1999 Upper Dr, Highlands, NC 28741
OFF MARKET

1999 Upper Dr
Highlands, NC 28741

  • 3 Beds
  • 3.5 Baths

$1,911,200

Trulia Estimate
as of Jun 14, 2026
Est. Refi. Payment $10,118/mo*
Refinance Your Home

$1,911,200

Trulia Estimate
as of Jun 14, 2026
Est. Refi. Payment $10,118/mo*
Refinance Your Home
3 Beds
3.5 Baths
(on 0.77 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 1999 Upper Dr

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningCooling System: CentralHeating Fuel: Other
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 History for 1999 Upper Dr

DatePriceEventSource
05/16/2023$1,675,000Sold
N/A
09/10/2020$885,000Sold
N/A
07/28/2020$895,000PendingAgent Provided
06/17/2020$895,000PriceChange
Agent Provided
07/18/2019$950,000Listed For SaleAgent Provided
10/28/2015$750,000Sold
N/A

Market trends in Highlands

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
161
11MoM
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Property Tax and Assessment

Year2024
Tax$5,081
Assessment$972,850
Home facts updated by county records

Homeowner tools

Estimated monthly rent$5,915/mo
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Homes for rent near 1999 Upper Dr

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Comparable Sales for 1999 Upper Dr

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
-
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
108 W View Way, Highlands, NC
0.76
Single-Family Home
$2,600,000
10/23/25
4
3.5
3,027

Nearby homes

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Assigned Schools

These are the assigned schools for 1999 Upper Dr.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Homes for sale near 1999 Upper Dr

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Off Market Homes Near 1999 Upper Dr

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1999 Upper Dr, Highlands, NC 28741 is a 3 bedroom, 4 bathroom single-family home built in 1999. This property is not currently available for sale. 1999 Upper Dr was last sold on May 16, 2023 for $1,675,000. The current Trulia Estimate for 1999 Upper Dr is $1,911,200.