Pittsboro Homes with Chatham - Northwood High High School

Welcome to Pittsboro, North Carolina, a charming town nestled in the heart of Chatham County. Known for its picturesque landscapes and vibrant community, Pittsboro offers a unique blend of small-town charm and modern conveniences. With its rich history, friendly atmosphere, and an array of outdoor activities, it’s no wonder that Pittsboro is becoming a sought-after destination for families and individuals alike.

One of the standout features of this delightful town is its proximity to Northwood High School, which is highly regarded for its commitment to academic excellence and community involvement. Families looking to settle down in Pittsboro will appreciate the educational opportunities available for their children, as Northwood High School is known for fostering a supportive learning environment. The school’s emphasis on holistic development ensures that students are well-prepared for their future endeavors.

The real estate market in Pittsboro is as diverse as its residents. From charming historic homes to modern new builds, there’s something for everyone. The neighborhoods surrounding Northwood High are particularly appealing, offering spacious yards, friendly neighbors, and a sense of community that makes it easy to call this place home.

In addition to its excellent schools, Pittsboro boasts an array of local shops, restaurants, and parks, making it a wonderful place to enjoy both relaxation and recreation. Whether you’re exploring the scenic beauty of nearby Jordan Lake or savoring the local cuisine, Pittsboro is a town that invites you to create lasting memories. Come discover the charm and warmth of Pittsboro—your new home awaits!

Newest Pittsboro Homes with Chatham - Northwood High High School

$725,000

4 Beds ⋅ 3 Baths ⋅ 10191572 MLS ⋅ ACTIVE Status

Secluded Jordan Lake home, beautifully maintained 1.5-story living on a park-like 3.5 acres with a pool and hot tub. Freshly updated and painted, this exceptional custom-built residence features a gourmet chef's kitchen with a center island, rich hardwood floors, and a stunning stone fireplace that anchors the warm, inviting living space. Enjoy year-round relaxation on the expansive screened porch, the front porch with swing, or meals on the back-dining porch. The spacious primary suite offers direct access to the deck and pool area. With four bedrooms and permits in place for an additional bedroom, the home offers incredible flexibility--including potential for an ADU or multigenerational living. Immaculate condition throughout, with Spectrum fiber, Starlink, and dual-fuel generator. Step outside and experience a true outdoor sanctuary with a fenced vegetable garden and mature perennial irrigated landscaping. Entertain with ease in the resort-style backyard featuring a saltwater inground pool, 8-person hot tub, flagstone patio with fire pit, and a tranquil Koi pond with blooming lotuses. Walk to Jordan Lake on a private trail/easement and enjoy boating, wildlife sightings, hiking trails, and even a nearby bald eagle's nest. Two 24-hour boat/kayak ramps are only 5 minutes away. At the end of a peaceful gravel country road yet located just minutes from downtown Pittsboro and 30 minutes from Chapel Hill and RDU, this one-of-a-kind property offers the perfect blend of tranquil HOA-free rural living with convenient access to dining, shopping, and amenities. Inspection report, repairs/improvements and invoices available.

450 Ryan Rd, Pittsboro

$819,000

4 Beds ⋅ 4 Baths ⋅ 10191393 MLS ⋅ ACTIVE Status

Meticulously maintained 4-bedroom home tucked away in a private wooded setting, encompassed by mature trees, situated on over 2 acres of secluded land. This property offers a perfect blend of convenience, peaceful countryside living, and modern comfort with a dynamic combination of indoor and outdoor living. As you walk through the front door you'll be greeted by an open family room featuring gas fireplace and surround sound speakers with a sitting/reading nook. Newly updated kitchen with new SS appliances, wall oven+microwave, 5-burner gas range with range hood, Corian countertops, custom pantries and cabinets, large breakfast nook, formal dining room, and access to sunroom with HVAC and surround sound speakers. Main level primary suite with vaulted 14' ceilings, gas fireplace, large custom closets, surround sound speakers, custom built-ins, Brazilian cherry hardwood floors, and gorgeous spa bath with huge frameless walk-in-shower, towel heater bar, and dual vanity. Laundry room with cabinets, counters, sink, and powder room completes the main level. Upstairs you'll find a 2nd primary suite with en-suite bath and huge WIC, 2 additional bedrooms and shared full bath with skylights. Walk out basement with large entertainment/rec room featuring surround sound speakers, pool table and bar. Rec room can be converted into 2-car garage. Basement also includes 1 car garage with custom shelving, workshop, exercise/storage room, and newly encapsulated crawlspace. Pool table and fridge in rec room + safe in workshop convey with the home. Incredible outdoor living! Expansive back deck and brick wraparound patio with outdoor grill and composite decking tops, 24 ft diameter 15,000 gallon pool with water slide and zipline, poolside shower with hot and cold water, pool house, and also plumbed for heated pool! 2 more outbuildings on the property, all hooked up with electricity. Charming front porch with swing. Other features include: expansive parking for RV, boats, cars, etc. Private well water with filter and upgraded 1-hp pump. Water iron remover tank in workshop. CPI alarm system. Dimmer lights throughout home. Situated on a high pitch/elevation for flood and rainwater aversion. All natural gas appliances. All additions are permitted. Freshly graveled driveway. New interior paint. Natural gas generator. Invisible fence. Irrigation system. Trail with bridge around the lot for walking or biking. This home is truly a retreat, don't miss your chance, schedule a showing today!

