3 BEDS, 3.5 BATHS
$2,000
Deals & Discount Filters
Apartments under $2,000 for Rent in Winter Park, FL
1,248 Rentals
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1 BED, 1 BATH$1,5253060 George Mason Ave Unit 10C
3060 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,800668 Montego Bay Ct Unit 668
668 Montego Bay Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,900151 Stefanik Rd
151 Stefanik Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
3267 Forest Oaks Ct Unit 111
3267 Forest Oaks Ct, Winter Park, FL 32792 -
1 BED, 1 BATH$1,300
1000 S Semoran Blvd Unit 703
1000 S Semoran Blvd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,885
2111 Conifer Ave
2111 Conifer Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,6001250 S Denning Dr Unit 232
1250 S Denning Dr, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,9245167 Lazy Oaks Dr
5167 Lazy Oaks Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,450
7229 Swallow Run
7229 Swallow Run, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,600
316 Scottsdale Square Unit 316
316 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
3057 Aaron Burr Ave Unit 1
3057 Aaron Burr Ave, Winter Park, FL 32792 -
STUDIO, 1 BATH$1,2007417 Daniel Webster Dr Unit 3
7417 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,695851 Miles Ave Unit 21
851 Miles Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,705
851 Miles Ave Unit 8
851 Miles Ave, Winter Park, FL 32789 -
2 BEDS, 2.5 BATHS$1,545
7449 Wynnewood Square Unit 182
7449 Wynnewood Square, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
3019 Casselwood St
3019 Casselwood St, Winter Park, FL 32792 -
3 BEDS, 1.5 BATHS$1,4751112 Princewood Dr
1112 Princewood Dr, Orlando, FL 32810 -
2 BEDS, 1 BATH$1,4951919 Canton St
1919 Canton St, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,350
113 E Smith St Unit 6
113 E Smith St, Orlando, FL 32804 -
2 BEDS, 2 BATHS$1,550
550 Flemming Way Unit 200
550 Flemming Way, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,500
496 Banyon Tree Cir Unit 204
496 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,4501166 Paseo De Las Flores Unit C
1166 Paseo De Las Flores, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,9952512 Musselwhite Ave Unit #1
2512 Musselwhite Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,000
421 E Kennedy Blvd
421 E Kennedy Blvd, Eatonville, FL 32751 -
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, 2 BATHS$1,8001150 Carmel Cir Unit 308
1150 Carmel Cir, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,29064 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
2 BEDS, 1 BATH$1,600
825 N Primrose Dr Unit 113
825 N Primrose Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,375
2521 Caper Ln Unit 203
2521 Caper Ln, Maitland, FL 32751 -
2 BEDS, 1.5 BATHS$1,900
2822 Plaza Terrace Dr Unit 2822
2822 Plaza Terrace Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,500540 Cascade Cir Unit 104
540 Cascade Cir, Casselberry, FL 32707 -
1 BED, 1 BATH$1,1502525 Caper Ln Unit 205
2525 Caper Ln, Maitland, FL 32751 -
1 BED, 1 BATH$1,700
1483 Lake Baldwin Ln Unit C
1483 Lake Baldwin Ln, Orlando, FL 32814 -
1 BED, 1 BATH$1,650
4499 Twinview Ln
4499 Twinview Ln, Orlando, FL 32814 -
1 BED, 1 BATH$1,200"Cozy 1-Bedroom Gem with Elegant Hardwood ... Unit 123
123 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,700Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,840Fully Furnished 2/2 Condo!
7429 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,725
2Bed/1.5Bath TOWNHOUSE IN WINTER PARK!! ...
4954 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,699
Beautiful Remodeled First Floor 2/2 Condo ... Unit 17
2917 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
Charming 2-Bedroom Condo in Scenic Winter ... Unit 204
1250 S Denning Dr, Winter Park, FL 32789
Showing 42 of 190 results, Page 3 of 5
Winter Park at a Glance
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 $1,460 / mo
- 2 Bedrooms 1,020 Sq Ft $1,696 / mo
- 3 Bedrooms 1,273 Sq Ft $2,013 / 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
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About Our Deals
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Note: Based on community-supplied data and independent market research. Subject to change without notice.