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New homes in Pittsboro

Ryan's Crossing

Steeped in local history, Ryan’s Crossing honors the land and the families who settled in this location over a century ago. Sitting on 114 acres, this property was home to the Tripp and Ryan families, and our name and vision for Ryan’s Crossing pay homage to those pioneers who lived and worked on this land back in the early 1800s.

To preserve the history of this beautiful land, the streets are named after members of the Tripp and Ryan families, and the stone fireplace has been preserved from the original cabin where they once lived.

Ryan’s Crossing is perfectly situated close to all the conveniences of Chapel Hill but within the tranquility of Chatham County and Pittsboro. The community has set aside 46 acres of land to naturally preserve its wildlife habitat and expansive views.

The neighborhood will feature nature trails, a half-mile exercise loop, a yoga pavilion, and more to enjoy the peaceful surroundings. With 60 scenic estate-worthy homesites planned, we celebrate the relationship between nature and living well at Ryan’s Crossing.

Homes For Sale

441 Lila Drive
Ryans Crossing
$1,670,000 | 4 BR | 4.5 BA | 4437 SQ FT
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346 Lila Drive
Ryans Crossing
$1,740,000 | 4 BR | 6.0 BA | 4507 SQ FT
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20 Lila Drive
Ryans Crossing
PENDING SALE | 4 BR | 7.5 BA | 4652 SQ FT
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480 Lila Drive
Ryans Crossing
PENDING SALE | 4 BR | 5.5 BA | 4748 SQ FT
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About the AreaPittsboro

Located in the heart of Chatham County, Pittsboro, North Carolina is a picturesque town that blends Southern charm with a growing, modern community. Just a short drive from Chapel Hill, Cary, and Raleigh, Pittsboro offers a peaceful lifestyle with easy access to Triangle amenities.

At the center of town is the historic courthouse circle, surrounded by locally owned shops, cafes, art galleries, and restaurants. Cultural events, such as First Sundays and the Chatham County Fair, highlight the town’s creative spirit and community involvement.

Nature enthusiasts enjoy the Haw River and nearby Jordan Lake for boating, fishing, and hiking. The surrounding countryside features rolling farmland and scenic landscapes, ideal for those seeking a rural retreat while remaining connected to the Triangle.

Pittsboro is home to strong schools, a close-knit community, and convenient amenities, making it a perfect choice for families and professionals. 

With a rich history, vibrant culture, and access to the natural beauty of Chatham County, Pittsboro is more than a town—it’s a community where residents can enjoy a balanced, fulfilling lifestyle.