Sarasota County property records for 49 addresses on Jessie Harbor Dr, Osprey, FL · Last verified October 2026
| Properties | 87 |
|---|---|
| Median Sale Price | $570,000 |
| Deeds and Mortgages on File | 115 |
| Median Price per Sqft | $269 |
| Owner Occupied | 59% |
| Median Annual Tax Bill | $4,448 |
| Median Year Built | 2004 |
| Median Ownership Tenure | 7 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1101 Jessie Harbor Dr |
2 bd · 2 ba · 1,425 sqft built 2004 | $389,000 Sep 2004 | $4,170 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1102, #1102 Jessie Harbor Dr |
2 bd · 2 ba · 1,425 sqft built 2004 · 0.729 acres | $435,000 Feb 2026 | $2,137 2024 | Assessor + 3 Documents Updated Aug 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1201 Jessie Harbor Dr |
3 bd · 3 ba · 2,006 sqft built 2004 | $560,000 Sep 2025 | $6,381 2025 | Assessor + 3 Documents Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1202, #1204 Jessie Harbor Dr |
3 bd · 2.5 ba · 2,006 sqft built 2004 · 0.729 acres | $570,000 Aug 2026 | $6,502 2025 | Assessor + 5 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2251, #2101 Jessie Harbor Dr |
2 bd · 2 ba · 1,400 sqft built 2006 | $310,000 Aug 2026 | $4,919 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2255, #2201 Jessie Harbor Dr |
3 bd · 3 ba · 2,006 sqft built 2006 | $380,000 Mar 2017 | $3,493 2025 | Assessor + 3 Documents Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2259, #2202 Jessie Harbor Dr |
3 bd · 2.5 ba · 2,006 sqft built 2006 | $450,000 Mar 2021 | $5,245 2024 | Assessor + 1 Document Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2263, #2102 Jessie Harbor Dr |
2 bd · 2 ba · 1,391 sqft built 2006 | $290,000 Jun 2016 | $4,104 2025 | Assessor Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2267, #2103 Jessie Harbor Dr |
2 bd · 2 ba · 1,391 sqft built 2006 | $445,000 Nov 2024 | $4,104 2025 | Assessor Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2271, #2203 Jessie Harbor Dr |
3 bd · 3 ba · 2,006 sqft built 2006 | $570,000 May 2023 | $4,808 2025 | Assessor + 1 Document Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2275, #2204 Jessie Harbor Dr |
3 bd · 3 ba · 2,006 sqft built 2006 | $550,000 Sep 2006 | $2,351 2025 | Assessor + 1 Document Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2279, #2104 Jessie Harbor Dr |
2 bd · 2 ba · 1,400 sqft built 2006 | $195,000 Mar 2010 | $4,219 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2301 Jessie Harbor Dr |
2 bd · 2 ba · 1,400 sqft built 2006 | $300,000 Jun 2018 | $2,555 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2305, #2401 Jessie Harbor Dr |
3 bd · 3 ba · 2,006 sqft built 2006 | $525,000 Aug 2021 | $5,431 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2309, #2402 Jessie Harbor Dr |
3 bd · 2.5 ba · 2,006 sqft built 2006 | $449,000 Mar 2006 | $6,227 2025 | Assessor Updated Jul 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2313, #2302 Jessie Harbor Dr |
2 bd · 2 ba · 1,391 sqft built 2006 | $320,000 Sep 2025 | $1,489 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2317, #2303 Jessie Harbor Dr |
2 bd · 2 ba · 1,391 sqft built 2006 | $275,000 Jul 2008 | $1,489 2025 | Assessor Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2321, #2403 Jessie Harbor Dr |
3 bd · 3 ba · 2,006 sqft built 2006 | $478,000 Apr 2021 | $5,488 2025 | Assessor + 3 Documents Updated Jan 2026 | 3 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2325, #2404 Jessie Harbor Dr |
3 bd · 3 ba · 2,006 sqft built 2006 | $230,000 Mar 2009 | $5,696 2025 | Assessor Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
2329, #2304 Jessie Harbor Dr |
2 bd · 2 ba · 1,400 sqft built 2006 | $235,000 Mar 2009 | $2,497 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3101 Jessie Harbor Dr |
2 bd · 2 ba · 1,425 sqft built 1996 | $150,000 Jun 2010 | $3,994 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3102 Jessie Harbor Dr |
2 bd · 2 ba · 1,425 sqft built 1996 | $175,000 May 2010 | $4,183 2025 | Assessor + 1 Document Updated Jan 2026 | 3 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3103 Jessie Harbor Dr |
