1999 Upper Dr, Highlands, NC 28741
Property image
Property image
OFF MARKET

$1,924,900

Trulia Estimate
  • 3 Beds
  • 3.5 Baths

1999 Upper Dr, Highlands, NC 28741

Est. Refi. Payment $10,392/mo*
Refinance Your Home
Currently Off Market - Sold May 16, 2023 for $1,675,000

Home Value

Trulia Estimate
$1.93M
Since last month
Increased$11K (+0.6%)
Since last year
Increased$59K (+3.1%)
Since last sale
Increased$251K (+15%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +144% in the last 10 years
MonthEstimated value
2026
August 2026$1.93M
August 2026$1.92M
July 2026$1.91M
June 2026$1.88M
May 2026$1.91M
April 2026$2.01M
March 2026$2M
February 2026$1.98M
January 2026$1.92M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
140 Lost Trl #145, Highlands, NC
0.26
Single-Family Home
$1,625,000
01/30/26
3
3
2,576
140 Lost Trl, Highlands, NC
0.27
Single-Family Home
$1,625,000
01/30/26
3
3
-
88 Lost Trl, Highlands, NC
0.24
Single-Family Home
$2,275,000
10/29/25
3
3.5
-
88 Lost Trl #143, Highlands, NC
0.25
Single-Family Home
$2,275,000
10/29/25
3
3.5
4,194
224 Lost Trail, Highlands, NC
0.28
Single-Family Home
$2,800,000
10/20/25
3
3.5
-
2147 Bowery Road, Highlands, NC
0.46
Single-Family Home
$2,135,000
08/14/26
3
4.5
-
2050 Cullasaja Club Drive, Highlands, NC
0.45
Single-Family Home
$2,622,000
03/19/26
4
4.5
-
2130 Falcon Ridge, Highlands, NC
0.43
Single-Family Home
$2,950,000
04/10/26
4
4.5
-
87 Salt Rock Ct, Highlands, NC
0.45
Single-Family Home
$4,025,000
05/04/26
4
5
2,379
108 W View Way #113, Highlands, NC
0.76
Single-Family Home
$2,600,000
10/23/25
4
3.5
3,027

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1982 Upper Divide Road, Highlands, NC 28741
0.05
$3,431,700
5
5.5
-
Off Market
n/a Tanner Loop, Highlands, NC 28741
0.10
$450,000
-
-
-
Recently Sold
Lot #8 Falcon Ridge Road, Highlands, NC 28741
0.15
-
-
-
-
Off Market
2141 Upper Divide Road, Highlands, NC 28741
0.13
$4,850,000
5
5.5
-
For Sale
50 Rock Creek Drive, Highlands, NC 28741
0.19
$1,332,000
3
3
-
Off Market
2162 Upper Divide Road, Highlands, NC 28741
0.15
$3,291,200
4
4.5
-
Off Market
TBD Falcon Ridge, Highlands, NC 28741
0.17
-
-
-
-
Off Market
Lot 2 Hardscrabble Ridge Road, Highlands, NC 28741
0.16
$1,100,000
-
-
-
For Sale
764 Hardscrabble Ridge Road, Cashiers, NC 28741
0.17
$4,997,000
4
5.5
-
For Sale
1740 Upper Divide Road, Highlands, NC 28741
0.21
$1,776,200
3
3
-
Off Market
1471 Falcon Ridge, Highlands, NC 28741
0.23
$1,732,300
3
3
-
Off Market
178/179* Lost Trail, Highlands, NC 28741
0.22
$2,225,800
4
4
-
Off Market

Local Information

  • Map ViewExplore the area around 1999 Upper Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1999
Lot Size
0.77 acres

About this House

Look no further for a country club home that's easy to maintain and just big enough for your needs. Three bedrooms, three and one-half baths, all on one level, with wood floors, beautiful stone fireplace, and a dream kitchen for cooks with breakfast nook. Imagine sitting on the spacious deck, just relaxing to the sounds of the birds and the vision of the rock face of Whiteside before you. Come in from the spacious two-car garage, past the laundry and office area, into the open kitchen and great room. Custom built for the previous owner, this home is well constructed to last and last. Enjoy cozy moments in the summer or year round with central heat and air. This home has been in a vacation rental program for several years. Many of the lovely furnishings are available to buy outside the sale.
1999 Upper Dr, Highlands, NC 28741 is a 3 bedroom, 4 bathroom single-family home built in 1999. It last sold for $1,675,000 on May 16, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,924,900, with a rent estimate of $4,384/month.

