NOT LISTED FOR SALE

1239 Windward Dr Osprey, FL 34229

Estimated Value: $1,057,561 - $1,240,000

4 Beds
3 Baths
4,253 Sq Ft
$272/Sq Ft Est. Value

About This Home

This home is located at 1239 Windward Dr, Osprey, FL 34229 and is currently estimated at $1,157,140, approximately $272 per square foot. 1239 Windward Dr is a home located in Sarasota County with nearby schools including Laurel Nokomis School, Venice High School, and European Academy Of Early Education.

Ownership History

Date Name Owned For Owner Type

Purchase Details

Closed on
Jun 12, 2025
Sold by
Jennings Robert J and Jennings Karen Marie
Bought by
Jennings Family Revocable Trust and Jennings
Current Estimated Value
$1,157,140

Purchase Details

Closed on
May 9, 2014
Sold by
Jennings Karen J and Jennings Robert J
Bought by
Jennings Robert J and Johnston Jennings Karen Marie

Purchase Details

Closed on
Aug 20, 2009
Sold by
Jennings Robert J and Jennings Karen J
Bought by
Jennings Karen J

Purchase Details

Closed on
Dec 6, 2005
Sold by
Rankin John D and Walck Roberta J
Bought by
Jennings Robert J and Jennings Karen J

Purchase Details

Closed on
Oct 31, 1997
Sold by
Fick Charles M and Fick Charles M
Bought by
Rankin John D and Walck Roberta J

Purchase Details

Closed on
Oct 31, 1995
Sold by
Fick Charles W and Fick Charles M
Bought by
Fick Charles M
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
Collateral Analytics

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ICE

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First American

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Quantarium

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Average Value
Not Available
List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Purchase History

Date Buyer Sale Price Title Company
Jennings Family Revocable Trust $100 None Listed On Document
Jennings Robert J -- Attorney
Jennings Karen J -- Attorney
Jennings Robert J $914,000 Riddell Title & Escrow Llc
Rankin John D $390,000 --
Fick Charles M -- --
Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $5,614 $494,962 -- --
2024 $5,443 $481,013 -- --
2023 $5,443 $467,003 $0 $0
2022 $5,368 $453,401 $0 $0
2021 $5,237 $440,195 $0 $0
2020 $4,923 $406,800 $0 $0
2019 $4,761 $397,654 $0 $0
2018 $4,655 $390,239 $0 $0
2017 $4,634 $382,213 $0 $0
2016 $4,623 $411,200 $117,700 $293,500
2015 $4,709 $395,800 $117,700 $278,100
2014 $4,691 $346,500 $0 $0
Source: Public Records

Map

Florida Sarasota County Osprey 34229

1239 Windward Dr, Osprey, FL

Not Listed for Sale

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