41 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 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.
The time to sell is now! THE TIME TO SELL IS NOW!
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 624 DUNRAVEN DRIVE Winter Park, FL MLS# O6443159
  • Virtual Tour
1 of 24
$620,000
3

Beds

2.0

Baths

1,762

Sq.Ft.

624 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 808 DENSMORE DRIVE Winter Park, FL MLS# O6451977
  • Recently Listed with Virtual Tour
1 of 26
$509,999
3

Beds

2.0

Baths

1,460

Sq.Ft.

808 DENSMORE DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6449858
  • Virtual Tour
1 of 30
$575,000
3

Beds

2.0

Baths

1,804

Sq.Ft.

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6449843
  • Virtual Tour
1 of 30
$575,000
0.0

Baths

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 731 BONGART ROAD Winter Park, FL MLS# O6448911
$519,900
4

Beds

3.0

Baths

1,842

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 510 FITZWALTER DRIVE Winter Park, FL MLS# O6448189
  • Virtual Tour
1 of 27
$530,000
3

Beds

2.0

Baths

1,385

Sq.Ft.

510 FITZWALTER DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 112 BELL PLACE Winter Park, FL MLS# O6446595
  • Virtual Tour
1 of 31
$575,000
3

Beds

2.0

Baths

2,253

Sq.Ft.

112 BELL PLACE

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6442348
  • Virtual Tour
1 of 41
OPEN HOUSE: Saturday 11/14 12:00 PM - 2:00 PM
$637,500
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 822 SYMONDS AVENUE Winter Park, FL MLS# O6441180
$599,999
0.0

Baths

822 SYMONDS AVENUE

Winter Park, FL

Courtesy of NEWBERRY REALTY & DEV GRP INC.
View 1211 SCHULTZ AVENUE Winter Park, FL MLS# O6442460
  • Virtual Tour
1 of 35
$475,000
3

Beds

2.0

Baths

1,085

Sq.Ft.

1211 SCHULTZ AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 508 BRECHIN DRIVE Winter Park, FL MLS# O6439220
  • Virtual Tour
1 of 34
$579,000
3

Beds

2.0

Baths

1,783

Sq.Ft.

508 BRECHIN DRIVE

Winter Park, FL

Courtesy of MTL REALTY LLC
View 1259 INDIANA AVENUE Winter Park, FL MLS# O6434701
  • Virtual Tour
1 of 67
$575,000
2

Beds

2.1

Baths

1,648

Sq.Ft.

1259 INDIANA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2824 PRINCE JOHN ROAD Winter Park, FL MLS# O6435708
$475,000
2

Beds

2.0

Baths

1,438

Sq.Ft.

2824 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 7525 LODGE POLE TRAIL Winter Park, FL MLS# O6417303
$550,000
4

Beds

2.0

Baths

1,936

Sq.Ft.

7525 LODGE POLE TRAIL

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 565 HUNTINGTON AVENUE 565 Winter Park, FL MLS# O6434796
$635,000
3

Beds

2.1

Baths

2,015

Sq.Ft.

565 HUNTINGTON AVENUE 565

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES

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 11/12/2026.