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from $1,4041 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 (7 Rentals)
Search the lowest-cost Apartments available for rent right now in the Downtown Winter Park area of Winter Park.
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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from $1,5001 to 3 Bedroom Apartments Available Now
Hannibal Square
433 W New England AveWinter Park, FL 32789
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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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.
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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
1436 Minnesota Ave
Winter ParkFL32789
151 N Orlando Ave
Winter ParkFL32789
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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 | $2,541 | $1,649 | $4,726 |
| Downtown Winter Park 1 Bedroom Apartments | $2,248 | $1,404 | $3,886 |
| Downtown Winter Park 2 Bedroom Apartments | $3,015 | $1,500 | $4,793 |
| Downtown Winter Park 3 Bedroom Apartments | $3,630 | $1,995 | $7,163 |
Browse Apartments in this Neighborhood
There are currently 7 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 2 Beds unit found at Hannibal Square priced from $1,500. The Lofts of Winter Park Village has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,625. 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 Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $1,625 |
| Vida at Health Village | S1 | Studio,1BA | $1,649 |
Best Value Apartments for Rent in Downtown Winter Park, FL
As of May 11, 2025 the best value apartment in the Downtown Winter Park area is the $2.06 price per square foot A4 Model at The Village at Lake Lily in the in the Courtland Street neighborhood starting from $1,733. The second greatest value Downtown Winter Park apartment is the A2 Model at Bainbridge Winter Park starting at $2,007 with a $2.39 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. |
|---|---|---|---|
| The Village at Lake Lily | A4 | 1BR,1BA | $2.06 |
| Bainbridge Winter Park | A2 | 1BR,1BA | $2.39 |
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $2.03 |
| Paseo at Winter Park Village | Bulevar | 1BR,1BA | $2.83 |
| Azul Baldwin Park | A2 | 1BR,1BA | $2.46 |
| The Adeline | A4 | 1BR,1BA | $2.51 |
| Maitland City Centre | A1 | 1BR,1BA | $2.45 |
| Hannibal Square | 402 1BD | 1BR,1BA | $2.70 |
| Juno Winter Park | Flora | Studio ,1BA | $2.69 |
| Vida at Health Village | S1 | Studio ,1BA | $2.59 |
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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 $1,649.
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 $1,625 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 $1,500 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 $2,359.
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.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.
Navigating the Rental Market: Tips for First-Time Renters
Written by: Sandy Baker
Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.