102 total properties
Did you mean the neighborhood Winter Park?
View 7417 DANIEL WEBSTER DRIVE 3 Winter Park, FL MLS# O6343221
$1,100
Studio

Beds

1.0

Baths

546

Sq.Ft.

7417 DANIEL WEBSTER DRIVE 3

Winter Park, FL

Courtesy of ROMAN'S PRO REALTY LLC
View 2948 ANTIQUE OAKS CIRCLE 94 Winter Park, FL MLS# O6363775
$1,250
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 1436 MINNESOTA AVENUE Winter Park, FL MLS# O6359812
$1,295
2

Beds

1.0

Baths

805

Sq.Ft.

1436 MINNESOTA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
The time to sell is now! THE TIME TO SELL IS NOW!
View 2183 CRANDON AVENUE 1/2 Winter Park, FL MLS# O6365087
$1,295
2

Beds

1.0

Baths

600

Sq.Ft.

2183 CRANDON AVENUE 1/2

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 3044 ANTIQUE OAKS CIRCLE 178 Winter Park, FL MLS# O6353147
$1,299
1

Beds

1.0

Baths

749

Sq.Ft.

3044 ANTIQUE OAKS CIRCLE 178

Winter Park, FL

Courtesy of 407 PROPERTIES
View 3060 GEORGE MASON AVENUE 10C Winter Park, FL MLS# O6365124
$1,300
1

Beds

1.0

Baths

803

Sq.Ft.

3060 GEORGE MASON AVENUE 10C

Winter Park, FL

Courtesy of PRISTINE INTERNATIONAL REALTY LLC
View 3651 N GOLDENROD ROAD B#104 Winter Park, FL MLS# O6353028
$1,350
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD B#104

Winter Park, FL

Courtesy of JCL REALTY INC
View 4860 TANGERINE AVENUE 4860 Winter Park, FL MLS# S5137370
$1,350
1

Beds

1.0

Baths

753

Sq.Ft.

4860 TANGERINE AVENUE 4860

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 3045 AARON BURR AVENUE 10 Winter Park, FL MLS# S5140420
  • Recently Listed with Virtual Tour
1 of 25
$1,350
1

Beds

1.0

Baths

803

Sq.Ft.

3045 AARON BURR AVENUE 10

Winter Park, FL

Courtesy of TBO REAL ESTATE PARTNERS INC
View 3011 GEORGE MASON AVENUE 3 Winter Park, FL MLS# O6368606
  • Recently Listed with Virtual Tour
1 of 15
$1,395
2

Beds

2.0

Baths

1,056

Sq.Ft.

3011 GEORGE MASON AVENUE 3

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1502 MICHIGAN AVENUE B Winter Park, FL MLS# O6355069
$1,399
2

Beds

1.0

Baths

660

Sq.Ft.

1502 MICHIGAN AVENUE B

Winter Park, FL

Courtesy of 407 PROPERTIES
View 7229 SWALLOW RUN 7229 Winter Park, FL MLS# O6347664
$1,400
2

Beds

2.0

Baths

756

Sq.Ft.

7229 SWALLOW RUN 7229

Winter Park, FL

Courtesy of URBAN-O REAL ESTATE SOLUTIONS
View 200 ST ANDREWS BOULEVARD 601 Winter Park, FL MLS# O6364892
$1,400
1

Beds

1.0

Baths

727

Sq.Ft.

200 ST ANDREWS BOULEVARD 601

Winter Park, FL

Courtesy of HOST MANAGEMENT GROUP LLC
View 3007 GEORGE MASON AVENUE H-3D Winter Park, FL MLS# S5126039
$1,425
2

Beds

2.1

Baths

1,090

Sq.Ft.

3007 GEORGE MASON AVENUE H-3D

Winter Park, FL

Courtesy of ALLEGIANT MANAGEMENT GROUP INC
View 1000 S SEMORAN BOULEVARD 115 Winter Park, FL MLS# O6312697
$1,450
2

Beds

2.0

Baths

1,003

Sq.Ft.

1000 S SEMORAN BOULEVARD 115

Winter Park, FL

Courtesy of MAYERS REAL ESTATE LLC
View 2500 LEE ROAD 244 Winter Park, FL MLS# O6344785
  • Virtual Tour
1 of 26
$1,475
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 244

Winter Park, FL

Courtesy of RE/MAX VANTAGE
View 1250 S DENNING DRIVE 208 Winter Park, FL MLS# O6368688
  • Recently Listed with Virtual Tour
1 of 7
$1,475
1

Beds

1.0

Baths

653

Sq.Ft.

1250 S DENNING DRIVE 208

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 3651 N GOLDENROD ROAD C204 Winter Park, FL MLS# O6367623
  • Recently Listed with Virtual Tour
1 of 14
$1,495
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD C204

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1695 LEE ROAD B114 Winter Park, FL MLS# O6297071
  • Virtual Tour
1 of 23
$1,500
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD B114

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 316 SCOTTSDALE SQUARE 316 Winter Park, FL MLS# O6320930
$1,550
2

Beds

1.1

Baths

1,085

Sq.Ft.

316 SCOTTSDALE SQUARE 316

Winter Park, FL

Courtesy of JADE KEY REALTY 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

279

Estimated median home price

$679,000
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 6
$100K - 200K 35
$200K - 300K 20
$300K - 400K 16
$400K - 500K 24
$500K - 600K 22
$600K - 700K 21
$700K - 800K 22
$800K - 900K 4
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 162
Townhouse 19
Condo 68
Commercial 5
Rental 108
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/3/2026)

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 1/4/2026.