46 total properties
Did you mean the neighborhood Winter Park?
View 341 E READING WAY Winter Park, FL MLS# O6420387
  • Recently Listed
1 of 57
OPEN HOUSE: Sunday 7/5 2:00 PM - 4:00 PM
$1,695,000
4

Beds

4.0

Baths

3,723

Sq.Ft.

341 E READING WAY

Winter Park, FL

View 512 W SWOOPE AVENUE Winter Park, FL MLS# O6417375
  • Recently Listed with Virtual Tour
1 of 46
$1,399,000
3

Beds

2.1

Baths

2,585

Sq.Ft.

512 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 321 SYLVAN BOULEVARD Winter Park, FL MLS# O6417674
$1,395,000
3

Beds

2.1

Baths

2,821

Sq.Ft.

321 SYLVAN BOULEVARD

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1421 CHAPMAN CIRCLE Winter Park, FL MLS# O6415941
  • Virtual Tour
1 of 49
$1,550,000
4

Beds

3.1

Baths

3,578

Sq.Ft.

1421 CHAPMAN CIRCLE

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 1220 WOODMERE DRIVE Winter Park, FL MLS# O6415611
  • Virtual Tour
1 of 44
$1,700,000
4

Beds

3.1

Baths

2,815

Sq.Ft.

1220 WOODMERE DRIVE

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 641 NORTHWOOD CIRCLE Winter Park, FL MLS# O6412554
  • Virtual Tour
1 of 41
$1,795,000
3

Beds

3.2

Baths

2,756

Sq.Ft.

641 NORTHWOOD CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 723 SYMONDS AVENUE Winter Park, FL MLS# O6406823
  • Virtual Tour
1 of 50
$1,800,000
4

Beds

4.0

Baths

3,065

Sq.Ft.

723 SYMONDS AVENUE

Winter Park, FL

View 1077 MINNESOTA AVENUE Winter Park, FL MLS# O6411722
$1,395,000
4

Beds

4.0

Baths

3,046

Sq.Ft.

1077 MINNESOTA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1841 LAKE SPIER DRIVE Winter Park, FL MLS# O6407841
$1,650,000
3

Beds

4.0

Baths

2,467

Sq.Ft.

1841 LAKE SPIER DRIVE

Winter Park, FL

View 120 BROADVIEW AVENUE Winter Park, FL MLS# O6410178
$1,450,000
Studio

Beds

0.0

Baths

120 BROADVIEW AVENUE

Winter Park, FL

View 120 BROADVIEW AVENUE Winter Park, FL MLS# O6409860
$1,450,000
3

Beds

2.0

Baths

1,747

Sq.Ft.

120 BROADVIEW AVENUE

Winter Park, FL

View 1347 CHAPMAN CIRCLE Winter Park, FL MLS# O6408189
$1,395,000
4

Beds

3.1

Baths

2,922

Sq.Ft.

1347 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of ORLANDO PROPERTY ADVISORS
View 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6401352
  • New Construction with Virtual Tour
1 of 49
$1,665,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

View 266 W LYMAN AVENUE Winter Park, FL MLS# O6406526
$1,375,000
3

Beds

3.0

Baths

2,000

Sq.Ft.

266 W LYMAN AVENUE

Winter Park, FL

Courtesy of MAROON REALTY GROUP LLC
View 1420 MAGNOLIA AVENUE Winter Park, FL MLS# O6404564
  • Virtual Tour
1 of 67
$1,750,000
4

Beds

3.1

Baths

3,174

Sq.Ft.

1420 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
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
View 1581 MAGNOLIA AVE Winter Park, FL MLS# O6396118
  • Virtual Tour
1 of 75
$1,495,000
4

Beds

4.0

Baths

2,756

Sq.Ft.

1581 MAGNOLIA AVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1660 WALNUT AVENUE Winter Park, FL MLS# O6395277
  • New Construction with Virtual Tour
1 of 43
$1,569,000
4

Beds

3.1

Baths

2,249

Sq.Ft.

1660 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

394

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 46
$200K - 300K 26
$300K - 400K 19
$400K - 500K 30
$500K - 600K 29
$600K - 700K 34
$700K - 800K 17
$800K - 900K 13
$900K - 1M 9
$1M - Max 167

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 249
Townhouse 17
Condo 92
Commercial 7
Rental 69
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/3/2026)

Information deemed reliable but not guaranteed.

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 7/4/2026.