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132 Penny Ln, Pittsboro
$260,000
3 Beds ⋅ 1 Baths ⋅ LP771437 MLS ⋅ ACTIVE Status
Discover the charm of country living with the convenience of a desirable Chatham County location! Situated on approximately 0.96 acres, this single-story home offers three bedrooms, one full bathroom, and approximately 800 square feet of living space.Newer HVAC, new well and well pump. The property provides an opportunity to enjoy a peaceful rural setting with room for outdoor activities, gardening, or creating your own backyard retreat. Whether you’re looking for a primary residence, investment property, or a home to make your own, this property offers possibilities in an attractive location.Location is a standout feature! Conveniently situated between Pittsboro and Chapel Hill, the property offers access to the shopping, dining, and amenities of both communities. Enjoy proximity to Jordan Lake, Fearrington Village, and the University of North Carolina at Chapel Hill, while appreciating the quieter atmosphere of Chatham County.With nearly an acre of land and a location convenient to some of the area’s most desirable destinations, 132 Penny Lane presents an opportunity to enjoy country living without sacrificing accessibility.

132 Penny Ln, Pittsboro

1390 Bradford Pl, Pittsboro
$785,000
3 Beds ⋅ 2 Baths ⋅ 10199970 MLS ⋅ ACTIVE Status
Located on a quiet street in the charming Bradford Place neighborhood of Fearrington Village, with ideal east-west exposure, lies this ideal, warm, and charming cottage-style modern farmhouse designed and appointed to fit the Fearrington Village ethos. The home was fully upgraded in 2022. The main level consists of approximately 2533 square feet. Additionally, approximately 1234 square feet of living area are found on the lower level of the home, this area is accessed by a path that leads to the back patio. The home sits on a .5-acre lot with dense forest and a creek. The home's main entrance overlooks a generously irrigated, a very private and lush courtyard populated with dozens of vines, flowers, and trees. Anchoring the courtyard is a mature Cherry tree providing ample shade and stunning blossoms. The charming courtyard features a large brick terrace beneath a grapevine covered pergola, ideal for morning coffee or evening wine with birdsong. The walled courtyard and gardens are truly an eco-system for small indigenous wildlife, bees, and butterflies. The small, raised-bed garden is perfect for growing herbs. The forest can be seen upon entering the home and can be enjoyed by all spaces on the west side including the 3-sided 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. The foyer gives access to the fully private main suite including a large main bedroom with a window wall overlooking the forest and perfect for peaceful sleep. Aromatic, dual cedar-lined closets with built-ins, a spacious bath with windows opening onto the lush courtyard, a large tiled shower, a claw foot tub, two furniture-style vanity sinks, a large built-in storage cabinet, and a separate, private WC. The main wing hallway features floor-to-ceiling cabinets for generous storage that complete the main suite. Also, from the foyer lies a large, bright, and sunny flex room featuring a bay window with views of the courtyard. Butterfly bushes grace the view to provide a "Butterfly Ballet" when in season. The main level provides a spacious great room with soaring ceilings and views of the forest through the adjoining window-walled dining area. A custom stone fireplace anchors the room and features a 400-year-old historic mantle and is flanked on both sides with generous built-in bookcase/cabinets. 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). The hallway from the kitchen features two large pantries, a cedar-lined coat closet and access to the large, fully appointed laundry room all leading to the garage entrance. The spacious, light-filled laundry room features built ins, a custom, tiled dog shower, and pet feeding area. A pair of Maytag machines are included. Two more spacious bedroom/office rooms (one opens to the large, screened porch) and a charming full hall bath lie directly off the kitchen. The hall opens to a double garage with custom, epoxy coated floors and ample storage. Ample and convenient outdoor space is provided for pets. A door leads to a fenced, yard/dog run which extends the entire length of the southern side of the home. The other garage side door gives access to the courtyard for ease with gardening projects. The spacious lower level has been fully appointed with many custom finishes and a custom "Fearrington" mural to create a unique retreat complete with a bar, gaming, and TV area. The area is separated from a workshop space and high-ceilinged storage that houses dual HVAC systems. Located within a closet in the space is the whole-house water filtration system. Low-maintenance landscaping has been selected and is maintained by an extensive drip system.

