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245 Woodland Ridge Dr, Highlands
$2,450,000
4 Beds ⋅ 5 Baths ⋅ 1003779 MLS
Less than three miles from Main Street Highlands and just moments from Highlands-Cashiers Hospital, this inviting Woodland Ridge home offers an easy connection to everything that makes life on the Plateau so appealing. From mornings spent exploring nearby hiking trails and waterfalls to afternoons browsing Main Street’s distinctive shops and galleries and evenings enjoying Highlands’ celebrated restaurants, this location makes it easy to experience the very best of the mountains. Set on more than two beautifully landscaped acres, the property enjoys a lovely mountain view and a sense of space that is increasingly difficult to find so close to town. The grounds create a beautiful arrival and a peaceful natural setting for watching the seasons unfold. Everything needed for comfortable daily living is thoughtfully arranged on the main floor. Beautiful wood and beamed ceilings bring warmth and character to the open floor plan, where the kitchen, dining, and living areas flow naturally together. Large windows invite the outdoors in, while the generous open deck provides plenty of room for relaxing in the sunshine, enjoying the mountain air, or gathering with friends. The spacious screened porch, complete with a fireplace, is certain to become a favorite destination for morning coffee, leisurely dinners, football Saturdays, and cozy evenings long after the sun has set. Upstairs, a comfortable loft offers a relaxed seating area where guests can read, visit, or enjoy a little quiet time, along with a private bedroom suite. The lower level is equally welcoming, with two additional guest suites, a family room, and its own deck. This thoughtful arrangement allows family and friends to gather comfortably while still enjoying private spaces of their own. Days here may begin with a hike, a round of golf, fly-fishing in a mountain stream, or a scenic drive along winding mountain roads. They can end with dinner in town or beside the porch fireplace as the evening settles over the landscape. With generous accommodations, multiple indoor and outdoor gathering spaces, beautiful grounds, and a wonderfully convenient location, this Woodland Ridge residence offers a warm and welcoming setting for enjoying the Highlands lifestyle throughout the seasons.

245 Woodland Ridge Dr, Highlands

221 Hideaway Trl, Highlands
$1,175,000
3 Beds ⋅ 4 Baths ⋅ 1003511 MLS
Located in a quiet mountain community just minutes from downtown Highlands and Highlands-Cashiers Hospital, this inviting home offers an exceptional combination of comfort, convenience, and outdoor recreation. The neighborhood is one of the Plateau's few equestrian communities, featuring community stables, multiple paddocks, and access to riding and hiking trails that traverse the natural beauty of Shortoff Mountain. Residents also enjoy a spring-fed lake with fishing and kayaking, as well as a community tennis court. Surrounded by mature hardwoods and native mountain plantings, the property offers an attractive, low-maintenance setting that complements the surrounding landscape. Inside, the home features three bedrooms and three baths, with a spacious living room highlighted by a vaulted ceiling and a dramatic floor-to-ceiling stone fireplace. The main living areas open seamlessly to a large combination of covered and open-air decking, creating ideal spaces for entertaining, outdoor dining, or simply enjoying the mountain environment. A lower patio with a firepit provides an additional gathering area for family and friends. The terrace level expands the home's living space with a comfortable family room perfect for games, movie nights, or casual relaxation, along with a private office for those who work remotely or simply desire a quiet retreat. Offering access to outstanding community amenities and a location convenient to both Highlands and the hospital, this home presents an opportunity to enjoy the best of mountain living in one of the Plateau's most distinctive neighborhoods.

221 Hideaway Trl, Highlands

16 Hemlock Way, Highlands
$2,000,000
4 Beds ⋅ 3 Baths ⋅ 1001549 MLS
Experience refined mountain living in this beautifully maintained 4-bedroom, 3-bath home nestled on 1.09 acres in the prestigious gated community of Cullasaja Club. Surrounded by towering trees and native rhododendrons, this private retreat offers both luxurious details and practical features for comfortable year-round or seasonal living. Step inside to find gleaming new hardwood floors throughout the main level. The Great Room impresses with a soaring beamed cathedral ceiling, a stone wood-burning fireplace, and sliding doors that lead to a screened porch with a second wood-burning fireplace—perfect for enjoying cool mountain evenings. The formal dining room opens to a wraparound deck, ideal for entertaining or relaxing in the peaceful wooded surroundings. The chef’s kitchen is well-appointed with stainless steel appliances, including a built-in refrigerator, double wall ovens, a glass cooktop, a dishwasher, a trash compactor, and a disposal, as well as a convenient breakfast bar for casual dining. The main-level primary ensuite is a haven of relaxation, offering a spacious walk-in shower, walk-in closet, and direct access to the hall laundry room. A guest bedroom and full bath complete the main level. Downstairs, two additional bedrooms, a full bath, and a cozy family room provide excellent space for guests or multi-generational living. Step outside to a covered lower deck and enjoy the sounds of nature. An encapsulated crawlspace includes a small workshop area for hobbies and storage. A 2-car carport adds to the home’s functionality. The included Cullasaja Club membership (subject to approval) unlocks an extraordinary lifestyle: play a round on the Arnold Palmer-designed championship golf course, enjoy tennis or croquet, stay active in the state-of-the-art fitness center, or relax at the resort-style pool. For nature lovers, Ravenel Lake offers a private 27-acre setting for fishing, kayaking, or simply soaking in the serenity. Don't miss this exceptional opportunity to enjoy the lifestyle, natural beauty, and upscale amenities that define the Highlands-Cashiers Plateau. Schedule your private tour today!

16 Hemlock Way, Highlands

108 W View Way, Highlands
$2,600,000
4 Beds ⋅ 4 Baths ⋅ 1001047 MLS
Live Elevated: Luxury Mountain Living Awaits at Cullasaja Club Searching for mountain views and a lifestyle to match? Welcome to your next home in the prestigious Cullasaja Club—a rare opportunity to own a beautifully reimagined mountain retreat in one of Highlands’ most exclusive gated communities. Perched on a peaceful, wooded lot with sweeping western-facing views, this home offers front-row seats to breathtaking sunsets over the Smoky Mountains. Unwind on the expansive screened-in four-season porch, complete with a cozy fireplace and drop-down screens, or immerse yourself in the club’s elite amenities, with membership approval—Arnold Palmer signature golf, fine dining, tennis, croquet, fitness, and more—just moments from your door. This recently renovated 4-bedroom and 3.5-bath masterpiece was designed for those who crave relaxed luxury. Vaulted ceilings and soaring windows flood the home with natural light, while warm wood tones, sleek finishes, and an open-concept floor plan create a welcoming yet sophisticated ambiance. The chef’s kitchen is a showstopper, featuring top-tier appliances, custom cabinetry, and seamless flow into the great room, ideal for entertaining. The first-floor owner’s suite is a private sanctuary, offering a spa-style bath with two large walk-in closets and a private office, while the additional first-floor guest suite and upstairs living space provide comfortable privacy for visitors of all ages. More than just a home, this is your invitation to the mountain lifestyle you’ve always dreamed of. Homes of this caliber in Cullasaja Club are rare—don’t miss your chance. Call today to schedule your private tour and take the first step toward mountain living at its finest.

108 W View Way, Highlands

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Macon County, NC · Curated MLS Search

Homes with Irregular Lot in Macon County, NC

An editorially curated view of every active homes with irregular lot listing in Macon County, NC. Updated in real time from the local MLS, presented without the noise.

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