81 total properties
Did you mean the neighborhood Winter Park?
View 283 SANDLEWOOD TRAIL 3 Winter Park, FL MLS# O6431475
$285,000
2

Beds

2.1

Baths

960

Sq.Ft.

283 SANDLEWOOD TRAIL 3

Winter Park, FL

Courtesy of RE/MAX INNOVATION
View 1695 LEE ROAD D107 Winter Park, FL MLS# O6425124
$180,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD D107

Winter Park, FL

Courtesy of PRIMESTATE REALTY, INC.
View 7413 BELLE RIVER COURT 3 Winter Park, FL MLS# O6430667
$214,900
3

Beds

2.1

Baths

1,151

Sq.Ft.

7413 BELLE RIVER COURT 3

Winter Park, FL

Courtesy of OUTLET REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 669 W COMSTOCK AVENUE Winter Park, FL MLS# TB8535201
$210,000
0.0

Baths

669 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of HOMECOIN.COM
View 1000 S SEMORAN BOULEVARD 305 Winter Park, FL MLS# O6428044
$115,000
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 305

Winter Park, FL

Courtesy of MAINFRAME REAL ESTATE
View 1500 GAY ROAD 4D Winter Park, FL MLS# O6425078
  • Virtual Tour
1 of 15
$159,900
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 4D

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 7450 WYNNEWOOD SQUARE 189 Winter Park, FL MLS# O6425486
$170,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7450 WYNNEWOOD SQUARE 189

Winter Park, FL

Courtesy of REAL ESTATE PROFESSIONALS SE
View 2526 PASSAMONTE DRIVE 10F Winter Park, FL MLS# O6418710
$335,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2526 PASSAMONTE DRIVE 10F

Winter Park, FL

Courtesy of LEGACY CORNERSTONE INC
View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
$368,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

Courtesy of RADIUS REALTY GROUP LLC
View 1000 S SEMORAN BOULEVARD 306 Winter Park, FL MLS# R4911525
$138,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 306

Winter Park, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 1000 S SEMORAN BOULEVARD 404 Winter Park, FL MLS# R4911526
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 404

Winter Park, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 1000 S SEMORAN BOULEVARD 408 Winter Park, FL MLS# R4911527
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 408

Winter Park, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 1000 S SEMORAN BOULEVARD 302 Winter Park, FL MLS# O6428713
$105,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 302

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 7488 WHISPERWOOD DRIVE 28 Winter Park, FL MLS# O6419151
$199,000
2

Beds

2.1

Baths

1,578

Sq.Ft.

7488 WHISPERWOOD DRIVE 28

Winter Park, FL

Courtesy of PARKVIEW REAL ESTATE
View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Virtual Tour
1 of 26
$235,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
$242,400
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

Winter Park, FL

Courtesy of FLAT FEE MLS REALTY
View 151 NORTH ORLANDO AVENUE 142 Winter Park, FL MLS# O6412768
$199,900
1

Beds

1.0

Baths

582

Sq.Ft.

151 NORTH ORLANDO AVENUE 142

Winter Park, FL

Courtesy of CREEGAN GROUP
View 2006 CORNELL AVENUE Winter Park, FL MLS# O6412789
$328,000
2

Beds

1.0

Baths

797

Sq.Ft.

2006 CORNELL AVENUE

Winter Park, FL

Courtesy of FLORIDA HOME TEAM REALTY LLC
View 4798 TANGERINE AVENUE 4798 Winter Park, FL MLS# S5150136
$175,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4798 TANGERINE AVENUE 4798

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 2500 LEE ROAD 220 Winter Park, FL MLS# O6411927
$199,900
2

Beds

1.0

Baths

851

Sq.Ft.

2500 LEE ROAD 220

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS

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

369

Estimated median home price

$745,000
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 - 100K2
$100K - 200K38
$200K - 300K25
$300K - 400K20
$400K - 500K33
$500K - 600K25
$600K - 700K37
$700K - 800K18
$800K - 900K12
$900K - 1M16
$1M - Max143

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family216
Townhouse20
Condo82
Commercial14
Rental93
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 10/14/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of Georgia MLS. Real estate listings held by brokerage firms other than Weichert's are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.

© 2026 Georgia MLS. All rights reserved

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 10/15/2026.