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CondominiumResidential
$2,379,693$675 / 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 80How 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

165 WINCHESTER ST

BROOKLINE, MA 02446
Building report
4
Beds
3
Baths
3,528 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.
0.24 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.
10
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$2.4M
$1.9M low$2.9M high

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$24,868 (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.$2,519,600 (2025)
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$2,519,600
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$2,044,020

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Condominium
CountyNORFOLK
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.1968
Lot (acres)The size of the land the home sits on, from county records.0.24
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.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
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
Edward Devotion SchoolA
Elementary · Grades KG–8 · 0.4 mi
H
Brookline High SchoolA-
High · Grades 9–12 · 0.8 mi

District: Brookline School District

Neighborhood · ZIP 02446These 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.144
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.108
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.76

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.14%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.1%
PopulationHow many people live in this area.31,401
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.23,893 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$115,895
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$169,699
Average tempThe average temperature here across a full year.50°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.52%

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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

165 Winchester 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 more than 95% of homes in Norfolk County
  • Costs less per square foot than 97% of homes in Coolidge Corner
  • Bigger than 93% of homes in Norfolk County
  • Has a smaller lot than 67% of homes in Norfolk County
  • Older than 90% of homes in Norfolk County

What homes are worth in Brookline 02446

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

This home
$429K$4.5M

This home is worth more than 86% of homes in Brookline 02446.

How it measures up in Brookline 02446

The dot is this home. The mark in the middle is the typical home in Brookline 02446.

Estimated value$2,379,693
CheaperTypical $1,020,905Pricier

Pricier than 86% of homes nearby

Price per ft²$675
CheaperTypical $868Pricier

Pricier than 3% of homes nearby

Living area3,528 ft²
SmallerTypical 1,244 ft²Bigger

Bigger than 89% of homes nearby

Lot size0.24 ac
SmallerTypical 0.29 acBigger

Bigger than 46% of homes nearby

Year built1900
OlderTypical 1925Newer

Newer than 17% of homes nearby

How 165 Winchester St ranks against every home in each area.
MeasureThis homeCoolidge CornerBrookline 02446Norfolk County
Estimated valuepricier than$2,379,69386% of homes86% of homes95% of homes
Price per ft²pricier than$6753% of homes3% of homes84% of homes
Living areabigger than3,528 ft²89% of homes89% of homes93% of homes
Lot sizebigger than0.24 ac45% of homes46% of homes33% of homes
Year builtnewer than190016% of homes17% of homes10% of homes

About 165 Winchester St

How much is 165 Winchester St, Brookline, MA worth?

The TopHap Estimate for 165 Winchester St, Brookline, MA is $2,379,693 as of Sep 24, 2026. The likely range is $1,892,803 to $2,866,583. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 165 Winchester St, Brookline, MA last sell?

165 Winchester St, Brookline, MA last sold on Jan 1, 1900, according to the county's recorded deed.

How big is 165 Winchester St, Brookline, MA?

165 Winchester St, Brookline, MA has 4 bedrooms, 3 bathrooms, 3,528 square feet of living space and a 0.24-acre lot.

When was 165 Winchester St, Brookline, MA built?

165 Winchester St, Brookline, MA was built in 1900, making it 126 years old. The building has 2 stories.

What schools serve 165 Winchester St, Brookline, MA?

165 Winchester St, Brookline, MA is assigned to Edward Devotion School (elementary), rated A; Brookline High School (high), rated A-. All sit in Brookline School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 165 Winchester St, Brookline, MA compare to other homes in Brookline 02446?

Among the 7,868 homes in Brookline 02446, it is worth more than 86% of them ($2,379,693 against a typical $1,020,905), its price per square foot is higher than 3% of them ($675 against a typical $868), it is bigger than 89% of them (3,528 ft² against a typical 1,244 ft²), its lot is bigger than 46% of them (0.24 ac against a typical 0.29 ac) and it is newer than 17% of them (1900 against a typical 1925). Measured against all of Norfolk County, it is worth more than 95% 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 165 Winchester St, Brookline, MA?

The 2025 property tax bill for 165 Winchester St, Brookline, MA was $24,868. The county assessed it at $2,519,600.

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