360 total properties
Did you mean the neighborhood Winter Park?
View 533 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6440841
  • Recently Listed with Virtual Tour
1 of 31
$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 1602 ALABAMA DRIVE 107 Winter Park, FL MLS# O6442900
  • Recently Listed with Virtual Tour
1 of 33
$1,150,000
2

Beds

2.0

Baths

993

Sq.Ft.

1602 ALABAMA DRIVE 107

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 4572 N PALMETTO AVENUE A Winter Park, FL MLS# O6442801
$3,200,000
8,843

Sq.Ft.

4572 N PALMETTO AVENUE A

Winter Park, FL

Courtesy of VINAS DEL MAR REALTY, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 624 FITZWALTER DRIVE Winter Park, FL MLS# O6443363
$549,000
3

Beds

2.0

Baths

1,335

Sq.Ft.

624 FITZWALTER DRIVE

Winter Park, FL

Courtesy of MARK SPAIN REAL ESTATE
View 602 TRINIDAD COURT 602 Winter Park, FL MLS# O6443577
$227,000
2

Beds

2.0

Baths

1,120

Sq.Ft.

602 TRINIDAD COURT 602

Winter Park, FL

Courtesy of CLARA HERRERA REALTY
View 1306 S PENNSYLVANIA AVENUE 5 Winter Park, FL MLS# O6443013
$359,000
2

Beds

1.0

Baths

830

Sq.Ft.

1306 S PENNSYLVANIA AVENUE 5

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1742 TEMPLE DRIVE Winter Park, FL MLS# O6443437
  • New Construction with Virtual Tour
1 of 41
$3,695,999
4

Beds

5.0

Baths

3,658

Sq.Ft.

1742 TEMPLE DRIVE

Winter Park, FL

Courtesy of ROI AVE LLC
View 1421 CHESTNUT AVENUE Winter Park, FL MLS# O6442587
$750,000
3

Beds

1.0

Baths

1,325

Sq.Ft.

1421 CHESTNUT AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 662 GRANVILLE DRIVE Winter Park, FL MLS# O6442030
  • Virtual Tour
1 of 78
$3,495,000
5

Beds

5.1

Baths

4,478

Sq.Ft.

662 GRANVILLE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 250 CAROLINA AVENUE 202 Winter Park, FL MLS# O6442686
$699,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

250 CAROLINA AVENUE 202

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1421 CHESTNUT AVENUE Winter Park, FL MLS# O6442995
$750,000
0.0

Baths

1421 CHESTNUT AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1517 HARMON AVENUE Winter Park, FL MLS# O6443217
$1,049,000
4

Beds

3.1

Baths

2,135

Sq.Ft.

1517 HARMON AVENUE

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 7302 SWALLOW RUN 7302 Winter Park, FL MLS# O6442345
$134,900
2

Beds

2.0

Baths

756

Sq.Ft.

7302 SWALLOW RUN 7302

Winter Park, FL

Courtesy of THE NAVY HOUSE
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6442348
  • Virtual Tour
1 of 41
$675,000
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2572 FIFESHIRE DRIVE Winter Park, FL MLS# O6442325
  • Virtual Tour
1 of 47
$899,900
4

Beds

2.1

Baths

2,578

Sq.Ft.

2572 FIFESHIRE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3334 YOUNG STREET Winter Park, FL MLS# O6442952
  • Virtual Tour
1 of 22
$474,900
3

Beds

2.0

Baths

1,706

Sq.Ft.

3334 YOUNG STREET

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 555 E LAKE SUE AVENUE Winter Park, FL MLS# O6442775
$2,095,000
4

Beds

4.0

Baths

3,776

Sq.Ft.

555 E LAKE SUE AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2119 HOWARD DRIVE Winter Park, FL MLS# O6442111
  • New Construction
1 of 11
$3,195,000
5

Beds

5.1

Baths

4,139

Sq.Ft.

2119 HOWARD DRIVE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1271 PALMER AVENUE Winter Park, FL MLS# O6441038
  • Virtual Tour
1 of 61
$2,195,000
4

Beds

4.1

Baths

2,850

Sq.Ft.

1271 PALMER AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 3209 HEARTWOOD AVENUE Winter Park, FL MLS# O6442556
$439,900
4

Beds

2.0

Baths

1,627

Sq.Ft.

3209 HEARTWOOD AVENUE

Winter Park, FL

Courtesy of LEDGE REAL ESTATE SOLUTIONS 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

369

Estimated median home price

$745,000
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 2
$100K - 200K 38
$200K - 300K 25
$300K - 400K 20
$400K - 500K 32
$500K - 600K 25
$600K - 700K 37
$700K - 800K 18
$800K - 900K 12
$900K - 1M 14
$1M - Max 146

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 215
Townhouse 21
Condo 82
Commercial 14
Rental 94
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 7
Mobile Home 0
Farms 0

(Data as of 10/13/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of Georgia MLS. Real estate listings held by brokerage firms other than Weichert's are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.

© 2026 Georgia MLS. All rights reserved

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 10/13/2026.

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 10/13/2026.