Apartments and houses for rent in Winter Park, FL
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For Rent
For Sale37 listings
747 Maryland Ave, Winter Park, FL 32789
$2,500
786 sqft
3 beds
2 baths
June 01, 2026 - Source: realtor.com
New
2 hours ago
503 Kilshore Ln, Winter Park, FL 32789
$2,250
1125 sqft
2 beds
1 bath
June 01, 2026 - Source: realtor.com
New
6 hours ago
2806 Summerfield Rd, Winter Park, FL 32792
$3,600
1961 sqft
4 beds
2 baths
June 01, 2026 - Source: realtor.com
New
8 hours ago
640 N Park Ave #5, Winter Park, FL 32789
$3,200
673 sqft
1 bed
1 bath
May 30, 2026 - Source: redfin.com
New
2 days ago
640 N Park Ave #5, Winter Park, FL 32789
$3,200
673 sqft
1 bed
1 bath
May 29, 2026 - Source: trulia.com
New
3 days ago
1119 S Pennsylvania Ave, Winter Park, FL 32789
$5,200
3000 sqft
4 beds
3 baths
May 29, 2026 - Source: redfin.com
New
3 days ago
1415 Harmon Ave, Winter Park, FL 32789
$3,060
1700 sqft
3 beds
3 baths
May 28, 2026 - Source: redfin.com
New
4 days ago
300 Killarney Dr, Winter Park, FL 32789
$7,900
2476 sqft
4 beds
3 baths
May 27, 2026 - Source: redfin.com
New
4 days ago
151 N Orlando Ave #118, Winter Park, FL 32789
$2,500
1500 sqft
3 beds
1 bath
May 25, 2026 - Source: redfin.com
New
6 days ago
1404 Clay St, Winter Park, FL 32789
$2,800
1440 sqft
3 beds
2 baths
May 25, 2026 - Source: zillow.com +3 more
New
7 days ago
2344 Woodcrest Dr, Winter Park, FL 32792
$4,100
1764 sqft
4 beds
2 baths
May 25, 2026 - Source: realtor.com +1 more
New
7 days ago
1846 Barker Dr, Winter Park, FL 32789
$3,900
1680 sqft
4 beds
2 baths
May 25, 2026 - Source: zillow.com +1 more
New
7 days ago
2000 Village Ln, Winter Park, FL 32792
$1,232
545 sqft
1 bed
1 bath
May 23, 2026 - Source: redfin.com
New
9 days ago
1026 S Lakemont Ave, Winter Park, FL 32792
$4,100
1470 sqft
3 beds
2 baths
May 22, 2026 - Source: redfin.com
New
10 days ago
443 Beloit Ave, Winter Park, FL 32789
$6,800
2964 sqft
3 beds
3 baths
May 20, 2026 - Source: redfin.com
New
11 days ago
1077 Minnesota Ave, Winter Park, FL 32789
$7,500
3046 sqft
4 beds
4 baths
May 20, 2026 - Source: realtor.com
New
12 days ago
2024 Lake Dr, Winter Park, FL 32789
$14,000
4027 sqft
3 beds
May 20, 2026 - Source: realtor.com +1 more
New
12 days ago
223 Sandlewood Trl, Winter Park, FL 32789
$2,800
1132 sqft
3 beds
4 baths
May 19, 2026 - Source: realtor.com
New
12 days ago
What's the average rent in Winter Park, FL?
Based on the last 30 days, the average rent in Winter Park, FL is $3,854.
This is 31.7% higher than the average rental price in Florida.
This is 31.7% higher than the average rental price in Florida.
How often do new rentals come on the market in Winter Park, FL?
On average, 1 rentals are put on the market in Winter Park, FL per day.
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