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Single Family ResidenceResidential
$1,505,235$629 / 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 91How 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 $725,000 on Oct 27, 2016

23 WINDSOR DR

EDGARTOWN, MA 02539
3
Beds
3
Baths
2,392 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.
0.51 ac
Lot SizeThe size of the land the home sits on, from county records.
1981
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

$1.5M
$1.4M low$1.6M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$725,000 · Oct 27, 2016

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$3,358 (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.$1,267,100 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$334,100
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$933,000
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$1,053,300

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.Contemporary
CountyDUKES
Lot (acres)The size of the land the home sits on, from county records.0.51
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
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(7)

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.

H
Martha's Vineyard Regional High SchoolB-
High · Grades 9–12 · 1.4 mi
E
Edgartown Elementary SchoolA-
Elementary · Grades PK–8 · 2.9 mi

District: Edgartown School District

Neighborhood · ZIP 02539These 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.96
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.97
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.40

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.49%
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.4.4%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.4%
PopulationHow many people live in this area.6,633
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.123 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$89,764
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$138,074
Average tempThe average temperature here across a full year.50°F
Annual precipHow much rain and melted snow falls here in a typical year.46 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

23 Windsor 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 less than 67% of homes in Edgartown 02539
  • Costs less per square foot than 96% of homes in Edgartown 02539
  • Bigger than 73% of homes in Dukes County

What homes are worth in Edgartown 02539

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

This home
$735K$10M

This home is worth more than 33% of homes in Edgartown 02539.

How it measures up in Edgartown 02539

The dot is this home. The mark in the middle is the typical home in Edgartown 02539.

Estimated value$1,505,235
CheaperTypical $1,871,179Pricier

Pricier than 33% of homes nearby

Price per ft²$629
CheaperTypical $1058Pricier

Pricier than 4% of homes nearby

Living area2,392 ft²
SmallerTypical 1,857 ft²Bigger

Bigger than 69% of homes nearby

Lot size0.51 ac
SmallerTypical 0.53 acBigger

Bigger than 40% of homes nearby

Year built1981
OlderTypical 1986Newer

Newer than 36% of homes nearby

How 23 Windsor Dr ranks against every home in each area.
MeasureThis homeEdgartown 02539Dukes County
Estimated valuepricier than$1,505,23533% of homes43% of homes
Price per ft²pricier than$6294% of homes6% of homes
Living areabigger than2,392 ft²69% of homes73% of homes
Lot sizebigger than0.51 ac40% of homes43% of homes
Year builtnewer than198136% of homes46% of homes

About 23 Windsor Dr

How much is 23 Windsor Dr, Edgartown, MA worth?

The TopHap Estimate for 23 Windsor Dr, Edgartown, MA is $1,505,235 as of Aug 30, 2026. The likely range is $1,367,269 to $1,643,201. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 23 Windsor Dr, Edgartown, MA last sell?

23 Windsor Dr, Edgartown, MA last sold on Oct 27, 2016 for $725,000, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.

How big is 23 Windsor Dr, Edgartown, MA?

23 Windsor Dr, Edgartown, MA has 3 bedrooms, 3 bathrooms, 2,392 square feet of living space and a 0.51-acre lot.

When was 23 Windsor Dr, Edgartown, MA built?

23 Windsor Dr, Edgartown, MA was built in 1981, making it 45 years old. It is a contemporary home. The building has 2 stories.

What schools serve 23 Windsor Dr, Edgartown, MA?

23 Windsor Dr, Edgartown, MA is assigned to Martha's Vineyard Regional High School (high), rated B-; Edgartown Elementary School (elementary), rated A-. All sit in Edgartown School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 23 Windsor Dr, Edgartown, MA compare to other homes in Edgartown 02539?

Among the 4,634 homes in Edgartown 02539, it is worth more than 33% of them ($1,505,235 against a typical $1,871,179), its price per square foot is higher than 4% of them ($629 against a typical $1058), it is bigger than 69% of them (2,392 ft² against a typical 1,857 ft²), its lot is bigger than 40% of them (0.51 ac against a typical 0.53 ac) and it is newer than 36% of them (1981 against a typical 1986). Measured against all of Dukes County, it is worth more than 43% 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 23 Windsor Dr, Edgartown, MA?

The 2025 property tax bill for 23 Windsor Dr, Edgartown, MA was $3,358. The county assessed it at $1,267,100.

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