Refine Search
Map
Sort by
123 Grove Park Cir, Pittsboro
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 10186224 MLS ⋅ PENDING Status
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
4207 Henderson Pl, Pittsboro
$1,025,000
3 Beds ⋅ 3 Baths ⋅ 10200719 MLS ⋅ PENDING Status
Discover this stunning 3-bedroom, 3-bath executive home built by Homes by Dickerson in 2016, offering over 3,000 sq. ft. of living space on a beautifully landscaped one-acre lot. Enjoy an open-concept floor plan with an inviting foyer, crown molding, a gourmet kitchen featuring granite countertops, a large center island, and walk-in pantry. The spacious family room boasts custom built-in bookshelves and a gas fireplace, while a separate formal dining room is perfect for entertaining. The luxurious owner's suite features a spa bath and custom walk-in closet. Additional highlights include a loft-style TV room, screened porch, open deck, plantation shutters, updated lighting, main-level utility room, and a two-car side-entry garage. Enjoy the professionally landscaped backyard with stone pathways, patio, irrigation system, and convenient access to Fearrington Marketplace, restaurants, and shopping. Exceptional extras: Over 2,600 sq. ft. of floored attic space, security system, encapsulated crawl space, tankless water heater, preventive roof protection, and Green Certification. A beautiful blend of space, comfort, and executive-style living in desirable Fearrington Village!

4207 Henderson Pl, Pittsboro
477 Jay Shambley Rd, Pittsboro
$1,000,000
10174112 MLS ⋅ PENDING Status
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
509 Cabin Crk, Pittsboro
$999,999
4 Beds ⋅ 4 Baths ⋅ 10197169 MLS ⋅ PENDING Status
MOTIVATED BUILDER NEEDS TO SELL ASAP TO MOVE ONTO OTHER PROJECTS! OPPORTUNITIES DO NOT COME AROUND LIKE THIS EVERYDAY! REDUCED FROM ORIGINAL PRICE OF $1,200,000 TO UNDER A MILLION! STUNNING NEW CONSTRUCTION CUSTOM HOME IN CHAPEL RIDGE! This beautifully crafted 4-bedroom, 3.5-bath custom home is ideally situated on .53 acres in the highly sought-after Chapel Ridge Golf Community. Thoughtfully designed with exceptional attention to detail, this home offers 2 bedrooms on the main level, including a spectacular Primary Suite with vaulted ceilings and a spa-inspired Primary Bath that is truly a masterpiece. Enjoy a beautifully tiled shower, luxurious soaking tub, dual vanities, and modern lighting. There are 2 electric water heaters to augment getting quick hot water. The impressive walk-in closet features custom built-ins and a huge center island/workspace perfect for folding, organizing, and storing clothing. The second main-level bedroom offers excellent flexibility for guests, an office, or additional living space. 10-foot ceilings on the first floor and 9-foot ceilings upstairs create an expansive and airy atmosphere throughout the home. The massive gourmet kitchen is designed to impress, featuring beautiful quartz countertops, generous counter space, abundant cabinetry, and exceptional storage. The spacious eat-in kitchen flows into a charming kitchen nook/keeping room area, creating the perfect space for casual dining and everyday gatherings. The Family Room provides a warm and inviting atmosphere centered around the fireplace—perfect for relaxing with family and friends. A thoughtfully positioned mudroom provides a practical drop zone for shoes, coats, and everyday essentials, while the main-level laundry room offers additional space for folding and organization. The oversized garage is an incredible bonus and offers room for two large trucks, a golf cart, and a riding mower—ideal for homeowners who need serious storage and workspace. Step outside to enjoy the screened-in porch, perfectly suited for outdoor entertaining and relaxing. The porch leads to a patio ready for grilling and additional outdoor gatherings. The wooded rear setting provides privacy, while the spacious backyard offers room for a future pool. Beyond the property, enjoy the peaceful natural setting with a creek buffer and neighboring cow pasture, creating a beautiful sense of privacy and country charm. Beautifully landscaped with irrigation system and engineered drainage. This exceptional custom-built home combines luxury, functionality, thoughtful design, and incredible outdoor living in one of Chapel Ridge's most desirable golf communities. A truly special home that must be seen to appreciate all it has to offer!

