Winter Park Florida Homes for Sale

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377 total properties
Did you mean the neighborhood Winter Park?
View 1597 OAKHURST AVENUE Winter Park, FL MLS# O6436291
  • Recently Listed with Virtual Tour
1 of 81
$2,699,000
5

Beds

4.1

Baths

4,410

Sq.Ft.

1597 OAKHURST AVENUE

Winter Park, FL

View 1550 PALM AVENUE Winter Park, FL MLS# O6436458
  • Recently Listed
1 of 10
$1,829,000
4

Beds

3.1

Baths

2,706

Sq.Ft.

1550 PALM AVENUE

Winter Park, FL

View 2403 EUSTON ROAD Winter Park, FL MLS# O6434678
  • Recently Listed with Virtual Tour
1 of 11
$4,299,000
Studio

Beds

0.0

Baths

2403 EUSTON ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1220 SHARON PLACE Winter Park, FL MLS# O6435525
  • Virtual Tour
1 of 11
$1,800,000
Studio

Beds

0.0

Baths

1220 SHARON PLACE

Winter Park, FL

View 276 DETMAR DRIVE Winter Park, FL MLS# O6434825
  • Recently Listed with Virtual Tour
1 of 81
$3,600,000
4

Beds

5.0

Baths

4,202

Sq.Ft.

276 DETMAR DRIVE

Winter Park, FL

View 751 PANSY AVENUE Winter Park, FL MLS# O6432554
  • Recently Listed with Virtual Tour
1 of 44
$1,950,000
3

Beds

3.1

Baths

2,703

Sq.Ft.

751 PANSY AVENUE

Winter Park, FL

View 150 E READING WAY Winter Park, FL MLS# O6435809
  • Recently Listed with Virtual Tour
1 of 21
$1,495,000
3

Beds

2.1

Baths

2,080

Sq.Ft.

150 E READING WAY

Winter Park, FL

View 1016 ARAGON AVENUE Winter Park, FL MLS# O6435228
  • Recently Listed with Virtual Tour
1 of 32
$660,000
4

Beds

4.0

Baths

1,840

Sq.Ft.

1016 ARAGON AVENUE

Winter Park, FL

View 1016 ARAGON AVENUE Winter Park, FL MLS# O6433576
  • Recently Listed with Virtual Tour
1 of 32
$660,000
4

Beds

2.2

Baths

1,840

Sq.Ft.

1016 ARAGON AVENUE

Winter Park, FL

View 2126 ALBERT LEE PARKWAY Winter Park, FL MLS# O6435973
  • Recently Listed with Virtual Tour
1 of 39
$425,000
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
  • Recently Listed with Virtual Tour
1 of 31
$689,000
3

Beds

3.0

Baths

1,794

Sq.Ft.

900 CARVER STREET

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1941 OGLESBY AVENUE Winter Park, FL MLS# N6145448
  • Recently Listed with 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 1416 BORDER DRIVE Winter Park, FL MLS# O6434966
  • Recently Listed with Virtual Tour
1 of 27
$675,000
3

Beds

1.0

Baths

1,243

Sq.Ft.

1416 BORDER DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1416 BORDER DRIVE Winter Park, FL MLS# O6434973
  • Recently Listed with Virtual Tour
1 of 26
$675,000
Studio

Beds

0.0

Baths

1416 BORDER DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2824 PRINCE JOHN ROAD Winter Park, FL MLS# O6435708
  • Recently Listed with Virtual Tour
1 of 28
$475,000
2

Beds

2.0

Baths

1,438

Sq.Ft.

2824 PRINCE JOHN ROAD

Winter Park, FL

View 1761 LEGION DRIVE Winter Park, FL MLS# O6435967
  • Recently Listed with Virtual Tour
1 of 66
$3,265,000
5

Beds

5.1

Baths

4,924

Sq.Ft.

1761 LEGION DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1621 CHESTNUT AVENUE Winter Park, FL MLS# O6435086
  • Recently Listed with Virtual Tour
1 of 35
$899,000
3

Beds

2.1

Baths

2,022

Sq.Ft.

1621 CHESTNUT AVENUE

Winter Park, FL

View 2333 WESTMINSTER COURT Winter Park, FL MLS# O6435215
  • Recently Listed with Virtual Tour
1 of 40
$664,900
4

Beds

2.0

Baths

1,877

Sq.Ft.

2333 WESTMINSTER COURT

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1526 MILLER AVENUE Winter Park, FL MLS# O6435328
  • Recently Listed
1 of 27
$1,574,900
5

Beds

4.1

Baths

3,252

Sq.Ft.

1526 MILLER AVENUE

Winter Park, FL

View 151 N ORLANDO AVENUE 261 Winter Park, FL MLS# O6435092
  • Recently Listed with Virtual Tour
1 of 26
$239,999
1

Beds

1.0

Baths

582

Sq.Ft.

151 N ORLANDO AVENUE 261

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS

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

377

Estimated median home price

$699,000
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 4
$100K - 200K 41
$200K - 300K 22
$300K - 400K 14
$400K - 500K 38
$500K - 600K 32
$600K - 700K 39
$700K - 800K 13
$800K - 900K 11
$900K - 1M 10
$1M - Max 153

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 230
Townhouse 22
Condo 81
Commercial 9
Rental 80
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 8/27/2026)

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.

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 8/27/2026.