Gated Apartments for Rent in Winter Park, FL (55 Rentals)

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

Why fight Orlando's tourist traffic when you don't have to? Explore the best cities surrounding Orlando for renters, with expert tips on commuting, lifestyle, hidden costs, and where to find the most value.

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Atlas at Winter Park
$1,464 - $1,880
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Total Monthly Price

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$1,464 - $1,880
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1 to 3 Bedroom Apartments Available Now

Atlas at Winter Park

3733 N Goldenrod RdWinter Park, FL 32792
Family Friendly
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Park West Condominiums
Studio Apartments

Park West Condominiums

200-300 Carolina AveWinter Park, FL 32789
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Gables Baldwin Park
Rent Specials
$2,230 - $8,062
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$2,230 - $8,062
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Gables Baldwin Park

2050 Jake StOrlando, FL 32814
Student Housing
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Inscribe Apartments
Rent Specials
$1,679 - $2,718
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$1,679 - $2,718
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Inscribe Apartments

110 Zora PlOrlando, FL 32810
Student Housing
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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Baldwin Harbor
$2,210 - $4,822
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$2,210 - $4,822
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Baldwin Harbor

1771-1887 Jake StOrlando, FL 32814
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The Soul of the City Beautiful: What Life in Orlando Is Really Like

Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.

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400 North
$2,353 - $3,838
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$2,353 - $3,838
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2 to 3 Bedroom Apartments Available Now

400 North

400 N Orlando AveMaitland, FL 32751
Luxury
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Vida at Health Village
Rent Specials
$1,702 - $6,876
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$1,702 - $6,876
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Vida at Health Village

2680 N Orange AveOrlando, FL 32804
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Aurora on the Trail
$1,700 - $3,266
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$1,700 - $3,266
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$1,700 - $3,266
Studio to 3 Bedroom Apartments Available Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
Corporate Housing
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Top Neighborhoods Near Orlando Major Employers

Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

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Audubon Park
$1,737 - $3,659
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$1,737 - $3,659
Total Monthly Price
$1,737 - $3,659
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
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property at 1521 Legacy Club Dr

$1,700

Total Monthly Price

Total Monthly Price

Base Rent
$1,700
Total Monthly Price
$1,700

1 Bedroom, 1 Bath Townhome for Rent

Available Now

1521 Legacy Club Dr

MaitlandFL32751
property at 860 N Orange Ave

$1,850

Total Monthly Price

Total Monthly Price

Base Rent
$1,850
Total Monthly Price
$1,850

1 Bedroom, 1 Bath Condo for Rent

Available Aug 21

860 N Orange Ave, Unit 268

860 N Orange Ave
OrlandoFL32801

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Winter Park, FL Local Guide

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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com

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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Winter Park Overview

Winter Park, Florida offers something for everyone. This suburban city of over 29,000 people provides historical, cultural, and recreational opportunities. Well-known for its museums, art galleries, and parks, the town is home to Rollins College. Outdoor enthusiasts can enjoy water activities at nearby lakes, or explore local hiking and biking trails. With plenty of options for apartments in Winter Park, find a new home here is easy.

Why live in Winter Park, FL?

If you're unsure about relocating to Winter Park apartments, consider all it has to offer. Its convenient location just northeast of Orlando allows you to reap the benefits of living near a sizeable city while enjoying the amenities of a smaller community. Winter Park apartments provide an impressive selection of housing options. This suburban hamlet offers upscale shopping and dining. A local chain of lakes provides ample opportunities for fishing, swimming, and boating. Rollins College and other post-secondary institutions offer educational opportunities in everything from liberal arts to fine arts. Cultural events and a thriving community center bring residents together.

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winter Park, FL Rentals by Map

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See the most popular apartments and homes in Winter Park, FL

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Frequently Asked Questions about Gated Winter Park Apartments

What is the Cheapest Gated apartment in Winter Park?

Currently the most affordable Gated Apartment in Winter Park is at District On Baldwin Park listed at $1,000.

How much is the average rent for a Gated Winter Park Apartment?

The average rent for a Gated Apartment in Winter Park is $2,679.

What is the largest Gated Winter Park Apartment for rent?

Today's Gated apartment with the most square footage in Winter Park is a 3,513 square feet unit starting from $1,937 at Lake House.

What is the average size for Winter Park Gated Apartments for rent?

The average size for a Gated rental in Winter Park is currently at 671 sq ft.

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

Written by: Darla Ferrara

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

Written by: Darla Ferrara

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.

decorative image for Your Guide to the Perfect Orlando Neighborhood for Student Renters article

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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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.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.