161 total properties
Did you mean the neighborhood Winter Park?
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • New Construction with Virtual Tour
1 of 9
$944,890
4

Beds

3.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
  • Virtual Tour
1 of 7
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 29
$925,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6390670
  • Virtual Tour
1 of 19
$899,900
3

Beds

2.0

Baths

1,536

Sq.Ft.

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6398302
  • Virtual Tour
1 of 18
$899,900
Studio

Beds

0.0

Baths

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View 338 BLUE HERON DRIVE Winter Park, FL MLS# O6410174
  • Virtual Tour
1 of 44
$865,000
3

Beds

3.0

Baths

2,017

Sq.Ft.

338 BLUE HERON DRIVE

Winter Park, FL

View 1780 BRYAN AVENUE Winter Park, FL MLS# O6365369
  • Virtual Tour
1 of 8
$849,000
4

Beds

2.0

Baths

1,617

Sq.Ft.

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1780 BRYAN AVENUE Winter Park, FL MLS# O6402643
  • Virtual Tour
1 of 8
$849,000
Studio

Beds

0.0

Baths

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 439 N CAPEN AVENUE Winter Park, FL MLS# O6422949
  • Recently Listed with Virtual Tour
1 of 29
$849,000
3

Beds

2.1

Baths

1,861

Sq.Ft.

439 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1927 ELAND AVENUE Winter Park, FL MLS# O6381009
  • Virtual Tour
1 of 68
$820,000
5

Beds

3.0

Baths

2,242

Sq.Ft.

1927 ELAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6404545
  • Virtual Tour
1 of 42
$800,000
5

Beds

3.0

Baths

2,194

Sq.Ft.

739 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of SERHANT
View 1900 WINTER PARK ROAD Winter Park, FL MLS# O6402566
$799,000
4

Beds

2.0

Baths

1,511

Sq.Ft.

1900 WINTER PARK ROAD

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 730 W SWOOPE AVENUE Winter Park, FL MLS# S5152493
  • Recently Listed with Virtual Tour
1 of 35
$770,000
5

Beds

3.0

Baths

2,132

Sq.Ft.

730 W SWOOPE AVENUE

Winter Park, FL

View 300 CAROLINA AVENUE 402C Winter Park, FL MLS# O6410016
$750,000
3

Beds

2.0

Baths

1,350

Sq.Ft.

300 CAROLINA AVENUE 402C

Winter Park, FL

View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
  • Virtual Tour
1 of 34
$745,000
2

Beds

3.0

Baths

1,440

Sq.Ft.

408 HOLT AVENUE

Winter Park, FL

Courtesy of THE REAL ESTATE PRINCIPLE, INC
View 3377 FORSYTH ROAD Winter Park, FL MLS# O6173998
  • Virtual Tour
1 of 15
$725,000
4,104

Sq.Ft.

3377 FORSYTH ROAD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 770 W WEBSTER AVENUE Winter Park, FL MLS# O6323574
  • Virtual Tour
1 of 34
$725,000
4

Beds

2.0

Baths

1,008

Sq.Ft.

770 W WEBSTER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 770 W WEBSTER AVENUE REAR LOT Winter Park, FL MLS# O6323647
$725,000
Studio

Beds

0.0

Baths

770 W WEBSTER AVENUE REAR LOT

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2344 WOODCREST DRIVE Winter Park, FL MLS# O6418782
  • Recently Listed with Virtual Tour
1 of 22
$719,900
4

Beds

2.0

Baths

1,764

Sq.Ft.

2344 WOODCREST DRIVE

Winter Park, FL

View 1701 GOODRICH AVENUE Winter Park, FL MLS# O6400278
$709,000
3

Beds

2.0

Baths

1,528

Sq.Ft.

1701 GOODRICH AVENUE

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

306

Estimated median home price

$735,000
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 41
$200K - 300K 18
$300K - 400K 14
$400K - 500K 25
$500K - 600K 21
$600K - 700K 24
$700K - 800K 11
$800K - 900K 11
$900K - 1M 5
$1M - Max 132

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 186
Townhouse 14
Condo 73
Commercial 7
Rental 72
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/10/2026)

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 Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes 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 7/10/2026.

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 7/10/2026.