Cheap Apartments for Rent in Winter Park, FL from $400 (84 Rentals)

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

Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

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Tuscany at Aloma
1 to 3 Bedroom Apartments

Tuscany at Aloma

6999 Aloma AveWinter Park, FL 32792
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Winter Park Oaks
1 to 3 Bedroom Apartments

Winter Park Oaks

325 Balfour DrWinter Park, FL 32792
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El Cortez Apartments
1 to 2 Bedroom Apartments

El Cortez Apartments

210 E Morse BlvdWinter Park, FL 32789
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Calvary Tower
1 Bedroom Apartments

Calvary Tower

1099 Clay StWinter Park, FL 32789
Senior Living
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Branchwood Apartments
Studio to 2 Bedroom Apartments

Branchwood Apartments

7785 Branchwood LnWinter Park, FL 32792
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Golden Oaks
2 to 3 Bedroom Apartments

Golden Oaks

7701 Acorn Woods CirWinter Park, FL 32792
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Alvista Winter Park
1 to 2 Bedroom Apartments

Alvista Winter Park

3935 Sutton Place BlvdWinter Park, FL 32792
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Sun Bay Apartments
1 Bedroom Apartments

Sun Bay Apartments

7001 Aloma AveWinter Park, FL 32792
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Eastbrook Apartments
1 to 2 Bedroom Apartments

Eastbrook Apartments

2610-2617 Eastbrook BlvdWinter Park, FL 32792
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Park East Knowles
Studio to 2 Bedroom Apartments

Park East Knowles

311 N Knowles AveWinter Park, FL 32789
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Indigo Winter Park
1 Bedroom Apartments

Indigo Winter Park

220 S Semoran BlvdWinter Park, FL 32792
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Azure Winter Park
Studio to 3 Bedroom Apartments

Azure Winter Park

3650 Summer Wind DrWinter Park, FL 32792
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Serena Winter Park
1 to 2 Bedroom Apartments

Serena Winter Park

2890 Red Lion SqWinter Park, FL 32792
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Winter Park, FL Local Guide

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Staff Writer
Local Guide Expert

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 03/27/2025

Current apartment rentals in the Winter Park, FL area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Winter Park Apartments for rent:

NeighborhoodMedian PriceMin PriceAvailable Units
Lake Howell$2,043$8202101

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in Winter Park, FL is a Studio unit found at Kingswood Apartments in the Courtland Street neighborhood priced from $900. Garden Park Senior Living in the Orienta Gardens neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $986. Here is today’s list of the most affordable Winter Park apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Kingswood ApartmentsStudioStudio,1BA$900
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$986
Hillcrest Hampton HouseStudioStudio,1BA$1,000
Advenir at MagnoliaSR - Lily RStudio,1BA$1,099
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Birchwood LandingBirchwood A1BR,1BA$1,119
Cranes Landing ApartmentsSandpiper1BR,1BA$1,164

Best Value Apartments for Rent in Winter Park, FL

As of March 27, 2025 the best value apartment in the Winter Park area is the $1.42 price per square foot 3601 Lake Sarah Dr Model at 3601 Lake Sarah Dr in the in the North Orange neighborhood starting from $3,600. The second greatest value Winter Park apartment is the 216 Brighton Way Model at 216 Brighton Way starting at $2,369 with a $1.00 price per square foot in the Northeast neighborhood. Here is today’s list of the best values for Winter Park apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
3601 Lake Sarah Dr3601 Lake Sarah Dr4BR,2BA$1.42
216 Brighton Way216 Brighton Way3BR,2BA$1.00
Lake Weston Point ApartmentsFour Bedroom4BR,2BA$1.19
Azalea GardensFloorplan 22BR,2BA$1.46
Sorrento2B 1.5B TOWN2BR,1.5BA$1.42
The Avenues of Baldwin ParkMeeting3BR,2BA$1.61
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.27
The Grand Reserve at Maitland ParkThe Grand A (3rd Floor)1BR,1BA$1.60
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$1.23
2920 E Jefferson St2920 E Jefferson St1BR,1BA$1.57

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Winter Park Overview

Winter Park, Florida offers something for everyone. This suburban city of over 29,000 people provides historical, cultural, and recreational opportunities. Well-known for its museums, art galleries, and parks, the town is home to Rollins College. Outdoor enthusiasts can enjoy water activities at nearby lakes, or explore local hiking and biking trails. With plenty of options for apartments in Winter Park, find a new home here is easy.

Why live in Winter Park, FL?

If you're unsure about relocating to Winter Park apartments, consider all it has to offer. Its convenient location just northeast of Orlando allows you to reap the benefits of living near a sizeable city while enjoying the amenities of a smaller community. Winter Park apartments provide an impressive selection of housing options. This suburban hamlet offers upscale shopping and dining. A local chain of lakes provides ample opportunities for fishing, swimming, and boating. Rollins College and other post-secondary institutions offer educational opportunities in everything from liberal arts to fine arts. Cultural events and a thriving community center bring residents together.

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winter Park, FL Rentals by Map

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See the most popular apartments and homes in Winter Park, FL

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Getting Around Winter Park, FL

Walk Score®

71 / 100

Very Walkable

Most errands can be accomplished on foot

Bike Score®

57 / 100

Bikeable

Some bike infrastructure

Transit Score®

22 / 100

Minimal Transit

It may be possible to get on a bus

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Cheap Winter Park Apartments

What is the Cheapest Studio apartment in Winter Park?

Currently the most affordable Cheap Studio Apartment in Winter Park is at Kingswood Apartments listed at $900.

How much is rent for a Cheap One Bedroom Winter Park Apartment?

The lowest price for a Cheap One Bedroom Winter Park Apartment is $986 at Garden Park Senior Living.

What is the lowest price for a Cheap Two Bedroom Winter Park Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Winter Park is starting from $1,181 at Sumerset Apartments.

What is the most affordable Winter Park Three Bedroom Apartment?

The best deal on a cheap Winter Park Three Bedroom Apartment rental is at Sumerset Apartments and starts from $1,384.

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.

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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

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While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.