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View All Latest Pittsboro 3500+ Sq. Ft. Properties for Sale

$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
$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
$1,300,000
5 Beds ⋅ 4 Baths ⋅ 10181359 MLS ⋅ PENDING Status
ENTRY FOR COMPS ONLY: Welcome to exceptional living in Fearrington Village! This stunning Green-certified Craftsman-style residence, built by Homes by Dickerson, showcases the highly sought-after custom Lakewood floor plan and offers more than 4,200 square feet of thoughtfully designed living space on a beautifully landscaped one-acre homesite. Designed for both everyday comfort and elegant entertaining, the open-concept floor plan features four spacious bedrooms, 3.5 baths, and exquisite hardwood and tile flooring throughout. The heart of the home is a chef's dream kitchen complete with marble countertop, an oversized center island, natural gas range with professional hood, Energy Star appliances, double ovens with warming tray, built-in microwave, walk-in pantry, and seamless flow into the breakfast area and family room. The luxurious owner's suite provides a private retreat with a spa-inspired bath featuring a large soaking tub, walk-in shower, and a generous walk-in closet. A private guest suite on the main level offers comfort and convenience for visitors, while the second-floor bonus room and walk-in storage provide flexible living space for recreation, work, or hobbies. Architectural details abound, including custom built-in bookshelves, home theatre system, separate formal dining room, natural gas fireplaces in both the family room and study, utility room with soaking tub, and abundant storage throughout. Step outside to enjoy the peaceful setting from the screened porch overlooking the private wooded backyard, or entertain on the elegant patio. The professionally maintained grounds feature an irrigation system, mature landscaping, rain gutters, and a dramatic circular concrete driveway leading to the attached two-car garage. Built with quality, efficiency, and sustainability in mind, this home includes a tankless water heater, sealed crawl space, low-flow plumbing fixtures, two booster pumps, fiber cement and stone exterior, natural gas service, ceiling fans, and a 30-year shingle roof warranty. A transferable termite policy through Capital Pest Control adds additional peace of mind. Ideally located with easy access to neighborhood trails and Fearrington Market Place, this exceptional property is just minutes from UNC and Duke hospitals, premier dining, shopping, and all that the Triangle has to offer. Experience the perfect blend of luxury, craftsmanship, energy efficiency, and timeless design in one of the area's most desirable communities. Entry for Comps Only: Welcome to exceptional living in Fearrington Village! This stunning Green-certified Craftsman-style residence, built by Homes by Dickerson, showcases the highly sought-after custom Lakewood floor plan and offers more than 4,200 square feet of thoughtfully designed living space on a beautifully landscaped one-acre homesite. Designed for both everyday comfort and elegant entertaining, the open-concept floor plan features four spacious bedrooms, 3.5 baths, and exquisite hardwood and tile flooring throughout. The heart of the home is a chef's dream kitchen complete with marble countertop, an oversized center island, natural gas range with professional hood, Energy Star appliances, double ovens with warming tray, built-in microwave, walk-in pantry, and seamless flow into the breakfast area and family room. The luxurious owner's suite provides a private retreat with a spa-inspired bath featuring a large soaking tub, walk-in shower, and a generous walk-in closet. A private guest suite on the main level offers comfort and convenience for visitors, while the second-floor bonus room and walk-in storage provide flexible living space for recreation, work, or hobbies. Architectural details abound, including custom built-in bookshelves, home theatre system, separate formal dining room, natural gas fireplaces in both the family room and study, utility room with soaking tub, and abundant storage throughout. Step outside to enjoy the peaceful setting from the screened porch overlooking the private wooded backyard, or entertain on the elegant patio. The professionally maintained grounds feature an irrigation system, mature landscaping, rain gutters, and a dramatic circular concrete driveway leading to the attached two-car garage. Built with quality, efficiency, and sustainability in mind, this home includes a tankless water heater, sealed crawl space, low-flow plumbing fixtures, two booster pumps, fiber cement and stone exterior, natural gas service, ceiling fans, and a 30-year shingle roof warranty. A transferable termite policy through Capital Pest Control adds additional peace of mind. Ideally located with easy access to neighborhood trails and Fearrington Market Place, this exceptional property is just minutes from UNC and Duke hospitals, premier dining, shopping, and all that the Triangle has to offer. Experience the perfect blend of luxury, craftsmanship, energy efficiency, and timeless design in one of the area's most desirable communities.

4228 Henderson Pl, 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
$1,275,000
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
$2,475,000
5 Beds ⋅ 8 Baths ⋅ 10180609 MLS ⋅ ACTIVE Status
Welcome to this exceptional new single-family residence in The Summit. This five-bedroom, 6.5-bathroom home offers abundant space for versatile living arrangements and entertaining. Set on a generous 1-Acre home site near the top of Burnette Mountain, the property provides ample outdoor space and privacy. The residence features two downstairs bedrooms, a grand Formal Dining Room, Study, Scullery and a breakfast area. The primary bedroom features to very spacious His/her Closets. A three-car garage, ensures convenient vehicle storage and protection. Located in The Hamptons Summit community, this home presents an outstanding opportunity for those seeking quality and substance in their real estate investment.

95 Mountaintop Cir, Pittsboro
$2,595,000
4 Beds ⋅ 6 Baths ⋅ 10180435 MLS ⋅ ACTIVE Status ⋅ The Glenmore BLDG.
Welcome to The Glenmore, an exquisite custom estate home built by award-winning Hearthstone Luxury Homes, on Lot 2 in the prestigious Firefly Overlook at Jordan Lake community in Pittsboro. This stunning residence, currently under construction, spans 5,359 square feet with 4 bedrooms, 5.5 bathrooms, and a 3-car garage on a beautiful 1.62-acre wooded homesite. Perfectly blending architectural elegance with modern luxury, this home is also featured in this year's Triangle Parade of Homes—don't miss your chance to experience it! Step inside to a spacious great room featuring a gas fireplace and a dramatic wall of sliding glass doors opening to a covered porch with an outdoor kitchen and motorized screens—ideal for year-round outdoor entertaining. The gourmet chef's kitchen boasts an expansive island, walk-in pantry, and casual dining area, making it perfect for both everyday living and grand gatherings. The main-level primary suite offers a serene retreat with a spa-inspired bath and oversized walk-in closet. A first-floor guest suite provides additional privacy and convenience for visitors. Upstairs, discover two more bedrooms with private baths, a flexible bonus room with wet bar, and a versatile office (or potential fifth bedroom), plus ample unfinished storage space for future customization. Firefly Overlook is a boutique luxury community of just 30 private homesites (1.6-5+ acres) nestled amid rolling hills and streams, with easy walking distance to Jordan Lake. Enjoy nearby Vista Point Park with hiking trails, beach access, picnic areas, and boat launch—offering the ultimate in lakeside living while being conveniently located to Chatham County schools and amenities. This is luxury living at its finest in one of the Triangle's most sought-after new communities. Schedule your private tour today!

