Pittsboro Homes for Sale

Pittsboro Homes for Sale

Welcome to Pittsboro, a charming town located in Chatham County, North Carolina, USA. Known for its picturesque landscapes and friendly community, Pittsboro offers a perfect blend of small-town charm and modern amenities.

For those looking to call Pittsboro home, there are plenty of real estate options to choose from. Whether you are in the market for a cozy single-family home, a spacious townhouse, or a sprawling estate, Pittsboro has something for everyone. With a range of architectural styles and price points, you are sure to find the perfect home to suit your needs and lifestyle.

Pittsboro's real estate market, represented by True Homes, is vibrant and diverse, catering to a wide range of preferences and budgets. From historic homes with character to newly built properties with modern features, there is no shortage of options for buyers in Pittsboro.

Living in Pittsboro means enjoying a laid-back lifestyle while still being within easy reach of major cities like Raleigh and Durham. With its vibrant arts scene, local shops and restaurants, and proximity to outdoor recreational opportunities, Pittsboro truly offers the best of both worlds.

If you are considering making Pittsboro your home, now is the perfect time to explore the available homes for sale and find your dream property in this charming town.

Newest Pittsboro Homes for Sale

$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
$559,000
4 Beds ⋅ 3 Baths ⋅ 10182271 MLS ⋅ ACTIVE Status
Move right into this beautifully updated 4-bedroom, 2.5-bath home in the desirable Potterstone Village community! Situated on a private, beautifully landscaped 0.44-acre fenced lot, this turnkey home offers 2,665 square feet of thoughtfully designed living space with extensive recent updates throughout. The entire interior was freshly painted in July 2026 and features gorgeous refinished hardwood floors (July 2026) on the main level, brand-new carpet on the stairs and second floor, and an exterior freshly painted in October 2025. The spacious floor plan is perfect for everyday living and entertaining, while the bright sunroom—converted & featuring windows installed in 2019—provides the perfect place to relax year-round, and the sunroom furniture conveys! The updated primary suite includes a new vanity cabinet, faucets, and a semi-frameless glass shower enclosure, creating a fresh, spa-like retreat. The kitchen has also been updated with a new oven, dishwasher and microwave (2026), making this home truly move-in ready. Step outside to enjoy the private backyard oasis complete with lush landscaping, a patio, and a storage shed with upgraded drainage completed in 2019. With too many improvements to list, this meticulously maintained home offers peace of mind and exceptional value. Enjoy neighborhood amenities including a community pool, clubhouse, and scenic pond, all just minutes from historic downtown Pittsboro, shopping, restaurants, and convenient access to US-64, US-15/501, and NC-87. Turnkey, beautifully updated, and ready for its next owner—this is one you won't want to miss!

538 May Farm Rd, Pittsboro
$799,900
4 Beds ⋅ 3 Baths ⋅ 10182238 MLS ⋅ ACTIVE Status
CUSTOM BRICK HOME IN CHAPEL RIDGE! Located on a private homesite in one of Pittsboro's premier golf course communities, this thoughtfully designed home offers more than 3,500 square feet of living space, quality craftsmanship, and exceptional indoor-outdoor living. Backing to additional wooded acreage, this property enjoys scenic natural views and a rare opportunity to purchase the adjacent lot separately for added space and flexibility. Inside, rich hardwood flooring, detailed millwork, plantation shutters, and custom built-ins create timeless character throughout. The spacious living room features a fireplace and flows seamlessly into the breakfast area and well-appointed kitchen, complete with abundant cabinetry, generous prep space, and pantry storage. The main-level primary suite offers a spacious bedroom, dual vanities, a soaking tub, walk-in shower, and large walk-in closet. Additional main-floor spaces include a formal dining room and dedicated office. Upstairs, three secondary bedrooms, a large bonus room, and a dedicated storage room provide flexibility for a variety of uses. Enjoy year-round outdoor living from the oversized screened porch with Trex decking overlooking the wooded backdrop. Additional highlights include a walk-in crawl space with exceptional storage, tankless water heater, water filtration system, and an oversized three-car garage. Conveniently located near Chapel Ridge Golf Club, shopping, dining, parks, and major commuter routes, this property combines spacious living, quality construction, and a desirable community setting in the heart of Chatham County.

915 Cabin Crk, 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
$585,000
4 Beds ⋅ 3 Baths ⋅ 10181726 MLS ⋅ ACTIVE Status
Set on an oversized lot, this beautifully appointed home offers the perfect blend of comfort, functionality, and curb appeal. Relax on the extended front porch, an inviting space to enjoy your morning coffee, greet neighbors, or unwind in the evening. Inside, the bright, open-concept floor plan is enhanced by custom built-in cabinetry around the fireplace in the living room, adding both character and practical storage while creating a stunning focal point for everyday living and entertaining. Designer finishes and quality craftsmanship are evident throughout the home. The spacious primary suite is a true retreat, featuring a luxurious ensuite bath with a freestanding soaking tub and beautiful tile. Every detail has been thoughtfully selected to create a warm, elegant atmosphere. Located in the award-winning Chatham Park community, you'll enjoy 30 plus miles of trails and bike paths, parks, playgrounds, and easy access to shopping, dining, entertainment, and all that charming downtown Pittsboro has to offer. Chatham Park's Knight Farm Community Park has a splash pad, playground, dogpark, zipline and plenty of open outdoor green spaces. Or join Paddles or Chatham Park YMCA right around the corner, for easy access to pools and pickleball. And if you happen to have a pre-schooler, you can walk to Amazing Explorers Academy. This move-in ready home combines premium upgrades, generous outdoor space, and an unbeatable location for the best of modern North Carolina living.