2 bd · 2 ba · 1,425 sqft built 1996 | $165,000 Feb 2011 | $1,731 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3104 Jessie Harbor Dr |
2 bd · 2 ba · 1,425 sqft built 1996 | $331,500 Nov 2003 | $1,941 2025 | Assessor + 1 Document Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3201, #3201 Jessie Harbor Dr |
3 bd · 2.5 ba · 1,945 sqft built 1996 · 0.43 acres | $399,000 May 2017 | $6,574 2024 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3202 Jessie Harbor Dr |
3 bd · 2.5 ba · 1,907 sqft built 1996 · 0.43 acres | $340,000 Nov 2015 | $3,262 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3203 Jessie Harbor Dr |
3 bd · 2.5 ba · 1,907 sqft built 1996 · 0.43 acres | $125,000 Jul 2014 | $2,510 2024 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3204 Jessie Harbor Dr |
3 bd · 3 ba · 1,945 sqft built 1996 | $305,000 Apr 2019 | $5,349 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4101 Jessie Harbor Dr |
2 bd · 2 ba · 1,425 sqft built 1992 | $480,000 Aug 2022 | $4,035 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4102 Jessie Harbor Dr |
2 bd · 2 ba · 1,425 sqft built 1992 | $240,000 Jul 2020 | $4,251 2025 | Assessor + 2 Documents Updated Jan 2026 | 3 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4201 Jessie Harbor Dr |
3 bd · 3 ba · 1,945 sqft built 1992 | $400,000 Oct 2004 | $4,589 2025 | Assessor Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4202 Jessie Harbor Dr |
3 bd · 3 ba · 1,945 sqft built 1992 | $300,000 Aug 2019 | $2,462 2025 | Assessor + 2 Documents Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5100 Jessie Harbor Dr |
0.973 acres | $800 Oct 2000 | Assessor Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5100 Jessie Harbor Dr |
25 units · 2,143 sq ft Built 2004 | $640,000 Jan 2026 | $5,436 2025 |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
6100 Jessie Harbor Dr |
15 units · 2,630 sq ft Built 2005 | $830,000 Jun 2026 | $6,404 2025 |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7101 Jessie Harbor Dr |
3 bd · 2 ba · 1,692 sqft built 1985 | $265,000 Jul 2017 | $3,965 2025 | Assessor + 3 Documents Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7102 Jessie Harbor Dr |
2 bd · 2 ba · 1,255 sqft built 1985 | — Jun 2025 | $2,435 2025 | Assessor Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7103 Jessie Harbor Dr |
2 bd · 2 ba · 1,255 sqft built 1985 | $407,000 May 2022 | $1,940 2025 | Assessor + 2 Documents Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7104 Jessie Harbor Dr |
2 bd · 2 ba · 1,255 sqft built 1985 · 0.333 acres | $255,000 Jan 2021 | $3,295 2024 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7105 Jessie Harbor Dr |
3 bd · 2 ba · 1,692 sqft built 1985 | $235,000 Sep 2018 | $3,860 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7201 Jessie Harbor Dr |
3 bd · 2 ba · 1,692 sqft built 1985 | $604,000 May 2022 | $4,856 2025 | Assessor + 4 Documents Updated Jan 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7202 Jessie Harbor Dr |
2 bd · 2 ba · 1,255 sqft built 1985 | $242,500 Aug 2016 | $1,655 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7203 Jessie Harbor Dr |
2 bd · 3 ba · 1,255 sqft built 1985 | $330,000 Jan 2006 | $2,444 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7204 Jessie Harbor Dr |
2 bd · 2 ba · 1,255 sqft built 1985 | $305,000 May 2006 | $3,281 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7205 Jessie Harbor Dr |
3 bd · 2 ba · 1,692 sqft built 1985 | $241,000 May 2020 | $3,711 2024 | Assessor + 3 Documents Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7301 Jessie Harbor Dr |
3 bd · 2 ba · 1,692 sqft built 1985 | $150,000 Aug 2003 | $3,586 2025 | Assessor Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7302 Jessie Harbor Dr |
3 bd · 2 ba · 1,883 sqft built 1985 | $255,000 Jun 2021 | $3,487 2025 | Assessor + 3 Documents Updated Jan 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7303 Jessie Harbor Dr |
3 bd · 2 ba · 1,883 sqft built 1985 | $475,000 Jul 2022 | $5,116 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7304 Jessie Harbor Dr |
3 bd · 2 ba · 1,692 sqft built 1985 | $254,000 Apr 2016 | $3,851 2024 | Assessor + 1 Document Updated Aug 2026 | Owner on File |