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476 Winfield Farm Rd, Scaly Mountain
$2,495,000
4 Beds ⋅ 5 Baths ⋅ 1003340 MLS
A true traditional Highlands' farmhouse, built in 1993, sits on the Atlanta side of Highlands just about 12 minutes from downtown and enjoys beautiful views of Scaly and King mountains. Screened from the road by a mature evergreen hedge, it offers a sense of privacy and a gracious approach. A wide porch wraps around three sides of the home, with decking laid on a true north–south axis and the Continental Divide running through the middle of the house. In the evenings, the North Star is centered in the view from the porch, with the Big Dipper pointing directly to it. The porch provides two comfortable seating areas plus an outdoor dining space overlooking the Hosta garden. Inside, high ceilings and two fireplaces create airy, welcoming living spaces. The vaulted living room is a standout, featuring beams salvaged from Charlotte’s original train station for distinctive historic character. The main level includes an owner’s bedroom and bath, as well as a conveniently located half-bath off the entrance hall. Upstairs are three additional bedrooms and three baths, a library area, and a separate office. From the office and the two front-facing bedrooms you can see the farm’s pastures and Scaly Mountain, while the third bedroom opens to a balcony overlooking the rear terrace and garden area. A two-car garage connects to the main house via a covered breezeway, with the parking area screened from the back gardens by hydrangeas and evergreens. The property also offers a potting shed designed by Atlanta architect Tom Ventulett and a separate tool house. Extensive gardens showcase a wide variety of conifers, a raised fenced vegetable garden, terraced beds with dahlias and other flowers for cutting, and a wooded Hosta trail leading to an orchard with about a dozen apple and pear trees. Near the gardens and orchard, a croquet court enclosed by an evergreen hedge provides a spacious, level setting for recreation or tented outdoor events.

476 Winfield Farm Rd, Scaly Mountain

1884 Dillard Rd, Highlands
$625,000
2 Beds ⋅ 2 Baths ⋅ 1002800 MLS
Short Term Rentals Allowed. Welcome to your mountain Treehouse retreat, offering both seclusion and convenience. A classic Highlands 2-bedroom, 2-bath cottage, perfectly tucked away in nature yet just 2 minutes from town the historic Highlands Country Club and 7 min. from the shops, restaurants and varied activities of Highlands center. Nestled in a large grove of Rhododendron under a canopy of mature Eastern White Pine, this home requires no lawn maintenance. Inside, an open living room; dining room space flows into the kitchen, with both areas opening onto a spacious back deck; an immediate connection to nature and relaxation. Large, energy-efficient windows allow an abundance of natural light and nature’s beauty to continue into the home. The rear of the .56 acre property borders Glen Falls Rd (1 mi.) providing access to beautiful Glen Falls and its popular, well-marked, pet-friendly hiking trail. Perfect for exploring nature with friends and family. The primary bedroom and bath are located on the main floor, while the second bedroom and bath upstairs offer privacy for guests. Whether you’re looking for a peaceful Highlands retreat, retirement home or a smart investment, this property is a rare find. While it boasts a Highlands address, it’s outside the town’s rental restrictions, allowing you the freedom to rent it by the day, week, or month—a major advantage for short-term rental income. And, no HOA! This is your chance to own a true Highlands hideaway; fully furnished, 2025-2026 renovation that blends mountain charm, prime location, and rental flexibility. Don’t miss out! FEATURES: • 2025 HVAC: Carrier High Efficiency Heat Pump paired with Optimally Engineered Ductwork; 2026: LG Appliances Washer/Dryer, Refrigerator, 5-Burner Cooktop/Multi-Mode Oven, Dishwasher 2026VinoTemp Wine Cooler (51 bottle, 2-Zone) 2026 Integrated Smoke/CO Alarm 2025: Flooring—Main Living Areas; Kitchen, Classic Hardwood Floors (Bedrooms) • 2025: Roof(Certanteed Landmark) • 2025 Exterior Stain (Cabot); Interior Paint (Benjamin Moore) . 2026 Guest Bath Vanity, Toilet, Hardwood Floors 2025 Rustica Metal Front Awning • 2025 Crab Orchard Stone Pathway; Front Porch • 2025 Parking Pad renovation

1884 Dillard Rd, Highlands

50 Pearl Dr, Highlands
$575,000
3 Beds ⋅ 2 Baths ⋅ 1001401 MLS
Pond, Pasture, and a Little Slice of Paradise! Looking for a little peace, a little privacy, and a lot of charm? Welcome to 50 Pearl Drive, a sweet spot on the Highlands-Cashiers Plateau. This is where you’ll enjoy your own pond from almost an acre of unrestricted land and pluck apples or peaches from your trees. This well-cared-for 3-bedroom, 2-bath home offers the rare combination of privacy, charm, and convenience, all in a serene mountain setting bordered on two sides by a large horse farm. Inside the home, you find a warm and inviting main level with a cozy living room, sunny kitchen, full bath, and three bedrooms. Need more space? The lower level is already equipped with a finished full bath and is just waiting to be transformed into whatever you need - game room, bunk space, hobby haven - you name it. Plus, finishing this space could easily double your square footage and living areas. This home doesn’t just invite you outside, it practically insists. With two levels of spacious decks, there’s plenty of room to grill, chill, or just enjoy the mountain air. Giving you front-row seats to the sights and sounds of nature. Outside, the land is just as special. There’s a 2-car garage, a tractor barn for all your gear, a private pond, and an edible landscape that includes grapevines plus apple, peach, and plum trees. It’s like having your own little orchard in the mountains. Whether you’re looking for a full-time residence, a mountain getaway, or a property with room to grow, 50 Pearl Drive is a lovingly maintained property in an unbeatable location. So when you're ready to hit the town, you're just a short drive to downtown Highlands or Cashiers. Easy access. Beautiful land. Endless potential. Come see why this one feels like home!

50 Pearl Dr, Highlands

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Macon County, NC · Curated MLS Search

Orchard Homes in Macon County, NC

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