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123 Grove Park Cir, Pittsboro
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 10186224 MLS
PRIVATE 1.5-ACRE RETREAT MINUTES FROM CHAPEL HILL! Stunning custom brick home on a beautifully landscaped, gated homesite with fenced grounds and a peaceful water feature with waterfalls. Designed for main-level living with wide doorways, walk-in shower, open floor plan and abundant natural light. Vaulted living room, spacious primary suite, private study with built-ins, huge kitchen island and oversized walk-through pantry/scullery. Screened porch overlooks the private wooded backyard. Upstairs offers spacious bedrooms plus a large unfinished area with potential for a second primary suite or bonus space. Expansive unfinished basement provides even more room to grow, with space currently used as a home gym. Convenient to Chapel Hill, UNC, UNC Health, downtown Pittsboro, Chatham Park, Fearrington Village and Jordan Lake. Privacy, space and possibilities—this one is a must-see!

123 Grove Park Cir, Pittsboro

51 Bynum Rd, Pittsboro
$1,000,000
3 Beds ⋅ 3 Baths ⋅ 10193586 MLS
This is truly one of the most unique and beautiful properties in the area. The expansive property consists of over eight acres and includes a main home, a guest cottage, a three-bay garage with an RV/boat bay, a workshop with an additional garage bay, and a potting shed. This location is convenient to Pittsboro and Chapel Hill. Main travel routes are a short distance away. The setting is private and the home is surrounded by trees and established landscaping. Its gardens, which can be enjoyed from multiple decks and patios, are filled with flower beds, stone pathways, and garden walls. Inside the main home the open floorplan is perfect for entertaining or time spent with family. The windows and soaring ceilings are an incredible experience and natural light is abundant. Many upgrades are found throughout the home. Surfaces and features have been designed to be both functional and beautiful. There are many options to display artwork and collectables. Entrance to the home is through a lovely porch with Asian inspired detailing and an ample foyer leading to the living room. The living room has large windows spanning much of one wall. These windows look out on the garden and patios. This space is both inspiring and relaxing. The living room is anchored by one of the home's two fireplaces. The fireplace is stone and masonry and has significantly sized gas logs. Built-in shelving completes the space. A den adjoins the living room and looks out over the woodland setting. The larger of the homes two decks is accessed through the den. A dining area shares the space with the living room and den. Off the living room is an office with built-in shelving. The kitchen is spacious with ample cabinetry and counter space. A butler's pantry, with sink, is across the hall from the kitchen. Wood ceilings are found in the living room, dining area, and kitchen. The opposite end of the home is the generously sized primary bedroom suite with large windows, two large walk-in closets, a seating area with built-in cabinetry, the home's second gas fireplace, access to the home's second deck, and an en suite bath. This bath has a shower, dual sink vanity, and water closet. There is an additional bedroom and another full bath in the main home. A sink, cabinets for storage, and a folding area are located in the laundry room. Across the lawn from the main home is the guest or in-law cottage. This is a completely separate home and includes a living room, full kitchen, full bath, a large bedroom with seating area, a storage room, large walk-in cedar closet, and a deck. Two additional buildings are located near the guest cottage. One building is a workshop with garage bay to store lawnmowers, a tractor, or a small car. A potting shed is found on the other side of the workshop. The three bay garage includes one bay that could house a RV or boat. Additional features of the main home include pull out drawers in the kitchen, butler's pantry, and primary bedroom cabinetry, metal and membrane roofing, heated flooring in some areas of the home, a generator, and smart thermostats. The crawlspaces of both the main house and guest cottage have been encapsulated. Separate meters for electric and gas are found on the guest and main homes. This home has an exceptional floorplan, has space for entertaining both large and small groups and is located close to all that Pittsboro and Chapel Hill have to offer while still feeling private and secluded.

