82 total properties
Did you mean the neighborhood Winter Park?
View 623 GRENADINE COURT 623 Winter Park, FL MLS# O6434195
  • Recently Listed with Virtual Tour
1 of 36
$199,900
2

Beds

2.0

Baths

1,037

Sq.Ft.

623 GRENADINE COURT 623

Winter Park, FL

View 7471 CANFORD COURT 19 Winter Park, FL MLS# G5103114
$199,000
2

Beds

1.1

Baths

1,393

Sq.Ft.

7471 CANFORD COURT 19

Winter Park, FL

Courtesy of IAD REAL ESTATE
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

The time to sell is now! THE TIME TO SELL IS NOW!
View 1250 S DENNING DRIVE 109 Winter Park, FL MLS# R4911491
$190,000
1

Beds

1.0

Baths

658

Sq.Ft.

1250 S DENNING DRIVE 109

Winter Park, FL

View 7468 CANFORD COURT 24 Winter Park, FL MLS# O6433680
  • Recently Listed with Virtual Tour
1 of 32
$189,900
2

Beds

1.1

Baths

1,365

Sq.Ft.

7468 CANFORD COURT 24

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2918 ANTIQUE OAKS CIRCLE 25 Winter Park, FL MLS# O6389113
$189,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

2918 ANTIQUE OAKS CIRCLE 25

Winter Park, FL

View 7450 WYNNEWOOD SQUARE 189 Winter Park, FL MLS# O6425486
$185,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7450 WYNNEWOOD SQUARE 189

Winter Park, FL

View 7301 CEDAR CREEK COURT 66 Winter Park, FL MLS# O6397477
$184,950
2

Beds

2.1

Baths

1,031

Sq.Ft.

7301 CEDAR CREEK COURT 66

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 2500 LEE RD. 222 Winter Park, FL MLS# O6368580
$184,900
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE RD. 222

Winter Park, FL

View 3370 CEDAR SPRINGS PLACE 156 Winter Park, FL MLS# O6326460
$182,500
2

Beds

2.1

Baths

1,031

Sq.Ft.

3370 CEDAR SPRINGS PLACE 156

Winter Park, FL

View 2923 ANTIQUE OAKS CIRCLE 34 Winter Park, FL MLS# S5150301
$180,000
2

Beds

2.0

Baths

1,105

Sq.Ft.

2923 ANTIQUE OAKS CIRCLE 34

Winter Park, FL

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 3381 CEDAR SPRINGS PLACE 151 Winter Park, FL MLS# O6419959
$179,900
2

Beds

2.1

Baths

1,031

Sq.Ft.

3381 CEDAR SPRINGS PLACE 151

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6427974
$179,900
2

Beds

2.0

Baths

840

Sq.Ft.

Address not provided

Winter Park, FL

View 2500 LEE ROAD 208 Winter Park, FL MLS# O6297570
$175,000
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 208

Winter Park, FL

View 7327 FOREST HILL COURT 223 Winter Park, FL MLS# O6403841
$175,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7327 FOREST HILL COURT 223

Winter Park, FL

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 3373 CEDAR SPRINGS PLACE 149 Winter Park, FL MLS# O6426224
$171,900
2

Beds

2.1

Baths

1,031

Sq.Ft.

3373 CEDAR SPRINGS PLACE 149

Winter Park, FL

View 1500 GAY ROAD 4D Winter Park, FL MLS# O6425078
  • Virtual Tour
1 of 15
OPEN HOUSE: Sunday 9/6 1:00 PM - 3:00 PM
$169,900
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 4D

Winter Park, FL

View 3651 N N GOLDENROD RD ROAD #C205 Winter Park, FL MLS# O6438227
  • Recently Listed with Virtual Tour
1 of 11
$169,900
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N N GOLDENROD RD ROAD #C205

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

362

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

PriceCount
$0 - 100K3
$100K - 200K41
$200K - 300K22
$300K - 400K15
$400K - 500K37
$500K - 600K28
$600K - 700K37
$700K - 800K11
$800K - 900K10
$900K - 1M9
$1M - Max149

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family221
Townhouse21
Condo79
Commercial9
Rental75
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 9/4/2026)

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 9/4/2026.