Cheap Apartments for Rent in Winter Park, FL

2,061 Rentals

.

STUDIO

$1,320+

1 BED

$1,426+

2 BEDS

$1,819+

3 BEDS

$2,397+

The Taylor at Winter Park

2000 Village Ln, Winter Park, FL 32792

Call (562) 568-7870
$257 Off

Price Drop. $257 Off

1 BED

$1,322+

2 BEDS

$1,518+

Seabrook

3114 Terry Brook Dr, Winter Park, FL 32792

Call (689) 220-5925
1 BED, 1 BATH

$1,325

524 Georgetown Dr Unit B

524 Georgetown Dr, Casselberry, FL 32707
1 BED, 1 BATH

$1,325

STRATFORD CONVENIENT 1/1 CONDO- Walk to sh...

134 Lewfield Cir, Winter Park, FL 32792
1 BED

$1,349+

2 BEDS

$1,749+

Serena Winter Park

2890 Red Lion Sq, Winter Park, FL 32792
Exceptional Value

|

1 BED

$1,350+

2 BEDS

$1,655+

3 BEDS

$1,995+

Newport Colony Apartments in Casselberry

1166 Pointe Newport Ter, Casselberry, FL 32707

Call (689) 220-2212
2 BEDS, 1 BATH

$1,350

1820 Rogers Ave Unit B - 1

1820 Rogers Ave, Maitland, FL 32751
1 BED, 1 BATH

$1,350

1 bedroom Condo with Lake access and a pri...

