66 total properties
Did you mean the neighborhood Winter Park?
View 170 BALFOUR DRIVE 1 Winter Park, FL MLS# O6446433
  • Recently Listed with Virtual Tour
1 of 45
$299,000
2

Beds

2.0

Baths

1,032

Sq.Ft.

170 BALFOUR DRIVE 1

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 200 SAINT ANDREWS BOULEVARD 3408 Winter Park, FL MLS# O6446586
  • Recently Listed with Virtual Tour
1 of 11
$170,000
1

Beds

1.0

Baths

793

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 3408

Winter Park, FL

Courtesy of PARK 26 REALTY LLC
View 2500 LEE ROAD 123 Winter Park, FL MLS# O6445068
  • Recently Listed with Virtual Tour
1 of 32
$169,900
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 123

Winter Park, FL

Courtesy of HOME WISE REALTY GROUP, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 200 SAINT ANDREWS BOULEVARD 704 Winter Park, FL MLS# O6445691
  • Recently Listed with Virtual Tour
1 of 40
$159,000
1

Beds

1.0

Baths

793

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 704

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1250 S DENNING DRIVE 119 Winter Park, FL MLS# O6444618
  • Recently Listed with Virtual Tour
1 of 31
$265,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 119

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 450 N LAKEMONT AVE Winter Park, FL MLS# O6445021
  • Recently Listed with Virtual Tour
1 of 25
$200,000

450 N LAKEMONT AVE

Winter Park, FL

Courtesy of DOVER INTERNATIONAL CO., INC.
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 188 SANDLEWOOD 1 Winter Park, FL MLS# O6445407
  • Recently Listed with Virtual Tour
1 of 25
$290,000
2

Beds

2.1

Baths

1,133

Sq.Ft.

188 SANDLEWOOD 1

Winter Park, FL

Courtesy of NOELKE REALTY
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 602 TRINIDAD COURT 602 Winter Park, FL MLS# O6443577
  • Recently Listed with Virtual Tour
1 of 31
$227,000
2

Beds

2.0

Baths

1,120

Sq.Ft.

602 TRINIDAD COURT 602

Winter Park, FL

Courtesy of CLARA HERRERA 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
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 3484 SEAGRAPE DRIVE Winter Park, FL MLS# GC543625
  • Virtual Tour
1 of 30
$299,900
4

Beds

2.0

Baths

1,227

Sq.Ft.

3484 SEAGRAPE DRIVE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 7476 WOODBURN COURT 38 Winter Park, FL MLS# O6434437
  • Recently Listed
1 of 28
$170,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7476 WOODBURN COURT 38

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3651 N GOLDENROD ROAD C109 Winter Park, FL MLS# O6439897
$165,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD C109

Winter Park, FL

View 1250 S DENNING DRIVE 127 Winter Park, FL MLS# O6439854
$245,000
2

Beds

2.0

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 127

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
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 3651 N GOLDENROD ROAD C205 Winter Park, FL MLS# O6438227
$159,900
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD C205

Winter Park, FL

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 3302 ROYAL STREET Winter Park, FL MLS# O6437344
  • Virtual Tour
1 of 17
$269,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

3302 ROYAL STREET

Winter Park, FL

Courtesy of SAND DOLLAR REALTY GROUP INC

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

Price Count
$0 - 100K 3
$100K - 200K 40
$200K - 300K 23
$300K - 400K 18
$400K - 500K 34
$500K - 600K 23
$600K - 700K 35
$700K - 800K 20
$800K - 900K 12
$900K - 1M 19
$1M - Max 161

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 234
Townhouse 20
Condo 83
Commercial 12
Rental 87
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 7
Mobile Home 0
Farms 0

(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.