93 total properties
Did you mean the neighborhood Winter Park?
View 3321 ROYAL STREET Winter Park, FL MLS# A4700206
$280,000
3

Beds

2.0

Baths

1,197

Sq.Ft.

3321 ROYAL STREET

Winter Park, FL

View 846 DRIVER AVENUE Winter Park, FL MLS# O6426024
$325,000
2

Beds

1.0

Baths

824

Sq.Ft.

846 DRIVER AVENUE

Winter Park, FL

View 2568 LOTAFUN AVENUE Winter Park, FL MLS# W7887744
$409,900
3

Beds

2.0

Baths

1,201

Sq.Ft.

2568 LOTAFUN AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 145 SCOTTSDALE SQUARE Winter Park, FL MLS# O6424788
$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
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1 of 15
$169,900
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
$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
$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
$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
$385,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

View 1250 S DENNING DRIVE 109 Winter Park, FL MLS# R4911491
$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
$88,999
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B108

Winter Park, FL

View 252 SCOTTSDALE SQ 252 Winter Park, FL MLS# O6421977
$85,000
2

Beds

1.1

Baths

1,085

Sq.Ft.

252 SCOTTSDALE SQ 252

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

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

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

View 1695 LEE ROAD A116 Winter Park, FL MLS# O6420863
$135,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A116

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 644 N KNOWLES AVENUE 3 Winter Park, FL MLS# O6420484
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1 of 27
OPEN HOUSE: Saturday 8/22 1:30 PM - 3:00 PM
$424,400
1

Beds

1.0

Baths

767

Sq.Ft.

644 N KNOWLES AVENUE 3

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

366

Estimated median home price

$714,950
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 - 200K40
$200K - 300K23
$300K - 400K14
$400K - 500K34
$500K - 600K32
$600K - 700K32
$700K - 800K15
$800K - 900K10
$900K - 1M12
$1M - Max147

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family223
Townhouse22
Condo81
Commercial9
Rental77
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 8/19/2026)

Information deemed reliable but not guaranteed.

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 8/20/2026.