99 total properties
Did you mean the neighborhood Winter Park?
View 900 S KENTUCKY AVENUE Winter Park, FL MLS# O6374630
  • Recently Listed with Virtual Tour
1 of 15
$3,500
3

Beds

2.0

Baths

1,508

Sq.Ft.

900 S KENTUCKY AVENUE

Winter Park, FL

Courtesy of FLORIDA PRESTIGIOUS HOMES INC
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 3651 N GOLDENROD ROAD E103 Winter Park, FL MLS# O6373934
  • Recently Listed with Virtual Tour
1 of 7
$1,325
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD E103

Winter Park, FL

Courtesy of AMERICAN REALTY EXPERTS
The time to sell is now! THE TIME TO SELL IS NOW!
View 3651 N GOLDENROD ROAD C205 Winter Park, FL MLS# O6373015
  • Recently Listed with Virtual Tour
1 of 11
$1,495
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD C205

Winter Park, FL

Courtesy of CFRP REALTY LLC
View 1049 N KENTUCKY AVENUE Winter Park, FL MLS# O6373029
  • Recently Listed with Virtual Tour
1 of 43
$6,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

1049 N KENTUCKY AVENUE

Winter Park, FL

Courtesy of THE AGENCY ORLANDO
View 840 W CANTON AVENUE Winter Park, FL MLS# O6372874
  • Recently Listed with Virtual Tour
1 of 17
$4,000
2

Beds

2.0

Baths

1,400

Sq.Ft.

840 W CANTON AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1835 EDWIN BOULEVARD Winter Park, FL MLS# O6372293
  • Recently Listed with Virtual Tour
1 of 50
$3,175
3

Beds

2.0

Baths

1,436

Sq.Ft.

1835 EDWIN BOULEVARD

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 438 W SWOOPE AVENUE Winter Park, FL MLS# O6368619
  • Recently Listed with Virtual Tour
1 of 27
$4,795
3

Beds

2.1

Baths

2,317

Sq.Ft.

438 W SWOOPE AVENUE

Winter Park, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 2352 SMILEY AVENUE Winter Park, FL MLS# O6372791
  • Recently Listed with 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 Address not provided Winter Park, FL MLS# A11941557
  • Recently Listed with Virtual Tour
1 of 20
$1,950
3

Beds

2.0

Baths

1,350

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of SYNERGY INTERNATIONAL REALTY, INC.
View 200 SAINT ANDREWS BOULEVARD 1805 Winter Park, FL MLS# O6372204
  • Recently Listed with Virtual Tour
1 of 13
$2,000
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 1805

Winter Park, FL

Courtesy of LIVE MVRK LLC
View 2913 ABBEY COURT Winter Park, FL MLS# O6372091
  • Virtual Tour
1 of 32
$2,900
4

Beds

2.0

Baths

1,776

Sq.Ft.

2913 ABBEY COURT

Winter Park, FL

Courtesy of MAINFRAME REAL ESTATE
View 151 N ORLANDO AVENUE 203 Winter Park, FL MLS# O6371650
  • Recently Listed with Virtual Tour
1 of 20
$2,200
2

Beds

1.0

Baths

800

Sq.Ft.

151 N ORLANDO AVENUE 203

Winter Park, FL

Courtesy of SAND DOLLAR REALTY GROUP INC
View 1802 MONDRIAN CIRCLE Winter Park, FL MLS# O6370892
  • Recently Listed with Virtual Tour
1 of 29
$4,700
3

Beds

3.1

Baths

2,193

Sq.Ft.

1802 MONDRIAN CIRCLE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1302 MICHIGAN AVENUE Winter Park, FL MLS# O6371456
  • Recently Listed with Virtual Tour
1 of 17
$3,950
3

Beds

2.1

Baths

1,880

Sq.Ft.

1302 MICHIGAN AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 200 SAINT ANDREWS BOULEVARD 1803 Winter Park, FL MLS# O6371317
  • Recently Listed with Virtual Tour
1 of 32
$1,695
2

Beds

1.1

Baths

1,219

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 1803

Winter Park, FL

Courtesy of WILSON MANAGEMENT GROUP
View 3651 N GOLDENROD ROAD E205 Winter Park, FL MLS# O6371647
  • Recently Listed with Virtual Tour
1 of 16
$1,300
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD E205

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3212 NETHERWOOD DRIVE Winter Park, FL MLS# O6370689
  • Recently Listed
1 of 6
$1,500
1

Beds

1.0

Baths

400

Sq.Ft.

3212 NETHERWOOD DRIVE

Winter Park, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 950 HEDGEWOOD COURT Winter Park, FL MLS# O6370344
  • Recently Listed
1 of 3
$2,650
4

Beds

2.0

Baths

1,714

Sq.Ft.

950 HEDGEWOOD COURT

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 1116 FAIRWAY DRIVE Winter Park, FL MLS# O6371242
  • Recently Listed with Virtual Tour
1 of 38
$3,100
3

Beds

2.0

Baths

1,738

Sq.Ft.

1116 FAIRWAY DRIVE

Winter Park, FL

Courtesy of TURN-KEY MOVES REALTY

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

280

Estimated median home price

$670,000
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 6
$100K - 200K 34
$200K - 300K 25
$300K - 400K 15
$400K - 500K 25
$500K - 600K 17
$600K - 700K 26
$700K - 800K 19
$800K - 900K 4
$900K - 1M 10
$1M - Max 99

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 157
Townhouse 20
Condo 73
Commercial 6
Rental 101
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/16/2026)

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 1/17/2026.