Bowman Dr, Winter Garden, FL Property Records

Orange County property records for 67 addresses on Bowman Dr, Winter Garden, FL · Last verified August 2026

Bowman Dr Highlights

Properties 67
Median Sale Price $565,000
Deeds and Mortgages on File 129
Median Price per Sqft $247
Owner Occupied 79%
Median Annual Tax Bill $8,439
Median Year Built 2016
Median Ownership Tenure 7 years

Properties on Bowman Dr

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

5311 Bowman Dr

4 bd · 3.5 ba · 3,712 sqft · 0.165 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$801,000Jul 2021 $11,8942025 Amount on Record Oct 2015 2 Names on Record Assessor + 8 DocumentsUpdated May 2026

5317 Bowman Dr

4 bd · 3 ba · 2,762 sqft · 0.165 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$840,000Jul 2023 $12,3552025 Amount on Record Apr 2016 2 Names on Record Owner Occupied AssessorUpdated May 2026

5323 Bowman Dr

4 bd · 3.5 ba · 3,690 sqft · 0.165 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$573,000May 2019 $8,9252025 Amount on Record Mar 2016 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5329 Bowman Dr

4 bd · 2.5 ba · 2,917 sqft · 0.165 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$600,000Apr 2021 $9,6152025 Amount on Record Aug 2018 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

5335 Bowman Dr

4 bd · 4 ba · 3,117 sqft · 0.245 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$427,255Oct 2015 $6,9652025 2 Names on Record Owner Occupied AssessorUpdated May 2026

5336 Bowman Dr

4 bd · 4 ba · 3,482 sqft · 0.872 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$792,312Jan 2016 $8,6722025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

5340 Bowman Dr

5 bd · 6.5 ba · 5,375 sqft · 2.73 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,050,000May 2026 $17,4762025 Amount on Record Jun 2019 1 Name on Record Owner Occupied Assessor + 7 DocumentsUpdated Jun 2026

5341 Bowman Dr

4 bd · 3.5 ba · 3,743 sqft · 0.241 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,185,000Sep 2024 $11,2982025 Amount on Record Nov 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5346 Bowman Dr

4 bd · 3 ba · 3,349 sqft · 1.65 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$710,299Mar 2018 $11,8082025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5347 Bowman Dr

3 bd · 2.5 ba · 2,867 sqft · 0.166 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$400,180Mar 2016 $6,9042025 Amount on Record Jan 2016 2 Names on Record Owner Occupied AssessorUpdated May 2026

5352 Bowman Dr

4 bd · 4 ba · 3,493 sqft · 1.46 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$920,897Jan 2018 $12,3572025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5353 Bowman Dr

4 bd · 3.5 ba · 3,743 sqft · 0.179 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$470,000Jun 2016 $8,5772025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5358 Bowman Dr

4 bd · 4 ba · 3,390 sqft · 2.66 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$784,100Jul 2017 $21,5982025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5359 Bowman Dr

4 bd · 3.5 ba · 2,773 sqft · 0.179 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$540,000Jun 2020 $11,8122025 Amount on Record Feb 2017 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

5364 Bowman Dr

5 bd · 5.5 ba · 5,074 sqft · 5.28 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,125,000Aug 2019 $17,6102025 Amount on Record May 2016 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5365 Bowman Dr

4 bd · 3.5 ba · 3,743 sqft · 0.209 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,150,000Apr 2026 $16,3612025 Amount on Record May 2023 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

5370 Bowman Dr

5 bd · 6.5 ba · 5,109 sqft · 3.33 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$950,000Dec 2017 $17,4882025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5371 Bowman Dr

4 bd · 4 ba · 3,145 sqft · 0.216 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$430,787Aug 2015 $7,3492025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5376 Bowman Dr

4 bd · 3 ba · 3,016 sqft · 1.41 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$625,000Mar 2016 $11,8502025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5377 Bowman Dr

4 bd · 3.5 ba · 3,697 sqft · 0.219 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$491,185Aug 2015 $9,3202025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5382 Bowman Dr

5 bd · 4 ba · 4,732 sqft · 0.85 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,102,000Oct 2021 $19,5082025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5383 Bowman Dr

