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Single Family ResidenceResidential
$433,370$197 / 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 Jul 14, 2026
Last sold for $272,000 on Dec 23, 2019

99 ROSLYN DR

CHESHIRE, CT 06410
4
Beds
2.5
Baths
2,196 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.
0.93 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.
1
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.
1
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$433K
$416K low$450K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$272,000 · Dec 23, 2019

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$6,912 (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.$232,400 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$81,970
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$150,430
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$232,400
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$162,680

Climate Risk

Projected Flood DepthHow deep a serious flood is expected to get here at some point in the next 30 years. Shown in inches.71 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.51%
FEMA Flood ZoneFEMA's flood zone for this address. Zones starting with A or V are high risk, and lenders usually require flood insurance there.minimal

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
StyleThe architectural style of the home, such as ranch or colonial.Ranch
CountyNAUGATUCK VALLEY
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.1975
Lot (acres)The size of the land the home sits on, from county records.0.93
ConstructionThe main material the home's frame and walls are built from.Frame (Unspecified)
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Hot Water
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, Basement
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.Deck

Transaction History(6)

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.

E
Norton Elementary SchoolA+
Elementary · Grades KG–6 · 0.5 mi
H
Cheshire High SchoolA
High · Grades 9–12 · 1.4 mi
M
Dodd Middle SchoolA-
Middle · Grades 7–8 · 2.8 mi

District: Cheshire School District

Neighborhood · ZIP 06410These 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.93
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.112
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.70

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.97%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.32%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.3.9%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.0%
PopulationHow many people live in this area.29,885
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.891 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$141,047
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$170,143
Average tempThe average temperature here across a full year.50°F
Annual precipHow much rain and melted snow falls here in a typical year.51 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.58%

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

99 Roslyn 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 82% of homes in Cheshire 06410
  • Costs less per square foot than 98% of homes in Cheshire 06410
  • Bigger than 78% of homes in Naugatuck Valley County
  • Has a bigger lot than 75% of homes in Naugatuck Valley County
  • Older than 77% of homes in Cheshire 06410

What homes are worth in Cheshire 06410

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

This home
$227K$1.1M

This home is worth more than 18% of homes in Cheshire 06410.

How it measures up in Cheshire 06410

The dot is this home. The mark in the middle is the typical home in Cheshire 06410.

Estimated value$433,370
CheaperTypical $570,871Pricier

Pricier than 18% of homes nearby

Price per ft²$197
CheaperTypical $301Pricier

Pricier than 2% of homes nearby

Living area2,196 ft²
SmallerTypical 1,893 ft²Bigger

Bigger than 63% of homes nearby

Lot size0.93 ac
SmallerTypical 0.64 acBigger

Bigger than 66% of homes nearby

Year built1955
OlderTypical 1972Newer

Newer than 23% of homes nearby

How 99 Roslyn Dr ranks against every home in each area.
MeasureThis homeCheshire 06410Naugatuck Valley County
Estimated valuepricier than$433,37018% of homes58% of homes
Price per ft²pricier than$1972% of homes11% of homes
Living areabigger than2,196 ft²63% of homes78% of homes
Lot sizebigger than0.93 ac66% of homes75% of homes
Year builtnewer than195523% of homes33% of homes

About 99 Roslyn Dr

How much is 99 Roslyn Dr, Cheshire, CT worth?

The TopHap Estimate for 99 Roslyn Dr, Cheshire, CT is $433,370 as of Jul 14, 2026. The likely range is $416,420 to $450,320. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 99 Roslyn Dr, Cheshire, CT last sell?

99 Roslyn Dr, Cheshire, CT last sold on Dec 23, 2019 for $272,000, according to the county's recorded deed.

How big is 99 Roslyn Dr, Cheshire, CT?

99 Roslyn Dr, Cheshire, CT has 4 bedrooms, 2.5 bathrooms, 2,196 square feet of living space and a 0.93-acre lot.

When was 99 Roslyn Dr, Cheshire, CT built?

99 Roslyn Dr, Cheshire, CT was built in 1955, making it 71 years old. It is a ranch home. The building has 1 story.

What schools serve 99 Roslyn Dr, Cheshire, CT?

99 Roslyn Dr, Cheshire, CT is assigned to Norton Elementary School (elementary), rated A+; Cheshire High School (high), rated A; Dodd Middle School (middle), rated A-. All sit in Cheshire School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 99 Roslyn Dr, Cheshire, CT compare to other homes in Cheshire 06410?

Among the 9,666 homes in Cheshire 06410, it is worth more than 18% of them ($433,370 against a typical $570,871), its price per square foot is higher than 2% of them ($197 against a typical $301), it is bigger than 63% of them (2,196 ft² against a typical 1,893 ft²), its lot is bigger than 66% of them (0.93 ac against a typical 0.64 ac) and it is newer than 23% of them (1955 against a typical 1972). Measured against all of Naugatuck Valley County, it is worth more than 58% 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 99 Roslyn Dr, Cheshire, CT?

The 2025 property tax bill for 99 Roslyn Dr, Cheshire, CT was $6,912. The county assessed it at $232,400.

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