51 Bynum Rd, Pittsboro

477 Jay Shambley Rd, Pittsboro
$1,000,000
10174112 MLS
Rare opportunity to own a beautiful acreage tract with rolling topography, mature hardwoods, and exceptional potential. This unrestricted property offers extensive pasture areas, public road frontage, and a private setting ideal for a custom estate, family compound, mini-farm, recreational retreat, or future development. Bring your own builder and build on your timeline—there is no time limit to begin construction. Multiple potential homesites and favorable soil maps provide flexibility for a variety of uses. The property may be suitable for subdivision or a small residential development, subject to buyer verification and approvals. An intermittent stream enhances the natural character of the land, while easement access via Friendly Pooch Lane provides additional access to the rear portion of the tract. Enjoy the freedom, privacy, and flexibility that come with owning unrestricted acreage with endless possibilities.

477 Jay Shambley Rd, Pittsboro

251 Gentry Dr, Pittsboro
$998,500
4 Beds ⋅ 4 Baths ⋅ 10118398 MLS
Discover luxury living just minutes from Jordan Lake. 251 Gentry Drive offers a rare blend of elegance, privacy, and proximity — where boating mornings, Apex afternoons, and peaceful Pittsboro sunsets are all within reach. Divine- a home that feels both luxurious and livable.......Welcome to 251 Gentry Drive in Pennington at Jordan Lake — where elegance meets everyday comfort in a community known for friendly neighbors, big skies, and quick access to everything. Eco Select and Global Luxury. This 4 bedroom, 4 bath, 3,457 sq ft residence pairs thoughtful design with impeccable finishes, creating a sanctuary for both daily living and elegant entertaining. Upon entry, the home reveals its elevated character: 10-foot ceilings, intricate wainscoting, designer tilework, and fine millwork that speak to custom artistry. The chef's kitchen is a showpiece designed to impress. Featuring Vanato Extra quartz countertops, custom white full-overlay cabinets with crown trim, under-cabinet lighting, soft-close doors and drawers, farmhouse sink plus prep sink, recessed and designer lighting, and a massive center island with breakfast bar, this kitchen balances style and function. The living room is both inviting and impressive, anchored by a floor-to-ceiling stacked stone gas fireplace with custom mantle and raised stone hearth. The screened porch is a beloved masterpiece with beadboard ceiling and Trex flooring, creating seamless indoor-outdoor flow. Main-level living is perfected with a spa-inspired primary suite offering gorgeous hardwood flooring, shiplap accent wall, custom reading lights, and an oversized walk-in closet with custom shelving. The luxurious primary bath includes dual quartz vanities, a freestanding soaking tub beneath double windows, and a walk-in shower with mosaic tile accents, hand shower, and linen closet. Also on the main floor: a guest suite with full bath and open dining/flex room that adapts to your lifestyle. Upstairs, enjoy a massive rec/bonus room, additional guest bedrooms, and abundant finished storage. Every element was thoughtfully curated, from the sealed crawlspace and tankless water heater to the three-car garage and water filtration system. Outdoors, the .92-acre lot provides both beauty and possibility. The backyard, framed by mature trees, offers privacy and space to design your dream retreat — whether that's a gazebo, firepit, playset, sports net, or outdoor kitchen. Thoughtful landscaping enhances curb appeal while maximizing usable green space. The location is unbeatable. Only 0.4 miles to Seaforth High School, and minutes to Downtown Apex, Brier Creek, Costco, Chatham Park, and Downtown Pittsboro. Jordan Lake and the Seaforth boat ramp are less than 3 miles away, with RDU, RTP, and Chapel Hill all within 25 minutes. In a neighborhood where million-dollar homes consistently sell quickly, this property delivers both extraordinary value and timeless design. 251 Gentry Drive isn't just a home — it's a lifestyle. Schedule your private showing today and experience the perfect blend of luxury, comfort, and connection.

