279 total properties
Did you mean the neighborhood Winter Park?
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 345 BELOIT AVENUE Winter Park, FL MLS# O6448919
  • Virtual Tour
1 of 34
$1,625,000
3

Beds

2.1

Baths

2,884

Sq.Ft.

345 BELOIT AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 533 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6440841
  • Virtual Tour
1 of 31
OPEN HOUSE: Friday 10/30 3:00 PM - 6:00 PM
$1,599,000
4

Beds

3.1

Baths

2,942

Sq.Ft.

533 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1113 VIA DEL MAR Winter Park, FL MLS# O6379697
  • Virtual Tour
1 of 9
$1,595,000
3

Beds

2.0

Baths

2,012

Sq.Ft.

1113 VIA DEL MAR

Winter Park, FL

Courtesy of BAY HILL REALTY LLC
View 1113 VIA DEL MAR Winter Park, FL MLS# O6416144
  • Virtual Tour
1 of 9
$1,595,000
0.0

Baths

1113 VIA DEL MAR

Winter Park, FL

Courtesy of BAY HILL REALTY LLC
View 2207 KINDEL AVENUE Winter Park, FL MLS# O6436815
  • Virtual Tour
1 of 47
$1,575,000
3

Beds

2.1

Baths

2,733

Sq.Ft.

2207 KINDEL AVENUE

Winter Park, FL

Courtesy of THE SIMON SIMAAN GROUP
View 905 ENCLAVE PLACE Winter Park, FL MLS# O6383679
  • New Construction with Virtual Tour
1 of 10
$1,550,000
4

Beds

3.1

Baths

2,756

Sq.Ft.

905 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 901 ENCLAVE PLACE Winter Park, FL MLS# O6383602
  • New Construction with Virtual Tour
1 of 11
$1,550,000
4

Beds

3.1

Baths

2,738

Sq.Ft.

901 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6436367
  • New Construction with Virtual Tour
1 of 64
OPEN HOUSE: Sunday 11/1 2:00 PM - 4:00 PM
$1,550,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 271 S ORLANDO AVENUE Winter Park, FL MLS# O6450599
  • Recently Listed with Virtual Tour
1 of 14
$1,550,000
3,430

Sq.Ft.

271 S ORLANDO AVENUE

Winter Park, FL

Courtesy of SAND DOLLAR REALTY GROUP INC
View 341 E READING WAY Winter Park, FL MLS# O6420387
$1,525,000
4

Beds

4.0

Baths

3,723

Sq.Ft.

341 E READING WAY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 641 NORTHWOOD CIRCLE Winter Park, FL MLS# O6412554
  • Virtual Tour
1 of 37
OPEN HOUSE: Sunday 11/1 11:00 AM - 2:00 PM
$1,499,000
3

Beds

3.2

Baths

2,756

Sq.Ft.

641 NORTHWOOD CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1841 LAKE SPIER DRIVE Winter Park, FL MLS# O6407841
$1,498,000
3

Beds

4.0

Baths

2,467

Sq.Ft.

1841 LAKE SPIER DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 446 MELROSE AVENUE Winter Park, FL MLS# O6402113
$1,495,000
4

Beds

2.0

Baths

2,640

Sq.Ft.

446 MELROSE AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1570 PALMER AVENUE Winter Park, FL MLS# O6383529
  • Virtual Tour
1 of 36
$1,485,000
4

Beds

3.1

Baths

3,048

Sq.Ft.

1570 PALMER AVENUE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 462 W LYMAN AVENUE Winter Park, FL MLS# O6423842
  • Virtual Tour
1 of 28
$1,450,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

462 W LYMAN AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 100 S VIRGINIA AVENUE 201 Winter Park, FL MLS# O6442678
$1,450,000
3

Beds

3.0

Baths

2,756

Sq.Ft.

100 S VIRGINIA AVENUE 201

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY 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

351

Estimated median home price

$775,000
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 20
$300K - 400K 16
$400K - 500K 32
$500K - 600K 24
$600K - 700K 36
$700K - 800K 16
$800K - 900K 13
$900K - 1M 14
$1M - Max 143

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 207
Townhouse 22
Condo 76
Commercial 15
Rental 87
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/28/2026)

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 10/29/2026.

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 10/29/2026.