Are yards well-kept in Winston, OR?

As of early 2026, 98% of users say yards are well-kept

Is Winston, OR dog-friendly?

As of early 2026, 98% of users say it's dog friendly

Is parking easy in Winston, OR?

As of early 2026, 89% of users say parking is easy

Is a car needed in Winston, OR?

As of early 2026, 87% of users say car is needed

Does Winston, OR show holiday spirit?

As of early 2026, 76% of users say there's holiday spirit

Do kids play outside in Winston, OR?

As of early 2026, 73% of users say kids play outside

Is there wildlife in Winston, OR?

As of early 2026, 68% of users say there's wildlife

Is Winston, OR quiet?

As of early 2026, 67% of users say it's quiet

Does Winston, OR have sidewalks?

As of early 2026, 62% of users say there are sidewalks

Are neighbors friendly in Winston, OR?

As of early 2026, 60% of users say neighbors are friendly

Do residents of Winston, OR plan to stay at least 5 years?

As of early 2026, 57% of users say they plan to stay for at least 5 years

Is Winston, OR walkable to grocery stores?

As of early 2026, 56% of users say it's walkable to grocery stores

Is Winston, OR walkable to restaurants?

As of early 2026, 55% of users say it's walkable to restaurants

Would people walk alone at night in Winston, OR?

As of early 2026, 53% of users say people would walk alone at night

Are the streets well-lit in Winston, OR?

As of early 2026, 51% of users say streets are well-lit

Are there community events in Winston, OR?

As of early 2026, 23% of users say there are community events

What is 6044 Upper Olalla Rd estimated to be worth?

Trulia's estimated value for 6044 Upper Olalla Rd in Winston, OR is $614,400 .

What is the price history for 6044 Upper Olalla Rd?

6044 Upper Olalla Rd in Winston, OR last sold for $376,000 in October 2017.

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 6044 Upper Olalla Rd?

The lot at 6044 Upper Olalla Rd in Winston, OR is about 16.5 acres .

Does 6044 Upper Olalla Rd have a garage?

Yes, 6044 Upper Olalla Rd in Winston, OR has a garage.

OFF MARKET

$614,400

Trulia Estimate

3 Beds
3 Baths
2,446 sqft (on 5 acres)

6044 Upper Olalla Rd, Winston, OR 97496

Est. Refi. Payment $3,557/mo*

Refinance Your Home

Currently Off Market - Sold Oct 23, 2017 for $376,000

Home Value

Trulia Estimate

$614K

Since last month

$6K (-1%)

Since last year

$7K (-1.2%)

Since last sale

$240K (+63.7%)

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 +109% in the last 10 years

Month	Estimated value
2026
August 2026	$616K
August 2026	$615K
July 2026	$622K
June 2026	$625K
May 2026	$628K
April 2026	$617K
March 2026	$605K
February 2026	$606K
January 2026	$593K
2025
December 2025	$597K
November 2025	$610K
October 2025	$611K
September 2025	$613K
August 2025	$623K
July 2025	$632K
June 2025	$631K
May 2025	$621K
April 2025	$614K
March 2025	$614K
February 2025	$601K
January 2025	$597K
2024
December 2024	$603K
November 2024	$606K
October 2024	$591K
September 2024	$591K
August 2024	$632K
July 2024	$642K
June 2024	$629K
May 2024	$621K
April 2024	$624K
March 2024	$618K
February 2024	$605K
January 2024	$592K
2023
December 2023	$604K
November 2023	$586K
October 2023	$615K
September 2023	$618K
August 2023	$618K
July 2023	$614K
June 2023	$616K
May 2023	$589K
April 2023	$587K
March 2023	$590K
February 2023	$573K
January 2023	$569K
2022
December 2022	$580K
November 2022	$592K
October 2022	$602K
September 2022	$603K
August 2022	$609K
July 2022	$619K
June 2022	$621K
May 2022	$616K
April 2022	$609K
March 2022	$611K
February 2022	$573K
January 2022	$570K
2021
December 2021	$567K
November 2021	$567K
October 2021	$571K
September 2021	$568K
August 2021	$565K
July 2021	$556K
June 2021	$466K
May 2021	$358K
April 2021	$348K
March 2021	$318K
February 2021	$319K
January 2021	$314K
2020
December 2020	$354K
November 2020	$417K
October 2020	$470K
September 2020	$473K
2019
October 2019	$430K
September 2019	$427K
August 2019	$423K
July 2019	$426K
June 2019	$427K
May 2019	$424K
April 2019	$420K
March 2019	$417K
February 2019	$416K
January 2019	$416K
2018
December 2018	$410K
November 2018	$401K
October 2018	$397K
September 2018	$399K
August 2018	$397K
July 2018	$393K
June 2018	$393K
May 2018	$390K
April 2018	$396K
March 2018	$391K
February 2018	$390K
January 2018	$388K
2017
December 2017	$379K
November 2017	$378K
October 2017	$377K
September 2017	$326K
August 2017	$323K
July 2017	$322K
June 2017	$328K
May 2017	$319K
April 2017	$313K
March 2017	$313K
February 2017	$307K
January 2017	$294K

