2 Bedroom Apartments for Rent in Winter Park, FL (182 Rentals)

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Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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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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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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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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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

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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Winter Park, FL Local Guide

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Written By:
Staff Writer
Local Guide Expert

Winter Park 2 Bedroom Apartment Units with Current Availability by Neighborhood

Availability Confirmed As of: September 20, 2025

There are currently 92 available 2 Bedroom apartment units in Winter Park, FL neighborhoods that range in price from $1,089 to $2,556. Heres is today's list of the top neighborhoods in Winter Park with the most available 2 Bedroom apartments:

NeighborhoodAvailable UnitsMedian PriceMin Price
Lake Howell92$1,785$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 $1,977. 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 $2,599. 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$1,977
Village Park SeniorVirginia (Two Bedroom w/Den)1,662 Sq Ft$2,599
Aurora on the TrailB51,647 Sq Ft$2,597
Perla Gem LakeB51,439 Sq Ft$3,476
The Majestic at Downtown Baldwin ParkBaron1,406 Sq Ft$2,850
Gables Baldwin ParkB121,405 Sq Ft$4,498
Citron at The Packing DistrictB41,359 Sq Ft$2,690
Azul Baldwin ParkB61,331 Sq Ft$2,852
Trelago ApartmentsBergomot1,315 Sq Ft$2,697
NORA Apartments2D1,310 Sq Ft$2,427

Cheapest Available Winter Park 2 Bedroom Apartments

As of September 20, 2025 the lowest priced 2 Bedroom apartment unit in Winter Park, FL is the B1 30 Model starting from $560 at Ekos at Lake Shadow in the Courtland Street neighborhood. The second most affordable Winter Park 2 Bedroom is the 2x2 1083 Model at San Jose Apartments starting at $1,089 in the Outer East neighborhood. The average price for all 2 Bedroom apartments in Winter Park is currently $2,166. Here is today’s list of the cheapest available 2 Bedroom options in Winter Park:

Apartment ListingModel NamePriced From
Ekos at Lake ShadowB1 30$560
San Jose Apartments2x2 1083$1,089
Garden Park Senior LivingDaisy (Two Bedroom w/Den)$1,129
Sumerset Apartments2 Beds, 2 baths$1,174
Lake Weston Point ApartmentsTwo Bedroom$1,329
Regency Oaks ApartmentsB2$1,332
Sovereignty at Winter Park ApartmentsB1$1,350
Birchwood LandingBirchwood B$1,395
Winter Park WoodsB1-2 Bedrooms, 1.5 Bathrooms$1,399
The Park at RialtoB3$1,399

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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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Winter Park, FL Apartments Map
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Winter Park, FL Rental Homes Map

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 Ekos at Lake Shadow listed at $560.

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 $2,166.

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 $1,977 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 1,091 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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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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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.