42 total properties
Did you mean the neighborhood Winter Park?
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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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

Courtesy of MAINFRAME REAL ESTATE
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 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 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
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

Courtesy of EXP REALTY LLC
View 3371 RIVER VIEW WAY 46 Winter Park, FL MLS# O6403947
$205,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

3371 RIVER VIEW WAY 46

Winter Park, FL

Courtesy of REALTY ONE GROUP EVOLVE
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

Courtesy of M L VAZ REALTY INC
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 7300 DANIEL WEBSTER DRIVE M7 Winter Park, FL MLS# O6388668
$159,000
2

Beds

2.1

Baths

1,108

Sq.Ft.

7300 DANIEL WEBSTER DRIVE M7

Winter Park, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
View 3027 AARON BURR AVENUE L1 Winter Park, FL MLS# O6390662
$159,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3027 AARON BURR AVENUE L1

Winter Park, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
View 2500 LEE RD. 222 Winter Park, FL MLS# O6368580
$184,400
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE RD. 222

Winter Park, FL

Courtesy of HOMESMART
View 311 SCOTTSDALE SQUARE 311 Winter Park, FL MLS# O6355536
$109,400
1

Beds

1.0

Baths

785

Sq.Ft.

311 SCOTTSDALE SQUARE 311

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2948 ANTIQUE OAKS CIRCLE 94 Winter Park, FL MLS# O6342254
$150,000
1

Beds

1.0

Baths

749

Sq.Ft.

2948 ANTIQUE OAKS CIRCLE 94

Winter Park, FL

Courtesy of THE PAMPAS REAL ESTATE GROUP, LLC.
View 3370 CEDAR SPRINGS PLACE 156 Winter Park, FL MLS# O6326460
$179,990
2

Beds

2.1

Baths

1,031

Sq.Ft.

3370 CEDAR SPRINGS PLACE 156

Winter Park, FL

Courtesy of SPRINGHILL PROPERTIES 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

373

Estimated median home price

$750,000
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 - 200K39
$200K - 300K25
$300K - 400K19
$400K - 500K32
$500K - 600K23
$600K - 700K36
$700K - 800K22
$800K - 900K11
$900K - 1M15
$1M - Max149

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family220
Townhouse21
Condo81
Commercial14
Rental91
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 10/9/2026)

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 10/12/2026.