2 Bedroom Apartments for Rent in Winter Park, FL (172 Rentals)

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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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El Cortez Apartments
2 Bedroom Apartments

El Cortez Apartments

210 E Morse BlvdWinter Park, FL 32789
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Goldenrod Pointe
2 Bedroom Apartments

Goldenrod Pointe

5560 Solidago DrWinter Park, FL 32792
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Tuscany at Aloma
2 Bedroom Apartments

Tuscany at Aloma

6999 Aloma AveWinter Park, FL 32792
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Eastbrook Apartments
2 Bedroom Apartments

Eastbrook Apartments

2610-2617 Eastbrook BlvdWinter Park, FL 32792
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Branchwood Apartments
2 Bedroom Apartments

Branchwood Apartments

7785 Branchwood LnWinter Park, FL 32792
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Winter Park Oaks
2 Bedroom Apartments

Winter Park Oaks

325 Balfour DrWinter Park, FL 32792
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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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Park East Knowles
2 Bedroom Apartments

Park East Knowles

311 N Knowles AveWinter Park, FL 32789
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Showing Results 1-50, Page 1 of 4

Winter Park, FL Local Guide

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Local Guide Expert

Winter Park 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: July 09, 2025

There are currently 76 available 2 Bedroom apartment units in Winter Park, FL neighborhoods that range in price from $1,089 to $3,535. Heres is today's list of the top neighborhoods in Winter Park with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Lake Howell76$1,844$1,089

Largest Available Winter Park 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winter Park, FL is found at Regency Oaks Apartments in the Northeast neighborhood and is 1,800 square feet priced from $1,966. Aurora on the Trail in the Colonial Town Center neighborhood has the second largest 2 Bedroom, which is sized at 1,647 square feet and currently listed start at $2,944. Here is today’s list of the largest available 2 Bedroom units in Winter Park:

Apartment ListingModel NameSquare FootagePriced From
Regency Oaks ApartmentsB5 Townhouse1,800 Sq Ft$1,966
Aurora on the TrailB51,647 Sq Ft$2,944
The Village at Lake LilyB1.21,500 Sq Ft$2,493
Gables Baldwin ParkB121,405 Sq Ft$4,498
Citron at The Packing DistrictB41,359 Sq Ft$2,775
Trelago ApartmentsBergomot1,355 Sq Ft$2,688
The Cannery at The Packing DistrictB21,325 Sq Ft$2,701
NORA Apartments2D1,310 Sq Ft$2,679
Luna at Lake ShadowB41,299 Sq Ft$2,147
Perla Gem LakeB41,295 Sq Ft$2,965

Cheapest Available Winter Park 2 Bedroom Apartments

As of July 09, 2025 the lowest priced 2 Bedroom apartment unit in Winter Park, FL is the 2x2 1083 Model starting from $1,089 at San Jose Apartments in the Outer East neighborhood. The second most affordable Winter Park 2 Bedroom is the Two Bedroom Two Bath (b) Model at Garden Park Senior Living starting at $1,269 in the Orienta Gardens neighborhood. The average price for all 2 Bedroom apartments in Winter Park is currently $2,472. Here is today’s list of the cheapest available 2 Bedroom options in Winter Park:

Apartment ListingModel NamePriced From
San Jose Apartments2x2 1083$1,089
Garden Park Senior LivingTwo Bedroom Two Bath (b)$1,269
Sumerset Apartments2 Beds, 2 baths$1,274
Lake Weston Point ApartmentsTwo Bedroom$1,329
Birchwood LandingBirchwood B$1,355
Sovereignty at Winter Park ApartmentsB1$1,391
Venue At Winter ParkMaple$1,395
The Avenues of Baldwin ParkAnson$1,428
Regency Oaks ApartmentsB2$1,441

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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 2 Bedroom Winter Park Apartments

What is the Cheapest apartment in Winter Park with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winter Park is at San Jose Apartments listed at $1,089.

How much is the average rent for a 2 Bedroom Winter Park Apartment?

The average rent for a 2 Bedroom Apartment in Winter Park is $2,472.

What is the largest available 2 Bedroom Winter Park Apartment for rent?

Today's apartment with the most square footage in Winter Park is a 1,800 square feet unit starting from $1,966 at Regency Oaks Apartments.

What is the average size for Winter Park 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Winter Park is currently 1,104 sq ft.

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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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

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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.