45 total properties
Did you mean the neighborhood Winter Park?
View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
  • Recently Listed with Virtual Tour
1 of 22
$415,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

Courtesy of JC FLORIDA REALTY LLC
View 340 KILLARNEY BAY COURT 4-4 Winter Park, FL MLS# O6407259
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Sunday 5/17 12:00 PM - 1:00 PM
$410,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

340 KILLARNEY BAY COURT 4-4

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
  • Recently Listed with Virtual Tour
1 of 35
OPEN HOUSE: Sunday 5/17 1:00 PM - 4:00 PM
$410,000
3

Beds

2.0

Baths

1,402

Sq.Ft.

7532 AZUREBROOK COURT

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
  • Recently Listed with Virtual Tour
1 of 33
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
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 2237 WOODCREST DRIVE Winter Park, FL MLS# O6404115
$490,000
3

Beds

2.0

Baths

1,492

Sq.Ft.

2237 WOODCREST DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
  • Recently Listed with Virtual Tour
1 of 27
$550,000
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
  • Recently Listed
1 of 42
$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 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
$539,000
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1010 GARDEN DRIVE Winter Park, FL MLS# O6400287
$485,000
Studio

Beds

0.0

Baths

1010 GARDEN DRIVE

Winter Park, FL

Courtesy of WATSON REALTY CORP.
View 814 DENSMORE DR Winter Park, FL MLS# O6399773
  • Virtual Tour
1 of 24
$425,000
4

Beds

2.0

Baths

1,610

Sq.Ft.

814 DENSMORE DR

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 1210 FAIRWAY DR Winter Park, FL MLS# O6398533
$549,000
3

Beds

2.0

Baths

1,737

Sq.Ft.

1210 FAIRWAY DR

Winter Park, FL

Courtesy of CENTRAL FLORIDA PRIME REAL ESTATE LLC
View 3054 BLUEBROOK DRIVE Winter Park, FL MLS# O6398450
$410,000
3

Beds

2.0

Baths

1,939

Sq.Ft.

3054 BLUEBROOK DRIVE

Winter Park, FL

Courtesy of WEATHERSPOON REALTY INC
View 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
$470,000
3

Beds

2.0

Baths

1,606

Sq.Ft.

950 HANOVER AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
  • Virtual Tour
1 of 45
OPEN HOUSE: Sunday 5/17 1:00 PM - 4:00 PM
$459,000
3

Beds

2.0

Baths

1,491

Sq.Ft.

405 LAKE FAIR LANE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 512 N LAKEMONT AVENUE Winter Park, FL MLS# O6392353
$500,000
3

Beds

2.0

Baths

1,413

Sq.Ft.

512 N LAKEMONT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1807 HAMMERLIN AVENUE G Winter Park, FL MLS# O6391277
$550,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1807 HAMMERLIN AVENUE G

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 2779 SANBINA STREET Winter Park, FL MLS# O6388746
$439,000
3

Beds

2.0

Baths

1,405

Sq.Ft.

2779 SANBINA STREET

Winter Park, FL

Courtesy of MAINFRAME REAL ESTATE
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$484,990
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP 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

384

Estimated median home price

$792,500
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

PriceCount
$0 - 100K3
$100K - 200K50
$200K - 300K21
$300K - 400K21
$400K - 500K31
$500K - 600K23
$600K - 700K27
$700K - 800K18
$800K - 900K16
$900K - 1M8
$1M - Max166

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family239
Townhouse16
Condo87
Commercial7
Rental71
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 5/17/2026)

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 5/17/2026.

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 5/17/2026.