Chestnut Hills Real Estate

Welcome to the picturesque subdivision of Chestnut Hills located in the heart of North Carolina, US. Nestled in the charming state of NC, Chestnut Hills offers a serene and welcoming community for those seeking a peaceful place to call home.

Chestnut Hills is known for its beautiful tree-lined streets, well-maintained homes, and close-knit atmosphere. Residents here enjoy the best of both worlds - a tranquil suburban setting with easy access to urban amenities. The neighborhood is perfect for families, young professionals, and retirees alike, with a variety of housing options to suit different needs and preferences.

Living in Chestnut Hills means being part of a vibrant community where neighbors become friends and every street feels like home. The area boasts top-rated schools, lush green spaces, and convenient proximity to shopping, dining, and entertainment options. Whether you're looking to relax in the comfort of your own backyard or explore the great outdoors, Chestnut Hills has something for everyone.

Come and experience the laid-back lifestyle and warm hospitality of Chestnut Hills. Discover your dream home in this idyllic subdivision and make lasting memories in a place you'll be proud to call your own. Welcome home to Chestnut Hills - where community and comfort meet.

Newest Listings in Chestnut Hills

$360,000

2 Beds ⋅ 1 Baths ⋅ 4420243 MLS

Welcome to **Shady Grove Cottage at Chestnut Hills**, a charming mountain retreat, c. 1922, in beautiful Gerton, NC. Tucked just over the mountain from Asheville and minutes from the picturesque villages of Chimney Rock and Lake Lure, this lovingly cared-for cottage offers a wonderful blend of history, character, and mountain charm. Shady Grove is believed to be the first cottage in the Chestnut Hills neighborhood. Many of the homes throughout Chestnut Hills carry a rich history, adding to the unique sense of place found here. Tax records have this home as 1940, but the local lore is the home is most likely from the 1920's. The cottage offers 813 square feet of main-level living, plus a unique sleeping loft with ladder access—perfect for adventurous guests and overflow sleeping space. Outdoor enthusiasts will appreciate direct access to nearby adventure, including hiking to Bearwallow Mountain and on to Strawberry Gap right from your door, plus a short drive to multiple trailheads featuring waterfalls, mountain streams, and sweeping 360-degree mountain views on Bearwallow Mtn. Everyday living here feels like a getaway. Enjoy morning coffee from the covered front porch while taking in beautiful lake views & close range mountain views, cozy winter mornings beside the old stone fireplace, or relaxing evenings on the screened back porch overlooking the fish pond and mature landscaping. In the early evening, settle onto the front porch and listen as church bells echo through the valley at 6 p.m.—a wonderfully peaceful way to end the day. Inside and out, Shady Grove is filled with thoughtful details and timeless character, including soapstone countertops, a farmhouse sink, walk-in tiled shower, vaulted ceilings with bead board walls, and corner windows that capture expansive lake and nature views. Outside, vintage boxwoods frame the front yard, while original stone walls, steps, and patios complete the vintage aesthetic. A sweet back yard with a fire pit creates inviting spaces for gathering and enjoying the mountain setting. **What this cottage may lack in square footage, it more than makes up for in charm, character, history, and setting.** Whether you're searching for a full-time residence, a second home, or an investment opportunity, Shady Grove is a special mountain escape you won't want to miss. Studio/office was originally the 2nd bedroom, but seller moved that to the loft to have an art studio. Could again become a bedroom. https://youtu.be/B96q4Nd7gCA

95 Chestnut Hill Loop Road, Gerton

$4,250,000

5 Beds ⋅ 6 Baths ⋅ 10184474 MLS

Exceptional presale opportunity with award-winning Exeter Building Company in coveted Chestnut Hills—in the heart of North Hills-Midtown. Enjoy effortless walkability to the North Hills Club while collaborating with Exeter Building Company, one of Raleigh's premier award-winning custom builders to design and craft your dream home in one of the city's most desirable locations.

