283 total properties
Did you mean the neighborhood Winter Park?
View 1021 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6429124
$1,295,000
0.0

Baths

1021 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1850 BRYAN AVENUE Winter Park, FL MLS# O6438184
  • Virtual Tour
1 of 31
OPEN HOUSE: Saturday 10/31 12:00 PM - 2:00 PM
$699,000
3

Beds

2.0

Baths

1,563

Sq.Ft.

1850 BRYAN AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 4039 COOL WATER COURT Winter Park, FL MLS# O6437904
$739,777
4

Beds

2.0

Baths

2,267

Sq.Ft.

4039 COOL WATER COURT

Winter Park, FL

Courtesy of RE/MAX CENTRAL REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 7506 CRANES CREEK COURT 30 Winter Park, FL MLS# S5156844
$365,000
3

Beds

2.1

Baths

1,861

Sq.Ft.

7506 CRANES CREEK COURT 30

Winter Park, FL

Courtesy of TRANSCONTINENTAL REALTY GROUP,
View 1592 ARBOR PARK DRIVE Winter Park, FL MLS# O6438177
$700,000
4

Beds

3.0

Baths

2,016

Sq.Ft.

1592 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7530 CRANES CREEK COURT Winter Park, FL MLS# O6436269
$306,900
3

Beds

2.1

Baths

1,545

Sq.Ft.

7530 CRANES CREEK COURT

Winter Park, FL

Courtesy of ROO REALTY LLC
View 1259 INDIANA AVENUE Winter Park, FL MLS# O6434701
  • Virtual Tour
1 of 67
OPEN HOUSE: Saturday 10/31 1:00 PM - 4:00 PM
$575,000
2

Beds

2.1

Baths

1,648

Sq.Ft.

1259 INDIANA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 471 HOLT AVENUE Winter Park, FL MLS# O6437590
  • Virtual Tour
1 of 27
$925,000
4

Beds

3.0

Baths

2,528

Sq.Ft.

471 HOLT AVENUE

Winter Park, FL

Courtesy of FLORIDA HOME TEAM REALTY LLC
View 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6436367
  • New Construction with Virtual Tour
1 of 64
OPEN HOUSE: Sunday 11/1 2:00 PM - 4:00 PM
$1,550,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 151 N ORLANDO AVENUE 242 Winter Park, FL MLS# O6437574
$269,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 242

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 2207 KINDEL AVENUE Winter Park, FL MLS# O6436815
  • Virtual Tour
1 of 47
$1,575,000
3

Beds

2.1

Baths

2,733

Sq.Ft.

2207 KINDEL AVENUE

Winter Park, FL

Courtesy of THE SIMON SIMAAN GROUP
View 751 PANSY AVENUE Winter Park, FL MLS# O6432554
  • Virtual Tour
1 of 44
$1,875,000
3

Beds

3.1

Baths

2,703

Sq.Ft.

751 PANSY AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1220 HOWELL BRANCH ROAD Winter Park, FL MLS# O6437591
$950,000
3

Beds

2.0

Baths

1,487

Sq.Ft.

1220 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of PARK PLACE REAL ESTATE
View 283 SANDLEWOOD TRAIL 3 Winter Park, FL MLS# O6431475
$279,000
2

Beds

2.1

Baths

960

Sq.Ft.

283 SANDLEWOOD TRAIL 3

Winter Park, FL

Courtesy of RE/MAX INNOVATION
View 1016 ARAGON AVENUE Winter Park, FL MLS# O6433576
  • Virtual Tour
1 of 31
$625,000
4

Beds

2.2

Baths

1,840

Sq.Ft.

1016 ARAGON AVENUE

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 150 E READING WAY Winter Park, FL MLS# O6435809
  • Virtual Tour
1 of 21
$1,399,000
3

Beds

2.1

Baths

2,080

Sq.Ft.

150 E READING WAY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1016 ARAGON AVENUE Winter Park, FL MLS# O6435228
  • Virtual Tour
1 of 31
$625,000
4

Beds

4.0

Baths

1,840

Sq.Ft.

1016 ARAGON AVENUE

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 2126 ALBERT LEE PARKWAY Winter Park, FL MLS# O6435973
$415,000
3

Beds

2.0

Baths

1,187

Sq.Ft.

2126 ALBERT LEE PARKWAY

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 900 CARVER STREET Winter Park, FL MLS# O6435435
  • Virtual Tour
1 of 31
OPEN HOUSE: Saturday 10/31 12:00 PM - 3:00 PM
$659,000
3

Beds

3.0

Baths

1,794

Sq.Ft.

900 CARVER STREET

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1416 BORDER DRIVE Winter Park, FL MLS# O6434966
  • Virtual Tour
1 of 27
$620,000
3

Beds

1.0

Baths

1,243

Sq.Ft.

1416 BORDER DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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

363

Estimated median home price

$825,000
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 3
$100K - 200K 35
$200K - 300K 21
$300K - 400K 15
$400K - 500K 31
$500K - 600K 26
$600K - 700K 33
$700K - 800K 16
$800K - 900K 17
$900K - 1M 13
$1M - Max 153

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 217
Townhouse 23
Condo 78
Commercial 15
Rental 90
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 10/31/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include 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 10/31/2026.

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 10/31/2026.