Cheap Apartments for Rent in Winter Park, FL

1,957 Rentals

.

STUDIO

$1,949+

1 BED

$1,902+

2 BEDS

$2,225+

Vida at Health Village

2680 N Orange Ave, Orlando, FL 32804

Call (321) 621-2828
2 BEDS, 2 BATHS

$1,924

5167 Lazy Oaks Dr

5167 Lazy Oaks Dr, Winter Park, FL 32792
2 BEDS, 2 BATHS

$1,925

Audubon Park 2/2 Corner Unit Villa with La...

3162 Plaza Terrace Dr, Orlando, FL 32803
$443 Off

Price Drop. $443 Off

|

STUDIO

$1,937+

1 BED

$1,930+

2 BEDS

$2,190+

3 BEDS

$3,172+

Juno Winter Park

1305 Morgan Stanley Ave, Winter Park, FL 32789

Call (321) 732-6086
3 BEDS, 2 BATHS

$1,949

3469 Seagrape Dr

3469 Seagrape Dr, Winter Park, FL 32792

Call (833) 742-0874
1 BED

$1,950+

2 BEDS

$2,103+

Maitland City Centre

160-190 Independence Ln, Maitland, FL 32751

Call (689) 219-4732
2 BEDS, 2 BATHS

$1,950

652 Grenadine Ct

652 Grenadine Ct, Winter Park, FL 32792

Call (321) 204-7807 Apply
3 BEDS, 2 BATHS

$1,950

Winter Park Corner Lot

1902 Azalea Ave, Winter Park, FL 32792
2 BEDS, 2.5 BATHS

$1,950

232 Sandlewood Trail

232 Sandlewood Trail, Winter Park, FL 32789
2 BEDS, 1 BATH

$1,950

124 W Hazel St

124 W Hazel St, Orlando, FL 32804
2 BEDS, 2 BATHS

$1,975

1016 Arthur Ave

1016 Arthur Ave, Orlando, FL 32804
1 Month Free

1 Month Free

|

STUDIO

$2,187+

1 BED

$1,995+

2 BEDS

$2,975+

3 BEDS

$4,481+

Gables Baldwin Park

2050 Jake St, Orlando, FL 32814

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

$1,995

2512 Musselwhite Ave Unit 1

2512 Musselwhite Ave, Orlando, FL 32804

Call (321) 320-7316 Apply
2 BEDS, 1 BATH

$1,995

2512 Musselwhite Ave Unit #1

2512 Musselwhite Ave, Orlando, FL 32804
2 BEDS, 1 BATH

$1,995

Charming 2-Bedroom Home within 3 miles of ...

581 E Horatio Ave, Maitland, FL 32751
3 BEDS, 2.5 BATHS

$1,995

7473 Belle River Ct

7473 Belle River Ct, Winter Park, FL 32792
1 BED, 1 BATH

$2,000

2687 Stanfield Ave

2687 Stanfield Ave, Orlando, FL 32814

Call (321) 948-2329
2 BEDS, 1 BATH

$2,000

12 W Hazel St

12 W Hazel St, Orlando, FL 32804
2 BEDS, 2.5 BATHS

$2,000

33 E Princeton St

33 E Princeton St, Orlando, FL 32804
3 BEDS, 3.5 BATHS

$2,000

235 Sandlewood Trail

235 Sandlewood Trail, Winter Park, FL 32789
4 BEDS, 2 BATHS

$2,000

Nice 4/2 Two-Story Home in Seminole County...

