5897 Upper Olalla Rd, Winston, OR 97496
Property image
Property image
OFF MARKET

$430,300

Trulia Estimate
  • 5 Beds
  • 2 Baths
  • 1,812 sqft (on 22.01 acres)

5897 Upper Olalla Rd, Winston, OR 97496

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Home Value

Trulia Estimate
$430K
Since last month
Increased$7K (+1.6%)
Since last year
Decreased$8K (-1.9%)
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 +244% in the last 10 years
MonthEstimated value
2026
September 2026$424K
August 2026$417K
July 2026$407K
June 2026$463K
May 2026$452K
April 2026$429K
March 2026$416K
February 2026$382K
January 2026$409K
2025
2024
2023
2022
2021
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
164 Moon Hill Rd, Tenmile, OR
2.40
Single-Family Home
$400,000
02/25/26
3
2
1,848
270 Sabrina Ln, Winston, OR
2.41
Single-Family Home
$400,000
05/04/26
2
2
1,040
164 Moonhill Rd, Roseburg, OR
2.38
Single-Family Home
$400,000
02/25/26
3
1
1,030
800 Byron Creek Rd, Winston, OR
2.80
Single-Family Home
$450,000
07/30/26
3
3
1,320
1052 Reston Rd, Roseburg, OR
3.23
Single-Family Home
$380,000
10/28/25
3
2
1,404
320 Rays Ln, Tenmile, OR
3.51
Single-Family Home
$535,000
07/07/26
3
2
1,794
1868 Larson Rd, Roseburg, OR
6.46
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
6700 Upper Olalla Rd, Winston, OR 97496
0.94
$1,050,000
3
2
2,720
For Sale
740 Ireland Rd, Winston, OR 97496
0.99
$199,000
-
-
-
For Sale
6910 Upper Olalla Rd, Winston, OR 97496
1.14
$1,061,200
3
2
3,564
Off Market
Ireland Rd, Winston, OR 97496
1.41
-
-
-
-
Off Market
1260 Ireland Rd, Winston, OR 97496
1.53
$624,000
3
2
2,600
Off Market

Local Information

  • Map ViewExplore the area around 5897 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 1951
22.01 acre lot
1,812 sqft
$237/sqft

About this House

Absolutely beautiful property with year round Olalla Creek & irrigation rights. Trees around the home are giant and majestic, excellent gardening and plant growing soil. Home is adorable on the outside with steep Asymmetrical roof lines, unique for the area. Interior is warm and inviting, needs updating. Irrigation equipment and pump included.
5897 Upper Olalla Rd, Winston, OR 97496 is a 5 bedroom, 2 bathroom, 1,812 sqft single-family home built in 1951. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $430,300, with a rent estimate of $2,452/month.

Home Details for 5897 Upper Olalla Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 2Floors: Linoleum Vinyl
Interior Details
Types of Rooms: Dining Room
Appliances & Utilities
DryerWasher

Property Information

Year Built
Year Built: 1951
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Exterior Features

Exterior Home Features
Exterior: Other

Lot Information

Lot Area: 22.01 acres

Price and Tax history

DateEventPrice
Nov 10, 2018
Source: Agent Provided
ListingRemoved
$320,000
Nov 7, 2018
Source: Agent Provided
PriceChange
$320,000
Price decreased by 3%
Oct 12, 2018
Source: Agent Provided
PriceChange
$330,000
Price decreased by 3%
Sep 12, 2018
Source: Agent Provided
PriceChange
$340,000
Price decreased by 3%
Jul 11, 2018
Source: Agent Provided
Listed For Sale
$350,000

Market trends in Winston

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
37
3MoM

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 5897 Upper Olalla Rd

  • What is 5897 Upper Olalla Rd estimated to be worth?
    Trulia's estimated value for 5897 Upper Olalla Rd in Winston, OR is $430,300.
  • 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 5897 Upper Olalla Rd?
    The closest schools to 5897 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).
  • Does 5897 Upper Olalla Rd have laundry facilities?
    Yes, 5897 Upper Olalla Rd in Winston, OR has in-unit laundry.
  • How big is the lot at 5897 Upper Olalla Rd?
    The lot at 5897 Upper Olalla Rd in Winston, OR is about 22 acres.

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Winston, OR

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Off Market Homes Near 5897 Upper Olalla Rd

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