509 Cabin Crk, Pittsboro
251 Gentry Dr, Pittsboro
$998,500
4 Beds ⋅ 4 Baths ⋅ 10118398 MLS ⋅ PENDING Status
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
266 Flatiron Frst Dr, Pittsboro
$988,710
4 Beds ⋅ 5 Baths ⋅ 10195703 MLS ⋅ PENDING Status
This is a presale home listed for comp purposes

266 Flatiron Frst Dr, Pittsboro
4609 Montgomery, Pittsboro
$929,000
3 Beds ⋅ 2 Baths ⋅ 10194512 MLS ⋅ PENDING Status
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
184 Mystic Ln, Pittsboro
$900,000
3 Beds ⋅ 3 Baths ⋅ 10196799 MLS ⋅ PENDING Status
IMMACULATE custom-built modern farmhouse by ICG Homes, beautifully situated on 1.5 acres at the end of a quiet cul-de-sac. From the covered rocking-chair front porch to the expansive screened porch overlooking the treetops, this home is truly special. Beautiful natural wood exposed beams, shiplap accents and engineered hardwoods add warmth and character throughout. The inviting family room features exposed beams and a see-through fireplace shared with the recreation room, creating a wonderful flow for everyday living and entertaining. Light shines through this lovely home. The stunning primary suite is a retreat of its own, featuring exposed beams, a sitting area and magnificent treetop views that create a peaceful, private setting. Two additional generously sized bedrooms plus a versatile loft provide plenty of space for guests, an office or additional living area. The beautifully appointed kitchen features quartz countertops, farmhouse sink, double ovens, gas range and wine cooler. Step outside to the expansive screened porch or grilling patio below and enjoy extensive landscaping, an herb garden, fig tree and fenced yard designed to help keep the deer out. Enclosed Storage under screened porch. Although the property sits on 1.5 acres, the several-acre parcel directly behind it creates an exceptionally private backdrop, making the setting feel like much more acreage. Additional features include a climate-controlled crawl space, well management system and water purification system with reverse osmosis. Whole house surge protector. Enjoy a Pittsboro address and Chatham County taxes with Chapel Hill just minutes away! Ideally positioned between Pittsboro and Chapel Hill, offering convenient access to shopping, dining, recreation and entertainment while still coming home to a peaceful, private setting. Whether enjoying dinner out, shopping, recreation or heading out to watch the game, you'll love having the best of both areas within easy reach.

184 Mystic Ln, Pittsboro
4333 Millcreek Cir, Pittsboro
$849,000
3 Beds ⋅ 3 Baths ⋅ 10194269 MLS ⋅ PENDING Status
Welcome to this rare gem in the highly desirable Fearrington Village community of Pittsboro, NC. This immaculately maintained 3 bed, 2.5 bath single-family home sits on a quiet street, just a short walk from Fearrington Village's shops, restaurants, and amenities. Inside, the home features high ceilings, an open floor plan, and top-quality finishes throughout. With plentiful room to gather both indoors and out, it's an entertainer's dream. Don't miss your chance to join this wonderful community, where walking paths, beautiful landscaping, and social clubs abound!

4333 Millcreek Cir, Pittsboro
2 E Madison, Pittsboro
$825,000
3 Beds ⋅ 3 Baths ⋅ 10185796 MLS ⋅ PENDING Status
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
514 Lavender Hill Rd, Pittsboro
$799,000
10196396 MLS ⋅ PENDING Status
Discover the possibilities with this beautiful 37.5-acre property conveniently located along US Highway 64 West between Pittsboro and Siler City. Offering a blend of open pasture, mature hardwoods, and natural beauty, this property provides an ideal setting for your dream home, multiple resdences or as a land investment. Enjoy breathtaking sunsets, exceptional privacy, and mature trees bordering the property. The established fescue pasture is well suited for horses or cattle, while the abundant wildlife, creeks, and hardwood forests offer excellent opportunities for hunting and outdoor recreation. Much of the groundwork for your future homesite is already in place, with a circular driveway and a four-bedroom septic permit available. A potential pond site adds another opportunity to enhance the property. If you are looking for a land investment this property is directly adjacent to the Bramblewood 60 home single family residential community that has been approved by Chatham County. Schedule your private showing today and experience everything this exceptional property has to offer.

514 Lavender Hill Rd, Pittsboro
210 Lookout Rdg, Pittsboro
$799,000
4 Beds ⋅ 3 Baths ⋅ 10154106 MLS ⋅ PENDING Status
What a stunner! This gorgeous, well-maintained home is located in the desirable Chapel Ridge golf community, just minutes from Chatham Park. The ideal layout features 2 bedrooms and an office on the main floor. A grand entry leads into a light-filled living room that opens to a deluxe kitchen and oversized covered porch--perfect for everyday living and entertaining. Full of character, this home showcases barn doors, shiplap accents, wood mantel and hood cover, and wide-plank barnwood-style RevWood floors. Huge walk-in storage offers excellent potential for future expansion. Sealed crawl space adds peace of mind. Refrigerator, washer, and dryer convey with an acceptable offer. This one won't last!

