82 total properties
Did you mean the neighborhood Winter Park?
View 1083 EASTBROOK BOULEVARD Winter Park, FL MLS# S5136728
$379,990
4

Beds

2.0

Baths

1,530

Sq.Ft.

1083 EASTBROOK BOULEVARD

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 7728 GLENMOOR LANE Winter Park, FL MLS# O6359017
  • Virtual Tour
1 of 30
$379,900
3

Beds

2.0

Baths

1,676

Sq.Ft.

7728 GLENMOOR LANE

Winter Park, FL

Courtesy of KMF REALTY ADVOCATES LLC
View 770 CARVER STREET Winter Park, FL MLS# O6349509
$375,000
4

Beds

1.1

Baths

1,248

Sq.Ft.

770 CARVER STREET

Winter Park, FL

Courtesy of LEGENDS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 3083 CRANE STRAND DRIVE Winter Park, FL MLS# O6360511
$375,000
3

Beds

2.0

Baths

1,200

Sq.Ft.

3083 CRANE STRAND DRIVE

Winter Park, FL

Courtesy of REDFIN CORPORATION
View 1816 AZALEA AVENUE Winter Park, FL MLS# O6369603
  • Recently Listed with Virtual Tour
1 of 26
$369,900
3

Beds

2.0

Baths

1,584

Sq.Ft.

1816 AZALEA AVENUE

Winter Park, FL

Courtesy of GENSTONE REALTY
View 320 GRANADA DRIVE Winter Park, FL MLS# O6299365
  • Virtual Tour
1 of 26
$360,200
3

Beds

2.0

Baths

1,401

Sq.Ft.

320 GRANADA DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 311 E MORSE BOULEVARD 7-5 Winter Park, FL MLS# O6308664
  • Adult Community
1 of 40
$359,000
1

Beds

1.0

Baths

482

Sq.Ft.

311 E MORSE BOULEVARD 7-5

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 150 KILLARNEY BAY COURT 5 Winter Park, FL MLS# O6328063
$355,000
2

Beds

2.0

Baths

1,140

Sq.Ft.

150 KILLARNEY BAY COURT 5

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 3117 SHADY PINE AVENUE Winter Park, FL MLS# O6339255
$355,000
3

Beds

2.0

Baths

1,214

Sq.Ft.

3117 SHADY PINE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 520 KILLARNEY BAY COURT 2 Winter Park, FL MLS# O6361081
$339,000
2

Beds

2.0

Baths

1,160

Sq.Ft.

520 KILLARNEY BAY COURT 2

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 638 WARRENTON ROAD Winter Park, FL MLS# O6324688
  • Virtual Tour
1 of 43
$331,985
2

Beds

2.0

Baths

1,362

Sq.Ft.

638 WARRENTON ROAD

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 2417 PASSAMONTE DRIVE 1E Winter Park, FL MLS# TB8387465
$329,999
3

Beds

2.1

Baths

1,837

Sq.Ft.

2417 PASSAMONTE DRIVE 1E

Winter Park, FL

Courtesy of FLAT FEE MLS REALTY
View 311 E MORSE BOULEVARD 7-11 Winter Park, FL MLS# O6337061
$329,900
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 7-11

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 311 E MORSE BOULEVARD 6-3 Winter Park, FL MLS# O6362964
  • Adult Community with Virtual Tour
1 of 36
$329,000
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 615 WARRENTON ROAD Winter Park, FL MLS# O6356439
  • Virtual Tour
1 of 27
$320,000
2

Beds

2.0

Baths

1,221

Sq.Ft.

615 WARRENTON ROAD

Winter Park, FL

Courtesy of RE/MAX DOWNTOWN
View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$298,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

Courtesy of CREEGAN GROUP
View 1250 S DENNING DRIVE 213 Winter Park, FL MLS# O6344353
$275,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 213

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1500 GAY ROAD 24B Winter Park, FL MLS# O6348568
  • Virtual Tour
1 of 17
$275,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 24B

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 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
  • Virtual Tour
1 of 35
$269,000
2

Beds

1.0

Baths

762

Sq.Ft.

2009 CORNELL AVENUE

Winter Park, FL

Courtesy of ORLANDO HOME DEALER 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

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

Price Count
$0 - 100K 6
$100K - 200K 40
$200K - 300K 21
$300K - 400K 19
$400K - 500K 32
$500K - 600K 26
$600K - 700K 21
$700K - 800K 22
$800K - 900K 5
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 176
Townhouse 19
Condo 77
Commercial 5
Rental 108
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 12/28/2025)

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 12/28/2025.