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Single Family ResidenceResidential
$231,277$224 / 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 88How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Aug 30, 2026
Last sold for $160,000 on Aug 25, 2021

421 SE GREGORY DR

WINSTON, OR 97496
3
Beds
1
Baths
1,034 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.
0.23 ac
Lot SizeThe size of the land the home sits on, from county records.
1949
Year BuiltThe year the home was originally built, according to county records.

Valuation

$231K
$204K low$259K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$160,000 · Aug 25, 2021

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$2,609 (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.$118,027 (2025)
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$114,590
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$182,339

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.1952
Lot (acres)The size of the land the home sits on, from county records.0.23
RoofThe main material covering the roof, such as asphalt shingle or tile.Composition Shingle
HeatingThe type of heating system in the home.Baseboard
FireplaceWhether the home has a fireplace, and what kind.Yes
PoolWhether the property has a pool, and what kind, such as in-ground.No
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Porch · 105 ft²

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 SchoolC-
Middle · Grades 6–8 · 0.3 mi
H
Douglas High SchoolC
High · Grades 9–12 · 1.3 mi
E
Brockway Elementary School
Elementary · Grades PK–2 · 1.7 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%

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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

421 Se 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 83% of homes in Douglas County
  • Smaller than 81% of homes in Winston 97496
  • Older than 91% 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
$129K$603K

This home is worth more than 20% 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$231,277
CheaperTypical $310,808Pricier

Pricier than 20% of homes nearby

Price per ft²$224
CheaperTypical $234Pricier

Pricier than 41% of homes nearby

Living area1,034 ft²
SmallerTypical 1,404 ft²Bigger

Bigger than 19% of homes nearby

Lot size0.23 ac
SmallerTypical 0.24 acBigger

Bigger than 49% of homes nearby

Year built1949
OlderTypical 1980Newer

Newer than 9% of homes nearby

How 421 Se Gregory Dr ranks against every home in each area.
MeasureThis homeWinston 97496Douglas County
Estimated valuepricier than$231,27720% of homes17% of homes
Price per ft²pricier than$22441% of homes39% of homes
Living areabigger than1,034 ft²19% of homes19% of homes
Lot sizebigger than0.23 ac49% of homes39% of homes
Year builtnewer than19499% of homes18% of homes

About 421 Se Gregory Dr

How much is 421 Se Gregory Dr, Winston, OR worth?

The TopHap Estimate for 421 Se Gregory Dr, Winston, OR is $231,277 as of Aug 30, 2026. The likely range is $203,875 to $258,679. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 421 Se Gregory Dr, Winston, OR last sell?

421 Se Gregory Dr, Winston, OR last sold on Aug 25, 2021 for $160,000, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.

How big is 421 Se Gregory Dr, Winston, OR?

421 Se Gregory Dr, Winston, OR has 3 bedrooms, 1 bathrooms, 1,034 square feet of living space and a 0.23-acre lot.

When was 421 Se Gregory Dr, Winston, OR built?

421 Se Gregory Dr, Winston, OR was built in 1949, making it 77 years old.

What schools serve 421 Se Gregory Dr, Winston, OR?

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

How does 421 Se Gregory Dr, Winston, OR compare to other homes in Winston 97496?

Among the 2,487 homes in Winston 97496, it is worth more than 20% of them ($231,277 against a typical $310,808), its price per square foot is higher than 41% of them ($224 against a typical $234), it is bigger than 19% of them (1,034 ft² against a typical 1,404 ft²), its lot is bigger than 49% of them (0.23 ac against a typical 0.24 ac) and it is newer than 9% of them (1949 against a typical 1980). Measured against all of Douglas County, it is worth more than 17% 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 421 Se Gregory Dr, Winston, OR?

The 2025 property tax bill for 421 Se Gregory Dr, Winston, OR was $2,609. The county assessed it at $118,027.

More homes on Se Gregory Dr

Closest homes

More homes in Winston 97496

Assigned schools

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