Surprise Dr, Winter Garden, FL Property Records

Orange County property records for 17 addresses on Surprise Dr, Winter Garden, FL · Last verified September 2026

Surprise Dr Highlights

Properties 17
Median Sale Price $742,500
Deeds and Mortgages on File 31
Median Price per Sqft $250
Owner Occupied 65%
Median Annual Tax Bill $7,365
Median Year Built 1971
Median Ownership Tenure 3 years

Properties on Surprise Dr

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

1 Surprise Dr

756 sqft · built 1945 · 1.23 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on Record AssessorUpdated May 2026

21 Surprise Dr

3 bd · 2 ba · 1,105 sqft · built 1956 · 0.17 acres

Last Sale Tax Bill Prior Sale Owner Records
$53,000Jan 1996 $3222025 Owner on Record Owner Occupied AssessorUpdated May 2026

22 Surprise Dr

3 bd · 3 ba · 1,805 sqft · built 1959 · 0.264 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Nov 2023 $3,7942025 Amount on Record Aug 2017 Owner on Record Assessor + 8 DocumentsUpdated May 2026

202 Surprise Dr

4 bd · 3.5 ba · 2,769 sqft · built 2022 · 0.146 acres

Last Sale Tax Bill Prior Sale Owner Records
$668,400Nov 2022 $10,1382025 Amount on Record Sep 2021 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

205 Surprise Dr

3 bd · 2 ba · 2,076 sqft · built 1950 · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$290,000Jan 2016 $3,5872025 2 Owners on Record Assessor + 3 DocumentsUpdated Sep 2026

208 Surprise Dr

3 bd · 2.5 ba · 2,466 sqft · built 2022 · 0.155 acres

Last Sale Tax Bill Prior Sale Owner Records
$805,000Dec 2024 $10,1432025 Amount on Record Aug 2022 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

214 Surprise Dr

4 bd · 3.5 ba · 3,206 sqft · built 2023 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$785,000Oct 2023 $7,9562025 Amount on Record Sep 2021 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

220 Surprise Dr

3 bd · 2.5 ba · 2,466 sqft · built 2021 · 0.145 acres

Last Sale Tax Bill Prior Sale Owner Records
$616,800Jan 2022 $7,3652025 Amount on Record Sep 2021 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

226 Surprise Dr

4 bd · 3.5 ba · 2,747 sqft · built 2023 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$735,000Oct 2023 $10,4852025 Amount on Record Sep 2021 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

232 Surprise Dr

4 bd · 3.5 ba · 3,206 sqft · built 2023 · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$788,000Sep 2023 $11,8762025 Amount on Record Sep 2021 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

237 Surprise Dr

3 bd · 2.5 ba · 1,545 sqft · built 1947 · 0.191 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Oct 2016 $3,2892025 —Feb 2016 Owner on Record Owner Occupied AssessorUpdated May 2026

238 Surprise Dr

3 bd · 2.5 ba · 2,466 sqft · built 2023 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000May 2023 $9,4882025 Amount on Record Sep 2021 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

243 Surprise Dr

3 bd · 2 ba · 1,665 sqft · built 1950 · 0.378 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,5082025 2 Owners on Record Assessor + 3 DocumentsUpdated May 2026

244 Surprise Dr

4 bd · 3.5 ba · 2,745 sqft · built 2023 · 0.162 acres

Last Sale Tax Bill Prior Sale Owner Records
$742,500Jul 2023 $10,8782025 Amount on Record Sep 2021 Owner on Record AssessorUpdated May 2026

702 Surprise Dr

3 bd · 2 ba · 1,750 sqft · built 1971 · 0.254 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,3442025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

712 Surprise Dr

3 bd · 2 ba · 1,025 sqft · built 1971 · 0.259 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,000Jul 2008 $4,4012025 2 Owners on Record AssessorUpdated May 2026

720 Surprise Dr

3 bd · 2 ba · 1,395 sqft · built 1971 · 0.266 acres

Last Sale Tax Bill Prior Sale Owner Records
$339,000Oct 2020 $3,5742025 Amount on Record Aug 2017 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

Property Records in Nearby Streets