100 total properties
Did you mean the neighborhood Winter Park?
View 2142 BLOSSOM LANE Winter Park, FL MLS# O6409144
$399,900
3

Beds

2.0

Baths

1,363

Sq.Ft.

2142 BLOSSOM LANE

Winter Park, FL

View 1500 GAY ROAD 17D Winter Park, FL MLS# O6408516
$259,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 17D

Winter Park, FL

View 2973 SANBINA STREET Winter Park, FL MLS# O6407521
$377,880
3

Beds

2.0

Baths

1,128

Sq.Ft.

2973 SANBINA STREET

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
$399,000
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
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OPEN HOUSE: Saturday 6/20 1:00 PM - 4:00 PM
$379,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

340 KILLARNEY BAY COURT 4-4

Winter Park, FL

View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
$410,000
3

Beds

2.0

Baths

1,402

Sq.Ft.

7532 AZUREBROOK COURT

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2482 ROXBURY ROAD Winter Park, FL MLS# O6406443
$375,000
2

Beds

1.0

Baths

913

Sq.Ft.

2482 ROXBURY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 2500 LEE ROAD 232 Winter Park, FL MLS# O6404916
$164,900
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 232

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 721 DUNBAR STREET Winter Park, FL MLS# O6405338
$399,999
2

Beds

2.0

Baths

1,018

Sq.Ft.

721 DUNBAR STREET

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1695 LEE ROAD E116 Winter Park, FL MLS# O6399346
$110,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E116

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 4772 TANGERINE AVENUE 4772 Winter Park, FL MLS# O6405042
$199,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4772 TANGERINE AVENUE 4772

Winter Park, FL

View 7327 FOREST HILL COURT 223 Winter Park, FL MLS# O6403841
$180,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7327 FOREST HILL COURT 223

Winter Park, FL

Courtesy of M L VAZ REALTY INC
View 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
$250,000
3

Beds

2.1

Baths

1,578

Sq.Ft.

7484 CANFORD COURT 8

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 639 SAINT JOHNS COURT 639 Winter Park, FL MLS# O6402025
$194,900
2

Beds

2.0

Baths

1,120

Sq.Ft.

639 SAINT JOHNS COURT 639

Winter Park, FL

View 2889 ROUEN AVENUE Winter Park, FL MLS# L4961275
$375,000
3

Beds

2.0

Baths

1,144

Sq.Ft.

2889 ROUEN AVENUE

Winter Park, FL

View 3651 N GOLDENROD ROAD D102 Winter Park, FL MLS# O6401114
$157,900
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D102

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1307 FORMOSA AVENUE Winter Park, FL MLS# O6400711
$373,800
2

Beds

1.0

Baths

1,150

Sq.Ft.

1307 FORMOSA AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 814 DENSMORE DR Winter Park, FL MLS# O6399773
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$425,000
4

Beds

2.0

Baths

1,610

Sq.Ft.

814 DENSMORE DR

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES

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

399

Estimated median home price

$799,000
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 - 200K43
$200K - 300K24
$300K - 400K23
$400K - 500K29
$500K - 600K31
$600K - 700K30
$700K - 800K19
$800K - 900K14
$900K - 1M9
$1M - Max175

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family262
Townhouse15
Condo86
Commercial7
Rental71
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 6/19/2026)

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 6/20/2026.