266 total properties
Did you mean the neighborhood Winter Park?
View 3060 GEORGE MASON AVENUE 10C Winter Park, FL MLS# O6371260
$104,900
1

Beds

1.0

Baths

803

Sq.Ft.

3060 GEORGE MASON AVENUE 10C

Winter Park, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 311 E MORSE BOULEVARD 5 Winter Park, FL MLS# O6370558
  • Recently Listed with Virtual Tour
1 of 31
$2,100,000
2

Beds

2.0

Baths

1,900

Sq.Ft.

311 E MORSE BOULEVARD 5

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 860 N DENNING DRIVE Winter Park, FL MLS# O6370723
  • Recently Listed with Virtual Tour
1 of 48
$749,900
3

Beds

2.1

Baths

1,290

Sq.Ft.

860 N DENNING DRIVE

Winter Park, FL

Courtesy of OUTLET REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 636 DUNBLANE DRIVE Winter Park, FL MLS# O6370332
  • Recently Listed with Virtual Tour
1 of 26
$725,000
3

Beds

2.0

Baths

1,803

Sq.Ft.

636 DUNBLANE DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
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
View 731 BONGART ROAD Winter Park, FL MLS# S5140952
  • Recently Listed with Virtual Tour
1 of 28
$570,000
4

Beds

3.0

Baths

1,526

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of MY REALTY GROUP, LLC.
View 637 N PARK AVENUE Winter Park, FL MLS# O6370317
  • Recently Listed with Virtual Tour
1 of 86
$3,895,000
3

Beds

3.2

Baths

4,237

Sq.Ft.

637 N PARK AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1920 WOODCREST DRIVE 9 Winter Park, FL MLS# O6369943
  • Recently Listed
1 of 27
$229,000
2

Beds

2.0

Baths

1,010

Sq.Ft.

1920 WOODCREST DRIVE 9

Winter Park, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1816 AZALEA AVENUE Winter Park, FL MLS# O6369603
  • Recently Listed with Virtual Tour
1 of 26
$369,900
3

Beds

2.0

Baths

1,584

Sq.Ft.

1816 AZALEA AVENUE

Winter Park, FL

Courtesy of GENSTONE REALTY
View 1841 HARLAND PARK DRIVE Winter Park, FL MLS# O6369653
  • Recently Listed with Virtual Tour
1 of 28
$1,999,000
4

Beds

3.1

Baths

3,470

Sq.Ft.

1841 HARLAND PARK DRIVE

Winter Park, FL

Courtesy of SELECTIVE REALTY GROUP LLC
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6369571
  • Recently Listed with Virtual Tour
1 of 19
$499,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6369600
  • Recently Listed with Virtual Tour
1 of 25
$499,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1673 MAYFIELD AVENUE Winter Park, FL MLS# O6369267
  • Recently Listed with Virtual Tour
1 of 44
$1,300,000
4

Beds

4.0

Baths

2,540

Sq.Ft.

1673 MAYFIELD AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 7426 WYNNEWOOD SQUARE 195 Winter Park, FL MLS# O6369034
  • Recently Listed with Virtual Tour
1 of 17
$185,000
3

Beds

2.0

Baths

1,117

Sq.Ft.

7426 WYNNEWOOD SQUARE 195

Winter Park, FL

Courtesy of SPRINGHILL PROPERTIES LLC
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
  • Recently Listed with Virtual Tour
1 of 7
$499,000
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2500 LEE ROAD 222 Winter Park, FL MLS# O6368580
  • Recently Listed
1 of 25
$199,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 222

Winter Park, FL

Courtesy of HOMESMART
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
  • Recently Listed with Virtual Tour
1 of 7
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 126 SCOTTSDALE SQUARE 126 Winter Park, FL MLS# S5140472
  • Recently Listed with Virtual Tour
1 of 25
$99,900
2

Beds

1.1

Baths

1,085

Sq.Ft.

126 SCOTTSDALE SQUARE 126

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 900 CARVER STREET Winter Park, FL MLS# O6368746
$425,000
3

Beds

2.0

Baths

1,794

Sq.Ft.

900 CARVER STREET

Winter Park, FL

Courtesy of LEGACY REALTY & BROKERS LLC
View 851 MILES AVENUE 13 Winter Park, FL MLS# O6368234
  • Recently Listed with Virtual Tour
1 of 24
OPEN HOUSE: Friday 1/9 4:00 PM - 6:00 PM
$219,000
2

Beds

1.0

Baths

808

Sq.Ft.

851 MILES AVENUE 13

Winter Park, FL

Courtesy of LPT 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

267

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 5
$100K - 200K 34
$200K - 300K 20
$300K - 400K 15
$400K - 500K 23
$500K - 600K 20
$600K - 700K 21
$700K - 800K 22
$800K - 900K 4
$900K - 1M 10
$1M - Max 93

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 155
Townhouse 18
Condo 66
Commercial 5
Rental 102
Lots and Land 18
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/6/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

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 1/6/2026.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 1/6/2026.

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 1/6/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 1/6/2026.