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Single Family ResidenceResidential
$418,118$262 / 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

4249 WOODLAND DR

CHESAPEAKE, VA 23321
3
Beds
2
Baths
1,595 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.
1.59 ac
Lot SizeThe size of the land the home sits on, from county records.
1964
Year BuiltThe year the home was originally built, according to county records.
1
StoriesHow many floors the home has above ground.
5
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

$418K
$393K low$443K high

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$3,589 (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.$395,100 (2026)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$201,800
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$193,300
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$355,300
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$395,100

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.46
39
FloodProjected flooding risk from rivers, heavy rain, and storm surge, scored 0 to 100. Higher is riskier.
24
WildfireProjected wildfire risk, scored 0 to 100, based on how much land burns in a typical year. Higher is riskier.
79
HeatProjected heat risk, scored 0 to 100, based on how many extremely hot days a year are expected. Higher is riskier.
78
StormProjected risk from heavy rainstorms, scored 0 to 100, based on how often extreme rainfall is expected. Higher is riskier.
10
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.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.Single Family Residence
CountyCHESAPEAKE CITY
Lot (acres)The size of the land the home sits on, from county records.1.59
ConstructionThe main material the home's frame and walls are built from.Brick
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, Detached
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.Patio · 400 ft²

Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.

E
Edwin W. Chittum Elementary SchoolA
Elementary · Grades PK–5 · 0.8 mi
M
Jolliff Middle SchoolB+
Middle · Grades 6–8 · 1.2 mi
H
Western Branch High SchoolB+
High · Grades 9–12 · 2.9 mi

District: Chesapeake City Public Schools

Neighborhood · ZIP 23321These 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.79
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.83
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.25

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.24%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.5.7%
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.37,912
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.1,420 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$105,100
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$127,739
Average tempThe average temperature here across a full year.59°F
Annual precipHow much rain and melted snow falls here in a typical year.48 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.63%

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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

4249 Woodland 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.

  • Costs more per square foot than 93% of homes in Chesapeake 23321
  • Smaller than 66% of homes in Chesapeake 23321
  • Has a bigger lot than 97% of homes in Chesapeake 23321
  • Older than 88% of homes in Chesapeake 23321

What homes are worth in Chesapeake 23321

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

This home
$159K$757K

This home is worth more than 57% of homes in Chesapeake 23321.

How it measures up in Chesapeake 23321

The dot is this home. The mark in the middle is the typical home in Chesapeake 23321.

Estimated value$418,118
CheaperTypical $394,509Pricier

Pricier than 57% of homes nearby

Price per ft²$262
CheaperTypical $205Pricier

Pricier than 93% of homes nearby

Living area1,595 ft²
SmallerTypical 1,870 ft²Bigger

Bigger than 34% of homes nearby

Lot size1.59 ac
SmallerTypical 0.29 acBigger

Bigger than 97% of homes nearby

Year built1964
OlderTypical 1987Newer

Newer than 12% of homes nearby

How 4249 Woodland Dr ranks against every home in each area.
MeasureThis homeChesapeake 23321Chesapeake city County
Estimated valuepricier than$418,11857% of homes50% of homes
Price per ft²pricier than$26293% of homes84% of homes
Living areabigger than1,595 ft²34% of homes35% of homes
Lot sizebigger than1.59 ac97% of homes94% of homes
Year builtnewer than196412% of homes16% of homes

About 4249 Woodland Dr

How much is 4249 Woodland Dr, Chesapeake, VA worth?

The TopHap Estimate for 4249 Woodland Dr, Chesapeake, VA is $418,118 as of Sep 24, 2026. The likely range is $393,131 to $443,105. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 4249 Woodland Dr, Chesapeake, VA last sell?

4249 Woodland Dr, Chesapeake, VA last sold on Jan 1, 1900, according to the county's recorded deed.

How big is 4249 Woodland Dr, Chesapeake, VA?

4249 Woodland Dr, Chesapeake, VA has 3 bedrooms, 2 bathrooms, 1,595 square feet of living space and a 1.59-acre lot.

When was 4249 Woodland Dr, Chesapeake, VA built?

4249 Woodland Dr, Chesapeake, VA was built in 1964, making it 62 years old. The building has 1 story.

What schools serve 4249 Woodland Dr, Chesapeake, VA?

4249 Woodland Dr, Chesapeake, VA is assigned to Edwin W. Chittum Elementary School (elementary), rated A; Jolliff Middle School (middle), rated B+; Western Branch High School (high), rated B+. All sit in Chesapeake City Public Schools. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 4249 Woodland Dr, Chesapeake, VA compare to other homes in Chesapeake 23321?

Among the 12,724 homes in Chesapeake 23321, it is worth more than 57% of them ($418,118 against a typical $394,509), its price per square foot is higher than 93% of them ($262 against a typical $205), it is bigger than 34% of them (1,595 ft² against a typical 1,870 ft²), its lot is bigger than 97% of them (1.59 ac against a typical 0.29 ac) and it is newer than 12% of them (1964 against a typical 1987). Measured against all of Chesapeake city County, it is worth more than 50% 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 4249 Woodland Dr, Chesapeake, VA?

The 2025 property tax bill for 4249 Woodland Dr, Chesapeake, VA was $3,589. The county assessed it at $395,100.

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