118 total properties
Did you mean the neighborhood Winter Park?
View 2748 LION HEART ROAD Winter Park, FL MLS# O6379237
$500,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

2748 LION HEART ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 240 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6330690
$499,900
4

Beds

2.0

Baths

1,718

Sq.Ft.

240 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of A+ REALTY PROFESSIONALS, INC
View 2560 Franklin Ave. Winter Park, FL MLS# F10431070
$499,000
4

Beds

2.0

Baths

1,514

Sq.Ft.

2560 Franklin Ave.

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 3718 N Goldenrod Road Winter Park, FL MLS# A11792799
$499,000
Studio

Beds

0.0

Baths

3718 N Goldenrod Road

Winter Park, FL

Courtesy of PROCLOSE REALTY, LLC.
View 230 STRATHY LANE Winter Park, FL MLS# O6371054
  • Virtual Tour
1 of 12
$499,000
2

Beds

1.0

Baths

920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 2231 NAIRN DRIVE Winter Park, FL MLS# O6369016
  • Virtual Tour
1 of 19
$499,000
3

Beds

2.0

Baths

1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 3207 LOWNDES DRIVE Winter Park, FL MLS# O6362285
$499,000
3

Beds

2.0

Baths

2,028

Sq.Ft.

3207 LOWNDES DRIVE

Winter Park, FL

Courtesy of MILLER GRANT AND COMPANY
View 346 S RANGER BOULEVARD Winter Park, FL MLS# S5134662
$495,000
3

Beds

2.0

Baths

1,592

Sq.Ft.

346 S RANGER BOULEVARD

Winter Park, FL

Courtesy of IMPERIAL REALTY OF FLORIDA INC
View 958 HANOVER AVENUE Winter Park, FL MLS# O6388088
  • Recently Listed with Virtual Tour
1 of 34
$490,000
4

Beds

3.0

Baths

1,378

Sq.Ft.

958 HANOVER AVENUE

Winter Park, FL

Courtesy of AGILE GROUP REALTY
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
$489,000
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 3312 HEARTWOOD AVENUE Winter Park, FL MLS# O6352582
$484,000
4

Beds

3.0

Baths

2,878

Sq.Ft.

3312 HEARTWOOD AVENUE

Winter Park, FL

Courtesy of MID-STATE PROPERTIES PSL LLC
View 764 W COMSTOCK AVENUE Winter Park, FL MLS# O6379596
$474,000
2

Beds

1.0

Baths

925

Sq.Ft.

764 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2774 BANCHORY ROAD Winter Park, FL MLS# O6328091
$470,000
3

Beds

2.0

Baths

1,560

Sq.Ft.

2774 BANCHORY ROAD

Winter Park, FL

Courtesy of THE PALMS PROPERTY GROUP
View 1564 CAVENDISH ROAD Winter Park, FL MLS# O6380505
$470,000
2

Beds

1.0

Baths

1,140

Sq.Ft.

1564 CAVENDISH ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7618 WAUNATTA COURT Winter Park, FL MLS# V4946886
$460,000
3

Beds

3.0

Baths

1,970

Sq.Ft.

7618 WAUNATTA COURT

Winter Park, FL

Courtesy of PHOENIX REALTY ADVISORS LLC
View 640 N PARK AVENUE 5 Winter Park, FL MLS# O6367841
$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 714 DENTON ROAD Winter Park, FL MLS# O6362464
  • Virtual Tour
1 of 27
$449,500
3

Beds

3.0

Baths

1,786

Sq.Ft.

714 DENTON ROAD

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 3642 PERIWINKLE DRIVE Winter Park, FL MLS# O6341725
$445,000
5

Beds

3.0

Baths

1,945

Sq.Ft.

3642 PERIWINKLE DRIVE

Winter Park, FL

Courtesy of HONEST REAL ESTATE COMPANY
View 1347 ORCHID AVENUE Winter Park, FL MLS# S5140042
$444,900
4

Beds

2.0

Baths

1,490

Sq.Ft.

1347 ORCHID AVENUE

Winter Park, FL

Courtesy of SHELDON PROFESSIONALS INC
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

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

314

Estimated median home price

$725,000
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 - 100K5
$100K - 200K38
$200K - 300K31
$300K - 400K19
$400K - 500K25
$500K - 600K17
$600K - 700K18
$700K - 800K21
$800K - 900K7
$900K - 1M8
$1M - Max125

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family180
Townhouse15
Condo83
Commercial4
Rental78
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 3/6/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 3/6/2026.

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 3/6/2026.

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 3/6/2026.