View All Macon County NC Colonial Style Homes Listings

225 Bowery Rd, Highlands
$6,250,000
6 Beds ⋅ 8 Baths ⋅ 1002981 MLS
Imagine a life where each morning begins with a short walk from your front gate across the street to the trail leading directly into the heart of Highlands. Here, daily life balances effortless access to vibrant mountain living with the calm privacy of a wooded sanctuary. Set on four remarkable acres just moments from town, this estate is more than a beautiful home—it is part of Highlands’ enduring story. The property traces its origins to the early influence of the Ravenel family of Charleston, whose extensive landholdings helped shape the Plateau. Today, these acres carry forward that legacy, offering a rare sense of continuity and place. What makes this offering especially rare is the land itself. Unlike many in-town properties, these four acres are largely usable—opening the door to a more intentional way of living. Whether envisioned as a gentleman’s farm, greenhouse, or thoughtfully designed family compound, the property lends itself naturally to a more sustainable lifestyle—all just minutes from Main Street. Built circa 1922 by the Evins family and thoughtfully restored by builder John Underwood with design by architect Sam Edgens, the home honors its history while living comfortably for today. A gated entrance and laurel-lined drive lead to an elegant three-story mountain colonial of approximately 6,500 square feet. Inside, original oak and antique chestnut floors harvested from the land, stone fireplaces, handcrafted millwork, & more than 60 windows create warmth and scale. In-floor hydronic heating on the first and second levels ensures year-round comfort. The chef’s kitchen, with its own fireplace, invites both casual mornings and refined entertaining, while spa-inspired baths and flexible third-floor spaces support everyday living and hosting alike. Outdoor living is equally compelling, with stone patios, a Rumford-style fireplace, heated pool, and spa surrounded by mature plantings. The home sits on the continental divide so rain from the front flows towards the west and rain from the back of the home flows east. An activity barn, trails, and expansive lawns offer space for recreation and reflection, while a guest cottage & additional accommodations above the garage support a multi-generational retreat. Just beyond, the Rhododendron Trail connects to Ravenel Lake, Sunset Rock, & downtown Highlands. This is a legacy property, private, connected, and increasingly rare. Seller will pay for a Caretaker & Concierge for 2 years from closing.

225 Bowery Rd, Highlands

401 N Fifth St, Highlands
$2,700,000
3 Beds ⋅ 4 Baths ⋅ 103319 MLS
LOCATION! This Highlands landmark is one of the last great, walk-to-town parcels. Zoned B-4 (light commercial) and sits on .92 acre. Renovate or start over- anything can be duplicated- EXCEPT the location. The first time on the market and being offered AS-IS. The main level has wood floors and is paneled with clear Chestnut as the home was built just as the Chestnut blight came through town. The main level has a small kitchenette, storage, full bath and 4 rooms (The former living area is partitioned to allow for the reception area.) The attic is floored in, runs the entire length of the house and has great storage. This is a property full of memories for many local people. In the 1920s, this property was a 9-hole golf course as part of the Hall House property. Built in 1931 with chestnut paneling on the main level, this property has been a personal residence, home occupation, B&B, and is now zoned B-4. This property has been in the same family since the town was incorporated, and once took up the whole block. This is the only parcel left and contains .92 ac+/-. The home of Margaret and Tudor Hall and their extended family lived here from 1931 until the early 1990s when The Chambers Agency moved their real estate and vacation rentals office. Tudor and Margaret had a real estate office in town and were charter members of the Highlands Board of Realtors in 1956. In the mid-1990s, the garage was renovated into a one-bedroom/one-bath apartment and has been partially renovated. Prior to 1992, Mrs. Hall ran a boutique B&B, The Hall House, and the rooms upstairs that had been her children's bedrooms became weekend spots for tourists, and later became real estate offices for The Chambers Agency. In 2013, the four upper-level rooms were converted into two one-bedroom/one-bath apartments for workforce housing.

401 N Fifth St, Highlands

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Macon County, NC · Curated MLS Search

Colonial Style Homes in Macon County, NC

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

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