87 total properties
Did you mean the neighborhood Winter Park?
View 2113 Shadow View Circel 2113 Winter Park, FL MLS# A11741510
$2,300
3

Beds

2.1

Baths

1,583

Sq.Ft.

2113 Shadow View Circel 2113

Winter Park, FL

Courtesy of REALTY ICONIC, LLC.
View 2886 CAREW AVENUE Winter Park, FL MLS# O6331998
  • Virtual Tour
1 of 29
$2,350
4

Beds

2.1

Baths

1,701

Sq.Ft.

2886 CAREW AVENUE

Winter Park, FL

Courtesy of THE TEAM REAL ESTATE GROUP INC
View 1148 PARK GREEN PLACE Winter Park, FL MLS# O6352263
$2,350
3

Beds

2.0

Baths

1,282

Sq.Ft.

1148 PARK GREEN PLACE

Winter Park, FL

Courtesy of DON ASHER & ASSOCIATES, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 1826 PINEVIEW CIRCLE Winter Park, FL MLS# O6373874
  • Recently Listed with Virtual Tour
1 of 14
$2,495
3

Beds

2.0

Baths

1,222

Sq.Ft.

1826 PINEVIEW CIRCLE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1622 ARBOR PARK DRIVE Winter Park, FL MLS# O6350734
$2,500
3

Beds

1.1

Baths

1,351

Sq.Ft.

1622 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of BEST ORLANDO PROPERTY MANAGEMENT LLC
View 1041 ARAGON AVENUE Winter Park, FL MLS# TB8453961
$2,500
2

Beds

2.1

Baths

1,641

Sq.Ft.

1041 ARAGON AVENUE

Winter Park, FL

Courtesy of BANNER INT'L REAL ESTATE
View Address not provided Winter Park, FL MLS# O6379158
  • Recently Listed
1 of 2
$2,500
Studio

Beds

0.0

Baths

Address not provided

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 950 HEDGEWOOD COURT Winter Park, FL MLS# O6370344
  • Virtual Tour
1 of 32
$2,650
4

Beds

2.0

Baths

1,714

Sq.Ft.

950 HEDGEWOOD COURT

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View Address not provided Winter Park, FL MLS# O6375024
$2,650
2

Beds

1.0

Baths

1,000

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of LOMBARDI LEMAY REALTY
View 2352 SMILEY AVENUE Winter Park, FL MLS# O6372791
  • Virtual Tour
1 of 15
$2,700
3

Beds

2.0

Baths

1,456

Sq.Ft.

2352 SMILEY AVENUE

Winter Park, FL

Courtesy of FLORIDA PRESTIGIOUS HOMES INC
View 1055 CHEROKEE AVENUE Winter Park, FL MLS# O6360540
  • Virtual Tour
1 of 45
$2,800
3

Beds

2.0

Baths

1,560

Sq.Ft.

1055 CHEROKEE AVENUE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 3642 PERIWINKLE DRIVE Winter Park, FL MLS# O6362737
$2,800
5

Beds

3.0

Baths

1,945

Sq.Ft.

3642 PERIWINKLE DRIVE

Winter Park, FL

Courtesy of HONEST REAL ESTATE COMPANY
View 1315 WESTCHESTER AVENUE Winter Park, FL MLS# O6370403
$2,800
2

Beds

2.0

Baths

980

Sq.Ft.

1315 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, LLC
View 2862 KINGS DEER ROAD Winter Park, FL MLS# O6361314
  • Virtual Tour
1 of 34
$2,850
3

Beds

2.0

Baths

1,763

Sq.Ft.

2862 KINGS DEER ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2992 CHANTILLY AVENUE Winter Park, FL MLS# O6375763
  • Recently Listed with Virtual Tour
1 of 39
$2,880
3

Beds

2.0

Baths

1,496

Sq.Ft.

2992 CHANTILLY AVENUE

Winter Park, FL

Courtesy of LEMUEL PROPERTY MANAGEMENT LLC
View 2128 SYCAMORE DRIVE Winter Park, FL MLS# L4955520
  • Virtual Tour
1 of 57
$2,900
3

Beds

2.0

Baths

1,760

Sq.Ft.

2128 SYCAMORE DRIVE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1891 OGLESBY AVENUE Winter Park, FL MLS# O6362840
  • Virtual Tour
1 of 15
$3,000
3

Beds

2.0

Baths

1,195

Sq.Ft.

1891 OGLESBY AVENUE

Winter Park, FL

Courtesy of URBANISTA BROKERS
View 1835 EDWIN BOULEVARD Winter Park, FL MLS# O6372293
  • Virtual Tour
1 of 50
$3,150
3

Beds

2.0

Baths

1,436

Sq.Ft.

1835 EDWIN BOULEVARD

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1807 N PARK AVENUE Winter Park, FL MLS# O6359356
  • Virtual Tour
1 of 42
$3,295
3

Beds

2.0

Baths

1,747

Sq.Ft.

1807 N PARK AVENUE

Winter Park, FL

Courtesy of THE REALTY MEDICS
View 690 OSCEOLA AVENUE 203 Winter Park, FL MLS# O6357444
$3,400
2

Beds

2.0

Baths

1,148

Sq.Ft.

690 OSCEOLA AVENUE 203

Winter Park, FL

Courtesy of ANNE ROGERS 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

298

Estimated median home price

$687,500
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 7
$100K - 200K 34
$200K - 300K 29
$300K - 400K 15
$400K - 500K 26
$500K - 600K 18
$600K - 700K 25
$700K - 800K 18
$800K - 900K 5
$900K - 1M 8
$1M - Max 113

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 167
Townhouse 17
Condo 80
Commercial 6
Rental 87
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 2/3/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 2/3/2026.