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

1624 Cedar Grove Rd, Pittsboro
$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
$1,199,000
3 Beds ⋅ 4 Baths ⋅ 10180831 MLS ⋅ ACTIVE Status
Nestled on a private, wooded 1.63-acre homesite just 3 miles from charming downtown Pittsboro, this stunning new construction home offers the perfect blend of tranquility and convenience. Designed for effortless living, this thoughtfully crafted single-level home features 3 bedrooms, 3.5 baths, and an open-concept floor plan with exceptional craftsmanship throughout. The gourmet kitchen boasts a large center island, walk-in pantry, and wet bar, flowing seamlessly into the spacious great room with soaring 12-foot ceilings and decorative beams. Retreat to the luxurious owner's suite featuring a vaulted ceiling, spa-inspired bath, and oversized walk-in closet. Each secondary bedroom includes its own en-suite bath, offering comfort and privacy for family or guests. Enjoy year-round outdoor living on the expansive covered rear porch overlooking the peaceful wooded setting. With a formal dining room, oversized laundry room, abundant storage, and a spacious 3-car garage, this home combines timeless design with modern convenience in one of Pittsboro's most desirable locations.

71 Caz Trce, Pittsboro
$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
$699,500
5 Beds ⋅ 4 Baths ⋅ 10179756 MLS ⋅ ACTIVE Status
Stunning 5-bedroom, 4-bath home with a first-floor guest suite is now available! This showstopper features a formal dining room or flex space, private pocket office, and spacious drop zone. The gourmet kitchen is the heart of the home with premium appliances, a butler's pantry, and an open layout overlooking the breakfast area and inviting living room. Step outside to enjoy the screened porch, deck, and fenced backyard with peaceful wooded views. Upstairs, you'll find a versatile loft, four additional bedrooms, and an exceptional primary suite with its own private sitting room or den. Packed with flexible living space, designer finishes, and incredible value, this home truly has it all. Located in sought-after Chatham Park, residents enjoy Mosaic's shopping and dining, outstanding amenities, parks, and miles of scenic greenway trails—all approximately 30 minutes from RTP, 15 minutes from Jordan Lake, and just minutes from major highways.

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

51 Millennium Dr, Pittsboro
$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
$1,140,000
4 Beds ⋅ 4 Baths ⋅ 10178037 MLS ⋅ ACTIVE Status
PARADE HOME | Move-In Ready Mid-October | Chatham County Privately nestled on 1.5 wooded acres just minutes from Chapel Hill, this exceptional custom-built home to be featured in the Chatham County Parade of Homes offers the perfect balance of timeless architecture, modern luxury, and peaceful privacy. A striking exterior showcases expansive outdoor living spaces highlighted by a stunning stacked-stone fireplace, creating an inviting setting for year-round entertaining or quiet evenings surrounded by nature. Inside, soaring 10-foot ceilings and a dramatic two-story foyer introduce a home designed with elegance, comfort, and everyday livability. The thoughtfully crafted floor plan features four spacious bedrooms and four beautifully appointed baths, including a luxurious main-level owner's retreat and a private first-floor guest suite. The heart of the home is an impressive chef's kitchen featuring a 36-inch five-burner cooktop, oversized island designed for gathering and entertaining, and expansive walk-in pantry with wood shelving that combines exceptional storage with everyday convenience. Upstairs, flexible living spaces include a spacious media room, open loft, and charming princess suite with private bath. A hidden secret room adds a fascinating touch, offering endless possibilities as a media lounge, home gym, creative studio, wine room, playroom, hobby space, or storage. Thoughtfully designed with exceptional craftsmanship and luxurious finishes throughout, this remarkable new construction delivers the rare combination of privacy, sophistication, and convenience in one of the Triangle's most desirable locations. Current photos include construction progress along with examples of the builder's exceptional craftsmanship from previously completed homes. Move-in ready by mid-October.

