Sterling Dr, Winter Haven, FL Property Records

Polk County property records for 69 addresses on Sterling Dr, Winter Haven, FL · Last verified August 2026

Sterling Dr Highlights

Properties 69
Median Sale Price $285,000
Deeds and Mortgages on File 110
Median Price per Sqft $154
Owner Occupied 91%
Median Annual Tax Bill $1,385
Median Year Built 1996
Median Ownership Tenure 9 years

Properties on Sterling Dr

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

302 Sterling Dr

3 bd · 2 ba · 2,460 sqft · 0.74 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$202,500Jan 2014 $1,9572025 Amount on Record Jan 1999 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

304 Sterling Dr

3 bd · 2 ba · 1,560 sqft · 0.348 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$285,000Jun 2023 $2,6772025 —Jul 2020 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

306 Sterling Dr

3 bd · 2 ba · 1,972 sqft · 0.403 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$375,000Aug 2024 $3,3932025 Amount on Record Apr 2024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

307 Sterling Dr

3 bd · 2 ba · 1,444 sqft · 0.182 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$335,000Jan 2024 $2,5372025 Amount on Record Mar 2023 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

308 Sterling Dr

3 bd · 3 ba · 1,840 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$298,000Aug 2023 $2,6632025 Amount on Record Dec 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

310 Sterling Dr

3 bd · 2 ba · 1,788 sqft · 0.305 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$114,000Oct 2011 $1,1242025 Amount on Record Nov 1999 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

312 Sterling Dr

4 bd · 2 ba · 2,072 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$320,000Mar 2022 $3,2222025 Amount on Record Jan 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

313 Sterling Dr

3 bd · 2 ba · 2,067 sqft · 0.224 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$185,000Jun 2008 $1,2442025 Amount on Record Jun 2006 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

314 Sterling Dr

3 bd · 2 ba · 1,617 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$13,800Dec 1993 $7812025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

316 Sterling Dr

3 bd · 2 ba · 2,129 sqft · 0.196 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$212,700Mar 2018 $2,4742025 Amount on Record Dec 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

318 Sterling Dr

3 bd · 2 ba · 1,953 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$165,000Mar 2004 $7002024 Amount on Record Oct 2001 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

320 Sterling Dr

3 bd · 2 ba · 2,274 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$105,000Sep 1991 $1,4302025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

322 Sterling Dr

3 bd · 2 ba · 1,560 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$101,800May 2020 $2,7272025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

324 Sterling Dr

4 bd · 2 ba · 2,281 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$349,900Aug 2022 $7002024 Amount on Record May 2006 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

326 Sterling Dr

4 bd · 2 ba · 2,168 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$135,000Jan 2009 $1,3852025 —Jul 2008 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

328 Sterling Dr

3 bd · 2 ba · 1,560 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$335,000Aug 2023 $3,2432025 Amount on Record Oct 1999 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

330 Sterling Dr

3 bd · 2 ba · 1,426 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$279,900Feb 2023 $3,0492025 Amount on Record Aug 2017 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

333 Sterling Dr

3 bd · 2 ba · 1,594 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$97,000Oct 2012 $9152025 Amount on Record Jun 2012 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

334 Sterling Dr

5 bd · 3 ba · 2,430 sqft · 0.224 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6632025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

335 Sterling Dr

3 bd · 2 ba · 1,746 sqft · 0.172 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$205,000Nov 2018 $1,7482025 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

336 Sterling Dr

2 bd · 2 ba · 1,488 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$199,900Apr 2006 $7182025 Amount on Record Aug 2002 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

337 Sterling Dr

3 bd · 2 ba · 1,410 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$144,900Jul 2014 $7002024 Amount on Record Apr 1998 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

338 Sterling Dr

3 bd · 2 ba · 1,970 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$95,000Jun 1992 $9952025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

339 Sterling Dr

3 bd · 2 ba · 1,696 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$120,000Sep 2003 $8262025 Amount on Record Sep 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

340 Sterling Dr

4 bd · 2 ba · 2,027 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$184,500Nov 2018 $1,8282025 Amount on Record Jan 2000 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

341 Sterling Dr

3 bd · 2 ba · 1,837 sqft · 0.172 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$380,000Apr 2026 $3,5862025 Amount on Record Sep 2025 2 Names on Record Assessor + 3 DocumentsUpdated Jul 2026

342 Sterling Dr

4 bd · 2 ba · 1,929 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$150,000Oct 2015 $1,1302025 Amount on Record Jan 2004 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

343 Sterling Dr

3 bd · 2 ba · 1,372 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$259,900Jul 2026 $7362025 Amount on Record Mar 2006 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

344 Sterling Dr

3 bd · 2 ba · 2,062 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$65,000Dec 2024 $2,9142025 Amount on Record May 2003 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

345 Sterling Dr

3 bd · 2 ba · 2,460 sqft · 0.248 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$279,500Dec 2020 $2,8102025 Amount on Record Feb 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

346 Sterling Dr

3 bd · 2 ba · 1,929 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$345,000Apr 2025 $2,1662025 Amount on Record Sep 2020 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

348 Sterling Dr

3 bd · 2 ba · 1,556 sqft · 0.255 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$163,000Sep 2017 $1,4642025 Amount on Record Nov 2009 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

350 Sterling Dr

3 bd · 2 ba · 1,639 sqft · 0.248 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$243,000Aug 2020 $2,9092025 Amount on Record Jan 2011 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

352 Sterling Dr

3 bd · 2 ba · 1,492 sqft · 0.188 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$166,500Nov 2004 $1,0012025 Amount on Record Jul 2004 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

