278 total properties
Did you mean the neighborhood Winter Park?
View 1955 ELAND AVENUE Winter Park, FL MLS# O6433345
$405,000
3

Beds

2.0

Baths

1,494

Sq.Ft.

1955 ELAND AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 150 E READING WAY Winter Park, FL MLS# O6430223
$1,399,000
0.0

Baths

150 E READING WAY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2407 LAFAYETTE AVENUE Winter Park, FL MLS# O6431314
$1,625,000
5

Beds

4.1

Baths

3,133

Sq.Ft.

2407 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 2308 MULBRY DRIVE Winter Park, FL MLS# O6432803
  • New Construction with Virtual Tour
1 of 12
$1,699,000
4

Beds

3.1

Baths

2,530

Sq.Ft.

2308 MULBRY DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1840 BRYAN AVENUE Winter Park, FL MLS# O6431360
$1,725,000
4

Beds

3.1

Baths

3,727

Sq.Ft.

1840 BRYAN AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1695 LEE ROAD D107 Winter Park, FL MLS# O6425124
$180,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD D107

Winter Park, FL

Courtesy of PRIMESTATE REALTY, INC.
View 7413 BELLE RIVER COURT 3 Winter Park, FL MLS# O6430667
$214,900
3

Beds

2.1

Baths

1,151

Sq.Ft.

7413 BELLE RIVER COURT 3

Winter Park, FL

Courtesy of OUTLET REALTY
View 2667 COCHISE TRAIL Winter Park, FL MLS# O6429844
$985,000
4

Beds

3.0

Baths

2,868

Sq.Ft.

2667 COCHISE TRAIL

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 4026 TENITA DRIVE Winter Park, FL MLS# O6430278
$599,000
3

Beds

2.0

Baths

2,031

Sq.Ft.

4026 TENITA DRIVE

Winter Park, FL

Courtesy of RUBY DAVIS, BROKER
View 669 W COMSTOCK AVENUE Winter Park, FL MLS# TB8535201
$210,000
0.0

Baths

669 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of HOMECOIN.COM
View 1927 S LAKEMONT AVENUE Winter Park, FL MLS# O6426102
$915,000
3

Beds

3.1

Baths

2,093

Sq.Ft.

1927 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of IAD REAL ESTATE
View 351 STARLING ROAD Winter Park, FL MLS# O6429698
$499,900
3

Beds

1.1

Baths

1,979

Sq.Ft.

351 STARLING ROAD

Winter Park, FL

Courtesy of HOUWZER INC
View 1000 S SEMORAN BOULEVARD 302 Winter Park, FL MLS# O6428713
$97,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 302

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 1061 ARAGON AVENUE 1061 Winter Park, FL MLS# S5152353
$510,000
3

Beds

2.1

Baths

1,669

Sq.Ft.

1061 ARAGON AVENUE 1061

Winter Park, FL

Courtesy of WATSON REALTY CORP
View 1071 ARAGON AVENUE Winter Park, FL MLS# O6429215
$575,000
2

Beds

2.1

Baths

1,851

Sq.Ft.

1071 ARAGON AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
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 724 MONMOUTH WAY Winter Park, FL MLS# O6424409
  • Virtual Tour
1 of 29
$759,675
5

Beds

3.1

Baths

2,832

Sq.Ft.

724 MONMOUTH WAY

Winter Park, FL

Courtesy of CENTRAL TOWER PROPERTIES
View 1546 MILLER AVENUE Winter Park, FL MLS# O6428019
  • New Construction with Virtual Tour
1 of 36
$1,429,900
4

Beds

3.1

Baths

2,984

Sq.Ft.

1546 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 1000 S SEMORAN BOULEVARD 305 Winter Park, FL MLS# O6428044
$115,000
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 305

Winter Park, FL

Courtesy of MAINFRAME REAL ESTATE
View 230 STRATHY LANE Winter Park, FL MLS# O6426909
$499,000
920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE 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

359

Estimated median home price

$825,000
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 - 100K4
$100K - 200K31
$200K - 300K21
$300K - 400K16
$400K - 500K31
$500K - 600K27
$600K - 700K31
$700K - 800K16
$800K - 900K17
$900K - 1M13
$1M - Max152

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family215
Townhouse24
Condo76
Commercial15
Rental90
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 11/3/2026)

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 11/3/2026.

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 11/3/2026.