165 total properties
Did you mean the neighborhood Winter Park?
View 535 N INTERLACHEN AVENUE 302 Winter Park, FL MLS# O6452921
  • Recently Listed with Virtual Tour
1 of 33
$485,000
2

Beds

2.0

Baths

970

Sq.Ft.

535 N INTERLACHEN AVENUE 302

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1934 TAYLOR AVENUE Winter Park, FL MLS# O6455676
  • Recently Listed with Virtual Tour
1 of 42
$499,000
4

Beds

1.1

Baths

1,470

Sq.Ft.

1934 TAYLOR AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 2885 ROXBURY ROAD Winter Park, FL MLS# O6456440
  • Recently Listed with Virtual Tour
1 of 20
$450,000
3

Beds

2.0

Baths

1,511

Sq.Ft.

2885 ROXBURY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 662 TRINIDAD COURT 662 Winter Park, FL MLS# O6456448
  • Recently Listed with Virtual Tour
1 of 50
$177,000
1

Beds

1.0

Baths

759

Sq.Ft.

662 TRINIDAD COURT 662

Winter Park, FL

Courtesy of CLARA HERRERA REALTY
View 640 N PARK AVENUE 26 Winter Park, FL MLS# O6456509
  • Recently Listed with Virtual Tour
1 of 19
$629,500
2

Beds

2.0

Baths

858

Sq.Ft.

640 N PARK AVENUE 26

Winter Park, FL

Courtesy of MICHAEL O'SHAUGHNESSY, INC.
View 1140 WASHINGTON AVENUE 16C Winter Park, FL MLS# O6456091
  • Recently Listed with Virtual Tour
1 of 10
OPEN HOUSE: Friday 11/13 4:00 PM - 7:00 PM
$739,000
3

Beds

2.1

Baths

2,069

Sq.Ft.

1140 WASHINGTON AVENUE 16C

Winter Park, FL

Courtesy of CHEVON EATON
View 2176 CRANDON AVENUE Winter Park, FL MLS# O6455726
  • Recently Listed with Virtual Tour
1 of 19
$399,000
2

Beds

1.0

Baths

959

Sq.Ft.

2176 CRANDON AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 3157 SHADY PINE AVENUE Winter Park, FL MLS# O6455299
  • Recently Listed with Virtual Tour
1 of 31
$425,000
3

Beds

2.0

Baths

1,495

Sq.Ft.

3157 SHADY PINE AVENUE

Winter Park, FL

Courtesy of MID-STATE PROPERTIES PSL LLC
View 700 MELROSE AVENUE B23 Winter Park, FL MLS# O6455185
  • Recently Listed with Virtual Tour
1 of 31
$295,000
2

Beds

2.0

Baths

1,074

Sq.Ft.

700 MELROSE AVENUE B23

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 3019 ANTIQUE OAKS CIRCLE 127 Winter Park, FL MLS# O6455101
$139,998
1

Beds

1.0

Baths

749

Sq.Ft.

3019 ANTIQUE OAKS CIRCLE 127

Winter Park, FL

Courtesy of CHEVON EATON
View 220 KILLARNEY BAY COURT 6-2 Winter Park, FL MLS# O6450663
$335,000
2

Beds

2.0

Baths

1,140

Sq.Ft.

220 KILLARNEY BAY COURT 6-2

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1261 MICHIGAN AVENUE Winter Park, FL MLS# O6450090
  • Recently Listed with Virtual Tour
1 of 42
OPEN HOUSE: Saturday 11/14 1:00 PM - 3:00 PM
$650,000
3

Beds

2.1

Baths

1,798

Sq.Ft.

1261 MICHIGAN AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 700 MELROSE AVENUE A22 Winter Park, FL MLS# S5160491
  • Recently Listed with Virtual Tour
1 of 44
$325,000
2

Beds

2.0

Baths

1,074

Sq.Ft.

700 MELROSE AVENUE A22

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 200 ST ANDREWS BOULEVARD 906 Winter Park, FL MLS# O6453614
$175,000
1

Beds

1.0

Baths

727

Sq.Ft.

200 ST ANDREWS BOULEVARD 906

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3462 SEAGRAPE DRIVE Winter Park, FL MLS# O6453385
  • Virtual Tour
1 of 28
$225,000
3

Beds

1.0

Baths

1,227

Sq.Ft.

3462 SEAGRAPE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 4940 TANGERINE AVENUE 4940 Winter Park, FL MLS# O6450304
  • Recently Listed with Virtual Tour
1 of 66
$249,000
3

Beds

2.0

Baths

1,345

Sq.Ft.

4940 TANGERINE AVENUE 4940

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3027 AARON BUR AVENUE L1 Winter Park, FL MLS# TB8562681
  • Recently Listed with Virtual Tour
1 of 32
$169,999
2

Beds

2.1

Baths

1,090

Sq.Ft.

3027 AARON BUR AVENUE L1

Winter Park, FL

Courtesy of HOMESMART
View 257 LINCOLNSHIRE ROAD Winter Park, FL MLS# O6453656
$550,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

257 LINCOLNSHIRE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2141 LAKE DRIVE Winter Park, FL MLS# O6453477
  • Virtual Tour
1 of 25
$569,900
3

Beds

2.0

Baths

1,824

Sq.Ft.

2141 LAKE DRIVE

Winter Park, FL

Courtesy of SHORES REAL ESTATE
View 7463 CANFORD COURT 15 Winter Park, FL MLS# O6452947
  • Recently Listed
1 of 44
$270,000
3

Beds

2.1

Baths

1,580

Sq.Ft.

7463 CANFORD COURT 15

Winter Park, FL

Courtesy of EXP 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

357

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

Price Count
$0 - 100K 4
$100K - 200K 32
$200K - 300K 23
$300K - 400K 18
$400K - 500K 32
$500K - 600K 24
$600K - 700K 26
$700K - 800K 18
$800K - 900K 17
$900K - 1M 12
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 210
Townhouse 25
Condo 80
Commercial 15
Rental 96
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 11/11/2026)

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 11/11/2026.