1555 Michigan Ave
Winter ParkFL32789
Cheap Homes for Rent in Downtown Winter Park Neighborhood of Winter Park, FL from $1,400 (4 Rentals)
Search the lowest-cost Homes available for rent right now in the Downtown Winter Park area of Winter Park.
151 N Orlando Ave
Winter ParkFL32789
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
700 Melrose Ave
Winter ParkFL32789
1500 Gay Rd, Unit 9D, Unit 9D
1500 Gay Rd
Winter ParkFL32789
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
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Downtown Winter Park, Winter Park, FL Local Guide
How much does it cost to rent a home in Downtown Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Downtown Winter Park 2 Bedroom Homes for Rent | $2,533 | $1,850 | $3,200 |
| Downtown Winter Park 3 Bedroom Homes for Rent | $3,548 | $1,950 | $5,500 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 4 rentals with your search options within a 1 mile radius of the Downtown Winter Park Neighborhood of Winter Park, FL.
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Best Value Apartments for Rent in Downtown Winter Park, FL
As of May 21, 2026 the best value apartment in the Downtown Winter Park area is the $2.49 price per square foot A2 Model at Bainbridge Winter Park in the in the Courtland Street neighborhood starting from $2,088. The second greatest value Downtown Winter Park apartment is the ELBB Model at The Lofts of Winter Park Village starting at $1,675 with a $2.21 price per square foot in the North Orange neighborhood. Here is today’s list of the best values for Downtown Winter Park apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Bainbridge Winter Park | A2 | 1BR,1BA | $2.49 |
| The Lofts of Winter Park Village | ELBB | 1BR,1BA | $2.21 |
| Paseo at Winter Park Village | Bulevar | 1BR,1BA | $2.44 |
| Elon Winter Park | The Tony | 1BR,1BA | $2.19 |
| Village Park Senior | Osceola | 1BR,1BA | $2.56 |
| Juno Winter Park | Luna | Studio ,1BA | $3.24 |
| Hannibal Square | 433 W. New England Ave./ Front/3rd Fl/ Front | Studio ,1BA | $3.74 |
Frequently Asked Questions about Downtown Winter Park
What type of rentals are currently available in Downtown Winter Park?
There are currently 57 Apartments for Rent in Downtown Winter Park, FL with pricing that ranges from $1,330 to $3,944. There are also 15 Single Family Homes for rent, Condos, and Townhome rentals currently available in Downtown Winter Park ranging from $1,450 to $5,500.
What is the current price range for Rental Homes in Downtown Winter Park?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Downtown Winter Park ranges from $1,450 to $5,500 with an average monthly rent of $2,538.
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.
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An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent
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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
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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
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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
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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.