20 total properties
Did you mean the neighborhood Winter Park?
View 173 SCOTTSDALE SQUARE 173 Winter Park, FL MLS# S5158339
  • Recently Listed with Virtual Tour
1 of 13
$100,000
1

Beds

1.0

Baths

785

Sq.Ft.

173 SCOTTSDALE SQUARE 173

Winter Park, FL

Courtesy of AXEN REALTY, LLC
View 1695 LEE ROAD C206 Winter Park, FL MLS# TB8551269
  • Recently Listed with Virtual Tour
1 of 24
$140,000
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD C206

Winter Park, FL

Courtesy of INVESTMENT REALTY
View 7302 SWALLOW RUN 7302 Winter Park, FL MLS# O6442345
  • Recently Listed with Virtual Tour
1 of 24
$134,900
2

Beds

2.0

Baths

756

Sq.Ft.

7302 SWALLOW RUN 7302

Winter Park, FL

Courtesy of THE NAVY HOUSE
The time to sell is now! THE TIME TO SELL IS NOW!
View 7453 DANIEL WEBSTER DRIVE A5 Winter Park, FL MLS# O6442597
  • Recently Listed with Virtual Tour
1 of 20
$150,000
2

Beds

2.0

Baths

1,063

Sq.Ft.

7453 DANIEL WEBSTER DRIVE A5

Winter Park, FL

Courtesy of LA ROSA REALTY PREMIER LLC
View 2500 LEE ROAD 143 Winter Park, FL MLS# O6438724
$130,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 143

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 3020 ANTIQUE OAKS CIRCLE 129 Winter Park, FL MLS# O6438679
$135,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

3020 ANTIQUE OAKS CIRCLE 129

Winter Park, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 3019 ANTIQUE OAKS CIRCLE 127 Winter Park, FL MLS# O6434819
$143,500
1

Beds

1.0

Baths

749

Sq.Ft.

3019 ANTIQUE OAKS CIRCLE 127

Winter Park, FL

View 1695 LEE ROAD A101 Winter Park, FL MLS# O6429942
$154,900
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A101

Winter Park, FL

Courtesy of CINO INTERNATIONAL INC
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

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 1000 S SEMORAN BOULEVARD 302 Winter Park, FL MLS# O6428713
$105,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 302

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 3021 AARON BURR AVENUE 3 Winter Park, FL MLS# S5147382
$140,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3021 AARON BURR AVENUE 3

Winter Park, FL

Courtesy of NAIM REAL ESTATE LLC
View 1695 LEE ROAD D211 Winter Park, FL MLS# O6396190
$102,500
2

Beds

1.0

Baths

881

Sq.Ft.

1695 LEE ROAD D211

Winter Park, FL

Courtesy of LOKATION
View 1695 LEE ROAD B210 Winter Park, FL MLS# O6375872
$89,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B210

Winter Park, FL

Courtesy of GM SUNSHINE REALTY LLC
View 311 SCOTTSDALE SQUARE 311 Winter Park, FL MLS# O6355536
$109,400
1

Beds

1.0

Baths

785

Sq.Ft.

311 SCOTTSDALE SQUARE 311

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2948 ANTIQUE OAKS CIRCLE 94 Winter Park, FL MLS# O6342254
$150,000
1

Beds

1.0

Baths

749

Sq.Ft.

2948 ANTIQUE OAKS CIRCLE 94

Winter Park, FL

View 3071 GEORGE MASON AVENUE 5 Winter Park, FL MLS# O6289736
$89,900
1.0

Baths

549

Sq.Ft.

3071 GEORGE MASON AVENUE 5

Winter Park, FL

Courtesy of CASTLE & COTTAGE 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

388

Estimated median home price

$798,500
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 - 200K40
$200K - 300K23
$300K - 400K18
$400K - 500K34
$500K - 600K23
$600K - 700K35
$700K - 800K20
$800K - 900K12
$900K - 1M19
$1M - Max161

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family234
Townhouse20
Condo83
Commercial12
Rental87
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 10/3/2026)

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 10/3/2026.