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The average rent in Winter Park, as of July 2026, is down 7.01% compared to last month and down 11.69% year-over-year.
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1d ago
Verified
3935 Sutton Place Blvd, Winter Park, FL 32792
In-unit laundry | On-site laundry | Swimming pool
1–2 beds
1–2 baths
$1,351–$3,058
Price drop
Apartment for rent
4d ago
Verified
7000 University Blvd, Winter Park, FL 32792
Air conditioning | On-site laundry | Swimming pool
1–3 beds
1–2 baths
$1,215–$1,665
Apartment for rent
13h ago
Verified
1–3 beds
1–2 baths
$1,214–$2,155
Price drop
Apartment for rent
Available Sep 9
20h ago
Verified
600 N Semoran Blvd, Winter Park, FL 32792
Swimming pool | Fitness center | Business center
1–2 beds
1–2 baths
$1,095–$1,295
Apartment for rent
1d ago
Verified
1–2 beds
1–2 baths
$1,275–$1,745
Apartment for rent
14h ago
Condo for rent in Winter Park
In-unit laundry | Swimming pool | Dishwasher
2 beds
1 bath
$1,595
Condo for rent
5d+ ago
House for rent in Winter Park
3 beds
1 bath
$2,395
House for rent
2d ago
Verified
3 beds
2.5 baths
$2,450
House for rent
Available Jul 30
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5d+ ago
Verified
223 Sandlewood Trl #223, Winter Park, FL 32789
In-unit laundry | Air conditioning | Balcony
3 beds
3.5 baths
$2,950
Condo for rent
Available Jul 1
17h ago
Verified
2661 Tierra Cir, Winter Park, FL 32792
Garage parking | Outdoor space
3 beds
2 baths
$2,675
House for rent
Available Jul 23
Swimming Pool
Outdoor Space
In-Unit Laundry
Dishwasher
1d ago
Verified
3 beds
1 bath
$2,595
$2,275
Price drop
House for rent
Available Jun 17
5d+ ago
Verified
2313 Dunbury Ct, Winter Park, FL 32792
Garage parking | Outdoor space
3 beds
2 baths
$2,395
House for rent
Available May 21
5d+ ago
Verified
1695 Lee Rd #C210, Winter Park, FL 32789
In-unit laundry | Air conditioning | On-site laundry
1 bed
1 bath
$1,200
Condo for rent
Available Jul 1
5d+ ago
Verified
1695 Lee Rd #E107, Winter Park, FL 32789
In-unit laundry | Air conditioning | Balcony
1 bed
1 bath
$1,300
Apartment for rent
Available May 1
1m ago
Condo for rent in Winter Park
2 beds
2 baths
$1,800
Condo for rent
1h ago
3207 Rosebud Ln, Winter Park, FL 32792
In-unit laundry | Furnished | On-site laundry
1–2 beds
1–2 baths
$1,361–$2,309
Price drop
Apartment for rent
1d ago
349 Scottsdale Sq, Winter Park, FL 32792
In-unit laundry | Air conditioning | On-site laundry
1–3 beds
1–2 baths
$1,088–$2,325
Price drop
Apartment for rent
1d ago
2000 Village Ln, Winter Park, FL 32792
Air conditioning | On-site laundry | Swimming pool
1–2 beds
1–2 baths
$1,246–$1,824
Apartment for rent
2d ago
3656 N Goldenrod Rd, Winter Park, FL 32792
On-site laundry | Swimming pool | Dishwasher
1 bed
1 bath
$1,599
Apartment for rent
5d+ ago
Golfside condo for rent in Winter Park
1000 S Semoran Blvd #806, Winter Park, FL 32792
In-unit laundry | Air conditioning | On-site laundry
2 beds
2 baths
$1,385
Condo for rent
Available Apr 13
5d+ ago
Condo for rent in Winter Park
2 beds
2 baths
$1,450
Condo for rent
5d+ ago
Golfside condo for rent in Winter Park
1 bed
1 bath
$1,299
Condo for rent
15h ago
House for rent in Winter Park
3 beds
3 baths
$3,795
House for rent
18h ago
House for rent in Winter Park
2 beds
2.5 baths
$1,750
House for rent
19h ago
3040 Aloma Avenue, Winter Park, FL 32792
Air conditioning | On-site laundry | Balcony
1–2 beds
1–2 baths
$1,450–$1,625
Apartment for rent
Available Jun 7
1d ago
House for rent in Winter Park
5321 Cypress Reserve Pl #NA, Winter Park, FL 32792
In-unit laundry | Air conditioning | Garage parking
4 beds
2 baths
$4,500
House for rent
Available Sep 1
1d ago
Condo for rent in Winter Park
1 bed
1 bath
$1,175
Condo for rent
Available Jul 10
1d ago
Apartment for rent in Winter Park
3 beds
2 baths
$2,745
Apartment for rent
Available Jul 12
1d ago
Apartment for rent in Winter Park
In-unit laundry | Fitness center | Elevator
1 bed
1 bath
$1,715
Apartment for rent
Available Jul 13
1d ago
Condo for rent in Winter Park
2 beds
2 baths
$1,650
Condo for rent
1d ago
House for rent in Winter Park
3 beds
2 baths
$2,500
$2,400
Price drop
House for rent
2d ago
House for rent in Winter Park
3 beds
3.5 baths
$8,500
House for rent
