75 total properties
Did you mean the neighborhood Winter Park?
View 887 EASTBROOK BOULEVARD Winter Park, FL MLS# O6420055
$2,250
4

Beds

2.0

Baths

1,701

Sq.Ft.

887 EASTBROOK BOULEVARD

Winter Park, FL

View 2028 ALBERT LEE PARKWAY Winter Park, FL MLS# O6432598
$2,250
3

Beds

1.1

Baths

1,514

Sq.Ft.

2028 ALBERT LEE PARKWAY

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 1450 CAVENDISH ROAD Winter Park, FL MLS# O6433199
$2,200
2

Beds

1.0

Baths

1,027

Sq.Ft.

1450 CAVENDISH ROAD

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 151 N ORLANDO AVENUE 207 Winter Park, FL MLS# O6425110
$2,150
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 207

Winter Park, FL

View 151 N ORLANDO AVENUE 203 Winter Park, FL MLS# O6424654
$2,100
2

Beds

1.0

Baths

800

Sq.Ft.

151 N ORLANDO AVENUE 203

Winter Park, FL

View 1618 INDIANA AVENUE 1616 Winter Park, FL MLS# O6434163
  • Recently Listed with Virtual Tour
1 of 14
$1,995
2

Beds

1.0

Baths

802

Sq.Ft.

1618 INDIANA AVENUE 1616

Winter Park, FL

View 937 ARAGON AVE Winter Park, FL MLS# O6436654
  • Recently Listed with Virtual Tour
1 of 23
$1,995
2

Beds

1.1

Baths

988

Sq.Ft.

937 ARAGON AVE

Winter Park, FL

View 1618 INDIANA AVENUE Winter Park, FL MLS# O6434146
  • Recently Listed with Virtual Tour
1 of 14
$1,989
2

Beds

1.0

Baths

1,604

Sq.Ft.

1618 INDIANA AVENUE

Winter Park, FL

View 151 N ORLANDO AVENUE 118 Winter Park, FL MLS# O6386414
$1,900
2

Beds

1.0

Baths

1,500

Sq.Ft.

151 N ORLANDO AVENUE 118

Winter Park, FL

View 3220 OAK LAWN PLACE PLACE 210 Winter Park, FL MLS# S5150258
$1,900
3

Beds

2.1

Baths

1,151

Sq.Ft.

3220 OAK LAWN PLACE PLACE 210

Winter Park, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 1500 GAY ROAD 25B Winter Park, FL MLS# O6434320
  • Recently Listed with Virtual Tour
1 of 22
$1,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 25B

Winter Park, FL

View 7446 WYNNEWOOD SQUARE 190 Winter Park, FL MLS# R4911800
$1,850
2

Beds

2.1

Baths

1,031

Sq.Ft.

7446 WYNNEWOOD SQUARE 190

Winter Park, FL

View 1695 LEE ROAD E215 Winter Park, FL MLS# O6434749
  • Recently Listed with Virtual Tour
1 of 82
$1,850
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E215

Winter Park, FL

View 1720 MILLER AVENUE Winter Park, FL MLS# O6435312
  • Recently Listed with Virtual Tour
1 of 20
$1,775
2

Beds

1.0

Baths

800

Sq.Ft.

1720 MILLER AVENUE

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6423856
$1,750
1

Beds

1.0

Baths

650

Sq.Ft.

Address not provided

Winter Park, FL

View 612 TRINIDAD COURT 612 Winter Park, FL MLS# O6429437
$1,750
2

Beds

2.0

Baths

1,037

Sq.Ft.

612 TRINIDAD COURT 612

Winter Park, FL

View 1812 KILLARNEY DRIVE Winter Park, FL MLS# O6433858
$1,750
2

Beds

1.0

Baths

1,048

Sq.Ft.

1812 KILLARNEY DRIVE

Winter Park, FL

Courtesy of EATON REALTY SERVICES
View 652 SAINT JOHNS COURT 652 Winter Park, FL MLS# O6437920
  • Recently Listed with Virtual Tour
1 of 19
$1,750
2

Beds

2.0

Baths

1,037

Sq.Ft.

652 SAINT JOHNS COURT 652

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 4812 TANGERINE AVENUE 4812 Winter Park, FL MLS# O6420610
$1,700
2

Beds

2.0

Baths

1,058

Sq.Ft.

4812 TANGERINE AVENUE 4812

Winter Park, FL

View 7336 FOREST HILL COURT 240 Winter Park, FL MLS# O6438878
  • Recently Listed with Virtual Tour
1 of 10
$1,700
2

Beds

1.1

Baths

990

Sq.Ft.

7336 FOREST HILL COURT 240

Winter Park, FL

Courtesy of REALIZE INTERNATIONAL REALTY L

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

$725,000
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 - 200K38
$200K - 300K22
$300K - 400K15
$400K - 500K36
$500K - 600K26
$600K - 700K35
$700K - 800K11
$800K - 900K10
$900K - 1M10
$1M - Max149

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family216
Townhouse21
Condo76
Commercial9
Rental77
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 9/6/2026)

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 9/7/2026.