5587 Pats Point, Winter Park, FL 32792
3 BEDS, 1 BATH

$2,050

1805 Edwin Blvd

1805 Edwin Blvd, Winter Park, FL 32789
$950 Off

Price Drop. $950 Off

1 BED

$2,066+

2 BEDS

$2,150+

3 BEDS

$3,878+

Baldwin Harbor

1771-1887 Jake St, Orlando, FL 32814

Call (689) 207-3563
3 BEDS, 2 BATHS

$2,075

5351 Cypress Dr

5351 Cypress Dr, Winter Park, FL 32792

Call (888) 990-4684
3 BEDS, 2 BATHS

$2,090

2717 Amsden Rd

2717 Amsden Rd, Winter Park, FL 32792

Call (407) 284-4494
3 BEDS, 1 BATH

$2,090

4435 Fairview Ave

4435 Fairview Ave, Orlando, FL 32804

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

$2,100

551 Finchley Rd

551 Finchley Rd, Maitland, FL 32751
3 BEDS, 2 BATHS

$2,140

7413 Fieldcrest Ave

7413 Fieldcrest Ave, Winter Park, FL 32792

Call (888) 990-4684
2 BEDS, 1 BATH

$2,150

1004 Fleck Ave

1004 Fleck Ave, Orlando, FL 32804
3 BEDS, 2 BATHS

$2,150

3005 Casselwood St

3005 Casselwood St, Winter Park, FL 32792
2 BEDS, 1 BATH

$2,150

1919 Azalea Ave

1919 Azalea Ave, Winter Park, FL 32792
3 BEDS, 2 BATHS

$2,179

7116 Green Needle Dr

7116 Green Needle Dr, Winter Park, FL 32792

Call (833) 742-0874
2 BEDS, 1 BATH

$2,195

2203 Oregon St

2203 Oregon St, Orlando, FL 32803
3 BEDS, 2 BATHS

$2,195

2828 Salisbury Blvd

2828 Salisbury Blvd, Winter Park, FL 32789
4 BEDS, 2 BATHS

$2,199

4 Bed 2 Bath Home Near Baldwin & Winter Park

5210 Sunrise Blvd, Orlando, FL 32803
2 BEDS, 1.5 BATHS

$2,200

AVAILALBE OCTOBER! Two story Townhouse loc...

848 Miles Ave, Winter Park, FL 32789
Rent Special

Rent Special

|

1 BED

$2,208+

2 BEDS

$2,711+

Paseo at Winter Park Village

940 W Canton Ave, Winter Park, FL 32789

Call (689) 220-3817
4 BEDS, 2 BATHS

$2,235

5216 N Indiana Ave

5216 N Indiana Ave, Winter Park, FL 32792

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

$2,250

824 Town Cir

824 Town Cir, Maitland, FL 32751
1 BED, 1 BATH

$2,250

1911 Canton St

1911 Canton St, Orlando, FL 32803
1 BED, 1.5 BATHS

$2,250

690 Osceola Ave Unit 407

690 Osceola Ave, Winter Park, FL 32789
3 BEDS, 2 BATHS

$2,250

1995 Water Ln

1995 Water Ln, Maitland, FL 32751

Showing 42 of 311 results, Page 5 of 8

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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

7

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 539 Sq Ft $1,365 / mo
1 Bedroom 709 Sq Ft $1,459 / mo
2 Bedrooms 1,020 Sq Ft $1,696 / mo
3 Bedrooms 1,273 Sq Ft $2,015 / mo
4 Bedrooms 1,506 Sq Ft $1,535 / mo

Top Budget-Friendly Neighborhoods in Winter Park

(For 1 bedroom apartments)

Neighborhoods Average Sq Ft Average Rent
Winter Park Woods 760 Sq Ft $1,415/mo
Winter Park Pines 668 Sq Ft $1,420/mo
Eastbrook 737 Sq Ft $1,438/mo
Four Seasons 622 Sq Ft $1,450/mo
Winter Park Pines Merrie Oaks 622 Sq Ft $1,450/mo
Laurel Springs 742 Sq Ft $1,473/mo
Albert Lee Ridge 743 Sq Ft $1,493/mo
Cedarwood Village 657 Sq Ft $1,537/mo
Villas of Casselberry 775 Sq Ft $1,561/mo
Georgetown Estates 735 Sq Ft $1,573/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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