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	1.95	Single-Family Home	$425,000	09/12/25	3	2	2,167
164 Moon Hill Rd, Tenmile, OR	2.55	Single-Family Home	$400,000	02/25/26	3	2	1,848
270 Sabrina Ln, Winston, OR	2.58	Single-Family Home	$400,000	05/04/26	2	2	1,040
800 Byron Creek Rd, Winston, OR	2.85	Single-Family Home	$450,000	07/30/26	3	3	1,320
164 Moonhill Rd, Roseburg, OR	2.54	Single-Family Home	$400,000	02/25/26	3	1	1,030
320 Rays Ln, Tenmile, OR	3.49	Single-Family Home	$535,000	07/07/26	3	2	1,794
1052 Reston Rd, Roseburg, OR	3.41	Single-Family Home	$380,000	10/28/25	3	2	1,404
1868 Larson Rd, Roseburg, OR	6.28	Single-Family Home	$675,000	08/14/26	4	2	2,088
4321 Happy Valley Rd, Roseburg, OR	7.74	Single-Family Home	$827,000	01/09/26	3	2	1,926
3800 Happy Valley Rd, Roseburg, OR	8.12	Single-Family Home	$220,000	04/24/26	3	1	1,920

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	0.92	$1,050,000	3	2	2,720	For Sale
6910 Upper Olalla Rd, Winston, OR 97496	1.12	$1,072,600	3	2	3,564	Off Market
740 Ireland Rd, Winston, OR 97496	1.38	$199,000	-	-	-	For Sale
3353 Olalla Rd, Winston, OR 97496	1.45	$605,800	3	2	1,408	Off Market

Local Information

Map ViewExplore the area around 6044 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 1981

5 acre lot

2,446 sqft

$251/sqft

Garage

About this House

This single-family home is located at 6044 Upper Olalla Rd, Winston, OR. 6044 Upper Olalla Rd is in Winston, OR and in ZIP code 97496. This property has 3 bedrooms, 3 bathrooms and approximately 2,446 sqft of floor space. This property has a lot size of 16.51 acres and was built in 1981.

6044 Upper Olalla Rd, Winston, OR 97496 is a 3 bedroom, 3 bathroom, 2,446 sqft single-family home built in 1981. It last sold for $376,000 on Oct 23, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $614,400, with a rent estimate of $2,723/month.

Home Details for 6044 Upper Olalla Rd

Interior Features
Interior Details Basement
Heating & Cooling Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Floors: Carpet, Concrete

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: OtherFoundation Type: Concrete
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1981
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 5.00 acres

Price and Tax history

Date	Event	Price
Oct 23, 2017 Source: RMLS (OR) #17539315	Sold	$376,000

Year	Property tax	Tax assessment
2025	$2,482	$587,533

Additional Cost

Market trends in Winston

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Around this home

Lookingglass Elementary School
PK-5
Public
131 Students
Winston-Dillard School District 116
6/10
GreatSchools Rating
Parent Rating Average
A school is about so much more than results on standardized tests. I've attended 7 schools in my life and Lookingglass Elementary is the only one I give 10 out of 10. I truly felt cared for by the instructors at Lookingglass, on my first day (4th grade) I received aptitude testing that they effective used to target areas that I could improve on and worked with me to do so now I am three years into college Dean's List all the way. This is a great school any child would be lucky to attend, they helped to teach me morals during regular education. The schools gardening program is an exceptional concept that builds well rounded individuals. There isn't enough I can say to express my gratitude to this school and I know my sibling feels the same way.
Student Review
16y ago
1 Reviews

View nearby schools on GreatSchools

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 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
Resident
7y ago
"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
Resident
7y ago
"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
Resident
8y ago
"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 6044 Upper Olalla Rd

What is 6044 Upper Olalla Rd estimated to be worth?
Trulia's estimated value for 6044 Upper Olalla Rd in Winston, OR is $614,400.
What is the price history for 6044 Upper Olalla Rd?
6044 Upper Olalla Rd in Winston, OR last sold for $376,000 in October 2017.
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 6044 Upper Olalla Rd?
The lot at 6044 Upper Olalla Rd in Winston, OR is about 16.5 acres.
Does 6044 Upper Olalla Rd have a garage?
Yes, 6044 Upper Olalla Rd in Winston, OR has a garage.

