Cheap Apartments for Rent in Winter Park, FL from $400 (80 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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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
  • Utilities Included

The Art of the Rental Viewing: What to look for during a property tour

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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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Alvista Winter Park
1 to 2 Bedroom Apartments

Alvista Winter Park

3935 Sutton Place BlvdWinter Park, FL 32792
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Winter Park Oaks
1 to 3 Bedroom Apartments

Winter Park Oaks

325 Balfour DrWinter Park, FL 32792
  • Utilities Included

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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Winter Park, FL Local Guide

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Local Guide Expert

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 08/04/2025

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$3,610$95080

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in Winter Park, FL is a 1 Bed unit found at San Jose Apartments in the Outer East neighborhood priced from $903. Kingswood Apartments in the Courtland Street neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,050. Here is today’s list of the most affordable Winter Park apartments for rent:

Apartment ListingModel NameBed/BathPriced From
San Jose Apartments1x1 8631BR,1BA$903
Kingswood Apartments1/11BR,1BA$1,050
Sumerset Apartments1 Bed, 1 bath1BR,1BA$1,074
Advenir at MagnoliaS - LilyStudio,1BA$1,099
GOLDEN OAKS3 Bedroom 2 Bathroom3BR,2BA$1,099
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Regency Oaks ApartmentsStudioStudio,2BA$1,112
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Spring Tree VillageStudioStudio,1BA$1,149
Liv at Winter Park Apartment HomesA11BR,1BA$1,168

Best Value Apartments for Rent in Winter Park, FL

As of August 04, 2025 the best value apartment in the Winter Park area is the $1.31 price per square foot Four Bedroom Model at Lake Weston Point Apartments in the in the Courtland Street neighborhood starting from $1,697. The second greatest value Winter Park apartment is the Floorplan 2 Model at Azalea Gardens starting at $1,750 with a $1.46 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.
Lake Weston Point ApartmentsFour Bedroom4BR,2BA$1.31
Azalea GardensFloorplan 22BR,2BA$1.46
La Aloma2X22BR,2BA$1.34
GOLDEN OAKS3 Bedroom 2 Bathroom3BR,2BA$1.05
San Jose Apartments2x1 10332BR,1BA$1.05
Garden Park Senior LivingTwo Bedroom Two Bath (b)2BR,2BA$1.29
The Grand Reserve at Maitland ParkThe Grand A (3rd Floor)1BR,1BA$1.61
Sumerset Apartments1 Bed, 1 bath1BR,1BA$1.38
Sovereignty at Winter Park ApartmentsA21BR,1BA$1.59
Venue At Winter ParkSable1BR,1BA$1.48

Quick Rent Budget Calculator

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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 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 $1,089 at San Jose 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 GOLDEN OAKS and starts from $1,099.

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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An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent

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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.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.