40 total properties
Did you mean the neighborhood Winter Park?
View 257 LINCOLNSHIRE ROAD Winter Park, FL MLS# O6453656
  • Recently Listed with Virtual Tour
1 of 34
$550,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

257 LINCOLNSHIRE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 506 LANDER ROAD Winter Park, FL MLS# O6451927
  • Recently Listed with Virtual Tour
1 of 28
$450,000
3

Beds

2.0

Baths

1,346

Sq.Ft.

506 LANDER ROAD

Winter Park, FL

Courtesy of DERENTHAL REALTY
View 808 DENSMORE DRIVE Winter Park, FL MLS# O6451977
  • Recently Listed with Virtual Tour
1 of 26
OPEN HOUSE: Saturday 10/31 11:00 AM - 2:00 PM
$509,999
3

Beds

2.0

Baths

1,460

Sq.Ft.

808 DENSMORE DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 239 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6445496
$450,000
4

Beds

2.1

Baths

1,866

Sq.Ft.

239 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of CREEGAN GROUP
View 1320 BUCKINGHAM ROAD Winter Park, FL MLS# TB8557402
$449,000
3

Beds

2.0

Baths

1,388

Sq.Ft.

1320 BUCKINGHAM ROAD

Winter Park, FL

Courtesy of PALLADIUM INVESTMENTS INC
View 731 BONGART ROAD Winter Park, FL MLS# O6448911
  • Recently Listed
1 of 51
$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
$530,000
3

Beds

2.0

Baths

1,385

Sq.Ft.

510 FITZWALTER DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2818 AMBERGATE ROAD Winter Park, FL MLS# O6444112
$429,900
3

Beds

2.0

Baths

1,398

Sq.Ft.

2818 AMBERGATE ROAD

Winter Park, FL

Courtesy of MARK SPAIN REAL ESTATE
View 1660 ORANGE AVENUE Winter Park, FL MLS# L4965340
$449,900
3

Beds

2.0

Baths

1,614

Sq.Ft.

1660 ORANGE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 3334 YOUNG STREET Winter Park, FL MLS# O6442952
$469,900
3

Beds

2.0

Baths

1,706

Sq.Ft.

3334 YOUNG STREET

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 3209 HEARTWOOD AVENUE Winter Park, FL MLS# O6442556
$439,900
4

Beds

2.0

Baths

1,627

Sq.Ft.

3209 HEARTWOOD AVENUE

Winter Park, FL

Courtesy of LEDGE REAL ESTATE SOLUTIONS LLC
View 786 W CANTON AVENUE Winter Park, FL MLS# O6441522
$450,000
0.0

Baths

786 W CANTON AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1211 SCHULTZ AVENUE Winter Park, FL MLS# O6442460
$475,000
3

Beds

2.0

Baths

1,085

Sq.Ft.

1211 SCHULTZ AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
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 2641 CARVELL COURT Winter Park, FL MLS# O6430894
  • Virtual Tour
1 of 37
OPEN HOUSE: Saturday 10/31 11:00 AM - 1:00 PM
$525,000
4

Beds

2.0

Baths

2,126

Sq.Ft.

2641 CARVELL COURT

Winter Park, FL

Courtesy of CHAMBERLAIN REALTY LLC
View 2183 CRANDON AVENUE Winter Park, FL MLS# O6433521
$469,000
4

Beds

2.0

Baths

1,200

Sq.Ft.

2183 CRANDON AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1652 BERKSHIRE AVENUE Winter Park, FL MLS# O6432617
$429,000
3

Beds

2.0

Baths

1,498

Sq.Ft.

1652 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2627 AMBERGATE ROAD Winter Park, FL MLS# O6433352
$530,000
4

Beds

3.0

Baths

1,745

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 351 STARLING ROAD Winter Park, FL MLS# O6429698
$499,900
3

Beds

1.1

Baths

1,979

Sq.Ft.

351 STARLING ROAD

Winter Park, FL

Courtesy of HOUWZER INC
View 1061 ARAGON AVENUE 1061 Winter Park, FL MLS# S5152353
$510,000
3

Beds

2.1

Baths

1,669

Sq.Ft.

1061 ARAGON AVENUE 1061

Winter Park, FL

Courtesy of WATSON REALTY CORP

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

355

Estimated median home price

$799,000
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

PriceCount
$0 - 100K3
$100K - 200K34
$200K - 300K20
$300K - 400K16
$400K - 500K32
$500K - 600K25
$600K - 700K35
$700K - 800K16
$800K - 900K15
$900K - 1M13
$1M - Max146

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family211
Townhouse22
Condo76
Commercial15
Rental87
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 10/29/2026)

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 10/30/2026.