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Showing all results in Winter Park, FL.
Apartments under $500 for Rent in Winter Park, FL
1,915 Rentals
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2 BEDS, 2 BATHS$2,450 -
3 BEDS, 2.5 BATHS$2,575Grayson Square
1878 Erudite Wy, Winter Park, FL 32792 -
1 BED, 1 BATH$1,325
Beautiful 1/1 Wood Floors Condo for Rent in Winter Park Unit 6
2905 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,195
1432 Lantry Ct
1432 Lantry Ct, Orlando, FL 32804 -
20 BEDS, 2 BATHS$1,575
Beautiful Winter Park 2/2 Condo on the first floor x Rent in front of Full Sail ! Unit 71
2936 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,449
1245 Virginia Dr Unit 1243COR
1245 Virginia Dr, Orlando, FL 32803 -
3 BEDS, 2 BATHS$1,850
Well maintained townhome in Winter Park
2349 Inagua Way, Winter Park, FL 32792 -
1 BED, 1 BATH$1,350
200 St Andrews Blvd Unit 200 St. Andrews Blvd 606
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,545
5537 Decatur St
5537 Decatur St, Orlando, FL 32807 -
1 BED, 1 BATH$1,300
Adorable 1 Bed 1 Bath Winter Park Condo
3014 Antique Oaks Cir, Winter Park, FL 32792 -
4 BEDS, 1 BATH$2,200
917 Fremont Ave
917 Fremont Ave, Winter Park, FL 32789 -
4 BEDS, 2 BATHS$3,500
1235 Ayrshire St
1235 Ayrshire St, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,475
McLean Fairway 3022D Unit 3022D
3022 Fairway Ln, Orlando, FL 32804 -
3 BEDS, 2 BATHS$3,000
216 Rippling Ln
216 Rippling Ln, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,795
1300 Michigan Ave
1300 Michigan Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,300
3044 Antique Oaks Cir Unit 178
3044 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,400
929 Dupont Ave
929 Dupont Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,350
Fully Remodeled Winter Park Home
7323 Antietam Ct W, Winter Park, FL 32792 -
5 BEDS, 3 BATHS$3,000
2181 Linden Rd
2181 Linden Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$4,200
206 Quayside Cir Unit 103
206 Quayside Cir, Maitland, FL 32751 -
3 BEDS, 2 BATHS$3,450
1594 Common Way Rd
1594 Common Way Rd, Orlando, FL 32814 -
2 BEDS, 2 BATHS$1,850
1016 Arthur Ave Unit 1016
1016 Arthur Ave, Orlando, FL 32804 -
3 BEDS, 2.5 BATHS$2,300
824 Town Cir
824 Town Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,600
5485 Decatur St Unit Decatur 5485
5485 Decatur St, Orlando, FL 32807 -
2 BEDS, 1.5 BATHS$1,895
200 St Andrews Blvd Unit 2903
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,500
2/2, updated, 1st floor condo, in Winter Park
101 Lewfield Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,200
1710 Aster Dr
1710 Aster Dr, Winter Park, FL 32792 -
3 BEDS, 1 BATH$1,995
REMODELED 3 BEDROOM / 1 BATH / CARPORT (WINTER PARK!)
931 Cypress Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$2,000
Gorgeous updated 2-bedroom 2-bath home with garage and fenced in backyard
727 W Fairbanks Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,125
139 Scottsdale Square
139 Scottsdale Square, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,250
Winter Park Charmer
2862 Kings Deer Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,050
2326 Wellington Blvd
2326 Wellington Blvd, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,399
1502 Michigan Ave
1502 Michigan Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,195
148 Oak Grove Rd
148 Oak Grove Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,350
2807 Formosa Ave
2807 Formosa Ave, Orlando, FL 32804 -
2 BEDS, 2 BATHS$1,799
Stunning All Upgraded 2/2 Condo x Rent @ Winter Park Village next to Full Sail ! Unit 633
633 Trinidad Ct, Winter Park, FL 32792 -
3 BEDS, 2.25 BATHS$3,200
2963 Upper Park Rd
2963 Upper Park Rd, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,475
McLean Fairway 3036D Unit 3036D
3036 Fairway Ln, Orlando, FL 32804 -
2 BEDS, 2.5 BATHS$1,575
7431 Glen Oaks Way Unit 89
7431 Glen Oaks Way, Winter Park, FL 32792 -
1 BED, 1 BATH$1,500
Charming Condo Retreat in Winter Park - Spacious 727 sq. ft. Home with lots of Community Features! Unit 601
200 St Andrews Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,300
Stylish Remodeled 1BR Condo with Pool & Low HOA – Ideal Winter Park Investment Unit N-10C
3060 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,599
Beautiful Remodeled Winter Park 2/2 Condo for Rent in Front of Full Sail. Unit 132
3020 Antique Oaks Cir, Winter Park, FL 32792
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 $1,347 / mo
- 1 Bedroom 707 Sq Ft $1,448 / mo
- 2 Bedrooms 1,019 Sq Ft $1,734 / mo
- 3 Bedrooms 1,273 Sq Ft $2,021 / mo
- 4 Bedrooms 1,506 Sq Ft $1,540 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 761 Sq Ft $1,362/mo
- Whisperwood 753 Sq Ft $1,376/mo
- Four Seasons 605 Sq Ft $1,379/mo
- Winter Park Pines Merrie Oaks 605 Sq Ft $1,379/mo
- Laurel Springs 744 Sq Ft $1,401/mo
- Winter Park Pines 669 Sq Ft $1,425/mo
- Eastbrook 749 Sq Ft $1,482/mo
- Lake Howell 748 Sq Ft $1,528/mo
- Glenmoor 716 Sq Ft $1,532/mo
- Villas of Casselberry 763 Sq Ft $1,539/mo
Getting Around Winter Park
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Note: Based on community-supplied data and independent market research. Subject to change without notice.