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Residential (General/Single)Residential
$1,128,622$299 / 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

14285 CHESTERWOOD DR

BROOKFIELD, WI 53005
4
Beds
4.5
Baths
3,776 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.
0.69 ac
Lot SizeThe size of the land the home sits on, from county records.
1993
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
9
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$1.1M
$990K low$1.3M high

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$10,633 (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.$908,200 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$210,000
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$698,200
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$1,022,700

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.35
1
FloodProjected flooding risk from rivers, heavy rain, and storm surge, scored 0 to 100. Higher is riskier.
12
WildfireProjected wildfire risk, scored 0 to 100, based on how much land burns in a typical year. Higher is riskier.
56
HeatProjected heat risk, scored 0 to 100, based on how many extremely hot days a year are expected. Higher is riskier.
69
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.Residential (General/Single)
CountyWAUKESHA
Lot (acres)The size of the land the home sits on, from county records.0.69
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(2)

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.

H
Brookfield East High SchoolA+
High · Grades 9–12 · 0.4 mi
E
Dixon Elementary SchoolA
Elementary · Grades PK–5 · 1.7 mi
M
Pilgrim Park Middle SchoolA
Middle · Grades 6–8 · 2.5 mi

District: Elmbrook School District

Neighborhood · ZIP 53005These 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.59
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.82
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.27

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.96%
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.2.1%
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.22,154
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.1,501 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$124,763
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$158,323
Average tempThe average temperature here across a full year.47°F
Annual precipHow much rain and melted snow falls here in a typical year.34 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.54%

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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

14285 Chesterwood Dr 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 Brookfield 53005
  • Costs more per square foot than 82% of homes in Waukesha County
  • Bigger than 98% of homes in Brookfield 53005
  • Has a bigger lot than 77% of homes in Brookfield 53005
  • Newer than 95% of homes in Brookfield 53005

What homes are worth in Brookfield 53005

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

This home
$300K$1M

This home is worth more than almost all homes in Brookfield 53005.

How it measures up in Brookfield 53005

The dot is this home. The mark in the middle is the typical home in Brookfield 53005.

Estimated value$1,128,622
CheaperTypical $482,830Pricier

Pricier than almost all homes nearby

Price per ft²$299
CheaperTypical $258Pricier

Pricier than 81% of homes nearby

Living area3,776 ft²
SmallerTypical 1,878 ft²Bigger

Bigger than 98% of homes nearby

Lot size0.69 ac
SmallerTypical 0.55 acBigger

Bigger than 77% of homes nearby

Year built1993
OlderTypical 1960Newer

Newer than 95% of homes nearby

How 14285 Chesterwood Dr ranks against every home in each area.
MeasureThis homeBrookfield 53005Waukesha County
Estimated valuepricier than$1,128,622almost all homes96% of homes
Price per ft²pricier than$29981% of homes82% of homes
Living areabigger than3,776 ft²98% of homes95% of homes
Lot sizebigger than0.69 ac77% of homes63% of homes
Year builtnewer than199395% of homes74% of homes

About 14285 Chesterwood Dr

How much is 14285 Chesterwood Dr, Brookfield, WI worth?

The TopHap Estimate for 14285 Chesterwood Dr, Brookfield, WI is $1,128,622 as of Sep 24, 2026. The likely range is $989,766 to $1,267,478. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 14285 Chesterwood Dr, Brookfield, WI last sell?

14285 Chesterwood Dr, Brookfield, WI last sold on Jan 1, 1900, according to the county's recorded deed.

How big is 14285 Chesterwood Dr, Brookfield, WI?

14285 Chesterwood Dr, Brookfield, WI has 4 bedrooms, 4.5 bathrooms, 3,776 square feet of living space and a 0.69-acre lot.

When was 14285 Chesterwood Dr, Brookfield, WI built?

14285 Chesterwood Dr, Brookfield, WI was built in 1993, making it 33 years old. The building has 2 stories.

What schools serve 14285 Chesterwood Dr, Brookfield, WI?

14285 Chesterwood Dr, Brookfield, WI is assigned to Brookfield East High School (high), rated A+; Dixon Elementary School (elementary), rated A; Pilgrim Park Middle School (middle), rated A. All sit in Elmbrook School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 14285 Chesterwood Dr, Brookfield, WI compare to other homes in Brookfield 53005?

Among the 7,726 homes in Brookfield 53005, it is worth more than almost all of them ($1,128,622 against a typical $482,830), its price per square foot is higher than 81% of them ($299 against a typical $258), it is bigger than 98% of them (3,776 ft² against a typical 1,878 ft²), its lot is bigger than 77% of them (0.69 ac against a typical 0.55 ac) and it is newer than 95% of them (1993 against a typical 1960). Measured against all of Waukesha County, it is worth more than 96% 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 14285 Chesterwood Dr, Brookfield, WI?

The 2025 property tax bill for 14285 Chesterwood Dr, Brookfield, WI was $10,633. The county assessed it at $908,200.

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