4429 Winchester Dr
Portsmouth, VA 23707
3 bd 2 ba 1,914 sqft Built 1952 Lot 10,454 sqft single_family
No recorded sales
Location
Timeline: Sale, Listing & Tax History
Recorded events
No recorded events
No sale or listing events are on file for this property.
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $185,610 | $73,500 | $259,110 | $3,212 |
| 2024 | $185,610 | $73,500 | $259,110 | $3,103 |
| 2023 | $158,510 | $73,500 | $232,010 | $3,016 |
| 2022 | $155,800 | $61,250 | $217,050 | $2,821 |
| 2021 | $143,610 | $53,810 | $197,420 | $2,566 |
| 2020 | $143,610 | $51,250 | $194,860 | $2,533 |
| 2019 | $142,250 | $51,250 | $193,500 | $2,515 |
| 2018 | $122,830 | $51,250 | $174,080 | $2,263 |
| 2017 | $122,830 | $51,250 | $174,080 | $2,263 |
| 2016 | $122,830 | $51,250 | $174,080 | $2,263 |
| 2015 | $122,830 | $51,250 | $174,080 | $2,263 |
| 2014 | $149,900 | $51,250 | $201,150 | $2,554 |
| 2013 | $149,900 | $51,250 | $201,150 | $2,665 |
| 2012 | $149,900 | $51,250 | $201,150 | $2,665 |
| 2010 | $157,040 | $51,250 | $208,290 | $2,582 |
| 2009 | $157,040 | $51,250 | $208,290 | $2,874 |
| 2008 | $180,590 | $51,250 | $231,840 | $2,805 |
| 2007 | $164,170 | $48,350 | $212,520 | $2,677 |
Property facts
Year built
1952
Property type
single_family
Stories
1
Beds
3
Baths
2
Living area
1,914 sqft
Lot size
10,454 sqft
ZIP code
23707
City
Portsmouth
Street
Winchester Dr
Coordinates
36.82672, -76.35876
Comparable properties nearby
Block-level micro-comps
Same street, ±3 house numbers, sold in the last 24 monthsFrequently asked questions
When did 4429 Winchester Dr last sell?
No public-record sale is on file for 4429 Winchester Dr.
What is the current tax assessment for 4429 Winchester Dr?
The most recent total assessment for 4429 Winchester Dr (year 2025) is $259,110 with $3,212 in property tax.
When was 4429 Winchester Dr built?
4429 Winchester Dr was built in 1952.
How does 4429 Winchester Dr compare to others on Winchester Dr?
We track 8 other properties on Winchester Dr. Browse the list under "Other properties on Winchester Dr" to compare beds, baths, and sale history.
What are the property facts for 4429 Winchester Dr?
4429 Winchester Dr is a 3 bed, 2 bath, 1,914 sqft, 10,454 sqft lot single_family.
Is 4429 Winchester Dr a flip candidate?
No — 4429 Winchester Dr does not appear in our flips dataset.
Is 4429 Winchester Dr a tax-appeal candidate?
No — 4429 Winchester Dr is not currently flagged as a tax-appeal candidate.
Forecast for this area
ZIP-area linear projection — not a per-property automated valuationQuarterly trend
+4.8%
Implied 1-yr
+19.3%
2026 Q2
$404.8K
2026 Q3
$419.7K
ZIP 23707 — Median Price History + Forecast
Explore nearby
Geography
Other properties on Winchester Dr