4025 Hamlets Chapel Rd, Pittsboro
$1,170,000
3 Beds ⋅ 4 Baths ⋅ 10177716 MLS ⋅ ACTIVE Status
Amazing opportunity to own a practically brand-new, barely lived in custom home set on a private 3-acre homesite with no HOA. This stunning home offers the perfect blend of peaceful country living and everyday convenience. Located just under 2 miles from charming downtown Pittsboro, with easy access to Highway 64. Nestled in a serene natural setting with Roberson Creek running alongside the property, this home provides a rare combination of privacy, space, and accessibility. Designed with both comfort and functionality in mind, this home showcases a bright and airy open floor plan ideal for modern living and entertaining. The main living areas are highlighted by impressive 22' vaulted ceilings and expansive sightlines that seamlessly connect the gourmet kitchen, large dining area, and living space. A stunning quad sliding glass door opens to a spacious screened-in porch, perfect for indoor-outdoor living as both areas boast gas fireplaces. The Master Bedroom and Bath also highlight 22' Cathedral Ceilings. The custom gourmet kitchen features high-end finishes, modern smart appliances, and ample space for cooking, gathering, and entertaining. A dedicated home office provides a quiet and flexible workspace, making the home well-suited for today's lifestyle. Outside, enjoy the tranquility of your own private retreat, enjoying the open acreage, or taking advantage of the generous space to bring your boat, RV, or future outdoor additions. Additional premium upgrades include Quartz Tops, Hardwood Floors, Rainbird Irrigation System, Whole-house Water Filtration and Dehumidification Systems, Smart Whole House Water Monitoring System, Epoxy Flooring in the 3-car garage, and much more. The home is thoughtfully appointed throughout and can be sold nearly fully furnished for a truly turnkey opportunity. Chiminea and fountains convey. Please see documents for a full list of upgrades and available furnishings.

160 Roberson Creek Rd, Pittsboro
$570,000
3 Beds ⋅ 4 Baths ⋅ 10176384 MLS ⋅ ACTIVE Status
Welcome to exceptional living in sought-after Potterstone Village, where comfort, style, and convenience come together just minutes from vibrant downtown Pittsboro and the exciting growth of Chatham Park. This beautiful home offers the ease of main-level living paired with versatile spaces for entertaining, working, and relaxing. Hardwood floors, elegant architectural details, and abundant natural light create a warm and inviting atmosphere throughout. The open kitchen features granite countertops, a tile backsplash, stainless steel appliances, and seamless access to the butler's pantry and dining room featuring decorative wainscoting, crown molding and coffered ceiling. You're sure to enjoy the enclosed sun porch, multi-level deck, and private fenced backyard—perfect for gatherings or peaceful evenings outdoors. The first-floor master suite serves as a private retreat with a tray ceiling, spa-like bath, and spacious walk-in closet. Upstairs, you'll find two additional bedrooms, a generous loft area, a large bonus room ideal for home entertainment or recreation space, and extensive walk-in attic storage. Complete with a covered front porch, two-car garage, and access to neighborhood amenities including a clubhouse, pool, pond and hiking trails this move-in-ready home offers the perfect blend of refined living, everyday comfort, and investment in one of Pittsboro's most desirable communities. Easy commuting to Pittsboro's surrounding areas including Sanford, Chapel Hill, Raleigh & Chatham Co.

136 Windsong 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
$726,000
5 Beds ⋅ 4 Baths ⋅ 10173122 MLS ⋅ ACTIVE Status ⋅ Ashton Woods BLDG.
Stunning 5-bedroom, 3-car garage home in a gated community in Pittsboro. This like -new home offers an open-concept layout with soaring 10' ceiling and highly upgraded kitchen with huge center island perfect for entertaining and everyday living, the kitchen flows seamlessly into the spacious family room, creating a bright and inviting gathering space. A main level guest room add flexibility. Enjoy peaceful wooded view from the 3-season room on cul-de-sac lot. Upstairs offers a generous loft and a luxurious owner's suite with dual walking closets. Thoughtfully upgraded and beautiful maintained-Move-In-Ready

18 Cloudview Ct, Pittsboro
$775,000
4 Beds ⋅ 4 Baths ⋅ 10172128 MLS ⋅ ACTIVE Status
Discover this four-bedroom, three-and-a-half-bathroom single-family residence situated in Pittsboro, NC, offering substantial space for comfortable living. Set on an expansive 437,646 square-foot lot, this property provides exceptional privacy and land for those seeking room to spread out beyond the typical residential setting. The home's thoughtful layout includes multiple bedrooms and bathrooms, accommodating various living arrangements and guest accommodations. Located outside a subdivision, this residence offers the independence of a standalone property while maintaining convenient access to the Pittsboro area. This is an excellent opportunity to own a generously-proportioned home on considerable acreage.

