Winona Dr, Saint Cloud, FL Property Records

Osceola County property records for 70 addresses on Winona Dr, Saint Cloud, FL · Last verified August 2026

Winona Dr Highlights

Properties 70
Median Sale Price $412,490
Deeds and Mortgages on File 87
Median Price per Sqft $211
Owner Occupied 90%
Median Annual Tax Bill $5,210
Median Year Built 2022
Median Ownership Tenure 4 years

Properties on Winona Dr

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

5500 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$365,990Oct 2021 $7122025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5501 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$411,990Mar 2023 $5,1412025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5504 Winona Dr

5 bd · 3 ba · 2,674 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$392,990Sep 2021 $5,8002025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5505 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$460,990Jun 2023 $5,9032025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5508 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$353,990Oct 2021 $5,0922025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5509 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$411,990Mar 2023 $5,1552025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5512 Winona Dr

5 bd · 3 ba · 2,674 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$395,990Dec 2021 $6,2302025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5513 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$410,000Mar 2023 $5,8402024 Amount on Record Aug 2022 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

5516 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$350,000Sep 2021 $4,8492025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5517 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$355,000Dec 2021 $5,4452025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Dec 2025

5520 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$328,990Aug 2021 $4,6112025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5521 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$315,990Apr 2021 $4,8002025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5524 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$336,990Aug 2021 $5,7112025 2 Names on Record Assessor + 1 DocumentUpdated Dec 2025

5525 Winona Dr

5 bd · 4 ba · 2,884 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$376,000Jun 2021 $5,9282025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5528 Winona Dr

5 bd · 3 ba · 2,674 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$399,990Sep 2021 $7122025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5529 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2022 $4,4982025 Amount on Record Apr 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5532 Winona Dr

5 bd · 4 ba · 2,884 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,438,600Jun 2025 $6,9502025 Amount on Record Oct 2021 1 Name on Record Assessor + 2 DocumentsUpdated Dec 2025

5533 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$320,990Mar 2021 $5,0922025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5536 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$385,000Dec 2023 $4,9322025 Amount on Record Jul 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5537 Winona Dr

5 bd · 3 ba · 2,674 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$365,000May 2021 $5,8262025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5540 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$337,990Aug 2021 $4,8122025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5541 Winona Dr

5 bd · 4 ba · 2,884 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$362,990May 2021 $5,3202025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5544 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$326,990Aug 2021 $5,4982025 2 Names on Record Assessor + 1 DocumentUpdated Dec 2025

5545 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$317,990Mar 2021 $4,7672025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5548 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$333,000Jul 2021 $4,8122025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5549 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$305,990May 2021 $4,5662025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5552 Winona Dr

5 bd · 4 ba · 2,884 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$379,990Sep 2021 $6,0022025 3 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5553 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$390,000Apr 2023 $4,5592025 Amount on Record May 2021 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5556 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$324,990Jun 2021 $4,6112025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5557 Winona Dr

5 bd · 4 ba · 2,884 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$365,990Jun 2021 $5,8932025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5560 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$343,990Jul 2021 $4,8122025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5561 Winona Dr

5 bd · 3 ba · 2,674 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$352,990Jul 2021 $5,8202025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5565 Winona Dr

5 bd · 4 ba · 2,884 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$364,990Jul 2021 $6,3532025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5569 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$327,990May 2021 $5,0922025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5577 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.18 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$451,990Aug 2022 $4,9602025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5581 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$412,490Jul 2022 $5,3792025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5585 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$475,000Sep 2022 $6,6482025 2 Names on Record Assessor + 1 DocumentUpdated Dec 2025

5589 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$407,000Feb 2025 $5,2042024 —Jan 2025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

5593 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$417,990Aug 2022 $5,1162025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5597 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$401,990Aug 2022 $4,1592025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5601 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$430,990Sep 2022 $5,1162025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5605 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$425,990Aug 2022 $5,7262025 2 Names on Record Assessor + 1 DocumentUpdated Dec 2025

5609 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$480,990Dec 2022 $6,0952025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5610 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$436,540Dec 2022 $5,1682025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

5613 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$429,990Aug 2022 $8,8412025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5614 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$414,440Feb 2023 $5,1932025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

5617 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$425,990Aug 2022 $5,1162025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5618 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$467,990Apr 2023 $6,7292025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5621 Winona Dr

3 bd · 2 ba · 1,676 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$412,990Aug 2022 $5,4692025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5622 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$462,990Jan 2023 $5,7892025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5625 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$435,990Sep 2022 $2,9212025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5626 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$407,540Mar 2023 $5,1932025 3 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5629 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$449,900Sep 2023 $5,2532024 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

5630 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$464,990Jun 2023 $6,1632025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5633 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$435,990Aug 2022 $5,1562025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5634 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$430,540Dec 2022 $5,7762025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

5637 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$480,990Dec 2022 $6,0812025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5638 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$423,540Jan 2023 $5,2532025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5641 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$448,990Aug 2022 $5,1162025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5642 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$461,990Jun 2023 $6,0592025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5645 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$437,990Sep 2022 $5,1162025 3 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5646 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$458,000Nov 2022 $5,2102025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5649 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$466,990Dec 2022 $6,1232025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5650 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$450,490Sep 2022 $5,7352025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5653 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$444,990Sep 2022 $5,6822025 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

5654 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$443,490Oct 2022 $6312024 1 Name on Record AssessorUpdated Aug 2026

5658 Winona Dr

5 bd · 3 ba · 2,626 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$486,990Dec 2022 $6,0812025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5662 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$453,490Oct 2022 $5,2042024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

5667 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$436,000Jun 2022 $5,0762025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

5668 Winona Dr

4 bd · 2 ba · 1,846 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$444,990Aug 2023 $5,2202025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

Wildfire Risk on Winona Dr

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

Wildfire RiskHigh
this street's cells rank at the 82nd percentile of exposed land nationally · 72nd in Florida
Wildfire LikelihoodHigh — about 1 in 118 per year
ExposureDirect
3 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets