111 total properties
Did you mean the neighborhood Winter Park?
View 1543 Lawndale Circle Circle Winter Park, FL MLS# RX11156202
  • Recently Listed with Virtual Tour
1 of 31
$425,000
4

Beds

2.1

Baths

1,840

Sq.Ft.

1543 Lawndale Circle Circle

Winter Park, FL

BeachesMLS
View 1543 LAWNDALE CIRCLE Winter Park, FL MLS# GC536774
  • Recently Listed with Virtual Tour
1 of 31
$425,000
4

Beds

2.1

Baths

1,840

Sq.Ft.

1543 LAWNDALE CIRCLE

Winter Park, FL

Courtesy of ARIUM REAL ESTATE, LLC
View 3220 NETHERWOOD DRIVE Winter Park, FL MLS# O6374172
  • Recently Listed with Virtual Tour
1 of 18
$285,000
2

Beds

2.0

Baths

1,036

Sq.Ft.

3220 NETHERWOOD DRIVE

Winter Park, FL

Courtesy of THE FIRM RE
The time to sell is now! THE TIME TO SELL IS NOW!
View 1695 LEE ROAD B216 Winter Park, FL MLS# O6374448
  • Recently Listed with Virtual Tour
1 of 15
$134,900
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD B216

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2833 PRINCE JOHN ROAD Winter Park, FL MLS# O6374734
  • Recently Listed with Virtual Tour
1 of 43
$429,000
4

Beds

2.0

Baths

1,605

Sq.Ft.

2833 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of EXIT REALTY PREMIER LEGACY
View 1500 GAY ROAD 21-C Winter Park, FL MLS# O6373517
  • Recently Listed with Virtual Tour
1 of 27
$265,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 21-C

Winter Park, FL

Courtesy of REDFIN CORPORATION
View 6980 ALOMA AVENUE 32 Winter Park, FL MLS# O6373864
  • Recently Listed with Virtual Tour
1 of 12
$250,000
900

Sq.Ft.

6980 ALOMA AVENUE 32

Winter Park, FL

Courtesy of APPLE REALTY
View 7468 CANFORD COURT 24 Winter Park, FL MLS# O6373850
  • Recently Listed with Virtual Tour
1 of 49
$205,000
2

Beds

1.1

Baths

1,365

Sq.Ft.

7468 CANFORD COURT 24

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 200 SAINT ANDREWS BOULEVARD 3203 Winter Park, FL MLS# O6373542
  • Recently Listed with Virtual Tour
1 of 30
$225,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 3203

Winter Park, FL

Courtesy of WINTER PARK REAL ESTATE CO LLC
View 1250 S DENNING DRIVE 104 Winter Park, FL MLS# O6371777
  • Recently Listed with Virtual Tour
1 of 23
$230,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 104

Winter Park, FL

Courtesy of SERHANT
View 3136 CROWN JEWEL COURT Winter Park, FL MLS# O6368775
  • Recently Listed with Virtual Tour
1 of 21
$329,000
3

Beds

2.1

Baths

1,408

Sq.Ft.

3136 CROWN JEWEL COURT

Winter Park, FL

Courtesy of REALTY RESOURCE OF CENTRAL FL.
View 690 OSCEOLA AVENUE 503 Winter Park, FL MLS# O6372265
  • Recently Listed with Virtual Tour
1 of 50
$495,000
2

Beds

2.0

Baths

1,148

Sq.Ft.

690 OSCEOLA AVENUE 503

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 200 SAINT ANDREW 3103 Winter Park, FL MLS# S5141362
  • Recently Listed with Virtual Tour
1 of 11
$190,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREW 3103

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 230 STRATHY LANE Winter Park, FL MLS# O6371054
  • Recently Listed with 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
View 2231 NAIRN DRIVE Winter Park, FL MLS# O6369016
  • Recently Listed with Virtual Tour
1 of 19
$499,000
3

Beds

2.0

Baths

1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 1996 INDIANA AVENUE Winter Park, FL MLS# O6372229
  • Recently Listed with Virtual Tour
1 of 18
$249,900
2

Beds

1.0

Baths

818

Sq.Ft.

1996 INDIANA AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 3060 GEORGE MASON AVENUE 10C Winter Park, FL MLS# O6371260
$89,500
1

Beds

1.0

Baths

803

Sq.Ft.

3060 GEORGE MASON AVENUE 10C

Winter Park, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 958 DUPONT AVENUE Winter Park, FL MLS# O6371341
  • Recently Listed with Virtual Tour
1 of 27
$381,000
3

Beds

2.0

Baths

1,572

Sq.Ft.

958 DUPONT AVENUE

Winter Park, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 2500 LEE ROAD 237 Winter Park, FL MLS# V4946519
  • Recently Listed
1 of 23
$169,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 237

Winter Park, FL

Courtesy of LPT REALTY LLC (DB)
View 2002 INDIANA AVENUE Winter Park, FL MLS# GC536284
  • Recently Listed with Virtual Tour
1 of 8
$358,000
Studio

Beds

0.0

Baths

2002 INDIANA AVENUE

Winter Park, FL

Courtesy of DAWN REALTY

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

280

Estimated median home price

$670,000
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 - 100K6
$100K - 200K34
$200K - 300K25
$300K - 400K15
$400K - 500K25
$500K - 600K17
$600K - 700K26
$700K - 800K19
$800K - 900K4
$900K - 1M10
$1M - Max99

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family157
Townhouse20
Condo73
Commercial6
Rental101
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 1/16/2026)

Information deemed reliable but not guaranteed.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 1/21/2026.

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 1/21/2026.