Pittsboro Homes with Basement

Welcome to Pittsboro, North Carolina – a charming town nestled in the heart of Chatham County, where small-town warmth meets the beauty of nature. Known for its picturesque landscapes and vibrant community, Pittsboro offers a unique blend of rural tranquility and modern convenience. With its rich history and a strong sense of community, this town is the perfect place to call home.

One of the standout features of homes in Pittsboro is the presence of basements, which add a functional and versatile space to your living environment. Whether you envision a cozy family room, a home gym, or a creative workshop, basements provide endless possibilities for customization. The additional square footage allows homeowners to expand their living space, accommodating everything from storage needs to recreation areas.

Pittsboro is not only about beautiful homes; it’s also about the lifestyle. The town is surrounded by stunning natural beauty, with easy access to outdoor activities such as hiking, fishing, and exploring the nearby Jordan Lake. Additionally, the vibrant downtown area is filled with local shops, restaurants, and cultural attractions, fostering a sense of community and connection.

With a growing real estate market, now is the perfect time to explore the homes for sale in Pittsboro. Discover the charm of this delightful town and the added benefits of homes with basements, where you can create the perfect sanctuary tailored to your lifestyle. Experience the best of North Carolina living in Pittsboro, where community, comfort, and creativity come together beautifully!

Newest Pittsboro Homes with Basement

$1,250,000

4 Beds ⋅ 4 Baths ⋅ 10182398 MLS ⋅ ACTIVE Status

Perched atop a scenic hill in Cedar Mountain, this extraordinary custom retreat blends refined mountain-lodge architecture with breathtaking long-range views, exceptional craftsmanship, & thoughtfully designed outdoor living on 2.6 beautifully landscaped acres. A handcrafted stone moongate welcomes you through lush gardens filled with carefully selected plantings that provide year-round color & texture—from vibrant azaleas to yarrow & everything in between. A covered stone front porch with a vaulted cedar ceiling & impressive custom wood entry door sets the tone for the remarkable home within. The stunning great room features soaring vaulted wood ceilings accented by reclaimed pine beams salvaged from a historic 100-year-old local tobacco warehouse. A floor-to-ceiling stone fireplace with a holly wood mantel, creates a warm focal point, while an expansive wall of windows frames panoramic wooded vistas, spectacular sunsets, & the ever-changing beauty of the seasons. The sunroom offers a peaceful retreat with a vaulted cedar ceiling, tiled flooring, and 2 walls of windows that seamlessly connect the living area to the luxurious primary suite. The thoughtfully designed main level also includes 2 primary suites, providing exceptional flexibility for guests or multigenerational living. A dedicated office features custom built-in bookcases, elegant wainscoting, & a stained-glass transom, while a nearby hallway showcases a built-in glass curio cabinet. Designed for both everyday living & entertaining, the gourmet kitchen features rich knotty alder cabinetry, granite countertops, a Thermador 6-burner gas cooktop with pot filler, & a large stainless-steel center island that anchors the beautifully planned workspace. Adjacent to the kitchen, the spacious laundry and mudroom includes a built-in drop zone with bench, cubbies, and a pet door leading to the expansive rear porch. With its vaulted cedar ceiling, reclaimed wide-plank flooring, & dual ceiling fans, this inviting outdoor living area overlooks the breathtaking backyard. Upstairs, you'll find 2 additional bedrooms, a shared bath, a generous loft, & a charming "secret" reading nook sure to delight children & guests alike. A massive unfinished attic offers exceptional expansion potential. Already equipped with lighting, electrical outlets, plumbing for a future bath, and its own electrical panel, the space is ideal for a media room, recreation area, fitness studio, or additional living space. The oversized two-car garage includes a dedicated workshop area, insulated walls, insulated ultra-quiet garage doors, & an EV charging station. Outdoor amenities are truly exceptional. A spacious rear deck, partially shaded by a pergola, captures sweeping views & leads via a beautiful stone staircase to an expansive patio with a built-in fire pit & stone seating—perfect for gathering under the stars. The resort-style heated pool extends the swimming season & is complemented by a stunning pavilion featuring a ceiling fan, rustic built-in cabinetry & countertops, a gas line for grilling, & a dedicated storage room for pool equipment & outdoor gear. Massive stone patios, retaining walls with integrated seating & lighting create a private, peaceful setting unlike any other. Additional highlights include: Custom top-down/bottom-up shades throughout the front of the home, including a remote-controlled kitchen shade. Custom-built chicken coop with protected run. Hobby greenhouse with water service. Irrigation spigots conveniently placed throughout the property for effortless gardening. Dedicated garden area with a gabion stone wall. Extensive custom stonework—including planters, retaining walls, walkways, borders, patios, & outdoor living spaces—crafted primarily from stone harvested directly from the property. Every detail of this remarkable home has been carefully curated to create a private sanctuary where timeless craftsmanship, modern comfort, & unforgettable natural beauty come togethe