743 Bowman Bare Rd, 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
$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
$659,900
4 Beds ⋅ 4 Baths ⋅ 10169552 MLS ⋅ ACTIVE Status ⋅ Pickney BLDG.
Final opportunity in NoVi Chatham Park to own a home with a finished bonus room and full bath above the detached garage. With more than 3,000 square feet, this thoughtfully designed home features 4 bedrooms and 4 full baths, including a first floor guest bedroom with full bath nearby. The flexible layout offers incredible versatility for multigenerational living, long term guests, a private office, media room, fitness space, or separate retreat area. The open concept main living area is filled with natural light and designed for both entertaining and everyday living. Upstairs, a spacious loft provides an additional gathering space, while the oversized Owner's Retreat features a spa inspired bath and massive walk in closet. Located just across from the YMCA and future park, this home offers one of the most unique and versatile layouts remaining in North Village at Chatham Park

416 N Village Pkwy, 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
$850,000
3 Beds ⋅ 4 Baths ⋅ 10153145 MLS ⋅ ACTIVE Status
Located in a highly desirable North Chatham neighborhood, this beautiful home sits on 2 private acres and features a flexible main-floor living design with three bedrooms on the primary level. Inside, the home offers high ceilings, wonderful natural light, and an easy-flow floor plan designed for comfortable everyday living and entertaining. The gourmet kitchen with wormy maple countertop opens to the main living spaces and connects seamlessly to the outdoor areas. Enjoy quiet mornings or evening gatherings on the screened porch that opens to a spacious deck overlooking the property. An unfinished 2nd floor and daylight basement provides exceptional opportunity for future expansion, allowing the next owner to easily add significant square footage if desired.

464 Deer Mountain Rd, Pittsboro
$1,120,000
4 Beds ⋅ 4 Baths ⋅ 10042208 MLS ⋅ ACTIVE Status
Move In Ready Bristol Plan! Don't miss the opportunity to make The Bristol English Cottage your dream home. This home is located in Corbett Landing, a new custom neighborhood located inside the town-limits of Pittsboro, North Carolina. Nestled on this wooded lot, this enchanting English Cottage-style home combines timeless charm with modern amenities. Step into a welcoming foyer that leads to a formal dining room. Adjacent to the dining room is a convenient butler's pantry. The heart of the home boasts a well-appointed kitchen with ample counter space and storage. Upstairs, you will find a luxurious primary bedroom complete with an en-suite bathroom and spacious walk-in closet. Two more generously sized bedrooms and a versatile rec room provides options for entertaining. On the third floor you will find an additional flex room with full bath and walk in attic storage. $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.

162 Gaines Trl, Pittsboro
$965,000
4 Beds ⋅ 4 Baths ⋅ 10084591 MLS ⋅ ACTIVE Status
Beautiful custom home in the highly desirable Chapel Ridge neighborhood. The primary suite and guest bedroom are on the first floor with two additional bedrooms upstairs. This wonderful open floor plan gives you plenty of room to entertain. Walking distance to the many community amenities including the pool, golf and tennis.

829 Chapel Ridge Dr, Pittsboro
$799,900
4 Beds ⋅ 4 Baths ⋅ 10163391 MLS ⋅ ACTIVE Status
Every day is a vacation at this marvelous 4 bedroom 3 1/2 bath Chatham County home! Let's start with the outside: A 24' diameter pool, hot and cold water shower with changing room plus a water slide with custom surround decking and clubhouse anchors the backyard, a wooded setting perfect for big gatherings or just relaxing with the family. There's also a deck and patio near the grill, and all the top boards on the decks are composite for low maintenance. There's a trail with a bridge around the over 2 acre lot for walking or riding the mountain bikes. There's plenty of room to park other toys too - RV, Boat, Trailers, you name it! Plus 2 electric wired storage buildings with security for your tools, hobbies or crafts. Heading inside, first is the big front porch perfect for a swing and rocking chairs. The Living Room features a gas log fireplace and in-wall surround speakers. And for a quiet afternoon read, the sitting room is ideal. A formal Dining Room fronts the renovated kitchen with new dishwasher and cooktop, and be sure to peer into the custom pantry! A breakfast nook and counter are great for informal meals or take it out to the sunroom for dining with a killer view. A large laundry room is off the hallway to the Primary Bedroom- and what a room it is - high ceilings, gas log fireplace, custom closets and an amazing view of the tree tops. Then there's the spa-like bathroom featuring two sinks, heated towel bar and a huge walk-in tiled shower with yet another breathaking view! Another spot for year round vacations! Upstairs are 3 bedrooms and 2 bathrooms, one en-suite. Perfect for the kids, guests and/or home office(s). The ground floor, accessed from stairs off the Laundry Room hall or 2 exterior doors, houses a 28 x 30 Entertainment Room with pool table, fridge, bar, A/V shelf, TV mount and surround sound. It could easily be converted to a one or two car garage as this was the original design. Also at this level is a one car garage with tons of customized storage shelving, plus an Exercise Room and a workshop with a huge safe for all your valuables!. All of this just 1/2 mile from the Haw River and Bynum, 10 minutes to Pittsboro, 25 minutes to Chapel Hill and 40 minutes to the RDU Airport! Come visit this one to see your everyday vacation getaway!