41 Firefly Overlook Rd, 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
$1,434,096
4 Beds ⋅ 5 Baths ⋅ 10179914 MLS ⋅ PENDING Status ⋅ Oakmont - Custom BLDG.
Pre-sale Oakmont with 4 car garage, fireplace on rear porch, upgrades throughout.

68 Loggers Run, 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
$1,199,000
4 Beds ⋅ 5 Baths ⋅ 10179589 MLS ⋅ ACTIVE Status ⋅ Hamilton BLDG.
Under Construction - Ready in February 2027. Nestled on a private 1.14-acre wooded homesite in the highly sought-after Corbett Landing community, this Hamilton Modern Farmhouse offers exceptional craftsmanship, thoughtful design, and elevated custom finishes throughout. Designed for both everyday living and entertaining, this home features a highly desirable main-level layout with a luxurious primary suite, private guest bedroom, dedicated study, and expansive walk-in pantry. The open-concept living spaces showcase custom details throughout, including upgraded trim, elegant wainscoting, built-in cabinetry, designer wallpaper in the powder room, and a stunning upgraded fireplace with a stained white oak mantle. The gourmet kitchen is thoughtfully appointed with cabinetry extending to the ceiling, upgraded quartz countertops, additional cabinetry, and premium finishes designed for both beauty and functionality. The main-level laundry room provides exceptional convenience with additional cabinetry, countertop space, and a dedicated sink. The luxurious primary suite features a spa-inspired bath with upgraded tile selections, premium countertops, upgraded plumbing fixtures, and durable hard flooring. The second floor offers incredible flexibility with two additional bedrooms, a spacious flex room, a large recreation room, and a walk-in attic providing abundant storage space. Every detail has been carefully selected, from upgraded tile and countertops throughout to designer plumbing fixtures and custom finishes that elevate the home's overall feel. Surrounded by mature trees and offering a rare sense of privacy, this exceptional home combines modern farmhouse charm with the quality and craftsmanship expected in Corbett Landing. $30,000 use as you choose incentive with use of preferred lender and attorney. To be used toward rate buy down, closing costs, or upgrades.

375 Gaines Trl, Pittsboro
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 10179012 MLS ⋅ ACTIVE Status
If you've been looking for true main-level living without giving up space, this one hits a combination that's hard to find. Set on just over an acre with a private, wooded backdrop, this 4,200 square foot, 4 bedroom, 3.5 bath craftsman built in 2015 offers a layout that lives comfortably day to day while still giving you room to spread out when you need it. The main level is anchored by an open kitchen, family room, and dining area that flows naturally together, with a large island, gas range, double ovens, and built-in appliances creating a space that works just as well for everyday living as it does when you have people over. Interior details carry throughout with coffered and beamed ceilings, built-ins, crown molding, and a wet bar that adds both function and character, and it's clear this home has been maintained at a level you don't see often, the kind where a home inspector might walk through and wonder how he's going to earn his fee. The primary suite and additional bedrooms on the main level offer the convenience many buyers are looking for, while upstairs becomes a true second living space with a large bonus room and its own wet bar, creating the perfect setup for entertaining, movie nights, or a completely separate hangout space. In addition, the home offers multiple flex spaces that can adapt to office, workout, or hobby use, along with several oversized storage closets and a large unfinished walk-in attic that gives you storage capacity most homes simply cannot match. Outdoor living is just as strong with covered, screened, and open areas that extend how the home lives, all overlooking a private, tree-lined setting. A three-car garage, outbuildings, and a usable lot round out the functionality, creating a home that offers flexibility, privacy, and space in a way that stands out in this price range in Pittsboro.

79 Lindsay Burke Pl, Pittsboro
$1,315,000
5 Beds ⋅ 4 Baths ⋅ 10178088 MLS ⋅ ACTIVE Status
Views of # 9 and #1 Fairways! Triple A Homes, a local expert custom home building company is proud to offer this 5 Bedroom 4 Bath beauty with a very oversized 2 car courtyard garage with additional cart garage for your favorite golf cart! This home has a friendship entry in addition to the large front porch. Guest suite and Master on main, Open feel with two -story Great Rm. Large breakfast nook. You can easily have dining room converted to 1st floor office. Double door entry. We love the upstairs stairway tucked away in the side wing of the home. The bonus room upstairs is absolutely massive. Excellent Cul-De-Sac Location on the 9th hole! Enjoy easy access to the awesome Golf Course and Amenity Center with Pool, Tennis, Soccer, Gym, Clubhouse, Pickle Ball, Basketball and a whole lot more. Several new amenities are available nearby.

25 Blackhorn Ct, Pittsboro
$1,117,210
4 Beds ⋅ 4 Baths ⋅ 10177745 MLS ⋅ PENDING Status
Pre-Sale Shelby for comp purposes.

341 Gaines Trl, Pittsboro
$1,575,000
4 Beds ⋅ 5 Baths ⋅ 10177168 MLS ⋅ ACTIVE Status
If peace, privacy, and luxury are at the top of your wish list, than this exceptional home by ICG Homes delivers. Tucked away on one of the quietest cul de sac streets in sought after Ryan's Crossing with room for a pool, this thoughtfully designed home offers a highly functional floor plan with endless possibilities for entertaining, working from home, hosting guests, and everyday living. The main level features a luxurious first floor owner's suite, plus private guest suite, dedicated study, formal dining room, and an expansive family room that flows seamlessly into the chef's kitchen and screened porch with fireplace. Beautifully appointed with premium Thermador appliances, an oversized center island, and a spacious walk in pantry, the kitchen is designed to impress while making everyday living effortless. The spa inspired owner's bath and oversized walk in closet create a private retreat you'll look forward to every day, while abundant storage throughout the home ensures there's a place for everything. Upstairs, you'll find spacious secondary bedroom suites, a large game room, media room, and generous walk in storage. A screened porch and three car garage complete this remarkable home, offering the perfect setting to relax and enjoy the peaceful surroundings. Ryan's Crossing is one of the Triangle's premier luxury communities, surrounded by acres of protected conservation land with scenic walking trails, yet just minutes from Chapel Hill, UNC, Duke, RTP, Jordan Lake, and the growing amenities of Pittsboro. Photos are of a previously built by ICG Homes and are for illustrative purposes only. Square footage is based on architectural plans, & property taxes are based on vacant lot.

