424 Big Bearpen Road Highlands, NC $ 5,999,000
424 Big Bearpen Road
$ 5,999,000
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424 Big Bearpen Road

Highlands, NC, 28741
$ 5,999,000
Bedrooms4 Baths3.1

Monthly Estimate*

$ 37,426

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Single Family Home for sale in Highlands, NC

for $5,999,000 with 4 bedrooms and 3 full baths, 1 half bath. This home was built in 2008 on a lot size of 1.3.

Welcome to "Thistlewaite" - a European-inspired masterpiece in the heart of Highlands, North Carolina. Born from the vision of a creative Atlanta couple, Thistlewaite was modeled after an English country house designed in 1900 by renowned architect Edwin Lutyens in the Arts and Crafts tradition. To bring this dream to life, they assembled an extraordinary team: close friend and celebrated classical architect Norman Davenport Askins, legendary builder Tommy Chambers, and acclaimed landscape designer Alex Smith. The result, completed in 2009, is an architectural and garden jewel unlike anything else in Highlands. The property was originally part of the seven-acre site of the adjacent 1930's Joe Webb cabin and still includes its original spring house. To create the home's setting, a small clearing in the forest was sculpted into a flat homesite with a dramatic 24-foot retaining wall. Stone blasted from the site now forms the garden walls, seamlessly tying the residence to its natural surroundings. Cross the stone bridge over a rushing creek and be immediately captivated by the approach garden, a lush entryway that feels like a world apart. Nestled within virgin forest off Big Bear Pen Road, and bordered by Highlands Land Trust property with views of the historic Kelsey Trail, the home welcomes you through a distinctive gatehouse crowned with a zinc ornament salvaged from a circa-1900 Denver building. The gardens act as an extension of the home, with terraces, an outdoor fireplace, and a formal parterre. Two porches - an inviting entrance porch and a "drinking porch" off the living room and primary suite - overlook the gardens and enclosed courtyard. Inside, warm and gracious living spaces unfold: A keeping room with a stone fireplace shared with the kitchen. A scullery kitchen with ovens, dishwasher, and sink, keeping the main kitchen always ready for entertaining. A built-in bar leading to a light-filled room with courtyard views. A formal living room with another fireplace connecting to the luxurious primary suite. Upstairs, three to four additional bedrooms and a cozy second great room provide comfort for family and guests. Materials were chosen with artistry and authenticity: native North Carolina granite, rough-hewn siding milled from hemlock felled on the property, reclaimed beams and barn wood from Pennsylvania, and antique accents such as milestone at the gatehouse.

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Single Family Contingent

Price

$ 5,999,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 9,389

Style

Lot Size

1.3

Year Built

2008

Town/City

Highlands

County/Region

Macon

MLS | Web ID

1001584

Features
General
View Garden Mountain(s)
Heating Gas
Cooling Central Air
Year Built 2008
Appliances Dryer Dishwasher Disposal Propane Cooktop Washer
Exterior Features Courtyard Garden Other Private Yard
Interior Features Wet Bar Bookcases Ceiling Fan(s) Chandelier Separate/Formal Dining Room Kitchen Island Pantry Vaulted Ceiling(s) Walk-In Closet(s)
Utilities Cable Available Electricity Connected Propane Sewer Connected Satellite Internet Available Water Connected
Roof Shake Wood
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* Excluded Features
List By
Josephine Lovell

Listing Agent

Highlands Sotheby's International Realty - Dt

Broker

josephine.lovell@sothebysrealty.com

Email

Affordability Calculator

$38,208
Per Month
98%
2%
0%
Monthly Principal & Interest
$37,426
Monthly Property Taxes
$782
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Pricing History
DatePricePrice ChangeDescription
9/9/2025$5,999,000 Listed Price

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424 Big Bearpen Road, Highlands, NC, 28741 is a Single Family Home for sale at $5,999,000 with a lot size of 1.3. 424 Big Bearpen Road has 4 bedrooms, 3.1 baths, and was built in 2008. The property's zip code is 28741 which is in Highlands, NC