253 total properties
Did you mean the neighborhood Winter Park?
View 640 ARJAY WAY Winter Park, FL MLS# O6372947
  • Virtual Tour
1 of 46
$2,000,000
5

Beds

3.2

Baths

3,860

Sq.Ft.

640 ARJAY WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2036 VIA TUSCANY Winter Park, FL MLS# O6379888
  • Recently Listed
1 of 19
$2,000,000
3

Beds

2.0

Baths

2,148

Sq.Ft.

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2036 VIA TUSCANY Winter Park, FL MLS# O6380892
  • Recently Listed
1 of 6
$2,000,000
Studio

Beds

0.0

Baths

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1540 PALM AVENUE Winter Park, FL MLS# O6345573
  • Virtual Tour
1 of 58
$1,999,000
5

Beds

3.1

Baths

3,423

Sq.Ft.

1540 PALM AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2614 PARKLAND DRIVE Winter Park, FL MLS# O6301489
  • Virtual Tour
1 of 54
$1,992,000
4

Beds

3.1

Baths

3,307

Sq.Ft.

2614 PARKLAND DRIVE

Winter Park, FL

Courtesy of JW GASTON LLC
View 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6381988
  • Recently Listed
1 of 3
$1,950,000
4

Beds

4.0

Baths

2,810

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1841 HARLAND PARK DRIVE Winter Park, FL MLS# O6369653
$1,895,000
4

Beds

3.1

Baths

3,470

Sq.Ft.

1841 HARLAND PARK DRIVE

Winter Park, FL

Courtesy of SELECTIVE REALTY GROUP LLC
View 1451 LYNDALE BOULEVARD Winter Park, FL MLS# O6237975
$1,799,999
6

Beds

4.0

Baths

3,853

Sq.Ft.

1451 LYNDALE BOULEVARD

Winter Park, FL

Courtesy of REALTY ONE GROUP MVP
View 633 BALMORAL ROAD Winter Park, FL MLS# O6353491
  • Virtual Tour
1 of 8
$1,795,000
4

Beds

2.1

Baths

2,674

Sq.Ft.

633 BALMORAL ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 633 BALMORAL ROAD Winter Park, FL MLS# O6353528
  • Virtual Tour
1 of 9
$1,795,000
Studio

Beds

0.0

Baths

633 BALMORAL ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1861 TAYLOR AVENUE Winter Park, FL MLS# O6375732
  • Virtual Tour
1 of 50
$1,775,000
5

Beds

5.2

Baths

3,116

Sq.Ft.

1861 TAYLOR AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 617 WORTHINGTON DRIVE Winter Park, FL MLS# O6320955
$1,770,000
5

Beds

4.1

Baths

3,533

Sq.Ft.

617 WORTHINGTON DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1840 ANZLE AVENUE Winter Park, FL MLS# O6374102
  • New Construction with Virtual Tour
1 of 12
$1,750,000
4

Beds

2.1

Baths

2,350

Sq.Ft.

1840 ANZLE AVENUE

Winter Park, FL

Courtesy of B LIVE COMMERCIAL AND RESIDENT
View 1016 HOWELL BRANCH ROAD Winter Park, FL MLS# O6386288
  • Recently Listed
1 of 64
$1,749,000
4

Beds

3.0

Baths

3,142

Sq.Ft.

1016 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of PLAID PROPERTIES, LLC
View 1630 CHESTNUT AVENUE Winter Park, FL MLS# O6360357
  • Virtual Tour
1 of 58
$1,725,000
3

Beds

4.1

Baths

3,164

Sq.Ft.

1630 CHESTNUT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 234 DETMAR DRIVE Winter Park, FL MLS# O6379927
  • Recently Listed with Virtual Tour
1 of 45
$1,695,000
5

Beds

5.1

Baths

3,609

Sq.Ft.

234 DETMAR DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1810 HOLLYWOOD AVENUE Winter Park, FL MLS# O6377320
  • New Construction with Virtual Tour
1 of 10
$1,689,000
4

Beds

3.1

Baths

2,604

Sq.Ft.

1810 HOLLYWOOD AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 446 ALBERTA DRIVE Winter Park, FL MLS# O6319233
  • Virtual Tour
1 of 69
$1,675,000
4

Beds

2.1

Baths

3,263

Sq.Ft.

446 ALBERTA DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 501 DARCEY DRIVE Winter Park, FL MLS# O6378578
  • Virtual Tour
1 of 39
$1,675,000
5

Beds

4.1

Baths

3,033

Sq.Ft.

501 DARCEY DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1340 PLACE PICARDY Winter Park, FL MLS# O6382113
  • Recently Listed with Virtual Tour
1 of 34
$1,650,000
3

Beds

3.1

Baths

3,459

Sq.Ft.

1340 PLACE PICARDY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES

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

308

Estimated median home price

$697,250
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 6
$100K - 200K 38
$200K - 300K 30
$300K - 400K 21
$400K - 500K 25
$500K - 600K 16
$600K - 700K 20
$700K - 800K 21
$800K - 900K 6
$900K - 1M 7
$1M - Max 118

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 174
Townhouse 15
Condo 84
Commercial 4
Rental 80
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 2/28/2026)

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 2/28/2026.

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 2/28/2026.

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 2/28/2026.