Pinellas County property records for 44 addresses on Chesterfield Dr, Clearwater, FL · Last verified October 2026
| Properties | 44 |
|---|---|
| Median Sale Price | $395,000 |
| Deeds and Mortgages on File | 71 |
| Median Price per Sqft | $304 |
| Owner Occupied | 82% |
| Median Annual Tax Bill | $2,040 |
| Median Year Built | 1961 |
| Median Ownership Tenure | 10 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1300 Chesterfield Dr |
5 bd · 3 ba · 3,064 sqft built 1971 · 0.251 acres | $386,000 Apr 2020 | $10,391 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1301 Chesterfield Dr |
2 ba · 2,048 sqft built 1962 · 0.23 acres | $145,000 May 2009 | $1,807 2025 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1307 Chesterfield Dr |
2 ba · 1,310 sqft built 1959 · 0.189 acres | $82,000 Nov 1998 | $768 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1311 Chesterfield Dr |
2 bd · 1 ba · 1,044 sqft built 1957 · 0.201 acres | $329,000 May 2025 | $2,972 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1316 Chesterfield Dr |
1 ba · 950 sqft built 1958 · 0.189 acres | $179,000 Feb 2006 | $1,141 2025 | Assessor + 1 Document Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1317 Chesterfield Dr |
3 bd · 1 ba · 1,355 sqft built 1957 · 0.201 acres | $232,500 Dec 2020 | $6,926 2025 | Assessor + 5 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1320 Chesterfield Dr |
3 bd · 2 ba · 1,706 sqft built 1958 · 0.188 acres | $187,500 Jun 2016 | $3,305 2025 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1321 Chesterfield Dr |
3 bd · 2 ba · 1,363 sqft built 1957 · 0.201 acres | $430,000 Aug 2022 | $6,772 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1324 Chesterfield Dr |
3 bd · 2 ba · 1,473 sqft built 1961 · 0.188 acres | $449,000 May 2026 | $1,069 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1325 Chesterfield Dr |
3 bd · 2 ba · 1,168 sqft built 1958 · 0.201 acres | $395,000 Apr 2024 | $4,801 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1328 Chesterfield Dr |
3 bd · 2 ba · 1,403 sqft built 1962 · 0.188 acres | $441,800 Dec 2021 | $7,432 2025 | Assessor + 3 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1329 Chesterfield Dr |
4 bd · 2 ba · 1,170 sqft built 1958 · 0.201 acres | $180,000 Jun 2014 | $2,558 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1332 Chesterfield Dr |
2 ba · 1,052 sqft built 1984 · 0.176 acres | $68,000 May 1989 | $1,355 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1333 Chesterfield Dr |
2 bd · 2 ba · 1,297 sqft built 1966 · 0.189 acres | $495,000 Feb 2022 | $5,475 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1336 Chesterfield Dr |
1.5 ba · 1,226 sqft built 1959 · 0.179 acres | — Mar 2003 | $767 2024 | Assessor + 2 Documents Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1337 Chesterfield Dr |
4 bd · 2 ba · 1,857 sqft built 1957 · 0.189 acres | $146,000 Jul 2013 | $1,309 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1341 Chesterfield Dr |
3 bd · 2 ba · 1,568 sqft built 1966 · 0.22 acres | $448,000 Sep 2023 | $6,773 2025 | Assessor + 6 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1344 Chesterfield Dr |
3 bd · 2 ba · 1,726 sqft built 1961 · 0.196 acres | $251,000 Sep 2018 | $3,784 2025 | Assessor + 4 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1348 Chesterfield Dr |
3 bd · 2 ba · 1,422 sqft built 1961 · 0.203 acres | $455,500 May 2025 | $1,316 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1350 Chesterfield Dr |
2 ba · 1,182 sqft built 1959 · 0.177 acres | $185,000 Jul 2017 | $2,685 2024 | Assessor + 3 Documents Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1351 Chesterfield Dr |
