Winding Woods Homes for Sale

Welcome to Winding Woods, a picturesque subdivision nestled in the heart of Asheboro, North Carolina. This charming community in Randolph County offers a serene and inviting atmosphere, perfect for families, retirees, and everyone in between. With its lush landscapes and winding roads, Winding Woods is designed to provide a tranquil escape while still being conveniently located near the vibrant amenities of Asheboro.

Homes for sale in Winding Woods embody a blend of modern comfort and classic charm. Each property showcases thoughtful designs, spacious layouts, and beautiful finishes, catering to a variety of lifestyles and preferences. Whether you're seeking a cozy single-family home or a larger residence to accommodate your growing family, Winding Woods has options that will delight you. Many homes feature expansive yards, ideal for outdoor gatherings, gardening, or simply enjoying the tranquility of nature.

Asheboro itself is a lively city known for its rich history and community spirit. Residents can enjoy easy access to local parks, shopping, dining, and cultural attractions, including the renowned North Carolina Zoo. The area is also known for its excellent schools, making it an ideal choice for families looking to settle down.

Explore the homes for sale in Winding Woods and discover the perfect place to call home. With its idyllic setting and welcoming community, Winding Woods is more than just a neighborhood; it's a place where memories are made and dreams come true. Don’t miss your chance to be part of this enchanting community!

Newest Winding Woods Homes for Sale

$474,900

3 Beds ⋅ 2 Baths ⋅ 1229477 MLS

Tucked away down a long, winding driveway on over six private acres in Southwest Asheboro, this custom Cape Cod is a true country sanctuary. Masterfully built from 2021 to 2026, this home is truly one of a kind—from vintage-style entry windows to hand-cut white oak floors. At the heart of the home, the chef’s kitchen features premium Italian stainless steel appliances, a pot filler, soft-close cabinetry, and sleek granite countertops that extend throughout the house. Upstairs, relax in the custom-tiled shower or step onto the private balcony overlooking your serene backyard. Complete with a tankless water heater, room for a flourishing garden, and gorgeous front and back porches made for taking in the views, this special retreat offers uncompromised quality and complete tranquility. Four years in the making; a lifetime to enjoy!

2428 Glade Road, Asheboro

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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 .