Pittsboro Real Estate

Welcome to Pittsboro, North Carolina, a charming town nestled in the heart of Chatham County. Rich in history and surrounded by the natural beauty of the North Carolina countryside, Pittsboro offers a unique blend of small-town charm and modern conveniences. As you stroll through the quaint streets, you’ll discover a vibrant community that takes pride in its heritage and embraces the future.

Founded in 1785, Pittsboro is steeped in history, with many buildings reflecting its storied past, including the historic Chatham County Courthouse, which stands as a testament to the town's enduring spirit. The town is also home to a thriving arts scene, with local galleries and craft fairs showcasing the talents of resident artists. Whether you’re exploring the local shops or enjoying a meal at one of the delightful eateries, you’ll quickly feel the warmth and hospitality of this close-knit community.

Nature lovers will appreciate the proximity to the picturesque Jordan Lake, just a short drive away. This beautiful reservoir offers a plethora of outdoor activities, from hiking and bird-watching to boating and fishing, making it an ideal spot for families and adventure seekers alike.

Pittsboro is not just a place to live; it’s a place to thrive. With a growing economy and a commitment to sustainability, the town is attracting new residents and businesses, enhancing its appeal. Whether you’re looking for a peaceful retreat or a vibrant community to call home, Pittsboro is a hidden gem waiting to be discovered. Come experience the charm of Pittsboro, where history meets opportunity!

Newest Listings in Pittsboro

$375,000

3 Beds ⋅ 3 Baths ⋅ 10192649 MLS

If you're looking for a home in Powell Place that feels comfortable, practical, and easy to live in, 48 Danbury Ct is one I'd love for you to see. This 3-bedroom, 2.5-bath home sits on a corner lot and offers 1,510 square feet with an open floorplan that makes everyday living and entertaining feel simple. The living room features an electric fireplace with stone detail, upgraded light fixtures, while the kitchen offers a breakfast bar and a brand-new gas range. Step outside to the back deck and fenced backyard, where mature peach and apple trees add a little something special to the outdoor space. There is room to relax or simply enjoy your morning coffee. Multiple big- ticket items are already taken care of, including a new gas furnace in 2024 and a water heater replaced around 2022. Powell Place is one of those neighborhoods I enjoy recommending because it offers sidewalks, multiple community ponds, a playground, and access to Town of Pittsboro Park, all while being just minutes from downtown Pittsboro and Chatham Park. Shopping, restaurants, schools, and convenient access to Highways 64 and 15/501 are all close by. This is a great opportunity to own in a desirable Pittsboro neighborhood. 48 Danbury Ct is worth putting on your list. Professional Photos coming this week!

48 Danbury Ct, Pittsboro

$850,000

3 Beds ⋅ 4 Baths ⋅ 10192555 MLS

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

464 Deer Mountain Rd, Pittsboro

$599,900

2 Beds ⋅ 2 Baths ⋅ 10192550 MLS

ROSEBAY MODEL HOME OPPORTUNITY | Leaseback Option Available. Please call listing agents for more information on terms of sale. Welcome to the Rosebay by David Weekley Homes in award-winning Encore at Chatham Park! This exceptional model home opportunity offers the rare chance to own a professionally designed home with an impressive collection of upgrades and finishes. The thoughtfully designed Rosebay features a gourmet kitchen with gas cooktop, an open concept study, spacious roll-in shower in the Owner's Bath, tray ceilings in the Owner's Retreat and dining room, and expansive 8-foot sliding glass doors leading to the covered rear porch with a lovely view. Enjoy exceptional design, quality craftsmanship, and the lifestyle of Encore at Chatham Park. Don't miss your opportunity to make the Rosebay your new home!

167 Prospect Pl, Pittsboro

$890,000

10192533 MLS

Great opportunity to own a beautiful 32.988 acre tract of unrestricted land in Pittsboro. This fabulous tract of land features established pasture with extensive fencing, some mature hardwoods, well, 3-sided pole barn, shed, and has public road frontage. County Water is Available. Build your dream home, family compound, horse or dairy farm, recreational retreat, or future development. As per county, the property is zoned R-1 and is located within the Rural node of the county's land use plan. There is public water available so it can be subdivided. County approval is needed. Bring your own builder and build on your timeline—there is no time limit to begin construction. The land currently was perked for 5- 4 BR houses if someone wanted to do a minor subdivision. Seller has drawn up a map for potential 5 homesites, which is in documents. Enjoy the freedom, privacy, and flexibility that come with owning unrestricted acreage with endless possibilities. Property is currently being leased by a farmer and has cows on the land. 24 hour notice is required for a showing so the cows can be moved. Automatic waterers on the land are connected to the well but have not been used in many years so I do not know if they work as the farmer does not use them.

