364 total properties
Did you mean the neighborhood Winter Park?
View 1702 ARBOR PARK DRIVE Winter Park, FL MLS# O6435407
  • New Construction with Virtual Tour
1 of 49
$1,900,000
4

Beds

3.1

Baths

2,950

Sq.Ft.

1702 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 2614 PARKLAND DRIVE Winter Park, FL MLS# O6444165
  • Virtual Tour
1 of 54
$1,890,000
4

Beds

3.1

Baths

3,307

Sq.Ft.

2614 PARKLAND DRIVE

Winter Park, FL

Courtesy of JW GASTON LLC
View 922 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6424685
$1,875,000
4

Beds

4.0

Baths

3,440

Sq.Ft.

922 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 751 PANSY AVENUE Winter Park, FL MLS# O6432554
  • Virtual Tour
1 of 44
$1,875,000
3

Beds

3.1

Baths

2,703

Sq.Ft.

751 PANSY AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1550 PALM AVENUE Winter Park, FL MLS# O6436458
  • New Construction
1 of 10
$1,829,000
4

Beds

3.1

Baths

2,706

Sq.Ft.

1550 PALM AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 281 BREWER AVENUE Winter Park, FL MLS# O6424364
  • Virtual Tour
1 of 49
OPEN HOUSE: Saturday 10/24 12:00 PM - 2:00 PM
$1,800,000
5

Beds

4.1

Baths

4,029

Sq.Ft.

281 BREWER AVENUE

Winter Park, FL

Courtesy of HENTHORN REAL ESTATE
View 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6416565
  • New Construction with Virtual Tour
1 of 22
$1,795,000
4

Beds

4.0

Baths

2,819

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 101 S NEW YORK AVENUE 311 Winter Park, FL MLS# O6416927
$1,775,000
3

Beds

3.1

Baths

3,112

Sq.Ft.

101 S NEW YORK AVENUE 311

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 1225 SHARON PLACE Winter Park, FL MLS# O6443546
  • Virtual Tour
1 of 78
$1,749,000
5

Beds

3.1

Baths

3,097

Sq.Ft.

1225 SHARON PLACE

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 1840 BRYAN AVENUE Winter Park, FL MLS# O6431360
  • Virtual Tour
1 of 53
$1,725,000
4

Beds

3.1

Baths

3,727

Sq.Ft.

1840 BRYAN AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 2613 LAFAYETTE AVENUE Winter Park, FL MLS# O6447662
  • Recently Listed with Virtual Tour
1 of 12
$1,699,900
4

Beds

3.1

Baths

2,661

Sq.Ft.

2613 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2308 MULBRY DRIVE Winter Park, FL MLS# O6432803
  • New Construction with Virtual Tour
1 of 12
$1,699,000
4

Beds

3.1

Baths

2,530

Sq.Ft.

2308 MULBRY DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2343 VERSAILLES AVENUE Winter Park, FL MLS# O6432029
$1,699,000
4

Beds

3.1

Baths

3,307

Sq.Ft.

2343 VERSAILLES AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1420 MAGNOLIA AVENUE Winter Park, FL MLS# O6404564
  • Virtual Tour
1 of 67
$1,690,000
4

Beds

3.1

Baths

3,174

Sq.Ft.

1420 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2407 LAFAYETTE AVENUE Winter Park, FL MLS# O6431314
$1,625,000
5

Beds

4.1

Baths

3,133

Sq.Ft.

2407 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 723 SYMONDS AVENUE Winter Park, FL MLS# O6406823
  • Virtual Tour
1 of 50
$1,600,000
4

Beds

4.0

Baths

3,065

Sq.Ft.

723 SYMONDS AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 250 KILLARNEY Winter Park, FL MLS# O6419382
  • Virtual Tour
1 of 10
$1,600,000
4

Beds

3.1

Baths

2,568

Sq.Ft.

250 KILLARNEY

Winter Park, FL

Courtesy of FLORIDA PROPERTY SPECIALIST
View 2207 KINDEL AVENUE Winter Park, FL MLS# O6436815
  • Virtual Tour
1 of 47
OPEN HOUSE: Saturday 10/24 10:00 AM - 12:00 PM
$1,600,000
3

Beds

2.1

Baths

2,733

Sq.Ft.

2207 KINDEL AVENUE

Winter Park, FL

Courtesy of THE SIMON SIMAAN GROUP
View 1864 GRINNELL TERRACE Winter Park, FL MLS# O6403822
$1,599,000
5

Beds

3.1

Baths

3,028

Sq.Ft.

1864 GRINNELL TERRACE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY

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

364

Estimated median home price

$759,500
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 33
$200K - 300K 23
$300K - 400K 21
$400K - 500K 31
$500K - 600K 28
$600K - 700K 35
$700K - 800K 18
$800K - 900K 14
$900K - 1M 14
$1M - Max 144

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 216
Townhouse 22
Condo 77
Commercial 15
Rental 83
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/21/2026)

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 10/21/2026.

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 10/21/2026.