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$1,518 - $3,5811 to 3 Bedroom Apartments Available Now
Bainbridge Winter Park
1400 Morgan Stanley AveWinter Park, FL 32789
Cheap Apartments for Rent in the Downtown Winter Park Neighborhood of Winter Park, FL from $700 (8 Rentals)
Search the lowest-cost Apartments available for rent right now in the Downtown Winter Park area of Winter Park.
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Rent Specials
$1,850 - $8,297Studio to 3 Bedroom Apartments Available Now
Juno Winter Park
1305 Morgan Stanley AveWinter Park, FL 32789
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Rent Specials
$1,549 - $1,6181 Bedroom Apartments Available Now
Elon Winter Park
712 Nicolet AveWinter Park, FL 32789
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$2,027 - $4,3781 to 3 Bedroom Apartments Available Now
Paseo at Winter Park Village
940 W Canton AveWinter Park, FL 32789
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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Rent Specials
$1,330 - $1,575Studio to 2 Bedroom Apartments Available Now
Park East - Park Knowles Apartments
311 N Knowles AveWinter Park, FL 32789
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Rent Specials
$1,575 - $1,7951 Bedroom Apartments Available Now
The Lofts of Winter Park Village
520 N Orlando AveWinter Park, FL 32789
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$1,750 - $2,7502 Bedroom Apartments Available Now
Hannibal Square
433 W New England AveWinter Park, FL 32789
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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.
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Downtown Winter Park, Winter Park, FL Local Guide
How much does it cost to rent an apartment in Downtown Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Downtown Winter Park Studio Apartments | $1,718 | $1,330 | $1,921 |
| Downtown Winter Park 1 Bedroom Apartments | $1,955 | $1,236 | $2,335 |
| Downtown Winter Park 2 Bedroom Apartments | $2,488 | $1,437 | $3,221 |
| Downtown Winter Park 3 Bedroom Apartments | $3,255 | $2,700 | $3,581 |
Browse Apartments in this Neighborhood
There are currently 8 rentals with your search options within a 1 mile radius of the Downtown Winter Park Neighborhood of Winter Park, FL.
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Cheapest Available Downtown Winter Park Apartments for Rent
The cheapest available apartment rental in the Downtown Winter Park area of Orlando, FL is a 1 Bed unit found at Village Park Senior priced from $1,236. Elon Winter Park has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,549. Here are the most affordable Downtown Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Village Park Senior | One Bedroom One Bath | 1BR,1BA | $1,236 |
| Elon Winter Park | The Tony | 1BR,1BA | $1,549 |
| Park East - Park Knowles Apartments | 1 Bedroom, 1 Bathroom | 1BR,1BA | $1,575 |
Best Value Apartments for Rent in Downtown Winter Park, FL
As of January 02, 2026 the best value apartment in the Downtown Winter Park area is the $2.48 price per square foot B1 Model at Bainbridge Winter Park in the in the Courtland Street neighborhood starting from $2,686. The second greatest value Downtown Winter Park apartment is the 1 Bedroom, 1 Bathroom Model at Park East - Park Knowles Apartments starting at $1,575 with a $2.10 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 | B1 | 2BR,2BA | $2.48 |
| Park East - Park Knowles Apartments | 1 Bedroom, 1 Bathroom | 1BR,1BA | $2.10 |
| Hannibal Square | 433 2x1 | 2BR,1BA | $2.36 |
| Paseo at Winter Park Village | Andar | 1BR,1BA | $2.82 |
| Elon Winter Park | The Tony | 1BR,1BA | $2.09 |
| The Lofts of Winter Park Village | ELBB | 1BR,1BA | $2.48 |
| Village Park Senior | Osceola | 1BR,1BA | $2.35 |
| Juno Winter Park | Luna | Studio ,1BA | $3.23 |
Frequently Asked Questions about Cheap Downtown Winter Park Apartments
What is the Cheapest Studio apartment in Downtown Winter Park?
Currently the most affordable Cheap Studio Apartment in Downtown Winter Park is at Juno Winter Park listed at $1,850.
How much is rent for a Cheap One Bedroom Downtown Winter Park Apartment?
The lowest price for a Cheap One Bedroom Downtown Winter Park Apartment is $1,236 at Village Park Senior.
What is the lowest price for a Cheap Two Bedroom Downtown Winter Park Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Downtown Winter Park is starting from $1,437 at Village Park Senior.
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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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.
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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.
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Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!