Cheap Homes for Rent in Winter Park, FL from $800 (50 Rentals)

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property at 312 Orange St

312 Orange St

MaitlandFL32751

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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property at 1695 Lee Rd

1695 Lee Rd

Winter ParkFL32789
property at 2500 Lee Rd

2500 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: 03/25/2025

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$2,046$8202218

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 $986. 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$986
Hillcrest Hampton HouseStudioStudio,1BA$1,000
Advenir at MagnoliaS - LilyStudio,1BA$1,099
District On Baldwin ParkE235xecutive StudioStudio,1BA$1,110
Birchwood LandingBirchwood A1BR,1BA$1,119
Solis at Winter ParkA11BR,1BA$1,160

Best Value Apartments for Rent in Winter Park, FL

As of March 25, 2025 the best value apartment in the Winter Park area is the $1.42 price per square foot 3601 Lake Sarah Dr Model at 3601 Lake Sarah Dr in the in the North Orange neighborhood starting from $3,600. The second greatest value Winter Park apartment is the Four Bedroom Model at Lake Weston Point Apartments starting at $1,543 with a $1.19 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.
3601 Lake Sarah Dr3601 Lake Sarah Dr4BR,2BA$1.42
Lake Weston Point ApartmentsFour Bedroom4BR,2BA$1.19
Azalea GardensFloorplan 22BR,2BA$1.46
Sorrento2B 1.5B TOWN2BR,1.5BA$1.42
The Avenues of Baldwin ParkMeeting3BR,2BA$1.61
Sumerset Apartments3 Beds, 2 baths3BR,2BA$1.27
The Grand Reserve at Maitland ParkThe Grand A (3rd Floor)1BR,1BA$1.60
Garden Park Senior LivingOne Bedroom One Bath (b)1BR,1BA$1.23
Summerlin at Winter Park ApartmentsAqua1BR,1BA$1.66
2920 E Jefferson St2920 E Jefferson St1BR,1BA$1.57

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Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 304 Apartments for Rent in Winter Park, FL with pricing that ranges from $820 to $9,609. There are also 197 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $850 to $45,000.

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 $850 to $45,000 with an average monthly rent of $5,677.

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 $9,609, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,750 to $6,000. Four Bedroom Single-Family rentals are also available starting from $2,175 and Four Bedroom Apartments start at $2,414.

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 F

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.

decorative image for Understanding Amenity Fees: Know Where You Might Be Able to Save Money article

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.

decorative image for Renting Smart: Lease Basics Every Renter Needs article

Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

decorative image for Battling the Butts: Your Guide to the Reality of Smoke-Free Renting article

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.