
Apartments near Lakeside Crossing in Winter Park, FL (175 Rentals)


Lake Maitland Terrace Condos

Howard Atha House Apartments

Gem Lake Apartments

Dubsdread Apartments

Maitland Shores

West Cove Condominiums

386 Lime St

17 W Hazel St

143 S College Ave

Smith Street Condo

3705 Edgewater Dr

118 Eaton St

114 Eaton St

1012 Webster Ave

Colonial Apartments

713 Rugby St

2305 Edgewater Dr

Meadows at Margaret Square

La Bella Vida

The Oaks Apartments

Bay Run Apartments

The Q at Maitland

Sumerset Apartments

The Carl

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Frequently Asked Questions about Winter Park
How much are Studio apartments in Winter Park?
There are currently 90 Studio Apartments in Winter Park with rent ranges from $900 to $2,790 with an average price of $1,592.
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 $3,789 with an average monthly rent of $1,784.
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 $4,111. Today's average rental price for Two Bedrooms here is $2,167.
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 $2,688 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

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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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.

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.

Your Guide to the Perfect Orlando Neighborhood for Student Renters
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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

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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.

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.

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.