210 Lookout Rdg, Pittsboro
93 Manns Crossing Dr, Pittsboro
$774,900
3 Beds ⋅ 3 Baths ⋅ 10192894 MLS ⋅ PENDING Status
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
15 W Madison, Pittsboro
$745,000
3 Beds ⋅ 3 Baths ⋅ 10194507 MLS ⋅ PENDING Status
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
450 Ryan Rd, Pittsboro
$725,000
4 Beds ⋅ 3 Baths ⋅ 10191572 MLS ⋅ PENDING Status
Secluded Jordan Lake home, beautifully maintained 1.5-story living on a park-like 3.5 acres with a pool and hot tub. Freshly updated and painted, this exceptional custom-built residence features a gourmet chef's kitchen with a center island, rich hardwood floors, and a stunning stone fireplace that anchors the warm, inviting living space. Enjoy year-round relaxation on the expansive screened porch, the front porch with swing, or meals on the back-dining porch. The spacious primary suite offers direct access to the deck and pool area. With four bedrooms and permits in place for an additional bedroom, the home offers incredible flexibility--including potential for an ADU or multigenerational living. Immaculate condition throughout, with Spectrum fiber, Starlink, and dual-fuel generator. Step outside and experience a true outdoor sanctuary with a fenced vegetable garden and mature perennial irrigated landscaping. Entertain with ease in the resort-style backyard featuring a saltwater inground pool, 8-person hot tub, flagstone patio with fire pit, and a tranquil Koi pond with blooming lotuses. Walk to Jordan Lake on a private trail/easement and enjoy boating, wildlife sightings, hiking trails, and even a nearby bald eagle's nest. Two 24-hour boat/kayak ramps are only 5 minutes away. At the end of a peaceful gravel country road yet located just minutes from downtown Pittsboro and 30 minutes from Chapel Hill and RDU, this one-of-a-kind property offers the perfect blend of tranquil HOA-free rural living with convenient access to dining, shopping, and amenities. Inspection report, repairs/improvements and invoices available.

450 Ryan Rd, Pittsboro
224 Buteo Rdg, Pittsboro
$724,900
3 Beds ⋅ 4 Baths ⋅ 10184986 MLS ⋅ PENDING Status
**Sellers offering $10,000 towards closing costs, buydown or off the price with an acceptable offer** Welcome to a one-of-a-kind Chatham County property offering the space, privacy, character, and updates that are increasingly difficult to find in the Triangle. This home is ideal for buyers who want to stay connected to the Raleigh-Durham-Chapel Hill area while enjoying a quieter setting, more room to spread out, and a home that feels anything but cookie-cutter. Inside, the home has a warm, distinctive personality with architectural details such as wood ceilings, high ceilings, abundant windows, a fireplace, and a loft area that give the interior character that is hard to replicate in newer construction. Natural light is an important part of the home's appeal, with windows that bring in the surrounding wooded views and create an inviting connection between the indoors and outdoors. The home has also undergone significant updates - new flooring throughout, new kitchen cabinets, quartz countertops, stainless-steel appliances, and updated bathrooms. The result is a home that combines rustic character with a fresh, more modern look and feel. The finished daylight walk-out lower level substantially expands the usable living space. This level includes bedrooms, a full bathroom, laundry area, and flex space that could be used for guests, home office, a workout room, media room, hobby space, playroom, or separate living areas for those who appreciate a little more independence. Walk-out access to the backyard also gives the lower level a more open and connected feel than a typical basement. Outdoor living is another standout feature. The home offers approximately 700 square feet of decking on three sides of the property. A fenced portion of the backyard adds even more functionality and can be accessed from both the deck and lower level. Location highlights: Historic downtown Pittsboro, Jordan Lake State Recreation Area, Chatham Park Community, Chapel Hill, Apex, Cary, Durham, Raleigh, and Research Triangle Park are all accessible from this part of Chatham County. The Redbud community has walking trails and the HOA dues include high speed internet!

224 Buteo Rdg, Pittsboro
91 Englehart Ct, Pittsboro
$701,040
3 Beds ⋅ 3 Baths ⋅ 10186835 MLS ⋅ PENDING Status
Encore, Chatham Parks 55+ neighborhood. The Carroway with 1/2 story pre-sale..

