Orange County property records for 28 addresses on Carolina Ave, Winter Park, FL · Last verified October 2026
| Properties | 111 |
|---|---|
| Median Sale Price | $610,000 |
| Deeds and Mortgages on File | 127 |
| Median Price per Sqft | $386 |
| Owner Occupied | 45% |
| Median Annual Tax Bill | $6,512 |
| Median Year Built | 1982 |
| Median Ownership Tenure | 10 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20 Carolina Ave |
0.154 acres | $340,000 Dec 2025 | $2,203 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
200 Carolina Ave |
22 units · 1,151 sq ft Built 1981 | $837,500 Sep 2025 | $6,512 2025 |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
250 Carolina Ave |
22 units · 1,153 sq ft Built 1981 | $505,000 Sep 2024 | $6,211 2025 |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
300 Carolina Ave |
22 units · 1,151 sq ft Built 1981 | $725,000 Aug 2026 | $6,512 2025 |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
345 Carolina Ave |
2,136 sqft built 1985 · 0.449 acres | $2,654,000 Nov 2025 | $16,152 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
350 Carolina Ave |
21 units · 1,523 sq ft Built 2006 | $704,700 Mar 2025 | $5,543 2025 |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
359 Carolina Ave |
12,845 sqft built 1985 · 0.52 acres | $2,000,000 Nov 2019 | $35,873 2025 | Assessor + 1 Document Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
399 Carolina Ave |
10,230 sqft built 1985 · 0.564 acres | $848,200 May 1996 | $33,552 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
405 Carolina Ave |
6 bd · 5.25 ba · 4,000 sqft built 2017 · 0.133 acres | $1,675,000 Dec 2023 | $19,067 2025 | Assessor + 6 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
413 Carolina Ave |
3 bd · 2 ba · 1,092 sqft built 1996 · 0.148 acres | $42,700 Mar 1997 | $1,036 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
421 Carolina Ave |
3 bd · 1 ba · 1,110 sqft built 1955 · 0.148 acres | $138,000 Jan 2003 | $3,836 2025 | Assessor Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
422 Carolina Ave |
4 bd · 4 ba · 2,181 sqft built 2004 · 0.164 acres | $1,255,000 Aug 2023 | $15,275 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
430 Carolina Ave |
3 bd · 1 ba · 784 sqft built 1935 · 0.164 acres | $600 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
433 Carolina Ave |
5 bd · 3.5 ba · 2,557 sqft built 2018 · 0.148 acres | $1,395,000 Jun 2026 | $16,685 2025 | Assessor + 2 Documents Updated Jun 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
440 Carolina Ave |
1 bd · 1 ba · 806 sqft built 1927 · 0.164 acres | $158,000 May 2014 | $3,840 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
443 Carolina Ave |
3 bd · 1 ba · 954 sqft built 1936 · 0.148 acres | $300,000 Dec 2019 | $3,840 2025 | Assessor + 3 Documents Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
453 Carolina Ave |
3 bd · 2 ba · 1,723 sqft built 2004 · 0.148 acres | $650,000 Jun 2020 | $12,080 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
456 Carolina Ave |
6 bd · 6.25 ba · 3,086 sqft built 2004 · 0.127 acres | $975,000 Mar 2026 | $3,657 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
466 Carolina Ave |
6 bd · 5.25 ba · 4,156 sqft built 2006 · 0.164 acres | $445,000 Apr 2008 | $3,277 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
467 Carolina Ave |
4 bd · 3 ba · 2,395 sqft built 2020 · 0.148 acres | $1,125,000 Apr 2021 | $10,258 2025 | Assessor + 3 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
505 Carolina Ave |
4 bd · 4 ba · 2,313 sqft built 2019 · 0.148 acres | $210,000 Jul 2015 | $9,129 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
506 Carolina Ave |
4 bd · 4.5 ba · 2,430 sqft built 2017 · 0.164 acres | $33,837 Jun 2017 | $7,063 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
510 Carolina Ave |
3 bd · 1 ba · 1,215 sqft built 1934 · 0.164 acres | $353 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
513 Carolina Ave |
3 bd · 1 ba · 1,053 sqft built 1925 · 0.148 acres | $3,582 2025 | Assessor Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
518 Carolina Ave |
3 bd · 3 ba · 1,736 sqft built 2004 · 0.127 acres | $530,000 Oct 2016 | $12,110 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
521 Carolina Ave |
4 bd · 2 ba · 1,564 sqft built 1927 · 0.148 acres | $1,734,500 May 2023 | $10,945 2025 | Assessor + 3 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
524 Carolina Ave |
6 bd · 4.25 ba · 3,326 sqft built 2003 · 0.122 acres | $3,000,000 Dec 2015 | $7,310 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
535 Carolina Ave |
2 bd · 1 ba · 784 sqft built 1985 · 0.148 acres | $400,000 Jan 2025 | $5,563 2025 | Assessor Updated May 2026 | Owner on File |