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Single Family ResidenceResidential
$421,243$288 / 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 Aug 30, 2026
Last sold for $250,000 on Jun 27, 2005

21 MIDDLESEX AVE

CHESTER, CT 06412
3
Beds
3.5
Baths
1,464 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.
1.25 ac
Lot SizeThe size of the land the home sits on, from county records.
1968
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.
2
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$421K
$405K low$438K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$250,000 · Jun 27, 2005

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$6,216 (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.$229,530 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$59,430
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$170,100
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$229,530
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$160,671

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
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.1994
Lot (acres)The size of the land the home sits on, from county records.1.25
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.Shingle
HeatingThe type of heating system in the home.Gravity
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

Transaction History(3)

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 · 0.9 mi
H
Valley Regional High SchoolB
High · Grades 9–12 · 1.9 mi
M
John Winthrop Middle SchoolC
Middle · Grades 7–8 · 2.4 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

21 Middlesex Ave 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 76% of homes in Chester 06412
  • Costs less per square foot than 68% of homes in Chester 06412
  • Smaller than 66% of homes in Chester 06412
  • Has a bigger lot than 69% 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
$225K$1.2M

This home is worth more than 24% 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$421,243
CheaperTypical $535,693Pricier

Pricier than 24% of homes nearby

Price per ft²$288
CheaperTypical $310Pricier

Pricier than 32% of homes nearby

Living area1,464 ft²
SmallerTypical 1,772 ft²Bigger

Bigger than 34% of homes nearby

Lot size1.25 ac
SmallerTypical 1.32 acBigger

Bigger than 48% of homes nearby

Year built1968
OlderTypical 1966Newer

Newer than 52% of homes nearby

How 21 Middlesex Ave ranks against every home in each area.
MeasureThis homeChester 06412Lower Connecticut River Valley County
Estimated valuepricier than$421,24324% of homes36% of homes
Price per ft²pricier than$28832% of homes50% of homes
Living areabigger than1,464 ft²34% of homes41% of homes
Lot sizebigger than1.25 ac48% of homes69% of homes
Year builtnewer than196852% of homes46% of homes

About 21 Middlesex Ave

How much is 21 Middlesex Ave, Chester, CT worth?

The TopHap Estimate for 21 Middlesex Ave, Chester, CT is $421,243 as of Aug 30, 2026. The likely range is $404,551 to $437,935. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 21 Middlesex Ave, Chester, CT last sell?

21 Middlesex Ave, Chester, CT last sold on Jun 27, 2005 for $250,000, according to the county's recorded deed.

How big is 21 Middlesex Ave, Chester, CT?

21 Middlesex Ave, Chester, CT has 3 bedrooms, 3.5 bathrooms, 1,464 square feet of living space and a 1.25-acre lot.

When was 21 Middlesex Ave, Chester, CT built?

21 Middlesex Ave, Chester, CT was built in 1968, making it 58 years old. It is a ranch home. The building has 1 story.

What schools serve 21 Middlesex Ave, Chester, CT?

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

How does 21 Middlesex Ave, Chester, CT compare to other homes in Chester 06412?

Among the 1,415 homes in Chester 06412, it is worth more than 24% of them ($421,243 against a typical $535,693), its price per square foot is higher than 32% of them ($288 against a typical $310), it is bigger than 34% of them (1,464 ft² against a typical 1,772 ft²), its lot is bigger than 48% of them (1.25 ac against a typical 1.32 ac) and it is newer than 52% of them (1968 against a typical 1966). Measured against all of Lower Connecticut River Valley County, it is worth more than 36% 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 21 Middlesex Ave, Chester, CT?

The 2025 property tax bill for 21 Middlesex Ave, Chester, CT was $6,216. The county assessed it at $229,530.

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