151 N Orlando Ave
Winter ParkFL32789
Cheap Homes for Rent in Downtown Winter Park Neighborhood of Winter Park, FL from $1,400 (4 Rentals)
Search the lowest-cost Homes available for rent right now in the Downtown Winter Park area of Winter Park.
731 W Comstock Ave
Winter ParkFL32789
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
830 Carver St
Winter ParkFL32789
503 Kilshore Ln
Winter ParkFL32789
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.
Showing Results 1-4, Page 1 of 1
Downtown Winter Park, Winter Park, FL Local Guide
How much does it cost to rent a home in Downtown Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Downtown Winter Park 2 Bedroom Homes for Rent | $2,525 | $2,050 | $3,200 |
| Downtown Winter Park 3 Bedroom Homes for Rent | $3,129 | $1,950 | $5,500 |
Browse Homes for Rent in this Neighborhood
There are currently 4 rentals with your search options within a 1 mile radius of the Downtown Winter Park Neighborhood of Winter Park, FL.
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Best Value Apartments for Rent in Downtown Winter Park, FL
As of July 05, 2026 the best value apartment in the Downtown Winter Park area is the $2.55 price per square foot B1 Model at Bainbridge Winter Park in the in the Courtland Street neighborhood starting from $2,764. The second greatest value Downtown Winter Park apartment is the EWBB Model at The Lofts of Winter Park Village starting at $1,875 with a $1.98 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 | B1 | 2BR,2BA | $2.55 |
| The Lofts of Winter Park Village | EWBB | 1BR,1BA | $1.98 |
| Paseo at Winter Park Village | Andar | 1BR,1BA | $2.64 |
| Juno Winter Park | Vest | 1BR,1BA | $3.44 |
| Hannibal Square | 433 W. New England Ave./ Front/3rd Fl/ Front | Studio ,1BA | $3.74 |
Frequently Asked Questions about Downtown Winter Park
What type of rentals are currently available in Downtown Winter Park?
There are currently 56 Apartments for Rent in Downtown Winter Park, FL with pricing that ranges from $1,330 to $3,630. There are also 18 Single Family Homes for rent, Condos, and Townhome rentals currently available in Downtown Winter Park ranging from $1,450 to $5,500.
What is the current price range for Rental Homes in Downtown Winter Park?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Downtown Winter Park ranges from $1,450 to $5,500 with an average monthly rent of $2,659.
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.
Your Guide to the Perfect Orlando Neighborhood for Student Renters
Written by: Darla Ferrara
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.
Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers
Written by: Darla Ferrara
When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.
The Soul of the City Beautiful: What Life in Orlando Is Really Like
Written by: Darla Ferrara
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
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.