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473 Lila Dr, Pittsboro
$1,799,000
4 Beds ⋅ 6 Baths ⋅ 10196605 MLS
This is one of the last opportunities to call Ryan's Crossing home! Beautiful architecture, an inviting layout, and room to spread out make this a compelling opportunity in a sought Ryan's Crossing. Situated over and acre on a private cul-de-sac with a private backyard, this beautiful home has three bedrooms on the first floor and a wide-open floor plan that connects the kitchen, dining area, and family room. This home has an amazing first floor living space that provides exceptional space for entertaining or spending time with family. The large kitchen centers around an impressive, oversized island with ample room for meal prep, casual dining, and gathering PLUS a large scullery equipped with ovens, a sink, and a dishwasher providing a separate workspace for cooking and cleanup, keeping the main kitchen ready for guests. You will love the closet space and zero entry showers downstairs and upstairs has flex space (media lounge, home office, hobbies, or recreation) and an extended Jack and Jill bathroom. Unwind on the screened porch overlooking the private backyard and enjoy an oversized three car garage with plenty of room for vehicles, equipment, and storage. Located in Ryan's Crossing, one of the Triangle's premier custom home communities, residents enjoy 114 acres of preserved natural beauty with walking trails, a yoga pavilion, and open green spaces, all just minutes from Chapel Hill, Pittsboro, Jordan Lake, UNC, and major commuter routes.

473 Lila Dr, Pittsboro

58 Mint Springs Rd, Pittsboro
$1,795,000
4 Beds ⋅ 6 Baths ⋅ 10149158 MLS
Now offered at an incredible new price, this exceptional newly constructed residence, framed by more than five acres of rolling countryside, offers a rare sanctuary of space, privacy, and calm. Here, light, landscape, and thoughtful design come together in perfect harmony. Crafted by award-winning Bost Custom Homes, this four-bedroom, six-bath estate was designed to be far more than a house, it is a retreat. Every architectural line, carefully selected finish, and considered detail reflects understated luxury and intentional design, creating a home that feels both expansive and deeply personal. Sunlight pours through generous windows, illuminating refined yet welcoming living spaces designed equally for vibrant gatherings and quiet moments. The main level offers the ease of first-floor living, anchored by a serene primary suite that feels like a private haven. A secondary ensuite bedroom provides elegant accommodations for guests or extended family and lends itself beautifully to multigenerational living. At the heart of the home, the chef's kitchen showcases Wolf appliances, bespoke cabinetry, and a layout designed for gathering. Two spacious living areas provide wonderful flexibility for entertaining, while a hidden room adds an unexpected element of discovery and delight. The lower level unfolds into a world of curated leisure, with two additional bedrooms, a collector-worthy wine cellar, private fitness studio, and flexible spaces ready to become a cinema lounge, executive office, or creative retreat. A pre-planned elevator shaft provides the opportunity for future accessibility, making the home as forward-thinking as it is timeless. Outside, the landscape becomes an extension of the living space. Sweeping views unfold from the expansive porch, where mornings invite a quiet cup of tea and evenings end beneath the Carolina sky. With ample room for a future pool, the property offers the opportunity to create a truly private resort surrounded by more than five acres of peace and privacy. Yet this remarkable setting never feels removed. Downtown Pittsboro, Chatham Park, Chapel Hill, Briar Chapel, Perry Harrison Elementary, shopping, dining, and everyday conveniences are all within easy reach. A private countryside retreat without sacrificing connection, newly built, beautifully considered, and now offered at an exceptional new price.

