320 total properties
Did you mean the neighborhood Winter Park?
View 1138 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6420090
$1,050,000
3

Beds

3.0

Baths

2,434

Sq.Ft.

1138 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 981 ARAGON AVENUE Winter Park, FL MLS# O6420093
  • 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 1003 LAKE BELL DRIVE Winter Park, FL MLS# O6418278
  • Virtual Tour
1 of 30
$579,900
3

Beds

2.0

Baths

1,837

Sq.Ft.

1003 LAKE BELL DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View JESSICA COURT Winter Park, FL MLS# O6419256
  • 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
  • Virtual Tour
1 of 64
OPEN HOUSE: Saturday 7/18 1:00 PM - 3:00 PM
$220,000
2

Beds

2.1

Baths

1,578

Sq.Ft.

7488 WHISPERWOOD DRIVE 28

Winter Park, FL

View 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
$1,199,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

View 2625 PARK PLACE DRIVE Winter Park, FL MLS# O6413031
$1,799,000
4

Beds

4.1

Baths

3,460

Sq.Ft.

2625 PARK PLACE DRIVE

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 512 W SWOOPE AVENUE Winter Park, FL MLS# O6417375
  • Virtual Tour
1 of 46
$1,399,000
3

Beds

2.1

Baths

2,585

Sq.Ft.

512 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
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 2361 ROXBURY ROAD Winter Park, FL MLS# O6418164
  • Recently Listed with Virtual Tour
1 of 34
OPEN HOUSE: Saturday 7/18 12:00 PM - 2:00 PM
$599,000
3

Beds

2.0

Baths

1,723

Sq.Ft.

2361 ROXBURY ROAD

Winter Park, FL

View 321 SYLVAN BOULEVARD Winter Park, FL MLS# O6417674
$1,395,000
3

Beds

2.1

Baths

2,821

Sq.Ft.

321 SYLVAN BOULEVARD

Winter Park, FL

View 140 E MORSE BOULEVARD J Winter Park, FL MLS# O6414891
$2,350,000
3

Beds

3.0

Baths

2,143

Sq.Ft.

140 E MORSE BOULEVARD J

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 101 S NEW YORK AVENUE 311 Winter Park, FL MLS# O6416927
$1,849,900
3

Beds

3.1

Baths

3,112

Sq.Ft.

101 S NEW YORK AVENUE 311

Winter Park, FL

View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6418198
  • Virtual Tour
1 of 31
OPEN HOUSE: Saturday 7/18 12:00 PM - 4:00 PM
$1,275,000
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

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 313 SYLVAN DRIVE Winter Park, FL MLS# O6407606
  • New Construction with Virtual Tour
1 of 10
$5,500,000
4

Beds

4.1

Baths

4,775

Sq.Ft.

313 SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1411 MILLER AVENUE Winter Park, FL MLS# O6416926
1 of 37
OPEN HOUSE: Saturday 7/18 12:00 PM - 2:00 PM
$899,000
3

Beds

3.1

Baths

1,824

Sq.Ft.

1411 MILLER AVENUE

Winter Park, FL

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

289

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

Price Count
$0 - 100K 7
$100K - 200K 39
$200K - 300K 16
$300K - 400K 14
$400K - 500K 19
$500K - 600K 22
$600K - 700K 23
$700K - 800K 11
$800K - 900K 10
$900K - 1M 7
$1M - Max 121

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 171
Townhouse 12
Condo 72
Commercial 7
Rental 67
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/17/2026)

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 Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes 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 7/17/2026.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 7/17/2026.