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$857,000
3 Beds 3 Baths 10168889 MLS ACTIVE Status
Rustically handsome and rich with character, 205 Anolis offers approximately 2,700 square feet of living space set on 12 remarkable acres in the Redbud community. Tucked at the end of a gravel road, the property unfolds into a beautiful mix of hardwood and pine forest, rolling pasture, and an intermittent stream that feeds into Temple Creek, a tributary of the Haw River. A vernal pool in the lower pasture has even served as a field study site for naturalists from the NC Museum of Natural History, where spring peepers and chorus frogs can be observed in their native habitat. The home itself is a thoughtful blend of craftsmanship and history. The original section, built in 1993, incorporates hand-adzed logs repurposed from three historic barns in Hillsborough, complemented by custom-cut timbers. A 2005 addition seamlessly integrates with the original structure and features flooring, trim, and built-in cabinetry milled on site from solid white and red oak harvested directly from the land. A striking masonry fireplace, built by well known and adored local artisan Joe Kenlan, serves as both a focal point and a highly functional heat source, capable of warming the entire home using wood from the property. Equestrian and outdoor enthusiasts will appreciate the well-planned features, including a horse barn, detached garage, and fenced pasture with Cameo high-tensile horse safety fencing. The riding ring is thoughtfully constructed with a crushed stone base and gravel surface for excellent drainage and year-round usability. The lower portion of the land, known as ''The Nursery,'' was once part of Mellow Marsh Farm, and still retains its terraces and pathways. The property has been maintained without herbicides or pesticides, preserving a healthy and natural environment. Wildlife is abundant, with frequent sightings of songbirds, raptors--including Cooper's Hawks and Barred Owls--wild turkeys, deer, foxes, and more. Black vultures have even returned to nest in the barn, and Eastern Box Turtles and Green Anoles are common sights in warmer months. From Redbud, nearby trails connect to the Haw Slopes Natural Area and the Haw River, offering the rare opportunity to hike for miles--even all the way to Bynum--without crossing a road. Landowners' covenants are in place to preserve the peace, quiet, and natural beauty of the area. 205 Anolis is a truly special property--private, storied, and deeply connected to the surrounding landscape.

205 Anolis Dr, Pittsboro

$1,575,000
4 Beds 6 Baths 10041666 MLS CLOSED Status
Beauteous Buteo. Storybook New England-style cedar-shake estate nestled amidst fairytale gardens & woodlands set in tranquil Redbud. Gated-entry leads to a soothing, meandering gravel driveway through almost 6.5 acres of this quiet hamlet. Cue soundtrack of breeze, birdsong, & a burbling fountain. Enchanting from every angle, the architecture was designed by original owner/church designer Brett Broadwater. Calm pleasure & relaxed charm are assured with neutral palette of natural materials & rarefied attention to detail. With a thoughtful refresh beginning in 2017, this airy & refined blockbuster home has rooms that feel old & new at the same time- familiar yet extraordinary. Wide-plank, southern yellow pine floors harvested & milled from trees on the property; soaring ceilings; hand-cut moldings; custom built-ins; window seats; & bespoke lighting enhance the ambiance. Character-filled wonders roll-on: black walnut newel post in dining area is circa 1841 from Boston (its twin in family room is a replica); a stained-glass window from a Duke Chapel reno illuminates the top of main steps. Staircase handrails, substantial family room fireplace mantel, lower-level bar top, pantry shelves, & laundry room benches are hand-polished walnut. Abundant windows & glass doors brighten & allow the sublime landscape to penetrate the rooms. The epic great room, an infusion of high style & warmth with three sets of double French doors framing sunlight & views, is anchored by a statement, double-sided gas-assist fireplace that can hold four-foot long logs. Craving a kitchen full of flavor-all the ingredients are here with granite tops, eye-catching tile splash, center island, stainless appliances, brick wall, roomy pantry, & fireplace. A meditative, the primary bedroom has a paneled wall & plentiful windows with tree-mendous views. Tranquility reigns in the primary bathroom with soothing tones, a stand-alone-tub, marble shower, cabinet-style vanity, & spacious walk-in closet. Upstairs bedrooms, with en-suite bathrooms & cozy eaves, are a restful retreat. The joie-de-vivre infused layout includes versatile spaces that spark inspiration &/or get the job done such as the front library, main-level serene study/bedroom, multipurpose room above the garage; den/hobby room adjacent to upstairs bedrooms; & fun + functional lower level. With two built-in beer taps; polished live-edge walnut countertop; rope-accented trim on the built-ins & stairs; curved window wall overlooking the gravel patio & fire pit; pool table; & French doors to the great outdoors, the lower level is an at-the-ready play zone, bar none. The kitchen & dining room overlook formal French potager garden with fruits, flowers, vegetables, & herbs (with more than 100lbs of figs having been seasonally produced). Off the garage, find utility with style in laundry/mudroom with brick floor; great natural light; abundant storage; pegs + cubbies; water closet + shower; & door leading to manicured fenced yard with flagstone walkway, idyllic for two-or-four legged little ones. Swoon-worthy, soaring screen porch is a lounging haven with an idyllic setting inside & out. Sky's the limit when it comes to outdoor play space. Unpack & enjoy with the heavy lifting done for you: newer 50-year roof & HVAC systems; exterior trim replaced with fiber cement; enhanced R-38 attic insulation; post-and-beam carport & multi-level deck additions; extensive landscaping & hardscaping including a 130-foot retaining wall, terraced front garden, & custom iron railings. Storage abounds in walk-in attic; lower-level utility space; & under deck/screened porch. Breathing room & proximity are home: in under 15 minutes, enjoy charming downtown Pittsboro; elegant shops & dining at Fearrington Village; beach + boating fun at Jordan Lake. Easy access to Highway 64 & I-540. Jaunt to Apex in ~20 & RDU in ~35 minutes. A magical spot & true refuge, 257 Buteo welcomes you to happily ever after.

