Orange County property records for 20 addresses on Winter Oaks Ln, Orlando, FL · Last verified October 2026
| Properties | 20 |
|---|---|
| Median Sale Price | $286,000 |
| Deeds and Mortgages on File | 21 |
| Median Price per Sqft | $209 |
| Owner Occupied | 70% |
| Median Annual Tax Bill | $2,705 |
| Median Year Built | 1989 |
| Median Ownership Tenure | 10 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4400 Winter Oaks Ln |
3 bd · 2 ba · 1,842 sqft built 1989 · 0.147 acres | $100 Aug 2017 | $508 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4401 Winter Oaks Ln |
3 bd · 2 ba · 1,414 sqft built 1989 · 0.18 acres | $89,000 Oct 1996 | $1,997 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4404 Winter Oaks Ln |
3 bd · 2 ba · 1,147 sqft built 1988 · 0.131 acres | $100 Mar 2017 | $1,577 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4408 Winter Oaks Ln |
3 bd · 2 ba · 1,147 sqft built 1988 · 0.125 acres | $107,500 Jun 2010 | $1,617 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4409 Winter Oaks Ln |
3 bd · 2 ba · 1,463 sqft built 1988 · 0.18 acres | $89,900 Dec 1998 | $1,901 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4412 Winter Oaks Ln |
3 bd · 2 ba · 1,414 sqft built 1988 · 0.135 acres | $98,300 Jan 1998 | $1,928 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4416 Winter Oaks Ln |
3 bd · 2 ba · 1,228 sqft built 1988 · 0.252 acres | $190,000 Jun 2016 | $2,881 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4420 Winter Oaks Ln |
3 bd · 2 ba · 1,147 sqft built 1989 · 0.13 acres | $165,000 Jun 2016 | $1,903 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4424 Winter Oaks Ln |
4 bd · 2 ba · 1,614 sqft built 1988 · 0.131 acres | $2,004 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4428 Winter Oaks Ln |
3 bd · 2 ba · 1,147 sqft built 1989 · 0.131 acres | $212,000 Dec 2018 | $2,785 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4432 Winter Oaks Ln |
3 bd · 2 ba · 1,220 sqft built 1989 · 0.131 acres | $4,645 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4436 Winter Oaks Ln |
3 bd · 2 ba · 1,204 sqft built 1989 · 0.131 acres | $100,000 Mar 2014 | $4,837 2025 | Assessor Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4440 Winter Oaks Ln |
3 bd · 2 ba · 1,147 sqft built 1989 · 0.129 acres | $87,000 Jan 1999 | $2,705 2025 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4444 Winter Oaks Ln |
3 bd · 2 ba · 1,220 sqft built 1989 · 0.17 acres | $360,000 Dec 2022 | $5,050 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4448 Winter Oaks Ln |
3 bd · 2 ba · 1,636 sqft built 1989 · 0.209 acres | $2,203 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4452 Winter Oaks Ln |
3 bd · 2 ba · 1,228 sqft built 1989 · 0.154 acres | $155,000 Feb 2005 | $5,148 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4455 Winter Oaks Ln |
3 bd · 2 ba · 1,228 sqft built 1989 · 0.18 acres | $286,000 Jan 2021 | $3,009 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4456 Winter Oaks Ln |
3 bd · 2 ba · 1,212 sqft built 1988 · 0.131 acres | $135,000 Apr 2004 | $5,043 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4459 Winter Oaks Ln |
3 bd · 2 ba · 1,636 sqft built 1989 · 0.18 acres | $450,000 Apr 2024 | $2,313 2025 | Assessor + 4 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
4460 Winter Oaks Ln |
3 bd · 2 ba · 1,393 sqft built 1988 · 0.15 acres | $292,000 Apr 2021 | $4,577 2025 | Assessor + 4 Documents Updated Oct 2026 | Owner on File Owner Occupied |