85 total properties
Did you mean the neighborhood Winter Park?
View 1306 S PENNSYLVANIA AVENUE 5 Winter Park, FL MLS# O6443013
$359,000
2

Beds

1.0

Baths

830

Sq.Ft.

1306 S PENNSYLVANIA AVENUE 5

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 7302 SWALLOW RUN 7302 Winter Park, FL MLS# O6442345
$134,900
2

Beds

2.0

Baths

756

Sq.Ft.

7302 SWALLOW RUN 7302

Winter Park, FL

Courtesy of THE NAVY HOUSE
View 7453 DANIEL WEBSTER DRIVE A5 Winter Park, FL MLS# O6442597
  • Recently Listed with Virtual Tour
1 of 20
$150,000
2

Beds

2.0

Baths

1,063

Sq.Ft.

7453 DANIEL WEBSTER DRIVE A5

Winter Park, FL

Courtesy of LA ROSA REALTY PREMIER LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 3484 SEAGRAPE DRIVE Winter Park, FL MLS# GC543625
  • Virtual Tour
1 of 30
$299,900
4

Beds

2.0

Baths

1,227

Sq.Ft.

3484 SEAGRAPE DRIVE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 4870 SEMINOLE AVENUE Winter Park, FL MLS# O6441887
  • Virtual Tour
1 of 33
$380,000
3

Beds

2.0

Baths

1,277

Sq.Ft.

4870 SEMINOLE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 7476 WOODBURN COURT 38 Winter Park, FL MLS# O6434437
$170,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7476 WOODBURN COURT 38

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3651 N GOLDENROD ROAD C109 Winter Park, FL MLS# O6439897
$165,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD C109

Winter Park, FL

Courtesy of REAL ESTATE PROFESSIONALS SE
View 2626 AMBERGATE ROAD Winter Park, FL MLS# O6439689
  • Virtual Tour
1 of 20
$380,000
3

Beds

1.0

Baths

1,143

Sq.Ft.

2626 AMBERGATE ROAD

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
View 1250 S DENNING DRIVE 127 Winter Park, FL MLS# O6439854
$245,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 127

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2500 LEE ROAD 143 Winter Park, FL MLS# O6438724
$130,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 143

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
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 3020 ANTIQUE OAKS CIRCLE 129 Winter Park, FL MLS# O6438679
$135,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

3020 ANTIQUE OAKS CIRCLE 129

Winter Park, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 3302 ROYAL STREET Winter Park, FL MLS# O6437344
  • Virtual Tour
1 of 17
$269,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

3302 ROYAL STREET

Winter Park, FL

Courtesy of SAND DOLLAR REALTY GROUP INC
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 500 N PENNSYLVANIA AVENUE G Winter Park, FL MLS# G5117377
$349,500
2

Beds

1.0

Baths

709

Sq.Ft.

500 N PENNSYLVANIA AVENUE G

Winter Park, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7530 CRANES CREEK COURT Winter Park, FL MLS# O6436269
$309,900
3

Beds

2.1

Baths

1,545

Sq.Ft.

7530 CRANES CREEK COURT

Winter Park, FL

Courtesy of ROO REALTY LLC
View 1941 OGLESBY AVENUE Winter Park, FL MLS# N6145448
  • Virtual Tour
1 of 30
$340,000
2

Beds

1.0

Baths

780

Sq.Ft.

1941 OGLESBY AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 3019 ANTIQUE OAKS CIRCLE 127 Winter Park, FL MLS# O6434819
$139,998
1

Beds

1.0

Baths

749

Sq.Ft.

3019 ANTIQUE OAKS CIRCLE 127

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 623 GRENADINE COURT 623 Winter Park, FL MLS# O6434195
$194,900
2

Beds

2.0

Baths

1,037

Sq.Ft.

623 GRENADINE COURT 623

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 7468 CANFORD COURT 24 Winter Park, FL MLS# O6433680
$184,900
2

Beds

1.1

Baths

1,365

Sq.Ft.

7468 CANFORD COURT 24

Winter Park, FL

Courtesy of EMPIRE NETWORK 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

373

Estimated median home price

$750,000
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 2
$100K - 200K 39
$200K - 300K 25
$300K - 400K 19
$400K - 500K 32
$500K - 600K 23
$600K - 700K 36
$700K - 800K 22
$800K - 900K 11
$900K - 1M 15
$1M - Max 149

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 220
Townhouse 21
Condo 81
Commercial 14
Rental 91
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 7
Mobile Home 0
Farms 0

(Data as of 10/9/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of Georgia MLS. Real estate listings held by brokerage firms other than Weichert's are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.

© 2026 Georgia MLS. All rights reserved

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 10/10/2026.