12 total properties
Did you mean the neighborhood Winter Park?
View 1417 WILLIAMS DRIVE Winter Park, FL MLS# O6428414
  • Recently Listed with Virtual Tour
1 of 55
OPEN HOUSE: Saturday 8/22 12:00 PM - 3:00 PM
$3,999,000
5

Beds

5.1

Baths

4,891

Sq.Ft.

1417 WILLIAMS DRIVE

Winter Park, FL

View 620 VIRGINIA DRIVE Winter Park, FL MLS# O6432790
  • Recently Listed with Virtual Tour
1 of 11
$3,890,000
6

Beds

5.0

Baths

4,677

Sq.Ft.

620 VIRGINIA DRIVE

Winter Park, FL

View 857 BROCK STREET Winter Park, FL MLS# O6432219
  • Recently Listed with Virtual Tour
1 of 11
$4,650,000
5

Beds

5.1

Baths

4,827

Sq.Ft.

857 BROCK STREET

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 540 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6431538
  • Recently Listed with Virtual Tour
1 of 9
$4,600,000
Studio

Beds

0.0

Baths

540 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1525 GRANVILLE DRIVE Winter Park, FL MLS# O6422951
  • New Construction with Virtual Tour
1 of 56
OPEN HOUSE: Saturday 8/22 12:00 PM - 2:00 PM
$4,750,000
5

Beds

5.1

Baths

5,211

Sq.Ft.

1525 GRANVILLE DRIVE

Winter Park, FL

View 125 S INTERLACHEN AVENUE 1 Winter Park, FL MLS# O6428952
$3,895,000
3

Beds

3.2

Baths

3,878

Sq.Ft.

125 S INTERLACHEN AVENUE 1

Winter Park, FL

Courtesy of COLLADO REAL ESTATE
View 2525 TEMPLE DRIVE Winter Park, FL MLS# O6427787
$4,750,000
5

Beds

4.1

Baths

4,542

Sq.Ft.

2525 TEMPLE DRIVE

Winter Park, FL

View 229 ALEXANDER PLACE Winter Park, FL MLS# O6412911
$4,250,000
4

Beds

4.2

Baths

4,431

Sq.Ft.

229 ALEXANDER PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1441 CARDINAL COURT Winter Park, FL MLS# O6399395
$4,285,000
4

Beds

5.1

Baths

4,066

Sq.Ft.

1441 CARDINAL COURT

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 207 E KINGS WAY Winter Park, FL MLS# O6337304
  • New Construction with Virtual Tour
1 of 6
$3,650,000
5

Beds

4.1

Baths

3,719

Sq.Ft.

207 E KINGS WAY

Winter Park, FL

View 503 N INTERLACHEN AVENUE Winter Park, FL MLS# O6331207
$4,500,000
Studio

Beds

0.0

Baths

503 N INTERLACHEN AVENUE

Winter Park, FL

View 1150 VIA SALERNO Winter Park, FL MLS# O6321143
  • New Construction with Virtual Tour
1 of 64
OPEN HOUSE: Saturday 8/22 12:00 PM - 2:00 PM
$3,975,000
4

Beds

5.1

Baths

3,850

Sq.Ft.

1150 VIA SALERNO

Winter Park, 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

373

Estimated median home price

$695,000
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 - 100K7
$100K - 200K41
$200K - 300K23
$300K - 400K15
$400K - 500K32
$500K - 600K34
$600K - 700K38
$700K - 800K14
$800K - 900K11
$900K - 1M11
$1M - Max147

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family226
Townhouse22
Condo85
Commercial9
Rental80
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 8/22/2026)

Information deemed reliable but not guaranteed.

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 8/23/2026.