353 Sterling Dr

3 bd · 2 ba · 2,002 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,0362025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

354 Sterling Dr

4 bd · 2 ba · 2,027 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$123,500Jul 2002 $1,2362025 Amount on Record Dec 1998 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

355 Sterling Dr

3 bd · 2 ba · 2,489 sqft · 0.19 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$150,000Feb 2016 $2,0872025 Amount on Record Mar 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

356 Sterling Dr

3 bd · 2 ba · 1,535 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$330,000Jun 2026 $2,6552025 Amount on Record Sep 2023 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

357 Sterling Dr

3 bd · 2 ba · 1,411 sqft · 0.19 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$220,100Sep 2005 $1,0102025 Amount on Record Jun 2001 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

358 Sterling Dr

3 bd · 2 ba · 1,535 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$106,300Sep 2001 $7842025 Amount on Record Oct 2000 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

359 Sterling Dr

3 bd · 2 ba · 1,411 sqft · 0.19 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$152,000May 2005 $1,1292025 Amount on Record Jul 2004 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

360 Sterling Dr

3 bd · 2 ba · 2,062 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$172,500Nov 2007 $9302025 Amount on Record Jun 2007 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

361 Sterling Dr

3 bd · 2 ba · 1,781 sqft · 0.19 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$192,000Jun 2018 $3,8312025 Amount on Record Jul 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

362 Sterling Dr

3 bd · 2 ba · 2,062 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$222,900Jun 2020 $2,1462025 Amount on Record Nov 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

363 Sterling Dr

3 bd · 2 ba · 1,632 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$157,900Sep 2020 $7002024 —Mar 2005 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

364 Sterling Dr

4 bd · 2 ba · 2,043 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—May 2019 $1,0522025 Amount on Record Nov 2010 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

365 Sterling Dr

3 bd · 2 ba · 1,465 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$219,000Apr 2021 $2,3592025 Amount on Record Oct 2019 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

366 Sterling Dr

3 bd · 2 ba · 1,535 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$157,000Dec 2007 $7402025 Amount on Record Dec 2004 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

367 Sterling Dr

3 bd · 2 ba · 1,674 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$179,000Jun 2006 $9122025 Amount on Record Aug 2003 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

368 Sterling Dr

3 bd · 2 ba · 2,062 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$17,900May 1998 $1,0482025 —May 1998 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

369 Sterling Dr

3 bd · 2 ba · 2,002 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$48,300May 2020 $3,8772025 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

370 Sterling Dr

3 bd · 2 ba · 2,062 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$121,000Aug 2011 $1,0862025 Amount on Record Mar 2005 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

371 Sterling Dr

3 bd · 2 ba · 1,705 sqft · 0.177 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$20,000Jul 1998 $9142025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

372 Sterling Dr

3 bd · 2 ba · 1,691 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$325,000Jun 2024 $2,9282025 Amount on Record Sep 2021 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

374 Sterling Dr

3 bd · 2 ba · 2,062 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$167,000Nov 2007 $1,1692025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

376 Sterling Dr

4 bd · 2 ba · 1,929 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Jun 2024 $3,3852025 Amount on Record Oct 1999 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

378 Sterling Dr

3 bd · 2 ba · 1,781 sqft · 0.288 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2015 $7162024 —Nov 2009 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

380 Sterling Dr

3 bd · 2 ba · 1,742 sqft · 0.344 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$16,000Jul 1996 $9642025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

381 Sterling Dr

3 bd · 2 ba · 1,451 sqft · 0.18 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$100,000Jun 2017 $2,7612025 Amount on Record Mar 2013 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

382 Sterling Dr

4 bd · 2 ba · 1,621 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$121,900Dec 2001 $2,9692025 Amount on Record Sep 1999 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

383 Sterling Dr

3 bd · 2 ba · 1,442 sqft · 0.173 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$77,900Dec 1991 $1,0722025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

384 Sterling Dr

3 bd · 2 ba · 1,740 sqft · 0.209 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$360,000Sep 2024 $3,5982025 Amount on Record Oct 1995 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

385 Sterling Dr

3 bd · 3 ba · 1,951 sqft · 0.173 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2024 $9102025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

386 Sterling Dr

3 bd · 2 ba · 1,909 sqft · 0.209 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$114,900Oct 2003 $9912025 Amount on Record Jun 1994 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

387 Sterling Dr

3 bd · 2 ba · 1,631 sqft · 0.172 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$100Apr 1998 $1,1152025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

388 Sterling Dr

3 bd · 3 ba · 1,693 sqft · 0.209 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
—May 2017 $3,1132025 Amount on Record Dec 2005 1 Name on Record AssessorUpdated Jul 2026

389 Sterling Dr

3 bd · 2 ba · 1,582 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$217,500Apr 2021 $2,5082025 Amount on Record Jul 2005 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

390 Sterling Dr

3 bd · 2 ba · 2,512 sqft · 0.231 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$134,900Aug 2014 $1,8702025 Amount on Record Jan 2014 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

391 Sterling Dr

3 bd · 2 ba · 1,848 sqft · 0.187 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$240,000Mar 2021 $2,7972025 Amount on Record Dec 2020 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

Wildfire Risk on Sterling Dr

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank at the 18th percentile of exposed land nationally · 5th in Florida
Wildfire LikelihoodLow — about 1 in 5,435 per year
ExposureDirect
2 of 5 cells directly exposed · 2 adjoin burnable vegetation

Property Records in Nearby Streets