1390 Bradford Pl, Pittsboro

650 Stonecrest Way, Pittsboro
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 10199904 MLS ⋅ ACTIVE Status
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

120 Hamlet Grove Dr, Pittsboro
$575,000
3 Beds ⋅ 3 Baths ⋅ 10199766 MLS ⋅ ACTIVE Status
Beautifully situated on a private, wooded lot, this inviting three-bedroom home combines comfortable living with thoughtful updates. Refinished hardwood floors, new carpet, fresh interior paint, and updated bathrooms with new tile and lighting give the home a fresh, move-in-ready feel. The kitchen features granite countertops, an eat-in island, and tile backsplash, and opens to the family room, where a gas fireplace creates a warm and welcoming gathering space. A separate living room opens to the dining room, offering additional space for relaxing and entertaining. The primary suite features a spacious bath with a separate shower and corner tub, along with a walk-in closet. The laundry room includes built-in cabinetry, a new countertop, and new tile for added style and convenience. Outside, a large deck overlooks the beautiful, wooded backyard, while a custom fire pit area with hand-selected boulders creates a special place to gather with family and friends or simply unwind in the peaceful surroundings. Ample parking provides plenty of space for family, friends, and guests. With no HOA, you can enjoy added flexibility in how you use your property. Conveniently located just minutes from downtown Pittsboro and Chapel Hill, this home is ready for you to move in and enjoy!

120 Hamlet Grove Dr, Pittsboro

2317 Alex Cockman Rd, Pittsboro
$899,000
4 Beds ⋅ 4 Baths ⋅ 10199888 MLS ⋅ ACTIVE Status
For a limited time, enjoy a $15,000 Builder 'Pay As You Choose' incentive, plus a First Citizens forgivable loan of up to $30,000 for qualified buyers--an exceptional opportunity to make this new custom home your own! Set on 1.34 private acres in Pittsboro with no HOA, the Mattie plan by Pine State Construction Group offers nearly 3,700 square feet of thoughtfully designed living space. Custom craftsmanship and elevated finishes come together with the freedom, privacy and space today's buyers desire. Designed for everyday comfort and effortless entertaining, the main level features an impressive owner's retreat, private guest suite, dedicated home office and open living areas filled with natural light. Engineered natural-oak hardwood floors, extensive trimwork, custom built-ins and a gas fireplace add warmth and character throughout. The statement kitchen showcases a sage-green island, dramatic Taj Mahal quartz countertops and backsplash, stained cabinetry, an apron-front sink, gold bridge faucet, custom range hood and beautifully designed coffee bar. Bi-parting doors extend the living area onto the covered rear deck, where mature trees and a peaceful natural setting create a private outdoor retreat. Upstairs, additional bedrooms and versatile living spaces provide room for guests, recreation, fitness and more. Outside, cedar timber accents, soft sage siding and a warm wood entry create distinctive curb appeal against the natural beauty of the acreage. Enjoy peaceful country living without sacrificing convenience--approximately two miles from Highway 64 and less than 10 minutes from downtown Pittsboro, with Jordan Lake and destinations throughout Chatham County within easy reach. Builder incentive and forgivable-loan program are subject to applicable terms, lender requirements, availability and buyer qualification.

2317 Alex Cockman Rd, Pittsboro

60 Farmingdale Ln, Pittsboro
$515,000
4 Beds ⋅ 3 Baths ⋅ 10199851 MLS ⋅ ACTIVE Status
Every home has a story, and this one is ready for its next chapter. Seller offering a credit toward a mortgage rate buydown for qualified buyers, subject to lender approval and agreed-upon contract terms. See documents for financing incentive details. Lovingly cared for and thoughtfully updated, this Potterstone Village home welcomes you with a rocking-chair front porch and spaces that invite you to settle in and stay awhile. From morning coffee on the deck to evenings gathered around the fireplace, it's easy to imagine the everyday moments that will make it yours. With four bedrooms, 2.5 baths, and 2,156 square feet, the layout offers room to gather and space to retreat. Hardwood floors flow throughout the main level, connecting a welcoming family room with gas-log fireplace to the kitchen and sunny breakfast area. White cabinetry, a subway-tile backsplash, and a new dishwasher complement the kitchen, while a separate dining room with a bay window and decorative molding sets the scene for holiday dinners and everyday celebrations. Upstairs, all four bedrooms are together, along with a convenient laundry room and newly installed Mohawk PureTech Plus waterproof plank flooring and carpet. The spacious primary suite features a vaulted ceiling and an adjoining sitting room with double doors... perfect for a home office, a favorite book, or a quiet start to the day. The beautifully renovated primary bath brings a little luxury to your routine with a 4-by-5-foot tiled walk-in shower, ceiling-mounted rainfall showerhead, handheld sprayer, heated towel bars, and a new double vanity with updated faucets and lighting. Step outside to an oversized, recently stained deck with built-in seating overlooking a large, level backyard. Raised garden beds offer space to grow your favorites, and the neighborhood pool is a short walk away. The recently stained front porch provides another inviting spot to unwind and greet neighbors. A roof replaced in 2021, updated lighting throughout, and a two-car garage round out the home's features. Set on .33 acre just minutes from downtown Pittsboro's shops, restaurants, and small-town charm, this is a home ready for new memories... and your next chapter.