859 Pittsboro Goldston Rd, Pittsboro

$340,000

3 Beds ⋅ 3 Baths ⋅ 10192416 MLS

Adorable townhouse in desirable Powell Place- close to downtown and 15501/64 bypass for easy commute to Chapel Hill, Cary, Apex, 540. Open floor plan on first level with family room, large dining room and open kitchen. Upstairs boasts roomy master bedroom with full bath and two secondary bedrooms sharing another bath. No carpet, patio outside, landscaped yard, frig, washer, dryer convey. Great rental opportunity!

306 Danbury Ct, Pittsboro

$1,199,000

5 Beds ⋅ 6 Baths ⋅ 10192393 MLS

2026 Parade of Home Entry!! Are You Ready to Check Some Boxes!! How About 5 Bedrooms w/5 Separate Direct Access Full Baths!! Primary & Guest Bdrm on Main!! How about a Glass Enclosed Double Door Entry Study on Entry!! An 11' Ceiling 18x21 Trayed Family Rm w/FP Accented w/Cabinets, Shelving & Transoms!! Gourmet Kitchen w/Cabinets to Ceiling!! Stainless Steel Appliances & Vented Gas Cooktop w/7x7.5 Pantry/Scullery & Impressive Color Accented Island!! Next to a Vaulted Wall Accented Dining Rm!! Along with a 20x14 Wall Accented Primary w/an Incredibly Huge Wood Grain Looking Tile in the Oversized Glass Enclosed Zero Entry Shower w/Transom Window & Double Vanity Bath w/TALL Mirrors w/Large Free Standing Tub in between!! Large WIC w/His & Her Built-in Dressers & Natural Lighting via Nice Transom Window!! Mudroom w/Bench & Cubbies!! Laundry w/Cabinets w/Sink & Shelving on 2 Walls!! Upstairs Features 3 Adult Size Bedrooms w/Nice Views w/Full Baths & Nice WICs!! How about a Step Up Double Door 17.5x18.5 Game Room w/Nice View!! 2nd Floor Study/Flex Space!! Storage off Bedroom 4 WIC Closet!! OH! How about a Double Sky Light Vaulted Covered Back Porch w/Fire Place Pre Wired for TV!!! Large 21.5'x25.5' Garage w/Insulated Panel Garage Doors, EV Charging Source, & Tankless Gas Water Heater!! Spay Foam Insulation!! 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 with Access from Autumn Gate Street!! Retail right around the corner at the Mosaic!! The #1 Visited State Park Lake Jordan Minute Away!!

130 Autumn Gate St, Pittsboro

$788,000

5 Beds ⋅ 4 Baths ⋅ 10192347 MLS

Welcome home to this stunning property in the gated Parks at Meadowview community. Custom double front doors open into a light-filled, open layout featuring a first-floor guest suite. The beautiful gourmet kitchen shines with Dove Grey cabinets, quartz counters, an oversized island and abundant natural light. A three seasons porch and grilling deck overlook the wooded backyard and offers the perfect spot to enjoy nature year-round. Upstairs, the spacious primary suite includes a freestanding tub and walk-in closet, complemented by three additional bedrooms (all with walk-in closets) and a large bonus loft. Residents enjoy lovely green spaces, sidewalks, and a playground within the community. Conveniently located just 2 minutes from Chapel Ridge Golf Course, 22 minutes to Jordan Lake, and 30 minutes to UNC. Future neighborhood amenities are expected to include a pool, sports courts, and playgrounds.

1664 The Parks Dr, Pittsboro

$1,140,000

4 Beds ⋅ 4 Baths ⋅ 10192094 MLS

PARADE HOME | MOVE-IN READY MID-OCTOBER | 1.5 WOODED ACRES Privately nestled on 1.5 wooded acres just minutes from Chapel Hill, this exceptional custom residence—to be featured in the Chatham County Parade of Homes in October—offers a sophisticated blend of timeless architecture, elevated craftsmanship, and serene privacy, with move-in availability following the Parade. Designed for refined yet comfortable living, the striking exterior introduces exceptional outdoor spaces, including an expansive screened porch anchored by a dramatic stacked-stone fireplace—an inviting setting for year-round entertaining, relaxed evenings, and enjoying the peaceful wooded surroundings. Inside, soaring 10-foot ceilings and a dramatic two-story foyer create an impressive sense of arrival. Thoughtfully designed for both elegant entertaining and effortless everyday living, the home offers four spacious bedrooms and four beautifully appointed baths, including a luxurious main-level owner's retreat and private first-floor guest suite. At the heart of the home, the chef's kitchen pairs sophisticated design with exceptional functionality, featuring a 36-inch five-burner cooktop, oversized gathering island, and expansive walk-in pantry with custom wood shelving. Open, light-filled living spaces create a natural flow for entertaining while maintaining an inviting sense of warmth and comfort. Upstairs, thoughtfully curated spaces include a spacious media room, open loft, and private ensuite bedroom. A hidden "secret room" adds an unexpected and memorable element, offering endless possibilities as a private lounge, fitness studio, wine room, creative space, playroom, hobby room, or discreet additional storage. Exceptional craftsmanship, refined finishes, impressive indoor-outdoor living, and a private wooded setting distinguish this remarkable new construction custom home. Offering the rare combination of luxury, privacy, and proximity to Chapel Hill and Triangle amenities, this Parade Home presents an exceptional opportunity for buyers seeking a one-of-a-kind extraordinary residence.

