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Single Family ResidenceResidential
$290,147$263 / 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
Last sold for $255,000 on Jun 27, 2022

249 HIGHLAND VIEW DR

SOUTH WINDHAM, CT 06266
3
Beds
1
Baths
1,104 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.
0.34 ac
Lot SizeThe size of the land the home sits on, from county records.
1966
Year BuiltThe year the home was originally built, according to county records.
1
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

$290K
$279K low$302K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$255,000 · Jun 27, 2022

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$4,632 (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.$155,160 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$35,640
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$119,520
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$155,160
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$108,612

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.Ranch
CountySOUTHEASTERN CONNECTICUT
Lot (acres)The size of the land the home sits on, from county records.0.34
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Hot Water
FireplaceWhether the home has a fireplace, and what kind.Yes
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(2)

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
Windham Center SchoolD-
Elementary · Grades KG–5 · 2.2 mi
H
Windham High SchoolF
High · Grades 9–12 · 4.4 mi
M
Windham Middle SchoolD+
Middle · Grades 6–8 · 4.8 mi

District: Windham School District

Neighborhood · ZIP 06266These 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.116
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.63

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.92%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.18%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.5.9%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.8%
PopulationHow many people live in this area.243
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.311 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$71,083
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$94,269
Average tempThe average temperature here across a full year.49°F
Annual precipHow much rain and melted snow falls here in a typical year.51 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.56%

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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

249 Highland View 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 85% of homes in Southeastern Connecticut County
  • Costs more per square foot than 69% of homes in South Windham 06266
  • Smaller than 80% of homes in South Windham 06266
  • Has a smaller lot than 90% of homes in South Windham 06266

What homes are worth in South Windham 06266

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

This home
$218K$522K

This home is worth more than 23% of homes in South Windham 06266.

How it measures up in South Windham 06266

The dot is this home. The mark in the middle is the typical home in South Windham 06266.

Estimated value$290,147
CheaperTypical $327,093Pricier

Pricier than 23% of homes nearby

Price per ft²$263
CheaperTypical $231Pricier

Pricier than 69% of homes nearby

Living area1,104 ft²
SmallerTypical 1,436 ft²Bigger

Bigger than 20% of homes nearby

Lot size0.34 ac
SmallerTypical 0.92 acBigger

Bigger than 10% of homes nearby

Year built1966
OlderTypical 1961Newer

Newer than 63% of homes nearby

How 249 Highland View Dr ranks against every home in each area.
MeasureThis homeSouth Windham 06266Southeastern Connecticut County
Estimated valuepricier than$290,14723% of homes15% of homes
Price per ft²pricier than$26369% of homes42% of homes
Living areabigger than1,104 ft²20% of homes22% of homes
Lot sizebigger than0.34 ac10% of homes34% of homes
Year builtnewer than196663% of homes49% of homes

About 249 Highland View Dr

How much is 249 Highland View Dr, South Windham, CT worth?

The TopHap Estimate for 249 Highland View Dr, South Windham, CT is $290,147 as of Sep 24, 2026. The likely range is $278,789 to $301,505. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 249 Highland View Dr, South Windham, CT last sell?

249 Highland View Dr, South Windham, CT last sold on Jun 27, 2022 for $255,000, according to the county's recorded deed.

How big is 249 Highland View Dr, South Windham, CT?

249 Highland View Dr, South Windham, CT has 3 bedrooms, 1 bathrooms, 1,104 square feet of living space and a 0.34-acre lot.

When was 249 Highland View Dr, South Windham, CT built?

249 Highland View Dr, South Windham, CT was built in 1966, making it 60 years old. It is a ranch home. The building has 1 story.

What schools serve 249 Highland View Dr, South Windham, CT?

249 Highland View Dr, South Windham, CT is assigned to Windham Center School (elementary), rated D-; Windham High School (high), rated F; Windham Middle School (middle), rated D+. All sit in Windham School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 249 Highland View Dr, South Windham, CT compare to other homes in South Windham 06266?

Among the 176 homes in South Windham 06266, it is worth more than 23% of them ($290,147 against a typical $327,093), its price per square foot is higher than 69% of them ($263 against a typical $231), it is bigger than 20% of them (1,104 ft² against a typical 1,436 ft²), its lot is bigger than 10% of them (0.34 ac against a typical 0.92 ac) and it is newer than 63% of them (1966 against a typical 1961). Measured against all of Southeastern Connecticut County, it is worth more than 15% 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 249 Highland View Dr, South Windham, CT?

The 2025 property tax bill for 249 Highland View Dr, South Windham, CT was $4,632. The county assessed it at $155,160.

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