130 total properties
Did you mean the neighborhood Winter Park?
View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
  • Virtual Tour
1 of 37
$535,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
  • Virtual Tour
1 of 37
$599,000
4

Beds

3.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 2500 LEE ROAD 220 Winter Park, FL MLS# O6411927
  • Virtual Tour
1 of 28
$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
The time to sell is now! THE TIME TO SELL IS NOW!
View 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
$599,999
0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
  • Virtual Tour
1 of 32
$549,900
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 700 MELROSE AVENUE J24 Winter Park, FL MLS# R4911307
  • Adult Community with Virtual Tour
1 of 28
$350,000
1

Beds

1.0

Baths

987

Sq.Ft.

700 MELROSE AVENUE J24

Winter Park, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
$490,900
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

Courtesy of CAISSA REALTY INVESTMENT INC
View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
  • Virtual Tour
1 of 27
$515,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
  • Virtual Tour
1 of 31
$540,000
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
$524,900
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6386578
  • Adult Community with Virtual Tour
1 of 29
$229,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE REALTY
View 3021 AARON BURR AVENUE 3 Winter Park, FL MLS# S5147382
$140,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3021 AARON BURR AVENUE 3

Winter Park, FL

Courtesy of NAIM REAL ESTATE LLC
View 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
$439,000
3

Beds

2.0

Baths

1,606

Sq.Ft.

950 HANOVER AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1695 LEE ROAD D211 Winter Park, FL MLS# O6396190
  • Virtual Tour
1 of 28
$99,900
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD D211

Winter Park, FL

Courtesy of LOKATION
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$419,000
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP REALTY LLC
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

Courtesy of PREMIER MANAGEMENT GROUP INC
View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
$449,900
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
  • Virtual Tour
1 of 30
$509,900
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
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

Courtesy of PARK TOWN REAL ESTATE LLC

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

359

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 31
$200K - 300K 21
$300K - 400K 16
$400K - 500K 31
$500K - 600K 27
$600K - 700K 31
$700K - 800K 16
$800K - 900K 17
$900K - 1M 13
$1M - Max 152

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 215
Townhouse 24
Condo 76
Commercial 15
Rental 90
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 11/3/2026)

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 11/3/2026.