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Showing all results in Winter Park, FL.

Show Nearby Apartments

Apartments under $500 for Rent in Winter Park, FL

2,023 Rentals
.
  1. Building Photo - Juno Winter Park
    $541 Off
    Price Drop. $541 Off
    |
    STUDIO
    $1,884+
    1 BED
    $2,143+
    2 BEDS
    $2,700+
    3 BEDS
    $3,189+

    Juno Winter Park

    1305 Morgan Stanley Ave, Winter Park, FL 32789
    Call
  8. Building Photo - Seabrook
    $257 Off
    Price Drop. $257 Off
    1 BED
    $1,188+
    2 BEDS
    $1,420+

    Seabrook

    3114 Terry Brook Dr, Winter Park, FL 32792
    Call
  38. Building Photo - Kingswood Apartments
    STUDIO
    $900+
    1 BED
    $1,050+
    2 BEDS
    $1,200+
    3 BEDS
    $1,600+

    Kingswood Apartments

    1101 Lee Rd, Orlando, FL 32810
  39. Building Photo - The Fisher
    2 BEDS
    $1,849

    The Fisher

    2001 Glenridge Way, Winter Park, FL 32792

Winter Park at a Glance

Average Rent

$1,500
(All bedrooms and property types)
Learn more about
Average Rent in Winter Park
6

School Rating

out of 10 Rating
Learn more about
Schools in Winter Park
22

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Winter Park
57

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Winter Park

Winter Park, FL Apartments for Rent

Winter Park captivates with its brick-lined streets, moss-draped oak trees, and interconnected chain of lakes. Apartment seekers will find themselves in a community anchored by the Charles Hosmer Morse Museum of American Art, popular scenic boat tours, and the historic Rollins College campus. The walkable downtown area along Park Avenue features boutique shopping and Central Park, where residents often gather for outdoor concerts and seasonal festivals.

Apartments in Winter Park offer easy access to Orlando while maintaining their own distinct character. The city spans 11 square miles, featuring lakes connected by navigable canals that provide year-round recreation opportunities. The centrally located Winter Park SunRail station and proximity to major roadways make commuting convenient. Current rental prices average $1,482 for a one-bedroom apartment, with options ranging from contemporary developments to renovated historic properties.

Renting in Winter Park

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winter Park

(For 1 bedroom apartments)

Getting Around Winter Park

Transportation

71

Very Walkable

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
57

Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
22

Minimal Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Scoreⓘ

Education

GreatSchools Rating
Winter Park High

Public High School

Public
Grades 9-12
3,369 Students
GreatSchools Rating
Lake Howell High School

Public High School

Public
Grades 9-12
2,205 Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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