251 Gentry Dr, Pittsboro

4609 Montgomery, Pittsboro
$929,000
3 Beds ⋅ 2 Baths ⋅ 10194512 MLS
ROOM TO BREATHE. ONE LEVEL LIVING. ZERO STEP ENTRY FROM GARAGE! Tucked farther back from the road in one of Fearrington Village's newest sections, this 2800+ sq.ft home offers an unusual combination of space, privacy and easy one level living. This home feels open and comfortable without sacrificing those things that make daily life easier. There is generous storage throughout, a sunroom with oversized pocket doors that allow you to define or open the space and remote controlled shades on practically every window. Step outside to the open deck and view the changes to the trees and a peaceful backdrop. It's a home that gives plenty of of room to live while still feeling connected to the natural setting that makes Fearrington so special. Additional features: Oversized gutters with Leaf Guard gutter guards - remote controlled shades on most windows

4609 Montgomery, Pittsboro

2 E Madison, Pittsboro
$825,000
3 Beds ⋅ 3 Baths ⋅ 10185796 MLS
This exceptional home in Fearrington Village's Camdens neighborhood sits on a beautifully landscaped corner lot just steps from the weekly farmers' market, bookstore, shops, coffee, and dining in the Village center. An inviting foyer opens to a spacious living room with high ceilings, large windows, a fireplace, and a formal dining area. The living area flows into the kitchen and family room, where French doors open to a private courtyard garden. The remodeled kitchen features custom cabinetry, a tile backsplash, an island, marble countertops, and a breakfast area overlooking the courtyard, while the adjoining butler's pantry offers added storage. The main-level primary suite includes a bay-window sitting area, large walk-in closet, and luxurious bath with an oversized tile shower, generous double vanity with marble countertops, and transom windows. A laundry room and half bath are also on the main level. Upstairs, two spacious bedrooms with ample closet space share a full bath and loft/flex area. The customized garage, accessed from a private alley behind the home, includes a utility sink, epoxy flooring, and excellent storage. Outdoors, the private brick courtyard offers an inviting place to relax. Professionally landscaped grounds include a rear herb garden and front shade garden with unique ferns, shrubs, and trees, all supported by irrigation systems.

2 E Madison, Pittsboro

93 Manns Crossing Dr, Pittsboro
$774,900
3 Beds ⋅ 3 Baths ⋅ 10192894 MLS
Welcome to 93 Mann's Crossing Dr! This Well Appointed and Superbly Maintained Home has all the Fit and Finish you expect! Freshly Painted Inside and Out and Featuring a Sealed Crawlspace, with the 1st Floor HVAC, Pool Liner and Water Heater all Replaced in 2026. This Home is More than Move-in-Ready, it is Like New!! Interior Features include: Real Site Finished Hardwood Flooring, A Main Level Primary Bedroom, Built-in Cabinetry adjoining the Family Room Fireplace, SS Appliances and a Fabulous Flex/Craft Area. The Enclosed Eze-Breeze Porch is Ready for Your Enjoyment Year-Round and Overlooks a Large and Tranquil Back Yard featuring a Fully Fenced In-Ground Pool. All you need to Enjoy Living in this Beautiful Home and all within 15 Minutes of Chapel Hill and Convenient to All Points in the Greater Triangle Area.

93 Manns Crossing Dr, Pittsboro

56 Mist Wood Ct, Pittsboro
$760,000
4 Beds ⋅ 4 Baths ⋅ 10182780 MLS
Come take a look at this charming custom built home located in the highly desirable Chapel Ridge Golf Club neighborhood. Perched on a hill at the end of a secluded cul-de-sac, this beautifully designed home is thoughtfully built. The spacious kitchen, traditional powder room, hardwood floors, and French doors leading to the backyard give ample opportunity for your hosting dreams. Not one but two suites located on the main floor give multiple easily accessible options. Upstairs you will find two bedrooms, a large bathroom, flex space and a walk-in attic that could easily be converted into a gym or theater. Step outside on the large lanai with additional patio and market lights ready for family nights under the stars. Venturing out into the neighborhood amenities, you'll find resort style living with an oversized pool, owner's clubhouse, complete gym, tennis and pickleball courts, and an optional golf membership at the Fred Couples designed course! Home is broker owned. Local lender credit available!

