OFF MARKET

Off market sep 2024 for $3.5M

$4,001,557

Est. refi paymentEst. refi $23,276/mo

•

—

sq ft

434 Whiteside Mountain Rd, Highlands, NC 28741

About this home

Renovated in the early 90's. Sit on the back porch and listen to the waterfall. Mountain architectural masterpiece offering an unparalleled blend of sophistication and comfort. Enjoy up-close views of Whiteside Mountain from the screened and open porches that cover the back of the home. Owned by one of the most prominent families in the south. This family has been featured in several publications-including Town & Country Magazine. Own a piece of history: debutante parties and breezy country club living. Named after their honeymoon cottage in Bermuda - Horizons Home is a perfect description of the distant views. The family summered in Highlands at the DuPont residence for many years before they found their perfect mountain home. This home features: 4 bedrooms suites - the Primary suite (with fireplace) has private 'His' and 'Hers' bathrooms. 2 wet bars (one with ice maker and beverage refrigerator), 2 living rooms (both with fireplaces), office, billiards room, kitchen with professional grade Wolf stove and fireplace. Being sold furnished, with a small list of exclusions. 3.66 acres(Jackson County)+. 56 acres (Macon County)=4.22+/- ACRES on the Big View side of Whiteside Mountain Road. The waterfall behind the property is one of the beginnings of the Savannah River! Private croquet field - the perfect location for Wine and Wickets. There are five fireplaces in total. The outdoor fireplace (is a welcoming beacon) with it's boulders for seats - it is a perfect spot for roasting s'mores with your grandchildren!! No drive by's - active cameras.

Single-familyProperty Type

1942Year Built

4.22 acresLot Size

2 spacesParking

Listed by Andrea Gabbard • Highlands Sotheby's International Realty - DT

Listed by Josephine Lovell • Highlands Sotheby's International Realty - DT

Contact: 8285268300

Bought with Lori Mattice • Highlands Sotheby's International Realty - DT

Redfin checked: 2 minutes ago

•Source:HCMLS #103071

Redfin Estimate

$4,001,557

$502K since sold in September 2024$171K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.3% higher than the average sale price ($3.53M) of 6 comparable homes.

SOLD SEP 10, 2026
$2,650,000
A
4 beds5 baths— sq ft
653 Country Club Dr, Highlands, NC 28741
SOLD OCT 5, 2026
$5,000,000
B
5 beds5.5 baths— sq ft
749 Stillmont Cir, Cashiers, NC 28717
SOLD SEP 9, 2026
$2,500,020
C
4 beds4.5 baths— sq ft
126 Forestland Rd, Cashiers, NC 28717
SOLD SEP 18, 2026
$4,500,000
D
4 beds4.5 baths— sq ft
744 Old Wagon Trl, Highlands, NC 28741
SOLD NOV 3, 2026
$4,450,000
E
4 beds5.5 baths— sq ft
51 Bear Shadow Rdg, Highlands, NC 28741
SOLD SEP 8, 2026
$2,100,000
F
3 beds4.5 baths— sq ft
188 Logan Ln, Cashiers, NC 28717

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Earn from this home

Sell

$1,076,783

Est. take-home

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Refinance

Est. cash available

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Rent

$4,799/mo

Redfin rental estimate

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Market trends in 28741, NC

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

94.4%

0.0% MoM

Median sale price

$1.4M

$174K MoM

Avg. days on market

78d

10 days MoM

Recently sold homes

5 MoM

New listings for sale

NEW 22 HRS AGO
$4,250,000
4 beds3.5 baths— sq ft
34 Bear Mor Ridge Rdg, Highlands, NC 28741
$1,200,000
3 beds2.5 baths— sq ft
16 Cowee Ridge Trl, Highlands, NC 28741
3D WALKTHROUGH
$1,100,000
3 beds2 baths— sq ft
85 Ralph Thomas Rd, Highlands, NC 28741
3D WALKTHROUGH
$1,950,000
8 beds5 baths— sq ft
230 Moon Mountain Rd, Highlands, NC 28741
3D WALKTHROUGH
$999,000
3 beds2 baths— sq ft
1331 Leonard Rd Unit B-2, Highlands, NC 28741
3D WALKTHROUGH
$289,000
3 beds1 bath— sq ft
8388 Buck Creek Rd, Highlands, NC 28741
3D WALKTHROUGH
$3,900,000
6 beds5.5 baths6,284 sq ft
6435 Buck Creek Rd, Highlands, NC 28741
3D WALKTHROUGH
$1,950,000
4 beds4.5 baths— sq ft
343 Cullasaja Dr, Highlands, NC 28741
$829,000
2 beds2 baths— sq ft
107 Chestnut Cv Unit 1D, Highlands, NC 28741
$609,500
1 bed1 bath— sq ft
49 & 50 Chestnut Walk, Highlands, NC 28741
See all

