Old Sycamore Loop, Winter Garden, FL Property Records

Orange County property records for 33 addresses on Old Sycamore Loop, Winter Garden, FL · Last verified July 2026

Old Sycamore Loop Highlights

Properties 33
Median Sale Price $587,500
Deeds and Mortgages on File 67
Median Price per Sqft $245
Owner Occupied 94%
Median Annual Tax Bill $7,150
Median Year Built 2015
Median Ownership Tenure 8 years

Properties on Old Sycamore Loop

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

4301 Old Sycamore Loop

5 bd · 3.5 ba · 4,023 sqft · 0.234 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$411,800Jul 2014 $7,3832025 2 Names on Record Owner Occupied AssessorUpdated May 2026

4306 Old Sycamore Loop

5 bd · 3.5 ba · 3,786 sqft · 0.26 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$930,000Jul 2022 $13,6662025 Amount on Record Jan 2015 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

4307 Old Sycamore Loop

5 bd · 4.5 ba · 3,159 sqft · 0.182 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$591,000Aug 2021 $9,1782025 Amount on Record Aug 2015 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

4312 Old Sycamore Loop

4 bd · 3 ba · 2,726 sqft · 0.202 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$335,100Aug 2014 $5,7932025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4313 Old Sycamore Loop

4 bd · 3 ba · 2,726 sqft · 0.152 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$389,500Jun 2018 $7,0722025 Amount on Record Dec 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4318 Old Sycamore Loop

4 bd · 3.5 ba · 3,206 sqft · 0.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$475,000Dec 2019 $7,5632025 Amount on Record Aug 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4319 Old Sycamore Loop

4 bd · 3.5 ba · 3,181 sqft · 0.246 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$555,000Jan 2020 $7,8562025 Amount on Record Jan 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4324 Old Sycamore Loop

5 bd · 4 ba · 2,851 sqft · 0.472 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$454,000Apr 2019 $6,6192025 Amount on Record Mar 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4330 Old Sycamore Loop

5 bd · 3.5 ba · 3,216 sqft · 0.307 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$377,906Jan 2015 $6,7482025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4336 Old Sycamore Loop

4 bd · 3 ba · 2,343 sqft · 0.168 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$317,699Aug 2015 $5,4212025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4342 Old Sycamore Loop

4 bd · 2 ba · 2,019 sqft · 0.161 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$294,211Nov 2016 $5,6642025 Amount on Record Oct 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4348 Old Sycamore Loop

3 bd · 2 ba · 2,709 sqft · 0.184 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$328,057Oct 2014 $5,1572025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4349 Old Sycamore Loop

4 bd · 3 ba · 2,765 sqft · 0.153 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$438,500Aug 2019 $9,2002025 Amount on Record Mar 2016 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

4354 Old Sycamore Loop

5 bd · 3.5 ba · 3,313 sqft · 0.177 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$397,000Apr 2015 $7,3642025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4355 Old Sycamore Loop

3 bd · 3 ba · 2,224 sqft · 0.14 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$579,000Nov 2023 $6,0162025 Amount on Record Feb 2015 1 Name on Record Owner Occupied AssessorUpdated May 2026

4360 Old Sycamore Loop

4 bd · 3 ba · 2,548 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$625,000Apr 2026 $7,8872025 —Feb 2026 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

4361 Old Sycamore Loop

4 bd · 3 ba · 2,782 sqft · 0.14 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$351,500Feb 2016 $6,7172025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4402 Old Sycamore Loop

6 bd · 4 ba · 4,547 sqft · 0.169 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$412,500Jan 2015 $8,6322025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4403 Old Sycamore Loop

3 bd · 2 ba · 2,224 sqft · 0.14 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$301,400Oct 2015 $5,3082025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4408 Old Sycamore Loop

3 bd · 3 ba · 2,218 sqft · 0.14 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$587,500Jan 2023 $9,2442025 Amount on Record Apr 2017 1 Name on Record Assessor + 5 DocumentsUpdated May 2026

4409 Old Sycamore Loop

3 bd · 2 ba · 1,748 sqft · 0.14 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$285,960Sep 2014 $4,4662025 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

4414 Old Sycamore Loop

4 bd · 3 ba · 2,721 sqft · 0.141 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$410,000Nov 2019 $9,5742025 Amount on Record Sep 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4415 Old Sycamore Loop

3 bd · 2 ba · 2,019 sqft · 0.14 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$302,612Feb 2017 $5,1592025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

4420 Old Sycamore Loop

4 bd · 3 ba · 2,772 sqft · 0.143 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$363,600Jan 2016 $6,2142025 2 Names on Record Owner Occupied AssessorUpdated May 2026

4421 Old Sycamore Loop

4 bd · 3.5 ba · 2,788 sqft · 0.14 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$392,000Apr 2019 $6882025 Amount on Record — 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated May 2026

4426 Old Sycamore Loop

4 bd · 3 ba · 2,749 sqft · 0.146 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$422,000Aug 2019 $6,3212025 Amount on Record Jul 2015 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

4427 Old Sycamore Loop

4 bd · 3.5 ba · 3,286 sqft · 0.206 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$384,894Nov 2017 $7,1502025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4432 Old Sycamore Loop

5 bd · 3.5 ba · 4,581 sqft · 0.266 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$420,000Sep 2014 $8,4212025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4438 Old Sycamore Loop

4 bd · 2.5 ba · 2,390 sqft · 0.256 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$330,000Feb 2015 $8,9242025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4444 Old Sycamore Loop

4 bd · 2 ba · 1,916 sqft · 0.143 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$560,000Apr 2022 $7,3582025 Amount on Record Apr 2015 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

4450 Old Sycamore Loop

4 bd · 2 ba · 1,999 sqft · 0.152 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$330,000Aug 2018 $5,0462025 Amount on Record Oct 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4456 Old Sycamore Loop

4 bd · 2 ba · 1,915 sqft · 0.162 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$312,200Aug 2018 $7,6682025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4462 Old Sycamore Loop

5 bd · 3.5 ba · 3,663 sqft · 0.275 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$441,300Aug 2018 $7,9882025 Amount on Record Feb 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

Wildfire Risk on Old Sycamore Loop

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

Wildfire RiskNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach of burnable land

Property Records in Nearby Streets