166 total properties
Did you mean the neighborhood Winter Park?
View 2231 NAIRN DRIVE Winter Park, FL MLS# O6426997
$499,000
1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
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 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
$490,900
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

Courtesy of CAISSA REALTY INVESTMENT INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 351 STARLING ROAD Winter Park, FL MLS# O6429698
$489,900
3

Beds

1.1

Baths

1,979

Sq.Ft.

351 STARLING ROAD

Winter Park, FL

Courtesy of HOUWZER INC
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 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 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 981 ARAGON AVENUE Winter Park, FL MLS# O6420093
$474,999
2

Beds

1.0

Baths

857

Sq.Ft.

981 ARAGON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
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 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
$459,900
0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 3334 YOUNG STREET Winter Park, FL MLS# O6442952
$459,900
3

Beds

2.0

Baths

1,706

Sq.Ft.

3334 YOUNG STREET

Winter Park, FL

Courtesy of EQUITYPRO 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 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 506 LANDER ROAD Winter Park, FL MLS# O6451927
  • 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 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
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 JESSICA COURT Winter Park, FL MLS# O6419256
  • Virtual Tour
1 of 11
$449,000
0.0

Baths

JESSICA COURT

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
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 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
$439,000
3

Beds

2.0

Baths

1,606

Sq.Ft.

950 HANOVER AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
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

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

$849,000
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 - 100K4
$100K - 200K32
$200K - 300K24
$300K - 400K17
$400K - 500K31
$500K - 600K23
$600K - 700K26
$700K - 800K18
$800K - 900K17
$900K - 1M12
$1M - Max153

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family211
Townhouse25
Condo79
Commercial15
Rental98
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 11/12/2026)

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.