Pittsboro Homes with Chatham - Margaret B Pollard Middle School

Welcome to Pittsboro, North Carolina—a charming town nestled in the heart of Chatham County that beautifully blends small-town charm with modern conveniences. With its picturesque landscapes, friendly community, and rich history, Pittsboro is an ideal destination for families, retirees, and anyone looking to enjoy a vibrant lifestyle in a serene setting.

One of the standout features of Pittsboro is its strong commitment to education, highlighted by the presence of the esteemed Margaret B. Pollard Middle School. This institution is known for its dedicated faculty, innovative curriculum, and a welcoming atmosphere that fosters growth and learning. Families seeking homes in this area will find a community that prioritizes the educational needs of its children, making it a perfect choice for young families.

Pittsboro itself is a treasure trove of local attractions, from quaint shops and delightful eateries to scenic parks and recreational opportunities. The nearby Haw River offers a chance for outdoor enthusiasts to enjoy kayaking, fishing, and hiking, while the historic downtown area invites residents to explore its unique boutiques and farmer's markets.

With a variety of housing options available, from charming single-family homes to modern townhouses, Pittsboro provides something for everyone. Whether you are drawn to the vibrant community spirit or the beautiful landscapes that surround this lovely town, Pittsboro is ready to welcome you home. Experience the perfect blend of tranquility and community right here in Chatham County!

Newest Pittsboro Homes with Chatham - Margaret B Pollard Middle School

$2,100,000

3 Baths ⋅ 10200459 MLS ⋅ ACTIVE Status

There's a new MARSHALL in town!! :) An exceptional opportunity to acquire 33+ STUNNING ACRES with remarkable lifestyle appeal and long-term investment potential! This unique destination property offers the rare combination of privacy, flexibility, and convenience in a growing area that still preserves a peaceful country atmosphere. With multiple perk sites potential (see agent), significant value has been established for multi-generational living, future homesites, rental income opportunities, subdivision potential, or strategic long-term investment. The property already showcases an impressive blend of renovated living spaces, newer and updated structures, farming and gardening areas, pasture(s), fencing, pond(s), trails, and thoughtfully designed separation options. Whether your vision includes a private family compound, income-producing retreat, hobby farm, estate property, or future development venture, this property provides the space, infrastructure, and versatility to bring those plans to life while maximizing future value. The current main residence, situated in the heart of the property, features 2 bedrooms / 1 full bath and has been updated throughout with comfortable, move-in-ready living spaces, rocking chair front porch and side deck. Additional improvements include an incredible oversized 3-car garage with workshop space and an attached studio-style living area offering 1 bedroom and 1 full bath—ideal for guests, extended family, rental income, or a private office. A separate "small home" adds even greater flexibility, featuring another 1 bedroom, 1 full bath, kitchen/living room, and even a picturesque window bedroom overlooking the pond & fountain, creating an inviting setting for guests, tenants, peaceful retreats, or creative pursuits. Further contributing to its appeal is a 2-stall horse barn with tack room, other small buildings and an additional 2nd large garage/storage building for RV, tractor and/or other farm toys. Properties offering this level of acreage, infrastructure, flexibility, and future upside are increasingly difficult to find, especially in a high-growth location. Enjoy an extraordinary country lifestyle today, while positioning yourself for future appreciation and income possibilities. With potential perk sites and extensive improvements already in place, many of the key steps have been completed, making this a compelling opportunity for buyers seeking both immediate enjoyment and lasting value. Owners are currently renting 2 of the living areas on a month-to-month basis - see LA for details - could be all moved out by closing or potentially stay pending buyer preference. Opportunities like this are rare—don't miss the chance to secure a property that can serve your family, your goals, and future generations to come!

