Pittsboro Homes under $500,000

Pittsboro Homes under $500,000

Welcome to Pittsboro, North Carolina—a charming town that beautifully blends small-town warmth with a rich tapestry of history and modern living. Nestled in Chatham County, Pittsboro is a hidden gem that offers residents a serene lifestyle surrounded by natural beauty and a tight-knit community spirit. With its quaint downtown area, you’ll find delightful shops, cozy cafes, and local eateries that showcase the best of Southern hospitality.

Pittsboro is not just about its picturesque streets and friendly faces; it’s also a place where you can find your dream home without breaking the bank. With a range of homes available under $500,000, this vibrant community is perfect for first-time buyers, families, and retirees alike. Whether you’re searching for a charming cottage, a spacious family home, or a modern townhouse, Pittsboro has diverse options that cater to various lifestyles and preferences.

The town is conveniently located near major highways, making commuting to the bustling cities of Chapel Hill and Raleigh a breeze. Plus, with an array of parks, recreational activities, and nearby lakes, outdoor enthusiasts will find plenty of opportunities to explore and enjoy the great outdoors.

Living in Pittsboro means immersing yourself in a community rich in culture and tradition while enjoying the comforts of modern living. With affordable housing options and a welcoming atmosphere, it’s no wonder that Pittsboro is becoming one of North Carolina’s most sought-after places to call home. Discover your perfect Pittsboro home today and experience all that this enchanting town has to offer!

Newest Pittsboro Homes under $500,000

132 Penny Ln, Pittsboro
$260,000
3 Beds ⋅ 1 Baths ⋅ LP771437 MLS ⋅ ACTIVE Status
Discover the charm of country living with the convenience of a desirable Chatham County location! Situated on approximately 0.96 acres, this single-story home offers three bedrooms, one full bathroom, and approximately 800 square feet of living space.Newer HVAC, new well and well pump. The property provides an opportunity to enjoy a peaceful rural setting with room for outdoor activities, gardening, or creating your own backyard retreat. Whether you’re looking for a primary residence, investment property, or a home to make your own, this property offers possibilities in an attractive location.Location is a standout feature! Conveniently situated between Pittsboro and Chapel Hill, the property offers access to the shopping, dining, and amenities of both communities. Enjoy proximity to Jordan Lake, Fearrington Village, and the University of North Carolina at Chapel Hill, while appreciating the quieter atmosphere of Chatham County.With nearly an acre of land and a location convenient to some of the area’s most desirable destinations, 132 Penny Lane presents an opportunity to enjoy country living without sacrificing accessibility.

132 Penny Ln, Pittsboro
139 Prestonwood Dr, Pittsboro
$325,000
3 Beds ⋅ 2 Baths ⋅ 10200083 MLS ⋅ ACTIVE Status
Welcome home to this 3-bedroom, 2-bathroom single-family residence in Forest Creek, Pittsboro. Set on a generous lot of almost one acre, this property offers substantial outdoor space and privacy for those seeking room to grow. The well-proportioned home provides comfortable living quarters with practical design. The expansive grounds present endless possibilities for landscaping, recreation, or future development according to your vision. Close proximity to schools and shopping. This is an excellent opportunity to own a solid residential property with ample land in an established community.

139 Prestonwood Dr, Pittsboro
137 Evergreen Dr, Pittsboro
$449,000
3 Beds ⋅ 3 Baths ⋅ 10199504 MLS ⋅ ACTIVE Status
Freshly renovated and full of charm in the heart of Pittsboro! Situated on just over half an acre on a culdesac peaceful road. This 1,661-square-foot home is completely renovated it offers 3 bedrooms, 2.5 baths, and inviting curb appeal with a metal roof and easy-care landscaping. The main-floor primary suite features a beautifully updated bath with a walk-in shower. Upstairs, two additional bedrooms share a newly renovated, light-filled full bath. The ample kitchen shines with new maple cabinetry, quartz countertops, all new appliances. LVP flooring throughout adds style and everyday practicality. Rocking chair front porch. A spacious back deck overlooks the generous backyard, creating a welcoming spot to relax or entertain. New Windows and Blinds thru-out. Enjoy a small-subdivision feel with convenient access to Pittsboro's shopping, dining, parks, and in-town activities, plus easy connections to Highways 15/501, 87, 64, and 902.

