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

1,229 Rentals
.
  1. Building Photo - Solis at Winter Park
    $269 Off
    Price Drop. $269 Off
    1 BED
    $1,410+
    2 BEDS
    $1,554+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,292 - $1,571
    Required Monthly Fees$118
    Utilities & EssentialsVaries
    Total Monthly Price$1,410 - $1,689

    Solis at Winter Park

    7502 Sun Key Blvd, Winter Park, FL 32792
    (321) 366-6748
  2. Building Photo - Westmount at Winter Park
    Rent Special
    Rent Special
    STUDIO
    $1,154+
    1 BED
    $1,477+
    2 BEDS
    $1,475+
    3 BEDS
    $1,878+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,143 - $2,231
    Required Monthly Fees$11
    Utilities & EssentialsVaries
    Total Monthly Price$1,154 - $2,183

    Westmount at Winter Park

    1701 Lee Rd, Winter Park, FL 32789
    (689) 205-8291
  4. $220 Off
    Price Drop. $220 Off
    1 BED
    $1,410+
    2 BEDS
    $1,725+
    3 BEDS
    $1,853+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,390 - $2,019
    Required Monthly Fees$20
    Utilities & EssentialsVaries
    Total Monthly Price$1,410 - $2,039

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
    (689) 219-8770
  11. $296 Off
    Price Drop. $296 Off
    1 BED
    $1,762
    Total Monthly Price Total Monthly Price New
    Base Rent$1,732 - $2,042
    Required Monthly Fees$30
    Total Monthly Price$1,762 - $2,072

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  13. Building Photo - Sumerset Apartments
    1 BED
    $1,074+
    2 BEDS
    $1,195+
    3 BEDS
    $1,295+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,074 - $1,495
    Required Monthly FeesNone
    Total Monthly Price$1,074 - $1,495

    Sumerset Apartments

    1051 Lee Rd, Orlando, FL 32810
  14. Good Value
    STUDIO
    $900+
    1 BED
    $1,050+
    2 BEDS
    $1,200+
    3 BEDS
    $1,600+

    Kingswood Apartments

    1101 Lee Rd, Orlando, FL 32810
  15. Building Photo - 2500 Lee Rd
    1 BED, 1 BATH
    $1,399

    2500 Lee Rd

    2500 Lee Rd, Winter Park, FL 32789
  16. Building Photo - 2500 Lee Rd
    1 BED, 1 BATH
    $1,465
    Total Monthly Price Total Monthly Price New
    Base Rent$1,465
    Required Monthly FeesNone
    Total Monthly Price$1,465

    2500 Lee Rd Unit 244

    2500 Lee Rd, Winter Park, FL 32789
  19. Building Photo - 625 Trinidad Ct
    2 BEDS, 2 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    625 Trinidad Ct Unit 625

    625 Trinidad Ct, Winter Park, FL 32792
  20. Building Photo - 118 Eaton St
    1 BED, 1 BATH
    $1,050
    Total Monthly Price Total Monthly Price New
    Base Rent$1,050
    Required Monthly FeesNone
    Total Monthly Price$1,050

    118 Eaton St Unit 4

    118 Eaton St, Eatonville, FL 32751
  27. Building Photo - 114 Eaton St
    2 BEDS, 1 BATH
    $1,190
    Total Monthly Price Total Monthly Price New
    Base Rent$1,190
    Required Monthly FeesNone
    Total Monthly Price$1,190

    114 Eaton St Unit 3

    114 Eaton St, Eatonville, FL 32751
  28. Building Photo - 1 E King St
    3 BEDS, 1 BATH
    $1,895

    1 E King St

    1 E King St, Orlando, FL 32804
  31. Building Photo - 2810 Sandwell Dr
    3 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    2810 Sandwell Dr

    2810 Sandwell Dr, Winter Park, FL 32792
    Apply
  34. 2 BEDS, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    1360 Formosa Ave Unit 1360 Formosa

    1360 Formosa Ave, Winter Park, FL 32789
  35. Building Photo - 200 Saint Andrews Blvd
    3 BEDS, 2 BATHS
    $1,150
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150
    Required Monthly FeesNone
    Total Monthly Price$1,150

    200 Saint Andrews Blvd Unit 2402

    200 Saint Andrews Blvd, Winter Park, FL 32792
  36. Building Photo - 2924 Antique Oaks Cir
    2 BEDS, 2.5 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    2924 Antique Oaks Cir Unit 48

    2924 Antique Oaks Cir, Winter Park, FL 32792
  37. 2 BEDS, 1 BATH
    $1,685
    Total Monthly Price Total Monthly Price New
    Base Rent$1,685
    Required Monthly FeesNone
    Total Monthly Price$1,685

    17 W Winter Park St Unit #17

    17 W Winter Park St, Orlando, FL 32804
  38. 1 BED, 1 BATH
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    1140 S Orlando Ave Unit Exeter E2

    1140 S Orlando Ave, Maitland, FL 32751
  40. Building Photo - 2523 Alexa Ct
    2 BEDS, 1.5 BATHS
    $1,600

    2523 Alexa Ct

    2523 Alexa Ct, Winter Park, FL 32792
Showing 42 of 165 results, Page 2 of 4

Winter Park at a Glance

Average Rent

$1,471
(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

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 737 Sq Ft $1,580/mo
  • Fairview 733 Sq Ft $1,862/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.

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