73 total properties
Did you mean the neighborhood Winter Park?
View 1760 ALABAMA DRIVE Winter Park, FL MLS# O6413560
  • Recently Listed
1 of 48
$9,500
4

Beds

2.1

Baths

2,841

Sq.Ft.

1760 ALABAMA DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 503 KILSHORE LANE Winter Park, FL MLS# O6412456
  • Recently Listed with Virtual Tour
1 of 13
$2,250
2

Beds

1.0

Baths

1,125

Sq.Ft.

503 KILSHORE LANE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 747 MARYLAND AVENUE Winter Park, FL MLS# O6412619
  • Recently Listed with Virtual Tour
1 of 29
$2,500
3

Beds

2.0

Baths

786

Sq.Ft.

747 MARYLAND AVENUE

Winter Park, FL

Courtesy of ALFANO PROPERTY MANAGEMENT
The time to sell is now! THE TIME TO SELL IS NOW!
View 652 SAINT JHONS 652 Winter Park, FL MLS# TB8514256
  • Recently Listed with Virtual Tour
1 of 33
$1,900
2

Beds

2.0

Baths

1,037

Sq.Ft.

652 SAINT JHONS 652

Winter Park, FL

Courtesy of HOME PRIME REALTY LLC
View 7420 WOODBURN COURT 25 Winter Park, FL MLS# O6412225
  • Recently Listed with Virtual Tour
1 of 16
$1,800
3

Beds

2.1

Baths

1,151

Sq.Ft.

7420 WOODBURN COURT 25

Winter Park, FL

Courtesy of U S GLORY REALTY
View 640 N PARK AVENUE 5 Winter Park, FL MLS# O6411306
  • Virtual Tour
1 of 23
$3,200
1

Beds

1.0

Baths

673

Sq.Ft.

640 N PARK AVENUE 5

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1119 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6411654
$4,250
4

Beds

3.0

Baths

3,000

Sq.Ft.

1119 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1415 HARMON AVENUE Winter Park, FL MLS# O6407290
  • Virtual Tour
1 of 36
$3,060
3

Beds

2.1

Baths

1,700

Sq.Ft.

1415 HARMON AVENUE

Winter Park, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 620 TRINIDAD COURT 620 Winter Park, FL MLS# S5150729
$1,725
2

Beds

2.0

Baths

1,120

Sq.Ft.

620 TRINIDAD COURT 620

Winter Park, FL

Courtesy of TRANSCEND REALTY
View 184 SANDLEWOOD TRAIL 2 Winter Park, FL MLS# O6411443
  • Recently Listed with Virtual Tour
1 of 30
$2,000
2

Beds

2.1

Baths

1,133

Sq.Ft.

184 SANDLEWOOD TRAIL 2

Winter Park, FL

View 7338 SWALLOW RUN 7338 Winter Park, FL MLS# O6411093
$1,650
2

Beds

2.0

Baths

774

Sq.Ft.

7338 SWALLOW RUN 7338

Winter Park, FL

Courtesy of DOUGLAS EDMUND REAL ESTATE LLC
View 2344 WOODCREST DRIVE Winter Park, FL MLS# O6410619
  • Virtual Tour
1 of 15
$4,100
4

Beds

2.0

Baths

1,764

Sq.Ft.

2344 WOODCREST DRIVE

Winter Park, FL

Courtesy of EXPLORE FLORIDA REALTY SERVICES LLC
View 1404 CLAY STREET Winter Park, FL MLS# O6410414
  • Virtual Tour
1 of 17
$2,800
3

Beds

2.0

Baths

1,440

Sq.Ft.

1404 CLAY STREET

Winter Park, FL

Courtesy of MEP REALTY INVESTMENTS LLC
View 7426 WYNNEWOOD SQUARE 195 Winter Park, FL MLS# O6410726
$1,800
3

Beds

2.0

Baths

1,117

Sq.Ft.

7426 WYNNEWOOD SQUARE 195

Winter Park, FL

Courtesy of SPRINGHILL PROPERTIES LLC
View 614 SAINT JOHNS COURT 614 Winter Park, FL MLS# O6410529
$1,750
2

Beds

2.0

Baths

1,037

Sq.Ft.

614 SAINT JOHNS COURT 614

Winter Park, FL

Courtesy of JEXOR LLC
View 7864 BROKEN ARROW TRAIL Winter Park, FL MLS# O6406209
$3,400
4

Beds

2.1

Baths

2,219

Sq.Ft.

7864 BROKEN ARROW TRAIL

Winter Park, FL

View 784 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6408937
$5,500
3

Beds

2.1

Baths

1,940

Sq.Ft.

784 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 3232 ROYAL STREET Winter Park, FL MLS# O6407888
  • Virtual Tour
1 of 11
$1,745
3

Beds

1.1

Baths

970

Sq.Ft.

3232 ROYAL STREET

Winter Park, FL

View 1941 LANIER COURT Winter Park, FL MLS# O6404537
  • Virtual Tour
1 of 14
$1,620
2

Beds

1.0

Baths

865

Sq.Ft.

1941 LANIER COURT

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 625 TRINIDAD COURT 625 Winter Park, FL MLS# O6406224
$1,650
2

Beds

2.0

Baths

1,037

Sq.Ft.

625 TRINIDAD COURT 625

Winter Park, FL

Courtesy of ZEN LIVING HOMES 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

397

Estimated median home price

$849,000
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 41
$200K - 300K 24
$300K - 400K 22
$400K - 500K 29
$500K - 600K 31
$600K - 700K 29
$700K - 800K 19
$800K - 900K 14
$900K - 1M 9
$1M - Max 177

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 262
Townhouse 16
Condo 84
Commercial 7
Rental 73
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/21/2026)

Information deemed reliable but not guaranteed.

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

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 6/21/2026.