13 communities researched · Public resident-feedback themes, advertised rents and property details · Updated Sep 2026
Winter Park's rental market spans upscale mid-rise communities near Park Avenue and Winter Park Village to more affordable garden-style complexes along the Goldenrod Road and University Boulevard corridor toward east Orlando. The city's walkable downtown, tree-lined streets, and proximity to Rollins College and the SunRail line make it one of the more sought-after rental markets in Greater Orlando.
As of mid-2026 public listings, 1BR rents run roughly $1,650-$2,500+ near downtown/Winter Park Village and the Fairview area close to Park Avenue, while 1BR units along the Goldenrod Road/University Boulevard corridor and Seminole County-line neighborhoods typically start around $1,200-$1,700. Apartments.com lists the citywide average 1BR rent near $1,490/month, up roughly 2% year-over-year.
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| Complex | Neighborhood | Beds | Advertised rents | Built |
|---|---|---|---|---|
| Calibre Bend Apartments | East Winter Park, Calibre Bend Ln near University Square | 1-2 BR | $1,499-$2,018 | 1987 |
| Cranes Landing Apartments | East Winter Park, N Goldenrod Rd near Full Sail University | 1-3 BR | $1,160-$2,026 | 1990 |
| Liv at Winter Park Apartment Homes | East Winter Park, N Goldenrod Rd, lakeside | Studio-3 BR | $1,281-$3,452 | 1973 |
| Oak Reserve at Winter Park | East Winter Park, Oak Reserve Ln off University Blvd | 1-3 BR | $1,425-$2,025 | 1972 |
| Central Place At Winter Park | East Winter Park, University Blvd near Goldenrod Rd | 1-3 BR | $1,215-$1,815 | 1974 |
| Vintage Winter Park Apartments | East Winter Park, off N Goldenrod Rd near University Blvd | 1-3 BR | $1,919-$2,830 | 2018 |
| Park East - Park Knowles Apartments | Eastside, N Knowles Ave near Rollins College and Winter Park Village | Studio-2 BR | $1,280-$1,560 | 1961 |
| Seven41 Winter Park | Fairview, Clay St near downtown Winter Park | Studio-2 BR | $1,585-$2,295 | 2021 |
| Elon Winter Park | Fairview, Nicolet Ave near Park Avenue | 1 BR | $1,674-$1,708 | 1972 |
| Sapphire Winter Park | Lake Howell area, near the Winter Park/Seminole County line | 1-3 BR | $1,199-$1,699 | — |
| Juno Winter Park | Morgan Stanley Ave, near Harry P. Leu Gardens and downtown Winter Park | Studio-3 BR | $1,840-$2,734 | 2017 |
| Bainbridge Winter Park | Morgan Stanley Ave, near the Winter Park SunRail/Amtrak station | 1-3 BR | $1,605-$2,999 | 2019 |
| Paseo at Winter Park Village | Winter Park Village, W Canton Ave | 1-3 BR | $2,026-$3,498 | 2015 |
Rents are approximate, from public listings at the research date — confirm with the property.
Renters insurance is not optional here. Many Florida leases require it, and standard policies generally do not cover flood damage — that may require separate coverage, even in an apartment. Before signing, look up the building's flood zone on FEMA's flood map service and ask which evacuation zone it sits in.
Ask about the real monthly cost. A recurring theme in public resident feedback is fee stacking: valet trash, common-area electric, mandatory bulk internet, pest control, admin and tech fees. Get the full itemized monthly figure in writing before you apply.
Tour with the AC running and ask about hurricanes. Humidity control is the difference between a fine unit and a moldy one; ask how old the AC is. And ask directly how the building handled the last major storm — communities that performed well say so happily, and reviewers call out the ones that didn't.
Once you've picked a place, our Winter Park directory covers the rest of the move — movers, internet, utilities setup, and every home service you'll need.
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