79 total properties
Did you mean the neighborhood Winter Park?
View 1235 VIA ESTRELLA Winter Park, FL MLS# O6388913
  • Virtual Tour
1 of 14
$5,895
4

Beds

3.0

Baths

2,207

Sq.Ft.

1235 VIA ESTRELLA

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1441 ONECO AVENUE Winter Park, FL MLS# O6395705
  • Virtual Tour
1 of 35
$5,700
4

Beds

3.1

Baths

2,531

Sq.Ft.

1441 ONECO AVENUE

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
View 1776 MONDRIAN CIRCLE Winter Park, FL MLS# O6400199
  • New Construction with Virtual Tour
1 of 44
$5,500
3

Beds

3.1

Baths

2,193

Sq.Ft.

1776 MONDRIAN CIRCLE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 784 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6408937
  • Recently Listed with Virtual Tour
1 of 29
$5,500
3

Beds

2.1

Baths

1,940

Sq.Ft.

784 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 782 S PENNSYLVANIA AVENUE 1 Winter Park, FL MLS# O6380197
$5,490
3

Beds

2.1

Baths

2,354

Sq.Ft.

782 S PENNSYLVANIA AVENUE 1

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 1119 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6411654
  • Recently Listed with Virtual Tour
1 of 31
$5,200
4

Beds

3.0

Baths

3,000

Sq.Ft.

1119 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2344 WOODCREST DRIVE Winter Park, FL MLS# O6410619
  • Recently Listed with Virtual Tour
1 of 15
$4,100
4

Beds

2.0

Baths

1,764

Sq.Ft.

2344 WOODCREST DRIVE

Winter Park, FL

Courtesy of EXPLORE FLORIDA REALTY SERVICES LLC
View 1815 BARKER DRIVE Winter Park, FL MLS# O6386321
  • Virtual Tour
1 of 89
$4,000
4

Beds

2.0

Baths

1,548

Sq.Ft.

1815 BARKER DRIVE

Winter Park, FL

Courtesy of SOTERA LIVING
View 7864 BROKEN ARROW TRAIL Winter Park, FL MLS# O6406209
  • Recently Listed
1 of 27
$3,600
4

Beds

2.1

Baths

2,219

Sq.Ft.

7864 BROKEN ARROW TRAIL

Winter Park, FL

Courtesy of LOKATION
View 2115 SYCAMORE DRIVE Winter Park, FL MLS# O6398548
  • Virtual Tour
1 of 23
$3,500
4

Beds

2.0

Baths

2,099

Sq.Ft.

2115 SYCAMORE DRIVE

Winter Park, FL

Courtesy of STOCKWORTH REALTY GROUP
View 1850 WHITEHALL DRIVE Winter Park, FL MLS# O6385792
  • Virtual Tour
1 of 32
$3,475
3

Beds

2.0

Baths

1,670

Sq.Ft.

1850 WHITEHALL DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1937 STRATHAVEN ROAD Winter Park, FL MLS# O6408613
  • Recently Listed
1 of 30
$3,395
3

Beds

2.0

Baths

1,570

Sq.Ft.

1937 STRATHAVEN ROAD

Winter Park, FL

Courtesy of VIA PROPERTIES LLC
View 952 FAIRWAY DRIVE Winter Park, FL MLS# G5109152
  • Virtual Tour
1 of 24
$3,300
3

Beds

2.0

Baths

2,007

Sq.Ft.

952 FAIRWAY DRIVE

Winter Park, FL

Courtesy of THE FLORIDA PROPERTY SHOP SALE
View 438 LAKEVIEW AVENUE Winter Park, FL MLS# O6396001
  • Virtual Tour
1 of 24
$3,200
2

Beds

1.0

Baths

1,250

Sq.Ft.

438 LAKEVIEW AVENUE

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 1830 STAUNTON AVENUE Winter Park, FL MLS# O6401708
  • Adult Community with Virtual Tour
1 of 14
$3,200
3

Beds

2.1

Baths

1,590

Sq.Ft.

1830 STAUNTON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2428 LOTAFUN AVENUE Winter Park, FL MLS# O6401871
  • Adult Community with Virtual Tour
1 of 7
$3,200
3

Beds

2.1

Baths

1,534

Sq.Ft.

2428 LOTAFUN AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 653 SYMONDS AVENUE Winter Park, FL MLS# O6400011
  • Virtual Tour
1 of 17
$3,200
3

Beds

2.1

Baths

1,536

Sq.Ft.

653 SYMONDS AVENUE

Winter Park, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 640 N PARK AVENUE 5 Winter Park, FL MLS# O6411306
  • Recently Listed
1 of 23
$3,200
1

Beds

1.0

Baths

673

Sq.Ft.

640 N PARK AVENUE 5

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1415 HARMON AVENUE Winter Park, FL MLS# O6407290
  • Recently Listed with Virtual Tour
1 of 36
$3,060
3

Beds

2.1

Baths

1,700

Sq.Ft.

1415 HARMON AVENUE

Winter Park, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 4033 YACHT COURT Winter Park, FL MLS# O6396599
  • Virtual Tour
1 of 35
$3,000
4

Beds

2.0

Baths

2,268

Sq.Ft.

4033 YACHT COURT

Winter Park, FL

Courtesy of NEXTHOME NEIGHBORHOOD REALTY

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

398

Estimated median home price

$812,500
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 3
$100K - 200K 45
$200K - 300K 24
$300K - 400K 26
$400K - 500K 28
$500K - 600K 22
$600K - 700K 30
$700K - 800K 21
$800K - 900K 15
$900K - 1M 10
$1M - Max 174

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 257
Townhouse 14
Condo 86
Commercial 7
Rental 81
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/29/2026)

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

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.

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 5/30/2026.