Provided by Redfin

Sale history for 434 Whiteside Mountain Rd

Year

Property tax

Land + Additions

Assessment*

2026

$5,940 (+4.4%)

$1,750,000

2025

$5,688 (−7.1%)

$1,750,000

2024

$6,121

$550,000 + $918,890

$1,468,890

2023

$6,121

$550,000 + $918,890

$1,468,890

2022

$6,121 (+5.4%)

$550,000 + $918,890

$1,468,890

2021

$5,809 (−1.5%)

$550,000 + $918,890

$1,468,890

2020

$5,897 (+1.2%)

$550,000 + $918,890

$1,468,890

2019

$5,825

$550,000 + $861,060

$1,411,060

2018

$5,825 (+2.5%)

$550,000 + $861,060

$1,411,060

2017

$5,684

$550,000 + $861,060

$1,411,060

2016

$5,684 (+11.5%)

$550,000 + $861,060

$1,411,060

2014

$5,097

$587,740 + $1,195,210

$1,782,950

Tax history for 434 Whiteside Mountain Rd

Year

Property tax

Land + Additions

Assessment*

2026

$5,940 (+4.4%)

$1,750,000

2025

$5,688 (−7.1%)

$1,750,000

2024

$6,121

$550,000 + $918,890

$1,468,890

2023

$6,121

$550,000 + $918,890

$1,468,890

2022

$6,121 (+5.4%)

$550,000 + $918,890

$1,468,890

2021

$5,809 (−1.5%)

$550,000 + $918,890

$1,468,890

2020

$5,897 (+1.2%)

$550,000 + $918,890

$1,468,890

2019

$5,825

$550,000 + $861,060

$1,411,060

2018

$5,825 (+2.5%)

$550,000 + $861,060

$1,411,060

2017

$5,684

$550,000 + $861,060

$1,411,060

2016

$5,684 (+11.5%)

$550,000 + $861,060

$1,411,060

2014

$5,097

$587,740 + $1,195,210

$1,782,950

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

3.67 Acres

Year renovated

1992

Sq. Ft.

4,470

Year built

1942

Style

Single Family Residential

County

Jackson County

APN

7561-02-0565

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 9, 2026.

Property details

Parking

Parking/Garage Information
# of Covered Spaces: 2
Has Carport
# of Carport Spaces: 2
Parking Features: Carport, Other, Paved, Parking Lot

Interior

Bathroom Information
# of Full Bathrooms: 5
# of Half Bathrooms: 2

Heating & Cooling
Has Cooling
Cooling: Ceiling Fan(s)
Has Heating
Heating: Central

Interior Features
Interior Features: Wet Bar, Built-in Features, Tray Ceiling(s), Ceiling Fan(s), Eat-in Kitchen, Kitchen Island, Pantry, Vaulted Ceiling(s), Walk-In Closet(s), Wired for Sound, High Speed Internet
Window Features: Skylight(s), Window Treatments
Furnished: Furnished
Appliances: Dryer, Dishwasher, Exhaust Fan, Disposal, Gas Oven, Refrigerator, Washer
Flooring: Tile, Wood
Has Fireplace
Fireplace Features: Basement, Gas Log, Kitchen, Living Room, Outside, Wood Burning, Master Bedroom

Room Information
Has Basement
Basement Details: Exterior Entry, Full, Finished, Interior Entry, Bath/Stubbed

Exterior

Exterior Features
Exterior Features: Garden, Other
Patio And Porch Features: Rear Porch, Covered, Deck, Front Porch, Other, Screened
Roof: Other, Slate

