Shadymont Homes with Chatham - Northwood High High School

Welcome to Shadymont, an enchanting subdivision nestled in the picturesque town of Pittsboro, North Carolina. Located in the heart of Chatham County, this charming community offers the perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and everyone in between.

Shadymont is characterized by its beautifully designed homes, each reflecting a unique blend of modern aesthetics and traditional Southern charm. Whether you’re looking for a cozy starter home or a spacious residence for a growing family, you’ll find a variety of options that cater to diverse tastes and budgets. The lush, tree-lined streets provide a serene backdrop, inviting residents to take leisurely strolls and enjoy the natural beauty that surrounds them.

One of the standout features of Shadymont is its exceptional access to quality education. Families residing in this delightful neighborhood have the advantage of being part of the Chatham County school district, with Northwood High School just a stone's throw away. Known for its strong academic programs and dedicated faculty, Northwood High School is committed to empowering students and preparing them for future success.

In addition to its educational offerings, Shadymont boasts proximity to Pittsboro’s vibrant downtown, where you can explore quaint shops, delightful eateries, and community events that foster a strong sense of belonging. With its ideal location, welcoming atmosphere, and access to top-notch schools, Shadymont is not just a place to live; it’s a place to thrive. Discover your dream home in this captivating community today!

Newest Shadymont Homes with Chatham - Northwood High High School

$775,000

4 Beds ⋅ 3 Baths ⋅ 10179814 MLS ⋅ ACTIVE Status

Welcome to this stunning Cape Cod-inspired traditional home nestled on 2.81 private acres, offering over 4,000 square feet of beautifully designed living space. With 4 bedrooms, 3 full bathrooms, and an exceptional floor plan, this home combines timeless elegance with modern comfort. Step inside to discover soaring cathedral ceilings, beautiful hardwood floors, extensive crown molding, recessed lighting, and custom built-in bookshelves that add warmth and character throughout. The spacious living room is anchored by an electric fireplace, creating a cozy gathering space for family and friends. The beautifully appointed kitchen is designed for both function and style, featuring granite countertops, stainless steel appliances, and generous workspace for preparing meals and entertaining guests. A rare and highly desirable feature, this home offers two primary suites, providing flexibility for multi-generational living, extended family, or private guest accommodations The second floor features finished bonus rooms, offering endless possibilities for a home office, media room, playroom, fitness space, or additional guest accommodations. Enjoy peaceful mornings on the inviting rocking chair front porch complete with a porch swing, or relax year-round on the screened porch overlooking the peaceful wooded surroundings. The property also includes an attached double garage along with a detached garage/workshop, providing abundant space for vehicles, hobbies, storage, or projects. Recent improvements offer added peace of mind, including a new roof installed in 2025 and both heat pumps replaced in 2026. Additional features include a Ring® doorbell and security camera system. Conveniently located with easy access to Highway 64, this property offers the perfect balance of privacy, convenience, and country living.

26 Shadymont Dr, 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 .