Incredible and rare opportunity in Winston, Oregon! Developers, investors, and visionaries take notice. This charming 1940s 2-bedroom, 1-bath home is full of character and ready for its next chapter. With a little vision and elbow grease, this property offers endless possibilities.Situated on a spacious, level lot with mature greenery, the property presents potential for future development, including the possibility of 1–2 additional homes surrounding the existing residence (buyer to perform due diligence with local authorities). Whether you’re looking for a primary residence, rental property, fix-and-flip opportunity, or future development project, this property checks all the boxes.Located on a quiet street near the middle school, community center, and local park, you’ll appreciate the convenience of this desirable location while enjoying the peaceful neighborhood setting.Opportunities like this don’t come along often—bring your ideas and unlock the potential of this unique Winston property!
Active
$205,000
381 SE Gregory Dr, Winston, OR 97496
2beds
1,323sqft
Residential, Single Family Residence
Built in 1948
0.61 Acres Lot
$-- Zestimate®
$155/sqft
$-- HOA
What's special
Mature greenerySpacious level lotFull of characterQuiet street
- 36 days |
- 1,156 |
- 45 |
Zillow last checked:
Listing updated:
Listed by:
Shae Ellison 541-733-0986,
Platinum Realty
Source: RMLS (OR),MLS#: 452974190
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
- Main level bathrooms: 1
Rooms
- Room types: Bedroom 2, Dining Room, Family Room, Kitchen, Living Room, Primary Bedroom
Primary bedroom
- Level: Main
Heating
- Floor Furnace
Features
- Basement: Crawl Space
- Fireplace features: Insert, Wood Burning
Interior area
- Total structure area: 1,323
- Total interior livable area: 1,323 sqft
Video & virtual tour
Property
Parking
- Parking features: Driveway, Off Street, Detached
- Has uncovered spaces: Yes
Features
- Levels: One
- Stories: 1
Lot
- Size: 0.61 Acres
- Features: SqFt 20000 to Acres1
Details
- Parcel number: R53183
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Residential, Single Family Residence
Materials
- Shake Siding
- Roof: Shingle
Condition
- Resale
- New construction: No
- Year built: 1948
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Winston
Financial & listing details
- Price per square foot: $155/sqft
- Tax assessed value: $219,056
- Annual tax amount: $3,080
- Date on market: 6/1/2026
- Listing terms: Cash,Conventional,Rehab
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/2/2026 | Listed for sale | $205,000-2.3%$155/sqft |
Source:  RMLS (OR) #452974190 Report a problem | ||
| 1/28/2026 | Sold | $209,800$159/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $2,006 +2.9% | $120,610 +3% |
| 2023 | $1,950 +3.1% | $117,098 +3% |
| 2022 | $1,892 +2.8% | $113,688 +3% |
| 2021 | $1,841 +3% | $110,377 +3% |
| 2020 | $1,787 +2.4% | $107,163 +3% |
| 2019 | $1,745 +2.8% | $104,042 +3% |
| 2018 | $1,698 | $101,012 +3% |
| 2017 | $1,698 +5.5% | $98,070 +3% |
| 2016 | $1,609 | $95,214 +3% |
| 2015 | $1,609 +4.9% | $92,441 +3% |
| 2014 | $1,535 | $89,749 +3% |
| 2013 | $1,535 +6.2% | $87,135 +3% |
| 2012 | $1,445 +3.6% | $84,598 +3% |
| 2011 | $1,395 +2.8% | $82,134 +3% |
| 2010 | $1,356 +3.9% | $79,742 +3% |
| 2009 | $1,306 +3.1% | $77,420 +3% |
| 2008 | $1,266 +3.5% | $75,166 +3% |
| 2007 | $1,223 +2.6% | $72,977 +3% |
| 2006 | $1,192 +3.1% | $70,852 +3% |
| 2005 | $1,156 +4.8% | $68,789 +6.1% |
| 2003 | $1,103 +2.9% | $64,841 +3% |
| 2002 | $1,072 | $62,953 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 97496
Nearby schools
GreatSchools rating
- 7/10Mcgovern Elementary SchoolGrades: 3-5Distance: 0.6 mi
- 4/10Winston Middle SchoolGrades: 6-8Distance: 0.3 mi
- 5/10Douglas High SchoolGrades: 9-12Distance: 1.3 mi
Schools provided by the listing agent
- Elementary: Mcgovern
- Middle: Winston
- High: Douglas
Source: RMLS (OR). This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Oregon
- Douglas County
- Winston
- 97496
- 381 SE Gregory Dr
Nearby cities
Nearby zip codes
Other Winston Topics
