Seminole County property records for 30 addresses on Cypress Reserve Pl, Winter Park, FL · Last verified October 2026
| Properties | 30 |
|---|---|
| Median Sale Price | $740,000 |
| Deeds and Mortgages on File | 32 |
| Median Price per Sqft | $251 |
| Owner Occupied | 87% |
| Median Annual Tax Bill | $5,365 |
| Median Year Built | 1997 |
| Median Ownership Tenure | 20 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5301 Cypress Reserve Pl |
0.025 acres | $100 Nov 1995 | Assessor Updated Dec 2025 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5302 Cypress Reserve Pl |
1.38 acres | — Oct 1995 | Assessor Updated Dec 2025 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5303 Cypress Reserve Pl |
0.163 acres | — Oct 1995 | Assessor Updated Dec 2025 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5305 Cypress Reserve Pl |
5 bd · 5 ba · 2,886 sqft built 1997 · 0.248 acres | $725,000 Jun 2022 | $7,480 2025 | Assessor + 1 Document Updated Dec 2025 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5309 Cypress Reserve Pl |
4 bd · 3 ba · 2,368 sqft built 1997 · 0.268 acres | $100 Aug 2009 | $4,676 2025 | Assessor Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5312 Cypress Reserve Pl |
4 bd · 4 ba · 3,584 sqft built 1996 · 0.323 acres | $319,000 Jun 2011 | $568 2024 | Assessor + 1 Document Updated Jan 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5313 Cypress Reserve Pl |
4 bd · 2.5 ba · 2,414 sqft built 1997 · 0.271 acres | $182,100 Dec 1997 | $3,891 2025 | Assessor Updated Apr 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5317 Cypress Reserve Pl |
4 bd · 3 ba · 2,290 sqft built 1997 · 0.277 acres | $460,000 May 2018 | $7,183 2025 | Assessor + 2 Documents Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5320 Cypress Reserve Pl |
4 bd · 4 ba · 3,122 sqft built 1998 · 0.446 acres | $530,000 Jul 2005 | $3,662 2025 | Assessor + 1 Document Updated Dec 2025 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5321 Cypress Reserve Pl |
4 bd · 3.5 ba · 2,283 sqft built 1997 · 0.325 acres | $470,000 Aug 2006 | $7,601 2025 | Assessor Updated Apr 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5325 Cypress Reserve Pl |
5 bd · 4.5 ba · 3,598 sqft built 1998 · 0.271 acres | $905,000 Mar 2026 | $8,879 2025 | Assessor + 5 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5328 Cypress Reserve Pl |
4 bd · 5 ba · 2,931 sqft built 1997 · 0.333 acres | $252,800 Apr 1997 | $4,630 2025 | Assessor Updated Dec 2025 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5329 Cypress Reserve Pl |
4 bd · 4.5 ba · 3,491 sqft built 1996 · 0.268 acres | $600,000 Mar 2022 | $7,465 2025 | Assessor + 1 Document Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5332 Cypress Reserve Pl |
5 bd · 4 ba · 3,241 sqft built 1997 · 0.352 acres | $765,000 Sep 2023 | $8,666 2025 | Assessor + 3 Documents Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5333 Cypress Reserve Pl |
4 bd · 3.5 ba · 2,433 sqft built 1997 · 0.268 acres | $750,000 Jun 2023 | $8,103 2025 | Assessor + 3 Documents Updated Apr 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5337 Cypress Reserve Pl |
4 bd · 3.5 ba · 2,557 sqft built 1997 · 0.271 acres | $320,000 Nov 2004 | $4,472 2025 | Assessor Updated Jul 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5341 Cypress Reserve Pl |
4 bd · 5 ba · 3,590 sqft built 1997 · 0.313 acres | $360,000 Oct 2010 | $5,868 2025 | Assessor + 1 Document Updated Jul 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5345 Cypress Reserve Pl |
4 bd · 3.5 ba · 2,446 sqft built 1998 · 0.294 acres | $266,900 Feb 1998 | $4,389 2025 | Assessor + 1 Document Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5349 Cypress Reserve Pl |
4 bd · 4 ba · 2,909 sqft built 1997 · 0.323 acres | $740,000 Oct 2022 | $5,590 2025 | Assessor + 2 Documents Updated Dec 2025 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5353 Cypress Reserve Pl |
4 bd · 4 ba · 2,895 sqft built 1997 · 0.454 acres | $540,000 Aug 2006 | $4,459 2025 | Assessor + 1 Document Updated Dec 2025 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5357 Cypress Reserve Pl |
4 bd · 4 ba · 3,563 sqft built 1997 · 0.273 acres | $260,200 Aug 1997 | $5,167 2025 | Assessor Updated Dec 2025 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5361 Cypress Reserve Pl |
4 bd · 3 ba · 2,722 sqft built 1997 · 0.272 acres | $480,000 Dec 2019 | $5,492 2025 | Assessor + 2 Documents Updated Dec 2025 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5364 Cypress Reserve Pl |
4 bd · 4.5 ba · 2,831 sqft built 1998 · 0.3 acres | $349,500 Dec 2003 | $4,807 2025 | Assessor + 1 Document Updated Apr 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5365 Cypress Reserve Pl |
4 bd · 5.5 ba · 3,173 sqft built 1998 · 0.268 acres | $525,000 Mar 2017 | $6,852 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5368 Cypress Reserve Pl |
4 bd · 5.5 ba · 2,946 sqft built 1997 · 0.275 acres | $251,200 Oct 1997 | $4,938 2025 | Assessor + 1 Document Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5369 Cypress Reserve Pl |
4 bd · 4 ba · 2,796 sqft built 1996 · 0.304 acres | $232,100 Oct 1996 | $4,257 2025 | Assessor Updated Dec 2025 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5372 Cypress Reserve Pl |
4 bd · 4 ba · 3,256 sqft built 1996 · 0.279 acres | $365,000 Feb 2015 | $8,991 2025 | Assessor Updated Dec 2025 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5373 Cypress Reserve Pl |
5 bd · 4.5 ba · 2,924 sqft built 1996 · 0.354 acres | $525,000 Aug 2020 | $5,147 2025 | Assessor + 1 Document Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5376 Cypress Reserve Pl |
4 bd · 4.5 ba · 3,734 sqft built 1997 · 0.421 acres | $256,800 Mar 1997 | $5,832 2025 | Assessor + 2 Documents Updated Apr 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5377 Cypress Reserve Pl |
4 bd · 5 ba · 3,252 sqft built 1996 · 0.492 acres | $424,000 Sep 2003 | $5,365 2025 | Assessor + 1 Document Updated Dec 2025 | 2 Owners on File Owner Occupied |