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436 Wintercrest E, Pittsboro
$385,000
3 Beds ⋅ 2 Baths ⋅ 10161143 MLS
This bright and spacious 3 bedroom end-unit townhome has a master suite, dining room, living room, eat-in kitchen, and a 4 season sunroom on the main floor. Home is situated among mature landscaping, colorful bushes and lush gardens, offering privacy and tranquility. This charming community is located in desired Fearrington Village, a picturesque setting inspired by old English Villages, with small shops, boutiques, fine dining, on-site medical and historical Fearrington Inn, available to all. Rural attributes like the many barns, chicken coop-silo, the famous Beltway cows, and goats make this location unique. The village is conveniently located between Pittsboro and Chapel Hill with easy access to great hospitals, health care, outdoor activities and shopping.

436 Wintercrest E, Pittsboro

186 Millennium Dr, Pittsboro
$382,000
3 Beds ⋅ 3 Baths ⋅ 10127172 MLS ⋅ Lennar BLDG.
MOTIVATED SELLER! Offering to pay up to $5k towards closing costs with an acceptable offer. This modern townhome, just a few years old, is an immaculate home located in the heart of Pittsboro. Offering stylish, contemporary vibes, it features 3 spacious bedrooms and 3.5 bathrooms. The open floor plan is perfect for entertaining, with a large kitchen island, granite countertops, and seamless flow into the living and dining areas. Enjoy the outdoors year round in your screened-in porch. Located in Chatham Park, the home is close to scenic walking trails, Knight Farm Community Park, and Paddles the area's pool and fitness center, available with an additional membership. With local restaurants, shops, and so much more just moments away, this home truly offers the best of modern living in a vibrant, connected community. All appliances convey and 7 year structural warranty.

186 Millennium Dr, Pittsboro

40 Broadoak Ln, Pittsboro
$380,800
3 Beds ⋅ 3 Baths ⋅ 10135336 MLS
Introducing the Ember B plan, part of The Elements Collection at NoVi in Chatham Park! This thoughtfully designed new construction home on a corner lot offers 3 bedrooms, 3 full bathrooms, and a 2-car detached garage, all just a short walk from the brand-new Chatham YMCA. The main level features an inviting covered front porch, an open-concept layout, and a spacious walk-in kitchen pantry. A convenient first-floor secondary bedroom with a full bathroom provides flexible living options for guests, work, or multigenerational needs. Upstairs, the primary suite offers comfort and privacy, joined by an additional bedroom, full bath, and a versatile loft, perfect for a second living area, office, or play space. Enjoy outdoor living on the covered rear porch, ideal for morning coffee or evening relaxation. With designer-ready exterior schemes available, you can personalize the look of your new home—contact us to learn more! Located in the heart of Pittsboro's award-winning Chatham Park community, this home combines modern design, beautiful finishes, and unbeatable convenience.

40 Broadoak Ln, Pittsboro

73 Parkland Dr, Pittsboro
$378,730
3 Beds ⋅ 3 Baths ⋅ 10110916 MLS
Smart Entry Opportunity into Homes by Dickerson | Recent Price Improvement Discover exceptional value and timeless craftsmanship in this beautifully designed new construction home by award-winning Homes by Dickerson. A recent price improvement reflects current market conditions, creating a smart opportunity to secure custom-quality construction in Chatham Park. The Flint B plan offers a thoughtful blend of style, efficiency, and livability. Projected for completion in late December, this two-story home features 3 bedrooms, 2.5 baths, and a versatile loft—perfect for a home office, media space, or playroom. Inside, 1,565 square feet of well-planned living space showcases the quality Homes by Dickerson is known for, including designer lighting, quartz countertops, premium cabinetry, and refined finishes throughout. The open-concept main level is ideal for everyday living and entertaining, while the upper level offers generously sized secondary bedrooms and a serene primary suite retreat. Curb appeal shines with vertical panel siding and stone accents, complemented by a detached 2-car garage that enhances the classic neighborhood streetscape. Located in the Novi section of Chatham Park, this home is within walking distance of the new Chatham Park YMCA and pool, with dining, shopping, and community amenities just minutes away. A rare chance to own a new Homes by Dickerson residence at an attractive entry point—don't miss this opportunity in one of Pittsboro's fastest-growing communities.