377 Lila Dr, Pittsboro
$3,195,000
5 Beds ⋅ 6 Baths ⋅ 10176685 MLS ⋅ ACTIVE Status
Luxury, privacy, and timeless elegance come together in this extraordinary custom-built estate on 2 private acres just minutes from Jordan Lake. Designed to impress at every turn, this one-of-a-kind home is filled with natural light from stunning oversized windows that showcase every beautiful space. Offering 5 spacious bedrooms and 5.5 bathrooms, including a luxurious primary suite and private mother-in-law suite on the main level, this home was thoughtfully designed for both everyday living and unforgettable entertaining. The chef's kitchen, complete with a butler's kitchen, flows effortlessly into the open living spaces, while the upstairs loft, oversized bonus room, and private balcony provide endless room to relax, work, or play. Step outside to your own resort-style backyard featuring a sparkling pool, peaceful surroundings, and the privacy you've been searching for. Every detail has been carefully crafted to create a home that feels like a private retreat while keeping you just minutes from Jordan Lake and everyday conveniences. This is more than a place to live. It is the kind of home you'll never outgrow, never want to leave, and never forget.

196 Mountaintop Cir, Pittsboro
$850,000
5 Beds ⋅ 5 Baths ⋅ 10176436 MLS ⋅ PENDING Status
Rare Opportunity in Gated Chapel Ridge Estates! Situated on nearly a full acre, this exceptional 4,397-square-foot home offers a rare combination of generous living space, premium lot size, and resort-style amenities that are difficult to find at this price point in Chatham County. A dramatic two-story foyer with wainscoting and elegant iron spindle staircase welcomes you inside! Custom molding throughout the home adds timeless character, while the formal dining room showcases a coffered ceiling and extensive wainscoting. A private office with French doors provides the perfect work-from-home space. The heart of the home is the expansive chef's kitchen featuring granite countertops, a large center island, gas cooktop, double wall ovens, stainless steel appliances, under-cabinet lighting, tile backsplash, walk-in pantry, butler's pantry, and abundant cabinetry! The kitchen flows seamlessly into the family room with gas fireplace, adjoining hearth room, and breakfast area—creating exceptional everyday living and entertaining spaces. A convenient drop zone with built-in storage keeps life organized. Designed for today's lifestyle, the versatile floor plan features dual primary suites, including a spacious main-level guest/in-law suite with a private bath, walk-in closet, and sitting area—ideal for multigenerational living or long-term guests. Upstairs, the luxurious primary retreat boasts a tray ceiling, sitting area, an impressive walk-in closet, and a spa-inspired bath with separate vanities, soaking tub with tile surround, oversized tiled shower with bench, and private water closet! Upstairs, two secondary bedrooms with walk-in closets share a Jack-and-Jill bath, while a third bedroom enjoys its own ensuite bath and walk-in closet! A spacious media room is ready for movie nights, game days, or additional recreation space. Outdoor living is equally impressive with a covered front porch, 18' x 12' screened porch, and 22' x 12' deck, providing nearly 600 square feet of outdoor living space overlooking the private backyard. Additional highlights include a whole-house generator (2021) for peace of mind. Located within the gated section of Chapel Ridge Estates, residents enjoy access to resort-style amenities including the Fred Couples-designed championship golf course, clubhouse, fitness center, pool, tennis and pickleball courts, basketball, volleyball, playground, and scenic walking trails. Conveniently located near Jordan Lake, Chapel Hill, Pittsboro, and the Triangle, this home offers luxury living with the perfect balance of privacy, recreation, and accessibility. Ask about the community's golf memberships and discover why Chapel Ridge is one of Chatham County's most desirable places to call home.

94 Mossy Creek Ct, Pittsboro
$1,450,000
4 Beds ⋅ 5 Baths ⋅ 10174472 MLS ⋅ ACTIVE Status
Set on a breathtaking 2.5-acre wooded homesite just moments from Jordan Lake, Seaforth High School, and the vibrant heart of the Triangle, this extraordinary custom estate is a showcase of timeless luxury, exceptional craftsmanship, and inspired design. Scheduled for completion in October 2026 after being showcased in the Chatham County Parade of Homes, the residence has been thoughtfully envisioned to blend sophistication with warmth, creating spaces that are both grand and inviting. Expansive windows fill the home with natural light, further emphasizing carefully curated finishes and architectural details that elevate everyday living. At the heart of the home, a spectacular designer kitchen is crafted for gathering and celebration. An oversized statement island anchors the space, complemented by bespoke custom cabinetry and premium Café™ smart appliances that combine professional-grade performance with enduring style. The main-level owner's retreat serves as a private sanctuary, featuring a spa-inspired bath designed for relaxation and renewal. A dedicated guest suite and ensuite baths for every bedroom help ensure comfort and privacy for family and guests. Outdoor living is equally impressive. Vaulted screened porches and elegant outdoor entertaining spaces create a seamless connection to the natural surroundings, offering peaceful, wooded views and a perfect setting for enjoying Carolina evenings year-round. Nestled within an enclave of distinguished custom homes, this exceptional property offers the rare advantage of no HOA and minimal covenants, preserving both privacy and community character. Encompassing 3,688 heated square feet and 5,025 square feet under roof, the home reflects the builder's renowned commitment to quality, craftsmanship, and attention to detail. Located in one of the region's most desirable areas, it provides the perfect balance of tranquility, convenience, and luxury living. Current photographs showcase both construction progress and the remarkable level of artistry that will define the completed residence.

35 Big Bear Dr, Pittsboro
$1,190,000
4 Beds ⋅ 4 Baths ⋅ 10174176 MLS ⋅ ACTIVE Status
This thoughtfully designed 3,505 sqft home features an open and airy layout with 10 ft ceilings on the main level and 9 ft ceilings on the second floor, creating a bright and expansive feel throughout. The home offers 4 spacious bedrooms and 3.5 bathrooms, all secondary bedrooms are en-suite for ultimate comfort and privacy, and the full unfinished basement allows for creativity and possibilities. The chef's kitchen is a true centerpiece, showcasing ceiling-height cabinetry, quartz countertops, stainless steel Bosch appliances, and a 36-inch gas range. A separate scullery kitchen adds both functionality and elegance. The kitchen flows seamlessly into the main living area, highlighted by a 48-inch gas fireplace and large sliding patio doors that open to a backyard with wooded privacy. Additional features include hardwood flooring throughout the main living areas, carpet in the bedrooms, a 3 car garage, and a tankless water heater for efficiency. Located in Chapel Ridge, residents enjoy resort-style amenities including a clubhouse, pool, fitness center, pickleball courts, tennis courts, volleyball, basketball, a soccer field, and of course, championship golf.

