5365 Winchester Dr
Sarasota, FL 34234
3 bd 2 ba 1,804 sqft Built 1953 Lot 14,810 sqft single_family
Most recent sale
$805,000
Apr 29, 2022
Location
Timeline: Sale, Listing & Tax History
Recorded events
| Date | Event | Price | Source |
|---|---|---|---|
| Apr 29, 2022 | Sold | $805,000 | MLS #A4525012 |
| Feb 11, 2022 | Listed | $850,000 | MLS #A4525012 |
| Feb 12, 2020 | Listing removed | $874,900 | StellarMLS |
| Aug 17, 2016 | Sold | $399,000 | MLS #A4144614 |
| Apr 27, 2016 | Price changed | $399,000 | MLS #A4144614 |
| Mar 9, 2016 | Price changed | $425,000 | MLS #A4144614 |
| Feb 2, 2016 | Listed | $445,000 | MLS #A4144614 |
| Nov 1, 2011 | Listing removed | $335,000 | StellarMLS |
| Aug 16, 2011 | Price changed | $335,000 | MLS #A3947136 |
| Aug 7, 2011 | Listed | $349,900 | MLS #A3947136 |
| Apr 18, 2011 | Listing removed | $378,500 | StellarMLS |
| Mar 9, 2011 | Listed | $378,500 | MLS #A3940634 |
| Apr 1, 2009 | Listing removed | $1,350 | StellarMLS |
| Jan 16, 2009 | Listed | $324,900 | MLS #A3901324 |
| Jan 13, 2009 | Listed for rent | $1,350 | StellarMLS |
| Dec 22, 2008 | Sold | $299,250 | Public Record |
| Nov 29, 2008 | Listing removed | $364,500 | StellarMLS |
| Sep 29, 2008 | Listed | $364,500 | MLS #A3895281 |
| Sep 5, 2008 | Listing removed | $395,000 | StellarMLS |
| Jun 6, 2008 | Listed | $395,000 | MLS #A385304 |
| Jun 30, 2007 | Listing removed | $874,900 | StellarMLS |
| Apr 3, 2007 | Listed | $874,900 | MLS #A347677 |
| Aug 11, 2005 | Sold | $270,000 | Public Record |
| Sep 4, 2002 | Sold | $182,000 | Public Record |
| Oct 1, 1978 | Sold | $45,000 | Public Record |
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $282,400 | $340,200 | $622,600 | $9,680 |
| 2023 | $295,900 | $301,200 | $597,100 | $9,128 |
| 2021 | — | — | $297,139 | $4,291 |
| 2020 | — | — | $293,036 | $4,340 |
| 2019 | — | — | $286,448 | $4,223 |
| 2018 | — | — | $274,544 | $4,046 |
| 2017 | — | — | $268,897 | $3,995 |
| 2016 | — | — | $180,074 | $2,602 |
| 2015 | — | — | $178,822 | $2,638 |
| 2014 | — | — | $177,403 | $2,631 |
| 2013 | — | — | $174,781 | $2,620 |
| 2012 | — | — | $171,859 | $2,521 |
| 2011 | — | — | $166,853 | $2,406 |
| 2010 | — | — | $163,500 | $2,384 |
| 2009 | — | — | $202,200 | $3,569 |
| 2008 | — | — | $258,200 | $4,331 |
| 2007 | — | — | $320,700 | $4,959 |
Property facts
Year built
1953
Property type
single_family
Stories
1
Beds
3
Baths
2
Living area
1,804 sqft
Lot size
14,810 sqft
ZIP code
34234
City
Sarasota
Street
Winchester Dr
Coordinates
27.38073, -82.55845
Comparable properties nearby
Investment analysis
Estimates based on local averages — not personalized adviceEstimated monthly rent
$3,337
Gross rental yield
4.97%
Implied cap rate
3.23%
Trend-extrapolated value
—
Frequently asked questions
When did 5365 Winchester Dr last sell?
5365 Winchester Dr most recently sold on Apr 29, 2022 for $805,000.
What is the current tax assessment for 5365 Winchester Dr?
The most recent total assessment for 5365 Winchester Dr (year 2025) is $622,600 with $9,680 in property tax.
How does 5365 Winchester Dr's assessment compare to its last sale price?
The current assessment is 22.7% below the last sale price of $805,000.
When was 5365 Winchester Dr built?
5365 Winchester Dr was built in 1953.
How does 5365 Winchester Dr compare to others on Winchester Dr?
We track 1 other property 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 5365 Winchester Dr?
5365 Winchester Dr is a 3 bed, 2 bath, 1,804 sqft, 14,810 sqft lot single_family.
Is 5365 Winchester Dr a flip candidate?
No — 5365 Winchester Dr does not appear in our flips dataset.
Is 5365 Winchester Dr a tax-appeal candidate?
No — 5365 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
+4.3%
Implied 1-yr
+17.3%
2026 Q3
$1.28M
2026 Q4
$1.28M
ZIP 34234 — Median Price History + Forecast
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Geography
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