Hillsborough Homes with Private Pool

Welcome to Hillsborough, North Carolina—a charming town nestled in the heart of Orange County, where history meets modern living. With its picturesque landscapes, vibrant community, and rich cultural heritage, Hillsborough offers an idyllic setting for those seeking a tranquil yet engaging lifestyle.

As you explore this delightful town, you’ll discover a unique blend of historic architecture and contemporary amenities, making it an attractive option for families, professionals, and retirees alike. The downtown area boasts quaint boutiques, delightful eateries, and local art galleries, all set against a backdrop of lush green parks and scenic trails. Hillsborough is also known for its commitment to preserving its history, with landmarks like the historic Burwell School and the charming Hillsborough Riverwalk providing a glimpse into the past.

For those seeking the ultimate in relaxation and leisure, Hillsborough offers a variety of homes with private pools. Imagine stepping into your backyard oasis on a warm summer day, where you can unwind by the poolside, host barbecues with friends, or enjoy a refreshing swim at your leisure. These homes not only provide a personal retreat but also enhance your lifestyle, allowing for year-round enjoyment of North Carolina’s beautiful climate.

Whether you’re drawn to the town’s rich history, the welcoming community spirit, or the allure of a home with a private pool, Hillsborough is a place where you can truly feel at home. Discover the perfect property that suits your needs and embrace the Hillsborough lifestyle today!

Newest Hillsborough Homes with Private Pool

$2,179,000

5 Beds ⋅ 6 Baths ⋅ 10175110 MLS ⋅ ACTIVE Status

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

$1,175,000

5 Beds ⋅ 5 Baths ⋅ 10154536 MLS ⋅ ACTIVE Status

Beat the heat and enjoy this home's inground pool!! Set on 10 acres in desirable Hillsborough, this exceptional 4,444sf estate offers a rare blend of resort-style living, privacy, and versatility. With 2 acres of cleared and fenced pasture, this property is perfectly suited for equestrian use. A beautiful wraparound front porch, perfect for a swing and numerous rocking chairs, welcomes you and sets the tone for the home. The first-floor primary suite is a true private retreat, showcasing views of the pool, a spacious walk-in closet, a luxurious bath, a sitting room, and an additional flex space perfect for a nursery, fitness area, or office. The main level also features an additional bedroom with ensuite, formal living and dining rooms, and a light-filled sunroom, providing an effortless flow for both everyday living and entertaining. The kitchen is beautiful with granite countertops, a huge pantry, a dedicated coffee bar and it opens into a large breakfast nook filled with natural light and overlooking the pool. Upstairs, two generously sized secondary bedrooms and a full bath provide comfortable accommodations, while the finished space above the garage offers exceptional flexibility. Complete with two additional rooms and a full bath, this area is ideal for an in-law suite/guest suite, game room, media space, or private retreat. The home also includes a 3-car attached garage with epoxy floors. The grounds include a heated and cooled detached workshop, multiple outbuildings, and a resort-style pool complete with a slide--creating an ideal backdrop for both relaxation and recreation. The pool also has a new liner. Roof is 2018. Crawlspace was recently encapsulated. Despite its peaceful, estate-like setting, the home offers remarkable convenience--located just 15 minutes from downtown Hillsborough, approximately 20 minutes to downtown Durham, and within 30 minutes of RTP and RDU. This is a rare opportunity to enjoy luxury, land, and lifestyle--without compromise.

4000 Woodland Park 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 .