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Single Family ResidenceResidential
$1,462,337$628 / 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 Sep 24, 2026

99 WOODCHESTER DR

CHESTNUT HILL, MA 02467
3
Beds
2.5
Baths
2,330 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.
0.14 ac
Lot SizeThe size of the land the home sits on, from county records.
1935
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
7
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$1.5M
$1.4M low$1.5M high

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$14,537 (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.$1,483,400 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$1,480,300
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$3,100
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$1,913,205

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.Tudor
CountyMIDDLESEX
Lot (acres)The size of the land the home sits on, from county records.0.14
ConstructionThe main material the home's frame and walls are built from.Concrete
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Forced Air With Air Conditioning
CoolingThe type of cooling or air conditioning in the home.Yes
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, Detached
PoolWhether the property has a pool, and what kind, such as in-ground.No
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Deck

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
Ward Elementary SchoolA+
Elementary · Grades KG–5 · 0.1 mi
M
Bigelow Middle SchoolA
Middle · Grades 6–8 · 0.9 mi
H
Newton North High SchoolA+
High · Grades 9–12 · 1.6 mi

District: Newton School District

Neighborhood · ZIP 02467These 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.71
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.101
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.74

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.31%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.5.8%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.0%
PopulationHow many people live in this area.22,148
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.4,410 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$174,702
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$252,311
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.54%

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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

99 Woodchester 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 87% of homes in Middlesex County
  • Costs more per square foot than 80% of homes in Middlesex County
  • Bigger than 69% of homes in Middlesex County
  • Has a smaller lot than 82% of homes in Newton Corner
  • Older than 74% of homes in Chestnut Hill 02467

What homes are worth in Chestnut Hill 02467

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

This home
$334K$6.8M

This home is worth more than 48% of homes in Chestnut Hill 02467.

How it measures up in Chestnut Hill 02467

The dot is this home. The mark in the middle is the typical home in Chestnut Hill 02467.

Estimated value$1,462,337
CheaperTypical $1,514,757Pricier

Pricier than 48% of homes nearby

Price per ft²$628
CheaperTypical $749Pricier

Pricier than 25% of homes nearby

Living area2,330 ft²
SmallerTypical 1,953 ft²Bigger

Bigger than 62% of homes nearby

Lot size0.14 ac
SmallerTypical 0.27 acBigger

Bigger than 23% of homes nearby

Year built1935
OlderTypical 1955Newer

Newer than 26% of homes nearby

How 99 Woodchester Dr ranks against every home in each area.
MeasureThis homeNewton CornerChestnut Hill 02467Middlesex County
Estimated valuepricier than$1,462,33748% of homes48% of homes87% of homes
Price per ft²pricier than$62839% of homes25% of homes80% of homes
Living areabigger than2,330 ft²45% of homes62% of homes69% of homes
Lot sizebigger than0.14 ac18% of homes23% of homes23% of homes
Year builtnewer than193568% of homes26% of homes34% of homes

About 99 Woodchester Dr

How much is 99 Woodchester Dr, Chestnut Hill, MA worth?

The TopHap Estimate for 99 Woodchester Dr, Chestnut Hill, MA is $1,462,337 as of Sep 24, 2026. The likely range is $1,398,186 to $1,526,488. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 99 Woodchester Dr, Chestnut Hill, MA last sell?

99 Woodchester Dr, Chestnut Hill, MA last sold on Jan 1, 1900, according to the county's recorded deed.

How big is 99 Woodchester Dr, Chestnut Hill, MA?

99 Woodchester Dr, Chestnut Hill, MA has 3 bedrooms, 2.5 bathrooms, 2,330 square feet of living space and a 0.14-acre lot.

When was 99 Woodchester Dr, Chestnut Hill, MA built?

99 Woodchester Dr, Chestnut Hill, MA was built in 1935, making it 91 years old. It is a tudor home. The building has 2 stories.

What schools serve 99 Woodchester Dr, Chestnut Hill, MA?

99 Woodchester Dr, Chestnut Hill, MA is assigned to Ward Elementary School (elementary), rated A+; Bigelow Middle School (middle), rated A; Newton North High School (high), rated A+. All sit in Newton School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 99 Woodchester Dr, Chestnut Hill, MA compare to other homes in Chestnut Hill 02467?

Among the 5,309 homes in Chestnut Hill 02467, it is worth more than 48% of them ($1,462,337 against a typical $1,514,757), its price per square foot is higher than 25% of them ($628 against a typical $749), it is bigger than 62% of them (2,330 ft² against a typical 1,953 ft²), its lot is bigger than 23% of them (0.14 ac against a typical 0.27 ac) and it is newer than 26% of them (1935 against a typical 1955). Measured against all of Middlesex County, it is worth more than 87% 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 99 Woodchester Dr, Chestnut Hill, MA?

The 2025 property tax bill for 99 Woodchester Dr, Chestnut Hill, MA was $14,537. The county assessed it at $1,483,400.

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