865 Marshall Rd, Pittsboro

$395,000

3 Beds ⋅ 3 Baths ⋅ 10200417 MLS ⋅ ACTIVE Status

Discover the charm and convenience of Fearrington Village living in this spacious end-unit townhome, offering an abundance of natural light, generous living spaces, and a great pond view! Nestled among mature landscaping, this one-owner home presents a wonderful opportunity to add your personal touches and updates while enjoying an established community known for its exceptional lifestyle. Step inside to find soaring vaulted ceilings, beautiful hardwood floors throughout the main level, and a versatile floor plan designed for comfortable everyday living and entertaining. The inviting living room features a cozy gas fireplace and flows seamlessly into a light-filled sunroom with access to a private side deck. A cheerful breakfast area complements the kitchen, while the separate dining room provides the perfect setting for gatherings. The spacious main-level primary suite offers the ease of first-floor living, complete with a generous walk-in closet. Upstairs, two additional generously sized bedrooms or flexible living spaces offer endless possibilities for guests, a home office, or hobbies, along with abundant walk-in storage. Enjoy low-maintenance living with HOA-maintained exterior features, allowing more time to explore Fearrington Village's scenic walking trails, charming shops, restaurants, and vibrant community activities. Additional conveniences include a detached one-car garage maintained by the HOA, which is not separately deeded, and a dedicated parking space directly in front of the home. Ideally located just minutes from Chapel Hill, UNC, RTP, RDU, and Jordan Lake, this property offers a rare opportunity to create your own retreat in one of the area's most beloved communities.

458 Beechmast, 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

$785,000

3 Beds ⋅ 2 Baths ⋅ 10199970 MLS ⋅ ACTIVE Status

Located on a quiet street in the charming Bradford Place neighborhood of Fearrington Village, with ideal east-west exposure, lies this ideal, warm, and charming cottage-style modern farmhouse designed and appointed to fit the Fearrington Village ethos. The home was fully upgraded in 2022. The main level consists of approximately 2533 square feet. Additionally, approximately 1234 square feet of living area are found on the lower level of the home, this area is accessed by a path that leads to the back patio. The home sits on a .5-acre lot with dense forest and a creek. The home's main entrance overlooks a generously irrigated, a very private and lush courtyard populated with dozens of vines, flowers, and trees. Anchoring the courtyard is a mature Cherry tree providing ample shade and stunning blossoms. The charming courtyard features a large brick terrace beneath a grapevine covered pergola, ideal for morning coffee or evening wine with birdsong. The walled courtyard and gardens are truly an eco-system for small indigenous wildlife, bees, and butterflies. The small, raised-bed garden is perfect for growing herbs. The forest can be seen upon entering the home and can be enjoyed by all spaces on the west side including the 3-sided window-walled dining room, open deck and screened porch which lend a "Tree House" feel to the upper living level. "Apricot Sunsets" can be seen through the trees. The foyer gives access to the fully private main suite including a large main bedroom with a window wall overlooking the forest and perfect for peaceful sleep. Aromatic, dual cedar-lined closets with built-ins, a spacious bath with windows opening onto the lush courtyard, a large tiled shower, a claw foot tub, two furniture-style vanity sinks, a large built-in storage cabinet, and a separate, private WC. The main wing hallway features floor-to-ceiling cabinets for generous storage that complete the main suite. Also, from the foyer lies a large, bright, and sunny flex room featuring a bay window with views of the courtyard. Butterfly bushes grace the view to provide a "Butterfly Ballet" when in season. The main level provides a spacious great room with soaring ceilings and views of the forest through the adjoining window-walled dining area. A custom stone fireplace anchors the room and features a 400-year-old historic mantle and is flanked on both sides with generous built-in bookcase/cabinets. An open kitchen completes the space with custom-open shelves with generous LED up and down lighting and generous storage. The kitchen features an RO water filtration system, a gas range island/breakfast bar combo, a Samsung "Smart" refrigerator, a new oven (2025). The hallway from the kitchen features two large pantries, a cedar-lined coat closet and access to the large, fully appointed laundry room all leading to the garage entrance. The spacious, light-filled laundry room features built ins, a custom, tiled dog shower, and pet feeding area. A pair of Maytag machines are included. Two more spacious bedroom/office rooms (one opens to the large, screened porch) and a charming full hall bath lie directly off the kitchen. The hall opens to a double garage with custom, epoxy coated floors and ample storage. Ample and convenient outdoor space is provided for pets. A door leads to a fenced, yard/dog run which extends the entire length of the southern side of the home. The other garage side door gives access to the courtyard for ease with gardening projects. The spacious lower level has been fully appointed with many custom finishes and a custom "Fearrington" mural to create a unique retreat complete with a bar, gaming, and TV area. The area is separated from a workshop space and high-ceilinged storage that houses dual HVAC systems. Located within a closet in the space is the whole-house water filtration system. Low-maintenance landscaping has been selected and is maintained by an extensive drip system.