842 Manchester Dr, Raleigh

$535,000

3 Beds ⋅ 2 Baths ⋅ 4387825 MLS

Step back in time without sacrificing modern comfort in this beautifully renovated 1920s Chestnut Hill cottage. The home showcases timeless mountain-cottage charm, highlighted by a grand stone fireplace and inviting covered front porch that harken to the days of the leaving the city heat to spend the whole summer in the cool mountains, playing in the community creak or fishing on the community lake. Thoughtful renovations preserve the home's historic character while enhancing everyday livability. Relax on the expansive covered front porch and enjoy cozy short-range mountain views in a storybook setting. Extensive native stonework graces both the home and the beautifully landscaped, certified native wildlife gardens, creating a seamless connection to the natural beauty of the surrounding mountains. Recent improvements include a new roof, updated electrical system, new lighting throughout and a new heat pump. The original hardwood floors have been carefully restored, blending historic character with modern convenience. This is a truly special property where history, character, and craftsmanship come together in one unforgettable setting. This home has 2 bedrooms plus an office on the main level, with the lower level being a large studio area with bedroom, sitting area and full bath. Meticulously maintained and truly move-in ready, this home is offered turn-key and can be sold furnished—ideal as a full-time residence, mountain getaway, or vacation rental investment. Outdoor enthusiasts will appreciate direct access to nearby adventure, including hiking to Bearwallow Mountain and on to Strawberry Gap, right from your door, plus a short drive to multiple trailheads featuring waterfalls, mountain streams, and sweeping 360-degree mountain views on Bearwallow Mtn. https://youtu.be/urLotv3KZew

206 Chestnut Hill Road, Gerton

$3,249,000

4 Beds ⋅ 6 Baths ⋅ 10170774 MLS

Nestled in the heart of coveted North Hills, this bespoke build by Homestead Building Company redefines modern luxury living. Delivering this September, the residence effortlessly fuses timeless elegance with elevated design -- with a luxurious heated salt water pool for an outdoor oasis. The main level is anchored by rich wide-plank hardwood floors and curated architectural trim. A dramatic grand foyer sets an opulent tone, featuring a custom wine gallery complete with stone accents and display racks. The gourmet kitchen boasts dual waterfall-edge quartz islands, exclusive "Luce Oro" quartz countertops and full-height riser, custom two-tone cabinetry to the ceiling, and an expansive secondary scullery and prep kitchen. The main-floor primary sanctuary with private foyer and custom accent millwork. The spa-inspired en-suite features a zero-entry tiled shower behind frosted glass, a freestanding soaking tub, custom dual vanities, and a meticulously fitted walk-in dressing room. Flowing seamlessly from the fireside family room—framed by a dovetail stone hearth—large glass sliding doors open to a vaulted screened porch with its own floor-to-ceiling stone fireplace. Outside, a resort-style saltwater pool awaits private relaxation. Complete with a main-level guest suite, an upstairs executive study, a dedicated media room with a full wet bar, and additional guest accommodations, this property offers an unparalleled sanctuary in an unbeatable location.

961 Wimbleton Dr, Raleigh

$560,000

4 Beds ⋅ 2 Baths ⋅ 4375202 MLS

A truly unique opportunity! TWO beautiful, vintage, hand-hewn log homes in a storybook setting with amazing possibilities. Located in the desirable Chestnut Hills subdivision, a 100 year old vacation cottage community just 20 mins from Asheville. The Main Cabin has 2BR/1BA with a full galley kitchen, lovely stone fireplace, rocking chair front porch, walk-out rear deck and hot tub. There is a small bonus room off the main bedroom currently used as a third sleeping area, but would be ideal for an office. The "Sunflower Cabin" has 2BR/1BA with a full kitchen, vaulted ceiling, a gorgeous enclosed sunroom, and walk-out rear deck. Both decks have commanding views over the Chestnut Hills Commons, stream and community garden. Beautiful stonework and hardscaping throughout the property. Dedicated stone lined parking pads and a gorgeous fire pit area. Fully stocked community pond and beautiful common areas. Some of the best hiking trails in the Asheville area are literally steps away, including the Florence Preserve and Bearwallow Mountain/Wild Cat Rock trail systems. Centrally located just 20 mins to Asheville, 30 mins to Hendersonville, 15 mins to Chimney Rock, and 20 minutes to Lake Lure. Two breweries and a grocery store located just 12 mins away in Fairview. The current configuration offers amazing flexibility....either as a turnkey vacation rental, a second home getaway with a guest cottage, or primary residence with in-law suite. Furniture is available with a few exclusions. Installed Spectrum fiber optic high speed internet. Short term vacation rentals are allowed in Chestnut Hills. Both homes have separate access and parking, and can be rented independently of each other. You'll love this amazing property!

