108 total properties
Did you mean the neighborhood Winter Park?
View 2221 HAWICK LANE Winter Park, FL MLS# O6364916
  • Virtual Tour
1 of 22
$2,500
3

Beds

2.0

Baths

1,727

Sq.Ft.

2221 HAWICK LANE

Winter Park, FL

Courtesy of JC FLORIDA REALTY LLC
View 1945 GUNN ROAD Winter Park, FL MLS# O6369450
  • Recently Listed with Virtual Tour
1 of 35
$3,499
3

Beds

2.0

Baths

1,800

Sq.Ft.

1945 GUNN ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 3651 N GOLDENROD ROAD 106 Winter Park, FL MLS# O6369311
  • Recently Listed with Virtual Tour
1 of 18
$1,550
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD 106

Winter Park, FL

Courtesy of INNOVATIVE REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 3011 GEORGE MASON AVENUE 3 Winter Park, FL MLS# O6368606
  • Recently Listed with Virtual Tour
1 of 15
$1,395
2

Beds

2.0

Baths

1,056

Sq.Ft.

3011 GEORGE MASON AVENUE 3

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1250 S DENNING DRIVE 208 Winter Park, FL MLS# O6368688
  • Recently Listed with Virtual Tour
1 of 7
$1,475
1

Beds

1.0

Baths

653

Sq.Ft.

1250 S DENNING DRIVE 208

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 216 RIPPLING LANE Winter Park, FL MLS# O6368316
  • Recently Listed with Virtual Tour
1 of 21
$2,700
3

Beds

2.0

Baths

1,848

Sq.Ft.

216 RIPPLING LANE

Winter Park, FL

Courtesy of SAFETYNET REALTY
View 3117 RAIDERS RUN Winter Park, FL MLS# O6368350
  • Recently Listed with Virtual Tour
1 of 16
$2,665
5

Beds

3.0

Baths

2,047

Sq.Ft.

3117 RAIDERS RUN

Winter Park, FL

Courtesy of RISE 24 REAL ESTATE LLC
View 3045 AARON BURR AVENUE 10 Winter Park, FL MLS# S5140420
  • Recently Listed with Virtual Tour
1 of 25
$1,350
1

Beds

1.0

Baths

803

Sq.Ft.

3045 AARON BURR AVENUE 10

Winter Park, FL

Courtesy of TBO REAL ESTATE PARTNERS INC
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6368525
  • Recently Listed with Virtual Tour
1 of 12
$1,700
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 2918 ANTIQUE OAKS CIR APT 31 Winter Park, FL MLS# O6368157
  • Recently Listed with Virtual Tour
1 of 23
$2,200
2

Beds

2.0

Baths

1,018

Sq.Ft.

2918 ANTIQUE OAKS CIR APT 31

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View Address not provided Winter Park, FL MLS# O6367750
  • Recently Listed with Virtual Tour
1 of 24
$1,800
3

Beds

2.0

Baths

1,149

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of ZEN LIVING HOMES LLC
View 275 N CAPEN AVENUE Winter Park, FL MLS# O6367606
  • Recently Listed
1 of 15
$1,975
4

Beds

2.0

Baths

1,180

Sq.Ft.

275 N CAPEN AVENUE

Winter Park, FL

Courtesy of PREMIER MANAGEMENT GROUP INC
View 3651 N GOLDENROD ROAD C204 Winter Park, FL MLS# O6367623
  • Recently Listed with Virtual Tour
1 of 14
$1,495
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD C204

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 2220 VIA TUSCANY Winter Park, FL MLS# O6367319
  • Recently Listed with Virtual Tour
1 of 48
$10,950
4

Beds

3.0

Baths

2,918

Sq.Ft.

2220 VIA TUSCANY

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 101 S INTERLACHEN AVENUE 104 Winter Park, FL MLS# O6367159
$3,800
2

Beds

2.0

Baths

949

Sq.Ft.

101 S INTERLACHEN AVENUE 104

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1891 OGLESBY AVENUE Winter Park, FL MLS# O6362840
  • Recently Listed with 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 654 TRINIDAD CT 654 Winter Park, FL MLS# S5140107
  • Recently Listed with Virtual Tour
1 of 7
$1,800
2

Beds

2.0

Baths

1,120

Sq.Ft.

654 TRINIDAD CT 654

Winter Park, FL

Courtesy of LA ROSA REALTY KISSIMMEE
View 220 OVERLOOK ROAD Winter Park, FL MLS# O6365244
  • Virtual Tour
1 of 20
$3,600
2

Beds

2.0

Baths

1,393

Sq.Ft.

220 OVERLOOK ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 519 PARK NORTH COURT Winter Park, FL MLS# O6365855
$7,000
4

Beds

3.2

Baths

3,302

Sq.Ft.

519 PARK NORTH COURT

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1221 RICHMOND ROAD Winter Park, FL MLS# O6365952
$19,000
5

Beds

5.1

Baths

5,164

Sq.Ft.

1221 RICHMOND ROAD

Winter Park, FL

Courtesy of LA ROSA REALTY LLC

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

289

Estimated median home price

$665,000
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 39
$200K - 300K 21
$300K - 400K 17
$400K - 500K 26
$500K - 600K 22
$600K - 700K 21
$700K - 800K 21
$800K - 900K 4
$900K - 1M 11
$1M - Max 101

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 166
Townhouse 20
Condo 74
Commercial 5
Rental 108
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/1/2026)

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 1/1/2026.