320 total properties
Did you mean the neighborhood Winter Park?
View 675 OVERSPIN DRIVE Winter Park, FL MLS# O6378975
  • Recently Listed with Virtual Tour
1 of 32
$800,000
4

Beds

3.1

Baths

3,062

Sq.Ft.

675 OVERSPIN DRIVE

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
View 1500 GAY ROAD 5 Winter Park, FL MLS# S5143213
  • Recently Listed with Virtual Tour
1 of 17
$195,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 5

Winter Park, FL

Courtesy of TRANSCEND REALTY
View 1137 OAKS BOULEVARD Winter Park, FL MLS# O6379388
  • Recently Listed
1 of 29
$644,900
2

Beds

1.1

Baths

1,149

Sq.Ft.

1137 OAKS BOULEVARD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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 151 OAKWOOD WAY Winter Park, FL MLS# O6380037
  • Recently Listed
1 of 75
$3,180,000
4

Beds

4.1

Baths

4,129

Sq.Ft.

151 OAKWOOD WAY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 4872 ORANGE AVENUE Winter Park, FL MLS# O6380333
  • Recently Listed with Virtual Tour
1 of 18
$375,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

4872 ORANGE AVENUE

Winter Park, FL

Courtesy of ALFA REAL ESTATE LLC
View 234 DETMAR DRIVE Winter Park, FL MLS# O6379927
  • Recently Listed with Virtual Tour
1 of 45
$1,695,000
5

Beds

5.1

Baths

3,609

Sq.Ft.

234 DETMAR DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2412 CHANTILLY AVENUE Winter Park, FL MLS# O6381552
$2,395,000
5

Beds

6.1

Baths

4,506

Sq.Ft.

2412 CHANTILLY AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6381988
$1,950,000
4

Beds

4.0

Baths

2,810

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1113 VIA DEL MAR Winter Park, FL MLS# O6379697
  • Recently Listed with Virtual Tour
1 of 9
$1,595,000
3

Beds

2.0

Baths

2,012

Sq.Ft.

1113 VIA DEL MAR

Winter Park, FL

Courtesy of BAY HILL REALTY LLC
View 7508 GLENMOOR LANE Winter Park, FL MLS# O6379312
$359,900
3

Beds

2.0

Baths

1,676

Sq.Ft.

7508 GLENMOOR LANE

Winter Park, FL

Courtesy of THE TEAM REAL ESTATE GROUP INC
View 1000 S SEMORAN BOULEVARD 512 Winter Park, FL MLS# O6379459
  • Recently Listed with Virtual Tour
1 of 11
$128,500
2

Beds

2.0

Baths

1,072

Sq.Ft.

1000 S SEMORAN BOULEVARD 512

Winter Park, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 831/833 HUNTINGTON COURT Winter Park, FL MLS# O6378801
$1,100,000
6

Beds

4.0

Baths

2,915

Sq.Ft.

831/833 HUNTINGTON COURT

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1742 TEMPLE DRIVE Winter Park, FL MLS# O6378905
  • Recently Listed with Virtual Tour
1 of 73
$3,549,995
4

Beds

5.0

Baths

3,658

Sq.Ft.

1742 TEMPLE DRIVE

Winter Park, FL

Courtesy of ROI AVE LLC
View 2015 N PARK AVENUE Winter Park, FL MLS# O6372603
  • Recently Listed with Virtual Tour
1 of 62
$2,495,000
5

Beds

4.1

Baths

3,963

Sq.Ft.

2015 N PARK AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 200 SAINT ANDREWS BOULEVARD 2302 Winter Park, FL MLS# O6377760
$195,000
2

Beds

2.0

Baths

987

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2302

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1860 STAUNTON AVENUE Winter Park, FL MLS# O6378554
  • Recently Listed with Virtual Tour
1 of 10
$1,195,000
4

Beds

3.1

Baths

2,525

Sq.Ft.

1860 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
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 100 S INTERLACHEN AVENUE 404 Winter Park, FL MLS# O6375851
$1,165,000
2

Beds

2.0

Baths

1,634

Sq.Ft.

100 S INTERLACHEN AVENUE 404

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 501 DARCEY DRIVE Winter Park, FL MLS# O6378578
  • Virtual Tour
1 of 39
$1,675,000
5

Beds

4.1

Baths

3,033

Sq.Ft.

501 DARCEY DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE

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

319

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

PriceCount
$0 - 100K6
$100K - 200K38
$200K - 300K32
$300K - 400K19
$400K - 500K25
$500K - 600K17
$600K - 700K23
$700K - 800K20
$800K - 900K7
$900K - 1M7
$1M - Max125

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family179
Townhouse17
Condo86
Commercial5
Rental82
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 2/22/2026)

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 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 2/22/2026.

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 2/22/2026.

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 2/22/2026.