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Single Family ResidenceResidential
$341,999$187 / 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 90How 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 $290,000 on May 28, 2024

66 HIGHLAND DR

WATERBURY, CT 06708
2
Beds
1.5
Baths
1,828 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.
0.36 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.
2
StoriesHow many floors the home has above ground.
5
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$342K
$307K low$377K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$290,000 · May 28, 2024

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$7,125 (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.$158,410 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$23,450
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$134,960
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$158,410
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$110,887

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.Cape Cod
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.1977
Lot (acres)The size of the land the home sits on, from county records.0.36
ConstructionThe main material the home's frame and walls are built from.Frame (Unspecified)
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.Carport (Unspecified)
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(4)

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.

H
Kennedy High SchoolD-
High · Grades 9–12 · 0.3 mi
E
B. W. Tinker Elementary SchoolC
Elementary · Grades KG–5 · 0.4 mi
M
West Side Middle SchoolC-
Middle · Grades 6–8 · 0.5 mi

District: Waterbury School District

Neighborhood · ZIP 06708These 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.81
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.104
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.69

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.13%
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.1.1%
PopulationHow many people live in this area.32,336
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.3,332 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$67,073
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$82,401
Average tempThe average temperature here across a full year.49°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%

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

66 Highland 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 73% of homes in Town Plot
  • Costs less per square foot than 92% of homes in Naugatuck Valley County
  • Bigger than 83% of homes in Town Plot
  • Has a bigger lot than 93% of homes in Town Plot
  • Older than 76% of homes in Naugatuck Valley County

What homes are worth in Waterbury 06708

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

This home
$127K$523K

This home is worth more than 59% of homes in Waterbury 06708.

How it measures up in Waterbury 06708

The dot is this home. The mark in the middle is the typical home in Waterbury 06708.

Estimated value$341,999
CheaperTypical $325,732Pricier

Pricier than 59% of homes nearby

Price per ft²$187
CheaperTypical $244Pricier

Pricier than 18% of homes nearby

Living area1,828 ft²
SmallerTypical 1,330 ft²Bigger

Bigger than 77% of homes nearby

Lot size0.36 ac
SmallerTypical 0.21 acBigger

Bigger than 85% of homes nearby

Year built1949
OlderTypical 1959Newer

Newer than 32% of homes nearby

How 66 Highland Dr ranks against every home in each area.
MeasureThis homeTown PlotWaterbury 06708Naugatuck Valley County
Estimated valuepricier than$341,99973% of homes59% of homes32% of homes
Price per ft²pricier than$18714% of homes18% of homes8% of homes
Living areabigger than1,828 ft²83% of homes77% of homes65% of homes
Lot sizebigger than0.36 ac93% of homes85% of homes47% of homes
Year builtnewer than194925% of homes32% of homes24% of homes

About 66 Highland Dr

How much is 66 Highland Dr, Waterbury, CT worth?

The TopHap Estimate for 66 Highland Dr, Waterbury, CT is $341,999 as of Jul 14, 2026. The likely range is $306,945 to $377,053. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 66 Highland Dr, Waterbury, CT last sell?

66 Highland Dr, Waterbury, CT last sold on May 28, 2024 for $290,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 66 Highland Dr, Waterbury, CT?

66 Highland Dr, Waterbury, CT has 2 bedrooms, 1.5 bathrooms, 1,828 square feet of living space and a 0.36-acre lot.

When was 66 Highland Dr, Waterbury, CT built?

66 Highland Dr, Waterbury, CT was built in 1949, making it 77 years old. It is a cape cod home. The building has 2 stories.

What schools serve 66 Highland Dr, Waterbury, CT?

66 Highland Dr, Waterbury, CT is assigned to Kennedy High School (high), rated D-; B. W. Tinker Elementary School (elementary), rated C; West Side Middle School (middle), rated C-. All sit in Waterbury School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 66 Highland Dr, Waterbury, CT compare to other homes in Waterbury 06708?

Among the 8,807 homes in Waterbury 06708, it is worth more than 59% of them ($341,999 against a typical $325,732), its price per square foot is higher than 18% of them ($187 against a typical $244), it is bigger than 77% of them (1,828 ft² against a typical 1,330 ft²), its lot is bigger than 85% of them (0.36 ac against a typical 0.21 ac) and it is newer than 32% of them (1949 against a typical 1959). Measured against all of Naugatuck Valley County, it is worth more than 32% 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 66 Highland Dr, Waterbury, CT?

The 2025 property tax bill for 66 Highland Dr, Waterbury, CT was $7,125. The county assessed it at $158,410.

More homes on Highland Dr

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Assigned schools

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