
Apartments for Rent in Winter Park, FL Under $4,400 (382 Rentals) Page 3 of 8


3050 Autumn Ct

731 W Comstock Ave

303 Sandlewood Trail

7290 Daniel Webster Dr

1500 Gay Rd, Unit 9D, Unit 9D

7473 Belle River Ct

205 Lewfield Cir

612 Trinidad Ct

2304 Inagua Way

3254 Howell Branch Rd

7429 Daniel Webster Dr

3283 Oak Lake Pl

4968 Tangerine Ave

3011 George Mason Ave

625 Trinidad Ct

700 Melrose Ave

2936 Antique Oaks Cir

2523 Alexa Ct

3012 Patel Dr

2911 Antique Oaks Cir

105 Jergo Rd

1500 Gay Rd, Unit 1D, Unit 1D

7340 Swallow Run

1565 Michigan Ave

2500 Lee Rd

1000 S Semoran Blvd

2500 Lee Rd, Unit 244, Unit 244

1555 Michigan Ave

3651 Goldenrod Rd

3032 Antique Oaks Cir

1695 Lee Rd

3651 N Goldenrod Rd

4818 Tangerine Ave

5319 N Orange Ave

2942 Antique Oaks Cir, Unit 82

138 Lewfield Cir

3075 Aaron Burr Ave

525 S Lakemont Ave

5058 Seminole Ave, Unit Seminole Unit 1, Unit Seminole Unit 1

The Fisher

Tuscany Villas of Winter Park

Whisper Lake Apartments

Goldenrod Pointe

Park Apartments

Venue At Winter Park

Sun Bay Apartments

Indigo Winter Park

Serena Winter Park

Sovereignty at Winter Park Apartments
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.