79 Lookout Rdg, 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
$1,089,999
4 Beds ⋅ 4 Baths ⋅ 10172053 MLS ⋅ ACTIVE Status
Remarkable New Construction! Gorgeous Retreat in Popular Chapel Ridge Golf Community on .53 acres. Custom-built Home with an Amazing Floorplan and all the Custom Styles you desire. 4 Bedrooms, 3.5 Bathrooms with Master Bedroom and Secondary Bedroom on the Main Level. Additional 2 Bedrooms on the Second Floor plus Loft/2nd Family Rm and Additional Bonus Room. 10 ft Ceilings throughout downstairs/ 9 ft. upstairs. Stunning! Massive Gourmet Kitchen w/ Quartz Countertops, Custom Double Cabinets and Updated Appliances, including 2 Large Ovens. Large Eloquent Dining Area for Gatherings plus Kitchen Nook/ Keeping Room Area. Private, Large Master Suite w/ Vaulted Ceilings. Access from Master Suite to the Screen Porch. Impressive Master Bath! Beautiful Cabinetry, Free-standing Tub and Huge Master Shower. Master Closet is Extraordinary! Built-ins, Custom Vanity, etc.! Beautiful Hickory REAL Hardwood Floors throughout. 2nd Story Loft Area is terrific for 2nd Family/Gathering Rm, Teen Suite, etc. complete with Wet Bar. 2nd Story Bonus Room is very spacious with access to HUGE Walk-in Unfinished Storage Area. Custom Butcher Block Tops and Cedar Shelving add so much warmth to this home. Garage is OVERSIZED, large enough for 2 full sized trucks + golf cart + riding lawn mower! Outdoor Space is ideal for Entertaining- Huge Screened Porch that leads down to Patio - great for Grilling and Entertaining. Large Front Porch. Beautifully Landscaped Yard with Irrigation System. Long Driveway. The scenery is Exquisite from every angle. The property backs up to a creek buffer and cow pasture through the woods so TOTAL privacy from your back yard! Backyard also allows for pool and/or detached garage/workshop. This house has it ALL and is a MUST SEE!

509 Cabin Creek Crk, 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
$3,080,087
5 Beds ⋅ 8 Baths ⋅ 10171415 MLS ⋅ CLOSED Status
Pre-Sale New Construction by Hurst Home Company. 6109 sqft, 5 bed, 5 full, 3 half baths. Detached garage, detached gym. Built in 2026. 3.95 acres homesite in Firefly Overlook Subdivision.

300 Firefly Overlook Rd, Pittsboro
$835,000
6 Beds ⋅ 4 Baths ⋅ 10170894 MLS ⋅ ACTIVE Status
Welcome to 20 Brushwood Court in the sought-after Chapel Ridge Community of Pittsboro! This stunning 6 bedroom 3 ½ bath 2-story home offers nearly 4,000 square feet of beautifully designed living space. This move-in ready home is situated on a spacious .53-acre lot overlooking fairway 3 of the golf course. Inside, you will find fresh interior paint throughout, soaring vaulted ceilings, spacious closet's, real hardwood floors, an open and inviting layout, and a gourmet chef's kitchen with top of the line wolf dual range and a sub zero refrigerator perfect for entertaining or everyday living. The spacious primary suite features a private sun room, a luxurious walk-in shower and an impressive walk-in closet. With five other bedrooms, you'll enjoy endless opportunities to customize the rooms to fit your needs, whether it's a home office, gym, yoga studio or bonus room the options are endless. Step outside and enjoy the peaceful golf course views from the back deck and patio area, ideal for grilling and outdoor gatherings. The welcoming front porch creates the perfect spot to relax with your morning coffee. Additional features include a security system, irrigation system, central vacuum system and a new heat pump for the main level installed in 2025 and a newer roof installed in 2019. The washer and dryer will convey with an acceptable offer. Located in the desirable Chapel Ridge golf community, this exceptional property combines luxury, comfort, and scenic living all in one. The community includes access to the clubhouse with fitness center and restaurant, pool, tennis courts, sports courts, and athletic fields. Golf memberships are available for the 18-hole championship course designed by JMP Golf Design and Fred Couples. Ideally located just minutes from downtown Pittsboro, Chapel Hill, Jordan Lake, and with convenient access to US 64 and US 15-501, this property combines scenic surroundings with everyday convenience.

20 Brushwood Ct, 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
$825,000
4 Beds ⋅ 3 Baths ⋅ 10169071 MLS ⋅ CLOSED Status
Located in the sought-after golf course community of Chapel Ridge, this custom-built home blends luxury, comfort, and everyday functionality with an ideal layout designed for both entertaining and daily living. Featuring two spacious bedrooms on the main level plus two additional bedrooms upstairs, a dedicated office, and a large recreation room with wet bar and beverage refrigerator, the home offers flexible spaces to fit a variety of lifestyles. High-end finishes throughout include custom trim work, elegant moldings, expansive windows, and beautiful built-ins that add warmth and character. Step outside to enjoy a private fenced backyard complete with a hot tub, firepit area, and an oversized screened porch with a cozy fireplace--perfect for year-round outdoor living. The upward sloping driveway leads to an oversized, attached 3-car garage, additional parking and turnaround space, while a walk-in attic provides exceptional storage. Major recent improvements include new HVAC systems, new water heater, encapsulated crawlspace, remodeled primary bathroom, upgraded electrical, and a newer roof, providing peace of mind for years to come. Residents enjoy access to resort-style community amenities including a pool with waterslide, fitness center, parks, playgrounds, sports courts, and more. Golf memberships available for additional fee. Several items convey with the home including the pool table, recreation room refrigerator, kitchen refrigerator, screened porch furniture, outdoor TV, hot tub, Ring doorbell, and some additional items--inquire within. This is a rare opportunity to enjoy upgraded living in one of the area's premier golf course communities.

