206 total properties
Did you mean the neighborhood Winter Park?
View 962 ARAGON AVENUE Winter Park, FL MLS# O6407916
$599,900
3

Beds

2.0

Baths

1,680

Sq.Ft.

962 ARAGON AVENUE

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
View 2973 SANBINA STREET Winter Park, FL MLS# O6407521
  • Recently Listed with Virtual Tour
1 of 36
$377,880
3

Beds

2.0

Baths

1,128

Sq.Ft.

2973 SANBINA STREET

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 1780 GOODRICH AVENUE Winter Park, FL MLS# O6403811
$625,000
3

Beds

2.0

Baths

1,283

Sq.Ft.

1780 GOODRICH AVENUE

Winter Park, FL

Courtesy of SUMMERPARK HOMES REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2940 DE BROCY WAY Winter Park, FL MLS# O6408085
$785,000
3

Beds

2.0

Baths

2,679

Sq.Ft.

2940 DE BROCY WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 505 CORNWALL ROAD Winter Park, FL MLS# O6408759
  • Recently Listed with Virtual Tour
1 of 42
OPEN HOUSE: Sunday 5/31 12:00 PM - 2:00 PM
$675,000
4

Beds

2.0

Baths

1,813

Sq.Ft.

505 CORNWALL ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
  • Recently Listed with Virtual Tour
1 of 23
$399,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

Courtesy of JC FLORIDA REALTY LLC
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6407540
  • Recently Listed
1 of 39
$719,000
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of ADAIR REALTY INC
View 340 KILLARNEY BAY COURT 4-4 Winter Park, FL MLS# O6407259
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Sunday 5/31 12:00 PM - 3:00 PM
$395,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

340 KILLARNEY BAY COURT 4-4

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 616 FITZWALTER DRIVE Winter Park, FL MLS# O6403982
  • Recently Listed
1 of 30
$595,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

616 FITZWALTER DRIVE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
  • Recently Listed with Virtual Tour
1 of 34
$745,000
2

Beds

3.0

Baths

1,440

Sq.Ft.

408 HOLT AVENUE

Winter Park, FL

Courtesy of THE REAL ESTATE PRINCIPLE, INC
View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
$410,000
3

Beds

2.0

Baths

1,402

Sq.Ft.

7532 AZUREBROOK COURT

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2482 ROXBURY ROAD Winter Park, FL MLS# O6406443
  • Recently Listed with Virtual Tour
1 of 20
$400,000
2

Beds

1.0

Baths

913

Sq.Ft.

2482 ROXBURY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
  • Recently Listed with Virtual Tour
1 of 33
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 731 BONGART ROAD Winter Park, FL MLS# O6406004
  • Recently Listed
1 of 44
OPEN HOUSE: Sunday 5/31 12:00 PM - 2:00 PM
$499,000
4

Beds

3.0

Baths

1,526

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 819 DENSMORE DRIVE Winter Park, FL MLS# O6405658
$375,000
3

Beds

2.0

Baths

1,300

Sq.Ft.

819 DENSMORE DRIVE

Winter Park, FL

Courtesy of DON HARKINS REALTY LLC
View 2500 LEE ROAD 232 Winter Park, FL MLS# O6404916
$164,900
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 232

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 721 DUNBAR STREET Winter Park, FL MLS# O6405338
$399,999
2

Beds

2.0

Baths

1,018

Sq.Ft.

721 DUNBAR STREET

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1695 LEE ROAD E116 Winter Park, FL MLS# O6399346
$125,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E116

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6404545
$800,000
5

Beds

3.0

Baths

2,194

Sq.Ft.

739 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of SERHANT

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

391

Estimated median home price

$785,000
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 - 200K47
$200K - 300K24
$300K - 400K24
$400K - 500K29
$500K - 600K23
$600K - 700K29
$700K - 800K20
$800K - 900K15
$900K - 1M10
$1M - Max168

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family249
Townhouse15
Condo86
Commercial7
Rental77
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 5/27/2026)

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 5/28/2026.

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 5/28/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include 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 5/28/2026.

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 5/28/2026.