281 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 1836 WHITEHALL DRIVE Winter Park, FL MLS# O6416158
  • New Construction with Virtual Tour
1 of 70
$3,500,000
5

Beds

6.1

Baths

4,168

Sq.Ft.

1836 WHITEHALL DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2228 AZALEA PLACE Winter Park, FL MLS# O6416342
  • Recently Listed with Virtual Tour
1 of 72
$5,600,000
5

Beds

5.1

Baths

5,152

Sq.Ft.

2228 AZALEA PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 240 N PHELPS AVENUE Winter Park, FL MLS# O6415360
  • New Construction with Virtual Tour
1 of 39
$2,250,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

View 1113 VIA DEL MAR Winter Park, FL MLS# O6416144
  • Virtual Tour
1 of 9
$1,595,000
Studio

Beds

0.0

Baths

1113 VIA DEL MAR

Winter Park, FL

Courtesy of BAY HILL REALTY LLC
View 275 N RANGER BOULEVARD Winter Park, FL MLS# O6415904
$775,000
4

Beds

3.0

Baths

1,950

Sq.Ft.

275 N RANGER BOULEVARD

Winter Park, FL

View 1473 BERKSHIRE AVENUE Winter Park, FL MLS# O6415098
  • New Construction with Virtual Tour
1 of 38
$1,429,000
5

Beds

4.0

Baths

2,351

Sq.Ft.

1473 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of KARDOSH REALTY
View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Adult Community with Virtual Tour
1 of 24
$254,900
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

Winter Park, FL

View 231 CHELTON CIRCLE Winter Park, FL MLS# O6414890
  • Virtual Tour
1 of 67
$4,950,000
4

Beds

5.2

Baths

5,550

Sq.Ft.

231 CHELTON CIRCLE

Winter Park, FL

View 2032 KIMBRACE PLACE Winter Park, FL MLS# O6414862
  • Virtual Tour
1 of 83
$1,988,888
5

Beds

4.0

Baths

3,382

Sq.Ft.

2032 KIMBRACE PLACE

Winter Park, FL

View 2715 PRINCE JOHN ROAD Winter Park, FL MLS# O6415084
$498,900
3

Beds

2.0

Baths

1,565

Sq.Ft.

2715 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of VIA PROPERTIES LLC
View 413 W MORSE BOULEVARD Winter Park, FL MLS# O6412134
$2,695,000
3

Beds

3.1

Baths

3,048

Sq.Ft.

413 W MORSE BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2974 CHANTILLY AVENUE Winter Park, FL MLS# O6412851
$499,000
3

Beds

2.0

Baths

1,433

Sq.Ft.

2974 CHANTILLY AVENUE

Winter Park, FL

View 2240 VENETIAN WAY Winter Park, FL MLS# O6413398
  • Virtual Tour
1 of 27
$3,500,000
4

Beds

3.1

Baths

4,036

Sq.Ft.

2240 VENETIAN WAY

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2831 MULFORD AVENUE Winter Park, FL MLS# O6414319
  • Virtual Tour
1 of 28
$715,000
4

Beds

2.1

Baths

1,647

Sq.Ft.

2831 MULFORD AVENUE

Winter Park, FL

View 230 E ROCKWOOD WAY Winter Park, FL MLS# O6412857
  • Virtual Tour
1 of 59
$2,189,000
5

Beds

4.0

Baths

3,374

Sq.Ft.

230 E ROCKWOOD WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 151 NORTH ORLANDO AVENUE 142 Winter Park, FL MLS# O6412768
$199,900
1

Beds

1.0

Baths

582

Sq.Ft.

151 NORTH ORLANDO AVENUE 142

Winter Park, FL

View 528 SAINT DUNSTAN WAY Winter Park, FL MLS# O6414677
$524,990
3

Beds

2.0

Baths

1,656

Sq.Ft.

528 SAINT DUNSTAN WAY

Winter Park, FL

View 685 OVERSPIN DRIVE Winter Park, FL MLS# O6415537
$629,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

685 OVERSPIN DRIVE

Winter Park, FL

View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
  • Virtual Tour
1 of 37
$560,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC

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

273

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

Price Count
$0 - 100K 5
$100K - 200K 40
$200K - 300K 17
$300K - 400K 14
$400K - 500K 24
$500K - 600K 19
$600K - 700K 22
$700K - 800K 12
$800K - 900K 8
$900K - 1M 4
$1M - Max 108

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 158
Townhouse 10
Condo 70
Commercial 7
Rental 73
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/12/2026)

Information deemed reliable but not guaranteed.

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.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

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 7/13/2026.

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 7/13/2026.