93 total properties
Did you mean the neighborhood Winter Park?
View 350 N PHELPS AVENUE Winter Park, FL MLS# O6440072
  • Virtual Tour
1 of 50
$4,677
4

Beds

3.0

Baths

2,267

Sq.Ft.

350 N PHELPS AVENUE

Winter Park, FL

Courtesy of GOYAL & DECOSTER REALTY
View 343 HARRIS DRIVE Winter Park, FL MLS# O6338173
  • Virtual Tour
1 of 42
$4,500
3

Beds

2.0

Baths

2,167

Sq.Ft.

343 HARRIS DRIVE

Winter Park, FL

Courtesy of CLARA HERRERA REALTY
View 2227 HOWARD DRIVE Winter Park, FL MLS# O6452813
  • Virtual Tour
1 of 28
$4,100
3

Beds

2.1

Baths

2,196

Sq.Ft.

2227 HOWARD DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 616 ELLENDALE DRIVE Winter Park, FL MLS# O6428076
  • Virtual Tour
1 of 24
$4,000
4

Beds

2.0

Baths

1,405

Sq.Ft.

616 ELLENDALE DRIVE

Winter Park, FL

Courtesy of BALDWIN PARK REALTY LLC
View 432 W SWOOPE AVENUE Winter Park, FL MLS# O6452364
  • Recently Listed with Virtual Tour
1 of 14
$4,000
4

Beds

3.1

Baths

2,664

Sq.Ft.

432 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 735 MINNESOTA AVENUE Winter Park, FL MLS# O6446889
  • Virtual Tour
1 of 10
$3,995
3

Beds

3.1

Baths

1,810

Sq.Ft.

735 MINNESOTA AVENUE

Winter Park, FL

Courtesy of FLORIDA HOMES SALES & MANAGEMENT LLC
View 737 MINNESOTA AVENUE Winter Park, FL MLS# O6446900
  • Virtual Tour
1 of 10
$3,995
3

Beds

3.1

Baths

1,810

Sq.Ft.

737 MINNESOTA AVENUE

Winter Park, FL

Courtesy of FLORIDA HOMES SALES & MANAGEMENT LLC
View 7797 BROKEN ARROW TRAIL Winter Park, FL MLS# O6450524
  • Recently Listed with Virtual Tour
1 of 54
$3,900
4

Beds

2.0

Baths

2,548

Sq.Ft.

7797 BROKEN ARROW TRAIL

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 1939 GUNN ROAD Winter Park, FL MLS# O6437716
  • Virtual Tour
1 of 28
$3,400
3

Beds

2.0

Baths

1,438

Sq.Ft.

1939 GUNN ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1415 HARMON AVENUE Winter Park, FL MLS# O6448198
  • Virtual Tour
1 of 34
$3,400
3

Beds

2.1

Baths

1,753

Sq.Ft.

1415 HARMON AVENUE

Winter Park, FL

Courtesy of HOST MANAGEMENT GROUP LLC
View 624 LONDON ROAD Winter Park, FL MLS# O6453663
  • Recently Listed with Virtual Tour
1 of 29
$3,350
4

Beds

2.0

Baths

1,908

Sq.Ft.

624 LONDON ROAD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 1409 MICHIGAN AVENUE Winter Park, FL MLS# O6430070
$3,100
3

Beds

2.1

Baths

1,803

Sq.Ft.

1409 MICHIGAN AVENUE

Winter Park, FL

Courtesy of UNIONE REALTY INC
View 424 DUNRAVEN DRIVE Winter Park, FL MLS# O6455413
  • Recently Listed
1 of 14
$3,100
3

Beds

2.0

Baths

1,329

Sq.Ft.

424 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of LOKATION
View 450 W CANTON AVENUE Winter Park, FL MLS# O6434931
  • Virtual Tour
1 of 38
$3,000
3

Beds

2.0

Baths

1,782

Sq.Ft.

450 W CANTON AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 731 BONGART ROAD Winter Park, FL MLS# S5160343
  • Recently Listed
1 of 85
$3,000
4

Beds

3.0

Baths

1,842

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of MY REALTY GROUP, LLC.
View 640 N PARK AVENUE 7 Winter Park, FL MLS# O6455105
  • Recently Listed with Virtual Tour
1 of 19
$3,000
2

Beds

2.0

Baths

900

Sq.Ft.

640 N PARK AVENUE 7

Winter Park, FL

Courtesy of MICHAEL O'SHAUGHNESSY, INC.
View 7033 EASTER STREET Winter Park, FL MLS# O6428828
  • Virtual Tour
1 of 42
$2,850
4

Beds

3.0

Baths

2,151

Sq.Ft.

7033 EASTER STREET

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1051 TURNER ROAD Winter Park, FL MLS# O6450747
  • Recently Listed with Virtual Tour
1 of 11
$2,850
3

Beds

2.0

Baths

1,364

Sq.Ft.

1051 TURNER ROAD

Winter Park, FL

Courtesy of SOGO REAL ESTATE SERVICES LLC
View 957 DUPONT AVENUE Winter Park, FL MLS# O6454336
  • Recently Listed with Virtual Tour
1 of 29
$2,800
3

Beds

2.1

Baths

1,289

Sq.Ft.

957 DUPONT AVENUE

Winter Park, FL

Courtesy of HOME & HIVE REALTY
View 408 LONDON ROAD Winter Park, FL MLS# O6452450
  • Recently Listed with Virtual Tour
1 of 29
$2,740
3

Beds

2.0

Baths

1,295

Sq.Ft.

408 LONDON ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS

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

356

Estimated median home price

$830,500
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 4
$100K - 200K 32
$200K - 300K 23
$300K - 400K 17
$400K - 500K 28
$500K - 600K 27
$600K - 700K 29
$700K - 800K 15
$800K - 900K 17
$900K - 1M 13
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 210
Townhouse 24
Condo 79
Commercial 15
Rental 92
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 11/6/2026)

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 11/6/2026.