Orange County property records for 53 addresses on Olive Hill Dr, Winter Garden, FL · Last verified October 2026
| Properties | 53 |
|---|---|
| Median Sale Price | $425,042 |
| Deeds and Mortgages on File | 106 |
| Median Price per Sqft | $198 |
| Owner Occupied | 79% |
| Median Annual Tax Bill | $7,092 |
| Median Year Built | 2019 |
| Median Ownership Tenure | 6 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
4 bd · 3 ba · 2,470 sqft · built 2019 · 0.229 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $832,000Jun 2024 | $10,0142025 | Amount on Record Sep 2019 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3 ba · 2,176 sqft · built 2020 · 0.214 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $401,065Sep 2020 | $8,8282025 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 3.5 ba · 2,909 sqft · built 2019 · 0.159 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $407,366Aug 2019 | $7,5122025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2020 · 0.127 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $565,000Aug 2024 | $7,9442025 | Amount on Record Aug 2020 | Owner on Record | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2.5 ba · 2,569 sqft · built 2019 · 0.145 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $373,266Jun 2019 | $6,9302025 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 2 ba · 1,676 sqft · built 2020 · 0.118 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $317,900Mar 2020 | $7,4392025 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 2,470 sqft · built 2019 · 0.146 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $385,044Sep 2019 | $6,1892025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2019 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $559,000Aug 2024 | $8,4142025 | Amount on Record Oct 2019 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 2,909 sqft · built 2019 · 0.146 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $544,900May 2021 | $9,0672025 | Amount on Record Sep 2019 | 2 Owners on Record Owner Occupied | Assessor + 5 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2019 · 0.112 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $436,500Jul 2021 | $6,5802025 | Amount on Record Jan 2020 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
4 bd · 3 ba · 2,470 sqft · built 2019 · 0.146 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $403,662Sep 2019 | $6,1892025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2019 · 0.111 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $324,584Jan 2020 | $5,5262025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2019 · 0.111 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $365,422Dec 2019 | $5,5332025 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 2,130 sqft · built 2019 · 0.146 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $361,322Aug 2019 | $5,7212025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2019 · 0.116 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $332,511Jan 2020 | $8,3852025 | 2 Owners on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 2,020 sqft · built 2019 · 0.146 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $370,000Nov 2020 | $8,4242025 | Amount on Record Aug 2019 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3 ba · 2,176 sqft · built 2019 · 0.117 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $382,800Jan 2020 | $8,7842025 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2019 · 0.118 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $340,600Jan 2020 | $7,5372025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 2,020 sqft · built 2019 · 0.146 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $325,735May 2019 | $8,7572025 | 2 Owners on Record | Assessor + 2 DocumentsUpdated Aug 2026 |
3 bd · 2.5 ba · 2,176 sqft · built 2019 · 0.18 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $599,900May 2026 | $8,7252025 | Amount on Record Oct 2019 | Owner on Record | Assessor + 4 DocumentsUpdated Jul 2026 |
4 bd · 3.5 ba · 2,909 sqft · built 2019 · 0.143 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $615,000Dec 2021 | $10,8622025 | Amount on Record Sep 2019 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 2.5 ba · 2,470 sqft · built 2019 · 0.181 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $385,244Oct 2019 | $7,6222025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 2,176 sqft · built 2019 · 0.191 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $389,131Sep 2019 | $6,0392025 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2019 · 0.124 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $565,000Jul 2024 | $7,7462025 | Amount on Record Oct 2019 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2.5 ba · 2,371 sqft · built 2019 · 0.123 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $397,708Dec 2019 | $7,5132025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 2,176 sqft · built 2019 · 0.121 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $365,124Dec 2019 | $5,7862025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2019 · 0.185 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $565,000Nov 2025 | $5,2172025 | Amount on Record Nov 2019 | 2 Owners on Record | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 3 ba · 2,688 sqft · built 2019 · 0.19 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $403,151Apr 2019 | $7682025 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 3 ba · 2,688 sqft · built 2019 · 0.173 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $383,200Feb 2019 | $6,6162025 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3 ba · 2,688 sqft · built 2019 · 0.222 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $424,222Jun 2019 | $5,5132025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 3 ba · 3,460 sqft · built 2019 · 0.21 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,140,000Mar 2025 | $12,8362025 | Amount on Record Aug 2019 | Owner on Record | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 3 ba · 3,137 sqft · built 2019 · 0.203 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $488,249Jul 2019 | $8,5472025 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 3 ba · 2,592 sqft · built 2019 · 0.198 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $377,740May 2019 | $6,6222025 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
4 bd · 3 ba · 3,137 sqft · built 2019 · 0.174 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $493,148Jun 2019 | $7,5052025 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
4 bd · 3 ba · 3,137 sqft · built 2019 · 0.175 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $446,194May 2019 | $6,3012025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
5,336 sqft · built 2019 · 4.17 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $52025 | 2 Owners on Record | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,688 sqft · built 2019 · 0.172 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $368,013May 2019 | $6,6882025 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
5 bd · 3.5 ba · 3,681 sqft · built 2019 · 0.17 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $442,074May 2019 | $8,0512025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
4 bd · 3 ba · 2,576 sqft · built 2019 · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $413,102Sep 2019 | $9,8562025 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 2,224 sqft · built 2019 · 0.236 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $655,000Apr 2025 | $4,4692025 | Amount on Record Feb 2019 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 2,470 sqft · built 2019 · 0.153 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $417,980Aug 2019 | $7682025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2.5 ba · 2,585 sqft · built 2019 · 0.191 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $807,000Jun 2025 | $7,0952025 | Amount on Record Jun 2020 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
5 bd · 3 ba · 2,381 sqft · built 2020 · 0.195 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $398,809Dec 2020 | $6,4212025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2.5 ba · 2,381 sqft · built 2020 · 0.116 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $633,000Oct 2023 | $6,2422025 | Amount on Record Aug 2021 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2020 · 0.113 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $354,006Apr 2020 | $7,4582025 | Owner on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 2,176 sqft · built 2020 · 0.11 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,8112025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 1,676 sqft · built 2020 · 0.11 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $331,992Apr 2020 | $7,7782025 | 2 Owners on Record | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,676 sqft · built 2020 · 0.11 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $480,000Mar 2024 | $7,0922025 | Amount on Record Jul 2020 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 2,176 sqft · built 2020 · 0.111 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $389,812Mar 2020 | $6,0702025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 2,176 sqft · built 2020 · 0.119 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $373,297Apr 2020 | $6,0542025 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 1,860 sqft · built 2020 · 0.128 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $373,593Apr 2020 | $5,6062025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2.5 ba · 2,381 sqft · built 2020 · 0.134 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $410,892Mar 2020 | $6,4512025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 2,176 sqft · built 2020 · 0.182 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $425,042May 2020 | $6,0162025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |