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Single Family ResidenceResidential
$2,917,705$533 / 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 Jul 14, 2026
Last sold for $1,600,000 on Nov 29, 2005

277 CHESTNUT ST

WINNETKA, IL 60093
7
Beds
6 / 3
Baths
5,472 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.
0.32 ac
Lot SizeThe size of the land the home sits on, from county records.
1923
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
15
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

$2.9M
$2.6M low$3.2M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$1,600,000 · Nov 29, 2005
Est. Owner EquityRoughly how much of the home's value the owner would keep after paying off known loans. It is our estimate minus the loans still owed.$2,317,705
Est. Lendable EquityThe part of the owner's equity a lender would typically let them borrow against — about 80% of their equity.$1,854,164
Loan-to-ValueHow much is still owed on the home compared to what it is worth. 80% means loans equal 80% of our estimate, so it shifts when the estimate does.20%
1st MortgageA loan still believed to be open on this home, in the order lenders get repaid. The first position is paid back before the second.$600,000
HSBC MORTGAGE CORP (USA) · R · recorded Nov 29, 2005

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$43,584 (2023)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$188,000 (2024)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$38,569
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$149,431
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$187,999
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$1,880,000

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.33
1
FloodProjected flooding risk from rivers, heavy rain, and storm surge, scored 0 to 100. Higher is riskier.
1
WildfireProjected wildfire risk, scored 0 to 100, based on how much land burns in a typical year. Higher is riskier.
61
HeatProjected heat risk, scored 0 to 100, based on how many extremely hot days a year are expected. Higher is riskier.
66
StormProjected risk from heavy rainstorms, scored 0 to 100, based on how often extreme rainfall is expected. Higher is riskier.
40
DroughtProjected water shortage risk, scored 0 to 100. Higher means more strain on the local water supply.

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.Split Level
CountyCook
Lot (acres)The size of the land the home sits on, from county records.0.32
ConstructionThe main material the home's frame and walls are built from.Frame (Unspecified)
RoofThe main material covering the roof, such as asphalt shingle or tile.Composition Shingle
HeatingThe type of heating system in the home.Hot Water
CoolingThe type of cooling or air conditioning in the home.Central
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, Detached

Transaction History(1)

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
Crow Island Elementary SchoolA+
Elementary · Grades KG–4 · 0.6 mi
H
New Trier Township High School - WinnetkaA-
High · Grades 10–12 · 0.8 mi
M
The Carleton W. Washburne SchoolA
Middle · Grades 7–8 · 0.9 mi

District: Winnetka School District 36

Neighborhood · ZIP 60093These 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.53
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.117
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.41

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.94%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.38%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.3.3%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.7%
PopulationHow many people live in this area.19,121
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.1,952 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$236,385
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$357,267
Average tempThe average temperature here across a full year.49°F
Annual precipHow much rain and melted snow falls here in a typical year.37 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.54%

Ownership

OccupancyWhether the owner appears to live here or somewhere else. It is inferred from the mailing address on record.Owner occupied
Company ownedWhether the owner is a company or trust rather than a person.No

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

277 Chestnut 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.

  • Among the most valuable homes in Cook County
  • Costs more per square foot than 97% of homes in Cook County
  • Bigger than 98% of homes in Cook County
  • Has a bigger lot than 78% of homes in Cook County
  • Older than 83% of homes in Winnetka 60093

What homes are worth in Winnetka 60093

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

This home
$291K$5.5M

This home is worth more than 85% of homes in Winnetka 60093.

How it measures up in Winnetka 60093

The dot is this home. The mark in the middle is the typical home in Winnetka 60093.

Estimated value$2,917,705
CheaperTypical $1,609,473Pricier

Pricier than 85% of homes nearby

Price per ft²$533
CheaperTypical $547Pricier

Pricier than 47% of homes nearby

Living area5,472 ft²
SmallerTypical 2,929 ft²Bigger

Bigger than 90% of homes nearby

Lot size0.32 ac
SmallerTypical 0.3 acBigger

Bigger than 52% of homes nearby

Year built1923
OlderTypical 1956Newer

Newer than 17% of homes nearby

How 277 Chestnut St ranks against every home in each area.
MeasureThis homeWinnetka 60093Cook County
Estimated valuepricier than$2,917,70585% of homesalmost all homes
Price per ft²pricier than$53347% of homes97% of homes
Living areabigger than5,472 ft²90% of homes98% of homes
Lot sizebigger than0.32 ac52% of homes78% of homes
Year builtnewer than192317% of homes20% of homes

About 277 Chestnut St

How much is 277 Chestnut St, Winnetka, IL worth?

The TopHap Estimate for 277 Chestnut St, Winnetka, IL is $2,917,705 as of Jul 14, 2026. The likely range is $2,621,562 to $3,213,848. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 277 Chestnut St, Winnetka, IL last sell?

277 Chestnut St, Winnetka, IL last sold on Nov 29, 2005 for $1,600,000, according to the county's recorded deed.

How big is 277 Chestnut St, Winnetka, IL?

277 Chestnut St, Winnetka, IL has 7 bedrooms, 6 bathrooms, 5,472 square feet of living space and a 0.32-acre lot.

When was 277 Chestnut St, Winnetka, IL built?

277 Chestnut St, Winnetka, IL was built in 1923, making it 103 years old. It is a split level home. The building has 2 stories.

What schools serve 277 Chestnut St, Winnetka, IL?

277 Chestnut St, Winnetka, IL is assigned to Crow Island Elementary School (elementary), rated A+; New Trier Township High School - Winnetka (high), rated A-; The Carleton W. Washburne School (middle), rated A. All sit in Winnetka School District 36. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 277 Chestnut St, Winnetka, IL compare to other homes in Winnetka 60093?

Among the 7,008 homes in Winnetka 60093, it is worth more than 85% of them ($2,917,705 against a typical $1,609,473), its price per square foot is higher than 47% of them ($533 against a typical $547), it is bigger than 90% of them (5,472 ft² against a typical 2,929 ft²), its lot is bigger than 52% of them (0.32 ac against a typical 0.3 ac) and it is newer than 17% of them (1923 against a typical 1956). Measured against all of Cook County, it is worth more than almost all 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 277 Chestnut St, Winnetka, IL?

The 2023 property tax bill for 277 Chestnut St, Winnetka, IL was $43,584. The county assessed it at $188,000.

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