58 Mint Springs Rd, Pittsboro

2430 Jones Ferry Rd, Pittsboro
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 10152747 MLS
Your perfect escape awaits on 3 magnificent acres, just 9 miles from Chapel Hill! Wake up each morning surrounded by nature's beauty and the peaceful sounds of the outdoors, all while enjoying effortless access to incredible dining, shopping, live music, cultural events, and university sports in Chapel Hill, Carrboro, Chatham Park, and downtown Pittsboro. No HOA, no restrictions, just the freedom to build your dream home exactly as you envision it! Make that dream a reality with Paragon Custom Homes, proudly selected as the Triangle's builder member in the exclusive Southern Living Custom Builder Network. This prestigious program brings together a select group of highly respected builders across the South, recognized for exceptional craftsmanship and thoughtful design that reflects the timeless character of Southern living. Paragon is known for incorporating Adaptive Design principles, creating homes that are elegant, intuitive, and thoughtfully designed to support the way you live today and for every season of life that follows. Two adjacent lots are also available, offering the rare opportunity to create a private family compound or secluded retreat. This is more than a homesite. It is the beginning of a home designed to serve you beautifully for a lifetime. This is Quality for Life.''

2430 Jones Ferry Rd, Pittsboro

650 Stonecrest Way, Pittsboro
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 10199904 MLS
Discover a curated expression of modern luxury and timeless Tudor architecture in this exceptional home, featuring a custom plan by renowned architect Chuck Frusterio and built by award-winning Dunning Custom Homes. Situated at the end of a cul-de-sac on a 1+ acre homesite in beautiful Stonecrest at Norwood, this property offers a peaceful setting framed by mature trees for added privacy. From the striking arched front door to the cozy library nook, every detail has been carefully selected by the owners to create a home that is both distinctive and inviting. Offering 4 bedrooms, 4 full baths, a media room, and a sunroom, this remarkable residence showcases custom, elevated finishes, and exceptional craftsmanship throughout. The chef's kitchen features inset cabinetry, a Thermador range, a Bosch dishwasher, built-in Thermador refrigerator AND freezer, an oversized cherry wood island custom crafted by Raleigh Reclaimed, and a 5-foot galley sink with dual faucets. The adjoining scullery adds a beverage refrigerator, instant-hot water faucet, and so much storage! The sizable family room flows into a serene sunroom, where a shared two-sided fireplace creates a seamless connection between the spaces. Surrounded by views of trees and nature, the sunroom offers an inviting retreat to unwind and enjoy the peaceful setting. A main-level guest suite with an adjacent full bath offers a welcoming retreat for visitors or those needing first-floor living. Upstairs, the primary suite is a private sanctuary with automated Lutron shades and a spa-inspired bath featuring custom tilework, multi-head shower system, and inset cabinetry. A secondary bedroom with upgraded carpeting and Lutron shades offers its own ensuite bath. The media room is designed for entertaining with blackout drapery, a wet bar, beverage refrigerator, and an 85-inch Samsung LED TV. Another bedroom, full bath, and conditioned storage complete the second floor. Additional designer details include Visual Comfort lighting, Coppersmith exterior fixtures, a copper entry roof, and custom window treatments throughout. Modern comforts and thoughtful technology include a custom Brinks security system with five exterior cameras, solar panels, a Tesla Powerwall, an EV charger, and a 3-car garage. This private homesite with a fenced backyard offers a peaceful setting with a nearby trailhead, community walking trails, and a beautifully appointed pavilion with a fireplace, all within convenient reach. This is a truly distinctive modern estate where architectural character, personalized design, and luxury come together beautifully. Video walkthrough: bit.ly/650Stonecrest-Video