89 Lauren Ct, Pittsboro
$975,000
5 Beds ⋅ 4 Baths ⋅ 10156639 MLS ⋅ ACTIVE Status
Rare value in Chapel Ridge: 5 bedrooms, 4 baths, and 4,249 square feet on a private 1.78-acre homesite. This house is priced well below the neighborhood average per square foot. The lot slopes back from the road into a canopy of mature hardwoods, providing secluded, natural shade that lowers summer cooling costs. The grounds are professionally maintained, and the home itself is barely lived-in and shows like new. A whole-house generator provides peace of mind through any weather. Inside, find an open floorplan with coffered ceilings, a chef's kitchen, and a first-floor primary suite. Enjoy Chapel Ridge's gated section along with community pool, tennis, fitness center, and clubhouse access. Located within minutes of historic downtown Pittsboro, UNC-Chapel Hill, and UNC Hospitals. Please remove shoes. The back lot extends all the way to the back road. This home is still under structural warranty.

378 Crimson Way, Pittsboro
$739,900
3 Beds ⋅ 4 Baths ⋅ 10164090 MLS ⋅ ACTIVE Status
Updated rustic style home in popular Redbud neighborhood in Pittsboro on wooded 3.5 acres with privacy and 700 sq ft of decking including wrap-around decking on 3 sides. Open floorplan with new floors, new kitchen cabinets, stainless steel appliances, pantry, and updated baths. Main floor primary bedroom suite. Main living areas with wood ceiling, lots of windows, and a fireplace. Enjoy the window-filled loft area, and the lower level has 2 bedrooms and additional flex room, along with full bathroom and laundry area. No carpet in this home! Fenced area in backyard accessible from deck and basement. Garage storage has low ceiling height. Neighborhood has contracted with Spectrum for fiber internet and TV at bundled rate of $87 per month - great option for Buyer. Enjoy this wooded oasis while being close to Jordan Lake, Chatham Park, and downtown Pittsboro. Approximately 25 min to shopping in Apex

224 Buteo Rdg, Pittsboro
$925,000
5 Beds ⋅ 4 Baths ⋅ 10157457 MLS ⋅ ACTIVE Status
Welcome to this beautifully designed 5-bedroom, 4-bath residence offering a thoughtfully planned layout and scenic surroundings. From the expansive front porch, enjoy views overlooking the nearby golf course, creating a tranquil and open setting. Inside, the light-filled home features a two story family room, spacious main-level primary bedroom, and secondary bedroom and bath, all providing convenience and flexibility. The additional bedrooms and baths offer ample space for a variety of living arrangements, work-from-home needs, or guest accommodations. A sealed crawlspace allows for both peace of mind and extra storage, in addition to the unfinished storage area located inside the home. Situated within a golf course community, residents have access to a range of amenities, which include a pool with waterslide, pickleball courts, additional sports courts, playground, and fitness center. This property presents an opportunity to enjoy comfortable living in a community-oriented environment with recreational options nearby.

