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from $1,5001 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 $1,6251 Bedroom Apartments Available Now
The Lofts of Winter Park Village
520 N Orlando AveWinter Park, FL 32789
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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.
1436 Minnesota Ave
Winter ParkFL32789
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from $1,5171 to 3 Bedroom Apartments Available Now
The Village at Lake Lily
925 S Orlando AveMaitland, FL 32751
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Rent Specials
from $1,694Studio to 3 Bedroom Apartments Available Now
Vida at Health Village
2680 N Orange AveOrlando, FL 32804
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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 | $2,606 | $1,694 | $5,138 |
| Downtown Winter Park 1 Bedroom Apartments | $2,407 | $1,502 | $4,236 |
| Downtown Winter Park 2 Bedroom Apartments | $3,084 | $1,500 | $4,897 |
| Downtown Winter Park 3 Bedroom Apartments | $3,891 | $2,350 | $7,190 |
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
- Nearby Winter Park neighborhoods
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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 2 Beds unit found at Hannibal Square priced from $1,500. The Village at Lake Lily has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,517. Here are the most affordable Downtown Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Hannibal Square | 400 2x1 | 2BR,1BA | $1,500 |
| The Village at Lake Lily | A3 | 1BR,1BA | $1,517 |
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $1,625 |
Best Value Apartments for Rent in Downtown Winter Park, FL
As of April 23, 2025 the best value apartment in the Downtown Winter Park area is the $2.56 price per square foot Risa Model at Paseo at Winter Park Village in the in the North Orange neighborhood starting from $2,755. The second greatest value Downtown Winter Park apartment is the Formosa Model at The Ivy Residences at Health Village Apartment Homes starting at $2,078 with a $2.40 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. |
|---|---|---|---|
| Paseo at Winter Park Village | Risa | 2BR,2BA | $2.56 |
| The Ivy Residences at Health Village Apartment Homes | Formosa | 1BR,1BA | $2.40 |
| The Village at Lake Lily | A4 | 1BR,1BA | $2.18 |
| Maitland City Centre | A4 | 1BR,1BA | $2.43 |
| Vida at Health Village | A9 | 1BR,1BA | $2.75 |
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $2.03 |
| Azul Baldwin Park | A2 | 1BR,1BA | $2.54 |
| The Adeline | A1 | 1BR,1BA | $2.54 |
| Hannibal Square | 402 1BD | 1BR,1BA | $2.70 |
| Bainbridge Winter Park | J1 | 1BR,1BA | $2.90 |
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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 Vida at Health Village listed at $1,694.
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 $1,517 at The Village at Lake Lily.
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 $1,500 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 $2,355.
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 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.
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.
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.