
2 Bedroom Apartments for Rent in Winter Park, FL (254 Rentals)


Bainbridge Winter Park

Juno Winter Park

Cranes Landing Apartments

Oak Reserve at Winter Park

Seabrook

Seven41 Winter Park

Berkshire Winter Park

Paseo at Winter Park Village

Central Place At Winter Park
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

Calibre Bend Apartments

The Taylor at Winter Park

Liv at Winter Park Apartment Homes

Summerlin at Winter Park Apartments

Winter Park Woods Apartments

San Jose Apartments

Eastbrook Apartments

Park East - Park Knowles Apartments

Total Monthly Price
Rosalia Winter Park 55+ Active Adult Community

Carlton Arms of Winter Park
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.

La Aloma

Westmount at Winter Park

POSTE Winter Park

Total Monthly Price
Atlas at Winter Park

Signal Pointe

Total Monthly Price
Solis at Winter Park

The Vista at Winter Park

Total Monthly Price
Stonecastle Apartment Homes

Alvista Winter Park

Hannibal Square
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.

Village Park Senior

Golden Oaks

Waterbridge Subdivision

ARIUM Winter Park

Total Monthly Price
1360 Formosa Ave, Unit 1360 Formosa, Unit 1360 Formosa

1500 Gay Rd, Unit 9D, Unit 9D

Total Monthly Price
662 Callahan St, Unit SI ID1308311P

7290 Daniel Webster Dr

3254 Howell Branch Rd

3651 Goldenrod Rd
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2500 Lee Rd

1000 S Semoran Blvd

7340 Swallow Run

7328 Swallow Run

3651 N Goldenrod Rd

2911 Antique Oaks Cir

7004 Mills Rd

3011 George Mason Ave

3012 Patel Dr

2523 Alexa Ct
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Winter Park, FL Local Guide

How much does it cost to rent an apartment in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park Studio Apartments | $1,654 | $900 | $3,588 |
| Winter Park 1 Bedroom Apartments | $1,790 | $250 | $3,522 |
Winter Park 2 Bedroom Apartments | $2,215 | $956 | $5,209 |
| Winter Park 3 Bedroom Apartments | $2,785 | $1,082 | $6,500 |
| Winter Park 4 Bedroom Apartments | $2,253 | $1,844 | $3,945 |
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Winter Park, FL Local Guide

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Winter Park 2 Bedroom Apartment Units with Current Availability by Neighborhood
Availability Confirmed As of: May 21, 2026There are currently 55 available 2 Bedroom apartment units in Winter Park, FL neighborhoods that range in price from $1,097 to $2,735. Heres is today's list of the top neighborhoods in Winter Park with the most available 2 Bedroom apartments:
| Neighborhood | Available Units | Median Price | Min Price |
|---|---|---|---|
| Lake Howell | 55 | $1,795 | $1,097 |
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 $1,877. Village Park Senior in the North Orange neighborhood has the second largest 2 Bedroom, which is sized at 1,662 square feet and currently listed start at $2,425. Here is today’s list of the largest available 2 Bedroom units in Winter Park:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Regency Oaks Apartments | B5 Townhouse | 1,800 Sq Ft | $1,877 |
| Village Park Senior | Virginia (Two Bedroom w/Den) | 1,662 Sq Ft | $2,425 |
| Aurora on the Trail | B5 | 1,647 Sq Ft | $2,785 |
| The Village at Lake Lily | B1.2 | 1,500 Sq Ft | $2,738 |
| NORA Apartments | 2E | 1,444 Sq Ft | $2,800 |
| Gables Baldwin Park | B12 | 1,405 Sq Ft | $3,938 |
| Audubon Park | Burroughs | 1,324 Sq Ft | $2,485 |
| MAA Baldwin Park | Traditional 2x2 1141-1291 SF | 1,291 Sq Ft | $2,515 |
| Maitland City Centre | B5 | 1,261 Sq Ft | $2,495 |
| The Parker at Maitland Station Apartments | B5 | 1,256 Sq Ft | $2,585 |
Cheapest Available Winter Park 2 Bedroom Apartments
As of May 21, 2026 the lowest priced 2 Bedroom apartment unit in Winter Park, FL is the 2 Beds, 2 baths Model starting from $1,200 at Sumerset Apartments in the Courtland Street neighborhood. The second most affordable Winter Park 2 Bedroom is the 2/1 Model at Kingswood Apartments starting at $1,200 . The average price for all 2 Bedroom apartments in Winter Park is currently $2,215. Here is today’s list of the cheapest available 2 Bedroom options in Winter Park:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Sumerset Apartments | 2 Beds, 2 baths | $1,200 |
| Kingswood Apartments | 2/1 | $1,200 |
| Regency Oaks Apartments | B2 | $1,332 |
| Eastbrook Apartments | Two Bed One Bath | $1,350 |
| Garden Park Senior Living | Two Bedroom Two Bath (b) | $1,369 |
| Birchwood Landing | Birchwood B | $1,375 |
| Shoreview at Baldwin Park | 2x1 | $1,375 |
| Carlton Arms of Winter Park | C2 Upstairs | $1,376 |
| The Park at Rialto | B2 | $1,379 |
| Avenues of Baldwin Park | Anson (Standard) B1wm | $1,395 |
Your Guide to the Perfect Orlando Neighborhood for Student Renters
Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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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.
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
See the most popular apartments and homes in Winter Park, FL
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 Sumerset Apartments listed at $1,200.
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 $2,215.
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 $1,877 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 1,096 sq ft.
Expert Rental Resources
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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