44 total properties
Did you mean the neighborhood Winter Park?
View 1707 HARMON AVENUE Winter Park, FL MLS# O6409180
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Saturday 5/23 10:00 AM - 12:00 PM
$695,000
3

Beds

2.0

Baths

1,669

Sq.Ft.

1707 HARMON AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2333 WESTMINSTER COURT Winter Park, FL MLS# O6407054
  • Recently Listed with Virtual Tour
1 of 48
$719,000
4

Beds

2.0

Baths

1,877

Sq.Ft.

2333 WESTMINSTER COURT

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1407 MILLER AVENUE Winter Park, FL MLS# O6406408
  • Recently Listed with Virtual Tour
1 of 44
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1407 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
The time to sell is now! THE TIME TO SELL IS NOW!
View 2940 DE BROCY WAY Winter Park, FL MLS# O6408085
  • Recently Listed with Virtual Tour
1 of 55
OPEN HOUSE: Saturday 5/23 11:00 AM - 1:00 PM
$785,000
3

Beds

2.0

Baths

2,679

Sq.Ft.

2940 DE BROCY WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6407540
  • Recently Listed
1 of 39
$719,000
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of ADAIR REALTY INC
View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
  • Recently Listed with 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 1960 WINTER PARK ROAD Winter Park, FL MLS# O6406091
$899,000
3

Beds

3.0

Baths

1,864

Sq.Ft.

1960 WINTER PARK ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6404545
  • Recently Listed with 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 627 DUNBLANE DRIVE Winter Park, FL MLS# O6405036
  • Recently Listed with Virtual Tour
1 of 36
$899,000
4

Beds

3.0

Baths

2,086

Sq.Ft.

627 DUNBLANE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1550 NORFOLK AVENUE Winter Park, FL MLS# O6402927
  • Virtual Tour
1 of 29
$725,000
3

Beds

2.0

Baths

1,762

Sq.Ft.

1550 NORFOLK AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 688 BRECHIN DRIVE Winter Park, FL MLS# O6403080
  • Virtual Tour
1 of 31
$724,900
4

Beds

2.0

Baths

1,599

Sq.Ft.

688 BRECHIN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1437 MILLER AVENUE Winter Park, FL MLS# O6403858
$750,000
5

Beds

4.0

Baths

2,150

Sq.Ft.

1437 MILLER AVENUE

Winter Park, FL

Courtesy of ORLANDO REAL ESTATE LLC
View 2324 LEE ROAD Winter Park, FL MLS# O6403791
  • Recently Listed with Virtual Tour
1 of 36
$750,000
2,124

Sq.Ft.

2324 LEE ROAD

Winter Park, FL

Courtesy of CARLISLE REALTY, LLC
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 1900 WINTER PARK ROAD Winter Park, FL MLS# O6402566
$849,900
4

Beds

2.0

Baths

1,511

Sq.Ft.

1900 WINTER PARK ROAD

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 1881 W FAIRBANKS AVENUE Winter Park, FL MLS# O6401500
$700,000
1,264

Sq.Ft.

1881 W FAIRBANKS AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1785 WALNUT AVENUE Winter Park, FL MLS# O6399577
  • Virtual Tour
1 of 35
$825,000
Studio

Beds

0.0

Baths

1785 WALNUT AVENUE

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 1960 WINTER PARK ROAD Winter Park, FL MLS# O6398264
$899,000
Studio

Beds

0.0

Baths

1960 WINTER PARK ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1701 GOODRICH AVENUE Winter Park, FL MLS# O6400278
  • Recently Listed
1 of 44
$739,000
3

Beds

2.0

Baths

1,528

Sq.Ft.

1701 GOODRICH AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
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

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

387

Estimated median home price

$785,000
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 50
$200K - 300K 22
$300K - 400K 22
$400K - 500K 29
$500K - 600K 23
$600K - 700K 28
$700K - 800K 20
$800K - 900K 16
$900K - 1M 8
$1M - Max 166

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 242
Townhouse 16
Condo 88
Commercial 7
Rental 72
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/20/2026)

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 5/21/2026.

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 5/21/2026.