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Single Family ResidenceResidential
$1,220,524$381 / 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 Aug 30, 2026
Last sold for $318,000 on Oct 16, 1992

27 WINESAP RD

STAMFORD, CT 06903
4
Beds
3.5
Baths
3,200 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.
1 ac
Lot SizeThe size of the land the home sits on, from county records.
1963
Year BuiltThe year the home was originally built, according to county records.
1
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.
2
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$1.2M
$1.1M low$1.4M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$318,000 · Oct 16, 1992

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$14,797 (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.$635,880 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$255,450
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$380,430
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$635,880
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$445,116

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.Raised Ranch
CountyWESTERN CONNECTICUT
Lot (acres)The size of the land the home sits on, from county records.1.00
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Hot Water
CoolingThe type of cooling or air conditioning in the home.Yes
FireplaceWhether the home has a fireplace, and what kind.Yes
GarageWhether the property has a garage, and details like whether it is attached to the home.Garage, Basement
PoolWhether the property has a pool, and what kind, such as in-ground.Pool W/Hot Tub/Spa
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(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.

E
Northeast SchoolC+
Elementary · Grades KG–5 · 2.8 mi
M
Turn of River SchoolD+
Middle · Grades 6–8 · 4.5 mi
H
Westhill High SchoolD+
High · Grades 9–12 · 4.8 mi

District: Stamford School District

Neighborhood · ZIP 06903These 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.35
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.118
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.96

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.2.6%
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.16,237
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.876 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$199,285
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$228,302
Average tempThe average temperature here across a full year.51°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

27 Winesap 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 70% of homes in Western Connecticut County
  • Bigger than 80% of homes in Western Connecticut County
  • Has a smaller lot than 68% of homes in Stamford 06903

What homes are worth in Stamford 06903

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

This home
$710K$2.5M

This home is worth more than 59% of homes in Stamford 06903.

How it measures up in Stamford 06903

The dot is this home. The mark in the middle is the typical home in Stamford 06903.

Estimated value$1,220,524
CheaperTypical $1,155,979Pricier

Pricier than 59% of homes nearby

Price per ft²$381
CheaperTypical $382Pricier

Pricier than 49% of homes nearby

Living area3,200 ft²
SmallerTypical 3,103 ft²Bigger

Bigger than 54% of homes nearby

Lot size1 ac
SmallerTypical 1.07 acBigger

Bigger than 32% of homes nearby

Year built1963
OlderTypical 1965Newer

Newer than 45% of homes nearby

How 27 Winesap Rd ranks against every home in each area.
MeasureThis homeStamford 06903Western Connecticut County
Estimated valuepricier than$1,220,52459% of homes70% of homes
Price per ft²pricier than$38149% of homes39% of homes
Living areabigger than3,200 ft²54% of homes80% of homes
Lot sizebigger than1 ac32% of homes62% of homes
Year builtnewer than196345% of homes44% of homes

About 27 Winesap Rd

How much is 27 Winesap Rd, Stamford, CT worth?

The TopHap Estimate for 27 Winesap Rd, Stamford, CT is $1,220,524 as of Aug 30, 2026. The likely range is $1,078,500 to $1,362,548. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 27 Winesap Rd, Stamford, CT last sell?

27 Winesap Rd, Stamford, CT last sold on Oct 16, 1992 for $318,000, according to the county's recorded deed.

How big is 27 Winesap Rd, Stamford, CT?

27 Winesap Rd, Stamford, CT has 4 bedrooms, 3.5 bathrooms, 3,200 square feet of living space and a 1.00-acre lot.

When was 27 Winesap Rd, Stamford, CT built?

27 Winesap Rd, Stamford, CT was built in 1963, making it 63 years old. It is a raised ranch home. The building has 1 story.

What schools serve 27 Winesap Rd, Stamford, CT?

27 Winesap Rd, Stamford, CT is assigned to Northeast School (elementary), rated C+; Turn of River School (middle), rated D+; Westhill High School (high), rated D+. All sit in Stamford School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 27 Winesap Rd, Stamford, CT compare to other homes in Stamford 06903?

Among the 5,184 homes in Stamford 06903, it is worth more than 59% of them ($1,220,524 against a typical $1,155,979), its price per square foot is higher than 49% of them ($381 against a typical $382), it is bigger than 54% of them (3,200 ft² against a typical 3,103 ft²), its lot is bigger than 32% of them (1 ac against a typical 1.07 ac) and it is newer than 45% of them (1963 against a typical 1965). Measured against all of Western Connecticut County, it is worth more than 70% 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 Winesap Rd, Stamford, CT?

The 2025 property tax bill for 27 Winesap Rd, Stamford, CT was $14,797. The county assessed it at $635,880.

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