Pittsboro Homes with Association Pool

Welcome to Pittsboro, a charming town nestled in the heart of Chatham County, North Carolina. Known for its picturesque landscapes, vibrant community, and rich history, Pittsboro offers a unique blend of small-town charm and modern amenities.

As you explore Pittsboro, you'll discover a thriving arts scene, with local galleries, boutiques, and artisanal shops lining the historic streets. The town is also home to a variety of dining options, ranging from cozy cafes to upscale restaurants, serving up delicious farm-to-table cuisine.

For outdoor enthusiasts, Pittsboro boasts an abundance of recreational opportunities, including hiking trails, parks, and nearby Jordan Lake for water activities. The town's close-knit community comes together for events like farmers' markets, festivals, and live music performances, creating a warm and welcoming atmosphere for residents and visitors alike.

If you're in the market for a home in Pittsboro with access to an association pool, you're in luck. Many properties in the area offer this sought-after amenity, providing a perfect place to relax and unwind during the warm summer months. Whether you're looking for a cozy cottage, a spacious family home, or a luxury estate, Pittsboro has a range of real estate options to suit your lifestyle.

Come experience the beauty and charm of Pittsboro – a place where small-town living meets modern convenience, creating a truly special place to call home.

Newest Pittsboro Homes with Association Pool

$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

$578,300

2 Beds ⋅ 2 Baths ⋅ 10178970 MLS ⋅ ACTIVE Status

Welcome to the Sweetfern by David Weekley Homes, an exceptional opportunity to create your dream home in the award-winning Encore at Chatham Park. Construction has not yet begun, giving you a limited-time chance to personalize your home with selections from our professional Design Studio. This thoughtfully designed floor plan already includes an impressive collection of upgraded features, including a gourmet kitchen with a gas cooktop, elegant French doors leading to the private study, a spacious roll-in shower in the Owner's Bath, a tray ceiling in the luxurious Owner's Retreat, expansive 7-foot sliding glass doors opening to the covered rear porch, and a utility sink with countertop in the laundry room. For a limited time, buyers can also take advantage of an outstanding Design Studio incentive—receive $10,000 toward your personalized selections when you invest up to $20,000 in Design Studio upgrades. This is the perfect opportunity to create a home that reflects your unique style while enjoying significant savings. The opportunity to personalize this home is available only through July 19, after which construction selections will be finalized. Don't miss your chance to build a home that's uniquely yours while taking advantage of this exceptional incentive. Encore at Chatham Park offers a maintenance-free, resort-inspired lifestyle with lawn care included and exclusive access to a 5,200-square-foot clubhouse, fitness center, pickleball and tennis courts, resort-style pool and spa, putting green, walking trails, and a full-time Lifestyle Director who keeps the community active and connected. The model home is located at 175 Prospect Place and open Monday through Saturday from 10:00 am -6:00 pm and Sunday 12:00 pm - 6:00 pm. This home has not started construction, however the structural details are already firm, and cannot be changed.

87 Englehart Ct, 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

$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

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 10161024 MLS ⋅ ACTIVE Status

A rare opportunity awaits in the exclusive Estates at Chapel Ridge. This distinguished Prewitt-Douglas custom home sits on nearly an acre -- one of the last remaining lots in this coveted enclave. Spanning over 3,500 square feet, the residence showcases high-end finishes throughout and a desirable main-level primary suite complete with dual walk-in closets. Four bedrooms and 3.5 baths offer ample space for comfortable everyday living and effortless entertaining. Residents enjoy access to Chapel Ridge's full suite of community amenities, providing year-round recreation for the entire family. Exceptional craftsmanship, a premier lot, and an unmatched location -- opportunities like this are few and far between.

36 Rosefield Ct, 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

$1,495,000

4 Beds ⋅ 4 Baths ⋅ 10160197 MLS ⋅ ACTIVE Status

Wow! This gorgeous 4070 sf Prewitt-Douglas Custom home located in Chapel Ridge Estates sits on a rare one and one half acre lot. Featuring 4 bedrooms, 3.5 bathrooms, a fabulous hearth room and 3 car garage, this one will be truly stunning.

60 Willow Creek Ct, 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 .