60 Farmingdale Ln, Pittsboro

12 Macon, Pittsboro
$689,000
2 Beds ⋅ 2 Baths ⋅ 10199602 MLS ⋅ ACTIVE Status
THIS CHARMING HOME welcomes you with a private front courtyard, setting the tone for a space that feels both inviting and beautifully functional. Inside, the flexible dining room space has been transformed into a bright, efficient office with extensive built-ins, creating a perfect work from home set- up. A cheerful sunroom opens onto the courtyard , filling the home with natural light and serving as an ideal dining space. The living room features soaring ceilings and a cozy gas fireplace, flowing seamlessly into the kitchen where a large island, breakfast nook and the convenient pass through with bar sink, could be the coffee bar or cocktail bar. The Primary ensuite offers a walk-in shower and comfortable privacy, while the guest bedroom has convenient access to the hall bath. Through the separate laundry room, you can access the spacious outdoor space, fenced patio with pergola for shade and two gated points of entry, a perfect spot for relaxing outdoors. A 2 car garage, with cooling, lots of storage throughout and a layout that feels bright, open, and easy to live in. Come see it this weekend and experience how bright, welcoming and thoughtfully designed this home truly is. All this is just a short distance from the Village Center, convenient to the park, Belted Goat Cafe and our beloved bookstore....

12 Macon, Pittsboro

137 Evergreen Dr, Pittsboro
$449,000
3 Beds ⋅ 3 Baths ⋅ 10199504 MLS ⋅ ACTIVE Status
Freshly renovated and full of charm in the heart of Pittsboro! Situated on just over half an acre on a culdesac peaceful road. This 1,661-square-foot home is completely renovated it offers 3 bedrooms, 2.5 baths, and inviting curb appeal with a metal roof and easy-care landscaping. The main-floor primary suite features a beautifully updated bath with a walk-in shower. Upstairs, two additional bedrooms share a newly renovated, light-filled full bath. The ample kitchen shines with new maple cabinetry, quartz countertops, all new appliances. LVP flooring throughout adds style and everyday practicality. Rocking chair front porch. A spacious back deck overlooks the generous backyard, creating a welcoming spot to relax or entertain. New Windows and Blinds thru-out. Enjoy a small-subdivision feel with convenient access to Pittsboro's shopping, dining, parks, and in-town activities, plus easy connections to Highways 15/501, 87, 64, and 902.

137 Evergreen Dr, Pittsboro

231 High Ridge Ln, Pittsboro
$795,000
4 Beds ⋅ 4 Baths ⋅ 10199464 MLS ⋅ ACTIVE Status
Welcome to the highly desirable Chapel Ridge golf community! Ideally located just minutes from Chatham Park, with easy access to Apex, Cary, Chapel Hill, and I-540, this home offers everyday convenience with resort-style living. Designed for comfortable living and effortless entertaining, the open and spacious floor plan features plenty of natural light, a large kitchen island, a formal dining room, a cozy living room with a fireplace, and a seamless transition to the screened-in porch. The main level includes a private office, flexible living space, and a primary suite for convenient one-level living. Walk in pantry. Upstairs, the fourth bedroom features a wet bar and can easily serve as a bonus room, guest suite, or media space. Enjoy extensive walk-in storage and an oversized garage! Outside, a backyard koi pond offers a serene touch. This home offers a wonderful blend of space, functionality, and vibrant community living. For more information contact Judith at judith.delacruz@exprealty.com. Welcome to the highly desirable Chapel Ridge golf community! Ideally located just minutes from Chatham Park, with easy access to Apex, Cary, Chapel Hill, and I-540, this home offers everyday convenience with resort-style living. Designed for comfortable living and effortless entertaining, the open and spacious floor plan features plenty of natural light, a large kitchen island, a formal dining room, a cozy living room with a fireplace, and a seamless transition to the screened-in porch. The main level includes a private office, flexible living space, and a primary suite for convenient one-level living. Walk in pantry. Upstairs, the fourth bedroom features a wet bar and can easily serve as a bonus room, guest suite, or media space. Enjoy extensive walk-in storage and an oversized garage! Outside, a backyard koi pond offers a serene touch. This home offers a wonderful blend of space, functionality, and vibrant community living. For more information contact Judith at judith.delacruz@exprealty.com.

