Gated Apartments for Rent in Winter Park, FL Under $2,000 (45 Rentals)

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Juno Winter Park
Rent Specials
$1,564 - $4,621
Total Monthly Price

Total Monthly Price

Base Rent
$1,447 - $4,504
Required Monthly Fees
$117
Total Monthly Price
$1,564 - $4,621
Studio to 3 Bedroom Apartments Available Now

Juno Winter Park

1305 Morgan Stanley AveWinter Park, FL 32789
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The Lofts of Winter Park Village
$1,555 - $2,175
Total Monthly Price

Total Monthly Price

Base Rent
$1,545 - $2,165
Required Monthly Fees
$10
Total Monthly Price
$1,555 - $2,175
1 Bedroom Apartments Available Now

The Lofts of Winter Park Village

520 N Orlando AveWinter Park, FL 32789
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Atlas at Winter Park
$1,431 - $1,661
Total Monthly Price

Total Monthly Price

Base Rent
$1,396 - $1,626
Required Monthly Fees
$35
Total Monthly Price
$1,431 - $1,661
1 to 3 Bedroom Apartments Available Now

Atlas at Winter Park

3733 N Goldenrod RdWinter Park, FL 32792
Family Friendly
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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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Solis at Winter Park
$1,271 - $1,506
Total Monthly Price

Total Monthly Price

Base Rent
$1,138 - $1,373
Required Monthly Fees
$133
Total Monthly Price
$1,271 - $1,506
1 to 2 Bedroom Apartments Available Now

Solis at Winter Park

7502 Sun Key BlvdWinter Park, FL 32792
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ARIUM Winter Park
$1,269 - $2,818
Total Monthly Price

Total Monthly Price

Base Rent
$1,007 - $2,556
Required Monthly Fees
$262
Total Monthly Price
$1,269 - $2,818
1 to 2 Bedroom Apartments Available Now

ARIUM Winter Park

3250 Bishop Park DrWinter Park, FL 32792
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Seabrook
Rent Specials
$1,181 - $1,763
Total Monthly Price

Total Monthly Price

Base Rent
$1,021 - $1,603
Required Monthly Fees
$160
Total Monthly Price
$1,181 - $1,763
1 to 2 Bedroom Apartments Available Now

Seabrook

3114 Terry Brook DrWinter Park, FL 32792
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The Yard at Ivanhoe
$1,898 - $3,688
Total Monthly Price

Total Monthly Price

Base Rent
$1,866 - $3,656
Required Monthly Fees
$32
Total Monthly Price
$1,898 - $3,688
1 to 3 Bedroom Apartments Available Now

The Yard at Ivanhoe

1460 Alden RdOrlando, FL 32803
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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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Baldwin Harbor
$1,887 - $5,817
Total Monthly Price

Total Monthly Price

Base Rent
$1,830 - $5,760
Required Monthly Fees
$57
Total Monthly Price
$1,887 - $5,817
1 to 3 Bedroom Apartments Available Now

Baldwin Harbor

1771-1887 Jake StOrlando, FL 32814
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Inscribe Apartments
Rent Specials
$1,725 - $2,836
Total Monthly Price

Total Monthly Price

Base Rent
$1,645 - $2,756
Required Monthly Fees
$80
Total Monthly Price
$1,725 - $2,836
1 to 3 Bedroom Apartments Available Now

Inscribe Apartments

110 Zora PlOrlando, FL 32810
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The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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Vida at Health Village
Rent Specials
$1,679 - $9,822
Total Monthly Price

Total Monthly Price

Base Rent
$1,591 - $9,734
Required Monthly Fees
$88
Total Monthly Price
$1,679 - $9,822
Studio to 3 Bedroom Apartments Available Now

Vida at Health Village

2680 N Orange AveOrlando, FL 32804
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The Village at Lake Lily
Rent Specials
$1,664 - $7,021
Total Monthly Price

Total Monthly Price

Base Rent
$1,611 - $6,968
Required Monthly Fees
$53
Total Monthly Price
$1,664 - $7,021
1 to 3 Bedroom Apartments Available Now

The Village at Lake Lily

925 S Orlando AveMaitland, FL 32751
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Aurora on the Trail
$1,599 - $3,352
Total Monthly Price

Total Monthly Price

Base Rent
$1,524 - $3,277
Required Monthly Fees
$75
Total Monthly Price
$1,599 - $3,352
Studio to 3 Bedroom Apartments Available Now

Aurora on the Trail

825 McCullough AveOrlando, FL 32803
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Audubon Park
$1,593 - $3,004
Total Monthly Price

Total Monthly Price

Base Rent
$1,563 - $2,974
Required Monthly Fees
$30
Total Monthly Price
$1,593 - $3,004
1 to 3 Bedroom Apartments Available Now

Audubon Park

990 Warehouse RdOrlando, FL 32803
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The Gallery at Mills Park
Rent Specials
$1,581 - $2,768
Total Monthly Price

Total Monthly Price

Base Rent
$1,527 - $2,714
Required Monthly Fees
$54
Total Monthly Price
$1,581 - $2,768
Studio to 3 Bedroom Apartments Available Now

The Gallery at Mills Park

1650 N Mills AveOrlando, FL 32803
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The Baldwin
Rent Specials
$1,552 - $2,524
Total Monthly Price

Total Monthly Price

Base Rent
$1,452 - $2,424
Required Monthly Fees
$100
Total Monthly Price
$1,552 - $2,524
1 to 3 Bedroom Apartments Available Now

The Baldwin

800 Lombard StOrlando, FL 32807
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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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Steelhouse Orlando
Rent Specials
$1,474 - $2,715
Total Monthly Price

Total Monthly Price

Base Rent
$1,362 - $2,603
Required Monthly Fees
$112
Total Monthly Price
$1,474 - $2,715
1 to 2 Bedroom Apartments Available Now

Steelhouse Orlando

750 N Orange AveOrlando, FL 32801
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911 N Orange Ave
Studio to 3 Bedroom Apartments

911 N Orange Ave

911 N Orange AveOrlando, FL 32801
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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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Winter Park, FL Local Guide

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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

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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 $2,543.

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 $2,074 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 654 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

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent

Written by: Darla Ferrara

For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.

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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.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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

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.

Articles, How-To's, and Tips

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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.