Pittsboro Homes with Private Pool

Welcome to Pittsboro, a charming town located in Chatham County, North Carolina, USA. Known for its picturesque landscapes, friendly community, and rich history, Pittsboro offers a perfect blend of small-town charm and modern amenities.

If you are looking for homes with private pools in Pittsboro, you are in luck! Many properties in this area feature private pools, allowing residents to enjoy the ultimate luxury and relaxation right in their backyard. Whether you are looking to host pool parties with friends and family or simply unwind after a long day, owning a home with a private pool in Pittsboro can elevate your lifestyle.

In addition to the allure of private pool homes, Pittsboro boasts a vibrant downtown area with unique shops, delicious dining options, and cultural attractions. Nature enthusiasts will appreciate the proximity to Jordan Lake and various parks, offering ample opportunities for outdoor recreation.

With its convenient location near major cities like Raleigh and Durham, Pittsboro provides residents with the perfect balance of tranquility and accessibility. Whether you are a first-time homebuyer, a growing family, or a retiree looking for a peaceful retreat, Pittsboro has something to offer everyone.

Don't miss the opportunity to explore the real estate options in Pittsboro and find your dream home with a private pool. Experience the best of Carolina living in this charming town that truly has it all.

Newest Pittsboro Homes with Private Pool

$1,160,000

4 Beds ⋅ 5 Baths ⋅ 10181215 MLS ⋅ ACTIVE Status

Updated custom home in Henry's Ridge with a first-floor primary suite, designated office, formal dining room and oversized sunroom on 1.6 private acres. Offering 4 bedrooms, 3 full baths, 2 half baths, and 4,847 square feet, this home is conveniently located just off Hwy. 64 near Jordan Lake with easy access to Pittsboro, Chapel Hill, Apex, and Cary. Extensively updated in 2021 with a remodeled kitchen featuring custom cabinetry, quartz countertops, oversized 3-inch island, expanded pantry with appliance nook, custom mudroom, enlarged laundry room with built-in dog wash, refinished hardwood floors, fresh interior paint, and custom built-ins.Outdoor living is designed for entertaining with an in-ground pool, pool house, exterior half bath, renovated decks, professionally landscaped yard, irrigation system, and commercial-grade landscape lighting. Additional features include a tankless water heater, reverse osmosis water filtration system, generator wiring, and an additional water heater with recirculation. The flat, tree-lined lot backs to approximately 80 acres that are unlikely to be developed, providing exceptional long-term privacy. Parking for approximately 12 vehicles.

242 Henrys Ridge Rd, Pittsboro

$469,990

2 Beds ⋅ 2 Baths ⋅ 10179669 MLS ⋅ ACTIVE Status

Welcome to the Inspiration at 160 Tantara Bend, where thoughtful design meets effortless living in this beautifully crafted paired Villa by David Weekley Homes. Designed for comfort and style, this single-level home offers the perfect blend of open-concept living, quality craftsmanship, and low-maintenance convenience. Soft gray and white designer finishes create a bright, timeless interior that feels both elegant and inviting. The gourmet kitchen serves as the heart of the home, featuring an oversized island, built-in stainless steel appliances, abundant cabinetry, and a sophisticated palette of soft gray and white finishes that make everyday living and entertaining a pleasure. The sun-filled family and dining areas flow seamlessly to the screened rear porch, creating the perfect setting to enjoy your morning coffee, unwind with a good book, or host family and friends while enjoying the outdoors in comfort. The spacious Owner's Retreat offers a private sanctuary complete with a spa-inspired bath featuring a zero-entry Super Shower, dual-bowl vanities, and a walk-in closet. Every detail has been thoughtfully selected to deliver the exceptional quality, comfort, and livability that define the Encore lifestyle. Encore at Chatham Park offers a resort-style, maintenance-free lifestyle with lawn care included and exclusive access to an impressive Amenity Center featuring a full-time Lifestyle Director, a 5,200-square-foot clubhouse, fitness center, tennis and pickleball courts, a putting green, resort-style pool and hot tub, meditation garden, gas fire pits, indoor and outdoor gathering spaces, and miles of scenic walking and biking trails. Residents also enjoy convenient access to nearby Mosaic, a vibrant mixed-use destination offering dining, entertainment, shopping, and year-round community events. Ideally located with easy access to US-64, US-15/501, I-540, and RDU Airport, this exceptional home places world-class healthcare, shopping, dining, recreation, and everyday conveniences just minutes away—giving you more time to enjoy the active, connected lifestyle you've been looking for.