91 Englehart Ct, Pittsboro
1379 Bradford Pl, Pittsboro
$699,000
4 Beds ⋅ 3 Baths ⋅ 10179343 MLS ⋅ PENDING Status
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
12 Macon, Pittsboro
$689,000
2 Beds ⋅ 2 Baths ⋅ 10199602 MLS ⋅ PENDING Status
THIS CHARMING HOME welcomes you with a private front courtyard, setting the tone for a space that feels both inviting and beautifully functional. Inside, the flexible dining room space has been transformed into a bright, efficient office with extensive built-ins, creating a perfect work from home set- up. A cheerful sunroom opens onto the courtyard , filling the home with natural light and serving as an ideal dining space. The living room features soaring ceilings and a cozy gas fireplace, flowing seamlessly into the kitchen where a large island, breakfast nook and the convenient pass through with bar sink, could be the coffee bar or cocktail bar. The Primary ensuite offers a walk-in shower and comfortable privacy, while the guest bedroom has convenient access to the hall bath. Through the separate laundry room, you can access the spacious outdoor space, fenced patio with pergola for shade and two gated points of entry, a perfect spot for relaxing outdoors. A 2 car garage, with cooling, lots of storage throughout and a layout that feels bright, open, and easy to live in. Come see it this weekend and experience how bright, welcoming and thoughtfully designed this home truly is. All this is just a short distance from the Village Center, convenient to the park, Belted Goat Cafe and our beloved bookstore....

12 Macon, Pittsboro
89 Englehart Ct, Pittsboro
$630,720
2 Beds ⋅ 2 Baths ⋅ 10197791 MLS ⋅ PENDING Status ⋅ The Sweetfern BLDG.
Welcome to the Sweetfern, a pre-sale in Encore at Chatham Park.

89 Englehart Ct, Pittsboro
416 N Village Pkwy, Pittsboro
$625,000
4 Beds ⋅ 4 Baths ⋅ 10169552 MLS ⋅ PENDING Status ⋅ Pickney BLDG.
BIG BUYER INCENTIVE! Up to $20,000 toward closing costs or financing incentives with preferred lender. Cash buyer incentive also available. Ask onsite for details and restrictions. NEED MORE SPACE? This brand-new Pickney offers an impressive 3,030 sq. ft. with a first floor guest room, finished bonus and bath above the garage. A total of 4 bedrooms, 4 full baths and a 2-car garage in NoVi at Chatham Park. Flexible living spaces provide room for guests, working from home, entertaining or multigenerational living. Enjoy the comfort of new construction, David Weekley Homes warranty coverage and convenient access to the YMCA, trails, parks, MOSAIC and Downtown Pittsboro.

416 N Village Pkwy, Pittsboro
167 Prospect Pl, Pittsboro
$599,900
2 Beds ⋅ 2 Baths ⋅ 10192550 MLS ⋅ PENDING Status
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
39 Englehart Ct, Pittsboro
$599,900
2 Beds ⋅ 2 Baths ⋅ 10187353 MLS ⋅ PENDING Status
Elegance meets everyday comfort in The Carroway, a floor plan designed to make every day feel effortless. At its heart is a glamorous kitchen, anchored by a multi-function island and opening onto sunlit living and dining spaces — perfect for cooking, entertaining, or simply gathering together. The Owner's Retreat offers a true escape, featuring an en suite bathroom and spacious walk-in closet for a private, restorative haven. A well-appointed guest room with its own bathroom ensures visitors enjoy comfort and privacy of their own. Step outside to the covered porch, an inviting extension of the home ideal for quiet evenings or lively gatherings with friends and family.

