Cheap Apartments for Rent in the Downtown Winter Park Neighborhood of Winter Park, FL from $700 (8 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

Search the lowest-cost Apartments available for rent right now in the Downtown Winter Park area of Winter Park.

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.

Read Article

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.

Read Article
Showing Results 1-8, Page 1 of 1

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 Village Park Senior priced from $1,344. Hannibal Square has the second lowest priced unit, which is a Studio apartment currently listed from $1,600. Here are the most affordable Downtown Winter Park apartments for rent in Orlando, FL:

Apartment ListingModel NameBed/BathPriced From
Village Park SeniorOne Bedroom One Bath1BR,1BA$1,344
Hannibal Square433 W. New England Ave./ Front/3rd Fl/ FrontStudio,1BA$1,600
Elon Winter ParkThe Tony1BR,1BA$1,622

Best Value Apartments for Rent in Downtown Winter Park, FL

As of May 23, 2026 the best value apartment in the Downtown Winter Park area is the $2.68 price per square foot Viaje Model at Paseo at Winter Park Village in the in the North Orange neighborhood starting from $3,539. The second greatest value Downtown Winter Park apartment is the B3 Model at Bainbridge Winter Park starting at $2,892 with a $2.49 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 ListingModel NameBed/BathPrice Per Sq.Ft.
Paseo at Winter Park VillageViaje3BR,2BA$2.68
Bainbridge Winter ParkB32BR,2BA$2.49
The Lofts of Winter Park VillageELBB1BR,1BA$2.21
Elon Winter ParkThe Tony1BR,1BA$2.19
Village Park SeniorOsceola1BR,1BA$2.56
Juno Winter ParkLunaStudio ,1BA$3.24
Hannibal Square433 W. New England Ave./ Front/3rd Fl/ FrontStudio ,1BA$3.74

Frequently Asked Questions about Cheap Downtown Winter Park Apartments

What is the price of a cheap apartment in Downtown Winter Park?

The cheapest apartment in Downtown Winter Park is Village Park Senior which is listed at $1,344, while the average apartment in Downtown Winter Park costs $3,227.

What types of apartments are the cheapest in Downtown Winter Park?

Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 9 regular apartments in Downtown Winter Park that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

How do the prices of cheap apartments compare to the average apartment in Downtown Winter Park?

Cheap apartments in Downtown Winter Park have an average cost of $503 which is $2,724 cheaper than the average rent for all rentals in Downtown Winter Park.

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

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

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.

decorative image for Your Guide to the Perfect Orlando Neighborhood for Student Renters article

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.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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.

decorative image for The Soul of the City Beautiful: What Life in Orlando Is Really Like article

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

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

decorative image for Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts article

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.