109 total properties
Did you mean the neighborhood Winter Park?
View 1386 CLAY STREET Winter Park, FL MLS# O6354139
  • Virtual Tour
1 of 20
$479,000
2

Beds

1.0

Baths

1,182

Sq.Ft.

1386 CLAY STREET

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 875 W LYMAN AVENUE Winter Park, FL MLS# O6363961
$475,000
2

Beds

2.0

Baths

760

Sq.Ft.

875 W LYMAN AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 3054 BLUEBROOK DRIVE Winter Park, FL MLS# O6309509
$469,900
3

Beds

2.0

Baths

1,939

Sq.Ft.

3054 BLUEBROOK DRIVE

Winter Park, FL

Courtesy of ALORA REALTY GROUP INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6302210
$459,000
2

Beds

1.0

Baths

954

Sq.Ft.

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 1564 CAVENDISH ROAD Winter Park, FL MLS# O6292750
$450,000
3

Beds

1.0

Baths

1,140

Sq.Ft.

1564 CAVENDISH ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 443 S LAKEMONT AVENUE Winter Park, FL MLS# O6356128
$450,000
3

Beds

2.0

Baths

1,364

Sq.Ft.

443 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of MILLER GRANT AND COMPANY
View 640 N PARK AVENUE 5 Winter Park, FL MLS# O6367841
  • Recently Listed with Virtual Tour
1 of 28
$450,000
1

Beds

1.0

Baths

673

Sq.Ft.

640 N PARK AVENUE 5

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 639 FRIAR ROAD Winter Park, FL MLS# O6360212
  • Virtual Tour
1 of 21
$449,900
4

Beds

3.0

Baths

1,829

Sq.Ft.

639 FRIAR ROAD

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 714 DENTON ROAD Winter Park, FL MLS# O6362464
  • Virtual Tour
1 of 32
$449,900
3

Beds

3.0

Baths

1,786

Sq.Ft.

714 DENTON ROAD

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 1347 ORCHID AVENUE Winter Park, FL MLS# S5140042
$449,900
4

Beds

2.0

Baths

1,490

Sq.Ft.

1347 ORCHID AVENUE

Winter Park, FL

Courtesy of SHELDON PROFESSIONALS INC
View 824 GARRETT COURT Winter Park, FL MLS# O6368324
  • Recently Listed with Virtual Tour
1 of 35
$449,000
4

Beds

2.0

Baths

1,738

Sq.Ft.

824 GARRETT COURT

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1909 EDWIN BOULEVARD Winter Park, FL MLS# O6362682
$440,000
3

Beds

2.0

Baths

1,355

Sq.Ft.

1909 EDWIN BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2835 BONGART ROAD Winter Park, FL MLS# O6367949
$439,900
3

Beds

3.0

Baths

1,880

Sq.Ft.

2835 BONGART ROAD

Winter Park, FL

Courtesy of FUTURE HOME REALTY INC
View 2743 MERRIE OAKS ROAD Winter Park, FL MLS# O6361079
$439,000
3

Beds

2.0

Baths

1,661

Sq.Ft.

2743 MERRIE OAKS ROAD

Winter Park, FL

Courtesy of ONE45 REALTY LLC
View 3236 KNOTTYPINE AVENUE Winter Park, FL MLS# O6364200
$429,000
3

Beds

2.0

Baths

1,578

Sq.Ft.

3236 KNOTTYPINE AVENUE

Winter Park, FL

Courtesy of URBAN-O REAL ESTATE SOLUTIONS
View 786 W CANTON AVENUE Winter Park, FL MLS# O6161876
$425,000
Studio

Beds

0.0

Baths

786 W CANTON AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1007 EARLY AVENUE Winter Park, FL MLS# TB8437929
$425,000
3

Beds

2.0

Baths

1,721

Sq.Ft.

1007 EARLY AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2580 EUSTON ROAD Winter Park, FL MLS# O6355208
$425,000
3

Beds

2.0

Baths

1,158

Sq.Ft.

2580 EUSTON ROAD

Winter Park, FL

Courtesy of LOKATION
View 900 CARVER STREET Winter Park, FL MLS# O6368746
  • Recently Listed
1 of 3
$425,000
3

Beds

2.0

Baths

1,794

Sq.Ft.

900 CARVER STREET

Winter Park, FL

Courtesy of LEGACY REALTY & BROKERS LLC
View 740 BAFFIE AVENUE Winter Park, FL MLS# O6345637
$420,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

740 BAFFIE AVENUE

Winter Park, FL

Courtesy of CREEGAN GROUP

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

301

Estimated median home price

$639,000
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

PriceCount
$0 - 100K6
$100K - 200K40
$200K - 300K21
$300K - 400K19
$400K - 500K32
$500K - 600K26
$600K - 700K21
$700K - 800K22
$800K - 900K5
$900K - 1M11
$1M - Max98

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family176
Townhouse19
Condo77
Commercial5
Rental108
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 12/29/2025)

Information deemed reliable but not guaranteed.

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 12/29/2025.