650 Stonecrest Way, Pittsboro

297 Colonial Ridge Dr, Pittsboro
$1,650,000
5 Beds ⋅ 5 Baths ⋅ 10080780 MLS
This stunning Modern English Tudor blends timeless architectural character with sophisticated modern finishes and exceptional indoor-outdoor living in the gated section of Chapel Ridge. Soaring 10' ceilings throughout the main level create an open, airy feel, while dramatic boxed beams and a sleek 60" linear fireplace make the Great Room an impressive centerpiece of the home. Designed for effortless entertaining, the open floor plan flows seamlessly to a gorgeous covered lanai featuring an outdoor fireplace and built-in grill. At the heart of the home is a showstopping ZLINE chef's kitchen, complete with a 48" professional-style range, 54" refrigerator/freezer, oversized waterfall island, and a cleverly designed hidden pantry that provides abundant storage while maintaining the kitchen's clean, sophisticated aesthetic. The thoughtfully designed main level also includes a second bedroom and a dedicated home office, offering flexibility for guests, multigenerational living, or working from home. An unfinished basement provides exceptional potential for future living and entertaining space, a home gym, theater, wine cellar, or additional bedrooms. Built to HERO energy-efficiency standards, this exceptional home combines distinctive Modern English Tudor style, luxury finishes, energy-conscious construction, and a floor plan designed for today's lifestyle. BUILDER HAS OTHER LOTS AND PLANS.

297 Colonial Ridge Dr, Pittsboro

67 Rolling Woods Ct, Pittsboro
$1,595,000
4 Beds ⋅ 5 Baths ⋅ 10190841 MLS
Luxury awaits at 67 Rolling Woods Court! Set on a beautifully landscaped homesite in The Hamptons of Pittsboro, this highly amenitized custom home with ELEVATOR offers more than 4,000 square feet designed for comfortable everyday living and easy entertaining. Site-finished hardwoods, extensive trimwork and abundant natural light carry throughout the main level, where the spacious kitchen opens seamlessly to the dining and family rooms. A large center island, custom cabinetry and walk-in pantry make the kitchen as functional as it is inviting, while the family room's fireplace and built-ins create a natural gathering place. The main-level primary suite is a retreat of its own with a generous walk-in closet, dual vanities and zero-entry shower. A second main-level bedroom and full bath offer added flexibility for guests, an office or whatever life calls for next. An elevator with self-closing doors provides convenient access between levels, where three additional bedrooms, a dedicated home theater, flex space and multiple walk-in closets provide plenty of room to spread out. Outside, the covered veranda with phantom screen and expansive patio with linear gas fireplace overlook a beautifully maintained backyard with space to gather, entertain and unwind. Every upgrade imaginable: whole home generator, sealed crawlspace, HVAC replaced in 2024 with dehumidifier, Moen smart auto-temp in primary shower, centralized surge protector, reverse osmosis water filtration, and the list goes on. A side-load three-car garage, and abundant storage complete this thoughtfully designed home, tucked into a peaceful Pittsboro setting with convenient access to Chapel Hill and Apex.

67 Rolling Woods Ct, Pittsboro

60 Willow Creek Ct, Pittsboro
$1,595,000
4 Beds ⋅ 4 Baths ⋅ 10160197 MLS
This stunning Prewitt-Douglas Custom Homes 2026 Parade Home offers over 4,000 square feet of luxurious living space on a picturesque 1.5-acre lot in the gated community of Chapel Ridge Estates. Elegant design and extensive trim work create a distinctive backdrop for everyday living and memorable entertaining. Four spacious bedrooms and 3½ baths provide room to unwind, while the inviting hearth room offers a comfortable gathering space. A hidden pantry and scullery bring thoughtful functionality to the kitchen, keeping preparation and storage conveniently tucked away. An outdoor kitchen extends the entertaining possibilities, and a three-car garage completes this exceptional home. Experience custom craftsmanship, refined details, and generous living spaces in a beautiful Pittsboro setting.

60 Willow Creek Ct, Pittsboro

377 Lila Dr, Pittsboro
$1,575,000
4 Beds ⋅ 5 Baths ⋅ 10177168 MLS
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. This home is due to be completed in December 2026. 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

748 Valley Ln, Pittsboro
$1,500,000
10182781 MLS
25.9-acre exclusive estate homesite in an exceptional LOCATION with access through the prestigious Monterrane community. This beautiful, mostly flat and private property is ready for your custom dream home. Fully designed architectural plans are available upon request, or bring your own vision and builder. The property features a driveway, a valid 4-bedroom septic permit, access to public water and natural gas, high speed internet available and offers the rare opportunity to subdivide once into two estate lots. Wooded lot with many hardwoods. Ideally located just off Mt. Gilead Road between US-15/501 and Highway 64, you'll enjoy convenient access to downtown Pittsboro, Chatham Park, Mosaic's dining, shopping, and entertainment, as well as Jordan Lake and the Haw River for boating, hiking, and outdoor recreation. A truly one-of-a-kind opportunity to create a private luxury estate while remaining close to everything Chatham County has to offer.