1624 Cedar Grove Rd, Pittsboro

$1,173,000

3 Beds ⋅ 3 Baths ⋅ 10182181 MLS ⋅ COMING SOON Status

Nestled on a beautifully landscaped lot of over one acre, this exceptional 3 bedroom, 2.5 bath executive home offers the perfect blend of luxury, comfort, and thoughtful design. From the stunning stone and fiber cement exterior to the impeccably maintained interior, every detail has been carefully crafted for elegant everyday living. The heart of the home is the gourmet cook's kitchen featuring granite countertops, a large center island with dual disposals, natural gas cooktop, built-in oven/microwave combination, Energy Star appliances, and a spacious walk-in pantry. Enjoy casual meals in the charming breakfast area overlooking the lot's wooded and private back yard or entertain guests in the separate formal dining room. Hardwood floors flow throughout the main level, leading into the inviting family room with custom built-in bookshelves and a cozy natural gas log fireplace. A second gas log fireplace enhances the screened porch, complete with custom shades for year-round enjoyment and relaxation. The exquisite owner's suite provides a luxurious retreat with a spa-inspired bath featuring a walk-in shower, soaking tub, and generous space for comfort and privacy. Additional highlights include ceiling fans, Plantation shutters, a convenient main-level utility room, low-flow plumbing fixtures, and a tankless water heater with circulating hot water system. Spacious and versatile, this beautifully designed home offers room for everyone with a thoughtfully finished lower level perfect for multi-generational living, entertaining or guest accommodations. Enjoy a large finished recreation room ideal for movie nights, game days, or a home gym, along with 2 spacious bedrooms and a full bath providing comfort and privacy for family or visitors. The lower level also features access to a huge unfinished storage area with endless possibilities - perfect for a workshop, hobby space, or fitness area. With abundant storage and flexible living spaces throughout, this home combines functionality and comfort in every detail. Outdoor living is equally impressive with a fenced backyard, irrigation system and ample space to enjoy nature's peaceful surroundings. Additional features include a sealed crawlspace, county water, community sewer, durable 30-year shingle roof warranty and natural gas fuel service. Designed by Home by Dickerson with future convenience in mind, the home's construction also incorporates space and options for a potential elevator installation if desired. This remarkable property combines timeless style, energy efficiency, and modern functionality in a serene setting you'll love coming home to.

4200 Henderson Pl, Pittsboro

$450,000

3 Beds ⋅ 2 Baths ⋅ 10181660 MLS ⋅ ACTIVE Status

Beautifully designed contemporary home on a naturally wooded lot in Fearrington Village. Vaulted ceilings, skylights, and abundant windows fill the home with natural light and frame views of the wooded setting. The front door opens to an entry foyer, leading to a living room with a fireplace and a dining area with sliding glass doors to the rear deck. The spacious kitchen includes a pantry and gas stove, with an adjoining laundry room that offers a second pantry. The main-level primary bedroom features a walk-in closet and full bathroom. Upstairs are two additional bedrooms and another full bath. Recent updates include fresh interior paint and new bedroom carpet. Exterior storage closet included.