1074 Golfers Vw, 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
$1,100,000
3 Beds ⋅ 4 Baths ⋅ 10168431 MLS ⋅ CLOSED Status
Custom built contemporary home, 15 minutes from downtown Chapel Hill, located on a private 4.23 acre wooded sanctuary, (two lots already subdivided, 2.162 includes house and 2.068 extra lot. Both lots included in the list price)! Walls of windows, custom wood finishes, large decks, Office and Sunroom. Chef's kitchen with 5 burner propane cooktop, large island, granite, stainless, and walk in pantry. Each of the three bedrooms have walk-in closets and en-suite baths. Unfinished roughed in lower level has 3,589 sq. ft. daylight basement with double doors to back yard and plenty of space for bonus room and 4th bedroom. 2 car attached, plus a 1,200 detached garage/workshop is a car enthusiast dream ready to reinstall car lift. Extremely well built home by much desired David Daniels with poured concrete foundation (not cinder block), French Drains, water filtration system, natural cedar exterior siding.

2390 Lamont Norwood Rd, Pittsboro
$997,000
3 Beds ⋅ 2 Baths ⋅ 10168414 MLS ⋅ ACTIVE Status
Unique, Fully Custom Fearrington Village ''Gem'' for Sale located in the charming Bradford Place neighborhood of Fearrington Village with ideal east-west exposure, lies this ideal ''Modern Farmhouse'' designed and appointed to fit the Fearrington Village ethos. Upgraded in 2022, the 3640 finished square foot home sits on a .5 acre lot with dense forest and a creek. There is a 1170 sq ft unfinished for workshop, exercise equipment, or storage. The forest can be seen upon entering and can be enjoyed by all spaces on the west side of the home including the window-walled dining room, open deck and screened porch which lend a ''Tree House'' feel to the upper living level. ''Apricot Sunsets'' can be seen through the trees. Upon entering, a foyer accesses a private main suit including a large bedroom with plenty of light from large windows that open onto the forest offering peaceful sleep, dual cedar-lined closets with built-ins, a spacious bath with windows that open onto the lush courtyard that includes a large shower, a claw foot tub and two furniture-style vanity sinks, a custom brick wall and a separate private toilet. The main wing hallway is lined with floor-to-ceiling cabinets for generous storage. From the foyer lies a large, bright and sunny flex room featuring a bay window with views of the front courtyard populated with multiple varieties of trees, flowers, and vines. Butterfly bushes grace the view to provide a ''Butterfly Ballet'' when in season. A massive Cherry tree provides shade and blooms that ''snow'' in spring. Tucked into the corner of the courtyard is a pergola which is covered with lush grape vines during spring, summer and early fall. The brick seating area provides wonderful views of all growing zones and for enjoyment of the songbirds who frequent the feeders in the gardens. The walled courtyard and gardens are truly an eco-system for small indigenous wildlife, bees and butterflies. A small raised-bed garden is included and perfect for growing herbs. The main level provides a spacious great room with vaulted ceilings and views of the forest through the window-walled dining area. Built-ins flank a custom stone fireplace which showcases an historic, 400-year-old beam mantle. An open kitchen completes the space with custom-open shelves with generous LED up and down lighting and generous storage. The kitchen features an RO water filtration system, a gas range island/breakfast bar combo, a Samsung ''Smart'' refrigerator, a new oven (2025,) and views to the deck and forest. Two more bedroom/office rooms and a full hall bath lie directly off the kitchen, one with access to the screened porch The hallway from the kitchen has 2 large pantries. A cedar-lined coat closet is near the garage entrance. A spacious, light-filled laundry room with built ins, a custom dog shower and pet feeding area completes the hallway. A pair of Maytag machines are included. One garage side door leads to a fenced, side yard/dog run which extends the length of the home. The home provides ample outdoor spaces for pets. The other garage side door gives access to the courtyard for ease with gardening projects. Another fabulous feature this home offers is the walk-out basement. The finished portion provides a versatile space that is perfect for a private office, exercise area, yoga studio, or hobby room—the possibilities are endless. Complete with a partial kitchen, it's easy to stock your favorite beverages and snacks while enjoying this flexible living space. The unfinished area offers abundant storage or can serve as an ideal workshop for projects or fresh and clean storage space with a dual HVAC systems and located within a closet in the space is the whole-house water filtration system. Low-maintenance landscaping in the courtyard is maintained by an extensive drip system. HOA manages grounds outside the courtyard.

1390 Bradford Pl, Pittsboro
$970,000
5 Beds ⋅ 4 Baths ⋅ 10168044 MLS ⋅ ACTIVE Status
**Plenty of covered storage to bring your boat, jet skis, horse trailer, RV, and more** Nestled on 7.37 breathtaking and highly usable acres, this extraordinary property offers far more than just a home. It offers a lifestyle rooted in space, freedom, connection, and versatility. Designed with multi generational living in mind, 12 Crosswinds Estates provides the perfect setting for families looking to live, gather, and grow together while still enjoying privacy and comfort. From the moment you arrive, the beauty of the property is undeniable. The expansive usable land creates endless opportunities for entertaining, hosting large gatherings, outdoor recreation, gardening, or simply enjoying the peaceful surroundings of Pittsboro living. Whether it's family cookouts, holiday celebrations, children exploring the outdoors, or evenings around a firepit under the Carolina sky, this property was built for making memories. Inside, the home is filled with stunning wood accents that bring warmth, charm, and timeless character throughout the space. The craftsmanship and natural textures create an inviting atmosphere that perfectly complements the surrounding landscape. The property also embraces a true country lifestyle with the flexibility many buyers dream of. Horses and chickens are allowed, giving you the opportunity to create your own mini farm, hobby homestead, or private retreat while still being conveniently located near Pittsboro and surrounding areas. The HOA also allows for the potential construction of an ADU, offering additional flexibility for future living space. This is a rare opportunity to own a property that combines beautiful acreage, exceptional functionality, multi generational flexibility, and a lifestyle centered around gathering, nature, and freedom.

12 Crosswinds Estates Dr, Pittsboro
$1,600,000
4 Beds ⋅ 5 Baths ⋅ 10020678 MLS ⋅ CLOSED Status
New Construction in The Hamptons, an exciting community of luxury homes on sprawling sites with convenience to UNC, Jordan Lake, Chapel Hill and Historic Pittsboro. This custom Home is complete with 3 Bedrooms on first floor along with formal dining, large open kitchen, butler's pantry and large laundry room. The screened porch overlooks a beautiful rolling open backyard which overlooks the original Ward Homeplace land which is on the National Register of Historic Homes. This home boasts additional office, gym, very large recreation room and a 4th bedroom with full bath upstairs. Don't overlook the large walk in Storage as well. This home has a dual patio and entry porch, three car garage, professionally landscaped, up lighted front elevation.

