122 total properties
Did you mean the neighborhood Winter Park?
View 200 SAINT ANDREWS BOULEVARD 2904 Winter Park, FL MLS# O6427536
  • Recently Listed with Virtual Tour
1 of 21
$230,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2904

Winter Park, FL

View 230 STRATHY LANE Winter Park, FL MLS# O6426909
  • Recently Listed
1 of 2
$499,000
920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

View 2231 NAIRN DRIVE Winter Park, FL MLS# O6426997
  • Recently Listed
1 of 2
$499,000
1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1909 TAYLOR AVENUE Winter Park, FL MLS# O6426549
$425,000
Studio

Beds

0.0

Baths

1909 TAYLOR AVENUE

Winter Park, FL

View 3321 ROYAL STREET Winter Park, FL MLS# A4700206
  • Recently Listed with Virtual Tour
1 of 20
$280,000
3

Beds

2.0

Baths

1,197

Sq.Ft.

3321 ROYAL STREET

Winter Park, FL

View 3373 CEDAR SPRINGS PLACE 149 Winter Park, FL MLS# O6426224
  • Recently Listed with Virtual Tour
1 of 62
$169,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

3373 CEDAR SPRINGS PLACE 149

Winter Park, FL

View 846 DRIVER AVENUE Winter Park, FL MLS# O6426024
  • Recently Listed with Virtual Tour
1 of 25
$310,000
2

Beds

1.0

Baths

824

Sq.Ft.

846 DRIVER AVENUE

Winter Park, FL

View 2568 LOTAFUN AVENUE Winter Park, FL MLS# W7887744
  • Recently Listed with Virtual Tour
1 of 25
$409,900
3

Beds

2.0

Baths

1,201

Sq.Ft.

2568 LOTAFUN AVENUE

Winter Park, FL

View 145 SCOTTSDALE SQUARE Winter Park, FL MLS# O6424788
  • Recently Listed with Virtual Tour
1 of 33
$99,900
2

Beds

2.0

Baths

1,020

Sq.Ft.

145 SCOTTSDALE SQUARE

Winter Park, FL

View 1500 GAY ROAD 4D Winter Park, FL MLS# O6425078
  • Recently Listed with Virtual Tour
1 of 15
$175,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 4D

Winter Park, FL

View 7450 WYNNEWOOD SQUARE 189 Winter Park, FL MLS# O6425486
  • Recently Listed with Virtual Tour
1 of 41
$185,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7450 WYNNEWOOD SQUARE 189

Winter Park, FL

View 263 SCOTTSDALE SQUARE 263 Winter Park, FL MLS# O6424619
$80,000
2

Beds

2.0

Baths

1,020

Sq.Ft.

263 SCOTTSDALE SQUARE 263

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2526 PASSAMONTE DRIVE 10F Winter Park, FL MLS# O6418710
  • Recently Listed with Virtual Tour
1 of 10
$335,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2526 PASSAMONTE DRIVE 10F

Winter Park, FL

View 303 SCOTTSDALE SQUARE 303 Winter Park, FL MLS# O6424296
$80,000
2

Beds

2.0

Baths

1,020

Sq.Ft.

303 SCOTTSDALE SQUARE 303

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 4965 ORANGE AVENUE Winter Park, FL MLS# O6423739
  • Recently Listed with Virtual Tour
1 of 29
$379,900
4

Beds

2.0

Baths

1,444

Sq.Ft.

4965 ORANGE AVENUE

Winter Park, FL

View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
  • Recently Listed with Virtual Tour
1 of 38
$375,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

View 3360 ROYAL STREET Winter Park, FL MLS# O6423106
  • Recently Listed with Virtual Tour
1 of 15
$179,900
2

Beds

1.1

Baths

981

Sq.Ft.

3360 ROYAL STREET

Winter Park, FL

View 1250 S DENNING DRIVE 109 Winter Park, FL MLS# R4911491
  • Recently Listed with Virtual Tour
1 of 27
$190,000
1

Beds

1.0

Baths

658

Sq.Ft.

1250 S DENNING DRIVE 109

Winter Park, FL

View 1500 GAY ROAD 18D Winter Park, FL MLS# O6422691
$275,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 18D

Winter Park, FL

View 1695 LEE ROAD B108 Winter Park, FL MLS# O6422568
  • Recently Listed with Virtual Tour
1 of 15
$89,999
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B108

Winter Park, FL

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

381

Estimated median home price

$799,000
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 - 100K7
$100K - 200K43
$200K - 300K24
$300K - 400K18
$400K - 500K29
$500K - 600K24
$600K - 700K33
$700K - 800K14
$800K - 900K15
$900K - 1M9
$1M - Max165

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family233
Townhouse20
Condo84
Commercial11
Rental68
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 7/23/2026)

Information deemed reliable but not guaranteed.

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 7/23/2026.