4 Matchwood, Pittsboro

$789,000

3 Beds ⋅ 4 Baths ⋅ 10181569 MLS ⋅ ACTIVE Status

A Fearrington Village sanctuary in the popular Bush Creek neighborhood with an idyllic garden and .81 acre lot. One-level and spacious, this home features natural light and an ideal floorplan. Wonderful flow from the kitchen with center island to the attached open dining room and living room that leads out to a fantastic all-season room. The lovely woodland creek view from the all-season room evokes the serenity of a mountain retreat. Ample sized primary bedroom and a private guest bedroom which could be a second primary. High ceilings, built-ins and a warm fireplace to gather around in the living room. Two half baths and a large laundry room for your convenience. The lot is landscaped for both beauty and ease and includes an expertly designed patio garden area with smart irrigation. Enjoy the established flora and grow your own in this botanical oasis. A remarkable place to call home in the tranquil, treasured community of Fearrington Village.

804 Millcroft, Pittsboro

$615,000

4 Beds ⋅ 3 Baths ⋅ 10181040 MLS ⋅ ACTIVE Status

From the moment you step through the front door, you'll feel it—this is more than a house; it's a home where love has flourished, laughter has echoed through every room, tiny footsteps became confident strides, and countless memories have been made. Every space tells a story, and now it's ready for its next chapter with you. Beautifully and thoughtfully updated, this exceptional home combines timeless elegance with modern comfort. Rich Bellawood hardwood flooring flows throughout the entire first floor, creating warmth and continuity. The elegant dining room showcases a tray ceiling and classic wainscoting, perfect for hosting holiday dinners and special celebrations. The breathtaking great room welcomes you with soaring vaulted ceilings, custom built-in cabinetry, and a cozy gas-log fireplace with a blower that makes winter evenings especially inviting. The heart of the home—the kitchen—features premium KitchenAid stainless steel appliances and an inviting breakfast nook complete with a custom-built storage bench, creating the perfect place for morning coffee, family breakfasts, or helping with homework. Designed with privacy and comfort in mind, the split-bedroom floor plan offers a peaceful primary suite tucked away from the secondary bedrooms. The luxurious spa-inspired primary bath features a soaking tub, a separate shower with dual shower heads, and even its own dedicated water heater for added convenience. French doors from both the great room and the primary suite open onto an expansive deck, seamlessly blending indoor and outdoor living. Every lighting fixture throughout the home has been meticulously selected and updated, including elegant pendant lighting that gracefully frames the primary bedroom, adding warmth, sophistication, and designer appeal. Step outside, and you'll discover what many have described as a magical private park. This extraordinary backyard is a peaceful sanctuary surrounded by mature trees and beautifully curated landscaping. Relax in the hammock beneath the shade, gather fresh blueberries and blackberries, or stroll among blooming peonies, hydrangeas, and tulips. At its heart is your own tranquil pond with a graceful fountain and a Toro lantern, carefully brought from Japan, creating a setting that feels both serene and unforgettable. Upstairs offers incredible flexibility with an expansive bonus room complete with a closet, generous walk-in attic storage, a dedicated office or flex room, a beautifully remodeled full bathroom, and a spacious fourth bedroom with peaceful views overlooking the neighborhood pond. The location is just as impressive. Jordan Lake is only 10 minutes away, offering endless opportunities for boating, fishing, hiking, and recreation. The future Disney STORYLIVING community will be just five minutes away, bringing exciting new restaurants, shopping, entertainment, and amenities to the area. Families will appreciate the excellent educational options, including highly regarded public schools, Thales Academy, Haw River Christian Academy, Woods Charter School, and Chatham School of Science & Engineering. Every improvement has been made with care. Every room has been loved. Every corner invites you to imagine the memories still waiting to be made. Come experience this impeccable modern home for yourself—and prepare to fall in love.