231 High Ridge Ln, Pittsboro

100 Freemont Ave Unit 214, Pittsboro
$579,900
4 Beds ⋅ 3 Baths ⋅ 10199120 MLS ⋅ ACTIVE Status
3-CAR GARAGE, MAIN-LEVEL GUEST SUITE & GOURMET KITCHEN! Discover the Kipling in Meadowview, offering 2,820 sq. ft., 4 bedrooms, 3 full baths and an exceptional combination of comfort and flexibility. The main level features an inviting Great Room, Dining/Study area and gourmet Kitchen with staggered cabinetry, Lyra quartz countertops, designer tile backsplash, gas cooktop and wall oven/microwave combination. A private main-level bedroom with full bath offers an ideal retreat for guests or multigenerational living. Upstairs, the spacious Primary Suite features a luxury tiled shower with seat, rain showerhead and dual vanity. Two additional bedrooms, convenient Laundry and a generous Bonus Room provide space for work, entertainment or relaxation. Enjoy designer black lighting, upgraded flooring, a covered front porch and rear patio. Meadowview offers a pool, clubhouse, playground, pickleball and trails near Pittsboro and Chatham Park.

100 Freemont Ave Unit 214, Pittsboro

115 Freemont Ave Unit 375, Pittsboro
$614,900
5 Beds ⋅ 3 Baths ⋅ 10199119 MLS ⋅ ACTIVE Status
3-CAR GARAGE, MAIN-LEVEL GUEST SUITE & GOURMET KITCHEN! Discover the Riley in Meadowview, offering 3,164 heated sq. ft., 5 bedrooms and 3 full baths with an impressive combination of space, style and flexibility. The main level features an open Great Room, Dining Room and gourmet Kitchen with staggered cabinetry, Black Waves granite countertops, designer tile backsplash, farmhouse sink, gas cooktop, wall oven/microwave combination and Butler's Pantry. A private main-level bedroom with full bath provides comfortable accommodations for guests or multigenerational living. Upstairs, the spacious Primary Suite features a luxury tiled shower with seat, rain showerhead, frameless glass enclosure and dual vanity, along with three additional bedrooms and convenient Laundry. Enjoy upgraded flooring, designer gold lighting, a welcoming covered front porch and covered rear porch. Meadowview offers a pool, clubhouse, playground, pickleball and trails near Pittsboro, Chatham Park and Chapel Ridge. Experience the space, thoughtful design and exceptional lifestyle the Riley offers at Meadowview--schedule your tour today!

115 Freemont Ave Unit 375, Pittsboro

3477 Castle Rock Farm Rd, Pittsboro
$1,300,000
4 Beds ⋅ 2 Baths ⋅ 10198647 MLS ⋅ ACTIVE Status
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

15 Breezewood Ct, Pittsboro
$530,000
4 Beds ⋅ 3 Baths ⋅ 10198596 MLS ⋅ ACTIVE Status
There's something special about a home with a welcoming front porch, comfortable living spaces, and room to grow. Located on a corner lot in Potterstone Village, this home offers 4 bedrooms, 2.5 bathrooms, 2,316 square feet, and thoughtful updates that make this home ready for its next chapter. Step inside to discover FRESHLY PAINTED interior (OCT 2026) , beautiful trim work, and hardwood floors that have just been buffed and finished with a fresh clear coat (OCT 2026). The kitchen features a brand-new stainless steel refrigerator (OCT 2026) and a newer electric range (2025). Upstairs, you'll find four bedrooms, an additional bonus room/office, and laminate flooring throughout the second level. Brand new laminate on the stairs. (OCT 2026) Whether you need space for hobbies, guests, or working from home, the flexible floor plan offers plenty of possibilities. One of this home's most appealing features is its outdoor living space. The wraparound front porch offers a wonderful place to enjoy your morning coffee, while the spacious screened porch provides a comfortable spot for relaxing or gathering with friends. Large fenced backyard and an additional parking pad adds everyday convenience. And there's more! A large unfinished third floor with walk-up access offers exciting possibilities for future use, subject to applicable permits and approvals. WATER HEATER: 2023, ROOF: 2022. Exterior Painted- 2020. Potterstone Village residents enjoy neighborhood amenities including a community clubhouse, swimming pool, and pond. Downtown Pittsboro, local restaurants, shopping, and schools are just minutes away, with convenient access to Highways 87, 15/501, and 64. Ready for it's next owner!

