41 total properties
Did you mean the neighborhood Winter Park?
View 230 KILLARNEY DRIVE Winter Park, FL MLS# O6415950
  • Recently Listed with Virtual Tour
1 of 15
$1,250,000
4

Beds

1.0

Baths

1,260

Sq.Ft.

230 KILLARNEY DRIVE

Winter Park, FL

View 240 KILLARNEY DRIVE Winter Park, FL MLS# O6415977
  • Recently Listed with Virtual Tour
1 of 15
$1,275,000
3

Beds

2.1

Baths

1,329

Sq.Ft.

240 KILLARNEY DRIVE

Winter Park, FL

View 462 W LYMAN AVENUE Winter Park, FL MLS# O6423842
  • Recently Listed with Virtual Tour
1 of 25
$1,595,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

462 W LYMAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1778 MONDRIAN CIRCLE Winter Park, FL MLS# O6422941
  • Virtual Tour
1 of 52
$1,339,000
3

Beds

3.1

Baths

2,377

Sq.Ft.

1778 MONDRIAN CIRCLE

Winter Park, FL

View 250 KILLARNEY Winter Park, FL MLS# O6419382
  • Recently Listed with 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 777 HALIFAX AVENUE Winter Park, FL MLS# O6422901
  • Virtual Tour
1 of 48
$1,500,000
5

Beds

4.1

Baths

3,109

Sq.Ft.

777 HALIFAX AVENUE

Winter Park, FL

View 512 W SWOOPE AVENUE Winter Park, FL MLS# O6417375
  • 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

View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6418198
$1,275,000
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

Winter Park, FL

View 1421 CHAPMAN CIRCLE Winter Park, FL MLS# O6415941
  • Virtual Tour
1 of 49
$1,450,000
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

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 1600 ALABAMA DRIVE 402 Winter Park, FL MLS# O6413153
$1,250,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

1600 ALABAMA DRIVE 402

Winter Park, FL

View 1841 LAKE SPIER DRIVE Winter Park, FL MLS# O6407841
$1,595,000
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 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6401352
  • New Construction with Virtual Tour
1 of 49
$1,599,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6406381
  • New Construction with Virtual Tour
1 of 25
$1,249,900
4

Beds

3.1

Baths

2,936

Sq.Ft.

Address not provided

Winter Park, FL

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
$1,465,000
4

Beds

4.0

Baths

2,756

Sq.Ft.

1581 MAGNOLIA AVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. 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

323

Estimated median home price

$839,000
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 7
$100K - 200K 39
$200K - 300K 18
$300K - 400K 15
$400K - 500K 21
$500K - 600K 22
$600K - 700K 25
$700K - 800K 11
$800K - 900K 14
$900K - 1M 8
$1M - Max 143

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 199
Townhouse 17
Condo 73
Commercial 6
Rental 67
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/20/2026)

Information deemed reliable but not guaranteed.

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 7/21/2026.