3 bd · 2.5 ba · 2,907 sqft · 0.202 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$409,685Nov 2015 $6,4532025 2 Names on Record Owner Occupied AssessorUpdated May 2026

5388 Bowman Dr

4 bd · 3.5 ba · 3,852 sqft · 0.648 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,110,000Mar 2024 $16,9662025 Amount on Record May 2022 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

5389 Bowman Dr

4 bd · 4 ba · 3,120 sqft · 0.195 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$429,325Sep 2015 $7,3982025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5394 Bowman Dr

4 bd · 5.5 ba · 4,011 sqft · 0.276 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$981,600Mar 2022 $18,0822025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5395 Bowman Dr

4 bd · 3 ba · 2,768 sqft · 0.195 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$385,700Jan 2016 $11,0792025 2 Names on Record Owner Occupied AssessorUpdated May 2026

5400 Bowman Dr

4 bd · 4 ba · 3,887 sqft · 0.277 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$922,200May 2022 $16,0792025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5401 Bowman Dr

4 bd · 4.5 ba · 3,733 sqft · 0.196 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,250,000May 2026 $9,1072025 Amount on Record Sep 2019 1 Name on Record Assessor + 3 DocumentsUpdated Jun 2026

5406 Bowman Dr

4 bd · 4 ba · 4,220 sqft · 0.275 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$454,800Jul 2022 $17,3722025 Amount on Record Apr 2022 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5407 Bowman Dr

4 bd · 3.5 ba · 3,716 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$478,058Aug 2015 $8,1672025 2 Names on Record Assessor + 3 DocumentsUpdated May 2026

5413 Bowman Dr

4 bd · 3 ba · 2,788 sqft · 0.175 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$100Feb 2017 $6,0122025 Amount on Record Nov 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5431 Bowman Dr

4 bd · 3.5 ba · 2,238 sqft · 0.147 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$640,000Apr 2026 $6,2952025 Amount on Record Dec 2020 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

5437 Bowman Dr

4 bd · 3.5 ba · 2,785 sqft · 0.108 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$380,000Feb 2016 $10,0532025 2 Names on Record AssessorUpdated May 2026

5443 Bowman Dr

4 bd · 4.5 ba · 2,426 sqft · 0.107 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$649,000Jul 2026 $7,5632025 Amount on Record Apr 2021 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

5449 Bowman Dr

3 bd · 2.5 ba · 1,918 sqft · 0.107 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$288,080Oct 2015 $5,1392025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5455 Bowman Dr

3 bd · 2.5 ba · 2,675 sqft · 0.107 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$347,600Aug 2016 $5,3052025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5460 Bowman Dr

2 bd · 3.5 ba · 2,322 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$550,000Jul 2026 $8,9162025 Amount on Record Nov 2020 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

5461 Bowman Dr

3 bd · 3.5 ba · 1,992 sqft · 0.177 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$312,590Nov 2015 $8,3362025 2 Names on Record Assessor + 3 DocumentsUpdated May 2026

5466 Bowman Dr

3 bd · 2.5 ba · 2,284 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$339,320Sep 2016 $8,5542025 Amount on Record Jun 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

5472 Bowman Dr

3 bd · 3.5 ba · 2,147 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$339,995Mar 2019 $8,4392025 Amount on Record Mar 2017 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5478 Bowman Dr

2 bd · 3 ba · 1,838 sqft · 0.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$425,000Sep 2024 $7,9782025 Amount on Record Mar 2017 1 Name on Record Assessor + 1 DocumentUpdated May 2026

5484 Bowman Dr

3 bd · 3 ba · 2,776 sqft · 0.174 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$348,000Jan 2017 $9,6582025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5491 Bowman Dr

3 bd · 2 ba · 2,403 sqft · 0.155 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$336,755Jun 2016 $5,4032025 Amount on Record May 2016 1 Name on Record Owner Occupied AssessorUpdated May 2026

5497 Bowman Dr

3 bd · 2.5 ba · 2,672 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$397,180Apr 2016 $6,5162025 Amount on Record Mar 2016 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5503 Bowman Dr

3 bd · 3 ba · 2,017 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$319,000Mar 2017 $5,2102025 2 Names on Record Assessor + 1 DocumentUpdated May 2026

