
Apartments for Rent in Winter Park, FL Under $4,400 (382 Rentals) Page 4 of 8


Sedgefield Apartments

Mizell at Winter Park

Sorrento

Azure Winter Park

Branchwood Apartments

Calvary Tower

Winter Park Oaks

El Cortez Apartments

Tuscany at Aloma

Gables Baldwin Park

Enders Place at Baldwin Park

Perla Gem Lake

Lake House

Total Monthly Price
The Yard at Ivanhoe

Total Monthly Price
29 N Lawsona Blvd, Unit lawsona, Unit lawsona

Azul Baldwin Park

Village at Baldwin Park

Maitland City Centre

MAA Baldwin Park

Total Monthly Price
Baldwin Harbor

400 North

Total Monthly Price
Vida at Health Village

The Parker at Maitland Station Apartments

The Majestic at Downtown Baldwin Park

Azalea Gardens

Citron at The Packing District

The Princeton at College Park

Total Monthly Price
Audubon Park

Total Monthly Price
17 W Winter Park St, Unit #17, Unit #17

Total Monthly Price
Aurora on the Trail

The Adeline

Total Monthly Price
Inscribe Apartments

Bell Trelago

Total Monthly Price
Cortland Lake Howell

The Ivy Residences at Health Village Apartment Homes

Total Monthly Price
The Village at Lake Lily

Luna at Lake Shadow

Total Monthly Price
The Gallery at Mills Park

The Shores at Lake Howell

Evergreen Mills 50

NORA Apartments

The Baldwin

Infinity off Baldwin Park

The Cannery at The Packing District

Lake Ivanhoe Shores Apartments

860 North Orange Avenue, Unit Studio, Unit Studio

The Ivy at Gatehouse

Steelhouse Orlando

Adele Place
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 Under $4400 | $1,661 | $900 | $3,493 |
| Winter Park 1 Bedroom Apartments Under $4400 | $1,815 | $695 | $3,596 |
| Winter Park 2 Bedroom Apartments Under $4400 | $2,217 | $956 | $5,364 |
| Winter Park 3 Bedroom Apartments Under $4400 | $2,774 | $1,082 | $6,500 |
| Winter Park 4 Bedroom Apartments Under $4400 | $2,135 | $1,679 | $3,943 |
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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 $3,493 with an average price of $1,661.
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 $695 to $3,596 with an average monthly rent of $1,815.
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 $956 to $5,364. Today's average rental price for Two Bedrooms here is $2,217.
How expensive are Winter Park Three Bedroom Apartments?
There are currently 101 Three Bedroom Apartments listings available in Winter Park on ApartmentHomeLiving.com. The pricing ranges from $1,082 to $6,500 - averaging $2,774 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

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.