351 total properties
Did you mean the neighborhood Winter Park?
View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
  • Virtual Tour
1 of 34
$745,000
2

Beds

3.0

Baths

1,440

Sq.Ft.

408 HOLT AVENUE

Winter Park, FL

Courtesy of THE REAL ESTATE PRINCIPLE, INC
View 640 N PARK AVENUE 3 Winter Park, FL MLS# O6446483
$745,000
2

Beds

1.1

Baths

897

Sq.Ft.

640 N PARK AVENUE 3

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 4039 COOL WATER COURT Winter Park, FL MLS# O6437904
$739,777
4

Beds

2.0

Baths

2,267

Sq.Ft.

4039 COOL WATER COURT

Winter Park, FL

Courtesy of RE/MAX CENTRAL REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 250 CAROLINA AVENUE 205 Winter Park, FL MLS# O6433913
$739,000
2

Beds

2.0

Baths

1,311

Sq.Ft.

250 CAROLINA AVENUE 205

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 3377 N FORSYTH ROAD Winter Park, FL MLS# O6173998
$725,000
4,104

Sq.Ft.

3377 N FORSYTH ROAD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 266 N RANGER BOULEVARD Winter Park, FL MLS# O6444727
$724,900
4

Beds

3.0

Baths

1,692

Sq.Ft.

266 N RANGER BOULEVARD

Winter Park, FL

Courtesy of ELITE PROPERTY REAL ESTATE LLC
View 1592 ARBOR PARK DRIVE Winter Park, FL MLS# O6438177
$700,000
4

Beds

3.0

Baths

2,016

Sq.Ft.

1592 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1884 JESSICA COURT Winter Park, FL MLS# O6450978
  • Recently Listed with Virtual Tour
1 of 32
$699,900
3

Beds

2.0

Baths

1,666

Sq.Ft.

1884 JESSICA COURT

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 1850 BRYAN AVENUE Winter Park, FL MLS# O6438184
  • Virtual Tour
1 of 31
OPEN HOUSE: Sunday 10/25 1:00 PM - 3:00 PM
$699,000
3

Beds

2.0

Baths

1,563

Sq.Ft.

1850 BRYAN AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2139 BLOSSOM LANE Winter Park, FL MLS# O6446509
$699,000
0.0

Baths

2139 BLOSSOM LANE

Winter Park, FL

Courtesy of ORLANDO BROTHERS REAL ESTATE LLC
View 715 S RANGER BOULEVARD Winter Park, FL MLS# O6410899
$695,000
4

Beds

3.0

Baths

2,312

Sq.Ft.

715 S RANGER BOULEVARD

Winter Park, FL

Courtesy of DAHLIA REALTY GROUP
View 2831 MULFORD AVENUE Winter Park, FL MLS# O6414319
$695,000
4

Beds

2.1

Baths

1,647

Sq.Ft.

2831 MULFORD AVENUE

Winter Park, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 2887 TEMPLE TRAIL Winter Park, FL MLS# O6450536
  • Recently Listed with Virtual Tour
1 of 86
$695,000
2

Beds

2.1

Baths

1,801

Sq.Ft.

2887 TEMPLE TRAIL

Winter Park, FL

Courtesy of ADAIR REALTY INC
View 2157 LAKE DRIVE Winter Park, FL MLS# O6412258
  • Virtual Tour
1 of 45
$689,000
3

Beds

3.0

Baths

2,124

Sq.Ft.

2157 LAKE DRIVE

Winter Park, FL

Courtesy of SHORES REAL ESTATE
View 432 W SWOOPE AVENUE Winter Park, FL MLS# O6375719
$680,000
4

Beds

3.1

Baths

2,664

Sq.Ft.

432 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2260 COLDSTREAM DRIVE Winter Park, FL MLS# O6437438
  • Virtual Tour
1 of 35
OPEN HOUSE: Saturday 10/24 11:00 AM - 3:00 PM
$675,000
4

Beds

2.0

Baths

1,509

Sq.Ft.

2260 COLDSTREAM DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 433 GILBERT ROAD Winter Park, FL MLS# O6428430
  • Virtual Tour
1 of 36
$669,900
3

Beds

2.0

Baths

1,800

Sq.Ft.

433 GILBERT ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2833 PRINCE JOHN ROAD Winter Park, FL MLS# O6427246
$669,000
4

Beds

2.0

Baths

1,605

Sq.Ft.

2833 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of NETWORTH REALTY OF ORLANDO, LLC
View 1256 MELISSA COURT Winter Park, FL MLS# O6432855
$660,000
3

Beds

3.0

Baths

1,690

Sq.Ft.

1256 MELISSA COURT

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 900 CARVER STREET Winter Park, FL MLS# O6435435
$659,000
3

Beds

3.0

Baths

1,794

Sq.Ft.

900 CARVER STREET

Winter Park, FL

Courtesy of EXP REALTY LLC

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

351

Estimated median home price

$775,000
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 - 100K3
$100K - 200K34
$200K - 300K21
$300K - 400K18
$400K - 500K30
$500K - 600K25
$600K - 700K34
$700K - 800K16
$800K - 900K14
$900K - 1M14
$1M - Max142

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family206
Townhouse22
Condo77
Commercial15
Rental85
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 10/23/2026)

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 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 10/23/2026.

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 10/23/2026.