8161 Upper Olalla Rd, Winston, OR 97496
OFF MARKET

$617,000

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,910 sqft (on 5 acres)

8161 Upper Olalla Rd, Winston, OR 97496

Est. Refi. Payment $3,589/mo*
Refinance Your Home

Home Value

Trulia Estimate
$617K
Since last month
Increased$1K (+0.2%)
Since last year
Increased$10K (+1.6%)
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 +58% in the last 10 years
MonthEstimated value
2026
August 2026$617K
August 2026$616K
July 2026$616K
June 2026$604K
May 2026$608K
April 2026$596K
March 2026$589K
February 2026$589K
January 2026$591K
2025
2024
2023
2022

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
7941 Upper Olalla Rd, Winston, OR
0.18
Single-Family Home
$425,000
09/12/25
3
2
2,167
270 Sabrina Ln, Winston, OR
0.46
Single-Family Home
$400,000
05/04/26
2
2
1,040
800 Byron Creek Rd, Winston, OR
0.92
Single-Family Home
$450,000
07/30/26
3
3
1,320
164 Moon Hill Rd, Tenmile, OR
4.29
Single-Family Home
$400,000
02/25/26
3
2
1,848
164 Moonhill Rd, Roseburg, OR
4.28
Single-Family Home
$400,000
02/25/26
3
1
1,030
320 Rays Ln, Tenmile, OR
5.47
Single-Family Home
$535,000
07/07/26
3
2
1,794
1052 Reston Rd, Roseburg, OR
5.09
Single-Family Home
$380,000
10/28/25
3
2
1,404

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
7941 Upper Olalla Rd, Winston, OR 97496
0.18
$417,700
3
2
2,167
Off Market
7950 Upper Olalla Rd, Winston, OR 97496
0.20
-
3
2
1,393
Off Market
1680 Byron Creek Rd, Winston, OR 97496
0.42
$379,800
2
1
1,333
Off Market
Upper Olalla Rd, Winston, OR 97496
0.39
-
-
-
-
Off Market
1950 Byron Creek Rd, Winston, OR 97496
0.48
$629,900
4
2
1,920
Off Market
270 Sabrina Ln, Winston, OR 97496
0.46
$400,000
2
1
1,040
Recently Sold
1941 Byron Creek Rd, Winston, OR 97496
0.64
$469,900
2
2
1,764
For Sale
660 Byron Creek Rd, Winston, OR 97496
0.79
$348,400
3
2
1,808
Off Market
736 Byron Creek Rd, Winston, OR 97496
0.84
$463,200
3
2
1,767
Off Market
800 Byron Creek Rd, Winston, OR 97496
0.92
$450,000
3
2
1,320
Recently Sold
901 Byron Creek Rd, Winston, OR 97496
0.98
$392,700
3
2
1,650
Off Market
6910 Upper Olalla Rd, Winston, OR 97496
1.05
$1,072,600
3
2
3,564
Off Market

Local Information

  • Map ViewExplore the area around 8161 Upper Olalla Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2021
5 acre lot
1,910 sqft
$323/sqft
Garage

About this House

This single-family home is located at 8161 Upper Olalla Rd, Winston, OR. 8161 Upper Olalla Rd is in Winston, OR and in ZIP code 97496. This property has 2 bedrooms, 2 bathrooms and approximately 1,910 sqft of floor space. This property has a lot size of 5.00 acres and was built in 2021.
8161 Upper Olalla Rd, Winston, OR 97496 is a 2 bedroom, 2 bathroom, 1,910 sqft single-family home built in 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $617,000, with a rent estimate of $2,429/month.

Home Details for 8161 Upper Olalla Rd

Interior Features

Heating & Cooling
Heating: Heat PumpHeating Fuel: Heat Pump
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Concrete, Hardwood

Exterior Features

Exterior Home Features
Roof: CompositionExterior: ShingleFoundation Type: Concrete
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 2021
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 5.00 acres

Price and Tax history

YearProperty taxTax assessment
2025
$4,185
$623,994
Home facts updated by county records

Market trends in Winston

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
40
1MoM

Around this home

What Locals Say about Winston

At least 37 Trulia users voted on each feature.

  • 98 % Say yards are well-kept

  • 98 % Say it's dog friendly

  • 89 % Say parking is easy

  • 87 % Say car is needed

  • 76 % Say there's holiday spirit

  • 73 % Say kids play outside

  • 68 % Say there's wildlife

  • 67 % Say it's quiet

  • 62 % Say there are sidewalks

  • 60 % Say neighbors are friendly

  • 57 % Say they plan to stay for at least 5 years

  • 56 % Say it's walkable to grocery stores

  • 55 % Say it's walkable to restaurants

  • 53 % Say people would walk alone at night

  • 51 % Say streets are well-lit

  • 23 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Amy
    "I just moved here in December of 2018. So far, the neighbors are friendly, and the police frequently roam around town to show their presence. "
    1
    Flag
  • Trulia User
    "An alleged shooting happened recently on Jorgens street next door to a house pending sale. Otherwise for the most part not a bad neighborhood just a few bad houses. Drugs...."
    10
    Flag
  • Sissyboy2011
    "That there are thieves and tweekers everywhere. Watch out at the parks for needles and the streets. Lock up everything you keep outside including your vehicles. Kids bikes get stolen daily. most of the time WPD is running a skeleton crew. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 8161 Upper Olalla Rd

  • What is 8161 Upper Olalla Rd estimated to be worth?
    Trulia's estimated value for 8161 Upper Olalla Rd in Winston, OR is $617,000.
  • Is Winston a buyer's or seller's market?
    Winston is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winston?
    Residents describe Winston, OR as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Winston, OR.
  • What are the closest schools to 8161 Upper Olalla Rd?
    The closest schools to 8161 Upper Olalla Rd in Winston, OR are Douglas High School (rated 5/10), Lookingglass Elementary School (Pre-K, rated 6/10), Mcgovern Elementary School (rated 7/10).
  • How big is the lot at 8161 Upper Olalla Rd?
    The lot at 8161 Upper Olalla Rd in Winston, OR is about 5 acres.
  • Does 8161 Upper Olalla Rd have a garage?
    Yes, 8161 Upper Olalla Rd in Winston, OR has a garage.

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 8161 Upper Olalla Rd

Skip to last item
Skip to first item

Homes for sale near 8161 Upper Olalla Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item