Photo: Visitor7 · CC BY-SA 3.065 homes sold in Winston in the last year, at a typical $328K
Almost every sale is a house. Below: what each kind of home sells for, what your budget buys, the best months to buy, how hard you’ll have to bid, and a shortcut to every site where Winston homes are listed.
Every place Winston homes are listed, in one stop
We don’t copy listings: the agents’ sites have the photos and the latest price changes. Set what you want once and we open each site already filtered to Winston.
For sale
Rent
New, land & open houses
Links open the listing sites; TownRatings isn’t paid for them and doesn’t rank one above another. Rentals and government-owned homes come from sources outside the MLS.
Houses are 97% of Winston’s sales, at a typical $326K
65 homes sold in the year to May 2026.
typical sale · 63 sold in 12 months
- Per square foot
- $231OR $296
- Days to sell
- 63
- Sold over asking
- 17%
- Listings with a price cut
- 32%
Townhouses: 2 sold, typical $385K
Too few sales in 12 months for reliable figures.
Fewer homes sell than before 2022, at twice the 2016 price
65 sales in the last year, against 123 in 2021 and a low of 44 in 2014. The typical sale went from $169K in 2016 to $328K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $350K buys in Winston
Check a listing against what Winston homes sold for
Against the town’s median price per square foot over the last 12 months. A rough check: condition, lot and location within town move a price more than this can see.
Bidding wars in Winston are back to pre-pandemic levels, with about as many homes for sale
We read every month of Winston’s home sales since 2012 so you don’t have to. Each figure covers 12 months, because a single month in a town is too few sales to mean much. Latest: the year to May 2026, 65 sales.
If you’re buying in Winston
- Shop in June. It brings about 10 new listings a month, close to the busiest month, with fewer bidding wars (19% over asking).
- You can negotiate. 33% of listings have cut their price, against 19% before the pandemic.
- Bid near asking. Buyers paid 98% of the list price on average; 18% paid over.
- You’ll usually have time. Only 19% of homes go under contract within two weeks; the typical one takes 65 days.
Spring brings the homes; fall brings the bidding wars
May has the most new listings (about 12 a month), but September is the most competitive: 35% of September sales close over asking. February has the least competition (18%).
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and calmer than Oregon
| Winston now | 2017–19 | 2021 peak | OR now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 18% | 23% | 43% | 24% |
| Gone within two weeksShare of homes under contract within 14 days | 19% | 31% | 60% | 31% |
| Listings with a price cutShare of homes for sale that cut their price | 33% | 19% | 19% | 30% |
| Price paid vs. askingAverage sale price ÷ list price | 98% | 98.8% | 99.7% | 98.8% |
| Days to sellMedian days from listing to contract | 65 | 38 | 16 | 46 |
19 homes for sale on a typical day
That’s 1.5 times the 2021 low (12), 14% fewer than in 2017–19 and well under 2012’s 29.
1 in 3 listings has cut its price
33% in the last year, against 19% in 2017–19 and 30% across Oregon. More sellers are pricing high and coming down.
Winston ranks 79th of 109 busy Oregon markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Winston is in the middle of the pack.
Source: Redfin Data Center, city market tracker, January 2012 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Winston home costs about $1,953 a month
Price: Winston’s typical sale, last 12 months. Property tax at Winston’s 0.9% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Winston is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in May
The month with the most choice. December has the fewest, about 6.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $328K home, about $2,900 a year.
Taxes vs. neighborsSchools
The schools grade for Winston, from test results, graduation and how much students grow.
Schools in WinstonCheck the flood map
Flood insurance isn’t in a standard policy, and lenders require it in FEMA flood zones. Check the address before you make an offer.
Natural hazardsLook up any property
Assessed value, lot size and every past sale of a home you’re eyeing are public, at the town or county assessor and the registry of deeds.
Green, Roseburg and Roseburg North sell for less a square foot
The busier markets within 25 miles of Winston, by what sold. Prices, taxes and how far a paycheck goes next door are on Cost of living.
| Sold | Typical sale | $/sq ft | Over asking | Days to sell | |
|---|---|---|---|---|---|
| Roseburg | 312 | $331K | $223 | 15% | 33 |
| Sutherlin | 101 | $380K | $251 | 20% | 50 |
| Green | 76 | $330K | $224 | 13% | 68 |
| Winston | 65 | $328K | $232 | 18% | 65 |
| Myrtle Creek | 40 | $301K | $234 | 27% | 64 |
| Roseburg North | 32 | $518K | $225 | 6% | 97 |
| Tri-City | 24 | $289K | $234 | 38% | 74 |
Redfin Data Center, June 2025 to May 2026. Towns with fewer than 20 sales are left out, and Redfin doesn’t report every town separately.
Post your home to Winston, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Winston. People who follow the town see it, and so do people comparing Winston with their own town. No commission, no listing fee.
Questions about buying a home in Winston
What do homes sell for in Winston, OR?
65 homes sold in the year to May 2026 at a typical $328K, $232 a square foot.
Is Winston a buyer’s or seller’s market?
A seller’s market: 15 homes were for sale in May 2026 and 6 sold, about 2.5 months of supply. Buyers paid 98% of asking on average, and 33% of listings cut their price.
When is the best time to buy in Winston?
May brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Winston?
About 0.9% of a home’s value a year. On a $328K home that’s near $2,900.
Where can I see homes for sale in Winston?
Zillow, Redfin, Realtor.com and Homes.com all carry Winston’s MLS listings; the search links above open each one filtered to Winston.
Sales, prices, days on market and listings: Redfin Data Center (MLS, monthly, not seasonally adjusted). Property tax rate: Census American Community Survey. Two-bedroom rent: HUD Fair Market Rent. Typical home value: Zillow Home Value Index. Schools grade: TownRatings (how grades work).