72 Chestnut Hill Road, Gerton

$2,350,000

5 Beds ⋅ 7 Baths ⋅ 10164314 MLS

Custom luxury build by award winning ICG Homes. Nestled on a large homesite in highly sought after Chestnut Hills. Wide plank hardwoods and elegant finishes span throughout! The main level features the primary suite and en-suite guest for ultimate convenience! The gourmet kitchen features custom ceiling-height cabinetry, a large center island with barstool seating, Thermador gourmet appliances including a 48-inch gas range. All overlooking the spacious breakfast area! The primary suite features hardwood flooring and luxurious en-suite bath with zero-entry tiled shower, a freestanding tub, separate custom vanities and a huge walk-in closet! The family room offers a linear fireplace with tile surround and flanking built-ins! Large sliding glass doors open to the screened porch with outdoor fireplace. Upstairs, an oversized media room with half bath access, home gym/yoga room and 2 additional en-suite bedrooms! Complete with a 3-car garage for ample parking space.

5304 Dixon Dr, Raleigh

$6,250,000

5 Beds ⋅ 7 Baths ⋅ 10100186 MLS

2026 PARADE OF HOMES. The Wimbleton Estate - A Modern Scandinavian Masterpiece. Experience refined living in this exceptional new construction home situated on over 1.5 acres in Raleigh's prestigious Chestnut Hills neighborhood, in the heart of Raleigh's Midtown, just a few blocks away from I-440 and North Hills & North Hills Club. Every space in The Wimbleton Estate has been thoughtfully curated--from Taj Mahal quartzite surfaces and bronze mirror backsplashes to rift cut white oak cabinetry and custom designer tilework. The home delivers elegance in every room, with a design palette that blends warmth, luxury, and modern function. Wimbleton Estate offers over 7,000 sq ft of heated living space, seamlessly blending clean Scandinavian design with high-end, thoughtfully curated finishes. The open-concept floor plan boasts 10' ceilings and abundant natural light across expansive living areas. A gourmet kitchen anchors the home with quartzite countertops, a statement white oak island, and top-of-the-line Brizo and Ruvati fixtures. The adjoining scullery and separate bar/lounge make entertaining effortless. Designer lighting from Visual Comfort, Hinkley & Corbett adds elevated ambiance throughout. Set on over 1.5 acres, the outdoor living is nothing short of spectacular--your own private resort right at home. The expansive screened porch is the ultimate year-round retreat, with phantom screens, a built-in grill, tile accent wall, and infratech heaters creating the perfect setting for both outdoor dining and lounging. Beyond, the backyard unfolds into a stunning vision with a custom pool & spa and a putting green--an entertainer's dream and a family paradise. And, there's plenty of room to add a sport court or just enjoy a large yard for entertaining. Inside, the luxury continues with 5 bedrooms, a first-floor guest suite and study, 4 full baths, 2 half baths, and a showstopping primary suite designed for total comfort and style. Schedule your showing today before the parade begins and this home is gone!

1132 Wimbleton Dr, Raleigh

$39,000

4234752 MLS

Beautiful build lot(s) in highly desirable Chestnut Hills subdivision. Priced well below assessed tax value. Perfectly situated halfway between Lake Lure and Asheville. Two wooded, gently sloping lots totaling .64+/- acres with hardwood trees and Rhododendron. Winter views of Little Pisgah Mountain. Adjoining 50+ acres above property belongs to a land trust (Conserving Carolina). Chestnut Hills is an adorable vintage 1920's vacation cottage community that is 20 minutes to Asheville, 30 minutes to Hendersonville., 20 minutes to Chimney Rock/Lake Lure and 12 minutes to a grocery store, post office and a bank. Some of the best hiking trail systems (Wildcat Rock and the Florence Preserve) in the Asheville area are steps away. Chestnut Hills has a community fishing pond and a large commons area. Low HOA fee and no build time requirements. Access to the community water system is available when you decide to build. Spectrum high speed internet is available in Chestnut Hills. Short term rentals are allowed. You'll love this wonderful neighborhood!

0000 Thomasville Lane, Gerton

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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 .