Skip to content
Skip to content
TopHapOpen in map
Single Family ResidenceResidential
$284,895$223 / ft²
TopHap EstimateOur estimate of what this home would sell for today, based on nearby sales, the home's size and features, and local price trends. It is a starting point, not an appraisal.· confidence 92How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Sep 24, 2026
Last sold for $288,000 on Mar 31, 2022

20 NE GREGORY DR

WINSTON, OR 97496
1
Beds
2
Baths
1,276 ft²
Living AreaTotal finished area of the structures, from county records. Some counties include shared space like hallways or a building gym, so it may not match a listing.
0.15 ac
Lot SizeThe size of the land the home sits on, from county records.
1955
Year BuiltThe year the home was originally built, according to county records.
2
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$285K
$261K low$308K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$288,000 · Mar 31, 2022

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$3,457 (2025)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$135,677 (2025)
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$131,726
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$247,953

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
CountyDOUGLAS
Effective Year BuiltAn adjusted build year that accounts for condition and major remodels. A big renovation can make a home count as newer than it is.1965
Lot (acres)The size of the land the home sits on, from county records.0.15
RoofThe main material covering the roof, such as asphalt shingle or tile.Composition Shingle
HeatingThe type of heating system in the home.Heat Pump
CoolingThe type of cooling or air conditioning in the home.Yes
FireplaceWhether the home has a fireplace, and what kind.Yes
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(3)

Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.

Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.

M
Winston Middle SchoolD-
Middle · Grades 6–8 · 0.6 mi
H
Douglas High SchoolC-
High · Grades 9–12 · 1.4 mi
E
Brockway Elementary SchoolD-
Elementary · Grades PK–2 · 1.6 mi

District: Winston-Dillard School District 116

Neighborhood · ZIP 97496These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.

CrimeLocal crime compared with the rest of the country, where 100 is average. It reflects things like population density, income, and how crime gets reported.125
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.117
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.190

Index scale: 100 = US average (tick). Lower is better.

Homes occupiedThe share of homes here that someone lives in. The rest sit empty, including vacation and for-sale homes.95%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.9.6%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.16%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.2%
PopulationHow many people live in this area.7,529
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.56 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$55,451
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$71,529
Average tempThe average temperature here across a full year.52°F
Annual precipHow much rain and melted snow falls here in a typical year.43 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.48%

Owner Tools

Do you own this home?
Claim this home

Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.

How this home compares

20 Ne Gregory Dr measured against every home in its neighborhood, its ZIP code and its county, using county assessor records refreshed nightly. A home can stand out in one of those areas and look ordinary in another, because each one holds a different mix of homes.

  • Worth less than 66% of homes in Douglas County
  • Has a smaller lot than 87% of homes in Douglas County
  • Older than 78% of homes in Winston 97496

What homes are worth in Winston 97496

Each bar is how many homes fall in that price range. The marker is this home.

This home
$138K$656K

This home is worth more than 39% of homes in Winston 97496.

How it measures up in Winston 97496

The dot is this home. The mark in the middle is the typical home in Winston 97496.

Estimated value$284,895
CheaperTypical $312,435Pricier

Pricier than 39% of homes nearby

Price per ft²$223
CheaperTypical $234Pricier

Pricier than 40% of homes nearby

Living area1,276 ft²
SmallerTypical 1,404 ft²Bigger

Bigger than 38% of homes nearby

Lot size0.15 ac
SmallerTypical 0.24 acBigger

Bigger than 15% of homes nearby

Year built1955
OlderTypical 1981Newer

Newer than 22% of homes nearby

How 20 Ne Gregory Dr ranks against every home in each area.
MeasureThis homeWinston 97496Douglas County
Estimated valuepricier than$284,89539% of homes34% of homes
Price per ft²pricier than$22340% of homes40% of homes
Living areabigger than1,276 ft²38% of homes37% of homes
Lot sizebigger than0.15 ac15% of homes13% of homes
Year builtnewer than195522% of homes29% of homes

About 20 Ne Gregory Dr

How much is 20 Ne Gregory Dr, Winston, OR worth?

The TopHap Estimate for 20 Ne Gregory Dr, Winston, OR is $284,895 as of Sep 24, 2026. The likely range is $261,461 to $308,329. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 20 Ne Gregory Dr, Winston, OR last sell?

20 Ne Gregory Dr, Winston, OR last sold on Mar 31, 2022 for $288,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 20 Ne Gregory Dr, Winston, OR?

20 Ne Gregory Dr, Winston, OR has 1 bedrooms, 2 bathrooms, 1,276 square feet of living space and a 0.15-acre lot.

When was 20 Ne Gregory Dr, Winston, OR built?

20 Ne Gregory Dr, Winston, OR was built in 1955, making it 71 years old.

What schools serve 20 Ne Gregory Dr, Winston, OR?

20 Ne Gregory Dr, Winston, OR is assigned to Winston Middle School (middle), rated D-; Douglas High School (high), rated C-; Brockway Elementary School (elementary), rated D-. All sit in Winston-Dillard School District 116. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 20 Ne Gregory Dr, Winston, OR compare to other homes in Winston 97496?

Among the 2,509 homes in Winston 97496, it is worth more than 39% of them ($284,895 against a typical $312,435), its price per square foot is higher than 40% of them ($223 against a typical $234), it is bigger than 38% of them (1,276 ft² against a typical 1,404 ft²), its lot is bigger than 15% of them (0.15 ac against a typical 0.24 ac) and it is newer than 22% of them (1955 against a typical 1981). Measured against all of Douglas County, it is worth more than 34% of homes there. These shares are recounted nightly from the full county assessor record for each area, not from active listings.

What are the property taxes on 20 Ne Gregory Dr, Winston, OR?

The 2025 property tax bill for 20 Ne Gregory Dr, Winston, OR was $3,457. The county assessed it at $135,677.

More homes on Ne Gregory Dr

Closest homes

More homes in Winston 97496

Assigned schools

Explore the area

See this home in context

Open 20 Ne Gregory Dr on TopHap’s interactive map to compare it against every sale nearby, overlay school zones and flood risk, and run a CMA.

Open in map
A flyover of TopHap's photorealistic 3D map, with recorded sale prices pinned to homes
Search any address, city, zip, or county…3D$1.9M$6.25MOpen in map