Skip to content
Skip to content
TopHapOpen in map
Single Family ResidenceResidential
$472,196$281 / 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 90How 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

269 MAIN ST

CHESTER, VT 05143
3
Beds
2.5
Baths
1,680 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.
0.54 ac
Lot SizeThe size of the land the home sits on, from county records.
2006
Year BuiltThe year the home was originally built, according to county records.
7
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$472K
$423K low$521K high

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$4,097 (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.$220,000 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$30,400
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$189,600
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$220,000

Climate Risk

Overall riskThe average of the five hazard scores below, on a 0 to 100 scale. Higher means greater projected risk over the coming decades.50
87
FloodProjected flooding risk from rivers, heavy rain, and storm surge, scored 0 to 100. Higher is riskier.
9
WildfireProjected wildfire risk, scored 0 to 100, based on how much land burns in a typical year. Higher is riskier.
51
HeatProjected heat risk, scored 0 to 100, based on how many extremely hot days a year are expected. Higher is riskier.
96
StormProjected risk from heavy rainstorms, scored 0 to 100, based on how often extreme rainfall is expected. Higher is riskier.
9
DroughtProjected water shortage risk, scored 0 to 100. Higher means more strain on the local water supply.
Projected Flood DepthHow deep a serious flood is expected to get here at some point in the next 30 years. Shown in inches.90 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.51%
FEMA Flood ZoneFEMA's flood zone for this address. Zones starting with A or V are high risk, and lenders usually require flood insurance there.0.2 percent flood zone

Scores 0–100; higher = greater projected risk.

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
CountyWINDSOR
Lot (acres)The size of the land the home sits on, from county records.0.54
RoofThe main material covering the roof, such as asphalt shingle or tile.Shingle
HeatingThe type of heating system in the home.Steam
FireplaceWhether the home has a fireplace, and what kind.Yes
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

Neighborhood · ZIP 05143These 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.104
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.84
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.73%
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.5.6%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.7%
PopulationHow many people live in this area.4,365
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.40 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$76,594
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$100,961
Average tempThe average temperature here across a full year.43°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.49%

Owner Tools

Do you own this home?
Claim this home

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

269 Main 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 72% of homes in Chester 05143
  • Has a smaller lot than 86% of homes in Chester 05143
  • Newer than 93% of homes in Windsor County

What homes are worth in Chester 05143

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

This home
$119K$1.2M

This home is worth more than 72% of homes in Chester 05143.

How it measures up in Chester 05143

The dot is this home. The mark in the middle is the typical home in Chester 05143.

Estimated value$472,196
CheaperTypical $353,839Pricier

Pricier than 72% of homes nearby

Price per ft²$281
CheaperTypical $254Pricier

Pricier than 63% of homes nearby

Living area1,680 ft²
SmallerTypical 1,536 ft²Bigger

Bigger than 58% of homes nearby

Lot size0.54 ac
SmallerTypical 3.82 acBigger

Bigger than 14% of homes nearby

Year built2006
OlderTypical 1974Newer

Newer than 92% of homes nearby

How 269 Main St ranks against every home in each area.
MeasureThis homeChester 05143Windsor County
Estimated valuepricier than$472,19672% of homes57% of homes
Price per ft²pricier than$28163% of homes52% of homes
Living areabigger than1,680 ft²58% of homes57% of homes
Lot sizebigger than0.54 ac14% of homes23% of homes
Year builtnewer than200692% of homes93% of homes

About 269 Main St

How much is 269 Main St, Chester, VT worth?

The TopHap Estimate for 269 Main St, Chester, VT is $472,196 as of Sep 24, 2026. The likely range is $423,445 to $520,947. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 269 Main St, Chester, VT last sell?

269 Main St, Chester, VT last sold on Jan 1, 1900, according to the county's recorded deed.

How big is 269 Main St, Chester, VT?

269 Main St, Chester, VT has 3 bedrooms, 2.5 bathrooms, 1,680 square feet of living space and a 0.54-acre lot.

When was 269 Main St, Chester, VT built?

269 Main St, Chester, VT was built in 2006, making it 20 years old.

How does 269 Main St, Chester, VT compare to other homes in Chester 05143?

Among the 2,476 homes in Chester 05143, it is worth more than 72% of them ($472,196 against a typical $353,839), its price per square foot is higher than 63% of them ($281 against a typical $254), it is bigger than 58% of them (1,680 ft² against a typical 1,536 ft²), its lot is bigger than 14% of them (0.54 ac against a typical 3.82 ac) and it is newer than 92% of them (2006 against a typical 1974). Measured against all of Windsor County, it is worth more than 57% 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 269 Main St, Chester, VT?

The 2025 property tax bill for 269 Main St, Chester, VT was $4,097. The county assessed it at $220,000.

More homes on Main St

Closest homes

More homes in Chester 05143

Explore the area

See this home in context

Open 269 Main St on TopHap’s interactive map to compare it against every sale nearby, overlay school zones and flood risk, and run a CMA.

Open in map
A flyover of TopHap's photorealistic 3D map, with recorded sale prices pinned to homes
Search any address, city, zip, or county…3D$1.9M$6.25MOpen in map