Cheap Apartments for Rent in Winter Park, FL from $400 (90 Rentals)

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Cheap Apartments 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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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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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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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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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 Oaks
1 to 3 Bedroom Apartments

Winter Park Oaks

325 Balfour DrWinter Park, FL 32792
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Showing Results 1-50, Page 1 of 2

Winter Park, FL Local Guide

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Local Guide Expert

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 05/02/2025

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$2,329$820159

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 $1,086. 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$1,086
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Birchwood LandingBirchwood A1BR,1BA$1,119
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Advenir at MagnoliaS - LilyStudio,1BA$1,130
Spring Tree VillageStudioStudio,1BA$1,149
Central Place At Winter ParkA11BR,1BA$1,195
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1,195
Regency Oaks ApartmentsA11BR,1BA$1,237

Best Value Apartments for Rent in Winter Park, FL

As of May 03, 2025 the best value apartment in the Winter Park area is the $1.63 price per square foot 4177 N Orange Blossom Trail Model at 4177 N Orange Blossom Trail, Unit 304 in the in the Downtown Orlando neighborhood starting from $2,695. The second greatest value Winter Park apartment is the Four Bedroom Model at Lake Weston Point Apartments starting at $1,697 with a $1.31 price per square foot in the Courtland Street 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.
4177 N Orange Blossom Trail, Unit 3044177 N Orange Blossom Trail3BR,2BA$1.63
Lake Weston Point ApartmentsFour Bedroom4BR,2BA$1.31
Azalea GardensFloorplan 22BR,2BA$1.46
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.37
Cranes Landing ApartmentsHeron2BR,2BA$1.64
Oasis ClubThe Tide2BR,2BA$1.34
Sorrento2B 1B2BR,1BA$1.63
The Grand Reserve at Maitland ParkThe Grand A (3rd Floor)1BR,1BA$1.65
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$1.35
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1.63

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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 $1,050 at Kingswood 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 $1,200 at Kingswood 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 $1,495.

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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Written by: Christine Leonard, Esq.

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