Pittsboro Homes with Fenced Pool

Pittsboro Homes with Fenced Pool

Welcome to Pittsboro, a charming town located in Chatham County, North Carolina, USA. Known for its picturesque landscapes, historic downtown, and vibrant community, Pittsboro offers a unique blend of small-town charm and modern amenities.

If you're in search of homes with a fenced pool, Pittsboro has plenty to offer. Whether you're looking for a cozy cottage or a spacious family home, you'll find options that feature the perfect combination of comfort and luxury. Imagine spending your summer days lounging by the pool, hosting barbecues with friends and family, and creating lasting memories in your own backyard oasis.

Living in a home with a fenced pool in Pittsboro allows you to enjoy the outdoors and stay active without ever leaving the comfort of your property. It's the perfect setting for relaxation, entertainment, and creating a private retreat where you can unwind after a long day.

With its friendly community, beautiful surroundings, and homes with fenced pools, Pittsboro is a place where you can truly live the good life. Explore the real estate options available in this charming town and find your perfect home where you can enjoy the best of indoor and outdoor living.

Newest Pittsboro Homes with Fenced 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
$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
$469,590
2 Beds ⋅ 2 Baths ⋅ 10178301 MLS ⋅ ACTIVE Status
Welcome to 142 Tantara Bend, where thoughtful design meets effortless living in this beautifully crafted paired Ambition 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. The gourmet kitchen is the heart of the home, featuring an oversized island, built-in stainless steel appliances, abundant cabinetry, and designer 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 space to enjoy your morning coffee, relax with a good book, or entertain guests while enjoying the outdoors in comfort. The spacious Owner's Retreat provides a private sanctuary with a spa-inspired bath featuring a zero-entry Super Shower, dual vanities, and an expansive 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, 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 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 lifestyle you've been looking for. The model home is located at 175 Prospect Place and open Monday through Saturday, 10:00 am - 6:00 pm, and Sunday 12:00 pm - 6:00 pm.

142 Tantara Bnd, Pittsboro
$3,195,000
5 Beds ⋅ 6 Baths ⋅ 10176685 MLS ⋅ ACTIVE Status
Luxury, privacy, and timeless elegance come together in this extraordinary custom-built estate on 2 private acres just minutes from Jordan Lake. Designed to impress at every turn, this one-of-a-kind home is filled with natural light from stunning oversized windows that showcase every beautiful space. Offering 5 spacious bedrooms and 5.5 bathrooms, including a luxurious primary suite and private mother-in-law suite on the main level, this home was thoughtfully designed for both everyday living and unforgettable entertaining. The chef's kitchen, complete with a butler's kitchen, flows effortlessly into the open living spaces, while the upstairs loft, oversized bonus room, and private balcony provide endless room to relax, work, or play. Step outside to your own resort-style backyard featuring a sparkling pool, peaceful surroundings, and the privacy you've been searching for. Every detail has been carefully crafted to create a home that feels like a private retreat while keeping you just minutes from Jordan Lake and everyday conveniences. This is more than a place to live. It is the kind of home you'll never outgrow, never want to leave, and never forget.

196 Mountaintop Cir, Pittsboro
$965,000
4 Beds ⋅ 4 Baths ⋅ 10084591 MLS ⋅ ACTIVE Status
Beautiful custom home in the highly desirable Chapel Ridge neighborhood. The primary suite and guest bedroom are on the first floor with two additional bedrooms upstairs. This wonderful open floor plan gives you plenty of room to entertain. Walking distance to the many community amenities including the pool, golf and tennis.

829 Chapel Ridge Dr, Pittsboro
$1,285,000
4 Beds ⋅ 4 Baths ⋅ 10161265 MLS ⋅ ACTIVE Status
Exceptional Prewitt-Douglas custom home situated on a quiet cul-de-sac in the prestigious Chapel Ridge community. This 4 bedroom, 3.5 bath residence boasts an open, expansive floor plan designed for effortless entertaining -- both indoors and out. Thoughtfully crafted with generous living spaces and outstanding attention to detail throughout. Residents enjoy access to world-class community amenities including golf, tennis, and a resort-style pool. A rare opportunity to own a distinguished home in one of the area's most coveted neighborhoods -- this one will not last.

64 Mist Wood Ct, Pittsboro
$1,230,000
4 Beds ⋅ 9 Baths ⋅ 10159657 MLS ⋅ ACTIVE Status
Exceptional Prewitt-Douglas custom home overlooking Chapel Ridge golf course. This 3,365 SF residence offers 4 bedrooms, 4.5 baths, a 2-car garage, and a dedicated golf viewing room ideal for entertaining. Quality craftsmanship throughout with sweeping golf course views. A rare find in a premier setting -this one won't last long.

227 Deep Crk, Pittsboro
$955,000
4 Beds ⋅ 4 Baths ⋅ 10132755 MLS ⋅ ACTIVE Status
Exceptional custom home in the sought-after Chapel Ridge community. This thoughtfully designed 4 bedroom, 4 bath residence offers an ideal layout with a main-level primary suite and secondary bedroom, perfect for single-level convenience. The open-concept living area flows seamlessly into a beautifully appointed kitchen, creating an inviting space for everyday living and entertaining. Upstairs, two additional bedrooms each feature private en suite baths, while a bonus room and flexible flex space provide endless possibilities for work, play, or relaxation. All of this set within Chapel Ridge -- a premier community offering resort-style amenities just moments from your door. A rare combination of thoughtful design, quality craftsmanship, and an unmatched lifestyle.

191 High Ridge Ln, Pittsboro
Start Your Search

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 .