Hillsborough Homes with Outdoor Pool

Welcome to Hillsborough, North Carolina—a charming town steeped in history and bursting with Southern hospitality. Nestled in the picturesque Orange County, Hillsborough is a hidden gem that offers a perfect blend of small-town charm and modern conveniences. With its vibrant arts scene, historic architecture, and lush landscapes, this community is ideal for families, retirees, and anyone seeking a peaceful yet engaging lifestyle.

One of the most enticing features of Hillsborough is the availability of stunning homes with outdoor pools. Picture yourself lounging by your private oasis, soaking up the warm North Carolina sun, or hosting delightful summer gatherings with friends and family. These homes are not just residences; they are retreats designed for relaxation and enjoyment. With spacious backyards and beautifully landscaped surroundings, each property offers a unique space to create lasting memories.

Hillsborough is also known for its strong sense of community. Enjoy leisurely strolls along the Eno River, explore the local farmer’s market, or participate in vibrant community events that celebrate the area’s rich heritage. The nearby parks and recreational areas provide ample opportunities for outdoor activities, making it easy to embrace an active lifestyle.

Whether you’re drawn to the historic charm of downtown, the natural beauty of the surrounding landscape, or the luxury of a home with an outdoor pool, Hillsborough is a place where you can truly feel at home. Discover your dream property today and experience the best that this enchanting town has to offer!

Newest Hillsborough Homes with Outdoor 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

$269,500

2 Beds ⋅ 2 Baths ⋅ 10148811 MLS ⋅ ACTIVE Status

Come home to this delighful 2 bedroom townhome minutes from schools, shopping, and downtown Hillsborough. Close to both I-40 and I-85 for easy commutes. This home was recently updated with new carpet in living room and new dishwasher, garbage disposal and sink faucet. The refrigerator, range & microwave were new in 2022. The neighborhood features a pool and has a newly renovated clubhouse and fitness center. Relax on your private patio and imagine what you want to plant in the raised bed planters. This home comes with a 1 car garage for either parking your car...or overflow storage or a little of both! Welcome home!

1873 Birmingham Dr, Hillsborough

$490,190

5 Beds ⋅ 3 Baths ⋅ 10141827 MLS ⋅ ACTIVE Status

Welcome to 208 Lightfoot Lane at Collins Ridge in historic, and picturesque town of Hillsborough, NC! The Hayden features 5 bedrooms, 3 bathrooms, 2,511 sq. ft. of living space, and a 2-car garage. Upon entering the home, you'll be greeted by an inviting foyer passing by the flex room, then led into the center of the home. This open-concept space features a functional kitchen overlooking the living room, a breakfast area, a guest bedroom and a full bathroom in the back left of the home. The kitchen is equipped with a corner walk-in pantry, quartz countertops, stainless steel appliances, kitchen island, and a breakfast area. From the breakfast area you can step out onto the back patio, perfect for entertaining guests or relaxing after a long day. The second floor hosts the spacious primary bedroom and primary bathroom boasting two walk-in closets, a walk-in shower, dual vanity, and separate water closet for ultimate privacy. The additional three bedrooms share a third full bathroom the upstairs loft space is perfect for family entertainment, work out area, or a reading space. The laundry room completes the second floor. With its luxurious design and ample space, the Hayden is the perfect place to call home. Do not miss this opportunity to make the Hayden yours! *Pictures are for representational purposes only*

208 Lightfoot 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 .