4414 Winchester Dr
Portsmouth, VA 23707
3 bd 1 ba 1,258 sqft Built 1950 Lot 8,712 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 | $121,190 | $67,500 | $188,690 | $2,339 |
| 2024 | $121,190 | $67,500 | $188,690 | $2,270 |
| 2023 | $104,950 | $67,500 | $172,450 | $2,241 |
| 2022 | $103,320 | $56,250 | $159,570 | $2,074 |
| 2021 | $96,020 | $49,420 | $145,440 | $1,890 |
| 2020 | $96,020 | $47,070 | $143,090 | $1,860 |
| 2019 | $95,210 | $47,070 | $142,280 | $1,849 |
| 2018 | $95,210 | $47,070 | $142,280 | $1,849 |
| 2017 | $95,210 | $47,070 | $142,280 | $1,849 |
| 2016 | $95,210 | $47,070 | $142,280 | $1,849 |
| 2015 | $95,210 | $47,070 | $142,280 | $1,849 |
| 2014 | $95,210 | $47,070 | $142,280 | $1,806 |
| 2013 | $95,210 | $47,070 | $142,280 | $1,917 |
| 2012 | $95,210 | $47,070 | $142,280 | $1,917 |
| 2010 | $106,920 | $47,070 | $153,990 | $1,909 |
| 2009 | $106,920 | $47,070 | $153,990 | $2,089 |
| 2008 | $121,470 | $47,070 | $168,540 | $2,039 |
| 2007 | $110,420 | $44,400 | $154,820 | $1,950 |
Property facts
Year built
1950
Property type
single_family
Stories
1
Beds
3
Baths
1
Living area
1,258 sqft
Lot size
8,712 sqft
ZIP code
23707
City
Portsmouth
Street
Winchester Dr
Coordinates
36.82616, -76.35766
Comparable properties nearby
Frequently asked questions
When did 4414 Winchester Dr last sell?
No public-record sale is on file for 4414 Winchester Dr.
What is the current tax assessment for 4414 Winchester Dr?
The most recent total assessment for 4414 Winchester Dr (year 2025) is $188,690 with $2,339 in property tax.
When was 4414 Winchester Dr built?
4414 Winchester Dr was built in 1950.
How does 4414 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 4414 Winchester Dr?
4414 Winchester Dr is a 3 bed, 1 bath, 1,258 sqft, 8,712 sqft lot single_family.
Is 4414 Winchester Dr a flip candidate?
No — 4414 Winchester Dr does not appear in our flips dataset.
Is 4414 Winchester Dr a tax-appeal candidate?
No — 4414 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
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