438 May Farm Rd, Pittsboro

$875,000

3 Beds ⋅ 3 Baths ⋅ 10180964 MLS ⋅ ACTIVE Status

Exceptional custom home offering a fantastic single-level floor plan with a full basement, ideally situated on a private wooded cul-de-sac shared by only three homes in desirable Fearrington Village. Hardwood, parquet, and carpeted flooring combine warmth and character throughout the home.The spacious primary suite features an extraordinary 11' x 11' walk-in closet complete with a custom organization system and center island. The inviting family room is anchored by a fireplace and framed by two full walls of custom built-in cabinetry, providing abundant storage and display space. Designed for both everyday living and entertaining, the expansive kitchen offers a large center island with storage on all sides, extensive cabinetry, and a beautiful furniture-style cabinet featuring glass display doors and a plate rack. A remarkable custom pantry includes wall-to-wall cabinetry with roll-out lower drawers, a full countertop, and an additional sink for exceptional storage and workspace. The well-appointed laundry room is equally impressive with a full wall of upper and lower cabinetry, an organization system, and a utility sink. Enjoy outdoor living on the screened porch and adjoining grilling deck overlooking a peaceful wooded setting that provides exceptional privacy with minimal yard maintenance. The walk-out lower level offers an additional 1,164 square feet of finished space featuring a kitchenette with dining area, flex space, two bedrooms, and a full bath. This finished area was completed without permits and is not included in the home's reported living square footage. The lower level also includes an abundance of unfinished storage, multiple workshop areas, and a utility sink, making it ideal for hobbies, projects, or additional storage. Additional features include a new roof (2025), new water heater (2023), plantation shutters throughout, wide doorways designed for aging in place, and numerous storage closets throughout the home. Fearrington Village is renowned for its vibrant social atmosphere, walking trails, beautiful surroundings, and community amenities. Galloway Ridge Fitness is conveniently located on the adjoining property, offering additional wellness opportunities just steps away.

862 Hatfield, Pittsboro

$2,900,000

4 Beds ⋅ 6 Baths ⋅ 10180014 MLS ⋅ ACTIVE Status

A rare opportunity to build your custom dream home in the sought-after Stonecrest at Norwood community. This lovely proposed custom home features universal design features to help you age in place. Two primary bedroom suites, the ability to add an elevator and more. One of the last remaining estate lots available, this stunning 2.63-acre homesite offers exceptional privacy, accessed by a long, meandering driveway that sets the tone for the retreat that awaits. Picturesque Wilkinson Creek runs along the property, providing tranquil views and soothing natural ambiance. Embrace the natural beauty of the surrounding woods. Stonecrest at Norwood strikes the perfect balance of peaceful, private living with convenient access to surrounding amenities. Community features include scenic walking trails and a beautifully appointed pavilion with a fireplace -- an idyllic setting from the moment you arrive. Other plans available. This lot is also available for private sale without home construction.

93 Kenwood Ln, Pittsboro

$799,000

3 Beds ⋅ 3 Baths ⋅ 10177395 MLS ⋅ ACTIVE Status

Welcome to 316 Ross Drive, where timeless craftsmanship, modern updates, and room to grow come together on a stunning 2.8-acre homesite in one of Pittsboro's most desirable established communities. Offering approximately 2,800 square feet of beautifully maintained living space, this home has been thoughtfully updated and meticulously cared for. Recent improvements include a new HVAC system, updated finishes, and a durable 50-year roof, providing peace of mind for years to come. Inside, you'll find spacious living areas, abundant natural light, and a floor plan designed for both everyday living and entertaining. The updated kitchen and inviting gathering spaces create a warm and welcoming atmosphere, while the generous bedrooms offer comfort and flexibility for family, guests, or home office needs. What truly sets this property apart is its incredible expansion potential. A massive walk-up attic and full walk-out basement provide the opportunity to create substantial additional finished living space tailored to your needs, whether you envision a media room, guest suite, home gym, hobby space, multigenerational living area, or additional bedrooms and baths. Step outside and discover one of the property's most impressive features: a gorgeous 2.8-acre lot offering privacy, mature landscaping, and endless possibilities. The expansive backyard provides ample room for a future swimming pool, outdoor entertaining spaces, gardens, or simply enjoying the peaceful surroundings. Ideally located just minutes from charming downtown Pittsboro, Chatham Park, Jordan Lake, Chapel Hill, and the Research Triangle Park region, this home offers the perfect balance of privacy and convenience. Rarely does a property combine move-in-ready condition, significant future expansion opportunities, and such a beautiful homesite. 316 Ross Drive is more than a home, it's an investment in your lifestyle and your future. Rare opportunity! Seller's existing VA loan may be assumable by qualified buyers, potentially offering significant savings compared to current market interest rates. Assumption subject to lender approval, qualification requirements, and applicable VA guidelines. Contact listing agent for additional details.