5509 Bowman Dr

2 bd · 2.5 ba · 1,735 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$348,000Feb 2021 $6,2082025 Amount on Record Nov 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5515 Bowman Dr

3 bd · 3.5 ba · 2,284 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$380,000Mar 2020 $5,9302025 Amount on Record Jan 2017 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

5521 Bowman Dr

3 bd · 2.5 ba · 2,137 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$580,000Apr 2024 $8,6012025 Amount on Record Jun 2022 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

5527 Bowman Dr

2 bd · 2.5 ba · 1,735 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$480,000Dec 2024 $6,8842025 Amount on Record Sep 2016 1 Name on Record Owner Occupied AssessorUpdated May 2026

5533 Bowman Dr

5 bd · 4 ba · 2,770 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$600,000Dec 2024 $9,4972025 Amount on Record Feb 2017 1 Name on Record Assessor + 1 DocumentUpdated May 2026

5539 Bowman Dr

3 bd · 3.5 ba · 2,005 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$524,000Dec 2025 $7,3972025 Amount on Record Apr 2022 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

5545 Bowman Dr

2 bd · 2.5 ba · 1,847 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$467,200Apr 2026 $7,8932025 Amount on Record Oct 2024 1 Name on Record Assessor + 1 DocumentUpdated Jun 2026

5551 Bowman Dr

3 bd · 2.5 ba · 2,284 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$322,000Apr 2017 $8,6322025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

5557 Bowman Dr

4 bd · 3.5 ba · 2,137 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$309,500Jun 2016 $4,9512025 —Apr 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5563 Bowman Dr

3 bd · 2.5 ba · 1,903 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$301,500Apr 2016 $4,8202025 —Jan 2016 1 Name on Record Owner Occupied AssessorUpdated May 2026

5569 Bowman Dr

4 bd · 3 ba · 2,733 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$351,886Apr 2016 $5,9322025 Amount on Record Jan 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5575 Bowman Dr

4 bd · 3.5 ba · 2,147 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$298,000Mar 2016 $5,2642025 —Jan 2016 2 Names on Record Owner Occupied AssessorUpdated May 2026

5581 Bowman Dr

3 bd · 2.5 ba · 1,876 sqft · 0.147 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$422,500Jun 2021 $6,4352025 Amount on Record Jan 2016 2 Names on Record Assessor + 4 DocumentsUpdated May 2026

5605 Bowman Dr

3 bd · 2.5 ba · 1,728 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$510,000Jan 2023 $6,8992025 Amount on Record Aug 2017 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

5611 Bowman Dr

4 bd · 3 ba · 2,292 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$557,000Dec 2025 $5,6252025 Amount on Record Mar 2018 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5617 Bowman Dr

3 bd · 3.5 ba · 1,984 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$530,000Jun 2022 $7,6632025 Amount on Record Sep 2020 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

5623 Bowman Dr

3 bd · 2.5 ba · 1,838 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$477,500Jan 2022 $7,9322025 Amount on Record Jul 2017 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

5629 Bowman Dr

3 bd · 2.5 ba · 2,284 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$585,000Jul 2022 $8,2042025 Amount on Record Jul 2017 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated May 2026

5635 Bowman Dr

4 bd · 3.5 ba · 2,147 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$419,990Nov 2020 $8,6932025 Amount on Record Oct 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5641 Bowman Dr

4 bd · 3.5 ba · 2,284 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$565,000Mar 2023 $8,9132025 Amount on Record Mar 2020 1 Name on Record Assessor + 3 DocumentsUpdated Jul 2026

5647 Bowman Dr

3 bd · 4 ba · 2,196 sqft · 0.091 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$390,000Sep 2020 $6,0282025 Amount on Record Jun 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5653 Bowman Dr

4 bd · 4.5 ba · 2,433 sqft · 0.137 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$419,816Dec 2017 $6,2242025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

Wildfire Risk on Bowman 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 29th percentile of exposed land nationally · 9th in Florida
Wildfire LikelihoodLow — about 1 in 2,994 per year
ExposureDirect
3 of 5 cells directly exposed · 5 adjoin burnable vegetation

Property Records in Nearby Streets