Apartments for Rent

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Off Market Homes Near 6044 Upper Olalla Rd

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SOLD
JUL 30, 2026
$450,000
3 bd
2 ba
1,320 sqft
800 Byron Creek Rd,
Winston, OR 97496
eXp Realty, LLC, Sold
SOLD
JUL 7, 2026
$535,000
3 bd
1 ba
1,794 sqft
320 Rays Ln,
Tenmile, OR 97481
Stellar Realty Northwest, Sold
SOLD
MAY 4, 2026
$400,000
2 bd
1 ba
1,040 sqft
270 Sabrina Ln,
Winston, OR 97496
Oregon Life Homes, Sold
SOLD
MAR 13, 2026
$545,000
4 bd
3 ba
2,400 sqft
712 Sibold Canyon Rd,
Tenmile, OR 97481
Oregon Life Homes, Sold
SOLD
MAR 5, 2026
$645,000
4 bd
2 ba
2,225 sqft
982 Reston Rd,
Roseburg, OR 97471
Value Home Realty, Sold
SOLD
FEB 25, 2026
$400,000
3 bd
1 ba
1,030 sqft
164 Moonhill Rd,
Roseburg, OR 97471
SOLD
FEB 25, 2026
$400,000
3 bd
2 ba
1,848 sqft
164 Moon Hill Rd,
Tenmile, OR 97481
Real Broker, Sold
SOLD
JAN 16, 2026
$329,000
3 bd
1 ba
1,782 sqft
5189 Strickland Canyon Rd,
Roseburg, OR 97471
Cutting Edge Real Estate, Sold
OFF MARKET
3 bd
2 ba
1,600 sqft
100 Crater Rd,
Camas Valley, OR 97416
Oregon Life Homes, Sold
OFF MARKET
Est. $373,800
3 bd
2 ba
1,404 sqft
1052 Reston Rd,
Roseburg, OR 97471
Sundance Realty LLC, Sold
See more homes for sale in
Winston
Take a look

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Homes for sale near 6044 Upper Olalla Rd

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5 ACRES
$1,050,000
3 bd
3 ba
2,720 sqft
6700 Upper Olalla Rd,
Winston, OR 97496
Real Broker, Active
3.67 ACRES
$649,000
3 bd
3 ba
2,220 sqft
2950 Tenmile Valley Rd,
Tenmile, OR 97481
Lamonte Real Estate Professionals, Active
7.11 ACRES
$649,900
3 bd
2 ba
2,038 sqft
460 Little Branch Ln,
Roseburg, OR 97471
eXp Realty, LLC, Active
FOR SALE BY OWNER
$449,000
3 bd
2 ba
1,562 sqft
111 Streamside Ln,
Winston, OR 97496
FOR SALE BY OWNER
$390,000
3 bd
2 ba
1,245 sqft
754 SE Hall St,
Winston, OR 97496
20 ACRES
$190,000
1 bd
1 ba
1,000 sqft
Rice Creek Rd,
Winston, OR 97496
Starlight Realty, Active
6.32 ACRES
$680,000
4 bd
2 ba
2,240 sqft
411 Woodland Dr,
Winston, OR 97496
RE/MAX Integrity, Active
FOR SALE BY OWNER
105 ACRES
$2,225,000
3 bd
2 ba
1,643 sqft
9216 Lookingglass Rd,
Roseburg, OR 97471
4.95 ACRES
$1,100,000
3 bd
3 ba
2,969 sqft
420 Cascara Ln,
Roseburg, OR 97471
Keller Williams Southern Oregon-Umpqua Valley, Active
2.08 ACRES
$310,000
3 bd
1 ba
1,573 sqft
4341 Happy Valley Rd,
Roseburg, OR 97471
Currieco Real Estate, Active
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Winston
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