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Single Family ResidenceResidential
$295,038$154 / 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
Last sold for $199,900 on Jan 29, 2019

4429 WINCHESTER DR

PORTSMOUTH, VA 23707
3
Beds
2
Baths
1,914 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.
0.24 ac
Lot SizeThe size of the land the home sits on, from county records.
1952
Year BuiltThe year the home was originally built, according to county records.
1
StoriesHow many floors the home has above ground.
6
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$295K
$278K low$312K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$199,900 · Jan 29, 2019

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$3,408 (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.$259,110 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$73,500
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$185,610
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$252,330
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$259,110

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.Ranch
CountyPORTSMOUTH CITY
Lot (acres)The size of the land the home sits on, from county records.0.24
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.Central
CoolingThe type of cooling or air conditioning in the home.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.

E
Westhaven Elementary SchoolF
Elementary · Grades KG–6 · 0.6 mi
H
Manor High SchoolC-
High · Grades 9–12 · 1.5 mi
M
William E. Waters Middle SchoolD-
Middle · Grades 7–8 · 2.3 mi

District: Portsmouth City Public Schools

Neighborhood · ZIP 23707These 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.135
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 100.26

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.91%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.16%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.22%
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.14,578
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.2,692 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$53,523
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$76,323
Average tempThe average temperature here across a full year.59°F
Annual precipHow much rain and melted snow falls here in a typical year.47 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

4429 Winchester 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.

  • Worth more than 66% of homes in Portsmouth 23707
  • Costs less per square foot than 85% of homes in Portsmouth city County
  • Bigger than 77% of homes in Portsmouth city County
  • Has a bigger lot than 79% of homes in Portsmouth 23707

What homes are worth in Portsmouth 23707

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

This home
$142K$515K

This home is worth more than 66% of homes in Portsmouth 23707.

How it measures up in Portsmouth 23707

The dot is this home. The mark in the middle is the typical home in Portsmouth 23707.

Estimated value$295,038
CheaperTypical $262,697Pricier

Pricier than 66% of homes nearby

Price per ft²$154
CheaperTypical $185Pricier

Pricier than 21% of homes nearby

Living area1,914 ft²
SmallerTypical 1,444 ft²Bigger

Bigger than 75% of homes nearby

Lot size0.24 ac
SmallerTypical 0.15 acBigger

Bigger than 79% of homes nearby

Year built1952
OlderTypical 1948Newer

Newer than 61% of homes nearby

How 4429 Winchester Dr ranks against every home in each area.
MeasureThis homePortsmouth 23707Portsmouth city County
Estimated valuepricier than$295,03866% of homes59% of homes
Price per ft²pricier than$15421% of homes15% of homes
Living areabigger than1,914 ft²75% of homes77% of homes
Lot sizebigger than0.24 ac79% of homes58% of homes
Year builtnewer than195261% of homes36% of homes

About 4429 Winchester Dr

How much is 4429 Winchester Dr, Portsmouth, VA worth?

The TopHap Estimate for 4429 Winchester Dr, Portsmouth, VA is $295,038 as of Sep 24, 2026. The likely range is $278,065 to $312,011. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 4429 Winchester Dr, Portsmouth, VA last sell?

4429 Winchester Dr, Portsmouth, VA last sold on Jan 29, 2019 for $199,900, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.

How big is 4429 Winchester Dr, Portsmouth, VA?

4429 Winchester Dr, Portsmouth, VA has 3 bedrooms, 2 bathrooms, 1,914 square feet of living space and a 0.24-acre lot.

When was 4429 Winchester Dr, Portsmouth, VA built?

4429 Winchester Dr, Portsmouth, VA was built in 1952, making it 74 years old. It is a ranch home. The building has 1 story.

What schools serve 4429 Winchester Dr, Portsmouth, VA?

4429 Winchester Dr, Portsmouth, VA is assigned to Westhaven Elementary School (elementary), rated F; Manor High School (high), rated C-; William E. Waters Middle School (middle), rated D-. All sit in Portsmouth City Public Schools. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 4429 Winchester Dr, Portsmouth, VA compare to other homes in Portsmouth 23707?

Among the 5,006 homes in Portsmouth 23707, it is worth more than 66% of them ($295,038 against a typical $262,697), its price per square foot is higher than 21% of them ($154 against a typical $185), it is bigger than 75% of them (1,914 ft² against a typical 1,444 ft²), its lot is bigger than 79% of them (0.24 ac against a typical 0.15 ac) and it is newer than 61% of them (1952 against a typical 1948). Measured against all of Portsmouth city County, it is worth more than 59% 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 4429 Winchester Dr, Portsmouth, VA?

The 2025 property tax bill for 4429 Winchester Dr, Portsmouth, VA was $3,408. The county assessed it at $259,110.

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