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from $1,1001 to 2 Bedroom Apartments Available Now
Hannibal Square
433 W New England 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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from $1,5081 to 3 Bedroom Apartments Available Now
Bainbridge Winter Park
1400 Morgan Stanley AveWinter Park, FL 32789
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from $1,5501 Bedroom Apartments Available Now
The Lofts of Winter Park Village
520 N Orlando AveWinter Park, FL 32789
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1555 Michigan Ave
Winter ParkFL32789
1565 Michigan Ave
Winter ParkFL32789
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Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla F
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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 | $2,385 | $1,694 | $3,836 |
| Downtown Winter Park 1 Bedroom Apartments | $2,309 | $1,100 | $4,524 |
| Downtown Winter Park 2 Bedroom Apartments | $2,895 | $1,600 | $5,052 |
| Downtown Winter Park 3 Bedroom Apartments | $3,646 | $2,482 | $7,373 |
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.
See all Apartments in Winter ParkExplore Winter Park
Downtown Winter Park, Winter Park, FL Local Guide
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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 The Lofts of Winter Park Village priced from $1,550. Hannibal Square has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,600. Here are the most affordable Downtown Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $1,550 |
| Hannibal Square | 400 2x1 | 2BR,1BA | $1,600 |
| The Village at Lake Lily | A3 | 1BR,1BA | $1,609 |
Best Value Apartments for Rent in Downtown Winter Park, FL
As of March 23, 2025 the best value apartment in the Downtown Winter Park area is the $2.34 price per square foot A1L Model at Bainbridge Winter Park in the in the Courtland Street neighborhood starting from $1,969. The second greatest value Downtown Winter Park apartment is the A4 Model at The Village at Lake Lily starting at $1,817 with a $2.16 price per square foot in the Courtland Street 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 | A1L | 1BR,1BA | $2.34 |
| The Village at Lake Lily | A4 | 1BR,1BA | $2.16 |
| Maitland City Centre | A3 | 1BR,1BA | $2.22 |
| Perla Gem Lake | A2 | 1BR,1BA | $2.58 |
| Vida at Health Village | A9 | 1BR,1BA | $2.71 |
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $1.94 |
| Paseo at Winter Park Village | Bulevar | 1BR,1BA | $2.78 |
| The Adeline | A2 | 1BR,1BA | $2.50 |
| The Ivy Residences at Health Village Apartment Homes | Rowena | 1BR,1BA | $2.47 |
| Hannibal Square | 402 1BD | 1BR,1BA | $3.00 |
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Pet Friendly LifestyleDowntown Winter Park, Winter Park, FL
Ranked #7
Among neighborhoods in Winter Park, FL for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
2.5Pet Friendly
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 $1,600.
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 $1,550 at The Lofts of Winter Park Village.
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 $1,600 at Hannibal Square.
What is the most affordable Downtown Winter Park Three Bedroom Apartment?
The best deal on a cheap Downtown Winter Park Three Bedroom Apartment rental is at The Adeline and starts from $2,482.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent
Written by: Darla F
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.
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.
What to Know About Fees and Fines When Renting
Written by: Trey Huguley
When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process.
Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.