Sarasota County property records for 56 addresses on Winding Oaks Dr, Longboat Key, FL · Last verified October 2026
| Properties | 56 |
|---|---|
| Median Sale Price | $1,000,000 |
| Deeds and Mortgages on File | 68 |
| Median Price per Sqft | $429 |
| Owner Occupied | 66% |
| Median Annual Tax Bill | $9,232 |
| Median Year Built | 1988 |
| Median Ownership Tenure | 6 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3401, #1 Winding Oaks Dr |
2 bd · 2 ba · 2,092 sqft built 1988 | — Sep 2023 | $8,525 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3402, #56 Winding Oaks Dr |
2 bd · 2 ba · 2,039 sqft built 1988 | $1,000,000 Mar 2023 | $9,988 2025 | Assessor + 3 Documents Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3403, #2 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 · 13.8 acres | $565,000 Dec 2012 | $7,429 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3404, #55 Winding Oaks Dr |
2 bd · 2 ba · 2,039 sqft built 1988 | $450,000 Jun 2004 | $8,445 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3405, #3 Winding Oaks Dr |
2 bd · 4 ba · 2,555 sqft built 1988 | $1,200,000 Apr 2024 | $4,628 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3406, #54 Winding Oaks Dr |
2 bd · 2 ba · 2,039 sqft built 1988 | $445,000 Jan 2012 | $5,355 2025 | Assessor + 1 Document Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3407, #4 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $725,000 Dec 2014 | $9,232 2025 | Assessor Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3408, #53 Winding Oaks Dr |
2 bd · 2 ba · 2,039 sqft built 1988 · 13.8 acres | $1,175,000 Mar 2024 | $10,466 2024 | Assessor + 2 Documents Updated Aug 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3409, #5 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $1,042,500 Aug 2020 | $11,572 2025 | Assessor + 3 Documents Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3410, #52 Winding Oaks Dr |
2 bd · 2 ba · 2,039 sqft built 1988 · 13.8 acres | $875,000 Oct 2021 | $9,412 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3411, #6 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $1,695,000 Aug 2022 | $9,042 2025 | Assessor + 2 Documents Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3412, #51 Winding Oaks Dr |
2 bd · 2 ba · 2,039 sqft built 1988 | $590,000 Jul 2016 | $8,395 2025 | Assessor Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3413, #7 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $11,268 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3415, #8 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $810,000 Apr 2019 | $10,741 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3416, #50 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 · 13.8 acres | $572,000 Dec 2020 | $8,496 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3417, #9 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $1,195,000 May 2021 | $11,735 2025 | Assessor + 2 Documents Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3418, #49 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $550,000 Jan 2005 | $5,689 2025 | Assessor Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3419, #10 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $950,000 May 2019 | $7,555 2025 | Assessor + 3 Documents Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3421, #11 Winding Oaks Dr |
3 bd · 3 ba · 2,608 sqft built 1988 | $625,000 Apr 2012 | $12,670 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3423, #12 Winding Oaks Dr |
3 bd · 2.5 ba · 2,555 sqft built 1988 · 13.8 acres | $709,000 Sep 2013 | $9,810 2024 | Assessor Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3425, #13 Winding Oaks Dr |
2 bd · 2 ba · 2,039 sqft built 1988 | $500,000 Feb 2019 | $8,199 2025 | Assessor + 1 Document Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3427, #14 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 · 13.8 acres | $1,100,000 Jun 2026 | $13,849 2025 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3428, #48 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $8,095 2025 | Assessor + 1 Document Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3429, #15 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 · 13.8 acres | $825,000 Apr 2015 | $9,268 2024 | Assessor + 2 Documents Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3430, #47 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $415,000 Aug 2009 | $6,586 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3431, #16 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $875,000 Feb 2020 | $10,035 2025 | Assessor + 2 Documents Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3432, #46 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | — Jul 1998 | $5,386 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3433, #17 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $615,000 Apr 2008 | $13,088 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3434, #45 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $558,000 Apr 2015 | $9,569 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3435, #18 Winding Oaks Dr |
2 bd · 3.5 ba · 2,555 sqft built 1988 · 13.8 acres | $850,000 Sep 2026 | $8,564 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3436, #44 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $569,000 Oct 2020 | $8,250 2025 | Assessor + 2 Documents Updated Jan 2026 | 3 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3437, #19 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 · 13.8 acres | $1,300,000 Nov 2023 | $14,133 2024 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3438, #43 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $710,000 Feb 2021 | $7,114 2025 | Assessor + 2 Documents Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3439, #20 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 · 13.8 acres | $630,000 Mar 2010 | $9,039 2025 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3441, #21 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $740,000 Feb 2018 | $7,825 2025 | Assessor + 1 Document Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3443, #22 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $800,000 Mar 2023 | $9,422 2025 | Assessor + 1 Document Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3444, #42 Winding Oaks Dr |
3 bd · 2 ba · 2,112 sqft built 1988 | $1,162,500 May 2023 | $4,977 2025 | Assessor + 4 Documents Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3445, #23 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 · 13.8 acres | $1,525,000 Jan 2022 | $14,229 2024 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3446, #41 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $725,000 May 2006 | $5,777 2025 | Assessor Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3447, #24 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $920,000 Jun 2006 | $10,934 2025 | Assessor Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3449, #25 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $855,000 Mar 2021 | $8,464 2025 | Assessor + 3 Documents Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3451, #26 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $805,000 Mar 2021 | $9,293 2025 | Assessor + 1 Document Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3453, #27 Winding Oaks Dr |
3 bd · 3 ba · 2,608 sqft built 1988 · 13.8 acres | $1,050,000 Jan 2025 | $11,429 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3455, #28 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $960,000 Feb 2025 | $9,787 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3456, #40 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | — Mar 2012 | $5,011 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3457, #29 Winding Oaks Dr |
2 bd · 3 ba · 2,608 sqft built 1988 | $633,250 Dec 2010 | $8,826 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3458, #39 Winding Oaks Dr |
3 bd · 3 ba · 2,608 sqft built 1988 | $835,000 Aug 2018 | $10,611 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3459, #30 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $420,000 Feb 2000 | $5,469 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3460, #38 Winding Oaks Dr |
3 bd · 3.5 ba · 2,608 sqft built 1988 · 13.8 acres | $1,135,000 Sep 2026 | $10,319 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3461, #31 Winding Oaks Dr |
3 bd · 3 ba · 2,608 sqft built 1988 · 13.8 acres | $10,700 2024 | Assessor Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3462, #37 Winding Oaks Dr |
3 bd · 3 ba · 2,608 sqft built 1988 | $689,000 Sep 2010 | $6,966 2025 | Assessor + 1 Document Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3463, #32 Winding Oaks Dr |
3 bd · 3 ba · 2,555 sqft built 1988 | $845,800 Nov 2020 | $11,962 2025 | Assessor + 1 Document Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3464, #36 Winding Oaks Dr |
3 bd · 3 ba · 2,608 sqft built 1988 | $638,330 Aug 2009 | $8,277 2025 | Assessor + 2 Documents Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3465, #33 Winding Oaks Dr |
2 bd · 3 ba · 2,608 sqft built 1988 | $900,000 Nov 2025 | $10,036 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3466, #35 Winding Oaks Dr |
2 bd · 2 ba · 2,039 sqft built 1988 · 13.8 acres | $758,500 Jun 2026 | $4,918 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3467, #34 Winding Oaks Dr |
2 bd · 2 ba · 2,112 sqft built 1988 | $1,000,000 Apr 2022 | $9,752 2025 | Assessor + 2 Documents Updated Jan 2026 | 3 Owners on File Owner Occupied |