2d ago
House for rent in Winter Park
1871 Casselwood St #1, Winter Park, FL 32792
Air conditioning | Garage parking | On-site laundry
3 beds
2.5 baths
$2,595
House for rent
Available Jul 13
3d ago
2015 New Stonecastle Ter, Winter Park, FL 32792
In-unit laundry | Air conditioning | Garage parking
1–2 beds
1–2 baths
$1,441–$2,437
Apartment for rent
4d ago
2001 Glenridge Way, Winter Park, FL 32792
Air conditioning | On-site laundry | Swimming pool
2 beds
1 bath
$1,899
Apartment for rent
5d+ ago
Apartment for rent in Winter Park
1 bed
1 bath
$1,997
Apartment for rent
5d+ ago
House for rent in Winter Park
3 beds
2 baths
$1,995
House for rent
Available Jul 9
5d+ ago
House for rent in Winter Park
4 beds
3.5 baths
$6,495
House for rent
5d+ ago
House for rent in Winter Park
6 beds
5 baths
$6,500
$5,950
Price drop
House for rent
Available Jun 18
5d+ ago
House for rent in Winter Park
3 beds
2.5 baths
$1,665
House for rent
5d+ ago
Condo for rent in Winter Park
1 bed
1 bath
$1,400
Condo for rent
Available Jul 10
5d+ ago
Apartment for rent in Winter Park
955 Aragon Ave #A, Winter Park, FL 32789
In-unit laundry | Air conditioning | Assigned parking
2 beds
2 baths
$2,200
Apartment for rent
Available Aug 1
5d+ ago
House for rent in Winter Park
2 beds
2 baths
$1,400
$1,300
Price drop
House for rent
5d+ ago
House for rent in Winter Park
1 bed
1 bath
$1,349
House for rent
Available Jun 10
5d+ ago
Condo for rent in Winter Park
1250 S Denning Dr, Winter Park, FL 32789
In-unit laundry | On-site laundry | Swimming pool
2 beds
2 baths
$2,000
Condo for rent
Available Aug 4
5d+ ago
Condo for rent in Winter Park
1 bed
1 bath
$1,499
Condo for rent
5d+ ago
House for rent in Winter Park
3 beds
2.5 baths
$3,499
House for rent
5d+ ago
Townhouse for rent in Winter Park
836 Miles Ave, Winter Park, FL 32789
In-unit laundry | Air conditioning | Garage parking
2 beds
1.5 baths
$2,200
House for rent
5d+ ago
Condo for rent in Winter Park
2 beds
2 baths
$2,400
Condo for rent
5d+ ago
Townhouse for rent in Winter Park
3 beds
2.5 baths
$2,325
House for rent
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28 rentals
2,450 rentals
70 rentals
25 rentals
11 rentals
14 rentals
20 rentals
1 rental
9 rentals
2 rentals
Winter Park, FL, offers a blend of beautiful parks and lakes, making it a pleasant place for outdoor activities like jogging and biking. Residents appreciate the vibrant local arts scene, with frequent events and galleries to explore. The area is noted for its excellent schools, which is a significant draw for families. However, some locals mention frustrations with traffic and parking, especially around the popular Park Avenue shopping district, where congestion can be a hassle during peak times.
Winter Park's 2025 rental market shows one-bedroom apartments averaging around $1,400 per month, while two-bedroom units average around $1,700 monthly. Both apartment types experienced year-over-year decreases, with one-bedrooms declining 6.1% and two-bedrooms dropping 4.4% from 2024 levels.
October stands out as the optimal month for apartment hunting in Winter Park, offering both the lowest seasonal rents and reduced competition among renters. The city sees an 8% difference between peak July pricing and October's off-peak rates, making fall timing particularly advantageous for budget-conscious searches.
Winter Park offers solid options for pet owners, with 48% of rental listings welcoming pets. This represents a substantial portion of the city's average 258 monthly apartment listings, providing pet owners with multiple housing choices across different property types.
Utilities are rarely included in Winter Park rental agreements, appearing in less than 1% of total listings. Among the limited options, one-bedroom apartments show the highest rate at 0.08% of listings, while studios currently show no utility-included options available.
Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.
Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.
Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.
| 🔑Available apartment rentals | 257 |
|---|---|
| 💰Best rent deal | 349 Scottsdale Sq |
| ✨Popular amenities | , , |
| 🧦In-unit laundry | |
| 🍽With dishwasher | |
| 🏠With photos |