1390 Bradford Pl, Pittsboro

$1,650,000

4 Beds ⋅ 4 Baths ⋅ 10199904 MLS ⋅ ACTIVE Status

Discover a curated expression of modern luxury and timeless Tudor architecture in this exceptional home, featuring a custom plan by renowned architect Chuck Frusterio and built by award-winning Dunning Custom Homes. Situated at the end of a cul-de-sac on a 1+ acre homesite in beautiful Stonecrest at Norwood, this property offers a peaceful setting framed by mature trees for added privacy. From the striking arched front door to the cozy library nook, every detail has been carefully selected by the owners to create a home that is both distinctive and inviting. Offering 4 bedrooms, 4 full baths, a media room, and a sunroom, this remarkable residence showcases custom, elevated finishes, and exceptional craftsmanship throughout. The chef's kitchen features inset cabinetry, a Thermador range, a Bosch dishwasher, built-in Thermador refrigerator AND freezer, an oversized cherry wood island custom crafted by Raleigh Reclaimed, and a 5-foot galley sink with dual faucets. The adjoining scullery adds a beverage refrigerator, instant-hot water faucet, and so much storage! The sizable family room flows into a serene sunroom, where a shared two-sided fireplace creates a seamless connection between the spaces. Surrounded by views of trees and nature, the sunroom offers an inviting retreat to unwind and enjoy the peaceful setting. A main-level guest suite with an adjacent full bath offers a welcoming retreat for visitors or those needing first-floor living. Upstairs, the primary suite is a private sanctuary with automated Lutron shades and a spa-inspired bath featuring custom tilework, multi-head shower system, and inset cabinetry. A secondary bedroom with upgraded carpeting and Lutron shades offers its own ensuite bath. The media room is designed for entertaining with blackout drapery, a wet bar, beverage refrigerator, and an 85-inch Samsung LED TV. Another bedroom, full bath, and conditioned storage complete the second floor. Additional designer details include Visual Comfort lighting, Coppersmith exterior fixtures, a copper entry roof, and custom window treatments throughout. Modern comforts and thoughtful technology include a custom Brinks security system with five exterior cameras, solar panels, a Tesla Powerwall, an EV charger, and a 3-car garage. This private homesite with a fenced backyard offers a peaceful setting with a nearby trailhead, community walking trails, and a beautifully appointed pavilion with a fireplace, all within convenient reach. This is a truly distinctive modern estate where architectural character, personalized design, and luxury come together beautifully. Video walkthrough: bit.ly/650Stonecrest-Video

650 Stonecrest Way, Pittsboro

$575,000

3 Beds ⋅ 3 Baths ⋅ 10199766 MLS ⋅ ACTIVE Status

Beautifully situated on a private, wooded lot, this inviting three-bedroom home combines comfortable living with thoughtful updates. Refinished hardwood floors, new carpet, fresh interior paint, and updated bathrooms with new tile and lighting give the home a fresh, move-in-ready feel. The kitchen features granite countertops, an eat-in island, and tile backsplash, and opens to the family room, where a gas fireplace creates a warm and welcoming gathering space. A separate living room opens to the dining room, offering additional space for relaxing and entertaining. The primary suite features a spacious bath with a separate shower and corner tub, along with a walk-in closet. The laundry room includes built-in cabinetry, a new countertop, and new tile for added style and convenience. Outside, a large deck overlooks the beautiful, wooded backyard, while a custom fire pit area with hand-selected boulders creates a special place to gather with family and friends or simply unwind in the peaceful surroundings. Ample parking provides plenty of space for family, friends, and guests. With no HOA, you can enjoy added flexibility in how you use your property. Conveniently located just minutes from downtown Pittsboro and Chapel Hill, this home is ready for you to move in and enjoy!

