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

1,072 Rentals
.
  2. Building Photo - Signal Pointe
    $340 Off
    Price Drop. $340 Off
    1 BED
    $1,235+
    2 BEDS
    $1,485+
    3 BEDS
    $1,775+

    Signal Pointe

    2500 Howell Branch Rd, Winter Park, FL 32792
    (689) 220-5609
  3. STUDIO
    $1,355+
    1 BED
    $1,443+
    2 BEDS
    $1,553+
    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
  10. $554 Off
    Price Drop. $554 Off
    1 BED
    $1,670
    Total Monthly Price Total Monthly Price New
    Base Rent$1,580 - $1,848
    Required Monthly Fees$90
    Total Monthly Price$1,670 - $1,938

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  12. Building Photo - Sumerset Apartments
    Good Value
    1 BED
    $1,074+
    2 BEDS
    $1,274+
    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
  13. Exceptional Value
    STUDIO
    $900+
    1 BED
    $1,050+
    2 BEDS
    $1,200+
    3 BEDS
    $1,600+

    Kingswood Apartments

    1101 Lee Rd, Orlando, FL 32810
  17. Building Photo - 2500 Lee Rd
    1 BED, 1 BATH
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    2500 Lee Rd Unit 244

    2500 Lee Rd, Winter Park, FL 32789
  19. Building Photo - 2500 Lee Rd
    1 BED, 1 BATH
    $1,250

    2500 Lee Rd

    2500 Lee Rd, Winter Park, FL 32789
  21. Building Photo - 551 Flemming Way
    1 BED, 1 BATH
    $1,150
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150
    Required Monthly FeesNone
    Total Monthly Price$1,150

    551 Flemming Way Unit 201

    551 Flemming Way, Maitland, FL 32751
  26. Building Photo - 118 Eaton St
    1 BED, 1 BATH
    $950
    Total Monthly Price Total Monthly Price New
    Base Rent$950
    Required Monthly FeesNone
    Total Monthly Price$950

    118 Eaton St Unit 4

    118 Eaton St, Eatonville, FL 32751
  27. Building Photo - 1 E King St
    3 BEDS, 1 BATH
    $1,795

    1 E King St

    1 E King St, Orlando, FL 32804
  29. Building Photo - 1250 S Denning Dr
    2 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    1250 S Denning Dr Unit 127

    1250 S Denning Dr, Winter Park, FL 32789
    Apply
  30. Building Photo - 5312 Poinsetta Ave
    1 BED, 1 BATH
    $1,000
    Total Monthly Price Total Monthly Price New
    Base Rent$1,000
    Required Monthly FeesNone
    Total Monthly Price$1,000

    5312 Poinsetta Ave Unit 2

    5312 Poinsetta Ave, Winter Park, FL 32792
    Apply
  31. Building Photo - 2037 Linden Rd
    STUDIO, 1 BATH
    $1,245+
    1 BED, 1 BATH
    $1,245+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,245
    Required Monthly FeesNone
    Total Monthly Price$1,245

    2037 Linden Rd Unit 2037lindenrdA

    2037 Linden Rd, Winter Park, FL 32792
    Apply
  32. 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
    Apply
  33. 2 BEDS, 2 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    622 St Johns Ct

    622 St Johns Ct, Winter Park, FL 32792
    Apply
  36. 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
  37. Building Photo - 3373 Cedar Springs Pl
    2 BEDS, 2.5 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    3373 Cedar Springs Pl

    3373 Cedar Springs Pl, Winter Park, FL 32792
  38. 2 BEDS, 2 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    1920 Woodcrest Dr Unit 13

    1920 Woodcrest Dr, Winter Park, FL 32792
  39. Discounts
    Discounts
    1 BED, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    468 Banyon Tree Cir Unit 202

    468 Banyon Tree Cir, Maitland, FL 32751
  40. 2 BEDS, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    2407 Branch Way Unit 105

    2407 Branch Way, Maitland, FL 32751
Showing 42 of 171 results, Page 2 of 5

Winter Park at a Glance

Average Rent

$1,479
(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)

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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