160 Tantara Bnd, Pittsboro

$945,000

4 Beds ⋅ 3 Baths ⋅ 10178637 MLS ⋅ ACTIVE Status

Settle into summer with your own private oasis. Nestled on 2.67 picturesque acres, this exceptional custom-built home seamlessly blends sophisticated indoor craftsmanship with a breathtaking backyard retreat. Offering 3,270 square feet of thoughtfully designed living space, this masterfully crafted residence features 4 bedrooms, 3 bathrooms, and an abundance of natural light. Expansive windows throughout the home create a seamless connection to your own resort-style backyard, making the stunning landscape a part of your daily living. Property Highlights: The Ultimate Backyard Retreat: Spend sunny afternoons beside the sparkling in-ground pool, unwind in the cascading spa, or host unforgettable gatherings under the stars in total tranquility. Gourmet Kitchen & Living: A wonderful, chef-friendly kitchen flows effortlessly into the main living spaces, perfect for both effortless entertaining and quiet family nights. Private Primary Suite: A serene sanctuary designed for ultimate relaxation, completely separated from the hustle and bustle of the home. Bonus 3rd Floor Living: A massive third-floor bonus room offers endless flexibility—ideal for a home theater, executive office, gym, or game room. Modern Efficiency & Craftsmanship: Enjoy the peace of mind that comes with custom architectural details paired with modern, energy-efficient systems. This remarkable Pittsboro property offers a rare combination of custom luxury, peaceful privacy, and resort-inspired indoor-outdoor living. Don't miss the opportunity to experience your own private slice of paradise. The house is not visible from the road. When turning left onto Silk Hope Gum Spring Rd, the house will be on the right hand side

2946 Silk Hope Gum Spring Rd, Pittsboro

$799,900

4 Beds ⋅ 4 Baths ⋅ 10163391 MLS ⋅ ACTIVE Status

Every day is a vacation at this marvelous 4 bedroom 3 1/2 bath Chatham County home! Let's start with the outside: A 24' diameter pool, hot and cold water shower with changing room plus a water slide with custom surround decking and clubhouse anchors the backyard, a wooded setting perfect for big gatherings or just relaxing with the family. There's also a deck and patio near the grill, and all the top boards on the decks are composite for low maintenance. There's a trail with a bridge around the over 2 acre lot for walking or riding the mountain bikes. There's plenty of room to park other toys too - RV, Boat, Trailers, you name it! Plus 2 electric wired storage buildings with security for your tools, hobbies or crafts. Heading inside, first is the big front porch perfect for a swing and rocking chairs. The Living Room features a gas log fireplace and in-wall surround speakers. And for a quiet afternoon read, the sitting room is ideal. A formal Dining Room fronts the renovated kitchen with new dishwasher and cooktop, and be sure to peer into the custom pantry! A breakfast nook and counter are great for informal meals or take it out to the sunroom for dining with a killer view. A large laundry room is off the hallway to the Primary Bedroom- and what a room it is - high ceilings, gas log fireplace, custom closets and an amazing view of the tree tops. Then there's the spa-like bathroom featuring two sinks, heated towel bar and a huge walk-in tiled shower with yet another breathaking view! Another spot for year round vacations! Upstairs are 3 bedrooms and 2 bathrooms, one en-suite. Perfect for the kids, guests and/or home office(s). The ground floor, accessed from stairs off the Laundry Room hall or 2 exterior doors, houses a 28 x 30 Entertainment Room with pool table, fridge, bar, A/V shelf, TV mount and surround sound. It could easily be converted to a one or two car garage as this was the original design. Also at this level is a one car garage with tons of customized storage shelving, plus an Exercise Room and a workshop with a huge safe for all your valuables!. All of this just 1/2 mile from the Haw River and Bynum, 10 minutes to Pittsboro, 25 minutes to Chapel Hill and 40 minutes to the RDU Airport! Come visit this one to see your everyday vacation getaway!

89 Lauren Ct, Pittsboro

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 10159461 MLS ⋅ ACTIVE Status

The pool is OPEN and this stunner is ready for Summer and outdoor entertaining! A private retreat on over 2 acres tucked away on a cul-de-sac in The Hamptons complete with covered outdoor grilling and dining area, a beautiful pool, outdoor stone fireplace, screened porch and owner's suite and guest bedrooms on the first floor with 2 additional bedrooms upstairs with a bonus. The perfect location that is convenient to Chapel Hill, Durham, Cary, Apex & RDU Int'l. W/D, Refrg, Comm Freezer in garage and garage shelving convey

417 Laurel Knoll Dr, Pittsboro

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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 .