Douglas County property records for 53 addresses on Upper Olalla Rd, Winston, OR · Last verified August 2026
| Properties | 53 |
|---|---|
| Median Sale Price | $375,000 |
| Deeds and Mortgages on File | 37 |
| Median Price per Sqft | $189 |
| Owner Occupied | 75% |
| Median Annual Tax Bill | $1,059 |
| Median Year Built | 1981 |
| Median Ownership Tenure | 8 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
0.439 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jan 2000 | 1 Name on Record Owner Occupied | AssessorUpdated Feb 2026 |
3 bd · 2 ba · 1,296 sqft · 4.11 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $50,000Feb 1992 | $8412025 | 2 Names on Record Owner Occupied | AssessorUpdated Feb 2026 |
3 bd · 2 ba · 1,640 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,827Mar 2014 | $4,7682025 | Amount on Record Aug 2004 | 2 Names on Record Owner Occupied | AssessorUpdated Feb 2026 |
2.81 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $55,000Feb 2000 | $1442025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Feb 2026 |
3 bd · 2 ba · 1,520 sqft · 2.43 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $300,000Mar 2019 | $2,6772025 | Amount on Record Oct 2018 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Feb 2026 |
3 bd · 1 ba · 924 sqft · 4.86 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $312025 | 1 Name on Record Owner Occupied | AssessorUpdated Mar 2026 |
3 bd · 2 ba · 1,008 sqft · 1.01 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $170,000Feb 2023 | $6682025 | —Aug 2016 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Feb 2026 |
1 bd · 1 ba · 588 sqft · 96.5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Mar 2015 | $2,6062025 | 2 Names on Record | AssessorUpdated Feb 2026 |
1.28 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $375,000Aug 2025 | $482025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Feb 2026 |
3 bd · 3 ba · 2,446 sqft · 11.5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $380,000Feb 2020 | $2332025 | Amount on Record Oct 2017 | 2 Names on Record | Assessor + 1 DocumentUpdated Feb 2026 |
3 bd · 2 ba · 2,230 sqft · 10 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,5692025 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 3 ba · 2,174 sqft · 5.7 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $325,000May 2018 | $2292025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Feb 2026 |
3 bd · 1 ba · 1,755 sqft · 2.1 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —May 2016 | $1602025 | 1 Name on Record Owner Occupied | AssessorUpdated Feb 2026 |
1 bd · 1 ba · 1,092 sqft · 5.53 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Apr 2013 | $1172025 | 1 Name on Record Owner Occupied | AssessorUpdated Feb 2026 |
3 bd · 2 ba · 1,296 sqft · 2.1 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3642025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 1 ba · 1,359 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,7812025 | 1 Name on Record Owner Occupied | AssessorUpdated Feb 2026 |
2 bd · 2.5 ba · 2,720 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jun 2007 | $6,4522025 | —Feb 2007 | 1 Name on Record Owner Occupied | AssessorUpdated Jul 2026 |
4 bd · 3 ba · 2,129 sqft · 2.15 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $425,000Aug 2025 | $1,4522025 | Amount on Record Jul 2015 | 1 Name on Record | AssessorUpdated Jun 2026 |
2 bd · 2 ba · 1,376 sqft · 28.6 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,3342025 | —Feb 2004 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Feb 2026 |
3 bd · 2 ba · 2,124 sqft · 5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,109,000Oct 2024 | $4,5732025 | —May 2022 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Jun 2026 |
3 bd · 2 ba · 2,314 sqft · 5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $101,000May 2022 | $7452025 | Amount on Record Feb 2004 | 1 Name on Record | AssessorUpdated May 2026 |
3 bd · 2 ba · 2,010 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $285,000Apr 2021 | $2,6252025 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
3 bd · 1 ba · 1,690 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $282,400Sep 2007 | $2,1462025 | —Jun 2007 | 2 Names on Record Owner Occupied | AssessorUpdated Aug 2026 |
2 bd · 2 ba · 2,128 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —May 2019 | $2,5092025 | Amount on Record May 2019 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Feb 2026 |
3 bd · 2 ba · 1,056 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $283,500Oct 2016 | $1322025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Mar 2026 |
2 bd · 1 ba · 672 sqft · 5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,500Aug 1986 | $122025 | 2 Names on Record Owner Occupied | AssessorUpdated Mar 2026 |