89 Lauren Ct, Pittsboro

$1,165,000

4 Beds ⋅ 5 Baths ⋅ 10191378 MLS ⋅ ACTIVE Status

Privacy is the luxury you'll feel first at 410 Berry Patch Lane. Custom built in 2023 on 1.19 wooded acres in gated Chapel Ridge Estates, this home pairs the freshness of recent construction with the mature trees and settled character of an established neighborhood. Even in winter, the woods screen neighboring homes.Start the day on the screened porch, listening to birdsong and watching for deer in the yard. In fall, fold the accordion doors completely open and settle in for a movie on the porch, with the sound of the wood-burning fireplace crackling inside. At sunset, unwind in the included saltwater hot tub as the clouds take on the evening's color. Inside, 11-foot main-floor ceilings and wood beams bring modern farmhouse character to the kitchen, living room, and primary suite. Custom accent walls add personality, while the kitchen's generous island makes room for conversation. The 4,202-square-foot layout offers four bedrooms and 4.5 baths, including two main-floor suites. The primary suite opens privately to the porch and has two custom walk-in closets, one connected by a pocket door directly to the laundry room. Upstairs, one oversized bonus room serves as a wellness and recreation space. Another is a large home office, with distinctive ceiling details and room for a substantial desk and separate sitting area. These are spaces to shape around your routines, with room for focused work and time to recharge. Custom closet built-ins throughout, substantial walk-in storage upstairs, an accessible sealed crawl space, and a three-car garage with epoxy floors make daily life easier. A whole-house generator adds backup power. The property extends to a creek and backs near the fourth tee of Chapel Ridge's championship course, with seasonal golf views through the trees. Convenient access to US 15-501, US 64, shopping, restaurants, and MOSAIC keeps everyday essentials within reach. Come sit on the porch and experience the quiet for yourself. More details Architecture and gathering spaces A flagstone front porch and arched wood entry door introduce the home's farmhouse character. Wood beams continue through the kitchen, living room, and primary bedroom. Accent walls added in the primary bedroom, study, upstairs media room, and upstairs office give individual spaces their own character. A stone surround, hearth, wood mantel, shelving, and cabinetry make the wood-burning fireplace a natural focal point. The French-door study on the main floor provides another separate space for reading, conversation, or work. Kitchen and everyday organization The kitchen includes Café cooking appliances and two built-in ovens, a Bosch refrigerator, Fisher & Paykel double-drawer dishwasher, a farmhouse sink, and a pot filler. Tall soft-close cabinetry and a walk-in pantry with custom wood shelving provide generous storage. The laundry room includes a sink and folding surface; its pocket-door connection to a primary closet makes putting laundry away particularly convenient. Custom built-ins throughout the closets help make the storage useful from the start. Suites and space upstairs The main-floor primary suite combines private porch access, two walk-in closets, a soaking tub, and a custom tiled shower with Moen temperature-setting controls. A second main-floor suite gives guests their own bedroom and bath. Upstairs are two additional bedrooms, a media room, and the oversized spaces currently used for wellness/recreation and a large office. The wellness room accommodates yoga, exercise, and recreation; the office has room for both a generous desk and a sitting area beneath its distinctive ceiling lines. Outdoor living and the wooded setting The screened porch has a wood ceiling, two ceiling fans, and a pull-down movie screen. Fully opening accordion doors connect it to the living room, and the primary suite has its own porch entrance. An adjoining open deck offers another place to enjoy the outdoors. The new Caldera saltwater hot tub with waterfall Home also has 3 electrical boxes with one being pre-wired for a built-in swimming pool. Flagstone design driveway across the entryway. Gutter guards, Beadboard for outdoor patio and front porch ceilings, Design Wall in Office on left upon entry, Wood Beams in Living space, Primary Bedroom with wood Beams, Flagstone Porch and Flagstone steps, French doors, Breakfast Bar, Walk-in Pantry with Coffee Bar, Oversized Leathered Granite island and Granite countertops. 11 foot ceilings. Designer Lighting, Walk in Crawl Space with plenty of storage. There is a utility 30 ft clearance that is cleaned yearly. See documents. There is a conservation zone so that no one will be building right next to you.