120 Hamlet Grove Dr, Pittsboro

$499,900

2 Beds ⋅ 2 Baths ⋅ 10199016 MLS ⋅ ACTIVE Status

LOCATION, LIFESTYLE & THOUGHTFUL UPGRADES! Discover the perfect blend of comfort, convenience and low-maintenance living in the premier 55+ community of Encore at Chatham Park! Ideally situated just steps from the community amenity center, this beautifully appointed home offers an exceptional location with the central mailbox station and convenient guest parking directly across the street. Designed for easy living and entertaining, the open-concept floor plan features luxury vinyl plank flooring, a spacious kitchen with quartz countertops, oversized island, stainless steel appliances and abundant storage. The inviting primary suite offers a tray ceiling, dual vanities and an oversized zero-entry shower. A standout interior upgrade is the versatile den/second bedroom featuring a custom Murphy bed wall unit with additional built-in storage—perfect for accommodating overnight guests while maximizing everyday living space. Another highlight is the beautiful three-season sunroom with a cozy fireplace overlooking peaceful green space, creating an inviting retreat for morning coffee, relaxing afternoons or evening gatherings. Enjoy resort-style amenities including a clubhouse, swimming pool, fitness center, pickleball and tennis courts, along with an active social calendar. Leave the car at home and enjoy golf cart access to nearby restaurants, MOSAIC's outdoor entertainment venues, shopping and UNC Health medical services! This exceptional golf-cart-friendly lifestyle puts dining, entertainment and everyday conveniences within easy reach. More than a home, this is an opportunity to enjoy an exceptional active adult lifestyle where convenience, community and comfort come together!

125 Prospect Pl, Pittsboro

$550,000

10198913 MLS ⋅ ACTIVE Status

Unique opportunity to purchase a large 1.47 acre lot and a 1.3 acre lot for a total of 2.7 acres located1.3 miles from the circle in downtown Pittsboro! Additional layout also potentially available (2.135 total acres for $475k). Lot 2 Homesite is level, with rolling contour through the trees. Lot 1 homesite is level and sits high overlooking pond. Very private setting, nestled within a mature hardwood forest ecosystem with a neighboring large spring-fed pond. Very minimal restrictions (chickens are allowed!). Deer, hawks, pileated woodpecker and great blue heron live here. Bald Eagle and Osprey have visited in the last two months. Monarch butterfly visited yesterday. Mature Beech and Oak trees abound. This is a wonderful setting with a country feel yet extremely close to town. You can zip in and zip out and be back within minutes! Biking or walking to downtown is also easy to do. Access off of Hwy 902. Lots this size this close to town are very unique and rare. It is an incredible opportunity to purchase here in this growing town that is the next to boom... the population of Pittsboro has hovered around 5,000 and is now expected to reach 85,000 in the next 15 years. The value of these lots appreciates tremendously each year.

910 Nc-902 And 902 Hwy, Pittsboro

$300,000

10198592 MLS ⋅ ACTIVE Status

Unleash the potential of this serene, wooded 5 acre homesite located at 96 Deer Run Rd in desirable Pittsboro. Offering privacy, mature trees, and a tranquil rural atmosphere, this property is the perfect canvas for your custom home, private retreat, or future investment project. Conveniently situated in Chatham County with easy access to downtown Pittsboro, Jordan Lake, Apex, and the Triangle area, this residential lot features an existing well and septic on site (buyer to verify condition and capacity). The property is being sold strictly as-is for land value and includes an existing, non-habitable single-wide mobile home that will not be removed by the seller, making this an ideal project for cash buyers, investors, or land renovators. Bring your builder and your vision—cash or specialty land financing is preferred due to the condition of the structure. Please note that buyers are responsible for site clearing and verifying all land-use regulations, zoning, and utility suitability with Chatham County, and visitors should not attempt to enter the existing structure. Contact the listing agent today for more information or to schedule a private walk of the lot!

