Chestnut Hill Real Estate

Chestnut Hill Real Estate

Welcome to Chestnut Hill, a captivating subdivision nestled in the picturesque town of Highlands, North Carolina. Known for its breathtaking mountain views and serene atmosphere, Chestnut Hill offers a unique blend of natural beauty and modern living. This charming community is situated in Macon County, where the lush greenery and vibrant flora create an idyllic setting for families, retirees, and nature enthusiasts alike.

Chestnut Hill is characterized by its spacious lots and beautifully designed homes, each thoughtfully crafted to harmonize with the stunning landscape. Residents enjoy a sense of tranquility and privacy, making it an ideal retreat from the hustle and bustle of everyday life. The subdivision is conveniently located just a short drive from downtown Highlands, where you can explore a delightful array of shops, restaurants, and local attractions.

Outdoor enthusiasts will find themselves in paradise, with an abundance of recreational activities at their fingertips. Hiking trails, waterfalls, and parks are all within reach, allowing for endless opportunities to connect with nature. The area also boasts a mild climate, ensuring that you can enjoy the outdoors year-round.

Chestnut Hill is not just a place to live; it’s a community where neighbors become friends. With its welcoming atmosphere and rich natural surroundings, this subdivision is perfect for those seeking a peaceful lifestyle without sacrificing access to modern amenities. Discover the charm of Chestnut Hill and make it your new home in the heart of the North Carolina mountains.

Newest Listings in Chestnut Hill

$749,000
3 Beds ⋅ 2 Baths ⋅ 1004129 MLS ⋅ ACTIVE Status
Move-In Ready! This thoroughly renovated 3 bedroom/2 bathroom cottage is one of the finest in Chestnut Hill and one of the most compelling values in Highlands. Enjoy low-maintenance, one-level mountain living in Chestnut Hill, a community in which exterior maintenance and landscaping are meticulously managed for you, permitting true “lock & leave” living just minutes from the fine shops and dining in Highlands town center. Enter through the private front-screened porch and step into the large, bright Great Room with stone fireplace that opens to the covered rear-deck perfect for entertaining. As you tour the home, you will note the extensive premium renovations throughout including the gourmet kitchen, two bathrooms, new flooring and upgraded finishes including custom trim and doors. The large primary suite features a large walk-in closet and truly luxurious bathroom featuring a top-of-the-line multi-function Toto toilet. There are two (2) guest bedrooms and full-size laundry with ample storage and closet space throughout. For convenience, there is an attached one-car garage and for guests there is ample additional parking. A dedicated back-up generator, proximity to Highlands’ healthcare campus and easy, paved access provide confidence year-round. Whether you are looking for a private retreat, an income property or both, 11 Wood Lily Way awaits. Highlands NC was selected by Travel & Leisure as “America’s Best Small Mountain Town” in 2023 and Outside magazine ranked Highlands as one of its top ten small adventure towns in the world for 2026. Recent updates and upgrades extend beyond the extensive interior remodel and include: • New Roof • Professionally encapsulated crawlspace with commercial dehumidifier • New heating and air-conditioning systems • Dual tankless hot water heaters • Back-Up Generator • Monitored underground propane tank. • Premium duo-fold (top-down, bottom-up) cellular window treatments

11 Woodlily Way, Highlands

Listing courtesy of Christie's International Real Estate Highlands-Cashiers.

Listing courtesy of Christie's International Real Estate Highlands-Cashiers
$675,000
3 Beds ⋅ 2 Baths ⋅ 1003978 MLS ⋅ ACTIVE Status
Enjoy refined, low-maintenance mountain living in Chestnut Hill—an ideal setting for those who value both ease and independence. Here, exterior home maintenance and landscaping are thoughtfully managed for you, freeing your time to enjoy the lifestyle rather than the upkeep. This single-level three-bedroom, two-bath residence offers the simplicity of condominium living with the privacy, space, and comfort of a detached home—complete with its own garage. Located just moments from Highlands-Cashiers Hospital and the heart of downtown Highlands, you will appreciate the convenience of nearby medical services, dining, and shopping, all while returning home to a peaceful mountain setting. Chestnut Hill is perfectly suited for those seeking a full-time residence or a lock-and-leave retreat without sacrificing comfort, accessibility, or charm. HOA dues cover road maintenance, snow removal, water, and sewer, giving you true low-maintenance living. Tucked away at the end of a quiet cul-de-sac, the home features an open floor plan with beautiful new wood flooring, exposed wood beams in the great room, fully remodeled bathrooms, and an updated kitchen with new cabinetry, countertops, and stainless-steel appliances. Located just minutes from downtown Highlands, the community also offers a welcoming activity center where neighbors regularly gather for food, fun, and fellowship.

55 Wood Lily Way, Highlands

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty.

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty
$350,000
1 Beds ⋅ 1 Baths ⋅ 1003901 MLS ⋅ ACTIVE Status
Discover the ease and elegance of mountain living in this beautifully updated two-bedroom, two-bath condominium, located less than three miles from the vibrant heart of Highlands, NC. Thoughtfully designed for comfort, this single-level residence offers step-free access—an ideal choice for those seeking both convenience and tranquility. Enjoy peaceful mornings on your private patio, where the crisp mountain air and sounds of nature create a perfect retreat for reading, coffee, or quiet reflection. Inside, the home features a tastefully renovated kitchen and bathrooms with quality finishes and modern fixtures, while rich hardwood floors add warmth and sophistication throughout. As a resident, you’ll also enjoy covered access to a private activity building, soon to include a fitness room, game room, and a rentable guest suite—ideal for accommodating visiting friends and family with ease. For those needing additional storage or parking, a garage may be purchased separately for $30,000 on a first-come, first-served basis. Whether you’re looking to simplify without sacrificing style or embrace the charm and community of Highlands, this inviting condominium offers an exceptional opportunity to live comfortably in one of North Carolina’s most desirable mountain settings.

