118 total properties
Did you mean the neighborhood Winter Park?
View Address not provided Winter Park, FL MLS# S5145631
$430,000
4

Beds

2.0

Baths

1,296

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of EXP REALTY LLC
View 7336 FOREST HILL COURT 240 Winter Park, FL MLS# O6386461
$169,900
2

Beds

1.1

Baths

990

Sq.Ft.

7336 FOREST HILL COURT 240

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 4768 TANGERINE AVENUE 4768 Winter Park, FL MLS# S5144503
$174,900
1

Beds

1.0

Baths

753

Sq.Ft.

4768 TANGERINE AVENUE 4768

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 715 Winter Park, FL MLS# S5144243
$122,990
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 715

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 2924 ANTIQUE OAKS CIRCLE 46 Winter Park, FL MLS# S5144196
$195,000
2

Beds

2.0

Baths

1,105

Sq.Ft.

2924 ANTIQUE OAKS CIRCLE 46

Winter Park, FL

Courtesy of CENTURY 21 EDGE
View 1695 LEE ROAD E215 Winter Park, FL MLS# O6383089
$149,990
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E215

Winter Park, FL

Courtesy of FOWLKES REALTY CO
View 4033 YACHT COURT Winter Park, FL MLS# O6379135
  • Virtual Tour
1 of 26
$549,000
3

Beds

2.0

Baths

2,268

Sq.Ft.

4033 YACHT COURT

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
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 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
$475,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
$544,900
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

View 1695 LEE ROAD B210 Winter Park, FL MLS# O6375872
$95,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B210

Winter Park, FL

View 1809 HAMMERLIN AVENUE Winter Park, FL MLS# O6373616
$549,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1809 HAMMERLIN AVENUE

Winter Park, FL

View 230 STRATHY LANE Winter Park, FL MLS# O6371054
  • Virtual Tour
1 of 12
$499,000
2

Beds

1.0

Baths

920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

View 2231 NAIRN DRIVE Winter Park, FL MLS# O6369016
  • Virtual Tour
1 of 19
$499,000
3

Beds

2.0

Baths

1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

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 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
$459,900
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
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 311 E MORSE BOULEVARD 7-19 Winter Park, FL MLS# O6368912
  • Adult Community with Virtual Tour
1 of 27
$284,900
1

Beds

1.0

Baths

482

Sq.Ft.

311 E MORSE BOULEVARD 7-19

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

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

283

Estimated median home price

$695,000
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 - 100K5
$100K - 200K40
$200K - 300K17
$300K - 400K15
$400K - 500K24
$500K - 600K20
$600K - 700K23
$700K - 800K12
$800K - 900K10
$900K - 1M4
$1M - Max113

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family165
Townhouse13
Condo70
Commercial7
Rental71
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 7/13/2026)

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 7/14/2026.