2 BEDS, 1 BATH
$1,345
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Showing all results in Winter Park, FL.
Apartments under $500 for Rent in Winter Park, FL
1,917 Rentals
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2 BEDS, 2.5 BATHS$2,5001041 Aragon Ave
1041 Aragon Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$3,950
1275 Michigan Ave
1275 Michigan Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$2,600
1998 Canny Cv
1998 Canny Cv, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,625
3651 N Goldenrod Rd Unit D201
3651 N Goldenrod Rd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,800
404 Banyon Tree Cir Unit 200
404 Banyon Tree Cir, Maitland, FL 32751 -
1 BED, 1 BATH$1,300
3060 George Mason Ave Unit 10C
3060 George Mason Ave, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$3,300
1410 Lake Baldwin Ln
1410 Lake Baldwin Ln, Orlando, FL 32814 -
3 BEDS, 2.5 BATHS$2,695
216 Harvard St
216 Harvard St, Orlando, FL 32804 -
2 BEDS, 2 BATHS$3,600
220 Overlook Rd
220 Overlook Rd, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,400
496 Banyon Tree Cir Unit 104
496 Banyon Tree Cir, Maitland, FL 32751 -
5 BEDS, 5.5 BATHS$19,000
1221 Richmond Rd
1221 Richmond Rd, Winter Park, FL 32789 -
4 BEDS, 3 BATHS$4,000
350 N Phelps Ave
350 N Phelps Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,250
724 W Fairbanks Ave
724 W Fairbanks Ave, Orlando, FL 32804 -
3 BEDS, 2.5 BATHS$2,800
1480 Broad Wing Ln
1480 Broad Wing Ln, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,6002651 Cayman Way
2651 Cayman Way, Winter Park, FL 32792 -
3 BEDS, 2.25 BATHS$3,3001308 Lake Baldwin Ln
1308 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,350
496 Banyon Tree Cir
496 Banyon Tree Cir, Maitland, FL 32751 -
3 BEDS, 2 BATHS$2,200
2458 Grand Teton Cir Unit 1
2458 Grand Teton Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,100
452 Banyon Tree Cir Unit 106
452 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,129
3651 N Goldenrod Rd
3651 N Goldenrod Rd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,400
1817 Loch Berry Rd
1817 Loch Berry Rd, Winter Park, FL 32789 -
4 BEDS, 2 BATHS$2,595
530 Ventris Ct
530 Ventris Ct, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,690
Cozy 2 bed 2 bath in Winter Park
211 Stefanik Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,700
Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,400
2055 Eaton St
2055 Eaton St, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,345
2183 Crandon Ave Unit 1
2183 Crandon Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,295
1/1 Condo in Summit Village Casselberry Unit 104
536 Cascade Cir, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,095
114 Eaton St Unit 2
114 Eaton St, Eatonville, FL 32751 -
4 BEDS, 2 BATHS$2,700
724 Forest Glen Ct
724 Forest Glen Ct, Maitland, FL 32751 -
4 BEDS, 3 BATHS$4,995
1525 Palmer Ave
1525 Palmer Ave, Winter Park, FL 32789 -
4 BEDS, 3.5 BATHS$5,250
LUXURY RENTAL In Maitland - Winter Park Area 32751
1610 Lyndale Blvd, Maitland, FL 32751 -
1 BED, 1 BATH$1,050
525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,425
3007 George Mason Ave Unit H
3007 George Mason Ave, Winter Park, FL 32792 -
3 BEDS, 3.5 BATHS$3,500
3-story, 3/3.5, updated, townhome in the heart of Baldwin Park!
2011 Meeting Pl, Orlando, FL 32814 -
4 BEDS, 4.25 BATHS$25,000
281 Shell Point E
281 Shell Point E, Maitland, FL 32751 -
3 BEDS, 3 BATHS$2,495
7542 Cranes Creek Ct
7542 Cranes Creek Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,740
Rent Special: Receive $100 in rent credit ...
7429 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,400
2nd story, 2/1, updated unit on the Winter Park/Maitland border!!
2406 Branch Way, Maitland, FL 32751 -
1 BED, 1 BATH$860
ROOM FOR RENT WITH PRIVATE BATHROOM
1224 Moselle Ave, Orlando, FL 32807 -
2 BEDS, 2 BATHS$2,000
551 Finchley Rd
551 Finchley Rd, Maitland, FL 32751 -
8 BEDS, 6 BATHS$16,550
1860 Vía Contessa
1860 Vía Contessa, Winter Park, FL 32789
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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Best Value
"Best value" units are located in buildings rated three stars or higher. We label apartment rentals that are priced significantly less than similar high-quality units nearby.
Rent Specials
Apartment communities regularly advertise deals for new residents. Whether it's a move-in special or a free tv, we locate the rentals that offer a little something extra when you sign your lease.
Note: Based on community-supplied data and independent market research. Subject to change without notice.