15 Breezewood Ct, Pittsboro

60 Rosefield Ct, Pittsboro
$1,900,000
5 Beds ⋅ 7 Baths ⋅ 10198589 MLS ⋅ ACTIVE Status
A captivating expression of French Provincial architecture, this extraordinary custom estate offers a rare blend of timeless elegance, exceptional craftsmanship, and resort-inspired living in the prestigious Chapel Ridge Estates golf course community. Custom built by Morningstar, it makes an unforgettable first impression with a striking stone and brick façade, graceful architectural details, circular drive, and beautifully landscaped grounds. Inside, graciously proportioned living spaces unfold across three expansive levels, showcasing rich Brazilian cherry hardwoods, 10-foot main-level ceilings, intricate millwork, coffered and tray ceilings, custom built-ins, and refined finishes throughout. Designed to accommodate both intimate gatherings and grand-scale entertaining, the home offers a seamless balance of sophistication and comfort. At the heart of the residence, a beautifully appointed chef's kitchen features a professional Wolf six-burner range with griddle, Sub-Zero refrigeration, dual dishwashers, and a butler's pantry—an exceptional setting for everything from quiet mornings to memorable dinner parties. A richly detailed private study, elegant formal dining room, and inviting gathering spaces elevate the experience of everyday living. The main-level primary retreat offers a serene escape with a spa-inspired bath featuring natural slate, a soaking tub, and dual showerheads. A second main-level guest suite with an accessible, curbless shower provides exceptional flexibility for guests or multigenerational living. Upstairs, additional bedroom accommodations, a private balcony, and an extraordinary boutique-inspired dressing room with custom cabinetry and display storage add another dimension of luxury and personalization. The finished lower level is an entertainer's destination of its own, complete with a custom bar, recreation area, distinctive stone-clad wine cellar, fitness room, and private guest accommodations—ideal for extended stays, recreation, or multigenerational living. Outdoors, the estate transforms into a private entertaining retreat. An expansive terrace, fully equipped outdoor kitchen, covered gathering spaces, motorized retractable screens, and multiple balconies create an inviting atmosphere for alfresco dining, sunset cocktails, and evenings beneath the stars. A striking exterior spiral staircase connects the outdoor living levels, while mature landscaping provides a beautiful natural backdrop. More than a residence, 60 Rosefield Court offers a distinctive lifestyle—where timeless architecture, thoughtful design, and effortless entertaining come together in one remarkable Chapel Ridge estate.

60 Rosefield Ct, Pittsboro

97 Cottage Way, Pittsboro
$1,035,000
5 Beds ⋅ 4 Baths ⋅ 10198458 MLS ⋅ ACTIVE Status
Welcome to this stunning home featuring an attractive board-and-batten exterior with elegant stone accents, an inviting arched double-door entry, and a charming stone-floored front porch! Enter inside the foyer to the view of four oversized picture windows spanning the family and dining rooms which draws in natural lighting. The gourmet kitchen features a spacious island and opens to an generous sized family room overlooking the covered porch. The expansive dining room offers plenty of space as well. The main-level primary suite features a beautiful tray ceiling, a luxurious soaking tub, and a spacious shower. A private study conveniently located off the foyer provides the perfect work-from-home space. Three of the four additional, generously sized bedrooms, feature large walk-in closets and direct access to full bathrooms. This home also features a spacious a media room, and walk-in storage providing flexibility.

97 Cottage Way, Pittsboro

400 River View Rd, Pittsboro
$536,000
2 Beds ⋅ 2 Baths ⋅ 10198382 MLS ⋅ ACTIVE Status
Picture yourself in the peace and beauty of a heart home. Inspired by hospitality and comfort. Surrounded by the healing essence of nature and crafted carefully into every detail of the home. A place to live, create and nurture. Known lovingly as Birds Nest, this cherished home is ready for its next generation. A magical refuge of almost 6 acres of forest with trails, a meandering creek, and open space for gardens and play. Custom built by hand of live edge pine clapboard, the home embraces the elements of wood, stone and mountain allure. Enter the rustic welcome deck made for tales, tonics, bird songs and gentle breezes. Step inside and admire the lodge-like two-story fireplace of hand stacked stones gathered from the land, the centerpiece of the open living room, kitchen and dining area. Bask in the mosaic light that flows through the rich colors of stained glass and feel the warmth of the artsy shiplap walls. Make your way up to the loft rooms for rest or retreat. Escape to the spa-like primary en-suite where you find privacy and provision with windows that showcase the outdoors as your living canvas. Located in the coveted Chatham County Haw River area in a sought-after large parcel neighborhood. Convenient to Pittsboro, Chapel Hill/Carrboro, Durham, UNC, RTP and RDU. Embrace the cabin life. Nothing about this property is ordinary or untouched by grace. This is home.

