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CondominiumResidential
$709,616$264 / 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 94How 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 $695,000 on Nov 24, 2025

18 WINDING TRL

MIDDLEBURY, CT 06762
3
Beds
2.5
Baths
2,688 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.
2014
Year BuiltThe year the home was originally built, according to county records.
2
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

$710K
$670K low$749K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$695,000 · Nov 24, 2025

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$13,216 (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.$406,400 (2025)
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$406,400
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$406,400
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$580,571

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
39
FloodProjected flooding risk from rivers, heavy rain, and storm surge, scored 0 to 100. Higher is riskier.
19
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.
97
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.
Projected Flood DepthHow deep a serious flood is expected to get here at some point in the next 30 years. Shown in inches.8 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.30%
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.Condominium
StyleThe architectural style of the home, such as ranch or colonial.Condo/Apartment
CountyNAUGATUCK VALLEY
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
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Deck

Transaction History(3)

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
Long Meadow Elementary SchoolC
Elementary · Grades PK–5 · 1.3 mi
H
Pomperaug Regional High SchoolA
High · Grades 9–12 · 1.6 mi
M
Memorial Middle SchoolA
Middle · Grades 6–8 · 2.9 mi

District: Regional School District 15

Neighborhood · ZIP 06762These 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.110
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.104
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.69

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.95%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.30%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.5.8%
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.7,893
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.429 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$134,216
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$150,984
Average tempThe average temperature here across a full year.49°F
Annual precipHow much rain and melted snow falls here in a typical year.52 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

18 Winding Trl 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 92% of homes in Naugatuck Valley County
  • Bigger than 88% of homes in Naugatuck Valley County
  • Newer than 98% of homes in Naugatuck Valley County

What homes are worth in Middlebury 06762

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

This home
$282K$1.4M

This home is worth more than 82% of homes in Middlebury 06762.

How it measures up in Middlebury 06762

The dot is this home. The mark in the middle is the typical home in Middlebury 06762.

Estimated value$709,616
CheaperTypical $538,873Pricier

Pricier than 82% of homes nearby

Price per ft²$264
CheaperTypical $265Pricier

Pricier than 50% of homes nearby

Living area2,688 ft²
SmallerTypical 2,072 ft²Bigger

Bigger than 75% of homes nearby

Year built2014
OlderTypical 1973Newer

Newer than 91% of homes nearby

How 18 Winding Trl ranks against every home in each area.
MeasureThis homeMiddlebury 06762Naugatuck Valley County
Estimated valuepricier than$709,61682% of homes92% of homes
Price per ft²pricier than$26450% of homes52% of homes
Living areabigger than2,688 ft²75% of homes88% of homes
Year builtnewer than201491% of homes98% of homes

About 18 Winding Trl

How much is 18 Winding Trl, Middlebury, CT worth?

The TopHap Estimate for 18 Winding Trl, Middlebury, CT is $709,616 as of Sep 24, 2026. The likely range is $670,389 to $748,843. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 18 Winding Trl, Middlebury, CT last sell?

18 Winding Trl, Middlebury, CT last sold on Nov 24, 2025 for $695,000, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.

How big is 18 Winding Trl, Middlebury, CT?

18 Winding Trl, Middlebury, CT has 3 bedrooms, 2.5 bathrooms and 2,688 square feet of living space.

When was 18 Winding Trl, Middlebury, CT built?

18 Winding Trl, Middlebury, CT was built in 2014, making it 12 years old. It is a condo/apartment home. The building has 2 stories.

What schools serve 18 Winding Trl, Middlebury, CT?

18 Winding Trl, Middlebury, CT is assigned to Long Meadow Elementary School (elementary), rated C; Pomperaug Regional High School (high), rated A; Memorial Middle School (middle), rated A. All sit in Regional School District 15. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 18 Winding Trl, Middlebury, CT compare to other homes in Middlebury 06762?

Among the 3,076 homes in Middlebury 06762, it is worth more than 82% of them ($709,616 against a typical $538,873), its price per square foot is higher than 50% of them ($264 against a typical $265), it is bigger than 75% of them (2,688 ft² against a typical 2,072 ft²) and it is newer than 91% of them (2014 against a typical 1973). Measured against all of Naugatuck Valley County, it is worth more than 92% 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 18 Winding Trl, Middlebury, CT?

The 2025 property tax bill for 18 Winding Trl, Middlebury, CT was $13,216. The county assessed it at $406,400.

More homes on Winding Trl

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