137 Evergreen Dr, Pittsboro
125 Prospect Pl, Pittsboro
$499,900
2 Beds ⋅ 2 Baths ⋅ 10199016 MLS ⋅ ACTIVE Status
Stunning 2 bed 2 bath ranch style residence located in the highly desirable Encore at Chatham Park 55+ community. Open floor plan with luxury vinyl planking floors flowing throughout the home. Spacious family room. Bright & open eat-in kitchen offers massive center island, quartz countertops, designer tile backsplash, stainless steel appliances & generous pantry. Separate dining area includes built-in cabinetry. Large primary suite has tray ceiling, quartz top dual vanities, oversized zero entry tile shower & walk in closet. Fantastic sunroom/4 season room with electric fireplace and beautiful pond views. 2 car garage. Low maintenance living & resort style amenities with the clubhouse directly across the street offering a sparkling pool, state of the art fitness center, pickle ball/tennis courts, clubs/social events, parks and greenways.

125 Prospect Pl, Pittsboro
189 Tantara Bnd, Pittsboro
$465,920
2 Beds ⋅ 2 Baths ⋅ 10198640 MLS ⋅ ACTIVE Status
Rare Opportunity in Encore at Chatham Park! One of the few remaining Inspiration Villas, this beautifully designed quick move-in home offers effortless, low-maintenance living in Pittsboro, NC. Designed for a 55+ lifestyle, the open, light-filled layout features a spacious kitchen that flows seamlessly into the main living and dining areas. The main-level Owner's Suite offers a relaxing retreat with a spa-inspired bath and ample closet space. A secondary bedroom and enclosed flex study provide versatility for guests, hobbies, or working from home. Enjoy thoughtful design, everyday comfort, and more time for what matters most. Don't wait—discover the Inspiration lifestyle at Encore while this limited opportunity remains!

189 Tantara Bnd, Pittsboro
308 Baneberry Close, Pittsboro
$410,000
2 Beds ⋅ 3 Baths ⋅ 10198519 MLS ⋅ ACTIVE Status
OVER $120K IN UPGRADES! Beautifully Renovated End-Unit Townhome in Sought-After Fearrington Village in Pittsboro, NC! Welcome home to this beautifully updated 2-bedroom, 2-bath end-unit townhome offering 1,968 square feet of spacious living and over $120,000 in improvements! Combining modern finishes, extensive renovations, and inviting indoor-outdoor living, this exceptional property offers comfort, style, and peace of mind. The updated kitchen shines with new cabinetry, quartz countertops, and new appliances. Both bathrooms have been refreshed with new antimicrobial showers, cultured marble countertops, and new tile flooring. New carpeting throughout, fresh paint, updated lighting, and smooth ceilings create a clean, modern feel throughout the home. Beyond the cosmetic enhancements, major improvements include new electrical wiring, new plumbing, and an encapsulated crawlspace. The end-unit location offers added privacy, while the enclosed sunroom provides versatile additional living space to enjoy year-round. Step out onto the deck to relax or enjoy your morning coffee. Parking is convenient with an oversized one-car garage, an additional parking space outside the garage, and an extra parking space on the premises. With generous square footage, extensive updates, and desirable indoor-outdoor living spaces, this move-in-ready townhome is an outstanding opportunity in a sought-after Fearrington neighborhood. Extensive upgrades, stylish finishes, and spacious living . . . all in one exceptional home! Don't miss this opportunity to make it yours.

