363 total properties
Did you mean the neighborhood Winter Park?
View 620 VIRGINIA DRIVE Winter Park, FL MLS# O6432790
  • New Construction with Virtual Tour
1 of 11
$3,890,000
6

Beds

5.0

Baths

4,677

Sq.Ft.

620 VIRGINIA DRIVE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1742 TEMPLE DRIVE Winter Park, FL MLS# O6443437
  • New Construction with Virtual Tour
1 of 41
$3,695,999
4

Beds

5.0

Baths

3,658

Sq.Ft.

1742 TEMPLE DRIVE

Winter Park, FL

Courtesy of ROI AVE LLC
View 125 S INTERLACHEN AVENUE 1 Winter Park, FL MLS# O6428952
$3,695,000
3

Beds

3.2

Baths

3,878

Sq.Ft.

125 S INTERLACHEN AVENUE 1

Winter Park, FL

Courtesy of COLLADO REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 276 DETMAR DRIVE Winter Park, FL MLS# O6434825
  • Virtual Tour
1 of 81
$3,600,000
4

Beds

5.0

Baths

4,202

Sq.Ft.

276 DETMAR DRIVE

Winter Park, FL

Courtesy of CALL IT CLOSED INTL REALTY
View 2240 VENETIAN WAY Winter Park, FL MLS# O6413398
  • Virtual Tour
1 of 25
$3,500,000
4

Beds

3.1

Baths

4,036

Sq.Ft.

2240 VENETIAN WAY

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 662 GRANVILLE DRIVE Winter Park, FL MLS# O6442030
  • Virtual Tour
1 of 78
$3,495,000
5

Beds

5.1

Baths

4,478

Sq.Ft.

662 GRANVILLE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1600 LEGION DRIVE Winter Park, FL MLS# O6450869
  • Recently Listed with Virtual Tour
1 of 76
$3,495,000
5

Beds

5.1

Baths

4,483

Sq.Ft.

1600 LEGION DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 160 W ROCKWOOD WAY Winter Park, FL MLS# O6437722
  • Virtual Tour
1 of 72
$3,395,000
5

Beds

5.1

Baths

4,015

Sq.Ft.

160 W ROCKWOOD WAY

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1751 GLENCOE ROAD Winter Park, FL MLS# O6442410
  • Recently Listed with Virtual Tour
1 of 67
$3,390,000
5

Beds

5.2

Baths

4,520

Sq.Ft.

1751 GLENCOE ROAD

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1761 LEGION DRIVE Winter Park, FL MLS# O6435967
  • Virtual Tour
1 of 66
$3,265,000
5

Beds

5.1

Baths

4,949

Sq.Ft.

1761 LEGION DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2823 PARKLAND CIRCLE Winter Park, FL MLS# O6444919
  • New Construction with Virtual Tour
1 of 46
$3,250,000
5

Beds

6.0

Baths

4,459

Sq.Ft.

2823 PARKLAND CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 4572 N PALMETTO AVENUE A Winter Park, FL MLS# O6442801
$3,200,000
8,843

Sq.Ft.

4572 N PALMETTO AVENUE A

Winter Park, FL

Courtesy of VINAS DEL MAR REALTY, INC.
View 2119 HOWARD DRIVE Winter Park, FL MLS# O6442111
  • New Construction
1 of 11
$3,195,000
5

Beds

5.1

Baths

4,139

Sq.Ft.

2119 HOWARD DRIVE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1821 ENGLEWOOD ROAD Winter Park, FL MLS# O6345085
  • New Construction with Virtual Tour
1 of 39
$3,075,000
5

Beds

5.1

Baths

3,863

Sq.Ft.

1821 ENGLEWOOD ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 125 S INTERLACHEN AVENUE 2 Winter Park, FL MLS# O6411134
$2,995,000
3

Beds

3.2

Baths

3,244

Sq.Ft.

125 S INTERLACHEN AVENUE 2

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1836 WHITEHALL DRIVE Winter Park, FL MLS# O6416158
  • New Construction with Virtual Tour
1 of 70
$2,995,000
5

Beds

6.1

Baths

4,168

Sq.Ft.

1836 WHITEHALL DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1591 Cardinal Court Winter Park, FL MLS# 1078693
  • New Construction
1 of 44
$2,995,000
5

Beds

3.0

Baths

3,523

Sq.Ft.

1591 Cardinal Court

Winter Park, FL

Brevard
View 532 LANGHOLM DRIVE Winter Park, FL MLS# O6442823
  • New Construction with Virtual Tour
1 of 18
$2,990,000
5

Beds

4.1

Baths

4,050

Sq.Ft.

532 LANGHOLM DRIVE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 609 S PHELPS AVENUE Winter Park, FL MLS# O6388598
  • New Construction with Virtual Tour
1 of 18
$2,800,000
5

Beds

4.1

Baths

4,018

Sq.Ft.

609 S PHELPS AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1773 WALNUT AVENUE Winter Park, FL MLS# O6437159
  • New Construction with Virtual Tour
1 of 25
$2,725,000
5

Beds

4.1

Baths

3,784

Sq.Ft.

1773 WALNUT AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL 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

361

Estimated median home price

$769,000
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 3
$100K - 200K 34
$200K - 300K 22
$300K - 400K 21
$400K - 500K 30
$500K - 600K 28
$600K - 700K 34
$700K - 800K 17
$800K - 900K 14
$900K - 1M 14
$1M - Max 144

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 214
Townhouse 20
Condo 78
Commercial 15
Rental 85
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/20/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include 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 10/20/2026.

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 10/20/2026.