Cheap Apartments for Rent in Winter Park, FL from $400 (89 Rentals)

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

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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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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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
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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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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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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
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Alvista Winter Park
1 to 2 Bedroom Apartments

Alvista Winter Park

3935 Sutton Place BlvdWinter Park, FL 32792

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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Winter Park, FL Local Guide

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Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 07/07/2025

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$2,106$903168

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. GOLDEN OAKS in the The Enclave at Lake Jean neighborhood has the second lowest priced unit, which is a 3 Beds apartment currently listed from $984. 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
GOLDEN OAKS3 Bedroom 2 Bathroom3BR,2BA$984
Kingswood Apartments1/11BR,1BA$1,050
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Birchwood LandingBirchwood A1BR,1BA$1,119
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Advenir at MagnoliaSR - Lily RStudio,1BA$1,149
Spring Tree VillageStudioStudio,1BA$1,149
SorrentoLarge EfficiencyStudio,1BA$1,170
Winter Park WoodsA1-Studio, 1 BathroomStudio,1BA$1,200

Best Value Apartments for Rent in Winter Park, FL

As of July 07, 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 Pelican Model at Cranes Landing Apartments starting at $1,832 with a $1.53 price per square foot in the University Commerce Center 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
Cranes Landing ApartmentsPelican3BR,2BA$1.53
Azalea GardensFloorplan 22BR,2BA$1.46
La Aloma2X22BR,2BA$1.34
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.37
Calibre Bend ApartmentsDunes Downstairs2BR,2BA$1.60
GOLDEN OAKS3 Bedroom 2 Bathroom3BR,2BA$0.94
San Jose Apartments2x1 10332BR,1BA$1.05
Lake Weston Point ApartmentsTwo Bedroom2BR,2BA$1.38
Garden Park Senior LivingTwo Bedroom Two Bath (b)2BR,2BA$1.33

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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 a cheap apartment in Winter Park?

A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Winter Park is under $1,200.

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

The cheapest apartment in Winter Park is San Jose Apartments which is listed at $903, while the average apartment in Winter Park costs $2,106.

What types of apartments are the cheapest in 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 5 regular apartments in Winter Park that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

How do the prices of cheap apartments compare to the average apartment in Winter Park?

Cheap apartments in Winter Park have an average cost of $831 which is $1,275 cheaper than the average rent for all rentals in Winter Park.

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

Written by: Darla Ferrara

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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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.

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

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.