Building Information
Levels: Three Or More
Construction Materials: Stone, Wood Siding

Property Features
Waterfront Features: Pond
Has View
Other Structures: Shed(s)

Property Information
Property Type: Residential
Property Sub Type: Single Family Residence
Raw Mls Property Sub Type: Single Family Residence

Lot Information
Lot Features: Rolling Slope
Road Surface Type: Paved
Lot Size : 4.22
Lot Size Area: 4.22
Lot Size Units: Acres
Lot Size Acres: 4.22

Financial

Tax Information
Tax Annual Amount: $6,854.07

Utilities

Utility Information
Water Source: Well
Utilities: Cable Available
Sewer: Septic Tank

Location

Location Information
Directions: From Highlands take HWY 64 toward Cashiers. Turn right onto Whiteside Mountain Road. The home will be on your left #434. Look for the stone columns and the gate. Active alarm and cameras - no driveby's
Subdivision Name: None

Public facts

Beds: 4
Baths: 4.5
Sq. Ft.: 4,470
Stories: 1.0
Lot Size: 3.67 acres
Style: Single Family Residential
Year Built: 1942
Year Renovated: 1992
County: Jackson County
APN: 7561-02-0565

Home facts updated by county records on Oct 9, 2026

Other

Listing Information
List AOR: HighlandsCashiersBoardOfRealtors
AttributionContact: 8285268300

Around this home

Schools

K - 12
Preschool & daycare

Blue Ridge School

Public PreK-6 • Assigned • 3.2mi

5/10

Blue Ridge Virtual Early College

Public 7-12 • Assigned • 3.2mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

1/10 Heat Factor

5 days above 92° expected this year, 13 days in 30 years

2/10 Wind Factor

Minor risk of severe winds over next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Highlands, NC • 28741

Average low and high temperatures (°F)

40°

23°

50°

31°

59°

40°

66°

48°

66°

52°

74°

60°

78°

64°

71°

59°

69°

55°

61°

45°

56°

39°

47°

31°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 4.6 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.80M – $4.60M