73 Parkland Dr, Pittsboro

119 Hillsboro St, Pittsboro
$375,000
10160135 MLS
Pittsboro Main Street! Prime commercial opportunity in the heart of Downtown Pittsboro! This one-level brick building offers excellent visibility along Hillsboro Street with strong line-of-sight exposure in a rapidly growing area. Ideal for retail, office, or service-based businesses seeking a high-traffic location with public parking nearby. Property features a recorded survey for added confidence and ease of transaction. Open interior layout provides flexibility for a variety of uses. Please note: no kitchen or grease trap - perfect for concepts that do not require food prep infrastructure. Surrounded by ongoing development and increasing foot traffic such as Chatham Park, Disney/Asteria, this location presents outstanding rental income potential for investors or owner-occupants looking to establish a presence in one of the region's most dynamic downtown corridors.

119 Hillsboro St, Pittsboro

917 Roads End, Pittsboro
$371,000
3 Beds ⋅ 2 Baths ⋅ 10168648 MLS
Tucked away on 5 beautiful acres, this charming cabin offers the kind of lifestyle people dream about--peaceful mornings filled with birdsong, gentle rain dancing through the trees, and nature all around you. Equal parts cozy retreat and welcoming gathering place, this home captures the warmth and simplicity of country living without sacrificing comfort or convenience. Inside, heart pine floors and stunning wood throughout. There is a soaring vaulted ceiling, and a spacious kitchen and dining area. Everything is thoughtfully created to foster an inviting atmosphere perfect for both quiet evenings and lively get-togethers. Rich interior log walls add timeless character and rustic charm throughout the home. Step outside onto the expansive deck, where fresh Chatham County air, wooded views, and starry night skies make every moment feel like a getaway.

917 Roads End, Pittsboro

484 Beechmast, Pittsboro
$370,000
3 Beds ⋅ 3 Baths ⋅ 10180160 MLS
Welcome home to this spacious 2,200+ sq ft end-unit townhome in coveted Fearrington Village, just minutes from Chapel Hill, UNC, RDU, RTP, and Jordan Lake. Offering generous space at a terrific value, this home features vaulted ceilings and skylights that fill the interior with natural light, while hardwood floors flow throughout the main level. The living room opens to a sunny flex space—perfect for a home office or sunroom—with direct access to the side deck, ideal for morning coffee or evening unwinding. The first-floor owners' suite offers a peaceful retreat with a large walk-in closet. Two additional generously sized bedrooms complete the plan, including one with a wood-floored side room perfect for a craft room, office, or reading nook. Surrounded by mature, established landscaping, this end unit offers comfort, convenience, and effortless low-maintenance living—the HOA covers roof, garage, exterior maintenance, and mow & blow. A one-car detached garage adds everyday convenience. Enjoy all that Fearrington Village has to offer: tennis and pickleball courts, scenic walking trails, charming shops and restaurants, and a vibrant calendar of clubs and activities. A rare opportunity to live low-maintenance without compromising on space, light, or lifestyle.

