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Apartments under $2,000 for Rent in Winter Park, FL

980 Rentals
.
  9. |
    1 BED
    $1,809+
    2 BEDS
    $1,997+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,676 - $2,022
    Required Monthly Fees$133
    Utilities & EssentialsVaries
    Total Monthly Price$1,809 - $2,155

    Vintage Winter Park Apartments

    7490 Dwell Well Way, Winter Park, FL 32792
    (689) 220-1305
  10. Rent Special
    Rent Special
    1 BED
    $1,254+
    2 BEDS
    $1,583+

    Seabrook

    3114 Terry Brook Dr, Winter Park, FL 32792
    (689) 220-5925
  11. Good Value
    |
    1 BED
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,749 - $1,988
    Required Monthly Fees$101
    Utilities & EssentialsVaries
    Total Monthly Price$1,850 - $2,089

    Village at Baldwin Park

    2055 Lake Baldwin Ln, Orlando, FL 32814
    (352) 632-9622
  12. $265 Off
    Price Drop. $265 Off
    STUDIO
    $1,798
    Total Monthly Price Total Monthly Price New
    Base Rent$1,699 - $1,749
    Required Monthly Fees$99
    Utilities & EssentialsVaries
    Total Monthly Price$1,798 - $1,848

    Enders Place at Baldwin Park

    4220 New Broad St, Orlando, FL 32814
    (689) 220-2141
  14. $566 Off
    Price Drop. $566 Off
    1 BED
    $1,962
    Total Monthly Price Total Monthly Price New
    Base Rent$1,885 - $1,981
    Required Monthly Fees$77
    Utilities & EssentialsVaries
    Total Monthly Price$1,962 - $2,058

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  15. Rent Special
    Rent Special
    |
    1 BED
    $1,694
    Total Monthly Price Total Monthly Price New
    Base Rent$1,659 - $2,160
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,694 - $2,195

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  16. $165 Off
    Price Drop. $165 Off
    |
    1 BED
    $1,545+
    2 BEDS
    $1,863+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,461 - $1,979
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,545 - $2,063

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  18. Good Value
    |
    1 BED
    $1,570
    Total Monthly Price Total Monthly Price New
    Base Rent$1,570 - $1,822
    Utilities & EssentialsVaries
    Total Monthly Price$1,570 - $1,822

    The Adeline

    304 Lake Ave, Maitland, FL 32751
    (689) 219-8866
  30. $200 Off
    Price Drop. $200 Off
    1 BED
    $1,049+
    2 BEDS
    $1,299+

    Soraya

    1485 Ash Cir, Casselberry, FL 32707
    (689) 205-8365
  32. 1 BED
    $1,968
    Total Monthly Price Total Monthly Price New
    Base Rent$1,926
    Required Monthly Fees$42
    Utilities & EssentialsVaries
    Total Monthly Price$1,968

    400 North

    400 N Orlando Ave, Maitland, FL 32751
    (689) 219-4863
  33. Good Value
    STUDIO
    $1,831+
    1 BED
    $1,719+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,644 - $1,815
    Required Monthly Fees$75
    Total Monthly Price$1,719 - $1,890

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  34. 1 Month Free
    1 Month Free
    STUDIO
    $1,827+
    1 BED
    $2,044+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,739 - $1,996
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,827 - $2,084

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  39. 1 BED
    $1,592+
    2 BEDS
    $1,932+
    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
  40. $403 Off
    Price Drop. $403 Off
    1 BED
    $1,422+
    2 BEDS
    $1,408+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,290 - $1,472
    Required Monthly Fees$118
    Utilities & EssentialsVaries
    Total Monthly Price$1,408 - $1,590

    Solis at Winter Park

    7502 Sun Key Blvd, Winter Park, FL 32792
    (321) 366-6748
  42. Rent Special
    Rent Special
    1 BED
    $1,443+
    2 BEDS
    $1,542+
    3 BEDS
    $1,850+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,432 - $2,204
    Required Monthly Fees$11
    Utilities & EssentialsVaries
    Total Monthly Price$1,443 - $2,215

    Westmount at Winter Park

    1701 Lee Rd, Winter Park, FL 32789
    (689) 205-8291
Showing 42 of 183 results, Page 1 of 5

Winter Park at a Glance

Average Rent

$1,474
(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)
  • Neighborhoods Average Sq Ft Average Rent
  • Lake Howell 727 Sq Ft $1,536/mo
  • Fairview 741 Sq Ft $1,796/mo

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

Winter Park Apartments for Rent in Your Budget

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