748 Valley Ln, Pittsboro

2310 Jones Ferry Rd, Pittsboro
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 10152729 MLS
PROPOSED NEW CONSTRUCTION Your private sanctuary awaits! Imagine waking up every morning surrounded by towering trees and the soothing sounds of nature on your very own 3 acre retreat. This is country living at its finest, and it is closer than you think, just 9 miles from Chapel Hill with easy access to vibrant dining, shopping, cultural events, live music, and university sports in Chapel Hill, Carrboro, Chatham Park, and downtown Pittsboro. No HOA, no restrictions, just the freedom to bring your dream home to life exactly the way you envision it! Make that dream a reality with Paragon Custom Homes, proudly selected as the Triangle's builder member in the exclusive Southern Living Custom Builder Network. This prestigious program brings together a select group of highly respected builders across the South, recognized for exceptional craftsmanship and thoughtful design that reflects the timeless character of Southern living. Paragon is known for incorporating Adaptive Design principles, creating homes that are elegant, intuitive, and thoughtfully designed to support the way you live today and for every season of life that follows. Two adjacent lots are also available, offering the rare opportunity to create a private family compound or secluded retreat. This is more than a homesite. It is the beginning of a home designed to serve you beautifully for a lifetime. This is Quality for Life.''

2310 Jones Ferry Rd, Pittsboro

2354 Jones Ferry Rd, Pittsboro
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 10152743 MLS
Your private sanctuary awaits on this wooded 3-acre retreat, just 9 miles from Chapel Hill. Enjoy the peace of country living with quick access to dining, shopping, cultural events, live music, and university sports in Chapel Hill, Carrboro, Chatham Park, and downtown Pittsboro. With no HOA and no restrictions, you have the freedom to design the home and lifestyle you truly want. Make that dream a reality with Paragon Custom Homes, proudly selected as the Triangle's builder member in the exclusive Southern Living Custom Builder Network. This prestigious program brings together a select group of highly respected builders across the South, recognized for exceptional craftsmanship and thoughtful design that reflects the timeless character of Southern living. Paragon is known for incorporating Adaptive Design principles, creating homes that are elegant, intuitive, and thoughtfully designed to support the way you live today and for every season of life that follows. Two adjacent lots are also available, offering the rare opportunity to create a private family compound or secluded retreat. This is more than a homesite. It is the beginning of a home designed to serve you beautifully for a lifetime. This is Quality for Life.''

2354 Jones Ferry Rd, Pittsboro

307 August Trace Dr, Pittsboro
$1,475,000
4 Beds ⋅ 5 Baths ⋅ 10172726 MLS
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

35 Big Bear Dr, Pittsboro
$1,450,000
4 Beds ⋅ 5 Baths ⋅ 10196140 MLS ⋅ Custom Build BLDG.
PARADE HOME | 2.5 PRIVATE ACRES | 5025 SF UNDER ROOF | NEAR JORDAN LAKE & NC 540 TRIANGLE EXPRESSWAY CORRIDOR TO RTP Expansive windows fill this extraordinary estate-style residence with natural light and frame the wooded surroundings. Unparallelled craftsmanship from exquisite tile alongside cabinetry to the ceiling in the showpiece chef's kitchen to detailed artistry throughout the residence in this one-of-a-kind truly custom home. Main-level owner's retreat offers a private sanctuary with a beautifully appointed spa-inspired bath. A secluded first-floor guest suite is thoughtfully positioned. All four bedrooms feature private baths, plus a separate powder room for guests. Exceptional outdoor living includes expansive screened porches with a dramatic vaulted gathering space alongside an al fresco dining area overlooking the peaceful setting. Generous acreage provides ample space for a future pool and additional outdoor living. Set among distinguished custom residences with no HOA and minimal covenants, this exceptional property is located in the sought-after Seaforth High School district, close to Jordan Lake boat access and within easy reach of Raleigh and the RTP corridor. To be showcased in the 2026 Chatham County Parade of Homes this month, with move-in to follow. Rare opportunity to own a newly crafted luxury estate style home where privacy, acreage, architectural distinction and an exceptional location come together beautifully.

