17 total properties
Did you mean the neighborhood Winter Park?
View 2500 LEE ROAD 229 Winter Park, FL MLS# O6377616
  • Recently Listed with Virtual Tour
1 of 41
$255,000
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 229

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 1500 GAY ROAD 18A Winter Park, FL MLS# O6376215
  • Recently Listed with Virtual Tour
1 of 21
$259,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 18A

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View Address not provided Winter Park, FL MLS# O6375288
  • Recently Listed with Virtual Tour
1 of 35
$249,900
2

Beds

2.0

Baths

956

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of HOMEVEST REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 3220 NETHERWOOD DRIVE Winter Park, FL MLS# O6374172
  • Recently Listed with Virtual Tour
1 of 18
$285,000
2

Beds

2.0

Baths

1,036

Sq.Ft.

3220 NETHERWOOD DRIVE

Winter Park, FL

Courtesy of THE FIRM RE
View 1500 GAY ROAD 21-C Winter Park, FL MLS# O6373517
  • Recently Listed with Virtual Tour
1 of 27
$265,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 21-C

Winter Park, FL

Courtesy of REDFIN CORPORATION
View 6980 ALOMA AVENUE 32 Winter Park, FL MLS# O6373864
  • Recently Listed with Virtual Tour
1 of 12
$250,000
900

Sq.Ft.

6980 ALOMA AVENUE 32

Winter Park, FL

Courtesy of APPLE REALTY
View 1996 INDIANA AVENUE Winter Park, FL MLS# O6372229
$249,900
2

Beds

1.0

Baths

818

Sq.Ft.

1996 INDIANA AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
  • Virtual Tour
1 of 22
OPEN HOUSE: Saturday 1/31 1:00 PM - 2:30 PM
$298,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

Courtesy of CREEGAN GROUP
View 311 E MORSE BOULEVARD 6-3 Winter Park, FL MLS# O6362964
  • Adult Community with Virtual Tour
1 of 36
$319,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 6-3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 151 N ORLANDO AVENUE 226 Winter Park, FL MLS# O6361027
$255,000
2

Beds

1.0

Baths

768

Sq.Ft.

151 N ORLANDO AVENUE 226

Winter Park, FL

Courtesy of LOKATION
View 609 GALLERY DRIVE B204 Winter Park, FL MLS# O6357629
$275,000
2

Beds

2.0

Baths

893

Sq.Ft.

609 GALLERY DRIVE B204

Winter Park, FL

Courtesy of A2Z REALTY GROUP
View 2009 CORNELL AVENUE Winter Park, FL MLS# O6353956
$259,000
2

Beds

1.0

Baths

762

Sq.Ft.

2009 CORNELL AVENUE

Winter Park, FL

Courtesy of ORLANDO HOME DEALER LLC
View 1500 GAY ROAD 24B Winter Park, FL MLS# O6348568
$269,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 24B

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 151 N ORLANDO AVENUE 101 Winter Park, FL MLS# G5102278
$260,000
2

Beds

1.0

Baths

804

Sq.Ft.

151 N ORLANDO AVENUE 101

Winter Park, FL

Courtesy of THE FLORIDA PROPERTY SHOP SALE
View 151 N ORLANDO AVENUE 118 Winter Park, FL MLS# O6311340
$299,999
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 118

Winter Park, FL

Courtesy of FLORIDA DREAMS REALTY GRP INC
View 3580 WILDE AVENUE Winter Park, FL MLS# O6296776
$260,000
Studio

Beds

0.0

Baths

3580 WILDE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 2500 LEE ROAD 202 Winter Park, FL MLS# O6277579
$239,990
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 202

Winter Park, FL

Courtesy of THE ANDERSON GROUP & CO PL

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

299

Estimated median home price

$679,000
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 - 100K7
$100K - 200K35
$200K - 300K29
$300K - 400K16
$400K - 500K25
$500K - 600K19
$600K - 700K25
$700K - 800K19
$800K - 900K5
$900K - 1M8
$1M - Max111

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family170
Townhouse18
Condo78
Commercial6
Rental95
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 1/31/2026)

Information deemed reliable but not guaranteed.

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 1/31/2026.