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Single Family ResidenceResidential
$296,641$189 / 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 $119,900 on Aug 29, 2002

5 GREGORY ST

WINSTED, CT 06098
4
Beds
1.5
Baths
1,569 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.
0.24 ac
Lot SizeThe size of the land the home sits on, from county records.
1852
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
8
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$297K
$272K low$321K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$119,900 · Aug 29, 2002

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$3,974 (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.$136,220 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$32,200
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$104,020
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$136,220
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$95,354

Climate Risk

Overall riskThe average of the five hazard scores below, on a 0 to 100 scale. Higher means greater projected risk over the coming decades.43
10
FloodProjected flooding risk from rivers, heavy rain, and storm surge, scored 0 to 100. Higher is riskier.
14
WildfireProjected wildfire risk, scored 0 to 100, based on how much land burns in a typical year. Higher is riskier.
59
HeatProjected heat risk, scored 0 to 100, based on how many extremely hot days a year are expected. Higher is riskier.
98
StormProjected risk from heavy rainstorms, scored 0 to 100, based on how often extreme rainfall is expected. Higher is riskier.
37
DroughtProjected water shortage risk, scored 0 to 100. Higher means more strain on the local water supply.
Projected Flood DepthHow deep a serious flood is expected to get here at some point in the next 30 years. Shown in inches.7 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.6%

Scores 0–100; higher = greater projected risk.

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
CountyNORTHWEST HILLS
Lot (acres)The size of the land the home sits on, from county records.0.24
ConstructionThe main material the home's frame and walls are built from.Concrete
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Hot Water
PoolWhether the property has a pool, and what kind, such as in-ground.No

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.

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

M
The Gilbert SchoolC-
Middle · Grades 7–12 · 0.7 mi
E
Mary P. Hinsdale SchoolD
Elementary · Grades PK–2 · 0.8 mi

District: The Gilbert School District

Neighborhood · ZIP 06098These 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.102
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.92
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.65

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.88%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.17%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.13%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.7%
PopulationHow many people live in this area.10,512
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.188 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$82,081
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$95,758
Average tempThe average temperature here across a full year.45°F
Annual precipHow much rain and melted snow falls here in a typical year.53 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.56%

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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

5 Gregory St 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 79% of homes in Northwest Hills County
  • Costs less per square foot than 85% of homes in Northwest Hills County
  • Has a smaller lot than 87% of homes in Northwest Hills County
  • Older than 96% of homes in Winsted 06098

What homes are worth in Winsted 06098

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

This home
$158K$931K

This home is worth more than 42% of homes in Winsted 06098.

How it measures up in Winsted 06098

The dot is this home. The mark in the middle is the typical home in Winsted 06098.

Estimated value$296,641
CheaperTypical $314,775Pricier

Pricier than 42% of homes nearby

Price per ft²$189
CheaperTypical $217Pricier

Pricier than 33% of homes nearby

Living area1,569 ft²
SmallerTypical 1,527 ft²Bigger

Bigger than 53% of homes nearby

Lot size0.24 ac
SmallerTypical 0.42 acBigger

Bigger than 26% of homes nearby

Year built1852
OlderTypical 1953Newer

Newer than 4% of homes nearby

How 5 Gregory St ranks against every home in each area.
MeasureThis homeWinsted 06098Northwest Hills County
Estimated valuepricier than$296,64142% of homes21% of homes
Price per ft²pricier than$18933% of homes15% of homes
Living areabigger than1,569 ft²53% of homes42% of homes
Lot sizebigger than0.24 ac26% of homes13% of homes
Year builtnewer than18524% of homes5% of homes

About 5 Gregory St

How much is 5 Gregory St, Winsted, CT worth?

The TopHap Estimate for 5 Gregory St, Winsted, CT is $296,641 as of Sep 24, 2026. The likely range is $272,263 to $321,019. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 5 Gregory St, Winsted, CT last sell?

5 Gregory St, Winsted, CT last sold on Aug 29, 2002 for $119,900, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 5 Gregory St, Winsted, CT?

5 Gregory St, Winsted, CT has 4 bedrooms, 1.5 bathrooms, 1,569 square feet of living space and a 0.24-acre lot.

When was 5 Gregory St, Winsted, CT built?

5 Gregory St, Winsted, CT was built in 1852, making it 174 years old. The building has 2 stories.

What schools serve 5 Gregory St, Winsted, CT?

5 Gregory St, Winsted, CT is assigned to The Gilbert School (middle), rated C-; Mary P. Hinsdale School (elementary), rated D. All sit in The Gilbert School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 5 Gregory St, Winsted, CT compare to other homes in Winsted 06098?

Among the 3,791 homes in Winsted 06098, it is worth more than 42% of them ($296,641 against a typical $314,775), its price per square foot is higher than 33% of them ($189 against a typical $217), it is bigger than 53% of them (1,569 ft² against a typical 1,527 ft²), its lot is bigger than 26% of them (0.24 ac against a typical 0.42 ac) and it is newer than 4% of them (1852 against a typical 1953). Measured against all of Northwest Hills County, it is worth more than 21% 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 5 Gregory St, Winsted, CT?

The 2025 property tax bill for 5 Gregory St, Winsted, CT was $3,974. The county assessed it at $136,220.

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