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Rural ResidenceResidential
$508,281$240 / 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 65How 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 $88,875 on Jul 30, 1996

66 PLEASANT ST

CHESTER, CT 06412
4
Beds
3.5
Baths
2,118 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 ac
Lot SizeThe size of the land the home sits on, from county records.
1895
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

$508K
$331K low$686K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$88,875 · Jul 30, 1996

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$8,214 (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.$303,310 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$56,700
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$246,610
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$303,310
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$212,317

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.38 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.30%
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.Rural Residence
StyleThe architectural style of the home, such as ranch or colonial.Historical
CountyLOWER CONNECTICUT RIVER 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.1987
Lot (acres)The size of the land the home sits on, from county records.1.00
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
CoolingThe type of cooling or air conditioning in the home.Yes
PoolWhether the property has a pool, and what kind, such as in-ground.Yes

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
Chester Elementary SchoolB
Elementary · Grades PK–6 · 0.4 mi
H
Valley Regional High SchoolB
High · Grades 9–12 · 2.6 mi
M
John Winthrop Middle SchoolB-
Middle · Grades 7–8 · 3.0 mi

District: Regional High School District 04

Neighborhood · ZIP 06412These 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.84
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.114
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.57

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.92%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.20%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.10%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.8%
PopulationHow many people live in this area.3,484
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.211 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$87,420
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$112,617
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.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

66 Pleasant 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.

  • Costs less per square foot than 93% of homes in Chester 06412
  • Bigger than 70% of homes in Lower Connecticut River Valley County
  • Older than 94% of homes in Lower Connecticut River Valley County

What homes are worth in Chester 06412

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

This home
$222K$1.3M

This home is worth more than 43% of homes in Chester 06412.

How it measures up in Chester 06412

The dot is this home. The mark in the middle is the typical home in Chester 06412.

Estimated value$508,281
CheaperTypical $537,976Pricier

Pricier than 43% of homes nearby

Price per ft²$240
CheaperTypical $310Pricier

Pricier than 7% of homes nearby

Living area2,118 ft²
SmallerTypical 1,774 ft²Bigger

Bigger than 67% of homes nearby

Lot size1 ac
SmallerTypical 1.3 acBigger

Bigger than 42% of homes nearby

Year built1895
OlderTypical 1967Newer

Newer than 11% of homes nearby

How 66 Pleasant St ranks against every home in each area.
MeasureThis homeChester 06412Lower Connecticut River Valley County
Estimated valuepricier than$508,28143% of homes54% of homes
Price per ft²pricier than$2407% of homes24% of homes
Living areabigger than2,118 ft²67% of homes70% of homes
Lot sizebigger than1 ac42% of homes62% of homes
Year builtnewer than189511% of homes6% of homes

About 66 Pleasant St

How much is 66 Pleasant St, Chester, CT worth?

The TopHap Estimate for 66 Pleasant St, Chester, CT is $508,281 as of Sep 24, 2026. The likely range is $330,722 to $685,840. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 66 Pleasant St, Chester, CT last sell?

66 Pleasant St, Chester, CT last sold on Jul 30, 1996 for $88,875, according to the county's recorded deed.

How big is 66 Pleasant St, Chester, CT?

66 Pleasant St, Chester, CT has 4 bedrooms, 3.5 bathrooms, 2,118 square feet of living space and a 1.00-acre lot.

When was 66 Pleasant St, Chester, CT built?

66 Pleasant St, Chester, CT was built in 1895, making it 131 years old. It is a historical home. The building has 2 stories.

What schools serve 66 Pleasant St, Chester, CT?

66 Pleasant St, Chester, CT is assigned to Chester Elementary School (elementary), rated B; Valley Regional High School (high), rated B; John Winthrop Middle School (middle), rated B-. All sit in Regional High School District 04. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 66 Pleasant St, Chester, CT compare to other homes in Chester 06412?

Among the 1,415 homes in Chester 06412, it is worth more than 43% of them ($508,281 against a typical $537,976), its price per square foot is higher than 7% of them ($240 against a typical $310), it is bigger than 67% of them (2,118 ft² against a typical 1,774 ft²), its lot is bigger than 42% of them (1 ac against a typical 1.3 ac) and it is newer than 11% of them (1895 against a typical 1967). Measured against all of Lower Connecticut River Valley County, it is worth more than 54% 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 Pleasant St, Chester, CT?

The 2025 property tax bill for 66 Pleasant St, Chester, CT was $8,214. The county assessed it at $303,310.

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