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  5. Building Photo - 2075 Jewell Ave
    5 BEDS, 4 BATHS
    $6,700
    Total Monthly Price Total Monthly Price New
    Base Rent$6,700
    Required Monthly FeesNone
    Total Monthly Price$6,700

    2075 Jewell Ave

    2075 Jewell Ave, Winter Park, FL 32789
  7. Building Photo - 2500 Lee Rd
    1 BED, 1 BATH
    $1,399

    2500 Lee Rd

    2500 Lee Rd, Winter Park, FL 32789
  13. Building Photo - 1 E King St
    3 BEDS, 1 BATH
    $1,895

    1 E King St

    1 E King St, Orlando, FL 32804
  15. Building Photo - 109 E Winter Park St
    2 BEDS, 1 BATH
    $1,925
    Total Monthly Price Total Monthly Price New
    Base Rent$1,925
    Required Monthly FeesNone
    Total Monthly Price$1,925

    109 E Winter Park St

    109 E Winter Park St, Orlando, FL 32804
  17. Building Photo - 2721 E Marks St
    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
  18. 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
  19. 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
  27. Building Photo - 641 Brookside Rd
    5 BEDS, 3 BATHS
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500

    641 Brookside Rd

    641 Brookside Rd, Maitland, FL 32751
  29. 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
  30. Building Photo - 1901 Magnolia Ave
    2 BEDS, 1 BATH
    $1,150
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150
    Required Monthly FeesNone
    Total Monthly Price$1,150

    1901 Magnolia Ave

    1901 Magnolia Ave, Winter Park, FL 32792
    Apply
  32. 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, 2 BATHS
    $2,695
    Total Monthly Price Total Monthly Price New
    Base Rent$2,695
    Required Monthly FeesNone
    Total Monthly Price$2,695

    2912 Plaza Terrace Dr

    2912 Plaza Terrace Dr, Orlando, FL 32803
    Apply
  35. 1 BED, 1 BATH
    $1,100
    Total Monthly Price Total Monthly Price New
    Base Rent$1,100
    Required Monthly FeesNone
    Total Monthly Price$1,100

    2333 Winter Park Rd Unit Guest House

    2333 Winter Park Rd, Winter Park, FL 32789
  36. 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
  37. Building Photo - 1840 Bachman Way
    3 BEDS, 2.5 BATHS
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500

    1840 Bachman Way

    1840 Bachman Way, Winter Park, FL 32792
  38. Building Photo - 223 Sandlewood Trl
    3 BEDS, 3.5 BATHS
    $2,950
    Total Monthly Price Total Monthly Price New
    Base Rent$2,950
    Required Monthly FeesNone
    Total Monthly Price$2,950

    223 Sandlewood Trl

    223 Sandlewood Trl, Winter Park, FL 32789
  39. 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
  40. 3 BEDS, 2 BATHS
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800

    840 Bethune Dr

    840 Bethune Dr, Orlando, FL 32810
Showing 42 of 278 results, Page 3 of 7

Winter Park at a Glance

Average Rent

$1,483
(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 $1,560/mo
  • Fairview 738 Sq Ft $1,876/mo

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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