Cheap Apartments for Rent in the Downtown Winter Park Neighborhood of Winter Park, FL from $798 (8 Rentals)

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

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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 $1,475. Elon Winter Park has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,612. Here are the most affordable Downtown Winter Park apartments for rent in Orlando, FL:

Apartment ListingModel NameBed/BathPriced From
Hannibal Square430 W. New England Ave./1st Fl2BR,1BA$1,475
Elon Winter ParkThe Tony1BR,1BA$1,612
Park East - Park Knowles Apartments2 Bedroom, 1 Bathroom2BR,1BA$1,750

Best Value Apartments for Rent in Downtown Winter Park, FL

As of August 21, 2026 the best value apartment in the Downtown Winter Park area is the $2.64 price per square foot B3 Model at Bainbridge Winter Park in the in the Courtland Street neighborhood starting from $3,074. The second greatest value Downtown Winter Park apartment is the 2 Bedroom, 1 Bathroom Model at Park East - Park Knowles Apartments starting at $1,750 with a $1.59 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 ListingModel NameBed/BathPrice Per Sq.Ft.
Bainbridge Winter ParkB32BR,2BA$2.64
Park East - Park Knowles Apartments2 Bedroom, 1 Bathroom2BR,1BA$1.59
Paseo at Winter Park VillageRejuvenecer2BR,2BA$2.72
Juno Winter ParkVest1BR,1BA$3.29
Hannibal Square433 W. New England Ave./ Front/3rd Fl/ FrontStudio ,1BA$3.74

Frequently Asked Questions about Cheap Downtown Winter Park Apartments

What is a cheap apartment in Downtown Winter Park?

A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Downtown Winter Park is under $3,057.

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

The cheapest apartment in Downtown Winter Park is Hannibal Square which is listed at $1,700, while the average apartment in Downtown Winter Park costs $2,170.

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 2 regular apartments in Downtown Winter Park that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

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.

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