410 Berry Patch Ln, Pittsboro

$2,700,000

5 Beds ⋅ 7 Baths ⋅ 10191313 MLS ⋅ ACTIVE Status

This offering totals 26.71 acres across 4 combined parcels, with 2 developed residences, two septic systems, 1 shared well, and 2 buildable 3+ acre lots. From the moment you step inside, cathedral ceilings and floor-to-ceiling windows open every room to views of the land, so the changing seasons, deer moving through the meadow, and fireflies at dusk become part of everyday life rather than something you have to leave home to see. 319 Wrights Way (10.39 acres) is a 5,466 SF, 4-bedroom, 4.5-bath home, featured in NC Modernist Homes, engineered from eight inches of precast concrete, virtually indestructible, with passive solar design, radiant heated concrete floors, a wood stove, and a main-floor primary suite with forest and creek views. Custom cabinetry throughout was handcrafted by a local master woodworker, and details like reclaimed hardwood floors, stained glass, and recycled bottle-glass tile add warmth throughout, up to a lookout tower reached by a ship's hatch. The walkout level adds a media/game room, a gym with infrared sauna, and a creekside hot tub alcove. 321 Wrights Way (10.08 acres) adds a 1,655 SF guest residence backed by a verified five-year short-term rental history, with 1 bedroom, a spacious loft, and 1.5 baths, a four-car garage/workshop wired for a car lift, and a private office. Two additional buildable parcels (3.24 and 3 acres) round out the offering, ideal for a family compound or future income property; all four convey together. Nearly 1,600 feet of frontage runs along Terrell's Creek, with miles of wooded trails, a cleared meadow, a 4,000-square-foot fenced garden and chicken coop, daily sightings of deer, bunnies, and salamanders, and rarer visits from turkeys, turtles and even a black bear. A private drive keeps the setting quiet and secluded, minutes from Pittsboro, Chapel Hill/Carrboro, and Jordan Lake. Wrights Way is a rare kind of home, one you can live in every day and still admire like a piece of fine art. No picture does it justice. Schedule your private tour today.

319 Wrights Way, Pittsboro

$1,195,000

5 Beds ⋅ 5 Baths ⋅ 10191264 MLS ⋅ ACTIVE Status

Upscale, established neighborhood in growing Chatham County. Enjoy the quiet and privacy of this beautiful home, perfectly positioned on 2.84 acres at the end of a cul de sac. This property offers both interior and exterior features that deliver that "it's good to be home" feeling. The open main level includes a living room, a family room with a gas fireplace, and a chef's kitchen. The kitchen features a large island, upscale appliances, abundant counter and cabinet space, and a spacious pantry. The side entry garage leads into a generous drop zone and laundry room. The primary bedroom is light and roomy, connecting to a spa like bath and a well appointed walk in closet. The second level offers three additional bedrooms plus a dedicated office. The basement includes another bedroom and full bath, a bonus room, flex space, and additional storage. Outdoor living shines here — a huge deck overlooks a massive patio with a beautiful outdoor fireplace. A charming water feature enhances the setting. Beyond the fenced area is a small stream (a portion of the land near the stream is in the flood zone, not the house; conservation rules apply to the stream area). All of this is located in Chapel Ridge, a community loaded with amenities: pool, fitness center, tennis, and multiple recreational options included in the HOA fee. Golf is available for an additional charge.

148 Hidden Creek Ct, Pittsboro

$445,000

3 Beds ⋅ 2 Baths ⋅ 10191225 MLS ⋅ COMING SOON Status

Thoughtfully Renovated Ranch on over 5 acres! Built in 1970 and refreshed from top to bottom, this 3 bedroom, 2 bathroom home sits on 5.5 acres in Pittsboro, offering comfort, space, and peace of mind. Recent upgrades include a heat pump and central AC system installed October 2022 with a thermostat, a metal roof installed in 2018, and a mold-remediated, sealed crawlspace with a dehumidifier. Inside, the sellers opened up the main living space, creating a bright, free-flowing layout accented by crown molding in the dining room. Popcorn ceilings have been removed and freshly painted throughout, and the kitchen features replaced countertops with freshly painted cabinets. Both bathrooms have been updated, and the hall bath was enlarged to include a new closet. You'll also find updated interior doors, baseboards, light fixtures, outlets, switches, and covers throughout.

978 Elmer Keck Rd, Pittsboro

$175,000

10191135 MLS ⋅ ACTIVE Status

Convenient to the amenities, this lovely lot backs up to a wooded area for lots of privacy and has views of the small park area from the front.

