5905 Upper Olalla Rd, Winston, OR 97496
OFF MARKET

$670,800

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 2,403 sqft (on 5 acres)

5905 Upper Olalla Rd, Winston, OR 97496

Est. Refi. Payment $3,894/mo*
Refinance Your Home
Currently Off Market - Sold Oct 7, 2016 for $525,000

Home Value

Trulia Estimate
$671K
Since last month
Decreased$9K (-1.3%)
Since last year
Increased$600 (+0.1%)
Since last sale
Increased$147K (+27.9%)
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 decreased by -15% in the last 10 years
MonthEstimated value
2026
August 2026$672K
August 2026$671K
July 2026$680K
June 2026$681K
May 2026$680K
April 2026$669K
March 2026$644K
February 2026$630K
January 2026$626K
2025
2024
2023
2022
2021

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
1.38
Single-Family Home
$425,000
09/12/25
3
2
2,167
270 Sabrina Ln, Winston, OR
2.00
Single-Family Home
$400,000
05/04/26
2
2
1,040
800 Byron Creek Rd, Winston, OR
2.42
Single-Family Home
$450,000
07/30/26
3
3
1,320
164 Moonhill Rd, Roseburg, OR
2.74
Single-Family Home
$400,000
02/25/26
3
1
1,030
164 Moon Hill Rd, Tenmile, OR
2.75
Single-Family Home
$400,000
02/25/26
3
2
1,848
320 Rays Ln, Tenmile, OR
3.92
Single-Family Home
$535,000
07/07/26
3
2
1,794
1052 Reston Rd, Roseburg, OR
3.57
Single-Family Home
$380,000
10/28/25
3
2
1,404
1868 Larson Rd, Roseburg, OR
6.89
Single-Family Home
$675,000
08/14/26
4
2
2,088

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
0.70
$1,050,000
3
2
2,720
For Sale
6910 Upper Olalla Rd, Winston, OR 97496
0.87
$1,072,600
3
2
3,564
Off Market
740 Ireland Rd, Winston, OR 97496
1.27
$199,000
-
-
-
For Sale
7941 Upper Olalla Rd, Winston, OR 97496
1.38
$417,700
3
2
2,167
Off Market
7950 Upper Olalla Rd, Winston, OR 97496
1.38
-
3
2
1,393
Off Market
1950 Byron Creek Rd, Winston, OR 97496
1.49
$629,900
4
2
1,920
Off Market
Ireland Rd, Winston, OR 97496
1.56
-
-
-
-
Off Market
1941 Byron Creek Rd, Winston, OR 97496
1.53
$469,900
2
2
1,764
For Sale

Local Information

  • Map ViewExplore the area around 5905 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 1940
5 acre lot
2,403 sqft
$279/sqft

About this House

This single-family home is located at 5905 Upper Olalla Rd, Winston, OR. 5905 Upper Olalla Rd is in Winston, OR and in ZIP code 97496. This property has 3 bedrooms, 1 bathroom and approximately 2,403 sqft of floor space. This property has a lot size of 5.00 acres and was built in 1940.
5905 Upper Olalla Rd, Winston, OR 97496 is a 3 bedroom, 1 bathroom, 2,403 sqft single-family home built in 1940. It last sold for $525,000 on Oct 7, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $670,800, with a rent estimate of $1,895/month.

Home Details for 5905 Upper Olalla Rd

Interior Features

Interior Details
BasementIn-law unit
Heating & Cooling
Heating: BaseboardAir ConditioningHeating Fuel: Baseboard
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Other, Carpet, Concrete

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherFoundation Type: Concrete

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 5.00 acres

Price and Tax history

DateEventPrice
Oct 7, 2016
Source: N/A
Sold
$525,000

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 5905 Upper Olalla Rd

  • What is 5905 Upper Olalla Rd estimated to be worth?
    Trulia's estimated value for 5905 Upper Olalla Rd in Winston, OR is $670,800.
  • What is the price history for 5905 Upper Olalla Rd?
    5905 Upper Olalla Rd in Winston, OR last sold for $525,000 in October 2016.
  • 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 5905 Upper Olalla Rd?
    The lot at 5905 Upper Olalla Rd in Winston, OR is about 5 acres.

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