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Thomas Square Dr, Winter Garden, FL Property Records

Orange County property records for 33 addresses on Thomas Square Dr, Winter Garden, FL · Last verified August 2026

Thomas Square Dr Highlights

Properties 33
Median Sale Price $578,000
Deeds and Mortgages on File 65
Median Price per Sqft $253
Owner Occupied 85%
Median Annual Tax Bill $8,355
Median Year Built 2016
Median Ownership Tenure 8 years

Properties on Thomas Square Dr

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

5501 Thomas Square Dr

4 bd · 2.5 ba · 2,937 sqft · 0.296 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$433,700Dec 2015 $6,0662025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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5507 Thomas Square Dr

4 bd · 3.5 ba · 3,761 sqft · 0.221 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$553,638Sep 2015 $8,7692025 2 Names on Record Owner Occupied AssessorUpdated May 2026

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5513 Thomas Square Dr

4 bd · 3.5 ba · 3,690 sqft · 0.225 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$620,000Sep 2019 $7,9272025 Amount on Record Feb 2016 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

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5518 Thomas Square Dr

4 bd · 3.5 ba · 2,538 sqft · 0.21 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$585,000Jan 2026 $9,4892025 Amount on Record Nov 2022 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

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5519 Thomas Square Dr

4 bd · 3 ba · 2,762 sqft · 0.22 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$399,900Apr 2016 $6,8312025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

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5524 Thomas Square Dr

4 bd · 3 ba · 2,288 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$590,000Mar 2024 $8,0862025 Amount on Record May 2016 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated May 2026

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5525 Thomas Square Dr

4 bd · 2.5 ba · 2,867 sqft · 0.228 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$825,000May 2024 $12,9632025 Amount on Record Aug 2019 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

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5530 Thomas Square Dr

4 bd · 3.5 ba · 2,195 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$371,328Sep 2015 $8,7672025 2 Names on Record Assessor + 1 DocumentUpdated May 2026

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5536 Thomas Square Dr

3 bd · 2 ba · 2,231 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$420,000Jul 2020 $5,9772025 Amount on Record Oct 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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5542 Thomas Square Dr

4 bd · 3.5 ba · 2,680 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100May 2022 $5,8892025 Amount on Record Jan 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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5548 Thomas Square Dr

2 bd · 2.5 ba · 2,139 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$580,000Jan 2025 $8,6622025 Amount on Record May 2021 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

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5554 Thomas Square Dr

3 bd · 3 ba · 2,093 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$545,000Jan 2022 $5,9402025 Amount on Record Nov 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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5560 Thomas Square Dr

4 bd · 2.5 ba · 2,267 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$292,000Dec 2015 $5,3232025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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5566 Thomas Square Dr

3 bd · 3.5 ba · 2,191 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$335,340Oct 2015 $5,4012025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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5572 Thomas Square Dr

4 bd · 4.5 ba · 2,347 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$450,000Dec 2019 $6,2932025 Amount on Record Jan 2016 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

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5578 Thomas Square Dr

4 bd · 3 ba · 2,891 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$490,000Sep 2020 $9,8652025 Amount on Record Apr 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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5584 Thomas Square Dr

4 bd · 2.5 ba · 2,148 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$347,685Mar 2016 $5,3362025 Amount on Record Feb 2016 1 Name on Record Owner Occupied AssessorUpdated May 2026

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5590 Thomas Square Dr

4 bd · 4.5 ba · 2,475 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$356,270Oct 2015 $9,2182025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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5596 Thomas Square Dr

4 bd · 3.5 ba · 2,284 sqft · 0.173 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$578,000Jun 2026 $8,5682025 Amount on Record Dec 2015 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

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5602 Thomas Square Dr

4 bd · 3.5 ba · 2,284 sqft · 0.157 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$385,040Mar 2017 $8,9002025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

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5608 Thomas Square Dr

3 bd · 2.5 ba · 1,840 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$570,000Jul 2023 $8,3552025 Amount on Record Aug 2018 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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5614 Thomas Square Dr

3 bd · 3.5 ba · 1,984 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$396,075Nov 2017 $8,2302025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

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5620 Thomas Square Dr

4 bd · 2.5 ba · 2,292 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$365,625Aug 2017 $5,5652025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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5626 Thomas Square Dr

4 bd · 4 ba · 2,452 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$372,295Feb 2018 $6,0762025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

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5632 Thomas Square Dr

2 bd · 2.5 ba · 2,195 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$368,720Jun 2017 $5,5722025 Amount on Record May 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

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5638 Thomas Square Dr

4 bd · 2.5 ba · 2,292 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$360,900Aug 2017 $8,5572025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

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5644 Thomas Square Dr

4 bd · 4.5 ba · 2,457 sqft · 0.18 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$535,000Oct 2021 $6222025 Amount on Record Aug 2021 2 Names on Record Owner Occupied Assessor + 6 DocumentsUpdated May 2026

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5719 Thomas Square Dr

5 bd · 4.5 ba · 4,104 sqft · 0.227 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$516,408Apr 2018 $9,8602025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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5725 Thomas Square Dr

4 bd · 3.5 ba · 3,731 sqft · 0.188 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$512,815Nov 2017 $8,6112025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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5731 Thomas Square Dr

4 bd · 3.5 ba · 4,024 sqft · 0.186 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$513,315Apr 2018 $9,1362025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

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5737 Thomas Square Dr

5 bd · 4.5 ba · 3,731 sqft · 0.184 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$8,7152025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

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5743 Thomas Square Dr

4 bd · 2.5 ba · 2,917 sqft · 0.183 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$740,000Dec 2022 $10,7302025 Amount on Record Aug 2020 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

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5749 Thomas Square Dr

4 bd · 3.5 ba · 3,731 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$464,105Oct 2017 $12,1212025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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Wildfire Risk on Thomas Square 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 36th percentile of exposed land nationally · 10th in Florida
Wildfire LikelihoodLow — about 1 in 3,191 per year
ExposureDirect
1 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets