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from $1,4781 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.
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from $1,5001 to 3 Bedroom Apartments Available Now
Hannibal Square
433 W New England AveWinter Park, FL 32789
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The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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151 N Orlando Ave
Winter ParkFL32789
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from $1,5671 to 2 Bedroom Apartments Available Now
Maitland City Centre
160-190 Independence LnMaitland, FL 32751
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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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 | $2,652 | $1,649 | $5,136 |
| Downtown Winter Park 1 Bedroom Apartments | $2,237 | $1,478 | $4,426 |
| Downtown Winter Park 2 Bedroom Apartments | $2,993 | $1,500 | $5,068 |
| Downtown Winter Park 3 Bedroom Apartments | $3,890 | $1,995 | $6,910 |
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.
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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. Maitland City Centre has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,567. 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 |
| Maitland City Centre | A1 | 1BR,1BA | $1,567 |
| 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 May 30, 2025 the best value apartment in the Downtown Winter Park area is the $2.22 price per square foot B1 Model at Maitland City Centre in the in the Courtland Street neighborhood starting from $2,181. The second greatest value Downtown Winter Park apartment is the A4 Model at The Village at Lake Lily starting at $1,708 with a $2.03 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. |
|---|---|---|---|
| Maitland City Centre | B1 | 2BR,2BA | $2.22 |
| The Village at Lake Lily | A4 | 1BR,1BA | $2.03 |
| Bainbridge Winter Park | A2 | 1BR,1BA | $2.50 |
| The Lofts of Winter Park Village | 1BR/1.0BA | 1BR,1BA | $2.03 |
| Paseo at Winter Park Village | Bulevar | 1BR,1BA | $2.76 |
| Elon Winter Park | The Tony | 1BR,1BA | $2.29 |
| Azul Baldwin Park | A2 | 1BR,1BA | $2.48 |
| The Adeline | A1 | 1BR,1BA | $2.43 |
| Hannibal Square | 402 1BD | 1BR,1BA | $2.70 |
| Vida at Health Village | S1 | Studio ,1BA | $2.59 |
Quick Rent Budget Calculator
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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 $1,567 at Maitland City Centre.
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 $2,473.
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.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
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.