Hillsborough Homes with Outdoor Pool

Hillsborough Homes with Outdoor Pool

Welcome to Hillsborough, North Carolina, a charming town nestled in the heart of Orange County. With its rich history, vibrant community, and picturesque landscapes, Hillsborough offers a unique blend of small-town charm and modern amenities. Just a short drive from the bustling cities of Durham and Chapel Hill, this delightful town is perfect for those seeking a serene lifestyle without sacrificing convenience.

Hillsborough is renowned for its beautifully preserved historic district, where you can stroll along tree-lined streets and admire stunning antebellum architecture. The town's vibrant arts scene, coupled with an array of local shops and eateries, provides a welcoming atmosphere for residents and visitors alike. Nature enthusiasts will appreciate the abundance of parks and trails, including the scenic Eno River State Park, ideal for hiking, fishing, and picnicking.

For those seeking a home that enhances their outdoor living experience, Hillsborough boasts a selection of properties featuring stunning outdoor pools. Imagine lounging by your private pool on warm summer days, hosting barbecues, or enjoying a peaceful evening under the stars. These homes are designed for both relaxation and entertainment, making them perfect for families and individuals who enjoy an active lifestyle.

With its beautiful surroundings, rich culture, and a strong sense of community, Hillsborough is an ideal place to call home. Explore our listings today and discover the perfect property with an outdoor pool that suits your lifestyle in this enchanting North Carolina town!

Newest Hillsborough Homes with Outdoor Pool

$2,179,000
5 Beds ⋅ 6 Baths ⋅ 10175110 MLS ⋅ ACTIVE Status
**SEPTEMBER OPEN HOUSE 2-4 PM EVERY SUNDAY*** Tucked away on 10 private acres in Hillsborough's coveted Fox Hill Farm, this exceptional estate offers a rare opportunity to enjoy the privacy of country living with a combination of features rarely found in one property, all just minutes from historic downtown Hillsborough, Durham, Chapel Hill, Duke University, RTP, and RDU Airport. Thoughtfully designed for both comfort and flexibility, nearly all bedrooms and primary living spaces are located on the main level. Walls of custom windows fill the home with natural light and frame picturesque views of the surrounding landscape, while the renovated kitchen, inviting sunroom, and expansive Trex deck create seamless indoor-outdoor living for both quiet moments and effortless entertaining. The private primary suite serves as a peaceful retreat, offering a spacious sitting area, dual walk-in closets, a spa-inspired bath, and a dedicated office with French doors. Step outside and discover your own private retreat. Relax beside the newly lined saltwater pool, unwind beneath the covered gazebo, enjoy the sand volleyball court, or spend a peaceful afternoon at the community's fully stocked fishing pond. The 10-acre corner homesite also allows up to four horses, while Fox Hill Farm's scenic riding and walking trails invite you to experience the beauty of the outdoors just beyond your doorstep. The finished lower level is designed for entertaining and relaxation, featuring a stadium-style theater, a private salon, and a pool table that conveys. Upstairs, a spacious bonus room, full fitness center, and abundant storage provide exceptional flexibility for wellness, creativity, work, or recreation. One of Hillsborough's hidden gems, Fox Hill Farm offers a peaceful, picturesque setting with scenic riding and walking trails, while remaining just minutes from award-winning dining, boutique shopping, farmers markets, festivals, and the scenic Eno River. Opportunities to own an estate offering this rare combination of acreage, privacy, exceptional amenities, and Triangle convenience are few and far between. Welcome to 2601 Littleleaf Lane.

2601 Littleleaf Ln, 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 .