484 Beechmast, Pittsboro

66 Bellemont Rd, Pittsboro
$367,000
3 Beds ⋅ 2 Baths ⋅ 10148201 MLS
Welcome to 66 Bellemont Rd, a polished ranch home in much sought after Chatham Forest. Stroll up to this single owner, single level home featuring 3 bedrooms , 2 baths. Cozy up to the formal slate surround F/P while you admire the gleaming hardwoods in the Foyer, LR and separate DR. Two great size bathrooms have every appointment to suit you. This inviting home has recent updates that include a new shower in the primary bath that will have you singing, new carpet in the bedrooms that invite you to sink your toes in and new interior paint throughout for all your works of art. There is a considerable amount of floor space for storage in the attic of this home. It is accessed by pull down stairs. After you grill your burgers on the 12 x 10 back deck you can picnic back there to watch the birds or hang out on the newly refreshed front porch.! Other upgrades in recent years include a new roof in 2020, HVAC replaced in 2019 HVAC along with a Gas Water Heater in 2019. Outside you have LP Smart siding complimented by cedar shakes that'll have you relaxin' instead of paintin'. Pack your patio table and chairs, wine glasses, bird feeders and a good book because the outdoor spaces here will ask you for them! This established community will have you cruising the sidewalks, gazing at the beautiful trees or walking to downtown Pittsboro or Chatham Park. Great Pittsboro location within 30 minutes of Sanford, Pittsboro, Apex, Cary, Raleigh, RTP or 35 to RDU! Come Home!

66 Bellemont Rd, Pittsboro

56 W Cornwallis St, Pittsboro
$360,000
3 Beds ⋅ 2 Baths ⋅ 10183829 MLS
Welcome to this charming and inviting home in desirable Pittsboro, perfectly blending cozy comfort with modern convenience. The open floor plan creates a welcoming flow ideal for everyday living and effortless entertaining. Hardwood floors and durable ceramic tile run throughout—no carpet anywhere—delivering easy maintenance and timeless appeal. The generous, well-equipped kitchen shines as the heart of the home, featuring a gas cooktop, wall oven, abundant cabinetry and storage, making meal prep a delight. Just steps away, the living room anchors around a stunning stone fireplace. Additional highlights include smooth ceilings and a convenient separate laundry closet. Step outside to your private outdoor oasis: a screened side porch for peaceful mornings, a spacious deck, patio for dining al fresco, and a large fenced backyard complete with a handy shed. This setup is ideal for pets, play, gardening, or entertaining in complete privacy. Best of all, enjoy walkable access to vibrant Downtown Pittsboro shops, dining, and top-rated schools. This move-in ready gem also includes a washer, dryer, refrigerator, and Reverse Osmosis drinking water system that convey with the sale—saving you time and money from day one.

56 W Cornwallis St, Pittsboro

166 Wintersage, Pittsboro
$360,000
3 Beds ⋅ 2 Baths ⋅ 10171914 MLS
3 Bed | 2 Bath | True Single-Level Living on a Private Wooded Lot Between Pittsboro & Chapel Hill Experience the ease of true single-level living in this light-filled home, ideally situated between Pittsboro and Chapel Hill in a desirable Village community. Designed with both comfort and accessibility in mind, the home features zero-step entry from the oversized two-car garage, allowing seamless access without navigating interior or exterior stairs—an exceptional feature for those seeking long-term convenience and aging-in-place functionality. Inside, cathedral ceilings and multiple skylights fill the home with an abundance of natural light, creating an open, airy atmosphere throughout the spacious living and dining areas. A versatile flex room overlooking the front yard offers endless possibilities as a home office, art studio, library, or hobby space. Set on a private, wooded 0.81-acre cul-de-sac lot, the expansive deck provides the perfect place to enjoy morning coffee, entertain guests, or simply relax while taking in the peaceful natural surroundings. A large concrete driveway, oversized garage, and newer roof add to the home's everyday functionality and value. Residents also enjoy access to the community pool and the highly regarded Fearrington Cares program, which offers a variety of complimentary services and support designed to enhance everyday living. Offering privacy, accessibility, abundant natural light, and an unbeatable location just minutes from shopping, dining, and all that Pittsboro and Chapel Hill have to offer, this home is a rare opportunity. Home is being sold as-is.

