Skip to content
Skip to content
TopHapOpen in map
Single Family ResidenceResidential
$2,429,769$446 / 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 88How 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 $825,000 on May 3, 1999

14 WINDING LN

WESTPORT, CT 06880
5
Beds
5 / 2
Baths
5,444 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.
0.94 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.
2
StoriesHow many floors the home has above ground.
10
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$2.4M
$2.1M low$2.7M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$825,000 · May 3, 1999

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$28,735 (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.$1,523,600 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$560,200
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$963,400
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$1,523,600
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$1,066,520

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.Cape Cod
CountyWESTERN CONNECTICUT
Lot (acres)The size of the land the home sits on, from county records.0.94
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

Transaction History(4)

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.

M
Coleytown Middle SchoolA+
Middle · Grades 6–8 · 0.2 mi
E
King's Highway Elementary SchoolA+
Elementary · Grades KG–5 · 0.8 mi
H
Staples High SchoolA+
High · Grades 9–12 · 2.6 mi

District: Westport School District

Neighborhood · ZIP 06880These 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.94
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.110
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.82

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.36%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.5.2%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.9%
PopulationHow many people live in this area.30,681
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.1,183 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$219,182
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$324,431
Average tempThe average temperature here across a full year.52°F
Annual precipHow much rain and melted snow falls here in a typical year.49 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.58%

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

14 Winding Ln 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 88% of homes in Western Connecticut County
  • Costs less per square foot than 95% of homes in Old Hill
  • Bigger than 96% of homes in Western Connecticut County
  • Has a smaller lot than 72% of homes in Old Hill
  • Newer than 93% of homes in Western Connecticut County

What homes are worth in Westport 06880

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

This home
$595K$6.6M

This home is worth more than 61% of homes in Westport 06880.

How it measures up in Westport 06880

The dot is this home. The mark in the middle is the typical home in Westport 06880.

Estimated value$2,429,769
CheaperTypical $2,060,705Pricier

Pricier than 61% of homes nearby

Price per ft²$446
CheaperTypical $712Pricier

Pricier than 5% of homes nearby

Living area5,444 ft²
SmallerTypical 2,910 ft²Bigger

Bigger than 87% of homes nearby

Lot size0.94 ac
SmallerTypical 1 acBigger

Bigger than 48% of homes nearby

Year built2006
OlderTypical 1965Newer

Newer than 85% of homes nearby

How 14 Winding Ln ranks against every home in each area.
MeasureThis homeOld HillWestport 06880Western Connecticut County
Estimated valuepricier than$2,429,76970% of homes61% of homes88% of homes
Price per ft²pricier than$4465% of homes5% of homes56% of homes
Living areabigger than5,444 ft²86% of homes87% of homes96% of homes
Lot sizebigger than0.94 ac28% of homes48% of homes56% of homes
Year builtnewer than200689% of homes85% of homes93% of homes

About 14 Winding Ln

How much is 14 Winding Ln, Westport, CT worth?

The TopHap Estimate for 14 Winding Ln, Westport, CT is $2,429,769 as of Sep 24, 2026. The likely range is $2,128,277 to $2,731,261. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 14 Winding Ln, Westport, CT last sell?

14 Winding Ln, Westport, CT last sold on May 3, 1999 for $825,000, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.

How big is 14 Winding Ln, Westport, CT?

14 Winding Ln, Westport, CT has 5 bedrooms, 5 bathrooms, 5,444 square feet of living space and a 0.94-acre lot.

When was 14 Winding Ln, Westport, CT built?

14 Winding Ln, Westport, CT was built in 2006, making it 20 years old. It is a cape cod home. The building has 2 stories.

What schools serve 14 Winding Ln, Westport, CT?

14 Winding Ln, Westport, CT is assigned to Coleytown Middle School (middle), rated A+; King's Highway Elementary School (elementary), rated A+; Staples High School (high), rated A+. All sit in Westport School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 14 Winding Ln, Westport, CT compare to other homes in Westport 06880?

Among the 9,793 homes in Westport 06880, it is worth more than 61% of them ($2,429,769 against a typical $2,060,705), its price per square foot is higher than 5% of them ($446 against a typical $712), it is bigger than 87% of them (5,444 ft² against a typical 2,910 ft²), its lot is bigger than 48% of them (0.94 ac against a typical 1 ac) and it is newer than 85% of them (2006 against a typical 1965). Measured against all of Western Connecticut County, it is worth more than 88% 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 14 Winding Ln, Westport, CT?

The 2025 property tax bill for 14 Winding Ln, Westport, CT was $28,735. The county assessed it at $1,523,600.

More homes on Winding Ln

Closest homes

More homes in Westport 06880

Assigned schools

Explore the area

See this home in context

Open 14 Winding Ln 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