364 total properties
Did you mean the neighborhood Winter Park?
View 1695 LEE ROAD B108 Winter Park, FL MLS# O6422568
  • Recently Listed with Virtual Tour
1 of 15
$89,999
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B108

Winter Park, FL

View 2611 LOTAFUN AVENUE Winter Park, FL MLS# O6422197
  • Virtual Tour
1 of 34
$449,000
3

Beds

2.0

Baths

1,838

Sq.Ft.

2611 LOTAFUN AVENUE

Winter Park, FL

View 7500 WAUNATTA COURT Winter Park, FL MLS# TB8525179
  • Virtual Tour
1 of 34
$299,900
3

Beds

2.0

Baths

1,998

Sq.Ft.

7500 WAUNATTA COURT

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
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 7509 GLENMOOR LANE Winter Park, FL MLS# O6421887
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1 of 45
$499,500
3

Beds

2.0

Baths

2,067

Sq.Ft.

7509 GLENMOOR LANE

Winter Park, FL

View 252 SCOTTSDALE SQ 252 Winter Park, FL MLS# O6421977
$85,000
2

Beds

1.1

Baths

1,085

Sq.Ft.

252 SCOTTSDALE SQ 252

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 729 MONMOUTH WAY Winter Park, FL MLS# O6422168
$799,000
4

Beds

3.0

Baths

2,332

Sq.Ft.

729 MONMOUTH WAY

Winter Park, FL

View 1622 ARBOR PARK DRIVE Winter Park, FL MLS# O6420937
$695,000
Studio

Beds

0.0

Baths

1622 ARBOR PARK DRIVE

Winter Park, FL

View 1622 ARBOR PARK DRIVE Winter Park, FL MLS# O6420928
$695,000
3

Beds

1.1

Baths

1,351

Sq.Ft.

1622 ARBOR PARK DRIVE

Winter Park, FL

View 341 E READING WAY Winter Park, FL MLS# O6420387
1 of 57
OPEN HOUSE: Sunday 7/26 2:00 PM - 4:00 PM
$1,695,000
4

Beds

4.0

Baths

3,723

Sq.Ft.

341 E READING WAY

Winter Park, FL

View 1960 BISCAYNE DRIVE Winter Park, FL MLS# O6421199
$300,000
2

Beds

1.0

Baths

1,272

Sq.Ft.

1960 BISCAYNE DRIVE

Winter Park, FL

View 722 S RANGER BOULEVARD Winter Park, FL MLS# O6421873
$825,000
4

Beds

3.0

Baths

2,164

Sq.Ft.

722 S RANGER BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1000 S SEMORAN BOULEVARD 306 Winter Park, FL MLS# R4911525
$138,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 306

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 404 Winter Park, FL MLS# R4911526
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 404

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 408 Winter Park, FL MLS# R4911527
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 408

Winter Park, FL

View 4887 N MAGNOLIA AVENUE Winter Park, FL MLS# O6420961
$495,000
4

Beds

3.0

Baths

1,955

Sq.Ft.

4887 N MAGNOLIA AVENUE

Winter Park, FL

Courtesy of LUXE PROPERTIES
View 1695 LEE ROAD A116 Winter Park, FL MLS# O6420863
  • Virtual Tour
1 of 18
$135,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A116

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1122 WASHINGTON AVENUE 7B Winter Park, FL MLS# O6421299
$575,000
2

Beds

2.1

Baths

1,556

Sq.Ft.

1122 WASHINGTON AVENUE 7B

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 1180 VIA LUGANO Winter Park, FL MLS# O6413198
  • Recently Listed with Virtual Tour
1 of 67
$4,900,000
5

Beds

5.1

Baths

4,961

Sq.Ft.

1180 VIA LUGANO

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3060 George Mason D Winter Park, FL MLS# A12044474
  • Virtual Tour
1 of 19
$107,000
2

Beds

2.0

Baths

1,062

Sq.Ft.

3060 George Mason D

Winter Park, FL

Courtesy of CAPITAL INTL REALTY 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

377

Estimated median home price

$779,000
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 43
$200K - 300K 25
$300K - 400K 18
$400K - 500K 29
$500K - 600K 24
$600K - 700K 32
$700K - 800K 14
$800K - 900K 15
$900K - 1M 9
$1M - Max 161

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 228
Townhouse 20
Condo 85
Commercial 11
Rental 69
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 7/24/2026)

Information deemed reliable but not guaranteed.

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.

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 7/25/2026.

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 7/25/2026.