43 Laurel Knoll Dr, Pittsboro
$1,675,000
4 Beds ⋅ 7 Baths ⋅ 10119323 MLS ⋅ PENDING Status
This home offers idyllic living in the community's final phase and has room for a POOL! The main level includes a primary suite with a spa-inspired bath, zero-entry shower, and oversized walk-in closet, plus a second en-suite bedroom ideal for guests or multigenerational living. The gourmet kitchen features professional-grade Thermador appliances and a spacious walk-in scullery with sink. Upstairs offers flexible living with additional bedrooms, rec rooms, a study, and generous storage. Peaceful outdoor living with a covered porch and fireplace overlooking a wooded lot with room for a POOL! A rare opportunity to create your own private retreat. Ryan's Crossing offers an ideal blend of convenience and serenity, with proximity to Chapel Hill and Pittsboro, yet nestled within 114 acres of lush woodlands complete with trails, a open air pavilion, and more. Please note: photos are examples only, square footage is based on architectural plans, & property taxes are based on vacant lot.

405 Lila Dr, Pittsboro
$1,315,000
5 Beds ⋅ 5 Baths ⋅ 10074851 MLS ⋅ CLOSED Status
Stunning 2023 Parade of Homes Gold winner is freshly on the market...this is your chance for your dream home! A simply gorgeous custom home designed to showcase incredible views, situated on the 5th Fairway in Chapel Ridge. Enjoy privacy beyond with natural area across the course with no future homes. Also located on a short culdesac street for minimal traffic. This home has only been lived in a handful of months and is absolutely pristine. A beautiful wall of windows in both the family and downstairs primary bedroom Flood the interior with natural light. The first floor owner's suite showcases a wood vaulted ceiling, large closets and luxurious bath with vaulted ceiling and soaking tub. A stately office w/custom cabinetry greets you as you enter the home. A secondary bedroom w/ en-suite bath is also located on the main floor. The chefs luxurious kitchen has all you could want. A double oven & microwave, quartz countertops, custom tile backsplash, custom cabinetry, walk-in pantry with stained wood shelving & large Island complete this amazing kitchen. This 5 bedroom, 5 bath home with huge bonus and loft has room for entertaining everyone. The plentiful upgraded design continues with extensive custom trim details throughout. Chapel Ridge is close to everything Chatham Park has to offer, yet with a resort-style feel. Chapel Ridge is a golf course community with amazing amenities of pool, playground, sports courts, large gym and more! Don't miss out on this opportunity, These high design custom homes do not last on the market.

24 Barn Owl Ln, Pittsboro
$1,410,000
4 Beds ⋅ 5 Baths ⋅ 10026333 MLS ⋅ CLOSED Status
Embrace a life of refined luxury at this meticulously custom designed 4 bed, 4.5 bath home nestled in the serene enclave of Stonecrest Subdivision! You are welcomed to the property by a manicured front yard and the allure of jasmine blooming along the espalier trellis. The open-air front porch is adorned with copper gas-burning lanterns and grand dual front doors. Inside, the wide plank white oak floors with a matte finish guide you through sun-filled spaces, complemented by designer lighting and vaulted ceilings with rustic beams! The living room, with its custom old-world stonework wood-burning fireplace, provides a cozy retreat, perfect for entertaining. The kitchen, equipped with an Italian range, wine cooler, Bosch dishwasher, brass kitchen bridge faucet and pot filler, Kitchenaid refrigerator and handmade pendants from England, seamlessly transitions into a welcoming keeping room with a gas-burning cast iron stove from Vermont Castings. The primary bedroom suite is a sanctuary, boasting a vaulted ceiling with exposed beams, gas fireplace, and an ensuite bathroom that epitomizes spa-like indulgence with separate dual vanities, a walk-in shower, and a generously sized soaking tub. Three additional bedrooms, each with its own ensuite bathroom, ensure comfort and privacy for family and guests alike. Additionally, the upstairs is already roughed in for plumbing and electrical, providing the opportunity to add over 1,500 sqft of finished space, enhancing the home's versatility, Outside, the custom cobblestone patio overlooks a sprawling backyard bordered by scenic woods, offering a serene escape for relaxation or entertaining. With its thoughtful design, luxurious amenities, and convenient location just 15 minutes from UNC Chapel Hill and other major Triangle attractions, this home invites you to experience a lifestyle where sophisticated elegance meets everyday comfort!

551 Stonecrest Way, Pittsboro
$1,280,000
4 Beds ⋅ 5 Baths ⋅ 10125263 MLS ⋅ CLOSED Status
TAKING BACK-UP OFFERS! See Video Walkthrough! - One-of-a-kind custom estate, perfectly positioned on a private 1.65-acre homesite with an amazing resort-style yard and pool. Inside you'll find soaring 10' ceilings, wide-plank hardwoods and high-end lighting. The family room boasts coffered ceilings, a stone-surround fireplace, and abundant natural light, while the chef's kitchen impresses with floor-to-ceiling custom cabinetry, authentic marble countertops, specialty tile backsplash, and top-of-the-line appliances including a Wolf gas range. The first-floor primary suite is a true retreat, featuring a trey ceiling, private rear yard access, and a spa-inspired bath with dual vanities, freestanding soaking tub, and oversized rain shower. A flexible first-floor secondary bedroom or private home office is paired with an adjacent full bath, showcasing luxurious marble finishes and a custom tiled spa shower. The upstairs offers the additional bedrooms and spacious bonus room along with extensive walk-in attic storage spaces. Smart features such as Alta automatic window blinds, whole-house water filtration with reverse osmosis drinking system, and generator wiring add convenience and peace of mind. Step outside to experience a backyard that feels like your own private resort. A large screened porch and deck overlook a show-stopping 18'x40' PebbleTec heated pool by Michael Gress, complete with waterfalls, multi-color LED lighting, app-controlled system, copper Ionizer, and an integrated jetted hot tub framed in Tennessee Fieldstone. Entertain around the firepit patio or unwind while enjoying the professional landscaping, garden spaces, creek bed bridge, low-voltage uplighting, and irrigation system. The expansive fenced yard backs to wooded school property for privacy and tranquility. Additional highlights include a 2-car side-load garage, expanded parking, and a sealed, conditioned crawl space. From the lush professional landscaping and welcoming front porch, to the thoughtfully designed interiors, every detail of this home radiates quality. All this just 5 miles from Pittsboro's vibrant Chatham Park with shopping, dining, the YMCA, and Mosaic. This extraordinary property is more than a home - it's a lifestyle.

