N Pennsylvania Avenue, Winter Park, FL
Everything we know about N Pennsylvania Avenue in Winter Park: what is for sale, what has sold, what the homes are like and which communities the street runs through — from the MLS record and county parcel data, refreshed nightly.
19 homes sit on N Pennsylvania Avenue in Winter Park, FL (ZIP 32789), built 1934–2020, a typical 2,540 sq ft with 4 bedrooms. 3 are for sale right now from $349,500 to $3,950,000. Homes that sold since 2023 went for a median $2,144,000.
For sale on N Pennsylvania Avenue now
The homes on N Pennsylvania Avenue
19 single-family. Built by decade: 1930s 2, 1950s 1, 1960s 1, 1980s 1, 1990s 7, 2000s 5, 2010s 1, 2020s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1077 N Pennsylvania Avenue | $2,144,000 | 2025-08-21 | 2004 | 3,462 |
| 1010 N Pennsylvania Avenue | $2,400,000 | 2025-03-28 | 2017 | 4,074 |
| 1020 N Pennsylvania Avenue | $1,695,000 | 2024-01-23 | 1994 | 2,609 |
| 1115 N Pennsylvania Avenue | $2,450,000 | 2023-05-24 | 2001 | 3,576 |
| 1144 N Pennsylvania Avenue | $1,299,999 | 2023-04-18 | 1995 | 2,296 |
| 1008 N Pennsylvania Avenue | $2,295,000 | 2021-12-31 | 2020 | 3,530 |
| 670 N Pennsylvania Avenue | $400,000 | 2021-04-15 | 1953 | 2,112 |
| 1091 N Pennsylvania Avenue | $1,080,000 | 2020-08-31 | 1999 | 3,315 |
| 1184 N Pennsylvania Avenue | $902,000 | 2017-03-15 | 1995 | 2,540 |
| 922 N Pennsylvania Avenue | $1,050,000 | 2017-01-13 | 2001 | 3,440 |
| 1012 N Pennsylvania Avenue | $580,000 | 2012-09-19 | 1989 | 1,034 |
| 1164 N Pennsylvania Avenue | $735,000 | 2012-05-22 | 1995 | 2,179 |
| 720 N Pennsylvania Avenue | $40,699 | 2011-08-10 | 1993 | 812 |
| 1124 N Pennsylvania Avenue | $550,000 | 2011-08-01 | 1994 | 2,179 |
| 1201 N Pennsylvania Avenue | $1,170,000 | 2009-04-24 | 2006 | 4,010 |
| 540 N Pennsylvania Avenue | $399,000 | 2007-01-30 | 1938 | 1,652 |
| 520 N Pennsylvania Avenue | $233,000 | 2005-10-21 | 1961 | 708 |
| 1129 N Pennsylvania Avenue | $787,500 | 2005-03-29 | 2003 | 3,622 |
| 600 N Pennsylvania Avenue | $140,000 | 2004-12-22 | 1934 | 816 |
Communities along N Pennsylvania Avenue
- Morseland · 4 homes on the street
- Pennsylvania Place · 2 homes on the street
- Morseland · 2 homes on the street
- Pennsylvania Place · 2 homes on the street
- Villa View Park · 1 homes on the street
- Morseland · 1 homes on the street
- Winter Park Town · 1 homes on the street
How to read this
Home counts, build years, sizes and last sales come from the county parcel record joined to MLS history; listings and 12-month closings from the live MLS feeds as of November 1, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 408 homes for sale in Winter Park, homes for sale in 32789.