36 Nuthatch Dr, Pittsboro
$1,190,000
4 Beds ⋅ 4 Baths ⋅ 10140820 MLS ⋅ ACTIVE Status
This extremely rare 1.45 acre lot is located only 1.5 miles from downtown Pittsboro and the circle....yet it feels as if you are located in a country getaway. It's so easy to zip in and out to town from here, or to access the Triangle from 64 to 540 or Moncure-Pittsboro Rd to Rt 1. This beautiful flat parcel has mature beech and oak trees with dense foliage in Spring-Autumn, and plenty of privacy. Very minimal restrictions- chickens are allowed and NO architectural review or HOA for outbuildings, modifications, or landscaping. The floorplan is open and focused on main floor living. It has vaulted ceilings, large screened-in porch with fireplace, and bbq deck. Tons of space outdoors for pool, patio, outdoor kitchen, firepit area, etc. Home has an eat- in kitchen, a huge island, and scullery/pantry. The master and two secondary bedrooms are on the main floor. ...one can easily be converted to an office. Her and his master closets have the laundry room connected. The 4th bedroom, bath and bonus room are on the second floor. There is plenty of storage and a three car garage. Auxiliary dwellings and outbuildings are allowed. Triple A is a consistent gold medal and custom builder, currently building in several $2-3+M communities in the area. This opportunity for new construction and main level living on a 1.45 acre parcel this close to town is extremely unique and rare. The completed photos are of the same floorplan built nearby. There is still time to make minor changes to this plan and choose custom finishes. This home has already started construction.

638 Old Goldston Rd, Pittsboro
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 10068143 MLS ⋅ ACTIVE Status
J3S Plan with Golf Course Views - Drywall is completed on this large private wooded homesite with golf course views. Estimated completion by June 2026. This open design features 4 bedrooms and 3.5 baths, including a first-floor owner's suite. The spacious family room showcases a soaring 19-ft ceiling, 48'' gas fireplace, and sliding patio doors that bring in abundant natural light. Enjoy a custom designed kitchen with cabinetry boxed to 10-ft ceilings, Bosch stainless steel appliances, and a 36'' gas range, all open to the main living area. The home also includes a separate dining area, a second-floor loft, and a large screened deck with additional secondary deck. Additional features include a tankless water heater and a 2-car garage. Located in Chapel Ridge, offering resort-style amenities: clubhouse, pool, fitness center, pickleball, tennis, volleyball, basketball, and a soccer field. Residents also enjoy access to the Fred Couples-designed 18-hole championship golf course, ranked among the finest in the country.

9 High Ridge Ln, Pittsboro
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 10151616 MLS ⋅ ACTIVE Status
Welcome to this stunning custom home in the prestigious Chapel Ridge community. Designed with entertaining in mind, the open floor plan delivers generous living spaces and effortless flow from room to room. The main level offers the convenience of a private primary suite and a secondary bedroom, while two additional bedrooms are tucked upstairs for added privacy. Step outside and enjoy resort-style amenities just moments from your door -- including a pool, golf course, and tennis courts. Thoughtfully designed, impeccably finished, and perfectly located -- this is Chapel Ridge living at its finest.

490 Chapel Ridge Dr, Pittsboro
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 10161024 MLS ⋅ ACTIVE Status
A rare opportunity awaits in the exclusive Estates at Chapel Ridge. This distinguished Prewitt-Douglas custom home sits on nearly an acre -- one of the last remaining lots in this coveted enclave. Spanning over 3,500 square feet, the residence showcases high-end finishes throughout and a desirable main-level primary suite complete with dual walk-in closets. Four bedrooms and 3.5 baths offer ample space for comfortable everyday living and effortless entertaining. Residents enjoy access to Chapel Ridge's full suite of community amenities, providing year-round recreation for the entire family. Exceptional craftsmanship, a premier lot, and an unmatched location -- opportunities like this are few and far between.

36 Rosefield Ct, Pittsboro
$1,160,000
4 Beds ⋅ 4 Baths ⋅ 10160679 MLS ⋅ ACTIVE Status
Discover this beautifully crafted luxury custom home, built by an award-winning builder. Offering a thoughtfully designed layout and quality finishes throughout. The main level features a spacious primary bedroom suite along with an additional bedroom and full bath, providing flexible living arrangements. A dedicated study offers a private workspace or quiet retreat. The open living areas connect seamlessly to an outdoor deck and screened-in porch, creating inviting spaces for everyday living and entertaining. Upstairs, you'll find two additional bedrooms, each with access to a full bath, along with a large recreation room and separate media room. A substantial walk-in storage area provides ample space for organization. Located within a golf community, residents have access plentiful amenities to include a pool with water slide, fitness center, clubhouse, sports courts, and playground. For association documents please visit https://www.casnc.com/communities/chapel-ridge-community/

154 Colonial Trail Ct, Pittsboro

Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .