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Apartments for Rent in Winter Park, FL
1,964 Rentals
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2 BEDS, 1 BATH$2,000 -
3 BEDS, 2 BATHS$2,500226 Harvard St
226 Harvard St, Orlando, FL 32804 -
3 BEDS, 2 BATHS$2,245
410 Poplar Ct
410 Poplar Ct, Maitland, FL 32751 -
1 BED, 1 BATH$2,300
40 E Princeton St
40 E Princeton St, Orlando, FL 32804 -
5 BEDS, 8 BATHS$22,500
3260 Lake Shore Dr
3260 Lake Shore Dr, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,290
64 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
1 BED, 1 BATH$1,600
1483 Lake Baldwin Ln Unit C
1483 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,600
5314 Andrus Ave
5314 Andrus Ave, Orlando, FL 32810 -
1 BED, 1 BATH$1,280
2521 Caper Ln Unit 203
2521 Caper Ln, Maitland, FL 32751 -
3 BEDS, 3.5 BATHS$3,795
1865 Britlyn Alley
1865 Britlyn Alley, Orlando, FL 32814 -
1 BED, 1 BATH$1,799
1384 Lake Baldwin Ln Unit C
1384 Lake Baldwin Ln, Orlando, FL 32814 -
1 BED, 1 BATH$1,450
2512 Musselwhite Ave Unit 3
2512 Musselwhite Ave, Orlando, FL 32804 -
4 BEDS, 2 BATHS$3,000
1435 Oxford Rd
1435 Oxford Rd, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,650
1425 Virginia Dr
1425 Virginia Dr, Orlando, FL 32803 -
2 BEDS, 2 BATHS$2,200
1417 Belgrade Ave
1417 Belgrade Ave, Orlando, FL 32803 -
3 BEDS, 3.5 BATHS$3,700
1438 Chatfield Pl
1438 Chatfield Pl, Orlando, FL 32814 -
2 BEDS, 2 BATHS$1,600
5532 Charleston St
5532 Charleston St, Orlando, FL 32807 -
4 BEDS, 3.5 BATHS$3,500
1745 E Adams Dr
1745 E Adams Dr, Maitland, FL 32751 -
3 BEDS, 2 BATHS$3,200
1120 Hunter Ave
1120 Hunter Ave, Orlando, FL 32804 -
3 BEDS, 1 BATH$2,295
3511 Backspin Ln
3511 Backspin Ln, Orlando, FL 32804 -
3 BEDS, 2.5 BATHS$3,390
1507 Lake Baldwin Ln
1507 Lake Baldwin Ln, Orlando, FL 32814 -
3 BEDS, 2 BATHS$2,900
1200 Tanager Dr
1200 Tanager Dr, Orlando, FL 32803 -
3 BEDS, 2 BATHS$2,7951300 Michigan Ave
1300 Michigan Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$4,000Luxurious living in Winter Park
236 Rippling Ln, Winter Park, FL 32789 -
1 BED, 1 BATH$1,399
3044 Antique Oaks Cir Unit 178
3044 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,500
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 -
3 BEDS, 2 BATHS$2,199
2111 Biscayne Dr
2111 Biscayne Dr, Winter Park, FL 32789 -
2 BEDS, 1.5 BATHS$2,000
200 St Andrews Blvd Unit 2903
200 St Andrews Blvd, Winter Park, FL 32792 -
4 BEDS, 2.5 BATHS$3,295
1039 Wildmeadow Run
1039 Wildmeadow Run, 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$1,849
2606 Aloma Ave
2606 Aloma Ave, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,550
2 Bed 1 Bath Condo | Pet Friendly | Washer...
1695 Lee Rd, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$3,200
1710 Aster Dr
1710 Aster Dr, Winter Park, FL 32792 -
3 BEDS, 1 BATH$2,150
REMODELED 3 BEDROOM / 1 BATH / CARPORT (WI...
931 Cypress Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,125
139 Scottsdale Square
139 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,695
226 Lewfield Cir Unit 226
226 Lewfield Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
2651 Cayman Way
2651 Cayman Way, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,250
2458 Grand Teton Cir Unit 1
2458 Grand Teton Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,600
1817 Loch Berry Rd
1817 Loch Berry Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,690
Cozy 2 bed 2 bath in Winter Park
211 Stefanik Rd, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,000
Winter Park Town Home
2553 Galliano Cir, Winter Park, FL 32792
Showing 42 of 331 results, Page 6 of 8
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 $1,367 / mo
- 1 Bedroom 708 Sq Ft $1,449 / mo
- 2 Bedrooms 1,020 Sq Ft $1,715 / mo
- 3 Bedrooms 1,270 Sq Ft $2,008 / 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 762 Sq Ft $1,342/mo
- Four Seasons 599 Sq Ft $1,360/mo
- Winter Park Pines Merrie Oaks 599 Sq Ft $1,360/mo
- Winter Park Pines 693 Sq Ft $1,428/mo
- Eastbrook 718 Sq Ft $1,488/mo
- Laurel Springs 727 Sq Ft $1,507/mo
- Cedarwood Village 637 Sq Ft $1,514/mo
- Glenmoor 706 Sq Ft $1,531/mo
- Lake Howell 733 Sq Ft $1,532/mo
- Villas of Casselberry 761 Sq Ft $1,541/mo
Average Rent in Nearby Cities
(For 1 bedroom apartments)- Cities Average Rent
- Winter Park $1,588/mo
- Maitland $1,716/mo
- Fern Park $1,252/mo
- Eatonville $900/mo
- Casselberry $1,648/mo
- Longwood $1,715/mo
- Altamonte Springs $1,607/mo
- Lockhart $1,407/mo
- Orlando $1,644/mo
- Pine Castle $1,294/mo
Getting Around Winter Park
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