56 total properties
Did you mean the neighborhood Winter Park?
View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
  • Recently Listed
1 of 37
$675,000
4

Beds

2.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
  • Recently Listed
1 of 2
$599,999
Studio

Beds

0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 300 CAROLINA AVENUE 402C Winter Park, FL MLS# O6410016
  • Recently Listed with Virtual Tour
1 of 34
$750,000
3

Beds

2.0

Baths

1,350

Sq.Ft.

300 CAROLINA AVENUE 402C

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 1009 LAKE BELL DRIVE Winter Park, FL MLS# O6409849
  • Recently Listed
1 of 20
$699,000
3

Beds

2.0

Baths

1,467

Sq.Ft.

1009 LAKE BELL DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1009 LAKE BELL DRIVE Winter Park, FL MLS# O6410167
  • Recently Listed
1 of 16
$699,000
Studio

Beds

0.0

Baths

1009 LAKE BELL DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 7740 LAKE DAWN DR Winter Park, FL MLS# O6410689
  • Recently Listed with Virtual Tour
1 of 68
$729,000
5

Beds

3.0

Baths

2,495

Sq.Ft.

7740 LAKE DAWN DR

Winter Park, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 1707 HARMON AVENUE Winter Park, FL MLS# O6409180
  • Recently Listed with Virtual Tour
1 of 37
$695,000
3

Beds

2.0

Baths

1,669

Sq.Ft.

1707 HARMON AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2333 WESTMINSTER COURT Winter Park, FL MLS# O6407054
  • Recently Listed with Virtual Tour
1 of 48
$719,000
4

Beds

2.0

Baths

1,877

Sq.Ft.

2333 WESTMINSTER COURT

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 962 ARAGON AVENUE Winter Park, FL MLS# O6407916
  • Virtual Tour
1 of 34
$599,900
3

Beds

2.0

Baths

1,680

Sq.Ft.

962 ARAGON AVENUE

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
View 1780 GOODRICH AVENUE Winter Park, FL MLS# O6403811
  • Virtual Tour
1 of 41
$625,000
3

Beds

2.0

Baths

1,283

Sq.Ft.

1780 GOODRICH AVENUE

Winter Park, FL

Courtesy of SUMMERPARK HOMES REALTY LLC
View 2940 DE BROCY WAY Winter Park, FL MLS# O6408085
  • Virtual Tour
1 of 55
$785,000
3

Beds

2.0

Baths

2,679

Sq.Ft.

2940 DE BROCY WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 505 CORNWALL ROAD Winter Park, FL MLS# O6408759
  • Recently Listed with Virtual Tour
1 of 42
$675,000
4

Beds

2.0

Baths

1,813

Sq.Ft.

505 CORNWALL ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6407540
  • Recently Listed
1 of 39
$719,000
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of ADAIR REALTY INC
View 616 FITZWALTER DRIVE Winter Park, FL MLS# O6403982
  • Recently Listed
1 of 30
$595,000
3

Beds

2.0

Baths

1,396

Sq.Ft.

616 FITZWALTER DRIVE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 408 HOLT AVENUE Winter Park, FL MLS# O6405857
  • Recently Listed with Virtual Tour
1 of 34
$745,000
2

Beds

3.0

Baths

1,440

Sq.Ft.

408 HOLT AVENUE

Winter Park, FL

Courtesy of THE REAL ESTATE PRINCIPLE, INC
View 1550 NORFOLK AVENUE Winter Park, FL MLS# O6402927
  • Virtual Tour
1 of 29
$725,000
3

Beds

2.0

Baths

1,762

Sq.Ft.

1550 NORFOLK AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 688 BRECHIN DRIVE Winter Park, FL MLS# O6403080
  • Virtual Tour
1 of 31
$724,900
4

Beds

2.0

Baths

1,599

Sq.Ft.

688 BRECHIN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1437 MILLER AVENUE Winter Park, FL MLS# O6403858
$750,000
5

Beds

4.0

Baths

2,150

Sq.Ft.

1437 MILLER AVENUE

Winter Park, FL

Courtesy of ORLANDO REAL ESTATE LLC
View 2324 LEE ROAD Winter Park, FL MLS# O6403791
  • Virtual Tour
1 of 36
$750,000
2,124

Sq.Ft.

2324 LEE ROAD

Winter Park, FL

Courtesy of CARLISLE REALTY, LLC
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

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

391

Estimated median home price

$785,000
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 2
$100K - 200K 47
$200K - 300K 24
$300K - 400K 24
$400K - 500K 29
$500K - 600K 23
$600K - 700K 29
$700K - 800K 20
$800K - 900K 15
$900K - 1M 10
$1M - Max 168

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 249
Townhouse 15
Condo 86
Commercial 7
Rental 77
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/27/2026)

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 5/27/2026.

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 5/27/2026.