50 Harrison Pond Dr, Pittsboro
$1,250,000
4 Beds ⋅ 5 Baths ⋅ 10081403 MLS ⋅ CLOSED Status
Nestled in the picturesque community of Stonecrest at Norwood, this exceptional home combines beauty, space, and luxury. The primary bedroom is conveniently located on the main level, along with a versatile flex room featuring an en suite — perfect for guests or a home office. The open floor plan showcases a stylish, well-appointed kitchen with a butler's pantry and water purifier, complemented by a cozy breakfast nook and a spacious family room. A thoughtfully designed drop zone and a large laundry room are located just off the three-car garage, adding everyday convenience. Expansive windows fill the home with natural light and offer stunning views of the peaceful surroundings. The spacious primary bath features a soaking tub, separate shower, and a generous walk-in closet. Upstairs, you'll find three additional bedrooms, convenient Jack-and-Jill bathrooms, and a resourceful bonus room. Ample floored attic storage provides even more functionality. Step outside to enjoy the inviting screened porch with a fireplace, a charming deck, and a fenced-in yard. Beyond the fencing, you'll find additional green space backed by serene wooded views. Beautiful landscaping surrounds the property, enhanced by an irrigation system and landscape lighting. The whole-house generator is an added bonus. As a resident of Stonecrest at Norwood, you'll have access to fantastic amenities, including a walking trail, a pavilion with a fireplace, a kitchen, and dining space. The cozy firepit is the perfect spot to unwind at the end of the day. This home truly offers the best of comfort, style, and outdoor living — a must-see in Stonecrest at Norwood! Photos to be uploaded 3-15-25.

396 Stonecrest Way, Pittsboro
$898,000
5 Beds ⋅ 4 Baths ⋅ 10147275 MLS ⋅ CLOSED Status
Assumable Loan for 2.75%!!!! Welcome to an exceptional custom home nestled on nearly an acre in the prestigious gated community of Chapel Ridge Estates. Designed for both elegance and comfort, this residence offers soaring 10-foot ceilings, 8-foot doors, and a beautifully flowing layout that blends open-concept living with intimate, thoughtfully crafted spaces. Enjoy a chef's kitchen with an oversized island overlooking the breakfast area and expansive family room, ideal for gathering and entertaining. The main-level primary suite offers a spa-like escape with a custom jetted shower and walk-in closet. A guest suite on the first floor provides added convenience, while upstairs features two additional bedrooms and a spacious bonus room. The fifth bedroom is currently being used as an expansive media room, perfect for movie nights or game-day gatherings. From the custom wine cellar to the three-car garage and the professionally landscaped, wooded lot, every element speaks to luxury. Life in Chapel Ridge Estates means access to exclusive resort-style amenities, including a signature golf course, clubhouse, pool, fitness center, tennis, pickleball, and more. An added benefit for qualified buyers -this home offers a VA assumable loan, presenting an incredible opportunity in today's market. This is more than a home - it's a lifestyle reserved for those who appreciate the finest in design, community, and comfort.

216 Colonial Ridge Dr, Pittsboro
$730,000
4 Beds ⋅ 3 Baths ⋅ 2532014 MLS ⋅ CLOSED Status
This light filled craftsman style home provides privacy and sits back from the road with mature landscaping in the highly desired golf course neighborhood of Chapel Ridge. The primary living area is on the main level featuring an open plan with family room that has a vaulted ceiling with a fireplace and built ins leading to the kitchen with a new Jenn Air gas downdraft cooktop. Extra large screened porch with fireplace and TV overlooking the private backyard with hot tub. Separate dining room with trey ceiling and wainscoting. Also on the main level are the primary suite with vaulted ceiling, an extra large walk-in closet and spacious bath with separate shower. A much sought after guest suite which could also be used as a home office. The laundry room is conveniently situated near the kitchen. The second level features two additional bedrooms with a shared bath, loft area with office space, very large Bonus room with wet bar, pool table and access to walk in attic. Custom shades. Roof replaced 2020.

1074 Golfers View Dr, Pittsboro
$1,275,000
5 Beds ⋅ 6 Baths ⋅ 2442337 MLS ⋅ CLOSED Status
Exclusive private setting yet still on the golf course in the lovely Chapel Ridge golf community. Large lot abuts a stream buffer for added privacy. The basement has a spa area to include a dry sauna, steam room, full bath as well as an exercise room, recreation room w/ wet bar, wine room, & home theater. True luxury! 2nd floor w/ a recreation room & bedroom w/ a full bath & storage. 1st floor primary bedroom & guest suite. Brick front facade. 3 car garage. Screened porch w/ fireplace, & outdoor kitchen.

12 Brandon Pines Ct, 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
$1,780,293
4 Beds ⋅ 4 Baths ⋅ 2474247 MLS ⋅ CLOSED Status
Old world charm and stately elegance define this custom designed by homeowner, estate home. Not only does it feature modern, high-design, but it is also fully inclusive and accessible. With an elevator & generator this home is the pinnacle of thoughtful & welcoming. It is surrounded by nature, on a sweeping 2.2 acre site, in Riverstone Estates which is bordered on 2 sides by state park land. An unfinished fully accessible attic offers room to grow. Superior fit & finish!

82 Stevens Creek Dr, Pittsboro
$1,268,000
6 Beds ⋅ 5 Baths ⋅ 10159219 MLS ⋅ CLOSED Status
Welcome to a truly rare offering, a private estate set on over 11 acres, ideally located between Pittsboro and Chapel Hill, just 20 minutes to University of North Carolina at Chapel Hill. Thoughtfully renovated with designer-curated finishes, this fully permitted home blends timeless character with modern luxury while offering unmatched privacy and space. Set at the end of a long private driveway, the property offers over 11 acres of endless potential, ideal for a private retreat, outdoor entertaining, a future pool, gardening, or even space for horses. Inside, the home showcases a refined blend of warmth and sophistication with designer lighting, high-end finishes, and carefully selected materials throughout. The kitchen features Taj Mahal quartzite countertops, a stone backsplash, custom micro shaker cabinetry, real brass hardware, and premium appliances. Newly refinished pine floors on the main level, new red oak flooring upstairs, and fresh carpet create a cohesive and elevated feel. Bathrooms have been fully updated with marble tile and spa-like finishes. The layout offers exceptional flexibility, including a rare first floor guest suite. Upstairs, the primary suite features a private balcony overlooking the property. Outdoor living includes a screened-in porch and expansive deck. Other recent updates include a new roof, furnace, landscaping, and deck. Convenient to Jordan Lake, shopping, dining, and major routes to surrounding cities. Here is your opportunity to own a fully renovated estate on acreage-- where design, privacy, and possibility come together in a truly unique home unlike anything else on the market. Schedule your showing today!

