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Single Family ResidenceResidential
$660,104$307 / 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 92How 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 $449,000 on Aug 18, 2021

27 WINDING RD

MADISON, CT 06443
3
Beds
2.5
Baths
2,152 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.
0.95 ac
Lot SizeThe size of the land the home sits on, from county records.
1968
Year BuiltThe year the home was originally built, according to county records.
1
StoriesHow many floors the home has above ground.
6
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$660K
$606K low$715K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$449,000 · Aug 18, 2021

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$8,093 (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.$360,800 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$119,700
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$241,100
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$360,800
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$515,429

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.42
1
FloodProjected flooding risk from rivers, heavy rain, and storm surge, scored 0 to 100. Higher is riskier.
17
WildfireProjected wildfire risk, scored 0 to 100, based on how much land burns in a typical year. Higher is riskier.
58
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.
39
DroughtProjected water shortage risk, scored 0 to 100. Higher means more strain on the local water supply.
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.minimal

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
StyleThe architectural style of the home, such as ranch or colonial.Ranch
CountySOUTH CENTRAL CONNECTICUT
Lot (acres)The size of the land the home sits on, from county records.0.95
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
GarageWhether the property has a garage, and details like whether it is attached to the home.Garage, Attached
PoolWhether the property has a pool, and what kind, such as in-ground.No

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
Kathleen H. Ryerson Elementary SchoolA+
Elementary · Grades KG–3 · 1.0 mi
M
Walter C. Polson Middle SchoolA
Middle · Grades 6–8 · 3.3 mi
H
Daniel Hand High SchoolA+
High · Grades 9–12 · 3.5 mi

District: Madison School District

Neighborhood · ZIP 06443These 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.85
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 100.57

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.88%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.36%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.2.5%
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.17,380
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.456 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$148,243
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$186,046
Average tempThe average temperature here across a full year.50°F
Annual precipHow much rain and melted snow falls here in a typical year.50 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

27 Winding Rd 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 82% of homes in South Central Connecticut County
  • Costs less per square foot than 77% of homes in Madison 06443
  • Bigger than 75% of homes in South Central Connecticut County
  • Has a bigger lot than 82% of homes in South Central Connecticut County

What homes are worth in Madison 06443

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

This home
$372K$2.5M

This home is worth more than 36% of homes in Madison 06443.

How it measures up in Madison 06443

The dot is this home. The mark in the middle is the typical home in Madison 06443.

Estimated value$660,104
CheaperTypical $743,084Pricier

Pricier than 36% of homes nearby

Price per ft²$307
CheaperTypical $348Pricier

Pricier than 23% of homes nearby

Living area2,152 ft²
SmallerTypical 2,146 ft²Bigger

Bigger than 51% of homes nearby

Lot size0.95 ac
SmallerTypical 1.11 acBigger

Bigger than 35% of homes nearby

Year built1968
OlderTypical 1975Newer

Newer than 36% of homes nearby

How 27 Winding Rd ranks against every home in each area.
MeasureThis homeMadison 06443South Central Connecticut County
Estimated valuepricier than$660,10436% of homes82% of homes
Price per ft²pricier than$30723% of homes58% of homes
Living areabigger than2,152 ft²51% of homes75% of homes
Lot sizebigger than0.95 ac35% of homes82% of homes
Year builtnewer than196836% of homes60% of homes

About 27 Winding Rd

How much is 27 Winding Rd, Madison, CT worth?

The TopHap Estimate for 27 Winding Rd, Madison, CT is $660,104 as of Sep 24, 2026. The likely range is $605,549 to $714,659. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 27 Winding Rd, Madison, CT last sell?

27 Winding Rd, Madison, CT last sold on Aug 18, 2021 for $449,000, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.

How big is 27 Winding Rd, Madison, CT?

27 Winding Rd, Madison, CT has 3 bedrooms, 2.5 bathrooms, 2,152 square feet of living space and a 0.95-acre lot.

When was 27 Winding Rd, Madison, CT built?

27 Winding Rd, Madison, CT was built in 1968, making it 58 years old. It is a ranch home. The building has 1 story.

What schools serve 27 Winding Rd, Madison, CT?

27 Winding Rd, Madison, CT is assigned to Kathleen H. Ryerson Elementary School (elementary), rated A+; Walter C. Polson Middle School (middle), rated A; Daniel Hand High School (high), rated A+. All sit in Madison School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 27 Winding Rd, Madison, CT compare to other homes in Madison 06443?

Among the 7,251 homes in Madison 06443, it is worth more than 36% of them ($660,104 against a typical $743,084), its price per square foot is higher than 23% of them ($307 against a typical $348), it is bigger than 51% of them (2,152 ft² against a typical 2,146 ft²), its lot is bigger than 35% of them (0.95 ac against a typical 1.11 ac) and it is newer than 36% of them (1968 against a typical 1975). Measured against all of South Central Connecticut County, it is worth more than 82% 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 27 Winding Rd, Madison, CT?

The 2025 property tax bill for 27 Winding Rd, Madison, CT was $8,093. The county assessed it at $360,800.

More homes on Winding Rd

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