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Nearby similar homes

NEW 22 HRS AGO3D WALKTHROUGH

$4,250,000

4 beds3.5 baths— sq ft

34 Bear Mor Ridge Rdg, Highlands, NC 28741

Landscaped grounds • 0.87 acre lot • 2 garage spots

$3,750,000

5 beds5 baths— sq ft

75 Creekwood Ct, Highlands, NC 28741

Mountain retreat • Long-range views • Timber-frame style

$1,395,000

3 beds2 baths— sq ft

711 Flat Mountain Rd, Highlands, NC 28741

Modernist design • Custom woodwork • Private setting

$2,995,000

4 beds4.5 baths— sq ft

25 Big Creek Ln, Highlands, NC

Custom finishes • Native wood • Stone fireplaces

3D WALKTHROUGH

$950,000

2 beds2 baths— sq ft

132 Rock Face Trl, Highlands, NC 28741

Covered deck • Hot tub deck • Screened porch

3D WALKTHROUGH

$1,250,000

3 beds3 baths2,067 sq ft

57 Jackson Dr, Highlands, NC 28741

New construction • Boutique community • Large island

New listings for sale in 28741

NEW 22 HRS AGO3D WALKTHROUGH

$4,250,000

4 beds3.5 baths— sq ft

34 Bear Mor Ridge Rdg, Highlands, NC 28741

Landscaped grounds • 0.87 acre lot • 2 garage spots

$1,200,000

3 beds2.5 baths— sq ft

16 Cowee Ridge Trl, Highlands, NC 28741

Paved roads • Primary bedroom • Library office

3D WALKTHROUGH

$1,100,000

3 beds2 baths— sq ft

85 Ralph Thomas Rd, Highlands, NC 28741

Private setting • Large open deck • Granite countertops

3D WALKTHROUGH

$1,950,000

8 beds5 baths— sq ft

230 Moon Mountain Rd, Highlands, NC 28741

Mountain views • Expansive grounds • 10.63 acre lot

3D WALKTHROUGH

$999,000

3 beds2 baths— sq ft

1331 Leonard Rd Unit B-2, Highlands, NC 28741

$250 HOA • Built 1981 • Listed 8 days

3D WALKTHROUGH

$289,000

3 beds1 bath— sq ft

8388 Buck Creek Rd, Highlands, NC 28741

Renovated home • Level land • Grassy lawn

3D WALKTHROUGH

$3,900,000

6 beds5.5 baths6,284 sq ft

6435 Buck Creek Rd, Highlands, NC 28741

Two homes • Breathtaking acres • 10.52 acre lot

3D WALKTHROUGH

$1,950,000

4 beds4.5 baths— sq ft

343 Cullasaja Dr, Highlands, NC 28741

Mirror lake views • Walkable location • Historic charm

$829,000

2 beds2 baths— sq ft

107 Chestnut Cv Unit 1D, Highlands, NC 28741

Spacious rear deck • Updated kitchen • Sunroom

Home values near 434 Whiteside Mountain Rd

Data from public records.

Address	Redfin Estimate
464 Whiteside Mountain Road, Highlands, NC 5 Beds \| 3 Baths \| 3958 Sq. Ft.	$2,908,599
300 Whiteside Mountain Road, Highlands, NC 3 Beds \| 3 Baths \| 4343 Sq. Ft.	$2,551,882
463 Whiteside Mountain Road, Highlands, NC 6 Beds \| 5 Baths \| 4296 Sq. Ft.	$2,082,449
441 Whiteside Mountain Road, Highlands, NC 3 Beds \| 4 Baths \| 4048 Sq. Ft.	$1,974,806
395 Whiteside Mountain Road, Highlands, NC 3 Beds \| 3.5 Baths \| - Sq. Ft.	$1,982,583
910 Country Club Drive, Highlands, NC 4 Beds \| 3 Baths \| - Sq. Ft.	$2,261,809
933 Country Club Drive, Highlands, NC 3 Beds \| 3 Baths \| 2195 Sq. Ft.	$1,349,415

Address	Redfin Estimate
560 Whiteside Mountain Road, Highlands, NC 3 Beds \| 5 Baths \| 4772 Sq. Ft.	$3,178,573
230 Whiteside Mountain Road, Highlands, NC 5 Beds \| 5 Baths \| 4049 Sq. Ft.	$2,300,887
331 Whiteside Mountain Road, Highlands, NC 4 Beds \| 4.5 Baths \| 3354 Sq. Ft.	$2,173,830
360 Whiteside Mountain Road, Highlands, NC - Beds \| 1 Baths \| 384 Sq. Ft.	$1,094,224
393 Whiteside Mountain Road, Highlands, NC 4 Beds \| 3.5 Baths \| - Sq. Ft.	$2,740,491
8 Hickory Lane, Highlands, NC 3 Beds \| 3.5 Baths \| 2116 Sq. Ft.	$902,901
933 Country Club Drive, Highlands, NC 4 Beds \| 4.5 Baths \| 4604 Sq. Ft.	$2,245,277

Address	Redfin Estimate
404 Whiteside Mountain Road, Highlands, NC 7 Beds \| 4.5 Baths \| - Sq. Ft.	$4,835,288
505 Whiteside Mountain Road, Highlands, NC 3 Beds \| 3.5 Baths \| - Sq. Ft.	$2,464,517
495 Whiteside Mountain Road, Highlands, NC 3 Beds \| 3.5 Baths \| - Sq. Ft.	$2,007,301
505 Whiteside Mountain Road, Highlands, NC 3 Beds \| 3.5 Baths \| 3550 Sq. Ft.	$2,111,012
395 Whiteside Mountain Road, Highlands, NC 4 Beds \| 3.5 Baths \| 4184 Sq. Ft.	$2,299,398
933 Country Club Drive, Highlands, NC 3 Beds \| 3 Baths \| - Sq. Ft.	$1,341,372
937 Country Club Drive, Highlands, NC 5 Beds \| 4.5 Baths \| 5536 Sq. Ft.	$2,485,921

Property information provided by HCMLS when last listed in 2023. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 28741, NC

Sale history for 434 Whiteside Mountain Rd

Tax history for 434 Whiteside Mountain Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 28741

Home values near 434 Whiteside Mountain Rd

More real estate resources