400 River View Rd, Pittsboro

246 Fox Rdg, Pittsboro
$539,900
3 Beds ⋅ 2 Baths ⋅ 10198340 MLS ⋅ ACTIVE Status
Tucked among the trees in the heart of historic Fearrington Village, this striking 3-bedroom, 2½-bath contemporary home offers modern design, exceptional craftsmanship, and serene wooded views from nearly every room. With its clean architectural lines and abundant natural light, the home lives like a private modern treehouse--peaceful, elevated, and beautifully connected to nature. Inside, thoughtful design meets everyday functionality. The kitchen features custom cabinetry, granite countertops, stainless steel appliances, tile flooring, and generous windows that fill the space with natural light. Custom cabinetry continues throughout the home in the bathrooms, closets, and laundry, creating a cohesive aesthetic and abundant storage. The spacious living areas showcase vaulted ceilings, skylights, hardwood floors, and a fireplace, all framed by expansive windows overlooking the surrounding woods. The flexible third bedroom offers endless possibilities--ideal as a home office, library, gym, craft room, or music studio. A two-car garage and a walk-in crawl space with a wine cellar provide exceptional storage options rarely found in homes of this size. Beyond the home itself, the lifestyle is what truly sets this property apart. Fearrington Village is consistently recognized as one of the Triangle's most desirable communities, offering a rare blend of charm, connection, and natural beauty. Residents enjoy the village shops and restaurants, the Tennis and Pickleball Association, and the opportunity to join the swim and croquet club. Outdoor living here is a way of life. Scenic walking trails and beautifully maintained gardens wind throughout the village. Visit the beloved Belted Barnyard animals or take a short drive to Jordan Lake for boating, swimming, hiking, and eagle-spotting. The nearby Haw River offers additional opportunities for kayaking, fishing, and peaceful exploration. Whether you prefer an active afternoon outdoors or a quiet morning walk among the trees, the options are abundant. Equally special is the sense of community. Fearrington Village is home to dozens of resident-run clubs spanning interests from arts and literature to fitness and travel, creating countless opportunities to connect and engage. The Fearrington Cares organization, founded to support the health and daily living needs of residents, further reflects the thoughtful and supportive spirit of the neighborhood. This is more than a home--it is a modern retreat set within a vibrant, connected community where nature, lifestyle, and neighborly warmth come together beautifully.

246 Fox Rdg, Pittsboro

14 Brushwood Ct, Pittsboro
$1,349,000
5 Beds ⋅ 5 Baths ⋅ 10198102 MLS ⋅ ACTIVE Status
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

174 Carillon Dr, Pittsboro
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 10198073 MLS ⋅ ACTIVE Status
Luxury, privacy, and exceptional craftsmanship come together on just over 10 serene wooded acres. Tucked away at the end of a private drive, this custom all-brick home offers a thoughtfully designed floor plan with primarily main-level living and incredible spaces for entertaining. The spacious living room flows into the keeping room and gourmet kitchen featuring an oversized eat-in island, abundant cabinetry and countertop space, plus a dream-worthy scullery. A formal dining room and dedicated home office provide additional flexibility. The private owner's wing is truly a retreat, featuring two spacious walk-in closets, two separate bath areas with individual vanities—one with a walk-in shower and the other with a soaking tub—plus an additional adjoining room ideal for a private office, reading room or nursery. Upstairs, two generous guest bedrooms share a hall bath. A separate bonus room with full bath above the three-car garage features its own entrance, creating an exceptional option for an in-law suite, private guest quarters or home business. Outside, enjoy your own private oasis with an in-ground fiberglass saltwater pool surrounded by the peaceful wooded setting. A whole-home generator and three-car garage add even more convenience. With over 10 acres, a private setting, flexible living spaces and custom details throughout, this is more than a home—it's a private retreat designed for the way you want to live.

174 Carillon Dr, Pittsboro

250 Hamamelis Ln, Pittsboro
$565,000
2 Beds ⋅ 2 Baths ⋅ 10197827 MLS ⋅ ACTIVE Status
An ENCHANTING oasis that inspires imagination, oneness with nature and serenity. This former artist's home is set beautifully on over 7 acres with direct access (and ownership) to the community lake. Redbud, a unique neighborhood that prides itself on a common respect for the environment, is 30 minutes from Chapel Hill and 15 minutes from downtown Pittsboro. As you drive into Redbud and pass the pristine community lake turn onto Hamamelis and feel like you've transported to a mountain retreat. The home is perched perfectly past the circular driveway, waiting for your arrival. Take the meandering stone path to the screened front porch. The main level features a soaring ceiling with huge windows letting natural light dance off the walls and the gorgeous refinished hardwood floors. Living and dining are combined with walls of windows and a wood burning fireplace. An office or small bedroom, full bath and studio/bedroom/flex room are also on the main level. The former art studio is staged as a potential main level primary bedroom or guest space. It is perced for 2 bedrooms with many possibilities for how to use the rooms in this home be it for work, play or meditation. Upstairs you'll find a large bonus room, another full bathroom with a garden tub surrounded by windows overlooking the vegetable garden area and yard. On the other side of the hall is another bedroom plus a sweet terrace overlooking the deck below and, of course, the expanse of rolling woods that make up this incredible lot. There's a custom built shed that's a work of art in itself plus another shed giving you lots of storage and workspace. The woods slope down along the creek inviting you to walk to the community lake for a picnic or perhaps to pick up a book in the community book box. 250 Hamamelis feels like home, where you fall asleep to the sounds of the cicadas and wake up to sip your coffee by the fireplace with full view of the majestic hardwoods and all their splendor. High speed internet through the HOA makes working from home feel like working from heaven. The sellers have provided a brand new Kinetico water filtration system, septic already pumped, refinished hardwoods, new carpet, fresh paint inside and out and a chance to own a home of your dreams.

