5489 Upper Olalla Rd
Winston, OR 97496
3 Beds
2 Baths
70 sqft (on 1.01 acres)
3 Beds
2 Baths
70 sqft
(on 1.01 acres)
Local Information
- Map ViewExplore the area around 5489 Upper Olalla Rd.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1980
Lot Size
1.01 acres
Living Area
70 sqft
Price/Sqft
$3,260
About this House
This single-family home is located at 5489 Upper Olalla Rd, Winston, OR. 5489 Upper Olalla Rd is in Winston, OR and in ZIP code 97496. This property has 3 bedrooms, 2 bathrooms and approximately 70 sqft of floor space. This property has a lot size of 1.01 acres and was built in 1980.
5489 Upper Olalla Rd, Winston, OR 97496 is a 3 bedroom, 2 bathroom, 70 sqft single-family home built in 1980. It is currently off market. The Trulia Estimate is $228,200, with a rent estimate of $2,191/month.
Home Details for 5489 Upper Olalla Rd
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Year Built Year Built: 1980 |
Property Type / Style Property Type: Single Family Home |
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Exterior Home Features Deck |
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Lot Area: 1.01 acres |
Market trends in Winston
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
39
2MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $669 |
| Assessment | $119,263 |
Home facts updated by county records
Comparable Sales for 5489 Upper Olalla Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
1.20 | Single-Family Home | $425,000 | 08/05/25 | 4 | 3 | 2,129 | |
1.44 | Single-Family Home | $650,000 | 08/08/25 | 3 | 2 | 2,600 | |
1.90 | Single-Family Home | $425,000 | 09/12/25 | 3 | 2 | 2,167 | |
2.27 | Single-Family Home | $400,000 | 02/25/26 | 3 | 2 | 1,848 | |
2.25 | Single-Family Home | $400,000 | 02/25/26 | 3 | 1 | 1,030 | |
1.96 | Single-Family Home | $640,000 | 08/08/25 | 4 | 2 | 1,920 | |
2.53 | Single-Family Home | $400,000 | 05/04/26 | 2 | 2 | 1,040 | |
3.10 | Single-Family Home | $380,000 | 10/28/25 | 3 | 2 | 1,404 | |
2.92 | Single-Family Home | $450,000 | 07/30/26 | 3 | 3 | 1,320 | |
3.39 | Single-Family Home | $535,000 | 07/07/26 | 3 | 2 | 1,794 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALE
3D VIEW5 ACRESReal Broker, Active
OFF MARKETKeller Williams Southern Oregon-Umpqua Valley, Sold
OFF MARKETEngel & Volkers West Portland, Sold
OFF MARKETAmy Dean Real Estate, Inc., Sold
Assigned Schools
These are the assigned schools for 5489 Upper Olalla Rd.
- Mcgovern Elementary School
- 3-5
- Public
- 229 Students
7/10GreatSchools RatingParent Rating AverageMy son has struggled in other schools, he often was pushed aside and strung along. He is now flourishing and exceeding standards I did not think was possible. His teacher is absolutely amazing, she has this way about her that just appeals to him I suppose, and she has so much patience and compassion about her job!Parent Review8y ago - Lookingglass Elementary School
- PK-5
- Public
- 131 Students
6/10GreatSchools RatingParent Rating AverageA 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 Review16y ago - Winston Middle School
- 6-8
- Public
- 310 Students
4/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Douglas High School
- 9-12
- Public
- 357 Students
5/10GreatSchools RatingParent Rating AverageThis school has horrible sportsmanship. Year after year when volleyball teams play against Douglas at their home court, their student body harasses the other team. They call the girls pigs and tell them they look like boys. These girls are left in tears. What does the staff do? Nothing. Something needs to be done. So if you don't want to send your child to a school with bullies do not send them here!Other Review6y ago 
Check out schools near 5489 Upper Olalla Rd.
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.
LGBTQ Local Legal Protections
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Apartments for Rent
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Homes for sale near 5489 Upper Olalla Rd
FOR SALE BY OWNER
FOR SALE BY OWNER
FOR SALE BY OWNER105 ACRES
2.08 ACRESCurrieco Real Estate, Active
4.95 ACRESKeller Williams Southern Oregon-Umpqua Valley, Active
See more homes for sale inWinston
Off Market Homes Near 5489 Upper Olalla Rd
SOLDJUN 11, 2026Pacific Properties, Sold
SOLDJAN 27, 2026
SOLDJAN 16, 2026Cutting Edge Real Estate, Sold- OFF MARKET
- See more homes for sale inWinston
