126 total properties
Did you mean the neighborhood Winter Park?
View 644 N KNOWLES AVENUE 3 Winter Park, FL MLS# O6420484
  • Recently Listed with Virtual Tour
1 of 32
$475,000
1

Beds

1.0

Baths

767

Sq.Ft.

644 N KNOWLES AVENUE 3

Winter Park, FL

View 3037 ANTIQUE OAKS CIRCLE 156 Winter Park, FL MLS# O6420008
  • Recently Listed with Virtual Tour
1 of 21
$154,900
1

Beds

1.0

Baths

749

Sq.Ft.

3037 ANTIQUE OAKS CIRCLE 156

Winter Park, FL

View 3381 CEDAR SPRINGS PLACE 151 Winter Park, FL MLS# O6419959
  • Recently Listed with Virtual Tour
1 of 32
$179,900
2

Beds

2.1

Baths

1,031

Sq.Ft.

3381 CEDAR SPRINGS PLACE 151

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 259 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6419225
  • Recently Listed with Virtual Tour
1 of 26
$465,500
3

Beds

2.0

Baths

1,248

Sq.Ft.

259 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 981 ARAGON AVENUE Winter Park, FL MLS# O6420093
  • Recently Listed with Virtual Tour
1 of 7
$535,000
2

Beds

1.0

Baths

857

Sq.Ft.

981 ARAGON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View JESSICA COURT Winter Park, FL MLS# O6419256
  • Recently Listed with Virtual Tour
1 of 11
$449,000
Studio

Beds

0.0

Baths

JESSICA COURT

Winter Park, FL

View 751 WARRENTON ROAD Winter Park, FL MLS# TB8522073
  • Virtual Tour
1 of 16
$319,900
3

Beds

2.0

Baths

1,196

Sq.Ft.

751 WARRENTON ROAD

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6419422
$229,900
2

Beds

1.1

Baths

1,219

Sq.Ft.

Address not provided

Winter Park, FL

View 7488 WHISPERWOOD DRIVE 28 Winter Park, FL MLS# O6419151
  • Recently Listed with Virtual Tour
1 of 64
$230,000
2

Beds

2.1

Baths

1,578

Sq.Ft.

7488 WHISPERWOOD DRIVE 28

Winter Park, FL

View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Virtual Tour
1 of 26
$248,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

View 4053 COOL WATER COURT Winter Park, FL MLS# O6419831
$549,000
3

Beds

2.0

Baths

1,930

Sq.Ft.

4053 COOL WATER COURT

Winter Park, FL

View 4756 TANGERINE AVENUE 4756 Winter Park, FL MLS# R4911483
$195,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4756 TANGERINE AVENUE 4756

Winter Park, FL

View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Adult Community with Virtual Tour
1 of 24
$254,900
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

Winter Park, FL

View 2715 PRINCE JOHN ROAD Winter Park, FL MLS# O6415084
$498,900
3

Beds

2.0

Baths

1,565

Sq.Ft.

2715 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of VIA PROPERTIES LLC
View 2974 CHANTILLY AVENUE Winter Park, FL MLS# O6412851
$499,000
3

Beds

2.0

Baths

1,433

Sq.Ft.

2974 CHANTILLY AVENUE

Winter Park, FL

View 151 NORTH ORLANDO AVENUE 142 Winter Park, FL MLS# O6412768
$199,900
1

Beds

1.0

Baths

582

Sq.Ft.

151 NORTH ORLANDO AVENUE 142

Winter Park, FL

View 685 OVERSPIN DRIVE Winter Park, FL MLS# O6415537
$629,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

685 OVERSPIN DRIVE

Winter Park, FL

View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
  • Virtual Tour
1 of 37
$560,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 311 E MORSE BOULEVARD 6-12 Winter Park, FL MLS# O6413554
$275,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 6-12

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2006 CORNELL AVENUE Winter Park, FL MLS# O6412789
  • Virtual Tour
1 of 28
$338,000
2

Beds

1.0

Baths

797

Sq.Ft.

2006 CORNELL AVENUE

Winter Park, FL

Courtesy of FLORIDA HOME TEAM 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

306

Estimated median home price

$735,000
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 4
$100K - 200K 41
$200K - 300K 18
$300K - 400K 14
$400K - 500K 25
$500K - 600K 21
$600K - 700K 24
$700K - 800K 11
$800K - 900K 11
$900K - 1M 5
$1M - Max 132

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 186
Townhouse 14
Condo 73
Commercial 7
Rental 72
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/10/2026)

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 7/11/2026.