250 Hamamelis Ln, Pittsboro

4230 Henderson Pl, Pittsboro
$1,175,000
4 Beds ⋅ 5 Baths ⋅ 10197735 MLS ⋅ ACTIVE Status
Discover exceptional comfort and timeless elegance in this fabulous 4-bedroom, 4.5-bath executive home, built by Homes by Dickerson in 2019. Offering over 3,400 square feet of beautifully designed living space on a professionally landscaped .96-acre lot, this home features an inviting open-concept floor plan, double front doors, rich red oak hardwood floors, crown molding, a formal dining room, and custom built-in bookshelves. The gourmet kitchen is a cook's dream, boasting granite countertops, a large center island, gas cooktop, walk-in pantry, and beverage center/coffee bar. Relax by the natural gas fireplace or enjoy the sunroom overlooking the beautifully maintained grounds. The owner's suite offers a recently remodeled spa bath, custom clothes closet, and thoughtful accessibility features. Exceptional upgrades include a Generac whole-house generator, tankless water heater, whole-house air purification and humidity control, encapsulated crawl space, irrigation system, and extensive drainage improvements. Enjoy outdoor living on the Tennessee Orchard stone patio, with a fenced backyard and gas hookup for grilling. The expanded garage and over 2,600 square feet of floored attic space provide outstanding storage and flexibility. Green Certified and meticulously maintained, this remarkable home combines luxury, efficiency, and convenience—all just minutes from Fearrington Marketplace, restaurants, and shopping. A truly special opportunity to enjoy the best of Fearrington Village living!

4230 Henderson Pl, Pittsboro

196 Paces Mill Trl, Pittsboro
$2,900,000
3 Beds ⋅ 3 Baths ⋅ 10197637 MLS ⋅ ACTIVE Status
A Majestic Haven on the Haw. Welcome to an extraordinary riverside sanctuary less than 20 minutes from the heart of Chapel Hill and the University of North Carolina. This gated almost 22-acre estate, gracing the banks of the majestic Haw River, seamlessly blends luxury living with natural splendor. The property features nearly a mile of private riverside trails, perfect for hiking or accessing the river for canoeing, kayaking, and fishing--with abundant bass, carp, crappie, sunfish, and bluegill. This enchanting refuge teems with wildlife. Deer regularly graze the grounds, while otters and beavers make their home along the riverbank. Bird enthusiasts will marvel at the diverse avian population, including majestic bald eagles, great blue herons, ospreys, warblers, and kingfishers. You may never see such beautiful sunsets as you do right at the comfort of your own home. Your home is comparable to this natural environment's beauty. Built in 2020 and designed by acclaimed architect Arielle Schechter--recognized among Forbes Magazine's 200 Best Residential Architects of 2025--this contemporary masterpiece showcases sophisticated design that harmonizes with its stunning setting. Breathtaking views of what many consider the river's most picturesque section are displayed through expansive windows, seemingly dissolving the boundary between indoors and out. Environmental consciousness meets luxury in this near net-zero residence, featuring: * Rooftop solar array * Geothermal heating and cooling * Triple-glazed European passive house windows and doors * Advanced water catchment system with dual 5,000-gallon cisterns * Solar reflective shades The property's resort-like amenities include: * Infinity pool with spa * Sauna * Steam shower * Separate workshop building with exercise room and upstairs bonus room * Private yurt with fenced yard. This secluded residential resort offers an unparalleled living experience that must be seen to be truly appreciated.

196 Paces Mill Trl, Pittsboro

220 Wendover Pkwy, Pittsboro
$598,500
3 Beds ⋅ 3 Baths ⋅ 10197403 MLS ⋅ ACTIVE Status
Seller is offering a $10,000 credit at closing toward the buyer's mortgage interest-rate buydown, subject to lender approval, loan-program limits, and agreed contract terms. Custom finishes and flexible living spaces distinguish this Chatham Park home in Pittsboro. At 220 Wendover Parkway, an added butler's pantry, updated paint, a custom half bath and detailed trim bring character to everyday living. The bonus room features wood flooring selected to match the first floor and a rich, dark palette that creates a cozy space for movies, hobbies or a home office. Added trim in the primary bedroom gives the room a finished, tailored feel. Garage built-ins provide organized storage alongside space currently used as a home gym. With 3 bedrooms, 2.5 baths and 2,412 square feet, the layout offers room to gather and space to spread out. Schedule a showing to see the finishes and layout in person.

