44 total properties
Did you mean the neighborhood Winter Park?
View 410 SAINT DUNSTAN WAY Winter Park, FL MLS# O6416796
$500,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

410 SAINT DUNSTAN WAY

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1521 CAVENDISH RD Winter Park, FL MLS# O6415985
$470,000
2

Beds

1.0

Baths

1,036

Sq.Ft.

1521 CAVENDISH RD

Winter Park, FL

View 650 DOUGLAS AVENUE Winter Park, FL MLS# O6414807
$550,000
3

Beds

2.0

Baths

1,280

Sq.Ft.

650 DOUGLAS AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2715 PRINCE JOHN ROAD Winter Park, FL MLS# O6415084
  • Recently Listed with Virtual Tour
1 of 29
$504,900
3

Beds

2.0

Baths

1,565

Sq.Ft.

2715 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of VIA PROPERTIES LLC
View 2974 CHANTILLY AVENUE Winter Park, FL MLS# O6412851
  • Recently Listed with Virtual Tour
1 of 26
$499,000
3

Beds

2.0

Baths

1,433

Sq.Ft.

2974 CHANTILLY AVENUE

Winter Park, FL

View 528 SAINT DUNSTAN WAY Winter Park, FL MLS# O6414677
  • Recently Listed with Virtual Tour
1 of 35
$535,000
3

Beds

2.0

Baths

1,656

Sq.Ft.

528 SAINT DUNSTAN WAY

Winter Park, FL

View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Saturday 6/27 1:00 PM - 4:00 PM
$560,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 641 W LYMAN AVENUE Winter Park, FL MLS# O6408078
$509,000
3

Beds

2.0

Baths

1,120

Sq.Ft.

641 W LYMAN AVENUE

Winter Park, FL

View 1944 NATALEN ROAD Winter Park, FL MLS# O6405802
$519,000
3

Beds

2.0

Baths

1,380

Sq.Ft.

1944 NATALEN ROAD

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 2803 BANCHORY ROAD Winter Park, FL MLS# O6404011
$495,000
4

Beds

2.0

Baths

1,596

Sq.Ft.

2803 BANCHORY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1871 BRYAN AVENUE Winter Park, FL MLS# O6410779
$499,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

1871 BRYAN AVENUE

Winter Park, FL

View 316 BECKETT COURT Winter Park, FL MLS# O6411108
$450,000
4

Beds

2.0

Baths

1,651

Sq.Ft.

316 BECKETT COURT

Winter Park, FL

Courtesy of ITS REALTY
View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
$579,000
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

View 2718 SANDWELL DRIVE Winter Park, FL MLS# O6410283
$525,000
3

Beds

2.0

Baths

1,597

Sq.Ft.

2718 SANDWELL DRIVE

Winter Park, FL

View 731 BONGART ROAD Winter Park, FL MLS# O6406004
$499,000
4

Beds

3.0

Baths

1,526

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
$545,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
$515,000
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

Courtesy of CAISSA REALTY INVESTMENT INC
View 1745 INDIANA AVENUE J Winter Park, FL MLS# O6402920
$524,000
3

Beds

2.1

Baths

1,616

Sq.Ft.

1745 INDIANA AVENUE J

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2829 ALOMA Winter Park, FL MLS# O6404107
  • Virtual Tour
1 of 36
$579,000
4

Beds

2.0

Baths

1,821

Sq.Ft.

2829 ALOMA

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
$534,900
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

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

397

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 - 100K2
$100K - 200K41
$200K - 300K24
$300K - 400K22
$400K - 500K29
$500K - 600K31
$600K - 700K28
$700K - 800K20
$800K - 900K14
$900K - 1M9
$1M - Max177

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family262
Townhouse16
Condo84
Commercial7
Rental73
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 6/22/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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

Data is updated as of 6/22/2026.

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 6/22/2026.