39 Englehart Ct, Pittsboro
396 N Village Pkwy, Pittsboro
$575,000
4 Beds ⋅ 3 Baths ⋅ 10159701 MLS ⋅ PENDING Status ⋅ 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
250 Hamamelis Ln, Pittsboro
$565,000
2 Beds ⋅ 2 Baths ⋅ 10197827 MLS ⋅ PENDING Status
An ENCHANTING oasis that inspires imagination, oneness with nature and serenity. This former artist's home is set beautifully on over 7 acres with direct access (and ownership) to the community lake. Redbud, a unique neighborhood that prides itself on a common respect for the environment, is 30 minutes from Chapel Hill and 15 minutes from downtown Pittsboro. As you drive into Redbud and pass the pristine community lake turn onto Hamamelis and feel like you've transported to a mountain retreat. The home is perched perfectly past the circular driveway, waiting for your arrival. Take the meandering stone path to the screened front porch. The main level features a soaring ceiling with huge windows letting natural light dance off the walls and the gorgeous refinished hardwood floors. Living and dining are combined with walls of windows and a wood burning fireplace. An office or small bedroom, full bath and studio/bedroom/flex room are also on the main level. The former art studio is staged as a potential main level primary bedroom or guest space. It is perced for 2 bedrooms with many possibilities for how to use the rooms in this home be it for work, play or meditation. Upstairs you'll find a large bonus room, another full bathroom with a garden tub surrounded by windows overlooking the vegetable garden area and yard. On the other side of the hall is another bedroom plus a sweet terrace overlooking the deck below and, of course, the expanse of rolling woods that make up this incredible lot. There's a custom built shed that's a work of art in itself plus another shed giving you lots of storage and workspace. The woods slope down along the creek inviting you to walk to the community lake for a picnic or perhaps to pick up a book in the community book box. 250 Hamamelis feels like home, where you fall asleep to the sounds of the cicadas and wake up to sip your coffee by the fireplace with full view of the majestic hardwoods and all their splendor. High speed internet through the HOA makes working from home feel like working from heaven. The sellers have provided a brand new Kinetico water filtration system, septic already pumped, refinished hardwoods, new carpet, fresh paint inside and out and a chance to own a home of your dreams.

250 Hamamelis Ln, Pittsboro
216 Tantara Bnd, Pittsboro
$540,230
2 Beds ⋅ 2 Baths ⋅ 10186885 MLS ⋅ PENDING Status
Nestled in Encore, Chatham Parks 55+ neighborhood. The Clarity. Pre-Sale.

216 Tantara Bnd, Pittsboro
136 Windsong Dr, Pittsboro
$539,000
3 Beds ⋅ 4 Baths ⋅ 10176384 MLS ⋅ PENDING Status
*$7,000 PAINT CREDIT + 1 YEAR HOME WARRANTY* Welcome to exceptional living in sought-after Potterstone Village, where comfort, style, and convenience come together just minutes from vibrant downtown Pittsboro and the exciting growth of Chatham Park. This beautiful home offers the ease of main-level living paired with versatile spaces for entertaining, working, and relaxing. Hardwood floors, elegant architectural details, and abundant natural light create a warm and inviting atmosphere throughout. The open kitchen features granite countertops, a tile backsplash, stainless steel appliances, and seamless access to the butler's pantry and dining room featuring decorative wainscoting, crown molding and coffered ceiling. You're sure to enjoy the enclosed sun porch, multi-level deck, and private fenced backyard—perfect for gatherings or peaceful evenings outdoors. The first-floor master suite serves as a private retreat with a tray ceiling, spa-like bath, and spacious walk-in closet. Upstairs, you'll find two additional bedrooms, a generous loft area, a large bonus room ideal for home entertainment or recreation space, and extensive walk-in attic storage. Complete with a covered front porch, two-car garage, and access to neighborhood amenities including a clubhouse, pool, pond and hiking trails this move-in-ready home offers the perfect blend of refined living, everyday comfort, and investment in one of Pittsboro's most desirable communities. Easy commuting to Pittsboro's surrounding areas including Sanford, Chapel Hill, Raleigh & Chatham Co.

136 Windsong Dr, Pittsboro
226 Beacon Dr, Pittsboro
$525,650
3 Beds ⋅ 3 Baths ⋅ 10041063 MLS ⋅ PENDING Status
Feeling Lucky?? You will feel as if you have won the lottery when you enter this home - huge open floor plan on the main level - you choose the options you want to personalize the home to your lifestyle. Huge loft on the second floor for casual entertaining. Primary bedroom has 2 walk-in closets. 2 additional bedrooms share a large bath. This home is to be built - you choose your options! Check out the private backyard and don't forget to ask us about our Use-as-You-Choose Incentive!!

226 Beacon Dr, Pittsboro
37 Tallgrass Rd, Pittsboro
$518,910
4 Beds ⋅ 3 Baths ⋅ 10167538 MLS ⋅ PENDING Status ⋅ Haddington BLDG.
For comp purposes only

37 Tallgrass Rd, Pittsboro
65 Hillway Rd, Pittsboro
$510,430
4 Beds ⋅ 3 Baths ⋅ 10188122 MLS ⋅ PENDING Status ⋅ Haddington BLDG.
Pending home for comp purposes only.

65 Hillway Rd, Pittsboro

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 .

How much is your home worth?

Get instant property value now!