Apartments for Rent in the Downtown Winter Park Neighborhood of Winter Park, FL (76 Rentals)

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property at 779 West Lyman Avenue

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950
Total Monthly Price
$2,950

3 Bedroom, 2 Bath Home for Rent

Available Now

779 West Lyman Avenue

Winter ParkFL32789

Orlando's Best Affordable Neighborhoods

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

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property at 662 Callahan St

$2,408

Total Monthly Price

Total Monthly Price

Base Rent
$2,408
Total Monthly Price
$2,408

2 Bedroom, 1 Bath Home for Rent

Available Nov 25

662 Callahan St

Winter ParkFL32789

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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property at 151 N Orlando Ave

$1,450 - $2,750

1 To 2 Bedroom Rentals

Available Now

151 N Orlando Ave

Winter ParkFL32789
property at 1440 Michigan Ave

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400
Total Monthly Price
$2,400

2 Bedroom, 2 Bath Home for Rent

Available Now

1440 Michigan Ave

Winter ParkFL32789
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Park West Condominiums
Studio Apartments

Park West Condominiums

200-300 Carolina AveWinter Park, FL 32789
  • Utilities Included
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400 W Swoope Ave
2 Bedroom Apartments

400 W Swoope Ave

400 W Swoope AveWinter Park, FL 32789

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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600 N Park Ave
1 Bedroom Apartments

600 N Park Ave

600 N Park AveWinter Park, FL 32789
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The Landmark
Studio Apartments

The Landmark

140 E Morse BlvdWinter Park, FL 32789
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141 E Swoope Ave
Studio Apartments

141 E Swoope Ave

141 E Swoope AveWinter Park, FL 32789

Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

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THE CLOISTERS
Studio Apartments

THE CLOISTERS

200 S Interlachen AveWinter Park, FL 32789
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THE CLOISTERS
Studio Apartments

THE CLOISTERS

100 S Interlachen AveWinter Park, FL 32789
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Villa Siena
Studio Apartments

Villa Siena

315 E New England AveWinter Park, FL 32789
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THE CLOISTERS
Studio Apartments

THE CLOISTERS

106 S Interlachen AveWinter Park, FL 32789

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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Showing Results 1-50, Page 1 of 2

Frequently Asked Questions about Downtown Winter Park

How much are Studio apartments in Downtown Winter Park?

There are currently 17 Studio Apartments in Downtown Winter Park with rent ranges from $1,330 to $1,950 with an average price of $1,699.

What is the current price range for One Bedroom Downtown Winter Park Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Downtown Winter Park ranges from $1,400 to $2,339 with an average monthly rent of $1,924.

What does renting a Two Bedroom Apartment in Downtown Winter Park cost?

The monthly rent prices of Two Bedroom Apartments currently available in Downtown Winter Park range from $1,750 to $3,168. Today's average rental price for Two Bedrooms here is $2,442.

How expensive are Downtown Winter Park Three Bedroom Apartments?

There are currently 12 Three Bedroom Apartments listings available in Downtown Winter Park on ApartmentHomeLiving.com. The pricing ranges from $1,900 to $3,608 - averaging $3,221 for the location.

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.

Helpful Local Expert Guides

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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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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Written by: Darla Ferrara

There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers

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When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

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The Soul of the City Beautiful: What Life in Orlando Is Really Like

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When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.