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Single Family ResidenceResidential
$281,950$210 / 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 91How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Oct 21, 2026
Last sold for $90,000 on Feb 4, 2014

21 NE GREGORY DR

WINSTON, OR 97496
3
Beds
2
Baths
1,344 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.
0.2 ac
Lot SizeThe size of the land the home sits on, from county records.
1970
Year BuiltThe year the home was originally built, according to county records.
1
StoriesHow many floors the home has above ground.
2
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$282K
$257K low$306K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$90,000 · Feb 4, 2014

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$2,601 (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.$156,492 (2025)
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$151,934
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$261,355

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.1973
Lot (acres)The size of the land the home sits on, from county records.0.20
FoundationWhat the home is built on, such as a concrete slab, a crawl space, or a basement.Mat/Raft Foundation (Slab)
RoofThe main material covering the roof, such as asphalt shingle or tile.Composition Shingle
HeatingThe type of heating system in the home.Forced Air
CoolingThe type of cooling or air conditioning in the home.Central
FireplaceWhether the home has a fireplace, and what kind.Yes
GarageWhether the property has a garage, and details like whether it is attached to the home.Garage, Attached
ViewThe type of view from the property, or another feature of the site that affects value.Yes - Type Unknown
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Deck · 240 ft²

Transaction History(2)

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

Foreclosure Filings(1)

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

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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

21 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 67% of homes in Douglas County
  • Costs less per square foot than 70% of homes in Douglas County
  • Has a smaller lot than 70% of homes in Douglas County
  • Older than 69% 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
$132K$631K

This home is worth more than 40% 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$281,950
CheaperTypical $309,950Pricier

Pricier than 40% of homes nearby

Price per ft²$210
CheaperTypical $229Pricier

Pricier than 33% of homes nearby

Living area1,344 ft²
SmallerTypical 1,404 ft²Bigger

Bigger than 45% of homes nearby

Lot size0.2 ac
SmallerTypical 0.24 acBigger

Bigger than 39% of homes nearby

Year built1970
OlderTypical 1980Newer

Newer than 31% of homes nearby

How 21 Ne Gregory Dr ranks against every home in each area.
MeasureThis homeWinston 97496Douglas County
Estimated valuepricier than$281,95040% of homes33% of homes
Price per ft²pricier than$21033% of homes30% of homes
Living areabigger than1,344 ft²45% of homes42% of homes
Lot sizebigger than0.2 ac39% of homes30% of homes
Year builtnewer than197031% of homes41% of homes

About 21 Ne Gregory Dr

How much is 21 Ne Gregory Dr, Winston, OR worth?

The TopHap Estimate for 21 Ne Gregory Dr, Winston, OR is $281,950 as of Oct 21, 2026. The likely range is $257,407 to $306,493. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 21 Ne Gregory Dr, Winston, OR last sell?

21 Ne Gregory Dr, Winston, OR last sold on Feb 4, 2014 for $90,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 21 Ne Gregory Dr, Winston, OR?

21 Ne Gregory Dr, Winston, OR has 3 bedrooms, 2 bathrooms, 1,344 square feet of living space and a 0.20-acre lot.

When was 21 Ne Gregory Dr, Winston, OR built?

21 Ne Gregory Dr, Winston, OR was built in 1970, making it 56 years old. The building has 1 story.

What schools serve 21 Ne Gregory Dr, Winston, OR?

21 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 21 Ne Gregory Dr, Winston, OR compare to other homes in Winston 97496?

Among the 2,469 homes in Winston 97496, it is worth more than 40% of them ($281,950 against a typical $309,950), its price per square foot is higher than 33% of them ($210 against a typical $229), it is bigger than 45% of them (1,344 ft² against a typical 1,404 ft²), its lot is bigger than 39% of them (0.2 ac against a typical 0.24 ac) and it is newer than 31% of them (1970 against a typical 1980). Measured against all of Douglas County, it is worth more than 33% 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 21 Ne Gregory Dr, Winston, OR?

The 2025 property tax bill for 21 Ne Gregory Dr, Winston, OR was $2,601. The county assessed it at $156,492.

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