Own a piece of Highlands History! Almost 3 acres in town that is mostly level. Garden, create a family compound - too many possibilities to list them all!
View from N. 5th Street
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Owned by the Whittle Family since 1925, this historic home is ready for new owners.
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Almost 3 acres in town that is mostly level.  Garden, create a family compound - too many possibilities to list them all!
Covered Porch
Mud Room/Sunroom/Laundry Room
Mud Room / Sunroom & Laundry Closet
Living Room
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Half Bath on Main with Antique High-tank Toilet
Kitchen with Built-in Desk
Formal Dining Room
Primary Ensuite on the Main Level
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Primary Ensuite Full Bath with Walk-in Shower
Beautiful Original White Oak Staircase
Upstairs Hallway
Guest Room or Second Owner Ensuite Bedroom on the Upper Level
Guest Room or Second Owner Ensuite Bedroom on the Upper Level
Guest Room or Second Owner Ensuite Full Bath on the Upper Level
Guest Room 2
Guest Room 3 with private entrance to shared Full Guest Bath
Guest Room 3 with private entrance to shared Full Guest Bath
Full Guest Bath on Upper Level with Antique Cast Iron Soaking Tub & High-tank Toilet
Barn and Fire Pit
Expansive Gentle Yard
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Aerial of House, Barn and Apple Trees
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View from the Creek to the House
Babbling Creek along one property line
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Aerial of the property - not based on a survey; for reference only.
Proximity to Downtown Highlands
Floor Plan - Main Level
Floor Plan - Upper Level
Floor Plan - All Levels
46 photos

$4,200,000

Highlands, NC 28741
Listed by Doug Treadwell · MOUNTAIN LIFE REAL ESTATE, LLC
Bedrooms
4
Bathrooms
3.1
Living area
1,944 sqft
Year built
1900

About this home

A once-in-a-generation opportunity to own one of Highlands' most cherished legacy properties. Just blocks from downtown, the historic Whittle House has been lovingly maintained by the same family for over 100 years and five generations and offers an extraordinary combination of history, privacy, and location. Set on 2.88 gently rolling acres framed by towering pines, rhododendrons, and a gentle stream, this 4-bedroom, 3.5-bath farmhouse captures the timeless charm of Old Highlands. Built in the late 1800’s and on the National Historic Registry, the home includes tongue-and-groove ceilings, a stone fireplace, expansive living spaces, a detached garage with a loft, and beautifully preserved grounds that have remained largely unchanged for nearly a century. Rich in character and surrounded by nature, this remarkable estate offers endless possibilities as a private family retreat, legacy property, or future investment opportunity. Properties of this significance and proximity to downtown Highlands rarely become available. Schedule your private showing today and become the next steward of one of Highlands' most treasured homes.

Highlights

Fireplace

Property details

MLS #
CAR4390432
Property type
Single Family Residence
Subdivision
None
Status
Active
Days on market
7
On market date
N/A
Stories
N/A
Garage spaces
N/A
Lot size
N/A
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Blue Ridge School
6.4 mi away · Grades -1-6
Nearest school -- attendance-zone data not available here
3.3
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: C (2025)
Enrollment
154
Student:teacher ratio
12.8:1
District
Jackson County Public Schools
Middle
None found nearby
High
Macon Early College High School
12.81 mi away · Grades 9-13
Zoned school (attendance boundary, 2015-16 data)
3.1
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
129
Student:teacher ratio
32.3:1
District
Macon County Schools

Mortgage calculator

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Est. monthly payment
$25,443/mo
$840,000 down
$3,360,000 loan
Principal & interest$21,793
Property tax (est.)$3,500
Home insurance (est.)$150

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Data source: Listing information provided by Canopy MLS (carolina) via Trestle/CoreLogic. Last updated June 12, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.