35 Big Bear Dr, Pittsboro

417 Laurel Knoll Dr, Pittsboro
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 10193509 MLS
Set on more than two private acres, this Pittsboro home feels like a retreat of its own while still being just minutes from Fearrington Village and downtown Pittsboro, and less than 20 minutes from Chapel Hill. Mature landscaping, a fully fenced backyard, and a peaceful setting create the kind of privacy that is increasingly hard to find. Step inside to a spacious foyer and dramatic two story living room, where abundant windows fill the home with natural light. The updated kitchen sits at the heart of the home, with a spacious dining room just off the kitchen offering plenty of room to gather and beautiful natural light. Thoughtfully selected designer lighting adds a custom feel throughout the home. With more than 3,700 total square feet, there is plenty of room to come together and space to spread out. The first floor primary suite offers the convenience of main level living, complete with a beautifully renovated primary bath and built in sound system. A second bedroom on the main floor is perfect for guests or can easily serve as a private home office. Upstairs, two additional bedrooms share a Jack and Jill bath, while the large bonus room offers even more flexibility for a media room, playroom, home office, or hangout space. Outside is where this home really shines. Start your morning with coffee on the screened porch, enjoy an extended pool season thanks to the heated saltwater pool, and end the day gathered around the outdoor fireplace or covered outdoor kitchen and bar. Surrounded by mature landscaping and more than two acres, the backyard feels like your own private escape with plenty of room to entertain, unwind, and simply enjoy the peace and quiet. Private without feeling remote, this is the kind of home that gives you room to breathe while keeping Fearrington Village, downtown Pittsboro, Chapel Hill, dining, shopping, and everyday conveniences within easy reach.

417 Laurel Knoll Dr, Pittsboro

755 Arrowhead Loop, Pittsboro
$1,400,000
3 Beds ⋅ 4 Baths ⋅ 1235900 MLS
Set in an established equestrian neighborhood, this thoughtfully updated 15-acre mini farm offers country living with exceptional recreational and homesteading amenities. Fresh interior paint and newly refinished hardwoods complement the open floor plan and newly built pantry area. Enjoy the backyard oasis with a pool, hot tub and gas fire pit, plus a convenient pool house with bathroom. The property also features an irrigation system, fenced pastures, stables, double-gated chicken coops and a duck house. The custom four-stall barn has been rebuilt and enhanced with two storage rooms. Electricity serves the barn, stables, coops and pool house. Additional upgrades include HVAC, a whole-house generator, water filtration, crawl-space protection, French drains, expanded propane capacity and a separate garage/storage building. With no HOA or city taxes, this property is a dream come true.

755 Arrowhead Loop, Pittsboro

755 Arrowhead Loop, Pittsboro
$1,400,000
3 Beds ⋅ 4 Baths ⋅ 10193626 MLS
Set in an established equestrian neighborhood, this thoughtfully updated 15-acre mini farm offers country living with exceptional recreational and homesteading amenities. Fresh interior paint and newly refinished hardwoods complement the open floor plan and newly built pantry area. Enjoy the backyard oasis with a pool, hot tub and gas fire pit, plus a convenient pool house with bathroom. The property also features an irrigation system, fenced pastures, stables, double-gated chicken coops and a duck house. The custom four-stall barn has been rebuilt and enhanced with two storage rooms. Electricity serves the barn, stables, coops and pool house. Additional upgrades include HVAC, a whole-house generator, water filtration, crawl-space protection, French drains, expanded propane capacity and a separate garage/storage building. With no HOA or city taxes, this property is a dream come true.