268 Mindees Ln, Pittsboro
$450,000
3 Beds ⋅ 2 Baths ⋅ 10181660 MLS ⋅ ACTIVE Status
Beautifully designed contemporary home on a naturally wooded lot in Fearrington Village. Vaulted ceilings, skylights, and abundant windows fill the home with natural light and frame views of the wooded setting. The front door opens to an entry foyer, leading to a living room with a fireplace and a dining area with sliding glass doors to the rear deck. The spacious kitchen includes a pantry and gas stove, with an adjoining laundry room that offers a second pantry. The main-level primary bedroom features a walk-in closet and full bathroom. Upstairs are two additional bedrooms and another full bath. Recent updates include fresh interior paint and new bedroom carpet. Exterior storage closet included.

4 Matchwood, Pittsboro
$789,000
3 Beds ⋅ 4 Baths ⋅ 10181569 MLS ⋅ ACTIVE Status
A Fearrington Village sanctuary in the popular Bush Creek neighborhood with an idyllic garden and .81 acre lot. One-level and spacious, this home features natural light and an ideal floorplan. Wonderful flow from the kitchen with center island to the attached open dining room and living room that leads out to a fantastic all-season room. The lovely woodland creek view from the all-season room evokes the serenity of a mountain retreat. Ample sized primary bedroom and a private guest bedroom which could be a second primary. High ceilings, built-ins and a warm fireplace to gather around in the living room. Two half baths and a large laundry room for your convenience. The lot is landscaped for both beauty and ease and includes an expertly designed patio garden area with smart irrigation. Enjoy the established flora and grow your own in this botanical oasis. A remarkable place to call home in the tranquil, treasured community of Fearrington Village.

804 Millcroft, 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
$998,875
4 Beds ⋅ 3 Baths ⋅ 10181186 MLS ⋅ ACTIVE Status ⋅ Normont BLDG.
Under Construction! Enjoy peaceful living on a 1+ acre wooded homesite in the beautifully designed Normont. This open-concept home features a first-floor owner's retreat, spacious designer kitchen, expansive family room, flexible secondary bedrooms, and a covered rear porch—perfect for taking in the private, tree-lined surroundings. The ideal combination of modern comfort, functional living, and the privacy of a spacious wooded homesite. Enjoy peaceful living on a 1+ acre wooded homesite in the beautifully designed Normont. This open-concept home features a first-floor owner's retreat, spacious designer kitchen, expansive family room, flexible secondary bedrooms, and a covered rear porch—perfect for taking in the private, tree-lined surroundings. The ideal combination of modern comfort, functional living, and the privacy of a spacious wooded homesite.

236 Flatiron Frst Dr, Pittsboro
$1,275,000
4 Beds ⋅ 5 Baths ⋅ 10181067 MLS ⋅ ACTIVE Status
Privately tucked away at the end of a quiet cul-de-sac beneath a mature canopy of hardwoods, this extraordinary custom estate presents a rare opportunity to create a truly personalized luxury residence on four private acres within Pittsboro's exclusive Fox Oak community. Now is the ideal time to make your vision a reality. As construction begins, discerning buyers will have the unique opportunity to collaborate directly with the builder to personalize finishes, refine living spaces, and tailor select design elements to complement their lifestyle. Inspired by timeless modern farmhouse architecture with refined estate-style influences, this exceptional home will offer 4,332 heated square feet and more than 5,473 square feet under roof. Designed to balance elegant entertaining with comfortable everyday living, the thoughtfully crafted floor plan features four bedrooms, four-and-a-half baths, and expansive open living spaces filled with natural light. At the heart of the home, the dramatic great room flows effortlessly into a designer kitchen centered around an oversized gathering island. An exceptional scullery pantry with additional cabinetry, countertops, and dedicated prep space provides both beauty and function, making entertaining seamless while keeping the main kitchen pristine. Distinctive architectural details elevate every space, including a welcoming wraparound front porch, cathedral-ceiling library, striking statement staircase, spacious loft retreat, two private offices, and a generous bonus room ideal for a media room, fitness studio, recreation space, or additional guest accommodations. The luxurious primary suite is designed as a peaceful private retreat, complete with dual vanities, a freestanding soaking tub, oversized walk-in shower, and an expansive custom walk-in closet with built-in wood shelving. The surrounding four-acre homesite offers exceptional privacy while providing ample room for future outdoor amenities. Buyers can work directly with the builder to discuss potential enhancements, including a custom pool, outdoor kitchen, fire feature, sports court, gardens, or additional entertaining spaces—creating an estate that is as impressive outdoors as it is inside. Located within the prestigious Fox Oak community, this is a rare opportunity to build a one-of-a-kind custom luxury home that combines exceptional craftsmanship, timeless architecture, and the freedom to personalize nearly every detail in one of Pittsboro's most desirable settings.

97 Fox Oak Trl, 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
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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 .