56 Mist Wood Ct, Pittsboro

15 W Madison, Pittsboro
$745,000
3 Beds ⋅ 3 Baths ⋅ 10194507 MLS
CHARMING CURB APPEAL MEETS COMFORTABLE, easy living at 15 West Madison. This beautifully maintained home stands out with one of the neighborhoods few front flower beds and a classic white picket fence, creating an inviting first impression. Step inside a thoughtfully designed home with two fireplaces, abundant storage and a generously sized laundry room, features that make everyday living both comfortable and convenient. The great courtyard offers a wonderful private outdoor space for relaxing or entertaining. Inside, the spacious rooms and generous windows provide plenty of natural light, while the homes abundant storage makes it easy to keep everything organized. Recent improvements add even more appeal. New roof and gutters 2021, new TRANE systems 2022, new water heater and piping 2025. Additional updates include living room and den shades and new wrought front entrance iron rail. Come see why 15 West Madison is such a special place to call home, the curb appeal will draw you in and the thoughtful features and updates will make you want to stay.

15 W Madison, Pittsboro

686 Spindlewood, Pittsboro
$735,000
3 Beds ⋅ 2 Baths ⋅ 10185946 MLS
MOVE IN READY HOME! LIST OF UPDATES AVAILABLE. A Private, Modern Retreat backing to 247 Acres of Forever Protected Woods. Some homes feel tucked away, this one feels like a world of it's own. Set on a private homesite and backing directly to 247 acres of permanently protected Triangle Land Conservancy land, this updated one-level home delivers the kind of wooded view you simply cannot replicate and will never lose. Step into the tree-top deck and you're surrounded by quiet, filtered light, and the sense that nature is part of your everyday life. Inside, the home is bright, open and move-in ready: 3 Bedrooms, 2 updated baths, fresh paint, smooth ceilings, new skylights, and a long list of improvements that have been thoughtfully documented for buyers who appreciate quality. The layout lives comfortably and efficiently, with natural light pouring in from every angle. A standout bonus: the oversized garage with its own mini-split system, giving you a heated and cooled flex space for hobbies, workouts, storage, or the workshop you've always wanted. And while the setting feels private, you're still in the heart of the community everyone loves. Here, you are minutes from: Our Village Center with restaurants, the greatest independent bookstore, and a weekend pub with live music. Walking trails and paths that weave through the neighborhood. The park and lake, perfect for morning walks or sunset strolls. And of course, our iconic Belted Cows and Goats that make this place feel like nowhere else . It's the kind of neighborhood where you truly have everything you need and never feel the need to leave. A modern, move-in ready home. A forever wooded backdrop. A community with a heart. This is the lifestyle buyers are searching for and it's waiting right here.

686 Spindlewood, Pittsboro

4127 The Knolls Cl, Pittsboro
$700,000
3 Beds ⋅ 2 Baths ⋅ 10188676 MLS
"Nature is not a place to visit, it is home." Set within the picturesque, walkable community of Fearrington Village, 4127 The Knolls Close embodies the serenity, charm, and timeless appeal of Carolina living. Tucked along a quiet street framed by mature trees and beautifully maintained landscapes, this welcoming residence offers an ideal setting for relaxed everyday living and effortless entertaining. Inside, a bright and thoughtfully designed one level layout lives comfortably and intuitively. Generous windows fill each room with natural light, creating warm, inviting spaces perfect for morning coffee, quiet reading, or gathering with friends. The main living area flows seamlessly into the dining and kitchen spaces, giving the home an easy, open feel. The spacious family room features tall ceilings, built ins, and a fireplace—an ideal backdrop for cozy evenings. The large kitchen will delight any cook with abundant cabinetry, ample workspace, granite counters, and stainless steel appliances. The well appointed primary suite offers a generous walk in closet and a beautifully updated bath with an expansive tiled shower. Two additional bedrooms provide flexibility for guests, hobbies, or a home office. Outdoor living is a highlight: a private screened porch overlooking lush greenery, plus a charming courtyard patio and garden that extend the home's peaceful ambiance. This homesite is borders dedicated greenspace. Life in Fearrington Village is truly unique—tree lined paths, friendly neighbors, and beloved amenities including the Fearrington House Inn & Restaurant, The Belted Goat, boutique shops, walking trails, and year round community events. All just minutes from Chapel Hill, Pittsboro, and Jordan Lake.

