33 total properties
Did you mean the neighborhood Winter Park?
View 350 CORNWALL RD Winter Park, FL MLS# O6394524
  • Recently Listed with Virtual Tour
1 of 35
$775,000
4

Beds

3.0

Baths

2,038

Sq.Ft.

350 CORNWALL RD

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 418 GILBERT ROAD Winter Park, FL MLS# O6385950
  • Recently Listed
1 of 30
$740,000
3

Beds

3.0

Baths

1,680

Sq.Ft.

418 GILBERT ROAD

Winter Park, FL

Courtesy of SOTERA LIVING
View 668 OVERSPIN DRIVE Winter Park, FL MLS# O6392301
  • Recently Listed with Virtual Tour
1 of 33
$875,000
4

Beds

3.0

Baths

2,509

Sq.Ft.

668 OVERSPIN DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2919 BOWER ROAD Winter Park, FL MLS# O6391025
  • Recently Listed with Virtual Tour
1 of 38
$779,000
3

Beds

2.0

Baths

2,325

Sq.Ft.

2919 BOWER ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2119 HOWARD DRIVE Winter Park, FL MLS# O6390345
  • Virtual Tour
1 of 21
$850,000
4

Beds

2.0

Baths

2,479

Sq.Ft.

2119 HOWARD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1034 TURNER ROAD Winter Park, FL MLS# O6390132
  • Recently Listed
1 of 5
$724,900
Studio

Beds

0.0

Baths

1034 TURNER ROAD

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
View 325 N PHELPS AVENUE Winter Park, FL MLS# O6388118
  • Virtual Tour
1 of 6
$795,000
Studio

Beds

0.0

Baths

325 N PHELPS AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 628 DUNBLANE DRIVE Winter Park, FL MLS# O6387091
  • Virtual Tour
1 of 54
$849,000
3

Beds

2.1

Baths

2,114

Sq.Ft.

628 DUNBLANE DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2625 SUMMERFIELD ROAD Winter Park, FL MLS# O6384757
$724,900
5

Beds

3.0

Baths

2,199

Sq.Ft.

2625 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1108 FAIRWAY DRIVE Winter Park, FL MLS# O6386266
  • Virtual Tour
1 of 46
$725,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

1108 FAIRWAY DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 643 DUNBLANE DRIVE Winter Park, FL MLS# O6386136
  • Virtual Tour
1 of 62
$699,800
3

Beds

2.0

Baths

1,575

Sq.Ft.

643 DUNBLANE DRIVE

Winter Park, FL

Courtesy of ZEN LIVING HOMES LLC
View 1680 PALMER AVENUE Winter Park, FL MLS# O6375108
$825,000
3

Beds

2.0

Baths

1,893

Sq.Ft.

1680 PALMER AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1927 ELAND AVENUE Winter Park, FL MLS# O6381009
  • Virtual Tour
1 of 68
$850,000
5

Beds

3.0

Baths

2,242

Sq.Ft.

1927 ELAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 675 OVERSPIN DRIVE Winter Park, FL MLS# O6378975
  • Virtual Tour
1 of 32
$775,000
4

Beds

3.1

Baths

3,062

Sq.Ft.

675 OVERSPIN DRIVE

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
View 841 W SWOOPE AVENUE Winter Park, FL MLS# O6373287
$740,000
2

Beds

1.0

Baths

1,396

Sq.Ft.

841 W SWOOPE AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 432 W SWOOPE AVENUE Winter Park, FL MLS# O6375719
  • Virtual Tour
1 of 20
$695,000
4

Beds

3.1

Baths

2,317

Sq.Ft.

432 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1780 BRYAN AVENUE Winter Park, FL MLS# O6365369
  • Virtual Tour
1 of 8
$849,000
4

Beds

2.0

Baths

1,617

Sq.Ft.

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 676 DUNBLANE DRIVE Winter Park, FL MLS# O6365557
  • Virtual Tour
1 of 35
$750,000
3

Beds

2.0

Baths

1,827

Sq.Ft.

676 DUNBLANE DRIVE

Winter Park, FL

Courtesy of BALDWIN PARK REALTY LLC
View 1929 S LAKEMONT AVENUE Winter Park, FL MLS# O6364557
$915,000
3

Beds

3.1

Baths

2,160

Sq.Ft.

1929 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 763 Overspin Drive Winter Park, FL MLS# 256173
$699,000
Studio

Beds

0.0

Baths

763 Overspin Drive

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

331

Estimated median home price

$750,000
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 4
$100K - 200K 46
$200K - 300K 23
$300K - 400K 14
$400K - 500K 30
$500K - 600K 15
$600K - 700K 23
$700K - 800K 16
$800K - 900K 9
$900K - 1M 9
$1M - Max 142

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 197
Townhouse 17
Condo 85
Commercial 3
Rental 81
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 3/27/2026)

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 3/30/2026.

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 3/30/2026.