419 Eagle Point Rd, 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
$1,124,000
4 Beds ⋅ 5 Baths ⋅ 10085299 MLS ⋅ CLOSED Status
Welcome to your dream home at 76 Gentry Drive, nestled in the picturesque Pennington at Jordan Lake neighborhood. This exquisite farmhouse-style sanctuary is more than just a house, it's a lifestyle waiting to be embraced. With 4 spacious bedrooms and 4.5 elegant bathrooms, this oasis spans an impressive 3,851 square feet on a sprawling 1.47-acre lot, providing plenty of space to relax and entertain. As you approach this stunning residence, the charming board and batten accents immediately draw you in, offering a warm and inviting curb appeal. Step inside to discover the invitation of real red oak select hardwood flooring that greets you and extends throughout the main living areas, paired beautifully with oversized craftsman cove crown molding. The attention to detail is evident, creating a seamless blend of luxury and comfort. The heart of the home is undoubtedly the gourmet kitchen, designed for both the culinary enthusiast and the social butterfly. Featuring a Bertazzoni Master Series 36'' Professional Range, this kitchen is ready for your finest creations. The large island with bar seating is perfect for breakfast gatherings or evening chats, while custom cabinets with glass panel accents and undermount lighting showcase both style and functionality. The subway tile backsplash adds a touch of modern elegance, making this space a joy to cook and entertain in. Flow from the kitchen into the expansive family room, where coffered ceilings and a cozy gas fireplace create an inviting atmosphere. Built-in shelving offers a perfect place for your favorite books and decorative pieces, making this the ideal spot for family movie nights or cozy evenings. Working from home? The dedicated study features a decorative accent wall and double French doors, ensuring productivity and style go hand in hand. Retreat to the first-floor main bedroom, a serene haven adorned with ceiling beams and crown molding that provide a sophisticated touch. Living at 76 Gentry Drive means embracing an exceptional lifestyle. Just a minute away from the boat ramps of Jordan Lake, your weekends will be filled with outdoor adventures, fishing, and lakeside picnics. Plus, you're only a short drive from the best shopping, restaurants, and amenities that the area has to offer. Why settle for ordinary when this extraordinary farmhouse awaits? With so many stunning features and a location that's the envy of many, 76 Gentry Drive is not just a place to live but a true sanctuary to call your own. Come and experience the lifestyle that could be yours!

76 Gentry Dr, Pittsboro
$1,381,620
4 Beds ⋅ 6 Baths ⋅ 2528853 MLS ⋅ CLOSED Status
This gorgeous home sits on the expansive conservation area in Ryan's Crossing. Enjoy private views of untouched nature along Wilkenson Creek from your covered porch. Award winning Triple A Homes designed the perfect open concept home with large kitchen, pantry, office, primary bedroom, guest suite and mudroom all on the first floor. The second floor has 3 bedrooms all with walk-in closets plus a rec. room. Ryan's Crossing is ideally located near all the conveniences of Chapel Hill and Pittsboro, but within the tranquility of 114 wooded acres with trails, yoga pavilion, & more. Note: Square footage is based on architectural drawings and final square footage may vary. Taxes are based on vacant lot.

98 Lila Dr, Pittsboro
$780,000
5 Beds ⋅ 6 Baths ⋅ 2522851 MLS ⋅ CLOSED Status
Stunning new construction on Golf Course built by Chamberlain Homes. This home features main floor master plus main floor guestroom. Beautiful gourmet kitchen with large dining area and open floorplan. Formal dining room. Upstairs - three additional bedrooms with own baths, finished bonus room. Large unfinished walk-in storage area. Private landscaped lot with irrigation. Community recreation includes pool, fitness center, sport court, tennis, volleyball and neighborhood playground.

246 Golfers Vw, Pittsboro
$1,350,000
4 Beds ⋅ 5 Baths ⋅ 10025101 MLS ⋅ CLOSED Status
If perfection were a home, this would be it, with a floor plan that was made for living and entertaining. Located in the desirable Hamptons neighborhood in Pittsboro, this house is a dream. The main floor features a first floor master suite, guest bedroom and office. The kitchen is a chef's dream with top of the line appliances and a hidden pantry. The large mud room/scullery gives you all the storage you need. The 2nd floor features an amazing bonus room with beamed ceilings, 2 additional bedrooms (one with an ensuite bath) and walk in storage that can be finished for additional heated square footage if you desire. Did we mention your own private pond? We've got that too. And you can enjoy the view on your generous covered porch with a retractable screen. Moments to Highway 64 and Fearrington Village. Convenient to 15/501, 540, downtown Pittsboro and Apex.

176 Harvest Ln, Pittsboro
$882,000
5 Beds ⋅ 5 Baths ⋅ 10025585 MLS ⋅ CLOSED Status
A wonderful combination of privacy, ideal location, and timeless style, set on 8+ acres of picturesque landscape. As you enter, you're greeted by stunning hardwood floors and intricate trim work that decorates every corner. Indulge your culinary interests in the Chef's Kitchen, equipped with stainless steel appliances, granite countertops, and elegantly crowned cabinets. The centerpiece island, illuminated by new lighting, invites gatherings, while the adjacent walk-in pantry and breakfast area offer practicality and comfort. Architectural details throughout with arched entryways leading to the grand two-story family room, where a cozy gas fireplace sets the mood for entertaining. Dual sets of French Doors welcome you into the spacious sunroom with a cozy fireplace and lots of natural light. Entertaining is a breeze in the well-appointed formal dining room, enhanced by wainscoting and complemented by a convenient dry bar. Guests will appreciate the privacy of the main floor bedroom and adjacent bathroom. Upstairs, you will find the luxurious owner's suite, boasting a generous walk-in closet and a spa-like bath featuring a soaker tub and separate walk-in shower. Three additional bedrooms, including a Jack-n-Jill bath, provide ample space for family and guests, while two flex rooms offer versatile options for work or play. Escape to the third-floor bonus room with a wet bar, bathroom, and access to the floored attic space. Unwind on the screened porch with privacy in every direction. Don't miss the the 3-car garage! Conveniently located just minutes from downtown Pittsboro, Chapel Hill, and Jordan Lake, with easy access to US-64 and US 15-501, this home offers the perfect blend of tranquility and accessibility for discerning homeowners. Move-in ready!

347 Wild Rose Ln, 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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