73 total properties
Did you mean the neighborhood Winter Park?
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

View 4965 ORANGE AVENUE Winter Park, FL MLS# O6423739
  • Recently Listed with Virtual Tour
1 of 29
$379,900
4

Beds

2.0

Baths

1,444

Sq.Ft.

4965 ORANGE AVENUE

Winter Park, FL

View 2973 SANBINA STREET Winter Park, FL MLS# O6407521
$377,880
3

Beds

2.0

Baths

1,128

Sq.Ft.

2973 SANBINA STREET

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 958 DUPONT AVENUE Winter Park, FL MLS# O6371341
$375,000
3

Beds

2.0

Baths

1,572

Sq.Ft.

958 DUPONT AVENUE

Winter Park, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 925 S SEMORAN BOULEVARD 103 Winter Park, FL MLS# O6409391
$373,000
1,454

Sq.Ft.

925 S SEMORAN BOULEVARD 103

Winter Park, FL

View 2889 ROUEN AVENUE Winter Park, FL MLS# L4961275
$365,000
3

Beds

2.0

Baths

1,144

Sq.Ft.

2889 ROUEN AVENUE

Winter Park, FL

View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
$349,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RICK SINGH REAL ESTATE
View 2006 CORNELL AVENUE Winter Park, FL MLS# O6412789
$338,000
2

Beds

1.0

Baths

797

Sq.Ft.

2006 CORNELL AVENUE

Winter Park, FL

Courtesy of FLORIDA HOME TEAM REALTY LLC
View 751 WARRENTON ROAD Winter Park, FL MLS# TB8522073
$319,900
3

Beds

2.0

Baths

1,196

Sq.Ft.

751 WARRENTON ROAD

Winter Park, FL

View 758 WARRENTON ROAD Winter Park, FL MLS# O6395298
$318,985
3

Beds

2.0

Baths

1,196

Sq.Ft.

758 WARRENTON ROAD

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 7500 WAUNATTA COURT Winter Park, FL MLS# TB8525179
$299,900
3

Beds

2.0

Baths

1,998

Sq.Ft.

7500 WAUNATTA COURT

Winter Park, FL

View 311 E MORSE BOULEVARD 7-11 Winter Park, FL MLS# O6337061
$299,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 7-11

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 184 SANDLEWOOD TRAIL #2 Winter Park, FL MLS# O6380753
$299,000
2

Beds

2.1

Baths

1,133

Sq.Ft.

184 SANDLEWOOD TRAIL #2

Winter Park, FL

View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$290,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

View 311 E MORSE BOULEVARD 7-19 Winter Park, FL MLS# O6368912
  • Adult Community with Virtual Tour
1 of 34
$284,900
1

Beds

1.0

Baths

482

Sq.Ft.

311 E MORSE BOULEVARD 7-19

Winter Park, FL

View 311 E MORSE BOULEVARD 6-12 Winter Park, FL MLS# O6413554
$275,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 6-12

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1500 GAY ROAD 18D Winter Park, FL MLS# O6422691
  • Recently Listed with Virtual Tour
1 of 30
$275,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 18D

Winter Park, FL

View 3580 WILDE AVENUE Winter Park, FL MLS# O6296776
$260,000
Studio

Beds

0.0

Baths

3580 WILDE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1500 GAY ROAD 20D Winter Park, FL MLS# O6385626
$258,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 20D

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Adult Community with Virtual Tour
1 of 24
$254,900
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

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

309

Estimated median home price

$725,000
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

PriceCount
$0 - 100K4
$100K - 200K43
$200K - 300K18
$300K - 400K13
$400K - 500K26
$500K - 600K21
$600K - 700K25
$700K - 800K11
$800K - 900K9
$900K - 1M6
$1M - Max133

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family189
Townhouse13
Condo76
Commercial6
Rental70
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 7/9/2026)

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 7/10/2026.