
Deals & Discount Filters
Apartments under $1,500 for Rent in Winter Park, FL
518 Rentals
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1 BED, 1 BATH$1,325
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2 BEDS, 2 BATHS$1,400
3057 Aaron Burr Ave Unit 2
3057 Aaron Burr Ave, Winter Park, FL 32792 -
1 BED, 1 BATH$1,399
1000 S Semoran Blvd Unit 703
1000 S Semoran Blvd, Winter Park, FL 32792 -
STUDIO, 1 BATH$1,200
7417 Daniel Webster Dr Unit 3
7417 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,450
1166 Paseo De Las Flores Unit C
1166 Paseo De Las Flores, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,400
401 Niblick Way Unit 5
401 Niblick Way, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,400
825 N Primrose Dr Unit 106
825 N Primrose Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,200
2525 Caper Ln Unit 205
2525 Caper Ln, Maitland, FL 32751 -
6 BEDS, 2.5 BATHS$800
14 Bel Air St
14 Bel Air St, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,395
113 E Smith St Unit 6
113 E Smith St, Orlando, FL 32804 -
1 BED, 1 BATH$1,000
421 E Kennedy Blvd
421 E Kennedy Blvd, Eatonville, FL 32751 -
1 BED, 1 BATH$1,295
STRATFORD CONVENIENT 1/1 CONDO IN SEMINOLE...
134 Lewfield Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,350
Beautiful 1/1 Remodeled Condo for Rent in ... Unit 52
2929 Antique Oaks Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,295
2326 Wellington Blvd
2326 Wellington Blvd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,400
3651 N Goldenrod Rd Unit B109
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,050
525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,500
7229 Swallow Run
7229 Swallow Run, Winter Park, FL 32792 -
1 BED, 1 BATH$720
Room for rent. private bedroom with shared...
1224 Moselle Ave, Orlando, FL 32807 -
2 BEDS, 1 BATH$1,500
2nd story, 2/1, updated unit on the Winter...
2406 Branch Way, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,497
Location, Location, Location ! Completely ...
440 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,450
2 Bed/2 Bath, 2nd Floor Condo at Marbeya C...
1166 Paseo De Las Flores, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,300
907 Dowd Ave Unit 3 (Upstairs 2/1)
907 Dowd Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,140
499 Ruffel St
499 Ruffel St, Eatonville, FL 32751 -
1 BED, 1 BATH$1,040
214 S W St Unit 33
214 S W St, Eatonville, FL 32751 -
1 BED, 1 BATH$1,140
439 Ruffel St
439 Ruffel St, Eatonville, FL 32751 -
1 BED, 1 BATH$1,140
200 S W St Unit 33
200 S W St, Eatonville, FL 32751 -
STUDIO, 1 BATH$899
2223 Amherst Ave Unit B
2223 Amherst Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,200
452 Banyon Tree Cir Unit 106
452 Banyon Tree Cir, Maitland, FL 32751 -
1 BED$1,349
Azure Winter Park
3650 Summer Wind Dr, Winter Park, FL 32792 -
1 BED$1,238
Alvista Winter Park
3935 Sutton Place Blvd, Winter Park, FL 32792 -
1 BED$1,410
Whisper Lake Apartments
3250 Whisper Lake Ln, Winter Park, FL 32792 -
1 BED$1,499
The Juliette | 1 Bedroom Apartments in Orl...
1225 Moselle Ave, Orlando, FL 32807
Showing 42 of 74 results, Page 2 of 2
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Clear All FiltersWinter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 538 Sq Ft $1,383 / mo
- 1 Bedroom 708 Sq Ft $1,466 / mo
- 2 Bedrooms 1,019 Sq Ft $1,738 / mo
- 3 Bedrooms 1,271 Sq Ft $2,043 / mo
- 4 Bedrooms 1,506 Sq Ft $1,531 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 765 Sq Ft $1,404/mo
- Winter Park Pines 691 Sq Ft $1,432/mo
- Cedarwood Village 649 Sq Ft $1,480/mo
- Laurel Springs 741 Sq Ft $1,496/mo
- Eastbrook 747 Sq Ft $1,536/mo
- Villas of Casselberry 756 Sq Ft $1,554/mo
- Lake Howell 730 Sq Ft $1,569/mo
- Glenmoor 711 Sq Ft $1,582/mo
- Windward Square 779 Sq Ft $1,625/mo
- Georgetown Estates 734 Sq Ft $1,664/mo
Getting Around Winter Park
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Note: Based on community-supplied data and independent market research. Subject to change without notice.