84 Clubhouse Trl Unit 101, Highlands

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty.

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty
$465,000
2 Beds ⋅ 2 Baths ⋅ 1003891 MLS ⋅ ACTIVE Status
Enjoy easy mountain living just minutes from the heart of Highlands, NC. This beautifully updated two-bedroom, two-bath condo offers the perfect blend of comfort, style, and convenience—all on a single level for effortless access. Whether you’re enjoying a quiet morning on your private patio or entertaining guests in your open-concept living space, you’ll appreciate the thoughtful touches throughout. The renovated kitchen and baths feature contemporary finishes designed with both beauty and function in mind, while the rich hardwood floors lend warmth and timeless appeal. One of the two bedrooms is currently styled as a cozy study or reading room, but easily converts back to a guest space when family or friends come to visit. Located in a peaceful community just under three miles from downtown Highlands, this home offers a serene setting with the benefits of nearby dining, shopping, and cultural activities. For added convenience, a private garage is available for purchase separately at $30,000—offered on a first-come, first-served basis. If you're seeking a refined, low-maintenance lifestyle in one of Western North Carolina’s most desirable mountain towns, this charming condo is ready to welcome you home.

84 Clubhouse Trl Unit 108, Highlands

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty.

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty
$675,000
2 Beds ⋅ 2 Baths ⋅ 1002858 MLS ⋅ ACTIVE Status
Life in the mountains often asks for a balance - beauty without burden, charm without complication- and this thoughtfully maintained cottage in the Chestnut Hill community delivers exactly that. Just minutes from the heart of Highlands and conveniently close to Highlands-Cashiers Hospital, the home offers a rare blend of accessibility and retreat. Whether it’s a morning coffee run into town, an evening dinner on Main Street, or the peace of mind that comes with nearby medical care, everything you need is effortlessly within reach. What sets this property apart is its simplicity of living. Though it is a single-family home, it lives with the ease and freedom of a lock-and-leave condominium - no constant upkeep, no lingering to-do lists, just the ability to come and go as you please, knowing your home remains as pristine as you left it. Inside, the atmosphere is light and welcoming. A vaulted ceiling elevates the living room, where natural light filters in and creates a sense of openness that feels both airy and grounded. The kitchen has been tastefully updated, offering generous storage and a comfortable breakfast nook that invites slow mornings and unhurried conversation. From here, the transition to the back patio is seamless - perfect for enjoying cool mountain air or a quiet evening outdoors. Two well-proportioned bedrooms and two full baths provide both comfort and privacy, whether hosting guests or enjoying a quiet weekend alone. An attached one-car garage adds another layer of convenience, offering protected parking along with valuable storage space. This is mountain living reimagined - not as a project, but as a pleasure. A place where the pace slows, the surroundings inspire, and homeownership feels refreshingly uncomplicated.

31 Chestnut Hl, Highlands

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty.

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty
$465,000
2 Beds ⋅ 2 Baths ⋅ 1000219 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to your new home less than three miles to the heart of Highlands, NC! This charming two-bedroom, two-bath condo is perfect for those seeking comfort and convenience. Easy in and out with everything on one level, this lovely residence features a welcoming patio, ideal for enjoying your morning coffee or reading a good book in the cool mountain air. Step inside to discover beautifully renovated kitchen and baths, complete with modern fixtures and finishes. The gleaming hardwood floors throughout add a touch of elegance and warmth, making you feel right at home. One of the bedrooms is currently used as a study, but could easily be a guest room. A garage for the unit may be purchased separately if desired. The garages will be offered on a first come, first serve basis for $30K. Don't miss this opportunity to own a piece of Paradise in Highlands! Schedule your viewing today and start living the life you've always dreamed of.

84 Clubhouse Trl Unit 104, Highlands

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty.

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty
$990,000
3 Beds ⋅ 3 Baths ⋅ 4163727 MLS ⋅ ACTIVE Status
One residence remains in Phase 1 and pricing will increase in Phase 2! Welcome to Aster Court, an extraordinary new townhome community less than half a mile from Downtown Asheville, in one of the city’s most historic neighborhoods. Enter from your expansive 216 SQFT terrace to a wide-open floor plan with 10 ft ceilings, gorgeous wood flooring, large windows, and a chef’s kitchen featuring premium finishes, quartz countertops, soft-close cabinetry, and a center island. This plan boasts walk-in closets in all bedrooms and a sweeping primary suite that spans the entire 3rd floor with a private den, soaking tub w/ separate shower, two walk-in closets, and access to a private terrace and veranda. Additional features include solid-core interior doors, Cat-6 wiring, custom wood shelving, a tankless water heater, Delta faucets and more. Ideally located across from Jettie Rae’s Oyster House, Taco Temple, and City Bakery. Select your own interiors and move in in mid-2027!

3 Aster Court, Asheville

Listing courtesy of Howard Hanna Beverly-Hanks Biltmore Avenue. mills.coin@allentate.com
Start Your Search

“ Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Some IDX listings have been excluded from this website. Properties may or may not be listed by the office/agent presenting the information © 2026 Canopy MLS as distributed by MLS GRID”

Last Updated: