31 total properties
Did you mean the neighborhood Winter Park?
View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
  • Recently Listed with Virtual Tour
1 of 34
$579,999
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 326 FITZHUGH ROAD Winter Park, FL MLS# O6372053
  • Recently Listed with Virtual Tour
1 of 45
OPEN HOUSE: Sunday 1/25 1:00 PM - 3:00 PM
$475,000
4

Beds

3.0

Baths

1,835

Sq.Ft.

326 FITZHUGH ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 535 N INTERLACHEN AVENUE 106 Winter Park, FL MLS# O6376040
  • Recently Listed with Virtual Tour
1 of 22
$595,000
2

Beds

2.0

Baths

970

Sq.Ft.

535 N INTERLACHEN AVENUE 106

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 7618 WAUNATTA COURT Winter Park, FL MLS# V4946886
  • Recently Listed with Virtual Tour
1 of 31
$465,000
3

Beds

3.0

Baths

1,970

Sq.Ft.

7618 WAUNATTA COURT

Winter Park, FL

Courtesy of PHOENIX REALTY ADVISORS LLC
View 423 OLOLU DRIVE Winter Park, FL MLS# O6369976
  • Recently Listed with Virtual Tour
1 of 51
OPEN HOUSE: Sunday 1/25 1:00 PM - 3:00 PM
$599,000
3

Beds

3.0

Baths

1,920

Sq.Ft.

423 OLOLU DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
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 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 731 BONGART ROAD Winter Park, FL MLS# S5140952
  • 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 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
  • Virtual Tour
1 of 7
$499,000
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2350 CADY WAY Winter Park, FL MLS# O6367536
  • Virtual Tour
1 of 31
OPEN HOUSE: Sunday 1/25 2:00 PM - 4:00 PM
$575,000
4

Beds

2.0

Baths

1,854

Sq.Ft.

2350 CADY WAY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2042 YORKSHIRE DRIVE Winter Park, FL MLS# O6359841
  • Virtual Tour
1 of 33
$499,000
3

Beds

2.0

Baths

1,573

Sq.Ft.

2042 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 422 S RANGER BOULEVARD Winter Park, FL MLS# O6359171
$509,900
4

Beds

2.0

Baths

1,680

Sq.Ft.

422 S RANGER BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1451 Cavendish Road Winter Park, FL MLS# RX11136600
$619,500
3

Beds

2.0

Baths

1,437

Sq.Ft.

1451 Cavendish Road

Winter Park, FL

BeachesMLS
View 2412 MIDDLETON AVENUE Winter Park, FL MLS# O6356193
$549,000
3

Beds

2.0

Baths

1,340

Sq.Ft.

2412 MIDDLETON AVENUE

Winter Park, FL

Courtesy of REAL ESTATE INVESTMENTS BY BOR
View 3312 HEARTWOOD AVENUE Winter Park, FL MLS# O6352582
$540,000
4

Beds

3.0

Baths

2,878

Sq.Ft.

3312 HEARTWOOD AVENUE

Winter Park, FL

Courtesy of MID-STATE PROPERTIES PSL LLC
View 265 E CANTON AVENUE GE Winter Park, FL MLS# O6352115
$605,000
2

Beds

2.0

Baths

1,057

Sq.Ft.

265 E CANTON AVENUE GE

Winter Park, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 346 S RANGER BOULEVARD Winter Park, FL MLS# S5134662
$505,000
3

Beds

2.0

Baths

1,592

Sq.Ft.

346 S RANGER BOULEVARD

Winter Park, FL

Courtesy of IMPERIAL REALTY OF FLORIDA INC
View 1875 STAUNTON AVENUE Winter Park, FL MLS# O6342876
  • Virtual Tour
1 of 16
$560,000
4

Beds

2.0

Baths

2,036

Sq.Ft.

1875 STAUNTON AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 720 W WEBSTER AVENUE Winter Park, FL MLS# O6338765
  • Virtual Tour
1 of 22
$550,000
3

Beds

2.0

Baths

1,356

Sq.Ft.

720 W WEBSTER AVENUE

Winter Park, FL

Courtesy of THE AGENCY FL

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

289

Estimated median home price

$650,000
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 29
$300K - 400K 16
$400K - 500K 27
$500K - 600K 16
$600K - 700K 25
$700K - 800K 19
$800K - 900K 4
$900K - 1M 9
$1M - Max 103

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 161
Townhouse 19
Condo 77
Commercial 6
Rental 98
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/22/2026)

Information deemed reliable but not guaranteed.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

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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 1/26/2026.

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 1/26/2026.