GEORGIA | NORTH CAROLINA | FLORIDA

Real Estate, Residential & Commercial in Georgia, North Carolina & Florida

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$5,999,000
37 Days On Site

424 Big Bearpen Road
Highlands, NC 28741

For Sale|Single Family Residence|Active
4
Beds
4
Total Baths
3
Full Baths
1
Partial Bath
2008
Built
Subdivision:
Big Bear Pen
County:
Macon
Listing courtesy of Josephine Lovell of Highlands Sotheby’s International Realty – DT
Call Now: +1 706-746-2900
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+1 706-746-2900
424 Big Bearpen Road424 Big Bearpen Road424 Big Bearpen Road424 Big Bearpen Road
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Mortgage Calculator

Monthly Payment (Est.)

$27,370
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2025 Information is deemed reliable but not guaranteed.

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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Listing Snapshot
Price 
$5,999,000
Days On Site 
37 Days
Bedrooms 
4
Inside Area (SqFt) 
N/A
Total Baths 
4
Full Baths 
3
Partial Baths 
1
Lot Size 
1.3 Acres
Year Built 
2008
MLS® Number 
1001584
Status 
Active
Property Tax 
$9,389.94
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
a month agoListing first seen on site
a month agoListing updated with changes from the MLS®
General Features
Acres 
1.3
Attached Garage 
Yes
Garage 
Yes
Garage Spaces 
2
Levels 
Two
Number Of Stories 
2
Parking 
AttachedGarage
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
Style 
Craftsman
Utilities 
Cable AvailableElectricity ConnectedPropaneSewer ConnectedWater Connected
Water Source 
Public
Zoning 
Residential
Interior Features
Appliances 
DryerDishwasherDisposalPropane CooktopWasher
Basement 
Crawl SpaceExterior Entry
Cooling 
Ceiling Fan(s)Central Air
Electric 
Generator
Fireplace 
Yes
Fireplace Features 
Free StandingGas LogGas StarterKitchenLibraryLiving RoomSee RemarksStoneWood Burning
Fireplaces 
4
Flooring 
CarpetHardwoodStoneTile
Furnished 
Unfurnished
Heating 
Natural Gas
Interior 
Wet BarBookcasesCeiling Fan(s)ChandelierKitchen IslandPantryVaulted Ceiling(s)Walk-In Closet(s)
Laundry Features 
Main Level
Dining Room 
Level – Main
Kitchen 
Level – Main
Laundry 
Level – Main
Living Room 
Level – Main
Master Bathroom 
Level – Main
Master Bedroom 
Level – Main
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Exterior Features
Construction Details 
StoneWood Siding
Exterior 
CourtyardGardenOtherPrivate Yard
Lot Features 
Back YardGardenLandscapedPrivateSee RemarksLevel
Patio And Porch 
PorchTerrace
Roof 
ShakeWood
View 
GardenMountain(s)
Waterview 
GardenMountain(s)
Community Features
Community Features 
None
MLS Area 
Highlands In-Town
Listing courtesy of Josephine Lovell of Highlands Sotheby’s International Realty – DT



Listing information is provided by Participants of the Highlands Cashiers Board of REALTORS MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Copyright 2025, Highlands Cashiers Board of REALTORS MLS.
Data last updated at: 2025-10-16 07:17 PM UTC

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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