Apartments for Rent in Winter Park, FL (609 Rentals) Page 4 of 13

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property at 5462 Bracken Ct

$1,695

Total Monthly Price

Total Monthly Price

Base Rent
$1,695
Total Monthly Price
$1,695

2 Bedroom, 3 Bath Townhome for Rent

Available Now

5462 Bracken Ct

Winter ParkFL32792
property at 1720 Miller Ave

$1,775

Total Monthly Price

Total Monthly Price

Base Rent
$1,775
Total Monthly Price
$1,775

2 Bedroom, 1 Bath Home for Rent

Available Now

1720 Miller Ave

Winter ParkFL32789
property at 1500 Gay Rd

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900
Total Monthly Price
$1,900

2 Bedroom, 2 Bath Condo for Rent

Available Now

1500 Gay Rd, Unit 25B

1500 Gay Rd
Winter ParkFL32789
property at 524 N Lakemont Ave

$2,300

Total Monthly Price

Total Monthly Price

Base Rent
$2,300
Total Monthly Price
$2,300

3 Bedroom, 2 Bath Home for Rent

Available Now

524 N Lakemont Ave

Winter ParkFL32792
property at 3606 Leanne Ct

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800
Total Monthly Price
$1,800

3 Bedroom, 2 Bath Home for Rent

Available Now

3606 Leanne Ct

Winter ParkFL32792
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Advenir at Magnolia
Rent Specials
$1,134 - $1,769
Total Monthly Price

Total Monthly Price

Base Rent
$1,134 - $1,769
Total Monthly Price
$1,134 - $1,769
Studio to 2 Bedroom Apartments Available Now

Advenir at Magnolia

210 Welcome WayFern Park, FL 32730
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Gables Baldwin Park
Rent Specials
$2,273 - $6,200
Total Monthly Price

Total Monthly Price

Base Rent
$2,273 - $6,200
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Gables Baldwin Park

2050 Jake StOrlando, FL 32814
Student Housing
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Inscribe Apartments
Rent Specials
$1,669 - $2,948
Total Monthly Price

Total Monthly Price

Base Rent
$1,669 - $2,948
Total Monthly Price
Varies
1 to 3 Bedroom Apartments Available Now

Inscribe Apartments

110 Zora PlOrlando, FL 32810
Student Housing
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The Adeline
$1,726 - $3,150
Total Monthly Price

Total Monthly Price

Base Rent
$1,726 - $3,150
Total Monthly Price
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1 to 3 Bedroom Apartments Available Now

The Adeline

304 Lake AveMaitland, FL 32751
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Cortland Lake Howell
Rent Specials
$1,604 - $3,569
Total Monthly Price

Total Monthly Price

Base Rent
$1,604 - $3,569
Total Monthly Price
Varies
1 to 3 Bedroom Apartments Available Now

Cortland Lake Howell

1280 Vinings LnCasselberry, FL 32707
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Baldwin Harbor
$1,958 - $5,002
Total Monthly Price

Total Monthly Price

Base Rent
$1,958 - $5,002
Total Monthly Price
Varies
1 to 3 Bedroom Apartments Available Now

Baldwin Harbor

1771-1887 Jake StOrlando, FL 32814
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400 North
$1,921 - $2,531
Total Monthly Price

Total Monthly Price

Base Rent
$1,921 - $2,531
Total Monthly Price
Varies
1 to 3 Bedroom Apartments Available Sep 14

400 North

400 N Orlando AveMaitland, FL 32751
Luxury
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Vida at Health Village
Rent Specials
$1,772 - $5,402
Total Monthly Price

Total Monthly Price

Base Rent
$1,772 - $5,402
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Vida at Health Village

2680 N Orange AveOrlando, FL 32804
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Aurora on the Trail
$1,520 - $3,177
Total Monthly Price

Total Monthly Price

Base Rent
$1,520 - $3,177
Total Monthly Price
$1,520 - $3,177
Studio to 3 Bedroom Apartments Available Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
Corporate Housing
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Showing Results 151-200, Page 4 of 13

Frequently Asked Questions about Winter Park

What is the current pricing and availability for apartments for rent in Winter Park, FL?

As of today, September 02, 2026, there are currently 609 available Winter Park apartments priced from $529 to $6,500, with an average monthly rent of $2,032.

What Winter Park neighborhoods have the most available apartments?

There are 7 neighborhoods in the Winter Park area with available listings as of today. The three neighborhoods with the most options are I Drive Orlando with 1,105 listings, North Orlando with 817 listings, and East Orlando with 427 listings.

How much are Studio apartments in Winter Park?

There are currently 92 Studio Apartments in Winter Park with rent ranges from $900 to $2,790 with an average price of $1,596.

What is the current price range for One Bedroom Winter Park Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winter Park ranges from $529 to $3,880 with an average monthly rent of $1,794.

What does renting a Two Bedroom Apartment in Winter Park cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winter Park range from $645 to $4,105. Today's average rental price for Two Bedrooms here is $2,161.

How expensive are Winter Park Three Bedroom Apartments?

There are currently 106 Three Bedroom Apartments listings available in Winter Park on ApartmentHomeLiving.com. The pricing ranges from $750 to $6,500 - averaging $2,583 for the location.

Expert Rental Resources

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

Helpful Local Expert Guides

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Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities

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When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

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The Soul of the City Beautiful: What Life in Orlando Is Really Like

Written by: Darla Ferrara

When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.

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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers

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When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Written by: Darla Ferrara

There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

Articles, How-To's, and Tips

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.