Cheap Apartments for Rent in Winter Park, FL from $400 (70 Rentals)

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

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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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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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Goldenrod Pointe
1 to 4 Bedroom Apartments

Goldenrod Pointe

5560 Solidago DrWinter Park, FL 32792
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Branchwood Apartments
Studio to 2 Bedroom Apartments

Branchwood Apartments

7785 Branchwood LnWinter 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 to 2 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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Winter Park Oaks
1 to 3 Bedroom Apartments

Winter Park Oaks

325 Balfour DrWinter 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
Showing Results 1-50, Page 1 of 2

Winter Park, FL Local Guide

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Written By:
Staff Writer
Local Guide Expert

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 09/20/2025

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$4,500$99579

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in Winter Park, FL is a 2 Beds unit found at Ekos at Lake Shadow in the Courtland Street neighborhood priced from $560. San Jose Apartments in the Outer East neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $903. Here is today’s list of the most affordable Winter Park apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Ekos at Lake ShadowB1 302BR,2BA$560
San Jose Apartments1x1 8631BR,1BA$903
Sumerset Apartments1 Bed, 1 bath1BR,1BA$974
Advenir at MagnoliaS - LilyStudio,1BA$1,099
Regency Oaks ApartmentsStudioStudio,2BA$1,112
Birchwood LandingBirchwood A1BR,1BA$1,119
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Garden Park Senior LivingDaisy (Two Bedroom w/Den)2BR,2BA$1,129
Winter Park WoodsA1-Studio, 1 BathroomStudio,1BA$1,129
Spring Tree VillageStudioStudio,1BA$1,149

Best Value Apartments for Rent in Winter Park, FL

As of September 20, 2025 the best value apartment in the Winter Park area is the $1.47 price per square foot 941 Robinhood Ct Model at 941 Robinhood Ct, Unit 941 Robinhood in the in the Orienta Gardens neighborhood starting from $1,850. The second greatest value Winter Park apartment is the Floorplan 2 Model at Azalea Gardens starting at $1,800 with a $1.50 price per square foot in the North Orange 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.
941 Robinhood Ct, Unit 941 Robinhood941 Robinhood Ct2BR,2BA$1.47
Azalea GardensFloorplan 22BR,2BA$1.50
The Avenues of Baldwin ParkMeeting3BR,2BA$1.60
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.28
Calibre Bend ApartmentsDunes Downstairs2BR,2BA$1.62
San Jose Apartments2x1 10332BR,1BA$1.05
Ekos at Lake ShadowB1 302BR,2BA$0.57
Lake Weston Point ApartmentsTwo Bedroom2BR,2BA$1.38
La Aloma2X12BR,1BA$1.51
Sovereignty at Winter Park ApartmentsA21BR,1BA$1.59

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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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Winter Park, FL Apartments Map
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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 Advenir at Magnolia listed at $1,099.

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

The lowest price for a Cheap One Bedroom Winter Park Apartment is $903 at San Jose Apartments.

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 $560 at Ekos at Lake Shadow.

What is the most affordable Winter Park Three Bedroom Apartment?

The best deal on a cheap Winter Park Three Bedroom Apartment rental is at San Jose Apartments and starts from $1,261.

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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