166 Wintersage, Pittsboro

250 William Dr, Pittsboro
$352,490
3 Beds ⋅ 3 Baths ⋅ 10179782 MLS
Quick move-in - Welcome to the Roxbury home plan at Griffin Farm Townes by Ryan Homes in Pittsboro, NC. This luxury townhome includes a 1-car garage and is situated on a wooded homesite with a natural view with a rear patio. Professionally curated design for comfort and modern convenience with LVP flooring, upgraded cabinets including a spacious sage colored island, stainless steel appliances, quartz countertops, gas range, soft close drawers, and black finishes. Enjoy an open floorplan on the main level and a spacious owners suite with tray ceilings and two walk-in closets on the second floor. Two additional bedrooms on the second floor allow for extra flexibility to fit your needs. Located 1 mile from downtown Pittsboro and minutes from Chatham Park and everyday needs. Photos are of similar home for illustrative purposes only.

250 William Dr, Pittsboro

79 Parkland Dr, Pittsboro
$350,000
3 Beds ⋅ 3 Baths ⋅ 10110920 MLS
High-quality, Energy Star® Certified new construction in Chatham Park NoVi. Welcome to the Flint A by award-winning Homes by Dickerson—a thoughtfully designed home that blends modern efficiency, timeless architecture, and the custom-quality craftsmanship the builder is known for. Scheduled for completion January 2026, this well-planned two-story home offers 3 bedrooms, 2.5 baths, and a versatile loft, ideal for a home office, media room, or flex space. With 1,569 square feet of intentionally designed living space, every detail balances style, comfort, and functionality. The open-concept main level is perfect for everyday living and entertaining, featuring designer lighting, quartz countertops, premium cabinetry, and curated finishes throughout. Upstairs, you'll find generously sized secondary bedrooms and a serene primary suite designed for comfort and retreat. Exterior details include eye-catching vertical siding, brick accents, and a detached 2-car garage, delivering classic neighborhood charm and enduring curb appeal. Located in the vibrant NoVi neighborhood of Chatham Park, residents enjoy walkable access to the new YMCA and pool, with shopping, dining, parks, and miles of trails just minutes away. Energy Star® Certified for enhanced comfort, efficiency, and long-term savings. Newly priced at $399,900—the lowest-priced home currently available in the community. A rare opportunity to own a designer-crafted new home in one of Pittsboro's fastest-growing and most sought-after communities. This home will not last.

79 Parkland Dr, Pittsboro

143 Parkland Dr, Pittsboro
$345,990
3 Beds ⋅ 3 Baths ⋅ 10151905 MLS ⋅ Sampson D BLDG.
Move-in ready now and priced under $400K in Chatham Park! Don't miss this opportunity to own a beautifully upgraded Sampson townhome at 143 Parkland Drive—complete and ready for its new owner. The bright, open-concept main level features a gourmet kitchen with quartz countertops and GE appliances, a cozy fireplace, designer finishes, and a private brick courtyard perfect for morning coffee or relaxing after work. Upstairs, the spacious primary suite includes a spa-inspired bath with a tiled walk-in shower, bench seating, dual vanities, and generous closet space. A versatile loft plus two additional bedrooms provide flexibility for guests, a home office, or hobbies. Enjoy the Chatham Park lifestyle with NoVi Green, the YMCA, parks, trails, and Mosaic's dining, entertainment, and events nearby, plus convenient access to Chapel Hill, Durham, RTP, UNC, and Jordan Lake. Why wait to build? This home is ready now. Schedule your tour today and ask about available builder incentives, including closing cost assistance! Builder incentives available, including closing cost assistance. Contact onsite sales team for current incentive details.

