1 BED, 1 BATH
$1,250
Deals & Discount Filters
No results were found that match your criteria.
Showing all results in Winter Park, FL.
Condos under $500 for Rent in Winter Park, FL
2,030 Rentals
-
-
2 BEDS, 2 BATHS$1,6301000 S Semoran Blvd Unit 813
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,5455517 Decatur St Unit 5517
5517 Decatur St, Orlando, FL 32807 -
2 BEDS, 1 BATH$2,9501504 Minnesota St
1504 Minnesota St, Orlando, FL 32803 -
2 BEDS, 2 BATHS$3,850
690 Osceola Ave Unit 502
690 Osceola Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,550
2407 Branch Way Unit 205
2407 Branch Way, Maitland, FL 32751 -
3 BEDS, 2 BATHS$3,100
424 Dunraven Dr
424 Dunraven Dr, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,800850 W Canton Ave
850 W Canton Ave, Winter Park, FL 32789 -
6 BEDS, 3.5 BATHS$10,5002234 Vía Luna
2234 Vía Luna, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,400
2101 Oakhurst Ave
2101 Oakhurst Ave, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,800
2749 Bright Bird Ln
2749 Bright Bird Ln, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,650
3651 N Goldenrod Rd Unit B207
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$6,800311 E Morse Blvd Unit 2-3
311 E Morse Blvd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,750174 Scottsdale Square Unit 174
174 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,6007404 Woodburn Ct
7404 Woodburn Ct, Winter Park, FL 32792 -
2 BEDS, 1 BATH$2,20012 W Hazel St
12 W Hazel St, Orlando, FL 32804 -
3 BEDS, 2 BATHS$3,0001938 Eland Ave
1938 Eland Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,550
3057 Aaron Burr Ave Unit 2
3057 Aaron Burr Ave, Winter Park, FL 32792 -
1 BED, 1 BATH$1,325
524 Georgetown Dr Unit B
524 Georgetown Dr, Casselberry, FL 32707 -
1 BED, 1 BATH$1,230261 Scottsdale Sq Unit 261
261 Scottsdale Sq, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,300
1620 Florentino Ln
1620 Florentino Ln, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,4501434 Minnesota Ave
1434 Minnesota Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$2,850
1504 Broad Wing Ln
1504 Broad Wing Ln, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$3,650
2490 Lauder Dr
2490 Lauder Dr, Maitland, FL 32751 -
3 BEDS, 3.5 BATHS$3,800
1147 Wildmeadow Run
1147 Wildmeadow Run, Winter Park, FL 32792 -
4 BEDS, 3.5 BATHS$5,400
5452 Penway Dr
5452 Penway Dr, Orlando, FL 32814 -
4 BEDS, 2 BATHS$3,650
2120 Deloraine Trail
2120 Deloraine Trail, Maitland, FL 32751 -
2 BEDS, 2.5 BATHS$2,995
660 Killarney Bay Ct Unit 6
660 Killarney Bay Ct, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,235
5415 Alloway St
5415 Alloway St, Orlando, FL 32810 -
2 BEDS, 2 BATHS$1,700
2534 Zelina Point
2534 Zelina Point, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$2,250
33 E Princeton St
33 E Princeton St, Orlando, FL 32804 -
3 BEDS, 2 BATHS$2,199
14 W KING St
14 W KING St, ORLANDO, FL 32804 -
2 BEDS, 1 BATH$2,450
19 W King St
19 W King St, Orlando, FL 32804 -
4 BEDS, 4.5 BATHS$3,850
1409 Lone Feather Trail
1409 Lone Feather Trail, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,700
1943 Canny Cv
1943 Canny Cv, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$4,600
336 Blue Heron Dr
336 Blue Heron Dr, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,850233 Lewfield Cir Unit 233
233 Lewfield Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,4201150 Carmel Cir Unit 308
1150 Carmel Cir, Casselberry, FL 32707 -
3 BEDS, 2 BATHS$3,040333 Cambridge Blvd
333 Cambridge Blvd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,250
559 Flemming Way Unit 105
559 Flemming Way, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,590
3651 N Goldenrod Rd Unit 107
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,400
2942 Antique Oaks Cir Unit 86
2942 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 538 Sq Ft $1,405 / mo
- 1 Bedroom 707 Sq Ft $1,501 / mo
- 2 Bedrooms 1,019 Sq Ft $1,775 / mo
- 3 Bedrooms 1,271 Sq Ft $2,051 / 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 767 Sq Ft $1,418/mo
- Winter Park Pines 723 Sq Ft $1,438/mo
- Cedarwood Village 677 Sq Ft $1,486/mo
- Four Seasons 634 Sq Ft $1,511/mo
- Winter Park Pines Merrie Oaks 634 Sq Ft $1,511/mo
- Eastbrook 740 Sq Ft $1,566/mo
- Lake Howell 734 Sq Ft $1,610/mo
- Winter Park Estates 675 Sq Ft $1,641/mo
- Windward Square 781 Sq Ft $1,642/mo
- Glenmoor 698 Sq Ft $1,703/mo
Getting Around Winter Park
Education
Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
tooltips
Submitting Request
Thank You
About Our Deals
Apartment Finder utilizes the industry's largest and most complete database of real-time rents and availabilities to help you find an amazing deal on your next rental.
Price Drop
Apartment communities change their rental rates often - sometimes multiple times a day. We track the changes and keep you up to date when a rental rate decreases.
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.