Grand Oak Estates Homes for Sale

Welcome to Grand Oak Estates, a picturesque subdivision nestled in the heart of Hillsborough, North Carolina. This charming community offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and everyone in between. With its tree-lined streets and beautifully landscaped yards, Grand Oak Estates is a place where neighbors become friends and memories are made.

The homes for sale in Grand Oak Estates are a testament to thoughtful design and quality craftsmanship. Ranging from spacious single-family homes to cozy cottages, each property boasts unique architectural details and contemporary finishes. Many residences feature open floor plans, gourmet kitchens, and expansive outdoor living spaces, perfect for entertaining or enjoying quiet evenings under the stars. With a variety of layouts and sizes, there’s a perfect fit for every lifestyle and budget.

Living in Grand Oak Estates means enjoying the best of both worlds. You’ll find yourself just minutes from the vibrant downtown Hillsborough, where charming shops, delightful eateries, and cultural attractions await. Nature enthusiasts will appreciate the nearby parks and trails, offering opportunities for hiking, biking, and exploring the scenic beauty of Orange County.

As a community that values connection and camaraderie, Grand Oak Estates often hosts neighborhood gatherings and events, fostering a strong sense of belonging. If you’re searching for a place to call home in a welcoming environment, look no further than Grand Oak Estates. Explore the available homes for sale today and discover the perfect backdrop for your next chapter!

Newest Grand Oak Estates Homes for Sale

$1,055,000

4 Beds ⋅ 4 Baths ⋅ 10179341 MLS ⋅ ACTIVE Status

Private Custom brick home in a beautiful Grand Oak Estate neighborhood. A short drive to downtown Hillsborough and Duke. Spacious wrap-around rocking chair front porch with rear screened porch. Home features beautiful reclaimed hardwood floors from an old whiskey distillery throughout the main floor, the railings to go upstairs were locally designed and milled. Tile floor in baths and utility room, granite countertop with custom cherry cabinets in kitchen. Design ideas based on a Carolina "T" Farmhouse using a brick finish. Main living area has a wood burning fireplace and the piano room utilizes a gas burning fireplace. Heated and cooled walk out basement (not included in the square footage) that also features a wood burning stove. Located on over 8 acres. Backyard receives great light for a garden. Surrounded by beautiful hardwood trees perfect for cutting shaded walking trails. Grand Oak Estates has a playground common area with a tennis court. Eno River Farms berry picking in an exciting adventure just down the road.

417 Grand Oak Dr, Hillsborough

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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 .