4127 The Knolls Cl, Pittsboro

1379 Bradford Pl, Pittsboro
$699,000
4 Beds ⋅ 3 Baths ⋅ 10179343 MLS
Tucked away on a cul-de-sac backing to undeveloped land, this beautiful one-level home in.the Bradford Place neighborhood within Fearrington Village offers the perfect combination of comfort, flexibility, and peaceful surroundings. Freshly painted throughout with brand-new carpet as well! The light-filled interior features an inviting, open layout with vaulted ceilings and skylights, custom built-ins, and a fireplace that creates a warm gathering space for family and friends. Large windows frame serene views of the natural landscape, bringing the outdoors inside. A standout feature is the detached guest cottage, offering exceptional versatility for visiting family and friends, a private home office, art studio, fitness space, or hobby room. The spacious primary suite provides a relaxing retreat, while additional living spaces offer room to spread out and entertain with ease. Step outside to enjoy the quiet setting and privacy of a backyard that borders undeveloped land, creating a peaceful backdrop that's increasingly hard to find. The front features a private courtyard. You'll enjoy easy access to walking trails, parks, shops, restaurants, and all the charm this award-winning community has to offer, while remaining just minutes from Pittsboro, Chapel Hill, and the greater Triangle. Flexible living spaces, and an exceptional setting make this a rare opportunity in one of Chatham County's most sought-after communities. Come take a look today.

1379 Bradford Pl, Pittsboro

167 Prospect Pl, Pittsboro
$599,900
2 Beds ⋅ 2 Baths ⋅ 10192550 MLS
ROSEBAY MODEL HOME OPPORTUNITY | Leaseback Option Available. Please call listing agents for more information on terms of sale. Welcome to the Rosebay by David Weekley Homes in award-winning Encore at Chatham Park! This exceptional model home opportunity offers the rare chance to own a professionally designed home with an impressive collection of upgrades and finishes. The thoughtfully designed Rosebay features a gourmet kitchen with gas cooktop, an open concept study, spacious roll-in shower in the Owner's Bath, tray ceilings in the Owner's Retreat and dining room, and expansive 8-foot sliding glass doors leading to the covered rear porch with a lovely view. Enjoy exceptional design, quality craftsmanship, and the lifestyle of Encore at Chatham Park. Don't miss your opportunity to make the Rosebay your new home!

