Cheap Apartments for Rent in Winter Park, FL

1,832 Rentals

.

1 BED

$1,980+

2 BEDS

$2,473+

3 BEDS

$3,719+

Perla Gem Lake

100 Boucle Jeanne Cir, Maitland, FL 32751

Call (321) 248-7034
3 BEDS, 1.5 BATHS

$1,995

776 Carew Ave

776 Carew Ave, Orlando, FL 32804
2 BEDS, 2 BATHS

$1,995

Winter Park Apartment Great Location Unit 102

101 S Interlachen Ave, Winter Park, FL 32789
3 BEDS, 2 BATHS

$1,999

3028 Patel Dr

3028 Patel Dr, Winter Park, FL 32792

Call (833) 742-0874
3 BEDS, 2 BATHS

$2,000

3050 Autumn Ct

3050 Autumn Ct, Winter Park, FL 32792

Call (407) 435-2196
2 BEDS, 1.5 BATHS

$2,000

2011 Cornell Ave

2011 Cornell Ave, Winter Park, FL 32789
3 BEDS, 2 BATHS

$2,000

319 Eaton St

319 Eaton St, Maitland, FL 32751
3 BEDS, 1 BATH

$2,000

College Park 3 Bed

12 E Preston St, Orlando, FL 32804
3 BEDS, 2 BATHS

$2,050

448 Banyon Tree Cir Unit 102

448 Banyon Tree Cir, Maitland, FL 32751

Call (347) 906-1118
1 Month Free

1 Month Free

|

STUDIO

$2,175+

1 BED

$2,081+

2 BEDS

$2,920+

3 BEDS

$4,456+

Gables Baldwin Park

2050 Jake St, Orlando, FL 32814

Call (470) 305-6691
2 BEDS, 1 BATH

$2,100

19 W King St

19 W King St, Orlando, FL 32804
3 BEDS, 2 BATHS

$2,140

1381 Viburnum Ln

1381 Viburnum Ln, Winter Park, FL 32792

Call (844) 395-3959
2 BEDS, 2 BATHS

$2,150

1250 S Denning Dr Unit 112

1250 S Denning Dr, Winter Park, FL 32789
2 BEDS, 2 BATHS

$2,195

3007 Ash Park Point

3007 Ash Park Point, Winter Park, FL 32792
3 BEDS, 2 BATHS

$2,195

1432 Lantry Ct

1432 Lantry Ct, Orlando, FL 32804
3 BEDS, 3.5 BATHS

$2,200

195 Sandlewood Trail

195 Sandlewood Trail, Winter Park, FL 32789
3 BEDS, 2 BATHS

$2,200

1931 Carrigan Ave

1931 Carrigan Ave, Winter Park, FL 32792
3 BEDS, 2 BATHS

$2,200

2458 Grand Teton Cir Unit 1

2458 Grand Teton Cir, Winter Park, FL 32792
3 BEDS, 3 BATHS

$2,200

1718 Gulfview Dr

1718 Gulfview Dr, Maitland, FL 32751
3 BEDS, 2 BATHS

$2,245

1247 Kingston Ave

1247 Kingston Ave, Orlando, FL 32807

Call (407) 284-4494
3 BEDS, 2 BATHS

$2,245

1247 Kingston Ave

1247 Kingston Ave, Orlando, FL 32807
3 BEDS, 1 BATH

$2,250

3511 Backspin Ln

3511 Backspin Ln, Orlando, FL 32804
3 BEDS, 2 BATHS

$2,250

1621 Winter Green Blvd

1621 Winter Green Blvd, Winter Park, FL 32792
3 BEDS, 2.5 BATHS

$2,250

3 bed 2.5 bath Townhome w 1 car garage

2684 Galliano Cir, Winter Park, FL 32792
4 BEDS, 2 BATHS

$2,265

2045 Houndslake Dr

2045 Houndslake Dr, Winter Park, FL 32792

Call (844) 395-3959
3 BEDS, 2 BATHS

$2,275

3055 Autumn Ct

3055 Autumn Ct, Winter Park, FL 32792
3 BEDS, 2.5 BATHS

$2,275

824 Town Cir

824 Town Cir, Maitland, FL 32751
3 BEDS, 2 BATHS

$2,295

1879 Meadowgold Ln

1879 Meadowgold Ln, Winter Park, FL 32792
3 BEDS, 2 BATHS

$2,345

2310 Sunderland Rd

2310 Sunderland Rd, Maitland, FL 32751

Call (888) 990-4684
4 BEDS, 2.5 BATHS

$2,350

2886 Carew Ave

2886 Carew Ave, Winter Park, FL 32789
3 BEDS, 2 BATHS

$2,350

1148 Park Green Pl

1148 Park Green Pl, Winter Park, FL 32789
4 BEDS, 2 BATHS

$2,399

1117 Princewood Dr

1117 Princewood Dr, Orlando, FL 32810