4025 Hamlets Chapel Rd, Pittsboro

$825,000

3 Beds ⋅ 3 Baths ⋅ 10192091 MLS

Custom-Built Home on 1.06 Acres Convenient to Chapel Hill, Carrboro & Pittsboro.Welcome to 208 Tobacco Road, a beautifully maintained home offering an exceptional combination of space, privacy, and convenience. Set on just over an acre, this split-ranch provides the ease of one-level living with additional flexible space upstairs. The main level features an inviting open living area with beautiful solid oak flooring, 9-foot ceilings, a spacious kitchen with granite countertops and stainless-steel appliances, and a comfortable primary suite. Two additional bedrooms are also located on the main level, making the floor plan especially appealing for those seeking convenient first-floor living. One of the home's standout features is the large screened-in porch, creating a wonderful outdoor living space overlooking the private, low-maintenance property. The upstairs bonus room offers valuable flexibility for a home office, media room, exercise space, guest area, or hobby room. Additional highlights include an oversized two-car garage, generous storage, high ceilings, attractive landscaping, and a thoughtful floor plan designed for comfortable everyday living and entertaining. The location is equally appealing—convenient to downtown Pittsboro, Chapel Hill and Carrboro, with easy access to shopping, dining, Jordan Lake and the many amenities of the Triangle. Move-in ready, beautifully situated, and offering the rare combination of acreage, modern construction and convenient access to Chapel Hill and Pittsboro—208 Tobacco Road is a home you'll want to see.

208 Tobacco Rd, Pittsboro

$299,999

3 Beds ⋅ 3 Baths ⋅ 10191962 MLS

Welcome to 26 Danbury Ct. In fast growing Pittsboro NC, this home is convenient to downtown, shopping and dining. This is a McNeill Burbank home, a well respected Triangle builder w/green building practices. Great value! Main level includes wood floors, open living, front and back porches, with fenced low maintenance yard. Second floor has Primary with en-suite bath and 2 additional bedrooms/office space. Come see!

26 Danbury Ct, Pittsboro

$419,500

3 Beds ⋅ 3 Baths ⋅ 10191853 MLS

Welcome to 299 Millennium Drive, a pristine 3-year-old townhouse in the highly sought-after Chatham Park community of Pittsboro, NC. Offered at the incredible price of $419,500, this home has been lovingly cared for, offering a turn-key, like-new living experience with premier upgrades and total convenience. Home Highlights & Custom Upgrades Move-In Ready Quality: Meticulously maintained 3-year-old construction with a walk-in pantry, epoxy-finished garage floor, and an active HVAC maintenance agreement for total peace of mind. EV-Ready Garage: Equipped with an outlet in the garage ready for your electric vehicle charger. Private Outdoor Retreat: Features a backyard and a side privacy fence that backs up to peaceful, serene woods. Enjoy quiet forest views from your screened-in back porch, plus plenty of room for pets to exercise. Location & Community Chatham Park Amenities: Situated in Chatham Park, giving you instant access to all the vibrant entertainment, parks, and events the development has to offer. Active Lifestyle: Located near Paddles Swim and Pickleball Club! Unbeatable Convenience: Tucked away in a private, quiet neighborhood while remaining convenient to Hwy 64 and just minutes from local restaurants, shopping, and charming downtown Pittsboro.

299 Millennium Dr, Pittsboro

$535,000

3 Beds ⋅ 3 Baths ⋅ 10191826 MLS

BETTER THAN NEW HOME FOR SALE IN CHATHAM PARK! Built in 2022 by David Weekley Homes, and meticulously maintained by the original owners, this pet-free, smoke-free 3BR/2.5BA home offers an exceptional combination of modern efficiency, natural light and Chatham Park greenway living. The open-concept main level features a spacious kitchen flowing into the dining and living areas, plus a dedicated office/flex space. Upstairs, a generous loft provides a second living area surrounded by all 3 bedrooms. Relax on the covered rear porch overlooking the greenway and paved walking trail or enjoy the large covered front porch in this highly walkable Pittsboro community. Upgrades include a Kinetico K5 water filtration system with reverse osmosis, tankless gas water heater, encapsulated crawl space, whole-home surge protector, extended HVAC warranty and excellent garage storage. Remaining portion of the 10-year builder structural warranty conveys. ENERGY STAR®, EcoSelect Plus and Environments for Living® certified. Enjoy Chatham Park swimming, pickleball and trails, with Thales Academy within walking distance. Minutes to Jordan Lake for boating, hiking, fishing and camping and approximately 30 minutes to RDU International Airport and the Research Triangle. Why wait to build? Start enjoying the Chatham Park lifestyle in Pittsboro, NC today!

261 Mindees 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 .