308 Baneberry Close, Pittsboro
217 Tantara Bend Bnd, Pittsboro
$474,820
2 Beds ⋅ 2 Baths ⋅ 10197958 MLS ⋅ ACTIVE Status
Experience refined, low-maintenance living in this beautifully designed paired Inspiration villa by David Weekley Homes, located in the sought-after 55+ community of Encore at Chatham Park. Thoughtfully crafted for comfort and everyday ease, this single-level home blends open-concept living with elevated design details. At the heart of the home, the chef-inspired kitchen impresses with a large gathering island, built-in stainless steel appliances, abundant cabinetry, and sleek finishes--perfect for both casual mornings and effortless entertaining. The adjoining living and dining spaces are filled with natural light and extend seamlessly to a covered rear porch, creating a private outdoor retreat ideal for relaxing or hosting guests. The spacious Owner's Retreat offers a peaceful escape, complete with a spa-like bath featuring a zero-entry Super Shower, dual bowl vanity, and a generous walk-in closet designed for optimal organization. Secondary spaces provide flexibility for guests, hobbies, or a home office, ensuring the home adapts to your lifestyle. Enjoy the ease of maintenance-free living with lawn care included, along with access to Encore's exceptional resort-style amenities. Residents enjoy a 5,200 sq ft clubhouse, fitness center, tennis and pickleball courts, resort-style pool and spa, putting green, meditation garden, gas firepits, and a full calendar of events curated by an on-site Lifestyle Director. Scenic walking and biking trails connect you to the vibrant Mosaic district for dining, entertainment, and everyday conveniences. Ideally positioned with quick access to US-64, 15-501, I-540, and RDU, this home offers the perfect blend of tranquility and accessibility--placing world-class healthcare, shopping, dining, and travel just minutes away.

217 Tantara Bend Bnd, Pittsboro
179 Tantara Bnd, Pittsboro
$499,570
2 Beds ⋅ 2 Baths ⋅ 10197876 MLS ⋅ ACTIVE Status
One of only Two Clarities remaining in Encore. Discover the perfect blend of comfort, style, and thoughtful design in the beautiful Clarity floorplan by David Weekley Homes, ideally situated on a desirable corner homesite in Encore at Chatham Park! The stunning cooktop kitchen is perfect for culinary enthusiasts and entertaining alike, while the inviting fireplace creates a warm and welcoming gathering space. An elegant tray ceiling in the dining room adds a touch of sophistication, making every meal feel special. Beyond your front door, discover a lifestyle designed to inspire! Encore at Chatham Park is a vibrant 55+ community where neighbors become friends and every day brings new opportunities to connect, relax, and enjoy life. The spectacular 5,200-square-foot clubhouse serves as the heart of the community, featuring a fitness center, gathering spaces, and an exciting calendar of activities coordinated by a full-time Lifestyle Director. Spend sunny afternoons lounging by the resort-style pool, unwind in the hot tub, challenge friends to a game of pickleball or tennis, practice your short game on the putting green, or find a peaceful moment in the meditation garden. From social gatherings and special events to fitness activities and casual get-togethers, there's always something to look forward to! Experience more than just a beautiful home, discover an exceptional lifestyle, meaningful connections, and the freedom to enjoy your next chapter at Encore at Chatham Park!

179 Tantara Bnd, Pittsboro
200 Tantara Bend Bnd, Pittsboro
$471,260
2 Beds ⋅ 2 Baths ⋅ 10197867 MLS ⋅ ACTIVE Status
Experience refined, low-maintenance living in this beautifully designed paired villa by David Weekley Homes, located in the sought-after 55+ community of Encore at Chatham Park. Thoughtfully crafted for comfort and everyday ease, this single-level home blends open-concept living with elevated design details. At the heart of the home, the chef-inspired kitchen impresses with a large gathering island, built-in stainless steel appliances, abundant cabinetry, and sleek finishes--perfect for both casual mornings and effortless entertaining. The adjoining living and dining spaces are filled with natural light and extend seamlessly to a covered rear porch, creating a private outdoor retreat ideal for relaxing or hosting guests. The spacious Owner's Retreat offers a peaceful escape, complete with a spa-like bath featuring a zero-entry Super Shower, dual vanities, and a generous walk-in closet designed for optimal organization. Secondary spaces provide flexibility for guests, hobbies, or a home office, ensuring the home adapts to your lifestyle. Enjoy the ease of maintenance-free living with lawn care included, along with access to Encore's exceptional resort-style amenities. Residents enjoy a 5,200 sq ft clubhouse, fitness center, tennis and pickleball courts, resort-style pool and spa, putting green, meditation garden, gas firepits, and a full calendar of events curated by an on-site Lifestyle Director. Scenic walking and biking trails connect you to the vibrant Mosaic district for dining, entertainment, and everyday conveniences. Ideally positioned with quick access to US-64, 15-501, I-540, and RDU, this home offers the perfect blend of tranquility and accessibility--placing world-class healthcare, shopping, dining, and travel just minutes away.

