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Single Family ResidenceResidential
$910,825$854 / 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 87How 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 $400,000 on Dec 29, 2016

66 MIDDLESEX ST

WINCHESTER, MA 01890
2
Beds
1
Baths
1,067 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.
0.11 ac
Lot SizeThe size of the land the home sits on, from county records.
1930
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
6
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$911K
$795K low$1M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$400,000 · Dec 29, 2016

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$8,549 (2026)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$771,600 (2026)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$587,300
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$184,300
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$738,200
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$733,204

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.2 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.6%
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
CountyMIDDLESEX
Lot (acres)The size of the land the home sits on, from county records.0.11
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.Steam
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(5)

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
Lynch Elementary SchoolA
Elementary · Grades KG–5 · 0.3 mi
H
Winchester High SchoolA+
High · Grades 9–12 · 0.5 mi
M
McCall Middle SchoolA+
Middle · Grades 6–8 · 0.8 mi

District: Winchester School District

Neighborhood · ZIP 01890These 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.23
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.109
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.82

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.96%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.29%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.3.4%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.2%
PopulationHow many people live in this area.23,604
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.3,661 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$195,899
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$255,940
Average tempThe average temperature here across a full year.49°F
Annual precipHow much rain and melted snow falls here in a typical year.48 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

66 Middlesex 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.

  • Worth less than 85% of homes in Winchester 01890
  • Costs more per square foot than 98% of homes in Winchester 01890
  • Smaller than 94% of homes in Winchester 01890
  • Has a smaller lot than 97% of homes in Winchester 01890
  • Older than 67% of homes in Winchester 01890

What homes are worth in Winchester 01890

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

This home
$351K$3.6M

This home is worth more than 15% of homes in Winchester 01890.

How it measures up in Winchester 01890

The dot is this home. The mark in the middle is the typical home in Winchester 01890.

Estimated value$910,825
CheaperTypical $1,514,206Pricier

Pricier than 15% of homes nearby

Price per ft²$854
CheaperTypical $582Pricier

Pricier than 98% of homes nearby

Living area1,067 ft²
SmallerTypical 2,634 ft²Bigger

Bigger than 6% of homes nearby

Lot size0.11 ac
SmallerTypical 0.27 acBigger

Bigger than 3% of homes nearby

Year built1930
OlderTypical 1952Newer

Newer than 33% of homes nearby

How 66 Middlesex St ranks against every home in each area.
MeasureThis homeWinchester 01890Middlesex County
Estimated valuepricier than$910,82515% of homes64% of homes
Price per ft²pricier than$85498% of homes94% of homes
Living areabigger than1,067 ft²6% of homes13% of homes
Lot sizebigger than0.11 ac3% of homes14% of homes
Year builtnewer than193033% of homes33% of homes

About 66 Middlesex St

How much is 66 Middlesex St, Winchester, MA worth?

The TopHap Estimate for 66 Middlesex St, Winchester, MA is $910,825 as of Sep 24, 2026. The likely range is $795,381 to $1,026,269. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 66 Middlesex St, Winchester, MA last sell?

66 Middlesex St, Winchester, MA last sold on Dec 29, 2016 for $400,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 66 Middlesex St, Winchester, MA?

66 Middlesex St, Winchester, MA has 2 bedrooms, 1 bathrooms, 1,067 square feet of living space and a 0.11-acre lot.

When was 66 Middlesex St, Winchester, MA built?

66 Middlesex St, Winchester, MA was built in 1930, making it 96 years old. The building has 2 stories.

What schools serve 66 Middlesex St, Winchester, MA?

66 Middlesex St, Winchester, MA is assigned to Lynch Elementary School (elementary), rated A; Winchester High School (high), rated A+; McCall Middle School (middle), rated A+. All sit in Winchester School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 66 Middlesex St, Winchester, MA compare to other homes in Winchester 01890?

Among the 7,523 homes in Winchester 01890, it is worth more than 15% of them ($910,825 against a typical $1,514,206), its price per square foot is higher than 98% of them ($854 against a typical $582), it is bigger than 6% of them (1,067 ft² against a typical 2,634 ft²), its lot is bigger than 3% of them (0.11 ac against a typical 0.27 ac) and it is newer than 33% of them (1930 against a typical 1952). Measured against all of Middlesex County, it is worth more than 64% 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 Middlesex St, Winchester, MA?

The 2026 property tax bill for 66 Middlesex St, Winchester, MA was $8,549. The county assessed it at $771,600.

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Assigned schools

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