316 Ross Dr, Pittsboro

$1,190,000

4 Beds ⋅ 4 Baths ⋅ 10174176 MLS ⋅ ACTIVE Status

This thoughtfully designed 3,505 sqft home features an open and airy layout with 10 ft ceilings on the main level and 9 ft ceilings on the second floor, creating a bright and expansive feel throughout. The home offers 4 spacious bedrooms and 3.5 bathrooms, all secondary bedrooms are en-suite for ultimate comfort and privacy, and the full unfinished basement allows for creativity and possibilities. The chef's kitchen is a true centerpiece, showcasing ceiling-height cabinetry, quartz countertops, stainless steel Bosch appliances, and a 36-inch gas range. A separate scullery kitchen adds both functionality and elegance. The kitchen flows seamlessly into the main living area, highlighted by a 48-inch gas fireplace and large sliding patio doors that open to a backyard with wooded privacy. Additional features include hardwood flooring throughout the main living areas, carpet in the bedrooms, a 3 car garage, and a tankless water heater for efficiency. Located in Chapel Ridge, residents enjoy resort-style amenities including a clubhouse, pool, fitness center, pickleball courts, tennis courts, volleyball, basketball, a soccer field, and of course, championship golf.

79 Lookout Rdg, Pittsboro

$400,000

3 Beds ⋅ 2 Baths ⋅ 10173655 MLS ⋅ ACTIVE Status

Enjoy easy living in this end-unit townhouse set in a park-like setting. The front door opens to a welcoming entry hall. The spacious living room features a vaulted ceiling with skylights and a ceiling fan, a gas fireplace, and large windows overlooking the backyard. A formal dining room connects to the living room. The updated kitchen offers warm wood cabinetry, quartz countertops, and stainless-steel appliances, including a one-year-old stove. A skylight brightens the sunny breakfast area. The main-level primary suite includes three closets, one of them a large walk-in. The adjoining bath features a linen closet, a tile shower with a built-in seat, and a double-sink vanity. Upstairs are two additional bedrooms, a study, and a full bath with skylight and tile flooring. Both bedrooms upstairs have large walk-in closets. Additional living space is available in the sunroom, which has brick flooring and views of the landscaped yard with blooming Rose of Sharon, camellias and azaleas. One-car garage plus assigned parking.

438 Crossvine Close, Pittsboro

$490,000

3 Beds ⋅ 3 Baths ⋅ 10173471 MLS ⋅ ACTIVE Status

Discover the versatility and comfort of this smartly designed home in popular Chatham Forest.with spacious yard and tree buffer behind. Enjoy one level living with open spaces while natural light pours onto gleaming hardwood floors. Plus the perfectly finished lower level; will it be the ideal entertainment area or shall you go with a full media array for the best watch parties? With a bathroom in place, perhaps add a fourth bedroom. Add plenty of storage space along with great location close to downtown and easy access to the highway. It's all here.

512 Chatham Forest Dr, Pittsboro

$400,000

3 Beds ⋅ 2 Baths ⋅ 10171914 MLS ⋅ ACTIVE Status

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

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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 .