2 Bedroom Apartments for Rent in Winter Park, FL (161 Rentals)

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Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

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El Cortez Apartments
2 Bedroom Apartments

El Cortez Apartments

210 E Morse BlvdWinter Park, FL 32789
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Golden Oaks
2 Bedroom Apartments

Golden Oaks

7701 Acorn Woods CirWinter 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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The Fisher
2 Bedroom Apartments

The Fisher

2001 Glenridge WayWinter Park, FL 32792
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Park East Knowles
2 Bedroom Apartments

Park East Knowles

311 N Knowles AveWinter Park, FL 32789
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Azure Winter Park
2 Bedroom Apartments

Azure Winter Park

3650 Summer Wind DrWinter Park, FL 32792
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Alvista Winter Park
2 Bedroom Apartments

Alvista Winter Park

3935 Sutton Place BlvdWinter Park, FL 32792
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La Aloma Apartments
2 Bedroom Apartments

La Aloma Apartments

3040 Aloma AveWinter Park, FL 32792
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The Oaks
2 Bedroom Apartments

The Oaks

700 N Denning DrWinter Park, FL 32789
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1250 S Denning Dr
2 Bedroom Apartments

1250 S Denning Dr

1250 S Denning DrWinter Park, FL 32789
Showing Results 1-50, Page 1 of 4

Winter Park, FL Local Guide

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Winter Park 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: February 27, 2025

There are currently 593 available 2 Bedroom apartment units in Winter Park, FL neighborhoods that range in price from $989 to $3,972. Heres is today's list of the top neighborhoods in Winter Park with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Lake Howell593$1,726$989

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 1,592 square feet and currently listed start at $2,759. 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 TrailB41,592 Sq Ft$2,759
The Village at Lake LilyB1.21,500 Sq Ft$2,626
The Cannery at The Packing DistrictB21,325 Sq Ft$2,597
Audubon ParkBurroughs1,324 Sq Ft$2,183
Maitland City CentreB61,310 Sq Ft$2,501
Enders Place at Baldwin ParkAzalea1,287 Sq Ft$2,440
The Majestic at Downtown Baldwin ParkShaldon1,280 Sq Ft$2,820
The AdelineB3A1,263 Sq Ft$2,353
MAA Baldwin ParkDual Level 2x2.5 1214-1248 SF1,248 Sq Ft$2,290

Cheapest Available Winter Park 2 Bedroom Apartments

As of February 27, 2025 the lowest priced 2 Bedroom apartment unit in Winter Park, FL is the 2/1 Model starting from $1,300 at Kingswood Apartments in the Courtland Street neighborhood. The second most affordable Winter Park 2 Bedroom is the Gardenia Model at Summerlin at Winter Park Apartments starting at $1,333 in the University Commerce Center neighborhood. The average price for all 2 Bedroom apartments in Winter Park is currently $2,401. Here is today’s list of the cheapest available 2 Bedroom options in Winter Park:

Apartment ListingModel NamePriced From
Kingswood Apartments2/1$1,300
Summerlin at Winter Park ApartmentsGardenia$1,333
Venue At Winter ParkMaple$1,366
Sovereignty at Winter Park ApartmentsB1$1,391
Solis at Winter ParkB2$1,432
Regency Oaks ApartmentsB2$1,441
Signal PointePonce Inlet$1,475
Sorrento2B 1B$1,490
The Grand Reserve at Maitland ParkThe Grand C$1,491
Alvista Winter ParkCAMELIA RENOVATED$1,504

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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 Kingswood Apartments listed at $1,300.

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 $2,401.

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 1,110 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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