Winter Park Florida Homes for Rent

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79 total properties
Did you mean the neighborhood Winter Park?
View 7338 SWALLOW RUN 7338 Winter Park, FL MLS# TB8543318
  • Recently Listed
1 of 11
$1,600
2

Beds

2.0

Baths

774

Sq.Ft.

7338 SWALLOW RUN 7338

Winter Park, FL

View 937 ARAGON AVE Winter Park, FL MLS# O6436654
  • Recently Listed with Virtual Tour
1 of 23
$1,995
2

Beds

1.1

Baths

988

Sq.Ft.

937 ARAGON AVE

Winter Park, FL

View 450 W CANTON AVENUE Winter Park, FL MLS# O6434931
  • Recently Listed with Virtual Tour
1 of 38
$3,200
3

Beds

2.0

Baths

1,782

Sq.Ft.

450 W CANTON AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 7033 EASTER STREET Winter Park, FL MLS# O6428828
  • Recently Listed with Virtual Tour
1 of 42
$3,100
4

Beds

3.0

Baths

2,151

Sq.Ft.

7033 EASTER STREET

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1000 S SEMORAN BOULEVARD 305 Winter Park, FL MLS# O6435992
  • Recently Listed with Virtual Tour
1 of 19
$1,195
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 305

Winter Park, FL

View 1741 MIZELL AVENUE Winter Park, FL MLS# O6435821
  • Recently Listed
1 of 37
$4,200
3

Beds

2.0

Baths

2,015

Sq.Ft.

1741 MIZELL AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3391 CEDAR SPRINGS PLACE 168 Winter Park, FL MLS# O6427919
  • Recently Listed with Virtual Tour
1 of 16
$1,549
2

Beds

2.1

Baths

1,031

Sq.Ft.

3391 CEDAR SPRINGS PLACE 168

Winter Park, FL

View 436 W SWOOPE AVENUE Winter Park, FL MLS# O6435450
  • Recently Listed with Virtual Tour
1 of 60
$4,300
4

Beds

3.1

Baths

2,602

Sq.Ft.

436 W SWOOPE AVENUE

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6435262
  • Recently Listed
1 of 2
$2,500
Studio

Beds

0.0

Baths

Address not provided

Winter Park, FL

View 1720 MILLER AVENUE Winter Park, FL MLS# O6435312
  • Recently Listed with Virtual Tour
1 of 20
$1,775
2

Beds

1.0

Baths

800

Sq.Ft.

1720 MILLER AVENUE

Winter Park, FL

View 1500 GAY ROAD 25B Winter Park, FL MLS# O6434320
  • Recently Listed with Virtual Tour
1 of 19
$1,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 25B

Winter Park, FL

View 1420 MAGNOLIA AVENUE Winter Park, FL MLS# O6433762
  • Recently Listed with Virtual Tour
1 of 67
$8,900
4

Beds

3.1

Baths

3,174

Sq.Ft.

1420 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1695 LEE ROAD E215 Winter Park, FL MLS# O6434749
  • Recently Listed with Virtual Tour
1 of 82
$1,750
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E215

Winter Park, FL

View 1695 LEE ROAD E115 Winter Park, FL MLS# O6434751
  • Recently Listed with Virtual Tour
1 of 45
$1,750
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E115

Winter Park, FL

View 524 N LAKEMONT AVENUE Winter Park, FL MLS# O6434416
  • Recently Listed with Virtual Tour
1 of 20
$2,300
3

Beds

2.0

Baths

1,432

Sq.Ft.

524 N LAKEMONT AVENUE

Winter Park, FL

View 1618 INDIANA AVENUE Winter Park, FL MLS# O6434146
  • Recently Listed with Virtual Tour
1 of 14
$1,995
2

Beds

1.0

Baths

1,604

Sq.Ft.

1618 INDIANA AVENUE

Winter Park, FL

View 1618 INDIANA AVENUE 1616 Winter Park, FL MLS# O6434163
  • Recently Listed with Virtual Tour
1 of 14
$1,995
2

Beds

1.0

Baths

802

Sq.Ft.

1618 INDIANA AVENUE 1616

Winter Park, FL

View 3370 CEDAR SPRINGS PLACE 156 Winter Park, FL MLS# O6434022
  • Recently Listed with Virtual Tour
1 of 13
$1,625
2

Beds

2.1

Baths

1,031

Sq.Ft.

3370 CEDAR SPRINGS PLACE 156

Winter Park, FL

View 1812 KILLARNEY DRIVE Winter Park, FL MLS# O6433858
  • Virtual Tour
1 of 28
$1,750
2

Beds

1.0

Baths

1,048

Sq.Ft.

1812 KILLARNEY DRIVE

Winter Park, FL

Courtesy of EATON REALTY SERVICES
View 677 SELKIRK DRIVE Winter Park, FL MLS# O6433867
  • Virtual Tour
1 of 39
$3,650
3

Beds

2.0

Baths

2,183

Sq.Ft.

677 SELKIRK DRIVE

Winter Park, FL

About Winter Park

Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

Listings in Winter Park, FL

380

Estimated median home price

$697,250
Winter Park FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

Homes for Sale by Price in Winter Park, FL

Price Count
$0 - 100K 4
$100K - 200K 42
$200K - 300K 23
$300K - 400K 13
$400K - 500K 39
$500K - 600K 32
$600K - 700K 39
$700K - 800K 12
$800K - 900K 11
$900K - 1M 11
$1M - Max 154

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 232
Townhouse 23
Condo 81
Commercial 9
Rental 79
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 8/30/2026)

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 8/30/2026.