Cheap Apartments for Rent in the Winter Park Neighborhood of Orlando, FL from $400 (51 Rentals)

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

property at 5517 Decatur St

5517 Decatur St

OrlandoFL32807

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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On Baldwin Pond
2 Bedroom Apartments

On Baldwin Pond

829 Lowell BlvdOrlando, FL 32803
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1219 Oregon St
Studio Apartments

1219 Oregon St

1219 Oregon StOrlando, FL 32803
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Bellancia
1 to 3 Bedroom Apartments

Bellancia

7325 Goldenpointe BlvdOrlando, FL 32807
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The Juliette
1 Bedroom Apartments

The Juliette

1225 Moselle AveOrlando, FL 32807

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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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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Winter Park - One of the Best Affordable Neighborhoods in Orlando

Named as one of the Best Affordable Areas to rent in Orlando by our , Local Expert Darla F. See how it ranks!

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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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Goldenrod Pointe
1 to 4 Bedroom Apartments

Goldenrod Pointe

5560 Solidago DrWinter 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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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

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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Showing Results 1-50, Page 1 of 2

Winter Park, Orlando, FL Local Guide

Cheapest Available Winter Park Apartments for Rent

 

The cheapest available apartment rental in the Winter Park area of Orlando, FL is a 1 Bed unit found at Central Place At Winter Park priced from $1,100. District On Baldwin Park has the second lowest priced unit, which is a Studio apartment currently listed from $1,110. Here are the most affordable Winter Park apartments for rent in Orlando, FL:

Apartment ListingModel NameBed/BathPriced From
Central Place At Winter ParkA11BR,1BA$1,100
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Hillcrest Hampton HouseStudioStudio,1BA$1,125
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1,217
Sovereignty at Winter Park ApartmentsA21BR,1BA$1,258
Winter Park WoodsA2-1 Bedroom, 1 Bathroom1BR,1BA$1,265
Shoreview at Baldwin Park1x1A1BR,1BA$1,270
Affinity at Winter Park ApartmentsB12BR,1BA$1,291
Oak Reserve at Winter ParkThe Charleston1BR,1BA$1,300
Venue At Winter ParkSable1BR,1BA$1,308

Best Value Apartments for Rent in Winter Park, FL

As of May 14, 2025 the best value apartment in the Winter Park area is the $1.79 price per square foot Central+ Model at Azure Winter Park in the in the University Commerce Center neighborhood starting from $2,499. The second greatest value Winter Park apartment is the Meeting Model at The Avenues of Baldwin Park starting at $1,825 with a $1.60 price per square foot in the Colonial Town 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.
Azure Winter ParkCentral+3BR,2BA$1.79
The Avenues of Baldwin ParkMeeting3BR,2BA$1.60
Affinity at Winter Park ApartmentsB12BR,1BA$1.16
SeabrookPlan B2B2BR,2BA$1.68
Cranes Landing ApartmentsHeron2BR,2BA$1.64
Bellancia1 Bed | 1 Bath1BR,1BA$1.74
ARIUM Winter ParkBishop1BR,1BA$1.75
Winter Park WoodsA2-1 Bedroom, 1 Bathroom1BR,1BA$1.67
Sovereignty at Winter Park ApartmentsA21BR,1BA$1.68
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1.66

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Pet Friendly Lifestyle
Winter Park, Orlando, FL

Ranked #35

Among neighborhoods in Orlando, FL for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Best Local Schools in
Winter Park, Orlando, FL

School data provided by Great Schools

Lifestyle Ratings

ApartmentHomeLiving.com compiles millions of data points to bring you our detailed rental analysis called 'Lifestyle Ratings' - a comparison of neighborhoods, cities and towns, and rental properties across Florida and customized analysis for Orlando, Florida. Our Lifestyle Ratings help you zero-in on the perfect place to call home. This takes in many factors including our Star Ratings to compare for the best proximity to parks and outdoor amenities, luxury amenities, pet-friendly features, places that make kids happy, proximity to transit, in addition to floorplans, availablity, and pricing. Use Lifestyle Search in the site filter options on this page - and find your Perfect place!

Getting Around the Winter Park Neighborhood in Orlando, FL

Walk Score®

75 / 100

Very Walkable

Most errands can be accomplished on foot

Bike Score®

62 / 100

Bikeable

Some bike infrastructure

Transit Score®

26 / 100

Some Transit

A few nearby public transportation options

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 District On Baldwin Park listed at $1,110.

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

The lowest price for a Cheap One Bedroom Winter Park Apartment is $1,100 at Central Place At Winter Park.

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 $1,291 at Affinity at Winter Park 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 Venue At Winter Park and starts from $1,736.

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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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.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.