Winter Park Florida Homes for Rent

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94 total properties
Did you mean the neighborhood Winter Park?
View 7314 SWALLOW RUN 7314 Winter Park, FL MLS# O6455843
  • Recently Listed with Virtual Tour
1 of 33
$1,495
2

Beds

2.0

Baths

775

Sq.Ft.

7314 SWALLOW RUN 7314

Winter Park, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 1695 LEE ROAD B102 Winter Park, FL MLS# O6455096
  • Recently Listed with Virtual Tour
1 of 49
$1,850
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD B102

Winter Park, FL

Courtesy of LA ROSA REALTY PREMIER LLC
View 2940 PARKLAND DRIVE Winter Park, FL MLS# O6453330
  • Recently Listed with Virtual Tour
1 of 12
$3,000
3

Beds

1.0

Baths

950

Sq.Ft.

2940 PARKLAND DRIVE

Winter Park, FL

Courtesy of SOTERA LIVING
The time to sell is now! THE TIME TO SELL IS NOW!
View 424 DUNRAVEN DRIVE Winter Park, FL MLS# O6455413
  • Recently Listed
1 of 14
$3,100
3

Beds

2.0

Baths

1,329

Sq.Ft.

424 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of LOKATION
View 640 N PARK AVENUE 7 Winter Park, FL MLS# O6455105
  • Recently Listed with Virtual Tour
1 of 19
$3,000
2

Beds

2.0

Baths

900

Sq.Ft.

640 N PARK AVENUE 7

Winter Park, FL

Courtesy of MICHAEL O'SHAUGHNESSY, INC.
View 651 TRINIDAD COURT 651 Winter Park, FL MLS# O6455493
  • Recently Listed with Virtual Tour
1 of 25
$1,450
1

Beds

1.0

Baths

759

Sq.Ft.

651 TRINIDAD COURT 651

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 1440 MICHIGAN AVENUE Winter Park, FL MLS# O6454851
  • Recently Listed with Virtual Tour
1 of 14
$2,400
2

Beds

2.0

Baths

1,137

Sq.Ft.

1440 MICHIGAN AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2417 LAFAYETTE AVENUE Winter Park, FL MLS# O6454750
  • Recently Listed with Virtual Tour
1 of 31
$10,000
4

Beds

3.0

Baths

2,150

Sq.Ft.

2417 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 3651 N GOLDENROD ROAD B102 Winter Park, FL MLS# O6454593
  • Recently Listed with Virtual Tour
1 of 16
$1,500
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD B102

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1271 MILLER AVENUE Winter Park, FL MLS# O6454354
  • Recently Listed with Virtual Tour
1 of 27
$1,550
1

Beds

1.0

Baths

725

Sq.Ft.

1271 MILLER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 957 DUPONT AVENUE Winter Park, FL MLS# O6454336
  • Recently Listed with Virtual Tour
1 of 29
$2,800
3

Beds

2.1

Baths

1,289

Sq.Ft.

957 DUPONT AVENUE

Winter Park, FL

Courtesy of HOME & HIVE REALTY
View 1695 LEE ROAD C206 Winter Park, FL MLS# TB8562929
  • Recently Listed with Virtual Tour
1 of 21
$1,450
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD C206

Winter Park, FL

Courtesy of INVESTMENT REALTY
View 851 MILES AVENUE 11 Winter Park, FL MLS# O6454285
  • Recently Listed with Virtual Tour
1 of 16
$1,500
2

Beds

1.0

Baths

808

Sq.Ft.

851 MILES AVENUE 11

Winter Park, FL

Courtesy of MAY HO REALTY
View 624 LONDON ROAD Winter Park, FL MLS# O6453663
  • Recently Listed with Virtual Tour
1 of 29
$3,350
4

Beds

2.0

Baths

1,908

Sq.Ft.

624 LONDON ROAD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 1250 S DENNING DRIVE 121 Winter Park, FL MLS# O6453710
  • Recently Listed with Virtual Tour
1 of 10
$1,450
1

Beds

1.0

Baths

653

Sq.Ft.

1250 S DENNING DRIVE 121

Winter Park, FL

Courtesy of CENTRAL FLORIDA REALTY, INC.
View 1000 S SEMORAN BOULEVARD 508 Winter Park, FL MLS# O6447708
  • Recently Listed with Virtual Tour
1 of 21
$1,550
2

Beds

2.0

Baths

1,049

Sq.Ft.

1000 S SEMORAN BOULEVARD 508

Winter Park, FL

Courtesy of PREMIUM PROPERTIES R.E SERVICE
View 731 BONGART ROAD Winter Park, FL MLS# S5160343
  • Recently Listed
1 of 85
$3,000
4

Beds

3.0

Baths

1,842

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of MY REALTY GROUP, LLC.
View 4818 TANGERINE AVENUE 4818 Winter Park, FL MLS# O6451903
$1,400
1

Beds

1.0

Baths

753

Sq.Ft.

4818 TANGERINE AVENUE 4818

Winter Park, FL

Courtesy of BENCHMARK REAL ESTATE GRP INC
View 2250 LEE ROAD 200 Winter Park, FL MLS# O6452334
  • Recently Listed with Virtual Tour
1 of 25
$76,500
17,600

Sq.Ft.

2250 LEE ROAD 200

Winter Park, FL

Courtesy of INNOVATIVE REALTY, LLC
View 2227 HOWARD DRIVE Winter Park, FL MLS# O6452813
  • Virtual Tour
1 of 28
$4,100
3

Beds

2.1

Baths

2,196

Sq.Ft.

2227 HOWARD DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC

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

356

Estimated median home price

$825,000
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 32
$200K - 300K 23
$300K - 400K 17
$400K - 500K 28
$500K - 600K 27
$600K - 700K 29
$700K - 800K 16
$800K - 900K 16
$900K - 1M 13
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 210
Townhouse 24
Condo 79
Commercial 15
Rental 94
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 11/7/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 11/7/2026.