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Apartments for Rent in Winter Park, FL with Parking

1,038 Rentals
.
  1. Building Photo - Gables Baldwin Park
    Rent Special
    Rent Special
    |
    STUDIO
    $2,238+
    1 BED
    $2,458+
    2 BEDS
    $3,108+
    3 BEDS
    $4,367+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,190 - $4,319
    Required Monthly Fees$48
    Utilities & EssentialsVaries
    Total Monthly Price$2,238 - $4,367

    Gables Baldwin Park

    2050 Jake St, Orlando, FL 32814
    (470) 305-6691
  10. |
    1 BED
    $1,688+
    2 BEDS
    $2,075+
    3 BEDS
    $2,259+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,604 - $2,205
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,688 - $2,289

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  13. 1 Month Free
    1 Month Free
    STUDIO
    $1,903+
    2 BEDS
    $2,749+
    3 BEDS
    $3,298+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,804 - $3,475
    Required Monthly Fees$99
    Utilities & EssentialsVaries
    Total Monthly Price$1,903 - $3,574

    Enders Place at Baldwin Park

    4220 New Broad St, Orlando, FL 32814
    (689) 220-2141
  15. 1 BED
    $2,342+
    2 BEDS
    $2,876+
    3 BEDS
    $4,948+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,265 - $4,871
    Required Monthly Fees$77
    Utilities & EssentialsVaries
    Total Monthly Price$2,342 - $4,948

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  16. $250 Off
    Price Drop. $250 Off
    |
    1 BED
    $1,714+
    2 BEDS
    $2,079+
    3 BEDS
    $2,852+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,679 - $4,613
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,714 - $4,648

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  26. Rent Special
    Rent Special
    STUDIO
    $1,726+
    1 BED
    $1,930+
    3 BEDS
    $3,444+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,638 - $3,356
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,726 - $3,444

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  27. 3 BEDS
    $2,887
    Total Monthly Price Total Monthly Price New
    Base Rent$2,845
    Required Monthly Fees$42
    Utilities & EssentialsVaries
    Total Monthly Price$2,887

    400 North

    400 N Orlando Ave, Maitland, FL 32751
    (689) 219-4863
  28. $265 Off
    Price Drop. $265 Off
    STUDIO
    $1,831+
    1 BED
    $1,582+
    2 BEDS
    $2,277+
    3 BEDS
    $2,823+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,507 - $3,266
    Required Monthly Fees$75
    Total Monthly Price$1,582 - $3,341

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  33. $260 Off
    Price Drop. $260 Off
    1 BED
    $1,220+
    2 BEDS
    $1,455+
    3 BEDS
    $1,775+

    Signal Pointe

    2500 Howell Branch Rd, Winter Park, FL 32792
    (689) 220-5609
  34. 1 BED
    $1,592+
    2 BEDS
    $1,924+
    3 BEDS
    $1,956+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,441 - $2,620
    Required Monthly Fees$151
    Utilities & EssentialsVaries
    Total Monthly Price$1,592 - $2,771

    Stonecastle Apartment Homes

    2015 New Stonecastle Ter, Winter Park, FL 32792
    (689) 219-5272
  36. STUDIO
    $1,355+
    1 BED
    $1,443+
    2 BEDS
    $1,545+
    3 BEDS
    $1,851+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,344 - $2,204
    Required Monthly Fees$11
    Utilities & EssentialsVaries
    Total Monthly Price$1,355 - $2,215

    Westmount at Winter Park

    1701 Lee Rd, Winter Park, FL 32789
    (689) 205-8291
  41. $554 Off
    Price Drop. $554 Off
    1 BED
    $1,670+
    2 BEDS
    $2,061+
    3 BEDS
    $2,585+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,580 - $3,477
    Required Monthly Fees$90
    Total Monthly Price$1,670 - $3,567

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
Showing 42 of 97 results, Page 1 of 3

Winter Park at a Glance

Average Rent

$1,481
(All bedrooms and property types)
Learn more about
Average Rent in Winter Park
7

School Rating

out of 10 Rating
Learn more about
Schools in Winter Park

Winter Park, FL Apartments for Rent

Winter Park was founded as a resort community by northern business magnates in the late 19th century and has maintained its reputation as one of Central Florida's most desirable places to live. Those searching for apartments for rent in Winter Park will discover tree-lined brick streets, a chain of interconnected lakes, and the cultural centerpiece of Park Avenue, which features boutique shops, art galleries, and dining options. The city is also home to Rollins College and the Charles Hosmer Morse Museum of American Art, which houses the world's most comprehensive collection of Tiffany glass.

Renting in Winter Park provides convenient access to both local attractions and the broader Orlando metropolitan area. The city's apartment communities range from lakefront properties to garden-style residences near downtown, with options spanning studios to multi-bedroom layouts. Major highways including Interstate 4 are easily accessible for commuters heading to Orlando's business districts, theme parks, and employment centers. The 47.6-acre Mead Botanical Garden and the city's scenic canal system offer outdoor recreation, while Park Avenue's walkable downtown creates opportunities for shopping and entertainment without leaving the city limits.

Renting in Winter Park

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winter Park

(For 1 bedroom apartments)

Education

GreatSchools Rating
Winter Park High

Public High School

Public
Grades 9-12
3,369 Students
GreatSchools Rating
Winter Park High School

Public High School

Public
Grades 9-12
3,304 Students
GreatSchools Rating
Lake Howell High School

Public High School

Public
Grades 9-12
2,239 Students

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

Apartments for Rent Near Winter Park

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