Call (407) 258-2448
Rent Special

Rent Special

3 BEDS, 2 BATHS

$2,400

3221 Thistle Hill Dr

3221 Thistle Hill Dr, Aloma, FL 32792

Call (888) 652-2272
3 BEDS, 2.5 BATHS

$2,400

7522 Aloma Pines Ct

7522 Aloma Pines Ct, Winter Park, FL 32792
2 BEDS, 1 BATH

$2,400

1766 Miller Ave

1766 Miller Ave, Winter Park, FL 32789
3 BEDS, 3 BATHS

$2,400

7542 Cranes Creek Ct

7542 Cranes Creek Ct, Winter Park, FL 32792
3 BEDS, 2 BATHS

$2,400

1948 Eland Ave

1948 Eland Ave, Winter Park, FL 32789
Rent Special

Rent Special

3 BEDS, 2 BATHS

$2,425

5133 Oak Hill Dr

5133 Oak Hill Dr, Winter Park, FL 32792

Call (407) 284-4494
3 BEDS, 2 BATHS

$2,425

5133 Oak Hill Dr

5133 Oak Hill Dr, Winter Park, FL 32792
3 BEDS, 2 BATHS

$2,495

1826 Pineview Cir

1826 Pineview Cir, Winter Park, FL 32792
3 BEDS, 2 BATHS

$2,495

Beautiful 3bd 2bth Home with patio and large back yard available now! Great Location! Landscaping...

882 Prim Dr, Orlando, FL 32803
3 BEDS, 1.5 BATHS

$2,500

1622 Arbor Park Dr

1622 Arbor Park Dr, Winter Park, FL 32789

Showing 42 of 282 results, Page 5 of 7

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Winter Park at a Glance

Average Rent

$1,459

(All bedrooms and property types)

Learn more about

Average Rent in Winter Park

6

School Rating

out of 10 Rating

Learn more about

Schools in Winter Park

22

Some Transit

out of 100 TransitScore^® Rating

Learn more about

Transportation in Winter Park

57

Somewhat Bikeable

out of 100 BikeScore^® Rating

Learn more about

Transportation in Winter Park

Renting in Winter Park

Average Rental Rates and Apartment Sizes

Apartment Type Average Sq Ft Average Rent
Studio 537 Sq Ft $1,394 / mo
1 Bedroom 707 Sq Ft $1,459 / mo
2 Bedrooms 1,020 Sq Ft $1,729 / mo
3 Bedrooms 1,273 Sq Ft $2,006 / mo
4 Bedrooms 1,506 Sq Ft $1,544 / mo

Top Budget-Friendly Neighborhoods in Winter Park

(For 1 bedroom apartments)

Neighborhoods Average Sq Ft Average Rent
Four Seasons 594 Sq Ft $1,258/mo
Winter Park Pines Merrie Oaks 594 Sq Ft $1,258/mo
Winter Park Pines 700 Sq Ft $1,414/mo
Winter Park Woods 764 Sq Ft $1,424/mo
Laurel Springs 737 Sq Ft $1,432/mo
Eastbrook 726 Sq Ft $1,454/mo
Lake Howell 746 Sq Ft $1,541/mo
Winter Park Estates 678 Sq Ft $1,551/mo
Cedarwood Village 668 Sq Ft $1,575/mo
Villas of Casselberry 733 Sq Ft $1,580/mo

Getting Around Winter Park

Transportation

71

Very Walkable

out of 100 WalkScore^® Rating

You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.

57

Bikeable

out of 100 BikeScore^® Rating

You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.

22

Minimal Transit

out of 100 TransitScore^® Rating

You'll likely want a car when living in this area since it has few transit options.

Scores provided by Walk Score^ⓘ

Education

High School

GreatSchools Rating

Winter Park High

Public High School

Public

Grades 9-12

3,369 Students

GreatSchools Rating

Lake Howell High School

Public High School

Public

Grades 9-12

2,205 Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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