Home Details for 1999 Upper Dr

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Types of Rooms: Pantry
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Wood

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Lot Information

Lot Area: 0.77 acres

Price and Tax history

DateEventPrice
May 16, 2023
Source: N/A
Sold
$1,675,000
Sep 10, 2020
Source: N/A
Sold
$885,000
Jul 28, 2020
Source: Agent Provided
Pending
$895,000
Jun 17, 2020
Source: Agent Provided
PriceChange
$895,000
Price decreased by 6%
Jul 18, 2019
Source: Agent Provided
Listed For Sale
$950,000

Market trends in Highlands

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
191
5MoM

Around this home

What Locals Say about Highlands

At least 19 Trulia users voted on each feature.

  • 95 % Say it's dog friendly

  • 91 % Say it's quiet

  • 89 % Say car is needed

  • 89 % Say yards are well-kept

  • 84 % Say people would walk alone at night

  • 76 % Say there's holiday spirit

  • 74 % Say parking is easy

  • 74 % Say they plan to stay for at least 5 years

  • 74 % Say there's wildlife

  • 74 % Say there are community events

  • 54 % Say neighbors are friendly

  • 52 % Say streets are well-lit

  • 46 % Say kids play outside

  • 44 % Say it's walkable to grocery stores

  • 30 % Say it's walkable to restaurants

  • 25 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Kimberlyg833
    "It’s beautiful and appears to be a great place to raise a family. I used to come here as a child back in the 70’s with my parents and it’s still as I remember it. Quaint and beautiful. "
    15
    Flag
  • Karie.mcclure
    "not sure only a renter at this point but love how safe And low key it is .. great weather as well nice people "
    2
    Flag
  • Pam
    "Great small town. Elevation 4000 feet plus. Friendly residents. Lots to do for a small town. A little pricy, but worth it. Great hiking and waterfalls galore. Dog friendly neighborhood and town."
    7
    Flag
  • Christine B.
    "It's a very friendly community. When the tourists come to town for the season it gets overcrowded but some non locals are really friendly. "
    6
    Flag
  • Bill B.
    "I live here and love the weather, hiking trails, water falls, and the National Forest. 4,118 feet elevation provides cool weather in the summer."
    3
    Flag
  • Susan C.
    "What a beautiful place to live ... there is nothing as peaceful or beautiful as the mountains and this lovely, quaint town."
    3
    Flag
  • Rick C.
    "There's no Wal-Mart or fast food joints. Life in the mountains has an easier pace. You are removed from the city, but that's why we live here, to get away from it all. There is a world class spa, fine dining on smaller scale, exquisite shops. Think Breckinridge, without the skiing.Beautiful mountains, hiking, mountain biking, floral life, live music, plays, wineries, what more do you want?"
    2
    Flag
  • carolrosen
    "Great area, lovely home, easy comfortable living"
    3
    Flag
  • John D.
    "A great place to spend the summer, and within walking distance to town."
    3
    Flag
  • Nadine P.
    "A wonderful community with a year round caretaker, pool, tennis courts and swimming pool plus it is gated. Certainly not a necessity in Highlands! I would recommend King Mtn to anyone looking for lush foliage, fantastic views and wonderful amenities."
    0
    Flag
  • Nadine P.
    "I have lived in Highlands, NC for 7 years and still upon returning from out of town get a peacefulness when I hit Main St or the Gorge Rd from Franklin. Prettiest place anywhere...you must visit!"
    0
    Flag
  • Dorothy S.
    "You will find that people are extremely friendly. We have four mild seasons. Winter is wonderful. Nothing is better than curling up with a book in front of a crackling fire."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 1999 Upper Dr

  • What is 1999 Upper Dr estimated to be worth?
    Trulia's estimated value for 1999 Upper Dr in Highlands, NC is $1,924,900.
  • What is the price history for 1999 Upper Dr?
    1999 Upper Dr in Highlands, NC last sold for $1,675,000 in May 2023.
  • Is Highlands a buyer's or seller's market?
    Highlands is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Highlands?
    Residents describe Highlands, NC as dog-friendly, quiet, and well-kept. Most residents say you need a car. See recently sold homes in Highlands, NC.
  • Does 1999 Upper Dr have air conditioning?
    Yes, 1999 Upper Dr in Highlands, NC has air conditioning.
  • Does 1999 Upper Dr have laundry facilities?
    Yes, 1999 Upper Dr in Highlands, NC has in-unit laundry.

Explore by feature - Air Conditioning

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Off Market Homes Near 1999 Upper Dr

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