257 Buteo Rdg, Pittsboro

$1,125,000
4 Beds 4 Baths 10081007 MLS CLOSED Status
Luxurious Pittsboro Estate with Sustainable Living & Resort-Style Amenities: Welcome to 68 Penna, where timeless elegance meets modern sustainability in a breathtaking private retreat. This sprawling 4,500+ sq. ft. estate is designed for those who crave space, comfort, and connection to nature—all while embracing eco-conscious living. Nestled just five minutes from Jordan Lake and 30 minutes from RDU Airport, this exceptional home offers both seclusion and convenience. Step onto the wraparound front porch and into soaring ceilings that create an expansive, light-filled atmosphere. The main-level primary suite is a true sanctuary, offering privacy and serenity. The home's seamless flow makes it an entertainer's dream, with massive gathering spaces, a gourmet kitchen designed for culinary artistry, and effortless indoor-outdoor living. A true standout feature is its geothermal heating and cooling system, coupled with solar panels, significantly reducing utility costs and making this home as efficient as it is luxurious. The walk-out basement is a world of its own, complete with a second full kitchen, two versatile auxiliary rooms, a sprawling bonus area, and a full bath—perfect for guests, multi-generational living, or an epic entertainment space. Step outside to the covered patio, leading to a fenced, in-ground swimming pool, creating a private oasis for relaxation. For outdoor enthusiasts, this expansive property is a dream come true. Enjoy gardening, composting, hiking trails, and access to a serene community pond. The detached two-car garage includes a bonus room above, offering even more flexibility for work, play, or hosting guests. With abundant storage, soaring ceilings, multiple flex spaces, and cutting-edge sustainability features, this home is an entertainer's paradise and an eco-conscious sanctuary. A rare find that truly offers it all—schedule your private tour today and experience the perfect harmony of luxury and nature!

68 Penna, Pittsboro

$761,000
3 Beds 4 Baths 10109926 MLS CLOSED Status
Custom Craftsman Home tucked away high above the Haw River on 5 private acres in coveted Redbud! Tons of natural lighting help show off the recently updated interior in this 3 bed 4 bath( 3full, 1 half) home located on the east side of the river. Gorgeous wood planked cathedral ceiling, hardwood floors, and real wood trim work details throughout are just a few of the stand out features. Double glass doors lead out to arguably the best deck in all of Chatham County for lounging with family or big time entertaining. Walk from your backyard oasis all the way to the banks of the Haw River for Tubing, kayaking, rock hopping, or even a moonlight stroll- light reflects off the river so you don't need a flashlight! Back at the house, be sure not to miss the the walk out basement with a full bath & oversized laundry room- PLUS an additional 891 sq feet of flex space for your gym space, artist retreat, craftory, etc! After your viewing, don't forget to walk or ride a little further down redbud road to the private neighborhood spring-fed community lake and gathering spot. Picnic spots, play area, and a diving platform for swimming, this property offers an outdoor lifestyle that's hard to match. If you have been seeking a custom built quiet retreat with outdoor adventure at your doorstep- THIS IS IT- Don't miss the chance to own a truly unique property in one of Chatham County's most beloved communities.

767 Redbud, 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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