192 total properties
Did you mean the neighborhood Winter Park?
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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
View 2231 NAIRN DRIVE Winter Park, FL MLS# O6426997
$499,000
1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 1909 TAYLOR AVENUE Winter Park, FL MLS# O6426549
$425,000
0.0

Baths

1909 TAYLOR AVENUE

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 1562 ARBOR PARK DRIVE Winter Park, FL MLS# O6425628
$775,000
4

Beds

2.1

Baths

1,899

Sq.Ft.

1562 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1500 GAY ROAD 4D Winter Park, FL MLS# O6425078
  • Virtual Tour
1 of 15
$159,900
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 4D

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 901 HARMON AVENUE Winter Park, FL MLS# O6425358
$650,000
2

Beds

2.0

Baths

1,277

Sq.Ft.

901 HARMON AVENUE

Winter Park, FL

Courtesy of STOCKWORTH REALTY GROUP
View 7450 WYNNEWOOD SQUARE 189 Winter Park, FL MLS# O6425486
$170,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7450 WYNNEWOOD SQUARE 189

Winter Park, FL

Courtesy of REAL ESTATE PROFESSIONALS SE
View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
$368,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

Courtesy of RADIUS REALTY GROUP LLC
View 2526 PASSAMONTE DRIVE 10F Winter Park, FL MLS# O6418710
$335,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2526 PASSAMONTE DRIVE 10F

Winter Park, FL

Courtesy of LEGACY CORNERSTONE INC
View 722 S RANGER BOULEVARD Winter Park, FL MLS# O6421873
$775,000
4

Beds

3.0

Baths

2,164

Sq.Ft.

722 S RANGER BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1000 S SEMORAN BOULEVARD 306 Winter Park, FL MLS# R4911525
$138,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 306

Winter Park, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 1000 S SEMORAN BOULEVARD 404 Winter Park, FL MLS# R4911526
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 404

Winter Park, FL

Courtesy of KIMBRIDGE REALTY, LLC
View 1000 S SEMORAN BOULEVARD 408 Winter Park, FL MLS# R4911527
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 408

Winter Park, FL

Courtesy of KIMBRIDGE 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

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.