755 Arrowhead Loop, Pittsboro

14 Brushwood Ct, Pittsboro
$1,349,000
5 Beds ⋅ 5 Baths ⋅ 10198102 MLS
Situated in the established Chapel Ridge community, this to-be-built home presents a solid ownership opportunity with the space and amenities to serve a variety of needs for years to come. The sooner you go under contract on this home, the more customization options you'll have. Additional square footage above the garage can simply be unfinished storage, a future Theatre Room or your dream playroom or home office right now. SummerWind Homes will tailor it it to be exactly what you need and want it to be! This thoughtfully designed new-construc tion home will be ENERGY STAR certified, featuring spray-foam insulation, and a sealed crawlspace. These upgrades work together to deliver exceptional energy performance, consistant indoor comfort in every season, imporooved air quality and lower utility costs while helping protect the structure against moisture and enhancing long-term durability.

14 Brushwood Ct, Pittsboro

3477 Castle Rock Farm Rd, Pittsboro
$1,300,000
4 Beds ⋅ 2 Baths ⋅ 10198647 MLS
RARE FIND! A peaceful retreat in Chatham County! This beautiful 42+ acre property offers the perfect combination of privacy, convenience, and endless possibilities, located just 25 minutes from Chapel Hill, 20 minutes from downtown Pittsboro and Chatham Park, and 5 minutes from Chapel Ridge Golf Course. This updated 4-bedroom home is move-in ready and offers beautiful views from nearly every window. The main level features two guest bedrooms, an inviting living room with a woodburning fireplace and soaring ceilings overlooking the deck and private, tree-lined backyard, formal dining area, and an updated kitchen with new appliances. Upstairs you'll find the spacious primary bedroom with a sitting area, large walk in closet and a "secret" room, an additional guest bedroom, and office space overlooking the serene front yard. Recent updates include fresh interior paint, new downstairs HVAC, updated bathrooms. There is abundant storage and a water treatment system. Outside, the property offers fenced pastures, mature hardwood trees, open acreage, road frontage, and multiple existing structures. The possibilities are truly exceptional. The property could lend itself to a multigenerational setup, private family compound, equestrian or agricultural use, guest accommodations, "barndominium" event or retreat space, short-term rental opportunities, or simply a peaceful private homestead. The existing accessory dwelling offers additional potential and includes its own well and septic (this second septic needs repair), washer/dryer hookups, and a charming claw foot tub. The pole barn provides additional storage and could potentially be converted into a large garage, workshop, equipment storage, or collector's space. Enjoy the main home today while taking your time to envision the future of this remarkable property. Whether you're looking for room to spread out, space for animals, additional living options, or a property with long-term potential, this is a rare opportunity to own 42+ acres in a beautiful and convenient Chatham County setting. A property with this much land, privacy, infrastructure, and versatility doesn't come along often! Don't let this little slice of paradise slip away schedule your private tour today! There is no for sale sign look for the red mailbox.

3477 Castle Rock Farm Rd, Pittsboro

147 Colonial Trail Ct, Pittsboro
$1,300,000
4 Beds ⋅ 5 Baths ⋅ 10186847 MLS ⋅ Icg Homes Llc BLDG.
GOLF COURSE VIEW - Welcome to 147 Colonial Trail Court in Pittsboro! This beautiful home offers plenty of space and an easy, comfortable layout with 4 bedrooms, 4 full bathrooms, and 1 half bath, plus a 3-car garage. The spacious layout provides plenty of room for entertaining, relaxing, and enjoying time with family and friends. A standout feature is the screened porch with a cozy fireplace—the perfect year-round retreat for morning coffee, evening gatherings, or relaxing after a long day. Inside, you'll find a dedicated study, ideal for working from home or creating a quiet office space, along with a spacious recreation room that offers endless possibilities for a media room, game room, or additional gathering space. The 3-car garage provides ample room for vehicles, storage, and all the extras that come with an active lifestyle. Located in a desirable Pittsboro community with outstanding amenities, residents can enjoy golf, a community pool, playground, and sport court, creating a true resort-style living experience right at home. With its thoughtful floor plan, exceptional outdoor living space, impressive amenities, and prime Pittsboro location, 147 Colonial Trail Court is a home you won't want to miss.

