Hillsborough Homes with Fenced 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 delightful blend of small-town charm and modern conveniences. Known for its beautifully preserved historic district, residents and visitors alike can stroll along tree-lined streets, explore quaint shops, and savor delicious local cuisine at inviting cafes and restaurants.

One of the standout features of homes in Hillsborough is the growing trend of properties with fenced pools. Imagine coming home to your own private oasis, where you can unwind and rejuvenate in the comfort of your backyard. These homes not only provide a refreshing escape during the warm North Carolina summers but also offer a safe and secure environment for family and friends to enjoy. Fenced pools are perfect for families with children or pets, allowing everyone to enjoy the water while giving parents peace of mind.

In Hillsborough, you can find a variety of architectural styles, from historic homes that tell the tales of yesteryear to modern designs that cater to contemporary lifestyles. Each property with a fenced pool is a unique gem, providing an inviting space for entertaining guests or simply relaxing after a long day.

With its friendly atmosphere, excellent schools, and abundant recreational opportunities, Hillsborough is the perfect place to call home. Discover the joy of living in a community that values both heritage and progress, all while enjoying the luxury of a home with a fenced pool. Come and experience the beauty of Hillsborough today!

Newest Hillsborough Homes with Fenced Pool

$1,525,000

4 Beds ⋅ 3 Baths ⋅ 10177956 MLS ⋅ ACTIVE Status

Set on 20+ acres minutes from Downtown Hillsborough, this thoughtfully designed equestrian and homestead retreat offers fenced pastures, riding ring, all-weather arena, run-in shelter, and 4 stall barn with heated tack room, feed room, hay loft, and new roof. Outdoor living includes a heated saltwater pool, hot tub, outdoor shower, firepit, pasture views, heated greenhouse, gardens, vineyard, and custom chicken coop. The farmhouse lives beautifully with hardwoods throughout, generous everyday living spaces, gas fireplace, sunroom, bonus room, and main level office with built-ins. The well-appointed kitchen features 2 copper sinks, a Sub-Zero fridge/freezer, new GE Café stainless-steel appliances, 3 ovens, and a drawer-style dishwasher. Fiber internet, water purification system, solar panels, EV charger, backup generator, and new metal roof.

4911 Parc Jardin Dr, Hillsborough

$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

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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 .