96 Deer Run, 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

$536,000

2 Beds ⋅ 2 Baths ⋅ 10198382 MLS ⋅ ACTIVE Status

Picture yourself in the peace and beauty of a heart home. Inspired by hospitality and comfort. Surrounded by the healing essence of nature and crafted carefully into every detail of the home. A place to live, create and nurture. Known lovingly as Birds Nest, this cherished home is ready for its next generation. A magical refuge of almost 6 acres of forest with trails, a meandering creek, and open space for gardens and play. Custom built by hand of live edge pine clapboard, the home embraces the elements of wood, stone and mountain allure. Enter the rustic welcome deck made for tales, tonics, bird songs and gentle breezes. Step inside and admire the lodge-like two-story fireplace of hand stacked stones gathered from the land, the centerpiece of the open living room, kitchen and dining area. Bask in the mosaic light that flows through the rich colors of stained glass and feel the warmth of the artsy shiplap walls. Make your way up to the loft rooms for rest or retreat. Escape to the spa-like primary en-suite where you find privacy and provision with windows that showcase the outdoors as your living canvas. Located in the coveted Chatham County Haw River area in a sought-after large parcel neighborhood. Convenient to Pittsboro, Chapel Hill/Carrboro, Durham, UNC, RTP and RDU. Embrace the cabin life. Nothing about this property is ordinary or untouched by grace. This is home.

400 River View Rd, Pittsboro

$539,900

3 Beds ⋅ 2 Baths ⋅ 10198340 MLS ⋅ ACTIVE Status

Tucked among the trees in the heart of historic Fearrington Village, this striking 3-bedroom, 2½-bath contemporary home offers modern design, exceptional craftsmanship, and serene wooded views from nearly every room. With its clean architectural lines and abundant natural light, the home lives like a private modern treehouse--peaceful, elevated, and beautifully connected to nature. Inside, thoughtful design meets everyday functionality. The kitchen features custom cabinetry, granite countertops, stainless steel appliances, tile flooring, and generous windows that fill the space with natural light. Custom cabinetry continues throughout the home in the bathrooms, closets, and laundry, creating a cohesive aesthetic and abundant storage. The spacious living areas showcase vaulted ceilings, skylights, hardwood floors, and a fireplace, all framed by expansive windows overlooking the surrounding woods. The flexible third bedroom offers endless possibilities--ideal as a home office, library, gym, craft room, or music studio. A two-car garage and a walk-in crawl space with a wine cellar provide exceptional storage options rarely found in homes of this size. Beyond the home itself, the lifestyle is what truly sets this property apart. Fearrington Village is consistently recognized as one of the Triangle's most desirable communities, offering a rare blend of charm, connection, and natural beauty. Residents enjoy the village shops and restaurants, the Tennis and Pickleball Association, and the opportunity to join the swim and croquet club. Outdoor living here is a way of life. Scenic walking trails and beautifully maintained gardens wind throughout the village. Visit the beloved Belted Barnyard animals or take a short drive to Jordan Lake for boating, swimming, hiking, and eagle-spotting. The nearby Haw River offers additional opportunities for kayaking, fishing, and peaceful exploration. Whether you prefer an active afternoon outdoors or a quiet morning walk among the trees, the options are abundant. Equally special is the sense of community. Fearrington Village is home to dozens of resident-run clubs spanning interests from arts and literature to fitness and travel, creating countless opportunities to connect and engage. The Fearrington Cares organization, founded to support the health and daily living needs of residents, further reflects the thoughtful and supportive spirit of the neighborhood. This is more than a home--it is a modern retreat set within a vibrant, connected community where nature, lifestyle, and neighborly warmth come together beautifully.

246 Fox Rdg, 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 .

Pittsboro Homes with Chatham - Margaret B Pollard Middle School

Newest Pittsboro Homes with Chatham - Margaret B Pollard Middle School

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