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Single Family ResidenceResidential
$276,658$244 / 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 95How 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 $69,000 on Apr 30, 1986

66 HIGHLAND ST

WINCHENDON, MA 01475
2
Beds
1
Baths
1,134 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.
0.21 ac
Lot SizeThe size of the land the home sits on, from county records.
1900
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

$277K
$262K low$291K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$69,000 · Apr 30, 1986

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$2,532 (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.$215,500 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$36,600
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$178,900
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$193,200
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$245,005

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
CountyWORCESTER
Lot (acres)The size of the land the home sits on, from county records.0.21
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
PoolWhether the property has a pool, and what kind, such as in-ground.No

Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.

E
Memorial
Elementary · Grades KG–2 · 0.6 mi
M
Murdock Middle SchoolD+
Middle · Grades 6–8 · 0.7 mi
H
Murdock High SchoolD+
High · Grades 9–12 · 0.7 mi

District: Winchendon School District

Neighborhood · ZIP 01475These 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.109
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.91
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.65

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.93%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.16%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.11%
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.10,310
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.240 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$90,119
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$110,713
Average tempThe average temperature here across a full year.45°F
Annual precipHow much rain and melted snow falls here in a typical year.47 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.50%

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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 Highland 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 95% of homes in Worcester County
  • Costs less per square foot than 82% of homes in Worcester County
  • Smaller than 84% of homes in Worcester County
  • Has a smaller lot than 91% of homes in Winchendon 01475
  • Older than 87% of homes in Worcester County

What homes are worth in Winchendon 01475

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

This home
$185K$680K

This home is worth more than 12% of homes in Winchendon 01475.

How it measures up in Winchendon 01475

The dot is this home. The mark in the middle is the typical home in Winchendon 01475.

Estimated value$276,658
CheaperTypical $386,699Pricier

Pricier than 12% of homes nearby

Price per ft²$244
CheaperTypical $246Pricier

Pricier than 48% of homes nearby

Living area1,134 ft²
SmallerTypical 1,589 ft²Bigger

Bigger than 20% of homes nearby

Lot size0.21 ac
SmallerTypical 0.98 acBigger

Bigger than 9% of homes nearby

Year built1900
OlderTypical 1978Newer

Newer than 23% of homes nearby

How 66 Highland St ranks against every home in each area.
MeasureThis homeWinchendon 01475Worcester County
Estimated valuepricier than$276,65812% of homes5% of homes
Price per ft²pricier than$24448% of homes18% of homes
Living areabigger than1,134 ft²20% of homes16% of homes
Lot sizebigger than0.21 ac9% of homes20% of homes
Year builtnewer than190023% of homes13% of homes

About 66 Highland St

How much is 66 Highland St, Winchendon, MA worth?

The TopHap Estimate for 66 Highland St, Winchendon, MA is $276,658 as of Sep 24, 2026. The likely range is $262,262 to $291,054. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 66 Highland St, Winchendon, MA last sell?

66 Highland St, Winchendon, MA last sold on Apr 30, 1986 for $69,000, according to the county's recorded deed.

How big is 66 Highland St, Winchendon, MA?

66 Highland St, Winchendon, MA has 2 bedrooms, 1 bathrooms, 1,134 square feet of living space and a 0.21-acre lot.

When was 66 Highland St, Winchendon, MA built?

66 Highland St, Winchendon, MA was built in 1900, making it 126 years old. The building has 2 stories.

What schools serve 66 Highland St, Winchendon, MA?

66 Highland St, Winchendon, MA is assigned to Memorial (elementary); Murdock Middle School (middle), rated D+; Murdock High School (high), rated D+. All sit in Winchendon School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 66 Highland St, Winchendon, MA compare to other homes in Winchendon 01475?

Among the 3,357 homes in Winchendon 01475, it is worth more than 12% of them ($276,658 against a typical $386,699), its price per square foot is higher than 48% of them ($244 against a typical $246), it is bigger than 20% of them (1,134 ft² against a typical 1,589 ft²), its lot is bigger than 9% of them (0.21 ac against a typical 0.98 ac) and it is newer than 23% of them (1900 against a typical 1978). Measured against all of Worcester County, it is worth more than 5% 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 St, Winchendon, MA?

The 2025 property tax bill for 66 Highland St, Winchendon, MA was $2,532. The county assessed it at $215,500.

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