
New Apartments for Rent in Winter Park, FL Under $4,400 (29 Rentals)


Juno Winter Park

Vintage Winter Park Apartments

Berkshire Winter Park

Seven41 Winter Park

Bainbridge Winter Park

Goldenrod Pointe
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

Gables Baldwin Park

Perla Gem Lake

Lake House

Total Monthly Price
The Yard at Ivanhoe

Maitland City Centre

400 North

Total Monthly Price
Vida at Health Village
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.

The Parker at Maitland Station Apartments

Citron at The Packing District

The Princeton at College Park

Total Monthly Price
Aurora on the Trail

The Adeline

Total Monthly Price
Inscribe Apartments

Bell Trelago
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.

Luna at Lake Shadow

The Shores at Lake Howell

Evergreen Mills 50

The Baldwin

The Cannery at The Packing District

Camden North Quarter

The Milk Stacks: Boutique Luxury Living in Downtown Orlando's Milk District
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

Ekos at Lake Shadow
Winter Park, FL Local Guide

How much does it cost to rent an apartment in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park Studio Apartments | $1,661 | $900 | $3,493 |
| Winter Park 1 Bedroom Apartments | $1,815 | $695 | $3,596 |
| Winter Park 2 Bedroom Apartments | $2,217 | $956 | $5,364 |
| Winter Park 3 Bedroom Apartments | $2,774 | $1,082 | $6,500 |
| Winter Park 4 Bedroom Apartments | $2,135 | $1,679 | $3,943 |
Explore Winter Park
Winter Park, FL Local Guide
- Winter Park Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
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
Read ArticleReal 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.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
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.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winter Park, FL Rentals by Map
See the most popular apartments and homes in Winter Park, FL
Frequently Asked Questions about New Winter Park Apartments
What is the Cheapest New apartment in Winter Park?
Currently the most affordable New Apartment in Winter Park is at Bainbridge Winter Park listed at $1,416.
How much is the average rent for a New Winter Park Apartment?
The average rent for a New Apartment in Winter Park is $3,073.
What is the largest New Winter Park Apartment for rent?
Today's New apartment with the most square footage in Winter Park is a 3,513 square feet unit starting from $1,934 at Lake House.
What is the average size for Winter Park New Apartments for rent?
The average size for a New rental in Winter Park is currently at 705 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

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.

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.

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.

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

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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.