12 Cabin Crk, Pittsboro

$1,168,000

4 Beds ⋅ 3 Baths ⋅ 10191052 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 home represents a rare opportunity to create a truly personalized luxury residence on four private acres within Pittsboro's intimate Fox Oak neighborhood. With construction beginning soon, there is a limited opportunity to reflect your personal tastes, in collaboration with this award-winning design/build custom builder. Inspired by timeless modern farmhouse architecture and elevated with sophisticated estate influences, the residence is thoughtfully designed for elegant entertaining and effortless everyday living, with beautifully proportioned living spaces filled with natural light. At the heart of the home, a 21'x17' Grand Room with 12' ceiling flows seamlessly into an impressive chef's kitchen with island and walk in pantry. The luxurious primary suite is designed as a serene private sanctuary, with a spa-inspired bath featuring dual vanities, soaking tub, walk-in shower, and his and custom walk-in closet with built-in wood shelving. Beyond the residence, the four-acre setting offers remarkable privacy and an extraordinary canvas for a private retreat. Set at the back of the cul de sac in Fox Oak, an established enclave of distinctive custom homes, this exceptional property combines the presence of an estate style setting with a short window to personalize your home as it comes to life. A rare opportunity to create something truly your own—where timeless architecture, exceptional craftsmanship, four private acres, and thoughtfully curated design come together in desirable Pittsboro.

97 Fox Oak Trl, Pittsboro

$140,000

10191003 MLS ⋅ ACTIVE Status

Build Your Vision in Pittsboro! Opportunity awaits on this 1-acre R-1 zoned lot, conveniently located just minutes from Downtown Pittsboro. This property offers the perfect opportunity to secure land in one of Chatham County's growing communities while remaining close to local shops, restaurants, entertainment, and everyday conveniences. Whether you're looking to build your next home or add land to your investment portfolio, this location provides flexibility and convenience. Enjoy the best of Pittsboro with easy access to surrounding communities and major thoroughfares. Bring your vision and make this property your own!

Tbd Richardson Rd, Pittsboro

$990,000

4 Beds ⋅ 3 Baths ⋅ 10190826 MLS ⋅ ACTIVE Status

Convenient to the amenities, this lovely lot backs up to a wooded area for lots of privacy and has views of the small park area from the front. Bring your own builder or use ours.

12 Cabin Creek Crk, Pittsboro

$375,000

3 Beds ⋅ 2 Baths ⋅ 10190815 MLS ⋅ ACTIVE Status

A sweet downtown Pittsboro home with space, updates, a fenced yard, and a setting that is increasingly hard to find. Tucked at the end of a cul-de-sac, this charming 3-bedroom, 2-bath cottage offers a bright, comfortable interior with hardwood floors throughout the main living areas. The kitchen features white cabinetry, granite countertops, and stainless steel appliances. The main-level primary bedroom has a vaulted ceiling, Palladian window, walk-in closet, and convenient access to a full bath. Upstairs are two spacious bedrooms and a second full bath. Recent improvements include a newer roof, HVAC system, hot water heater, and fresh interior paint. Outside, enjoy a large elevated deck overlooking the fenced backyard, along with a separate storage shed. All this just minutes from downtown Pittsboro's restaurants and shops, the library, schools, and nearby walking trails.

51 W Field St, Pittsboro

$849,500

4 Beds ⋅ 4 Baths ⋅ 10190765 MLS ⋅ ACTIVE Status

Set on more than two wooded acres, this custom-built home offers privacy and quality finishes at every turn. Fresh interior paint and new carpet complement the home's already-rich hardwood floors, detailed trim, and crown molding. The kitchen anchors the main floor w/ stainless appliances, granite counters, custom cabinetry, a center island with bar seating, spacious pantry, and a breakfast nook that catches the morning sun. A see-through gas fireplace opens the kitchen and breakfast area to the two-story family room, where a wall of windows keeps the whole space bright. The dining room and living room/office add flexibility to this level. A guest bedroom and full bath round out the first floor, along with a laundry room w/ cabinets, utility sink, and tile floors. Upstairs, the owner's suite has hardwood floors, crown molding, a walk-in closet with custom shelving, and a bath with a double vanity, jetted tub, walk-in shower, and separate water closet. Bedrooms three and four share a Jack-and-Jill bath with two vanities; bedroom five has its own walk-in closet and direct access to the hall bath. The third floor adds a bonus room with two closets and access to floored attic storage. The backyard oasis has a large deck, stone patio, and gazebo tucked into the trees. Behind the property, an additional 2.7 acres of HOA-owned open space includes a 1.5-2 mile trail, reachable from the garden at the top of the yard. This one-owner home has been well-cared for and now move-in ready. Downtown Pittsboro, Chapel Hill, and Jordan Lake are all a short drive away!

93 Wild Rose Ln, Pittsboro

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