96 total properties
Did you mean the neighborhood Winter Park?
View 7429 DANIEL WEBSTER DRIVE 14 (#C) Winter Park, FL MLS# O6403382
  • Recently Listed with Virtual Tour
1 of 15
$1,740
2

Beds

2.0

Baths

1,036

Sq.Ft.

7429 DANIEL WEBSTER DRIVE 14 (#C)

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1830 STAUNTON AVENUE Winter Park, FL MLS# O6401708
  • Recently Listed with Virtual Tour
1 of 14
$3,200
3

Beds

2.1

Baths

1,590

Sq.Ft.

1830 STAUNTON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1571 MAGNOLIA AVENUE Winter Park, FL MLS# O6401835
  • Recently Listed with Virtual Tour
1 of 31
$2,350
2

Beds

1.1

Baths

922

Sq.Ft.

1571 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 1931 STAUNTON AVENUE Winter Park, FL MLS# O6401484
  • Recently Listed
1 of 11
$2,350
3

Beds

2.0

Baths

1,355

Sq.Ft.

1931 STAUNTON AVENUE

Winter Park, FL

Courtesy of SAND DOLLAR REALTY GROUP INC
View 2176 CRANDON AVENUE Winter Park, FL MLS# O6401803
  • Recently Listed with Virtual Tour
1 of 13
$2,700
2

Beds

1.0

Baths

1,000

Sq.Ft.

2176 CRANDON AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2428 LOTAFUN AVENUE Winter Park, FL MLS# O6401871
  • Recently Listed with Virtual Tour
1 of 7
$3,200
3

Beds

2.1

Baths

1,534

Sq.Ft.

2428 LOTAFUN AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1026 S LAKEMONT AVENUE Winter Park, FL MLS# O6400730
  • Recently Listed with Virtual Tour
1 of 18
$4,300
3

Beds

2.0

Baths

1,470

Sq.Ft.

1026 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of SOTERA LIVING
View 7330 CEDAR CREEK COURT 58 Winter Park, FL MLS# O6400901
  • Recently Listed with Virtual Tour
1 of 12
$1,600
2

Beds

2.1

Baths

1,031

Sq.Ft.

7330 CEDAR CREEK COURT 58

Winter Park, FL

Courtesy of U S GLORY REALTY
View 1041 TUSCANY PLACE Winter Park, FL MLS# O6401030
  • Recently Listed with Virtual Tour
1 of 39
$12,000
4

Beds

3.1

Baths

3,064

Sq.Ft.

1041 TUSCANY PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2911 ANTIQUE OAKS CIRCLE 12 Winter Park, FL MLS# O6400748
  • Recently Listed with Virtual Tour
1 of 18
$1,575
2

Beds

2.0

Baths

1,018

Sq.Ft.

2911 ANTIQUE OAKS CIRCLE 12

Winter Park, FL

Courtesy of CLARA HERRERA REALTY
View 2530 PASSAMONTE DRIVE 10E Winter Park, FL MLS# O6400096
  • Recently Listed with Virtual Tour
1 of 41
$2,600
3

Beds

2.1

Baths

1,837

Sq.Ft.

2530 PASSAMONTE DRIVE 10E

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1947 SUMMERFIELD ROAD Winter Park, FL MLS# O6396107
  • Recently Listed with Virtual Tour
1 of 21
$2,649
3

Beds

2.0

Baths

1,422

Sq.Ft.

1947 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of 407 PROPERTIES
View 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6397874
  • Recently Listed with Virtual Tour
1 of 34
$1,950
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE REALTY
View 1776 MONDRIAN CIRCLE Winter Park, FL MLS# O6400199
  • Recently Listed with Virtual Tour
1 of 44
$5,500
3

Beds

3.1

Baths

2,193

Sq.Ft.

1776 MONDRIAN CIRCLE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1521 CHESTNUT AVENUE Winter Park, FL MLS# A4689928
$6,500
4

Beds

3.0

Baths

2,842

Sq.Ft.

1521 CHESTNUT AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2115 SYCAMORE DRIVE Winter Park, FL MLS# O6398548
  • Recently Listed with Virtual Tour
1 of 23
$3,500
4

Beds

2.0

Baths

2,099

Sq.Ft.

2115 SYCAMORE DRIVE

Winter Park, FL

Courtesy of STOCKWORTH REALTY GROUP
View 7508 GLENMOOR LANE Winter Park, FL MLS# O6399253
  • Recently Listed with Virtual Tour
1 of 60
$2,500
3

Beds

2.0

Baths

1,676

Sq.Ft.

7508 GLENMOOR LANE

Winter Park, FL

Courtesy of AMERICAN DREAM HOMES INC
View 1803 PINEVIEW CIRCLE Winter Park, FL MLS# O6398583
$1,975
2

Beds

1.0

Baths

1,029

Sq.Ft.

1803 PINEVIEW CIRCLE

Winter Park, FL

Courtesy of PREMIER MANAGEMENT GROUP INC
View 3038 ANTIQUE OAKS CIRCLE 165 Winter Park, FL MLS# O6397826
$1,750
2

Beds

2.0

Baths

1,018

Sq.Ft.

3038 ANTIQUE OAKS CIRCLE 165

Winter Park, FL

Courtesy of EXP REALTY LLC
View 151 N ORLANDO AVENUE 203 Winter Park, FL MLS# O6397745
  • Recently Listed with Virtual Tour
1 of 21
$2,300
2

Beds

1.0

Baths

800

Sq.Ft.

151 N ORLANDO AVENUE 203

Winter Park, FL

Courtesy of SAND DOLLAR REALTY GROUP INC

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

371

Estimated median home price

$824,900
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 - 100K4
$100K - 200K49
$200K - 300K23
$300K - 400K19
$400K - 500K29
$500K - 600K18
$600K - 700K27
$700K - 800K16
$800K - 900K12
$900K - 1M10
$1M - Max164

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family226
Townhouse16
Condo87
Commercial4
Rental97
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 4/30/2026)

Information deemed reliable but not guaranteed.

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 4/30/2026.