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$1,515 - $3,5551 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
$1,900 - $6,3561 to 3 Bedroom Apartments Available Now
Paseo at Winter Park Village
940 W Canton AveWinter Park, FL 32789
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Rent Specials
$1,599 - $1,6201 Bedroom Apartments Available Now
Elon Winter Park
712 Nicolet AveWinter Park, FL 32789
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$1,564 - $4,589
Total Monthly Price
Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,447 - $4,472
Required Monthly Fees
$117
Total Monthly Price
$1,564 - $4,589
Juno Winter Park
1305 Morgan Stanley 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 - $1,750Studio to 2 Bedroom Apartments Available Now
Park East - Park Knowles Apartments
311 N Knowles AveWinter Park, FL 32789
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$1,660 - $1,995
Total Monthly Price
1 Bedroom Apartments Available Feb 23Total Monthly Price
Base Rent
$1,650 - $1,985
Required Monthly Fees
$10
Total Monthly Price
$1,660 - $1,995
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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2 Bedroom Apartments
Douglas Grand at Winter Park
99-141 S New York AveWinter Park, FL 32789
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
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. Park East - Park Knowles Apartments has the second lowest priced unit, which is a Studio apartment currently listed from $1,330. 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 |
| Park East - Park Knowles Apartments | 0 Bedroom, 1 Bathroom | Studio,1BA | $1,330 |
| Juno Winter Park | Luna | Studio,1BA | $1,564 |
Best Value Apartments for Rent in Downtown Winter Park, FL
As of February 21, 2026 the best value apartment in the Downtown Winter Park area is the $2.57 price per square foot C2 Model at Bainbridge Winter Park in the in the Courtland Street neighborhood starting from $3,555. The second greatest value Downtown Winter Park apartment is the 433 2x1 Model at Hannibal Square starting at $1,750 with a $2.36 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 | C2 | 3BR,2BA | $2.57 |
| Hannibal Square | 433 2x1 | 2BR,1BA | $2.36 |
| Paseo at Winter Park Village | Andar | 1BR,1BA | $2.59 |
| Elon Winter Park | The Tony | 1BR,1BA | $2.16 |
| Village Park Senior | Osceola | 1BR,1BA | $2.56 |
| Juno Winter Park | Luna | Studio ,1BA | $2.73 |
| Park East - Park Knowles Apartments | 0 Bedroom, 1 Bathroom | Studio ,1BA | $2.80 |
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.
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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.
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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
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.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
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.