Pittsboro Homes with Chatham - Pittsboro Elementary Elementary School

Welcome to Pittsboro, North Carolina, a charming town nestled in the heart of Chatham County. Known for its rich history and vibrant community, Pittsboro offers a delightful blend of small-town charm and modern conveniences. With its picturesque landscapes and friendly atmosphere, it’s no wonder that families and individuals alike are drawn to this enchanting locale.

Pittsboro is home to a variety of homes that cater to diverse lifestyles, from quaint cottages to spacious family residences. One of the standout features of this community is its proximity to Chatham - Pittsboro Elementary School, a highly regarded institution that emphasizes a nurturing learning environment. Families will appreciate the convenience of having quality education just a stone's throw away, making it easier for children to thrive both academically and socially.

The town itself boasts a vibrant downtown area filled with unique shops, local eateries, and cultural attractions. Enjoy leisurely strolls along the historic streets, where you can immerse yourself in the local art scene or savor a delicious meal at one of the charming restaurants. Outdoor enthusiasts will also find plenty to love, with nearby parks and natural spaces perfect for hiking, picnicking, and enjoying the beautiful North Carolina weather.

Whether you’re looking for a place to plant roots or a serene retreat from the hustle and bustle of city life, Pittsboro offers an inviting community that feels like home. Explore the possibilities and discover why so many are choosing to call this delightful town their own!

Newest Pittsboro Homes with Chatham - Pittsboro Elementary Elementary 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

$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

$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

$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

$820,000

4 Beds ⋅ 4 Baths ⋅ 10190708 MLS ⋅ ACTIVE Status

See Video Walk-through - Set on a private .43-acre wooded homesite in the sought-after golf community of Chapel Ridge, this spacious 3,474 sq ft home offers a wonderful combination of comfortable living, flexible space and a peaceful natural setting. The light-filled family room features a vaulted ceiling and gas fireplace, while the gourmet kitchen is beautifully appointed with white shaker cabinetry, quartz countertops, tile backsplash, gas cooktop and double ovens. The first-floor primary suite provides a relaxing retreat with serene wooded views, complemented by a dedicated home office and an oversized screened porch with tile flooring - an ideal place to unwind and enjoy the surroundings. The daylight basement significantly expands the living space with a large bonus/flex room, kitchenette, three additional bedrooms and two full baths, making it well suited for guests, recreation or multigenerational living. A lower patio, private wooded backyard and three-car garage complete the home. Beyond the property, Chapel Ridge offers a distinctive lifestyle amid rolling countryside, centered around an 18-hole championship golf course designed by JMP Golf Design and Fred Couples. Community amenities include a clubhouse, swimming, tennis, pickleball, fitness and athletic facilities, along with dining at the Golf Club. Enjoy the relaxed feel of country living while remaining convenient to Pittsboro, Chapel Hill and the greater Triangle.

55 Lookout Rdg, Pittsboro

$385,000

3 Beds ⋅ 3 Baths ⋅ 10190656 MLS ⋅ ACTIVE Status

Welcome to 284 Millennium Drive! This 3-bedroom, 2.5-bath townhome is ready to welcome you home. With an open and inviting layout, there's plenty of space to relax, entertain, and enjoy everyday life. Located in Chatham Park, you'll be close to parks, restaurants, shopping, and all the fun that comes with being part of this growing community. Just minutes from downtown Pittsboro, this home gives you the perfect mix of convenience, comfort, and community. Come take a look. You might just find your next favorite place to be!

284 Millennium Dr, Pittsboro

$430,000

4 Beds ⋅ 3 Baths ⋅ 10190550 MLS ⋅ ACTIVE Status

Welcome to 95 Roberts Street! This spacious 3-bedroom, 2.5-bath home offers multiple living areas, a formal dining space, and a roomy kitchen with plenty of cabinet and counter space. Enjoy the covered front porch, large covered back deck, and fenced backyard. Conveniently located just minutes from downtown Pittsboro with easy access to Chapel Hill, Cary, Raleigh, and Sanford. A great combination of space, comfort, and location!

95 Roberts St, Pittsboro

$1,185,000

5 Beds ⋅ 4 Baths ⋅ 10190532 MLS ⋅ ACTIVE Status

Another Custom Home Being Built by Gaylord Design Build! Now is a great time to walk this home and make it yours. See firsthand what's behind the walls, the attention to detail, and how well this home is being built....great bones, to say the least! No need to try to visualize the floor plan from a set of plans. Print the floor plan, walk through the home, and get a real feel for the room sizes, layout, furniture placement, and how the space works for you. Best of all, at this stage of construction, the home is still WIDE OPEN for personalization. Selections have not been finalized, giving you the opportunity to choose the finishes, colors, fixtures, and other details to make the home your own. Don't wait too long. As construction continues, those decisions will begin to be made. Right now is the perfect time to walk the home, see the quality of construction for yourself, and take advantage of the opportunity to personalize it before it's too late.

453 Golfers Vw, 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 .