Pittsboro Real Estate Search

Pittsboro NC Real Estate & Homes for Sale

Our website features the best Pittsboro real estate search for homes, condo, and land properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Pittsboro Properties for Sale

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Pittsboro Homes for Sale

372 Firefly Overlook Rd, Pittsboro
$2,150,000
5 Beds ⋅ 7 Baths ⋅ 10142171 MLS ⋅ ACTIVE Status
Your custom sanctuary in Firefly Overlook awaits. Discover the serenity and sophistication of Firefly Overlook at Jordan Lake—a premier new large-lot subdivision featuring just 30 exclusive homesites in the rapidly growing and highly desirable Chatham County. Perfectly positioned for effortless access to Apex, Pittsboro, Cary, and RDU Airport, this thoughtfully planned community places you moments from the pristine shores of Jordan Lake while offering a peaceful, nature-immersed retreat with rolling hills, panoramic views, and tranquil natural surroundings. This exceptional pre-sale opportunity on Lot 27—a beautifully central 1.55-acre homesite that enjoys prime visibility and prominence within the neighborhood—invites you to collaborate with renowned Triple A Homes to create your fully customized dream residence. The inspiring proposed design draws from Triple A Homes' award-winning plan, previously celebrated for its timeless elegance and innovative layout, and can be tailored entirely to your vision with personal selections, modifications, or unique enhancements. Envision this magnificent to-be-built custom home: a light-filled masterpiece featuring 5 luxurious bedrooms, including a serene primary suite and convenient main-level guest suite for ultimate comfort and privacy. The heart of the home is an expansive two-story great room with dramatic open-to-above volume, complemented by abundant oversized windows and large retractable doors that seamlessly blend indoor and outdoor living—flooding the spaces with natural light and creating the sensation of being enveloped by nature year-round. The gourmet designer kitchen flows into a dedicated scullery for effortless entertaining, while a bespoke wine cellar adds sophisticated charm. Step outside through the retractable doors to a spacious covered patio complete with a cozy fireplace—perfect for al fresco gatherings and quiet evenings under the stars. Lot 27's central location offers exceptional curb appeal and easy connection to the community's natural beauty, making your future home a standout landmark in this intimate enclave. Secure this rare central homesite today and partner with Triple A Homes to bring your personalized legacy residence to life. Construction timeline and customization details available upon inquiry.

372 Firefly Overlook Rd, Pittsboro

66 Romie Ct, Pittsboro
$1,095,000
5 Beds ⋅ 5 Baths ⋅ 10165584 MLS ⋅ ACTIVE Status
Now offered at $1,095,000: luxury living inside and an entertaining paradise outside, plus all the behind-the-scenes upgrades that allow function and beauty blend seamlessly. You won't want to miss the opportunity at this price! Now offered at $1,095,000: luxury living inside and an entertaining paradise outside, plus all the behind-the-scenes upgrades that allow function and beauty blend seamlessly. You won't want to miss the opportunity at this price! Tucked at the end of a quiet cul-de-sac in one of North Chatham's most coveted communities, 66 Romie Court (5 bedrooms, 4.5 baths) is the rare home that genuinely delivers on the promise of work-life balance without sacrificing a single luxury. Functional upgrades include a 24KW Generac whole-home generator, a whole-home reverse osmosis filtration system, an under-counter UV filtration tap, a robust Guardian home security system, a sealed crawlspace, a Rinnai tankless water heater, and hard-wired data ports throughout for seamless working, streaming, and gaming. Fresh interior paint and recessed lighting welcome you into a sunny, open downstairs floor plan designed for comfortable daily working, living, and effortless entertaining. The four-season room with large sliding glass doors off the main living area invites you to breathe deeply, slow down, and take in the wooded surroundings in every month of the year. A downstairs en-suite bedroom gives you a perfect place for guests or anyone who needs a more accessible space. Upstairs, a spacious primary suite with a second three-season room, brand new carpet, a soaking tub, and a huge walk-in closet echoes the calm of the space downstairs. Three additional upstairs bedrooms give everyone ample room to spread out. Head up to the third level for over 700 square feet of flex space to meet any need, including a built-in projector and sound bar for a luxe home entertainment experience. The 3-car garage and widened driveway make it easy to get in and out and provide tons of storage. When you're ready to get outdoors, head down to your 15'x30' deck-level pool, complete with a built-in stone grill, dining and lounge space, mature trees, and a privacy fence for total seclusion. Gardeners will love the bounty of 10+ mature blueberry bushes and two magnificent 30-foot "Fruit Cocktail" trees bearing plums, nectarines, peaches, and apricots throughout the year, and four raised garden beds with drip irrigation for easy, sustainable growing. With approximately 40 homes spread across 1+ acre lots, this North Chatham neighborhood offers the rare combination of true privacy and genuine community, all within easy reach of Chapel Hill, RTP, and growing downtown Pittsboro.

66 Romie Ct, Pittsboro

45 Quail Pt, Pittsboro
$1,299,950
4 Beds ⋅ 5 Baths ⋅ 10160405 MLS ⋅ ACTIVE Status
Grading is complete and permits are in place now is your chance to have your dream home overlooking Hole #2 of the highly sought-after Fred Couples Signature 18-hole golf course in the next 12 months. This thoughtfully designed 4,323 sqft home features an open and airy layout with 10 ft and 19 ft ceilings on the main level and 9 ft ceilings on the second floor, creating a bright and expansive feel throughout. The home offers 4 spacious bedrooms and 4.5 bathrooms, all secondary bedrooms are en-suite for ultimate comfort and privacy. The chef's kitchen is a true centerpiece, showcasing ceiling-height cabinetry, quartz countertops, stainless steel Bosch appliances, and a 36-inch gas range. A separate scullery kitchen adds both functionality and elegance. The kitchen flows seamlessly into the main living area, highlighted by a 48-inch gas fireplace and large sliding patio doors that open to a backyard with beautiful golf course views. Additional features include hardwood flooring throughout the main living areas, carpet in the bedrooms, and a tankless water heater for efficiency. A dedicated gym or media room and a spacious loft overlooking the main level provide flexible living and entertainment spaces. Situated on a private homesite, the property also includes a 3-car garage. Located in Chapel Ridge, residents enjoy resort-style amenities including a clubhouse, pool, fitness center, pickleball courts, tennis courts, volleyball, basketball, a soccer field, and, of course, championship golf.

45 Quail Pt, Pittsboro

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

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