143 Parkland Dr, Pittsboro

309 Baneberry Close, Pittsboro
$345,000
3 Beds ⋅ 2 Baths ⋅ 10140948 MLS
This Fearrington Village townhome is in the Countryhouse section - the first townhome complex built in the Village.309 Baneberry is the middle unit in a 3-unit building. It has 5 skylights making the home very bright. There is a bay window in the front and a wall of windows across the back keeping it bright and light filled. The great floor plan includes a spacious kitchen and breakfast room. There is a main level primary bedroom. The living room has a soaring ceiling and a gas log fireplace. Spacious dining room overlooks the screened porch. Two more bedrooms plus another full bath and a loft office with built-in bookcases on the second level. Walk-in closets and lots of storage space. Roof replaced in 2023. Private back yard. New carpeting throughout and parquet floors refurbished. Countryhouse Townhouses are well manages and solvent. This fairly priced home is waiting for a buyer who is ready make this wonderful house their own. Friendly neighbors await you. Fearrington offers restaurants, shopping,etc.

309 Baneberry Close, Pittsboro

94 Silverstone Dr, Pittsboro
$340,000
3 Beds ⋅ 3 Baths ⋅ 10155773 MLS ⋅ Anderson Homes BLDG.
This Rare Sunlit Updated Split Level on .31 Acre Lot w/Fenced Backyard within 1 Mile of Downtown Pittsboro's Historic Traffic Circle is Sure to Check a Lot of Boxes!! Perfect for Today's Style of Living!! With this Home Facing Directly West You get Sunlit Mornings on your Backyard Deck/Large Fenced Dog Friendly Backyard & Rear Windows! Plus Incredible Evening Sunsets Daily off the Front of the Home!! Now You Enter this Home to a Beautiful Open Vaulted Living Rm, Kitchen, & Dining Rm Family Combination Gathering Space! The Gourmet Kitchen Features Granite Counter Tops & Updated Stainless Steel Appliances!! Nice Food Pantry! Breakfast Bar! French Door to Deck off Dining Rm! Upper Floor Features a Private Sleeping Oasis w/Primary Bedroom Featuring 2 Closets & Updated Private Full Bath! Also Bdrm 2 up w/Full Bath next to it!! No Shared Bedroom Walls! Down Below Main Level is a Private Oasis Perfect for Extended Stay Guest Suite/Adult Children/ Children's Play Space w/Private Bedroom & Bonus Rm w/Gas Log FP!! Laundry Rm! Full Bath w/Nice Shower!! Direct Access to Backyard! This Home Also Features Updated Flooring, Granite Tops, Toilets, Paint Accenting and More!! Out Back you have a Nice Grilling Deck and Wooded Tree Line on Back Line of a Large Private Backyard! Great Lot Size & Plan! Less Than a Mile Walk to Downtown Pittsboro! Jordan Lake Right Around the Corner! Welcome Home!

94 Silverstone Dr, Pittsboro

80 Millbrook Dr, Pittsboro
$338,000
3 Beds ⋅ 3 Baths ⋅ 10145214 MLS
This well-maintained two-story home is located in the highly walkable Powell Place neighborhood, known for its sidewalks, multiple parks, ponds, and playgrounds. Freshly painted! Conveniently situated near all the amenities of Pittsboro, the home also offers easy access to Highway 64, making for an approximate 20-minute drive to Apex. High-speed fiber internet is available, making working from home or streaming a breeze. The home features three bedrooms and two and a half bathrooms with a thoughtful, functional layout. The main level offers a bright, open living and dining area, ideal for everyday living and entertaining. The eat-in kitchen is equipped with stainless steel appliances, a tile backsplash, 42-inch cabinets, a pantry, and newly installed kitchen flooring (February 2025). A mix of carpet, hardwood, tile, and vinyl flooring provides comfort and durability throughout. All bedrooms are located on the second level, including a spacious primary suite with a walk-in closet and a relaxing garden tub. The second-floor laundry room adds everyday convenience. Recent updates include a new hot water heater (December 2025), fully replaced HVAC condenser, coil, fan, and handler (August 2024), a new dishwasher (February 2025), and new carpet throughout (February 2026). Light fixtures throughout the first floor and the half-bath vanity were upgraded in 2025. Outdoor living is enhanced by a covered front porch, rear patio, rear attached storage, and a fenced backyard featuring a custom wood privacy fence installed in July 2024. The HOA covers all exterior maintenance, offering low-maintenance living. This move-in-ready home combines modern updates, comfort, and an excellent location.