220 Wendover Pkwy, Pittsboro

509 Cabin Crk, Pittsboro
$999,999
4 Beds ⋅ 4 Baths ⋅ 10197169 MLS ⋅ ACTIVE Status
MOTIVATED BUILDER NEEDS TO SELL ASAP TO MOVE ONTO OTHER PROJECTS! OPPORTUNITIES DO NOT COME AROUND LIKE THIS EVERYDAY! REDUCED FROM ORIGINAL PRICE OF $1,200,000 TO UNDER A MILLION! STUNNING NEW CONSTRUCTION CUSTOM HOME IN CHAPEL RIDGE! This beautifully crafted 4-bedroom, 3.5-bath custom home is ideally situated on .53 acres in the highly sought-after Chapel Ridge Golf Community. Thoughtfully designed with exceptional attention to detail, this home offers 2 bedrooms on the main level, including a spectacular Primary Suite with vaulted ceilings and a spa-inspired Primary Bath that is truly a masterpiece. Enjoy a beautifully tiled shower, luxurious soaking tub, dual vanities, and modern lighting. There are 2 electric water heaters to augment getting quick hot water. The impressive walk-in closet features custom built-ins and a huge center island/workspace perfect for folding, organizing, and storing clothing. The second main-level bedroom offers excellent flexibility for guests, an office, or additional living space. 10-foot ceilings on the first floor and 9-foot ceilings upstairs create an expansive and airy atmosphere throughout the home. The massive gourmet kitchen is designed to impress, featuring beautiful quartz countertops, generous counter space, abundant cabinetry, and exceptional storage. The spacious eat-in kitchen flows into a charming kitchen nook/keeping room area, creating the perfect space for casual dining and everyday gatherings. The Family Room provides a warm and inviting atmosphere centered around the fireplace—perfect for relaxing with family and friends. A thoughtfully positioned mudroom provides a practical drop zone for shoes, coats, and everyday essentials, while the main-level laundry room offers additional space for folding and organization. The oversized garage is an incredible bonus and offers room for two large trucks, a golf cart, and a riding mower—ideal for homeowners who need serious storage and workspace. Step outside to enjoy the screened-in porch, perfectly suited for outdoor entertaining and relaxing. The porch leads to a patio ready for grilling and additional outdoor gatherings. The wooded rear setting provides privacy, while the spacious backyard offers room for a future pool. Beyond the property, enjoy the peaceful natural setting with a creek buffer and neighboring cow pasture, creating a beautiful sense of privacy and country charm. Beautifully landscaped with irrigation system and engineered drainage. This exceptional custom-built home combines luxury, functionality, thoughtful design, and incredible outdoor living in one of Chapel Ridge's most desirable golf communities. A truly special home that must be seen to appreciate all it has to offer!

509 Cabin Crk, Pittsboro

97 Fox Oak Trl, Pittsboro
$1,172,000
4 Beds ⋅ 3 Baths ⋅ 10196801 MLS ⋅ ACTIVE Status ⋅ Custom Build BLDG.
Privately positioned at the end of a quiet cul-de-sac beneath a mature wooded canopy, this exceptional custom residence presents a rare opportunity to create a personalized luxury retreat on four private acres within Pittsboro's intimate Fox Oak neighborhood. As the build begins, a limited opportunity remains to collaborate with this award-winning design/build custom builder to personalize select finishes and details. Timeless elegance is elevated with sophisticated estate influences, beautifully proportioned living space, abundant natural light, and refined architectural details. Designed for gracious entertaining and effortless everyday living, the home offers an inviting sense of scale while maintaining the warmth and livability of a thoughtfully crafted custom home. At its heart, an impressive 21' x 17' Grand Room with soaring 12' ceilings creates a dramatic gathering space and flows seamlessly into the chef's kitchen, where a generous statement island and walk-in pantry combine sophisticated layout with exceptional functionality. The primary suite is envisioned as a private sanctuary, featuring a spa-inspired bath with dual vanities, freestanding soaking tub, expansive walk-in shower, and beautifully appointed custom walk-in closets with built-in wood shelving. Beyond the residence, the four-acre wooded homesite offers extraordinary privacy and the opportunity to create a true estate setting, with ample space to envision exceptional outdoor living while preserving the natural beauty and tranquility of the surroundings. Tucked at the back of the cul-de-sac in Fox Oak, an established enclave of distinctive custom homes, this property offers the privacy and presence increasingly difficult to find in desirable Pittsboro. Four private acres. Timeless architecture. Exceptional craftsmanship. A coveted cul-de-sac setting. And a limited opportunity to personalize the details before construction advances. A rare offering for the discerning buyer seeking more than a beautiful home—an opportunity to create a private estate that feels distinctly their own.

97 Fox Oak Trl, Pittsboro

473 Lila Dr, Pittsboro
$1,799,000
4 Beds ⋅ 6 Baths ⋅ 10196605 MLS ⋅ ACTIVE Status
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

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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