200 Tantara Bend Bnd, Pittsboro
169 William Dr, Pittsboro
$299,985
3 Beds ⋅ 3 Baths ⋅ 10197207 MLS ⋅ ACTIVE Status
To be built. Discover the Roxbury Grande home plan at Griffin Farm Townes by Ryan Homes in Pittsboro, NC. There is still time to choose design features that fit your style. This luxury townhome is a must see with an open concept first floor featuring plenty of storage and a spacious island elevating the kitchen space. Upstairs features a spacious primary suite with two walk-in closets, while the primary bath has a double vanity and luxurious tiled roman shower. The secondary bedrooms provide flexible living space for a home office, guest suite, or whatever fits your lifestyle. The laundry room is conveniently located on the second floor and has the option to add the laundry tub Thoughtfully created for comfort and modern convenience with a professionally curated design package, LVP flooring, white cabinets, stainless steel appliances, quartz countertops, and gas range. Located 1 mile from downtown Pittsboro and minutes from Chatham Park and everyday needs.

169 William Dr, Pittsboro
179 William Dr, Pittsboro
$279,990
3 Beds ⋅ 3 Baths ⋅ 10197200 MLS ⋅ ACTIVE Status
To be built. Discover the Roxbury home plan at Griffin Farm Townes by Ryan Homes in Pittsboro, NC. There is still time to choose design features that fit your style. Situated on a wooded homesite, this townhome is the perfect blend of luxury and comfort, with an open concept first floor. The second floor includes a spacious primary suite with a tray ceiling, 2 walk-in closets, and a tiled walk-in shower Thoughtfully designed with modern finishes including LVP flooring, white cabinets, stainless steel appliances, quartz countertops, and a gas range. Located 1 mile from downtown Pittsboro with easy access to Chapel Hill & RTP. Start your homebuying journey today.

179 William Dr, Pittsboro
82 Arthur Alston Rd, Pittsboro
$225,000
2 Beds ⋅ 2 Baths ⋅ 10197100 MLS ⋅ ACTIVE Status
Looking for space, privacy, and the freedom to make a property your own? This 2-acre retreat offers it all—with no HOA and no restrictions! Enjoy the peace and privacy of a spacious lot while being just 10 minutes from downtown Pittsboro and approximately 30 minutes from Sanford or Chapel Hill. It's a great location for enjoying a quieter lifestyle without giving up convenient access to town, shopping, dining, and surrounding communities. Built in 1998, this well-maintained single-wide has had many upgrades and offers 2 bedrooms, 2 full baths, and generously sized rooms throughout. The open kitchen and dining area features stainless steel appliances and provides a comfortable space for everyday living and entertaining. The separate family room offers a cozy gathering space with an electric fireplace, while the dedicated laundry room adds everyday convenience. Outside is where this property truly shines. The level front and back yards provide plenty of usable space for gardening, pets, play, entertaining, or future projects. Enjoy morning coffee or evening gatherings on the front and back decks, and take advantage of the sturdy double storage shed for tools, equipment, and hobbies. With 2 acres of privacy, no HOA, no restrictions, numerous improvements, and a convenient location, this property offers the space and flexibility you've been looking for. Come see the privacy, the land, and all the possibilities this property has to offer!

82 Arthur Alston Rd, 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 .

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