80 Millbrook Dr, Pittsboro

317 Wood Rd, Pittsboro
$325,000
3 Beds ⋅ 2 Baths ⋅ 10156648 MLS
Located in the desirable Hickory Haven neighborhood, known for its large wooded lots and peaceful privacy, this property offers 4.85 acres of serene living in the heart of Chatham County. This 2100+ sqft manufactured home features a thoughtfully designed split floor plan, with two separate wings divided by a central kitchen and living area--perfect for a home office, multi-generational living, or a private guest retreat. Enjoy bird watching from the screened porch overlooking the spacious fenced yard, and take advantage of the 2-bay storage building ideal for vehicles, hobbies, or extra storage. Recent updates include a new roof (2016) and HVAC system (2018), offering added peace of mind. Conveniently located just 15 minutes from Chatham Park in Pittsboro, you'll enjoy the perfect balance of quiet country living with easy access to shopping, dining, and amenities.

317 Wood Rd, Pittsboro

41 Glendale Dr, Pittsboro
$290,000
3 Beds ⋅ 2 Baths ⋅ 10175754 MLS
Charming One-Level Home on Nearly 1 Acre of Private, Wooded Chatham County Land! Tucked away on a peaceful 0.93-acre wooded lot in sought-after Chatham County, this well-maintained 2015-built home offers the perfect blend of privacy, space, and style — all at an exceptional value. With 3 bedrooms, 2 full baths, and 1,817 square feet of single-story living, this one checks all the boxes. Step inside to a welcoming open floor plan anchored by a spacious living room featuring crown molding, elegant arched pass-throughs, ceiling fan, and durable LVP flooring throughout. The impressive kitchen is a true centerpiece — boasting a large center island with bar seating, stylish countertops, rich dark wood cabinetry, recessed lighting, and a full black appliance package. A bright dining area with wooded views and a charming private nook with dual windows round out the main living space. The generous primary suite features a ceiling fan, wooded views, and a luxurious en-suite bath with dual vanity, an abundance of built-in storage cabinetry, and a walk-in glass-door shower. Two additional bedrooms share a well-appointed full bath with tub/shower combo and a single vanity. Outside, a covered front entry with a wood deck and staircase sets the tone, while the expansive backyard offers mature trees, privacy fencing, and room to roam. Located just minutes from downtown Pittsboro with easy access to US-64, and zoned for Chatham Grove Elementary (1 mi), Margaret B. Pollard Middle (1 mi), and Seaforth High School — this is Chatham County living at its finest.

41 Glendale Dr, Pittsboro

625 Harts Creek Dr, Pittsboro
$275,000
10185492 MLS
Discover the perfect setting for your dream home on this beautiful wooded acreage offering privacy, peace, and tranquility while still keeping you close to everything you need. Enjoy the quiet of country living just a short drive from Pittsboro and conveniently located near Chatham Park, shopping, dining, and everyday amenities. Bring your vision—and your animals! Horses and farm animals are allowed, making this an ideal property for those looking to create a private homestead, hobby farm, or peaceful country retreat. Underground power and fiber internet are already available along the property lines, combining rural living with modern-day convenience. A perpetual septic permit adds even more value and helps simplify the path toward building your future home. Residents also enjoy access to a shared neighborhood pond, adding to the natural beauty and relaxed atmosphere of this special property. Build your dream home and an accessory dwelling unit, enjoy room to roam, and experience the best of both worlds—serene country living with Pittsboro and Chatham Park just minutes away.

625 Harts Creek 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 .

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