Cheap Homes for Rent in Winter Park, FL from $900 (61 Rentals)

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property at 312 Orange St

312 Orange St

MaitlandFL32751

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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Orlando's Best Affordable Neighborhoods

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property at 1695 Lee Rd

1695 Lee Rd

Winter ParkFL32789
property at 7340 Swallow Run

7340 Swallow Run

Winter ParkFL32792
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Winter Park, FL Local Guide

Cheapest Neighborhoods for Apartments in Winter Park, FL

Pricing Updated: 04/30/2025

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$2,111$820155

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
Spring Tree VillageStudioStudio,1BA$1,149
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1,194
Central Place At Winter ParkA11BR,1BA$1,195
Signal PointePoint Isabel 1BR,1BA$1,205
Advenir at MagnoliaSR - Lily RStudio,1BA$1,205

Best Value Apartments for Rent in Winter Park, FL

As of April 30, 2025 the best value apartment in the Winter Park area is the $1.27 price per square foot Three Bedroom Model at Lake Weston Point Apartments in the in the Courtland Street neighborhood starting from $1,529. The second greatest value Winter Park apartment is the Pelican Model at Cranes Landing Apartments starting at $1,970 with a $1.64 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.
Lake Weston Point ApartmentsThree Bedroom3BR,2BA$1.27
Cranes Landing ApartmentsPelican3BR,2BA$1.64
Azalea GardensFloorplan 22BR,2BA$1.46
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.37
Alvista Winter ParkDESTINY RENOVATED2BR,2BA$1.48
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
The Avenues of Baldwin ParkFern1BR,1.5BA$1.65
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1.63

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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 303 Apartments for Rent in Winter Park, FL with pricing that ranges from $820 to $9,543. There are also 209 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $950 to $10,500.

What is the current price range for Rental Homes in Winter Park?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winter Park ranges from $950 to $10,500 with an average monthly rent of $3,459.

How much are larger Three and Four Bedroom Rentals in Winter Park?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winter Park range from $1,146 to $9,543, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,300 to $5,800. Four Bedroom Single-Family rentals are also available starting from $2,000 and Four Bedroom Apartments start at $2,355.

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.

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

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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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.