Hillsborough Homes with Private Pool

Welcome to Hillsborough, North Carolina, a charming town nestled in the heart of Orange County. Rich in history and surrounded by breathtaking natural beauty, Hillsborough offers a unique blend of small-town charm and modern convenience. With its picturesque streets lined with historic homes, vibrant local shops, and a welcoming community spirit, Hillsborough is a hidden gem waiting to be discovered.

One of the standout features of this delightful town is the availability of homes with private pools. Imagine enjoying the warm North Carolina sun while lounging by your own serene oasis, perfect for relaxation and entertaining. These homes not only provide a refreshing escape during the summer months but also add a touch of luxury to your daily life. Whether you’re hosting summer barbecues, enjoying family gatherings, or simply unwinding after a long day, having a private pool transforms your home into a personal retreat.

Hillsborough is also known for its beautiful parks, scenic trails, and vibrant arts scene, making it an ideal location for families, retirees, and anyone looking to embrace a balanced lifestyle. The town's proximity to the bustling cities of Durham and Chapel Hill allows residents to enjoy the best of both worlds—peaceful living with easy access to urban amenities.

If you’re seeking a home that combines comfort, style, and the joy of having your own private pool, Hillsborough is the perfect place to start your search. Discover the beauty and tranquility of this wonderful town and make it your home 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 picturesque 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 gracious 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 private studio. The main level also features a dedicated office/additional bedroom, 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, an expansive 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 three-car 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 grounds include with 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 .