11 total properties
Did you mean the neighborhood Winter Park?
View 1600 LEGION DRIVE Winter Park, FL MLS# O6415591
  • Virtual Tour
1 of 70
$3,995,000
5

Beds

5.1

Baths

4,483

Sq.Ft.

1600 LEGION DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 650 DIXIE PARKWAY Winter Park, FL MLS# O6408708
  • Virtual Tour
1 of 85
$4,250,000
6

Beds

6.1

Baths

6,007

Sq.Ft.

650 DIXIE PARKWAY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 141 W LAKE SUE AVENUE Winter Park, FL MLS# O6406437
  • New Construction with Virtual Tour
1 of 5
$4,200,000
5

Beds

5.2

Baths

5,500

Sq.Ft.

141 W LAKE SUE AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1298 BEACHVIEW AVENUE Winter Park, FL MLS# O6405064
$4,200,000
Studio

Beds

0.0

Baths

1298 BEACHVIEW AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 1441 CARDINAL COURT Winter Park, FL MLS# O6399395
  • Virtual Tour
1 of 85
$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 150 DANA WAY Winter Park, FL MLS# O6394012
  • New Construction with Virtual Tour
1 of 81
$3,799,000
5

Beds

5.0

Baths

4,451

Sq.Ft.

150 DANA WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1782 PINE AVENUE Winter Park, FL MLS# O6389039
  • New Construction
1 of 70
$3,875,000
5

Beds

6.1

Baths

4,782

Sq.Ft.

1782 PINE AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
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

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1161 VALENCIA AVENUE Winter Park, FL MLS# O6330736
  • Virtual Tour
1 of 65
$3,995,000
4

Beds

4.1

Baths

4,181

Sq.Ft.

1161 VALENCIA AVENUE

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

Courtesy of KELLY PRICE & COMPANY LLC
View 1150 VIA SALERNO Winter Park, FL MLS# O6321143
  • New Construction with Virtual Tour
1 of 62
$4,195,000
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

388

Estimated median home price

$750,000
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 4
$100K - 200K 43
$200K - 300K 27
$300K - 400K 17
$400K - 500K 32
$500K - 600K 28
$600K - 700K 34
$700K - 800K 16
$800K - 900K 12
$900K - 1M 9
$1M - Max 166

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 249
Townhouse 17
Condo 88
Commercial 7
Rental 71
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/6/2026)

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 7/6/2026.