2 ba · 1,139 sqft built 1972 · 0.187 acres | $63,000 Jun 1986 | $1,074 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1354 Chesterfield Dr |
4 bd · 2 ba · 1,347 sqft built 1959 · 0.181 acres | $487,000 Aug 2024 | $7,995 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1355 Chesterfield Dr |
3 bd · 2 ba · 1,324 sqft built 1959 · 0.17 acres | $186,000 Oct 2016 | $2,820 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1358 Chesterfield Dr |
1.5 ba · 1,764 sqft built 1960 · 0.181 acres | $175,000 Apr 2018 | $2,623 2024 | Assessor + 1 Document Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1359 Chesterfield Dr |
2 ba · 1,164 sqft built 1972 · 0.165 acres | $1,208 2025 | Assessor Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1362 Chesterfield Dr |
3 bd · 1.5 ba · 1,208 sqft built 1971 · 0.181 acres | $95,000 Dec 2014 | $3,569 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1363 Chesterfield Dr |
1 ba · 1,330 sqft built 1957 · 0.217 acres | — Sep 2016 | $3,957 2024 | Assessor + 3 Documents Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1366 Chesterfield Dr |
3 ba · 1,838 sqft built 1972 · 0.181 acres | — Dec 1992 | $1,652 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1367 Chesterfield Dr |
2 ba · 1,138 sqft built 1969 · 0.325 acres | $114,900 Oct 2024 | $6,403 2024 | Assessor Updated Apr 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1368 Chesterfield Dr |
1.5 ba · 1,148 sqft built 1963 · 0.171 acres | $325,000 Jun 2026 | $4,724 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1369 Chesterfield Dr |
2 ba · 1,198 sqft built 1962 · 0.293 acres | $71,700 Dec 1988 | $1,043 2025 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1370 Chesterfield Dr |
2 ba · 1,073 sqft built 1963 · 0.162 acres | $28,000 Nov 1975 | $502 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1373 Chesterfield Dr |
2 ba · 1,336 sqft built 1966 · 0.235 acres | $190,000 Jun 2005 | $916 2024 | Assessor Updated Apr 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1374 Chesterfield Dr |
2 ba · 1,388 sqft built 1958 · 0.178 acres | $70,600 Jun 2004 | $680 2024 | Assessor + 3 Documents Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1377 Chesterfield Dr |
1 ba · 1,024 sqft built 1962 · 0.192 acres | $62,000 Nov 1989 | $817 2025 | Assessor Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1378 Chesterfield Dr |
2 ba · 1,438 sqft built 1960 · 0.18 acres | $70,000 Dec 1992 | $882 2025 | Assessor Updated Jan 2026 | 3 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1381 Chesterfield Dr |
2 ba · 1,972 sqft built 1980 · 0.188 acres | $317,000 Nov 2020 | $2,038 2024 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1382 Chesterfield Dr |
1.5 ba · 1,067 sqft built 1958 · 0.18 acres | $135,000 Sep 2003 | Assessor + 3 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1385 Chesterfield Dr |
2 ba · 1,104 sqft built 1959 · 0.193 acres | $174,900 Oct 2004 | $823 2024 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1388 Chesterfield Dr |
2 ba · 1,146 sqft built 1970 · 0.216 acres | — Feb 2024 | $1,330 2025 | Assessor + 2 Documents Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1389 Chesterfield Dr |
3 bd · 2 ba · 1,414 sqft built 1962 · 0.19 acres | $3,990 Jun 2026 | $7,054 2025 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1391 Chesterfield Dr |
2 ba · 1,457 sqft built 1971 · 0.19 acres | $100,571 Sep 2000 | $2,040 2025 | Assessor Updated Jan 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1393 Chesterfield Dr |
3 bd · 2 ba · 1,538 sqft built 1971 · 0.189 acres | $182,500 Nov 2015 | $2,974 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1395 Chesterfield Dr |
2 ba · 1,458 sqft built 1960 · 0.227 acres | — Jan 2025 | $1,007 2025 | Assessor Updated Jan 2026 | 3 Owners on File Owner Occupied |