3 bd · 2 ba · 1,782 sqft · 2.71 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2512025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Mar 2026 |
5.03 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $339,000Jan 2019 | $1072025 | —Mar 2017 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Feb 2026 |
1 ba · 750 sqft · 4.9 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $235,000May 2021 | $1,9552025 | Amount on Record Aug 2017 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Feb 2026 |
2.65 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $425,000Sep 2025 | $1512025 | 2 Names on Record Owner Occupied | AssessorUpdated Feb 2026 |
3 bd · 2 ba · 1,393 sqft · 3.33 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $445,000May 2025 | $2,4662025 | Amount on Record May 2021 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
3 bd · 2 ba · 1,620 sqft · 6.33 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $125,000Nov 1997 | $942025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Feb 2026 |
3 bd · 2 ba · 1,740 sqft · 4.91 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $330,000May 2020 | $1722025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Feb 2026 |
3 bd · 2 ba · 1,188 sqft · 8.71 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $255,000Dec 2017 | $32025 | 2 Names on Record | AssessorUpdated May 2026 |
4 bd · 2 ba · 3,414 sqft · 5.65 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Apr 2015 | $812025 | 1 Name on Record Owner Occupied | AssessorUpdated Feb 2026 |
3 bd · 2 ba · 1,752 sqft · 10 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,2122025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,491 sqft · 2.53 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $83,500Jan 2006 | $1,6272025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Feb 2026 |
640 sqft · Built 1974 · 5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $190,000Oct 2018 | $1,1072025 | 2 Names on Record Owner Occupied | AssessorUpdated Feb 2026 |
3 bd · 1 ba · 1,832 sqft · 5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $190,000Oct 2018 | $1,2622020 | —Sep 1999 | 2 Names on Record | Assessor + 1 DocumentUpdated Jun 2023 |
2 bd · 1 ba · 672 sqft · 1.61 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $205,000Nov 2018 | $702025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Mar 2026 |
3 bd · 2 ba · 1,568 sqft · 5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $185,000Oct 2007 | $1,0592025 | 1 Name on Record Owner Occupied | AssessorUpdated Feb 2026 |
1 bd · 3 ba · 2,496 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,2732025 | Amount on Record Sep 2015 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Aug 2026 |
2.51 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $175,000Jun 2002 | $852025 | 1 Name on Record Owner Occupied | AssessorUpdated Feb 2026 |
3 bd · 2 ba · 2,804 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $75,000Oct 1989 | $2,0122020 | 1 Name on Record | AssessorUpdated Jun 2023 |
3 bd · 1 ba · 1,601 sqft · 3.11 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $169,000May 2024 | $1,2372025 | —Mar 2014 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Jun 2026 |
3 bd · 2 ba · 1,584 sqft · 5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jun 2013 | $1,6672025 | 1 Name on Record | AssessorUpdated Feb 2026 |
2 bd · 1 ba · 552 sqft · 33.5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $682025 | 1 Name on Record | AssessorUpdated Mar 2026 |
3 bd · 2 ba · 1,188 sqft
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3192020 | 1 Name on Record | AssessorUpdated Jun 2023 |
3 bd · 2 ba · 1,842 sqft · 5 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $525,000Sep 2022 | $2,9552025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Jun 2026 |
2,000 sqft · Built 1983 · 0.45 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Apr 2001 | 1 Name on Record Owner Occupied | AssessorUpdated Feb 2026 |
3 bd · 1 ba · 1,326 sqft · 5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $43,350Jul 1987 | $1,2312025 | 1 Name on Record | AssessorUpdated Feb 2026 |
3 bd · 2.5 ba · 2,304 sqft · 5 acres · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $363,500May 2018 | $2,8532025 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
2 bd · 2 ba · 1,392 sqft · 20.5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $5612025 | —Aug 2010 | 1 Name on Record | Assessor + 1 DocumentUpdated Feb 2026 |
Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020
| Wildfire Risk | High this street's cells rank at the 86th percentile of exposed land nationally · 65th in Oregon |
|---|---|
| Wildfire Likelihood | High — about 1 in 123 per year |
| Exposure | Direct 31 of 35 cells directly exposed · 35 adjoin burnable vegetation |