147 Colonial Trail Ct, Pittsboro

72 Hillsboro St, Pittsboro
$1,300,000
10160140 MLS
Exceptional commercial opportunity in the heart of Downtown Pittsboro! This two-level brick office building offers outstanding visibility with direct line-of-sight exposure along Hillsboro Street, positioned in one of the area's most rapidly growing corridors. This layout supports a variety of office configurations, including shared workspace concepts with common bathrooms and breakroom potential - ideal for multiple tenants or a collaborative business environment. The property includes an adjoining parking lot, providing convenient on-site parking in addition to nearby public options. A recorded survey is available and established easements ensure excellent access and functionality. Strong rental potential makes this an attractive option for investors or owner-occupants seeking long-term growth in a thriving market. Please note; the property is not currently suited for restaurant use. Surrounded by ongoing Chatham Park, Disney/Asteria, rapidly growing Pittsboro development and increasing foot traffic, this location presents potential to any anyone looking to establish a presence in one of the region's most dynamic downtown corridors.

72 Hillsboro St, Pittsboro

45 Quail Pt, Pittsboro
$1,299,950
4 Beds ⋅ 5 Baths ⋅ 10160405 MLS
Grading is complete and permits are in place now is your chance to have your dream home overlooking Hole #2 of the highly sought-after Fred Couples Signature 18-hole golf course in the next 12 months. This thoughtfully designed 4,323 sqft home features an open and airy layout with 10 ft and 19 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 4.5 bathrooms, all secondary bedrooms are en-suite for ultimate comfort and privacy. 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 beautiful golf course views. Additional features include hardwood flooring throughout the main living areas, carpet in the bedrooms, and a tankless water heater for efficiency. A dedicated gym or media room and a spacious loft overlooking the main level provide flexible living and entertainment spaces. Situated on a private homesite, the property also includes a 3-car garage. 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.

45 Quail Pt, Pittsboro

114 Autumn Gate St, Pittsboro
$1,275,000
5 Beds ⋅ 6 Baths ⋅ 10192871 MLS
Impressive Modern Contemporary 3 Car Garage on 1/2 Cul De Sac Backing to Permanent Wooded Open Space w/Incredibly Huge Master Suite!!! Cozy Flagstone Floor Front Porch w/Double Door Entry to Nicely Wall Accented Large Foyer!! Large 12x14.75 Guest Bedroom w/Private Full Bath!! Generous Trayed 20x20 Family Rm w/FP Accented w/Cabinets & Shelves & 4 Panel Glass Slider Overlooking 15.75x14 Vaulted Screen Porch w/OMG Wooded View!! Gourmet Kitchen w/Cabinets to the Ceiling, Stainless Steel Appliances, Vented Gas Cook Top & HUGE 5'x10.5' Island!!! Large 14x14 Dining Rm w/Great View Too & Overlooking Vaulted Screen Porch!! Wow 15.25x18 Primary w/Incredible Wooded View Via Picture Window & Incredible 13x14 Primary Bath w/Separate Tub & Zero Entry Shower & Large Picture Window for Natural Lighting & Huge 13x14 WIC w/Extensive Shelving & Quartz Top Island & Transoms for Natural Lighting Connected to Laundry w/Generous Cabinetry & Sink Connected to Mudroom w/Bench & Cubbies!! Nice Wide Staircase to 2nd Floor w/Large Landing Area!! Generous 15.75x20.75 Bonus/Media Rm w/Great View Accented with a 11x13.25 Office Space w/Direct Access to 11x13 Finished Flex/Storage Rm!! 15x13 Bdrm 3 w/Direct Access to 12x15 Finished Flex/Storage Area Ideal for Guests w/Children because it could be a Bedroom Off a Bedroom & Direct Full Bath Access!!! Fantastic Hall Area Storage!! On the Front Side of the House it has 2 Nearly Identical 12x14.75 & 12x13.75 Bedrooms w/Private Baths/ WIC's w/Benches!! Generous Backyard w/Incredible Permanent Wooded Views!! Large 3 Garage w/Insulated Panel Garage Doors, EV Charging Source, & Tankless Gas Water Heater!! Spay Foam Insulation!! Sealed Crawl Space!! EcoSelect Plus Certified!!! Very Nicely Landscaped on One of The Quietest Streets in Chatham Park!! Park w/Splash Pad, Play Ground, Dog Park, & Covered Dining Area!! Brand New YMCA Built in 2025 w/2 Exterior Pools! 4 Soccer Fields Coming too!! Sidewalks on Both Sides of the Streets!! Major Medical Campus being Build!! Trails Galore through community w/Access from Autumn Gate Street!! Retail right around the corner at the Mosaic!! The #1 Visited State Park Lake Jordan Minute Away!!

