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Single Family ResidenceResidential
$886,095$246 / 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 96How 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 $493,000 on Aug 29, 2019

50 WINTERWOOD DR

SOUTHBURY, CT 06488
5
Beds
4 / 2
Baths
3,597 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.
1.4 ac
Lot SizeThe size of the land the home sits on, from county records.
1991
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
9
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$886K
$849K low$924K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$493,000 · Aug 29, 2019

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$13,041 (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.$538,900 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$96,740
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$442,160
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$538,900
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$769,857

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
StyleThe architectural style of the home, such as ranch or colonial.Conventional
CountyNAUGATUCK VALLEY
Lot (acres)The size of the land the home sits on, from county records.1.40
RoofThe main material covering the roof, such as asphalt shingle or tile.Shingle
HeatingThe type of heating system in the home.Hot Water
CoolingThe type of cooling or air conditioning in the home.Yes
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
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(10)

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
Rochambeau Middle SchoolA-
Middle · Grades 6–8 · 2.2 mi
E
Pomperaug Elementary SchoolB+
Elementary · Grades PK–5 · 2.3 mi
H
Pomperaug Regional High SchoolA-
High · Grades 9–12 · 4.2 mi

District: Regional School District 15

Neighborhood · ZIP 06488These 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.100
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.107
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.75

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.94%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.30%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.4.0%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.9%
PopulationHow many people live in this area.20,305
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.511 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$107,384
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$123,508
Average tempThe average temperature here across a full year.50°F
Annual precipHow much rain and melted snow falls here in a typical year.52 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.58%

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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

50 Winterwood 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 more than 98% of homes in Naugatuck Valley County
  • Bigger than 97% of homes in Naugatuck Valley County
  • Has a bigger lot than 85% of homes in Naugatuck Valley County
  • Newer than 82% of homes in Naugatuck Valley County

What homes are worth in Southbury 06488

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

This home
$189K$1M

This home is worth more than 95% of homes in Southbury 06488.

How it measures up in Southbury 06488

The dot is this home. The mark in the middle is the typical home in Southbury 06488.

Estimated value$886,095
CheaperTypical $458,168Pricier

Pricier than 95% of homes nearby

Price per ft²$246
CheaperTypical $251Pricier

Pricier than 46% of homes nearby

Living area3,597 ft²
SmallerTypical 1,624 ft²Bigger

Bigger than 94% of homes nearby

Lot size1.4 ac
SmallerTypical 1.62 acBigger

Bigger than 36% of homes nearby

Year built1991
OlderTypical 1974Newer

Newer than 78% of homes nearby

How 50 Winterwood Dr ranks against every home in each area.
MeasureThis homeSouthbury 06488Naugatuck Valley County
Estimated valuepricier than$886,09595% of homes98% of homes
Price per ft²pricier than$24646% of homes40% of homes
Living areabigger than3,597 ft²94% of homes97% of homes
Lot sizebigger than1.4 ac36% of homes85% of homes
Year builtnewer than199178% of homes82% of homes

About 50 Winterwood Dr

How much is 50 Winterwood Dr, Southbury, CT worth?

The TopHap Estimate for 50 Winterwood Dr, Southbury, CT is $886,095 as of Sep 24, 2026. The likely range is $848,618 to $923,572. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 50 Winterwood Dr, Southbury, CT last sell?

50 Winterwood Dr, Southbury, CT last sold on Aug 29, 2019 for $493,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 50 Winterwood Dr, Southbury, CT?

50 Winterwood Dr, Southbury, CT has 5 bedrooms, 4 bathrooms, 3,597 square feet of living space and a 1.40-acre lot.

When was 50 Winterwood Dr, Southbury, CT built?

50 Winterwood Dr, Southbury, CT was built in 1991, making it 35 years old. It is a conventional home. The building has 2 stories.

What schools serve 50 Winterwood Dr, Southbury, CT?

50 Winterwood Dr, Southbury, CT is assigned to Rochambeau Middle School (middle), rated A-; Pomperaug Elementary School (elementary), rated B+; Pomperaug Regional High School (high), rated A-. All sit in Regional School District 15. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 50 Winterwood Dr, Southbury, CT compare to other homes in Southbury 06488?

Among the 8,285 homes in Southbury 06488, it is worth more than 95% of them ($886,095 against a typical $458,168), its price per square foot is higher than 46% of them ($246 against a typical $251), it is bigger than 94% of them (3,597 ft² against a typical 1,624 ft²), its lot is bigger than 36% of them (1.4 ac against a typical 1.62 ac) and it is newer than 78% of them (1991 against a typical 1974). Measured against all of Naugatuck Valley County, it is worth more than 98% 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 50 Winterwood Dr, Southbury, CT?

The 2025 property tax bill for 50 Winterwood Dr, Southbury, CT was $13,041. The county assessed it at $538,900.

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