Hillsborough Homes with Fenced Pool

Welcome to Hillsborough, North Carolina—a picturesque town that perfectly marries small-town charm with modern convenience. Nestled in the heart of Orange County, Hillsborough is rich in history, boasting beautifully preserved architecture and a vibrant community spirit. With its scenic landscapes, historic sites, and a welcoming atmosphere, it’s no wonder that Hillsborough has become a sought-after destination for families, retirees, and anyone looking to enjoy a tranquil lifestyle.

One of the standout features of homes in Hillsborough is the availability of properties with fenced pools. Imagine stepping into your backyard oasis, where a sparkling pool awaits you, surrounded by a secure fence that provides peace of mind for families with children or pets. These homes offer the perfect blend of relaxation and recreation, allowing you to host summer barbecues, enjoy lazy afternoons by the pool, or simply unwind after a long day.

The community is also known for its lush parks, excellent schools, and a variety of local shops and restaurants that cater to every taste. Whether you’re strolling along the Eno River or exploring the delightful downtown area, you’ll find that Hillsborough is more than just a place to live; it’s a place to thrive.

If you’re searching for a home that combines comfort, security, and leisure, consider a Hillsborough property with a fenced pool. Not only will you enjoy the luxury of your own private retreat, but you’ll also be part of a vibrant community that welcomes you with open arms. Come discover the charm of Hillsborough, where your dream home awaits!

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 .