114 Autumn Gate St, Pittsboro

116 Emelia Ln, Pittsboro
$1,245,000
4 Beds ⋅ 4 Baths ⋅ 10188780 MLS
Welcome home to this custom-built residence by award-winning ICG Homes. Meticulously designed and maintained, this home features numerous high-end upgrades completed both during and after construction, creating a truly serene and luxurious feel from the moment you walk through the door. Detailed information is available outlining the property's extensive upgrades, including a whole-home generator, custom blinds, remote-controlled shades, and numerous audio, and technology enhancements. With a thoughtful layout ideal for entertaining and multigenerational living, the home includes two en-suite bedrooms on the main floor, including a spa-like primary suite retreat. In the living room, a 12-foot stacking door opens completely to a vaulted, light-filled screened porch, creating a seamless indoor-outdoor living experience. The upgraded chef's kitchen features custom-designed cabinetry and provides a warm, welcoming space for friends and family to gather. Several additional flex spaces allow the home to adapt to your specific needs. The upstairs flex room includes a closet and can serve as an optional fifth bedroom, office, or media room. A separate bonus room and dedicated workout room provide even more flexibility. This beautiful home is located in Ryan's Crossing, Pittsboro's premier conservation neighborhood. This exceptional community is centered around 47 acres of conserved open space, providing a lush, green environment and generously sized lots. Residents enjoy direct access to the Briar Chapel trail system for miles of hiking and biking, as well as a private half-mile walking trail with a yoga pavilion. With the final homes in Ryan's Crossing priced from $1.4M to $2M, this property offers exceptional value along with an extensive collection of upgrades. The location is also highly convenient, just minutes from Chapel Hill, Pittsboro, and Jordan Lake. A 3D tour is available. Welcome home!

116 Emelia Ln, Pittsboro

36 Rosefield Ct, Pittsboro
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 10161024 MLS
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

431 Fieldstone Ln, Pittsboro
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 10079735 MLS
Build your new custom home in the established and sought after neighborhood of Fieldstone located minutes from Chapel Hill/Carrboro and Pittsboro. Build this plan, one of the builder's other plans or bring your own! This floorplan features the primary suite on the main level along with his and hers closets, family room with gas fireplace and access to the screened porch, study with access to the large front porch, eat in kitchen with pantry, sunroom, mud room and laundry. Upstairs are three additional bedrooms each with access to a full bath. The sizeable loft is perfect for a bonus room. With a flexible floorplan many options exist. The study on the main floor adjoining the half bath could be converted to a second bedroom with a fullbath. The sunroom could be used as a breakfast room or office. The unfinished attic could be partially or fully finished for more living area - second bonus room, gym, office space, etc. Possibilities are endless!

431 Fieldstone 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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