167 Prospect Pl, Pittsboro

18 Candlelit Way, Pittsboro
$576,000
2 Beds ⋅ 2 Baths ⋅ 10188798 MLS
Discover the timeless appeal of The Mosley by David Weekley Homes, thoughtfully designed for comfortable, stylish living in the 55+ community of Encore at Chatham Park in Pittsboro, NC. An open and inviting layout brings the sunny family room and dining area together, creating an ideal space for entertaining, relaxing, and enjoying everyday life. At the heart of the home, the well-appointed kitchen offers a beautiful setting for preparing everything from casual meals to holiday gatherings. The welcoming front porch provides an inviting space to greet neighbors, while the flexible study offers the perfect opportunity for a home office, hobby room, or creative space. A comfortable secondary bedroom provides privacy and convenience for overnight guests. At the end of the day, retreat to the spacious Owner's Suite, featuring a contemporary en-suite bath and generous walk-in closet. With thoughtful design, versatile living spaces, and the lifestyle amenities of Encore at Chatham Park, The Mosley offers an exceptional opportunity to enjoy the best of low-maintenance 55+ living. Built by David Weekley Homes, this home combines quality craftsmanship with award-winning customer service in one of Pittsboro's most exciting communities. Discover the timeless appeal of The Mosley by David Weekley Homes, thoughtfully designed for comfortable, stylish living in the 55+ community of Encore at Chatham Park in Pittsboro, NC. An open and inviting layout brings the sunny family room and dining area together, creating an ideal space for entertaining, relaxing, and enjoying everyday life. At the heart of the home, the well-appointed kitchen offers a beautiful setting for preparing everything from casual meals to holiday gatherings. The welcoming front porch provides an inviting space to greet neighbors, while the flexible study offers the perfect opportunity for a home office, hobby room, or creative space. A comfortable secondary bedroom provides privacy and convenience for overnight guests. At the end of the day, retreat to the spacious Owner's Suite, featuring a contemporary en-suite bath and generous walk-in closet. With thoughtful design, versatile living spaces, and the lifestyle amenities of Encore at Chatham Park, The Mosley offers an exceptional opportunity to enjoy the best of low-maintenance 55+ living. Built by David Weekley Homes, this home combines quality craftsmanship with award-winning customer service in one of Pittsboro's most exciting communities.

18 Candlelit Way, Pittsboro

396 N Village Pkwy, Pittsboro
$575,000
4 Beds ⋅ 3 Baths ⋅ 10159701 MLS ⋅ Pickney BLDG.
Thoughtfully designed with an emphasis on craftsmanship and livability, the Pickney plan by David Weekley Homes offers open sight lines and an easy, natural flow through the kitchen, dining, and family room, making everyday living and entertaining feel effortless. At the heart of the home, the kitchen blends style and function while maintaining connection to the main living spaces. A front study with views of the welcoming porch provides the flexibility to serve as a home office, creative space, or quiet retreat. This four bedroom, three full bath home includes a private guest bedroom on the first floor, ideal for visitors or multigenerational living. Upstairs, junior bedrooms and additional gathering space create room for growing households to spread out and relax. The Owner's Retreat is a peaceful escape, featuring a spacious bath and an oversized walk in closet designed to elevate daily routines. With flexible spaces, smart design, and comfortable separation of living areas, the Pickney plan offers both functionality and timeless appeal.

396 N Village Pkwy, Pittsboro

37 Millennium, Pittsboro
$554,000
3 Beds ⋅ 3 Baths ⋅ 10170599 MLS
Welcome home to this beautifully maintained, like-new gem nestled in one of the area's most thoughtfully planned communities. Perfectly positioned just steps from exceptional neighborhood amenities, this charming two-level home combines comfort, convenience, and timeless style. Inside, you'll find an inviting open-concept layout designed for everyday living and effortless entertaining. The main-floor primary retreat offers privacy and ease, while the gorgeous kitchen, spacious walk-in pantry, functional mud room, and attached garage add practical touches throughout. Enjoy quiet mornings or relaxing evenings on the screened porch overlooking the peaceful surroundings. Meticulously cared for and truly move-in ready, this home features three spacious bedrooms plus a versatile second-floor bonus room that could easily serve as a fourth bedroom, home office, or playroom. With two and a half bathrooms and flexible living spaces, there's room for everyone to feel at home. Beyond the front door, residents enjoy access to an incredible lifestyle-centered community featuring miles of scenic walking trails, playgrounds, dog parks, pickleball courts, and a swim club -- available through additional membership. This is more than a home -- it's a lifestyle in a community designed to connect, relax, and thrive.

37 Millennium, 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 .