Hillsborough Homes with Private Pool

Hillsborough Homes with Private Pool

Welcome to Hillsborough, North Carolina—a hidden gem nestled in the heart of Orange County. Rich in history and charm, this picturesque town boasts a vibrant community, scenic landscapes, and a welcoming atmosphere that makes it a perfect place to call home. With its quaint downtown area, local boutiques, and delightful eateries, Hillsborough offers a unique blend of small-town charm and modern conveniences.

One of the standout features of Hillsborough is its commitment to preserving its historical roots while embracing growth and development. Residents enjoy access to beautiful parks, walking trails, and the serene Eno River, providing ample opportunities for outdoor activities and relaxation. The town's rich cultural scene, highlighted by art galleries and annual festivals, ensures there's always something happening.

For those seeking a slice of paradise, Hillsborough offers an array of homes with private pools, allowing you to enjoy the warm North Carolina sun in the comfort of your own backyard. Imagine hosting summer barbecues, lounging by your poolside oasis, or enjoying a peaceful evening swim under the stars. These properties not only provide a refreshing escape but also enhance your lifestyle, making every day feel like a vacation.

Whether you’re a first-time homebuyer, looking to upgrade, or searching for an investment property, Hillsborough’s real estate market has something for everyone. Discover the joys of living in this charming town, where community spirit thrives, and your dream home with a private pool awaits. Embrace the Hillsborough lifestyle—where history meets modern living!

Newest Hillsborough Homes with Private 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 .