-filtered pool, hot tub, outdoor shower, and thriving farm-to-table gardens. Raised beds offer a bounty for the home chef, with mature fig trees, blueberry bushes, raspberry vines, asparagus, and more. Perfectly situated near Jordan Lake and the Haw River, outdoor enthusiasts will appreciate the easy access to nature, while an indoor climbing wall and majestic lap pool offer year-round recreation. The thoughtful floor plan includes multiple spaces to gather or unwind whether enjoying movie nights, ping pong games, or casual conversations with loved ones. Every inch of this home was designed for comfort, excellence, and tranquility—an exceptional private retreat that remains close to everything.

336 Timberline Dr, Pittsboro
$490,000
3 Beds ⋅ 3 Baths ⋅ 10092005 MLS ⋅ CLOSED Status
Say hello to your future happy place! This Happy B floorplan by Garman Homes if full of personality and packed with all the things that make a house feel like home. Move in ready January 2026, this beauty is tucked away on a cozy cul-de-sac just steps from the walking train- perfect for morning stolls or evening dog walks. Inside you'll find our timeless Classic White Button Down interior package- clean, crips and effortlessly stylish. The gourmet kitchen is ready for everything from popcorn movie nights to your signature holiday spread! Out back- a wooded view that feels like your own private retreat- Oh did I mention a screened in back porch too?! Ready to be happy? This one's got your name on it!

328 Beacon Dr, Pittsboro
$1,008,486
4 Beds ⋅ 5 Baths ⋅ 2456114 MLS ⋅ CLOSED Status
Pre-sale for comp purposes. BUILDER HAS MORE LOTS AND PLANS

138 Colonial Trl, Pittsboro
$1,034,700
4 Beds ⋅ 4 Baths ⋅ 10046543 MLS ⋅ CLOSED Status ⋅ Upton & Co. Inc. BLDG.
Builder Currently Offering $25K to Use as You Choose on Acceptable Offers with Close Date of April 15th or Sooner!! Closing Costs/Upgrades/Appliances...!! Limited Time Incentive!! Stately Brick Accented Home w/Beautiful Window Accented Lighted Staircase Flooding the Home with Natural Lighting Not Just There But Throughout!! Dramatic 2 Story Foyer w/2nd Floor Overlook!! Primary w/Sep Tub & Shower w/Large Closet w/Direct Laundry Rm Access on 1st!! Private Study w/French Doors!! Gourmet Kitchen w/Speakers & Scullery w/Sink & Cabinets to Ceiling!!!! Gas Range & 2nd Wall Oven for Double Oven Effect!! Refrigerator!! Dining Rm Overlooking Covered Back Porch w/2 Panel Slider Access to Screen Porch!! 18 x19 11' Coffered Light Accented Ceiling Family Rm w/FP & Built ins w/4 Panel Slider!! Trexx Flooring, Speakers & TV Ready Screen Porch!! 2nd Flr Features 3 Nice Size Bedrooms ALL w/Full Bath Access!! Huge Bonus & ALOT of Attic Space!!! Sealed Garage Floor w/ Insulated Garage Doors!! Fenced Level Back Yard Too!! Whuff Whuff!! Gas Heat, Logs, Range, & Tankless Water Heater!! Trails, Shopping, Events Lawns, Parks, & YMCA & Jordan Lake just Minutes Away!! Eco Select Certified!!

51 Autumn Gate St, Pittsboro
$650,000
2 Beds ⋅ 3 Baths ⋅ 10096693 MLS ⋅ CLOSED Status
Everything you want for your new home! This home overlooks Camden Park which is lovely, and just a few blocks walk to Fearrington Village Center where all the activities happen! First floor living PLUS a second primary suite on the second floor! The living room has soaring ceilings and large windows; wood plank floors and a gas fireplace. The dining room has built in cabinets and display shelves plus a wall of windows with sliding door overlooking the courtyard. 2018 the kitchen and bath projects accomplished really fantastic living spaces! The kitchen has white cabinets with a wood stained island. Upper cabinets go to the ceiling with the upper most cabinets outfitted with glass fronts and lighting to show off your treasures. A separate coffee/wine bar is great for entertaining. Undercabinet light, soft close doors/drawers and all roll out drawers make this kitchen pure joy. This home has been upgraded to have two complete ensuites and an office. Both ensuites are beautiful with large walk-in showers, upgraded lighting and cabinetry. Both ensuites have large closets with complete organizing systems. The private courtyard will afford you lots of outdoor entertaining space. Come take a look, you are going to love it!

3 Yancey, 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 .

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