524 Georgetown Dr, Casselberry, FL 32707
1 BED, 1 BATH

$1,350

Beautiful 1/1 wood floor condo for rent in... Unit 118

3014 Antique Oaks Cir, Winter Park, FL 32792
1 BED, 1 BATH

$1,350

Fantastic 1 /1 x Rent @ Winter Park's Four... Unit 412

200 St Andrews Blvd, Winter Park, FL 32792
1 BED

$1,350+

2 BEDS

$1,690+

Whisper Lake Apartments

3250 Whisper Lake Ln, Winter Park, FL 32792
1 BED

$1,356+

2 BEDS

$1,364+

3 BEDS

$1,698+

The Avenues of Baldwin Park

5800 Auvers Blvd, Orlando, FL 32807

Call (689) 220-6084
|

1 BED

$1,375+

2 BEDS

$1,539+

3 BEDS

$1,957+

Cranes Landing Apartments

3440 N Goldenrod Rd, Winter Park, FL 32792

Call (689) 219-8408
STUDIO

$1,393+

1 BED

$1,482+

2 BEDS

$1,615+

3 BEDS

$1,962+

Westmount at Winter Park

1701 Lee Rd, Winter Park, FL 32789

Call (689) 205-8291
2 BEDS, 2 BATHS

$1,395

1000 S Semoran Blvd Unit 806

1000 S Semoran Blvd, Winter Park, FL 32792
1 BED, 1 BATH

$1,399

Beautiful Full Remodeled 1/1 Condo x Rent... Unit 123

3019 Antique Oaks Cir, Winter Park, FL 32792
1 BED, 1 BATH

$1,399

FOR RENT! Fabulous Full Remodeled 1/1 Wint... Unit 5

2905 Antique Oaks Cir, Winter Park, FL 32792
1 BED, 1 BATH

$1,400

2942 Antique Oaks Cir Unit 86

2942 Antique Oaks Cir, Winter Park, FL 32792
STUDIO

$1,409+

1 BED

$1,549+

2 BEDS

$1,699+

3 BEDS

$1,999+

Azure Winter Park

3650 Summer Wind Dr, Winter Park, FL 32792
1 BED

$1,426+

2 BEDS

$1,547+

ARIUM Winter Park

3250 Bishop Park Dr, Winter Park, FL 32792

Call (321) 399-2153
1 BED, 1 BATH

$1,450

940 W Fairbanks Ave Unit In-law apartment.

940 W Fairbanks Ave, Orlando, FL 32804

Apply
Rent Special

Rent Special

|

1 BED

$1,475+

2 BEDS

$1,500+

3 BEDS

$2,025+

Oak Reserve at Winter Park

541 Oak Reserve Ln, Winter Park, FL 32792

Call (689) 220-7864
2 BEDS, 2 BATHS

$1,475

Spacious 2/2 Condo In Lancelot at Winter Park Unit B204

3651 N Goldenrod Rd, Winter Park, FL 32792
2 BEDS, 2 BATHS

$1,475

3651 N Goldenrod Rd Unit B204

3651 N Goldenrod Rd, Winter Park, FL 32792
1 BED

$1,477+

2 BEDS

$1,681+

Calibre Bend Apartments

3924 Calibre Bend Ln, Winter Park, FL 32792

Call (689) 220-7875
1 BED

$1,494+

2 BEDS

$1,668+

POSTE Winter Park

800 Semoran Park Dr, Winter Park, FL 32792

Call (689) 219-4211
2 BEDS, 1 BATH

$1,495

1434 Minnesota Ave

1434 Minnesota Ave, Winter Park, FL 32789
2 BEDS, 1 BATH

$1,495

1714 Miller Ave

1714 Miller Ave, Winter Park, FL 32789
2 BEDS, 1 BATH

$1,495

1716 Miller Ave

1716 Miller Ave, Winter Park, FL 32789
2 BEDS, 2 BATHS

$1,499

1000 S Semoran Blvd Unit 816

1000 S Semoran Blvd, Winter Park, FL 32792
2 BEDS, 1 BATH

$1,499

2406 Branch Way Unit 104

2406 Branch Way, Maitland, FL 32751
2 BEDS, 2 BATHS

$1,499

Spacious Condo Living in Winter Park – Per...

1000 S Semoran Blvd, Winter Park, FL 32792
2 BEDS, 1 BATH

$1,499

2406 Branch Way

2406 Branch Way, Maitland, FL 32751
1 BED

$1,499+

2 BEDS

$1,620+

Alvista Winter Park

3935 Sutton Place Blvd, Winter Park, FL 32792
1 BED

$1,775+

2 BEDS

$1,500+

3 BEDS

$1,995+

Hannibal Square

433 W New England Ave, Winter Park, FL 32789

Call (689) 207-3890
2 BEDS, 1 BATH

$1,500

1695 Lee Rd Unit # C-214

1695 Lee Rd, Winter Park, FL 32789
2 BEDS, 1 BATH

$1,500

2515 Formosa Ave

2515 Formosa Ave, Orlando, FL 32804
2 BEDS, 2 BATHS

$1,500

408 Banyon Tree Cir Unit 100

408 Banyon Tree Cir, Maitland, FL 32751
2 BEDS, 2 BATHS

$1,500

2 Bed/2 Bath condo in Lancelot at Winter P... Unit D103

3651 N Goldenrod Rd, Winter Park, FL 32792
2 BEDS, 2 BATHS

$1,500

2 bed 2 bath - 1st floor condo for rent

3651 N Goldenrod Rd, Winter Park, FL 32792
2 BEDS, 2 BATHS

$1,500

1073 Princewood Dr

1073 Princewood Dr, Orlando, FL 32810
|

1 BED

$1,517+

2 BEDS

$1,845+

3 BEDS

$2,094+

Cortland Lake Howell

1280 Vinings Ln, Casselberry, FL 32707

Call (321) 710-4674

Showing 42 of 268 results, Page 2 of 7

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Winter Park at a Glance

Average Rent

$1,491

(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 538 Sq Ft $1,398 / mo
1 Bedroom 707 Sq Ft $1,491 / mo
2 Bedrooms 1,019 Sq Ft $1,785 / mo
3 Bedrooms 1,271 Sq Ft $2,054 / mo
4 Bedrooms 1,506 Sq Ft $1,521 / mo

Top Budget-Friendly Neighborhoods in Winter Park

(For 1 bedroom apartments)

Neighborhoods Average Sq Ft Average Rent
Winter Park Woods 768 Sq Ft $1,444/mo
Winter Park Pines 723 Sq Ft $1,475/mo
Cedarwood Village 670 Sq Ft $1,504/mo
Four Seasons 637 Sq Ft $1,522/mo
Winter Park Pines Merrie Oaks 637 Sq Ft $1,522/mo
Eastbrook 748 Sq Ft $1,580/mo
Lake Howell 735 Sq Ft $1,620/mo
Winter Park Estates 685 Sq Ft $1,648/mo
Windward Square 781 Sq Ft $1,657/mo
Laurel Springs 737 Sq Ft $1,736/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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