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  2. Building Photo - 1627 Orange Ave
    3 BEDS, 2 BATHS
    $2,750
    Total Monthly Price Total Monthly Price New
    Base Rent$2,750
    Required Monthly FeesNone
    Total Monthly Price$2,750

    1627 Orange Ave

    1627 Orange Ave, Winter Park, FL 32789
  3. Building Photo - 662 Callahan St
    2 BEDS, 1 BATH
    $2,499
    Total Monthly Price Total Monthly Price New
    Base Rent$2,499
    Required Monthly FeesNone
    Total Monthly Price$2,499

    662 Callahan St Unit SI ID1545989P

    662 Callahan St, Winter Park, FL 32789
  6. Building Photo - 2710 Amherst Ave
    1 BED, 1 BATH
    $2,993
    Total Monthly Price Total Monthly Price New
    Base Rent$2,993
    Required Monthly FeesNone
    Total Monthly Price$2,993

    2710 Amherst Ave Unit SI ID1018188P

    2710 Amherst Ave, Orlando, FL 32804
  7. Building Photo - 1 E King St
    3 BEDS, 1 BATH
    $1,795

    1 E King St

    1 E King St, Orlando, FL 32804
  15. 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
  16. 3 BEDS, 2 BATHS
    $5,800
    Total Monthly Price Total Monthly Price New
    Base Rent$5,800
    Required Monthly FeesNone
    Total Monthly Price$5,800

    2721 E Marks St

    2721 E Marks St, Orlando, FL 32803
  17. 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
  26. 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
  27. 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
  28. 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
  29. 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
  30. 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
  31. 1 BED, 1 BATH
    $2,450
    Total Monthly Price Total Monthly Price New
    Base Rent$2,450
    Required Monthly FeesNone
    Total Monthly Price$2,450

    151 N Orlando Ave Unit 262

    151 N Orlando Ave, Winter Park, FL 32789
    Apply
  33. Pool #1 on the Lake - 2912 Plaza Terrace Dr
    2 BEDS, 2 BATHS
    $2,275
    Total Monthly Price Total Monthly Price New
    Base Rent$2,275
    Required Monthly FeesNone
    Total Monthly Price$2,275

    2912 Plaza Terrace Dr

    2912 Plaza Terrace Dr, Orlando, FL 32803
    Apply
  34. 2 BEDS, 2 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    1920 Woodcrest Dr Unit 13

    1920 Woodcrest Dr, Winter Park, FL 32792
  35. 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
  36. 3 BEDS, 2 BATHS
    $2,400
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400
    Required Monthly FeesNone
    Total Monthly Price$2,400

    530 Byron Rd

    530 Byron Rd, Winter Park, FL 32792
  37. Building Photo - 2407 Branch Way
    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 283 results, Page 3 of 7

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
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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)

Average Rent in Nearby Cities

(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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