5491 Upper Olalla Rd, Winston, OR 97496
OFF MARKET

$457,100

Trulia Estimate
  • 2 Beds
  • 1,704 sqft (on 5 acres)

5491 Upper Olalla Rd, Winston, OR 97496

Est. Refi. Payment $2,639/mo*
Refinance Your Home
Currently Off Market - Sold Jul 15, 2022 for $215,000

Home Value

Trulia Estimate
$457K
Since last month
Increased$12K (+2.6%)
Since last year
Increased$11K (+2.5%)
Since last sale
Increased$245K (+113.9%)
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 +99% in the last 10 years
MonthEstimated value
2026
August 2026$460K
August 2026$457K
July 2026$448K
June 2026$453K
May 2026$453K
April 2026$463K
March 2026$458K
February 2026$455K
January 2026$450K
2025
2024
2023
2019
2018
2017

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
1.81
Single-Family Home
$425,000
09/12/25
3
2
2,167
270 Sabrina Ln, Winston, OR
2.44
Single-Family Home
$400,000
05/04/26
2
2
1,040
164 Moon Hill Rd, Tenmile, OR
2.36
Single-Family Home
$400,000
02/25/26
3
2
1,848
164 Moonhill Rd, Roseburg, OR
2.34
Single-Family Home
$400,000
02/25/26
3
1
1,030
800 Byron Creek Rd, Winston, OR
2.83
Single-Family Home
$450,000
07/30/26
3
3
1,320
1052 Reston Rd, Roseburg, OR
3.19
Single-Family Home
$380,000
10/28/25
3
2
1,404
320 Rays Ln, Tenmile, OR
3.49
Single-Family Home
$535,000
07/07/26
3
2
1,794
1868 Larson Rd, Roseburg, OR
6.44
Single-Family Home
$675,000
08/14/26
4
2
2,088
4321 Happy Valley Rd, Roseburg, OR
8.16
Single-Family Home
$827,000
01/09/26
3
2
1,926

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
740 Ireland Rd, Winston, OR 97496
0.95
$199,000
-
-
-
For Sale
6700 Upper Olalla Rd, Winston, OR 97496
0.97
$1,050,000
3
2
2,720
For Sale
6910 Upper Olalla Rd, Winston, OR 97496
1.18
$1,072,600
3
2
3,564
Off Market
Ireland Rd, Winston, OR 97496
1.37
-
-
-
-
Off Market
1260 Ireland Rd, Winston, OR 97496
1.49
$637,100
3
2
2,600
Off Market

Local Information

  • Map ViewExplore the area around 5491 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 2022
5 acre lot
1,704 sqft
$268/sqft

About this House

This single-family home is located at 5491 Upper Olalla Rd, Winston, OR. 5491 Upper Olalla Rd is in Winston, OR and in ZIP code 97496. This property has 2 bedrooms and approximately 1,704 sqft of floor space. This property has a lot size of 5.00 acres and was built in 2022.
5491 Upper Olalla Rd, Winston, OR 97496 is a 2 bedroom, 1,704 sqft single-family home built in 2022. It last sold for $215,000 on Jul 15, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $457,100, with a rent estimate of $2,357/month.

Home Details for 5491 Upper Olalla Rd

Interior Features

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

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherFoundation Type: Concrete

Property Information

Year Built
Year Built: 2022
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 5.00 acres

Price and Tax history

DateEventPrice
Jul 15, 2022
Source: N/A
Sold
$215,000

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 5491 Upper Olalla Rd

  • What is 5491 Upper Olalla Rd estimated to be worth?
    Trulia's estimated value for 5491 Upper Olalla Rd in Winston, OR is $457,100.
  • What is the price history for 5491 Upper Olalla Rd?
    5491 Upper Olalla Rd in Winston, OR last sold for $215,000 in July 2022.
  • 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.
  • How big is the lot at 5491 Upper Olalla Rd?
    The lot at 5491 Upper Olalla Rd in Winston, OR is about 5 acres.

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