52 total properties
Did you mean the neighborhood Winter Park?
View 860 N DENNING DRIVE Winter Park, FL MLS# O6412589
  • Virtual Tour
1 of 52
$699,900
3

Beds

2.1

Baths

1,411

Sq.Ft.

860 N DENNING DRIVE

Winter Park, FL

View 2157 LAKE DRIVE Winter Park, FL MLS# O6412258
  • Virtual Tour
1 of 45
$689,000
3

Beds

3.0

Baths

2,124

Sq.Ft.

2157 LAKE DRIVE

Winter Park, FL

View 840 W CANTON AVENUE Winter Park, FL MLS# O6412754
$649,900
3

Beds

2.0

Baths

1,370

Sq.Ft.

840 W CANTON AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
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1 of 37
$625,000
4

Beds

2.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

View 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
$599,999
Studio

Beds

0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
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1 of 32
$579,000
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

View 1009 LAKE BELL DRIVE Winter Park, FL MLS# O6409849
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1 of 41
$650,000
3

Beds

2.0

Baths

1,467

Sq.Ft.

1009 LAKE BELL DRIVE

Winter Park, FL

View 1009 LAKE BELL DRIVE Winter Park, FL MLS# O6410167
$650,000
Studio

Beds

0.0

Baths

1009 LAKE BELL DRIVE

Winter Park, FL

View 2418 EUSTON ROAD Winter Park, FL MLS# O6409323
  • Virtual Tour
1 of 34
$659,998
3

Beds

2.1

Baths

2,048

Sq.Ft.

2418 EUSTON ROAD

Winter Park, FL

Courtesy of TOLARIS REALTY GROUP LLC
View 715 S RANGER BOULEVARD Winter Park, FL MLS# O6410899
$695,000
4

Beds

3.0

Baths

2,312

Sq.Ft.

715 S RANGER BOULEVARD

Winter Park, FL

View 1707 HARMON AVENUE Winter Park, FL MLS# O6409180
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1 of 37
OPEN HOUSE: Sunday 7/26 2:00 PM - 4:00 PM
$639,000
3

Beds

2.0

Baths

1,669

Sq.Ft.

1707 HARMON AVENUE

Winter Park, FL

View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6407540
$695,000
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

View 1822 YORKSHIRE DRIVE Winter Park, FL MLS# O6401364
  • Virtual Tour
1 of 42
$598,000
3

Beds

3.0

Baths

1,620

Sq.Ft.

1822 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
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1 of 13
$589,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
$569,900
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1830 EDWIN BOULEVARD Winter Park, FL MLS# O6400055
  • Virtual Tour
1 of 48
$625,000
3

Beds

2.0

Baths

1,287

Sq.Ft.

1830 EDWIN BOULEVARD

Winter Park, FL

View 2600 EUSTON ROAD Winter Park, FL MLS# O6397890
  • Virtual Tour
1 of 36
$630,000
6

Beds

3.0

Baths

3,145

Sq.Ft.

2600 EUSTON ROAD

Winter Park, FL

View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
  • Virtual Tour
1 of 39
$574,900
3

Beds

2.0

Baths

1,269

Sq.Ft.

1354 INDIANA AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
  • Virtual Tour
1 of 47
$614,500
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

View 4033 YACHT COURT Winter Park, FL MLS# O6379135
  • Virtual Tour
1 of 26
$549,000
3

Beds

2.0

Baths

2,268

Sq.Ft.

4033 YACHT COURT

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY

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

375

Estimated median home price

$759,000
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 8
$100K - 200K 43
$200K - 300K 24
$300K - 400K 18
$400K - 500K 31
$500K - 600K 24
$600K - 700K 31
$700K - 800K 15
$800K - 900K 14
$900K - 1M 10
$1M - Max 157

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 229
Townhouse 19
Condo 83
Commercial 11
Rental 66
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 7/25/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

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 7/25/2026.

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 7/25/2026.