360 total properties
Did you mean the neighborhood Winter Park?
View 470 W COMSTOCK AVENUE Winter Park, FL MLS# W7890730
  • Recently Listed with Virtual Tour
1 of 59
$5,480,000
6

Beds

6.1

Baths

6,134

Sq.Ft.

470 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of EQUITY PARTNERS REAL EST LLC
View 1124 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6455137
$1,650,000
3

Beds

3.0

Baths

2,254

Sq.Ft.

1124 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1351 MAYFIELD AVENUE Winter Park, FL MLS# O6455383
  • Recently Listed with Virtual Tour
1 of 13
$3,050,000
5

Beds

4.1

Baths

3,677

Sq.Ft.

1351 MAYFIELD AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 610 PENN PLACE Winter Park, FL MLS# O6456172
  • Recently Listed with Virtual Tour
1 of 54
$1,895,000
4

Beds

4.0

Baths

3,174

Sq.Ft.

610 PENN PLACE

Winter Park, FL

Courtesy of COLLADO REAL ESTATE
View 1008 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6457191
$2,500,000
4

Beds

4.1

Baths

3,530

Sq.Ft.

1008 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2718 EASTERN PARKWAY Winter Park, FL MLS# O6453504
  • Recently Listed with Virtual Tour
1 of 41
OPEN HOUSE: Sunday 11/15 1:00 PM - 4:00 PM
$2,450,000
4

Beds

4.1

Baths

3,308

Sq.Ft.

2718 EASTERN PARKWAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 647 RANDY LANE Winter Park, FL MLS# O6456258
  • Recently Listed with Virtual Tour
1 of 56
$1,699,999
4

Beds

3.1

Baths

2,923

Sq.Ft.

647 RANDY LANE

Winter Park, FL

Courtesy of SHAWFIELD REALTY GROUP
View 2821 CHANTILLY AVENUE Winter Park, FL MLS# V4952171
  • Recently Listed
1 of 35
$415,000
3

Beds

2.0

Baths

1,440

Sq.Ft.

2821 CHANTILLY AVENUE

Winter Park, FL

Courtesy of RISE REALTY OF FLORIDA LLC
View 2531 PASSAMONTE DRIVE 4H Winter Park, FL MLS# O6452859
  • Recently Listed with Virtual Tour
1 of 28
$369,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2531 PASSAMONTE DRIVE 4H

Winter Park, FL

Courtesy of REDFIN CORPORATION
View 617 N INTERLACHEN Avenue Winter Park, FL MLS# B26099444
$4,695,000
11

Beds

7.1

Baths

4,603

Sq.Ft.

617 N INTERLACHEN Avenue

Winter Park, FL

View 531 WORTHINGTON DRIVE Winter Park, FL MLS# O6457145
  • Recently Listed with Virtual Tour
1 of 8
OPEN HOUSE: Sunday 11/15 12:00 PM - 2:00 PM
$1,100,000
0.0

Baths

531 WORTHINGTON DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2821 RIDDLE DRIVE Winter Park, FL MLS# O6457113
  • Recently Listed with Virtual Tour
1 of 28
$299,900
4

Beds

2.2

Baths

2,445

Sq.Ft.

2821 RIDDLE DRIVE

Winter Park, FL

Courtesy of ORLANDO REGIONAL REALTY
View 2507 LAFAYETTE AVENUE Winter Park, FL MLS# O6450302
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Saturday 11/14 12:00 PM - 2:00 PM
$1,850,000
4

Beds

4.2

Baths

2,675

Sq.Ft.

2507 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View Address not provided Winter Park, FL MLS# O6456614
  • Recently Listed
1 of 56
$2,100,000
4

Beds

4.1

Baths

2,830

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of PLATINUM REALTY GROUP FLORIDA INC
View 1756 HOLLYWOOD AVENUE Winter Park, FL MLS# O6456803
$1,500,000
0.0

Baths

1756 HOLLYWOOD AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 535 N INTERLACHEN AVENUE 302 Winter Park, FL MLS# O6452921
  • Recently Listed with Virtual Tour
1 of 33
$485,000
2

Beds

2.0

Baths

970

Sq.Ft.

535 N INTERLACHEN AVENUE 302

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1934 TAYLOR AVENUE Winter Park, FL MLS# O6455676
  • Recently Listed with Virtual Tour
1 of 42
$499,000
4

Beds

1.1

Baths

1,470

Sq.Ft.

1934 TAYLOR AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 531 WORTHINGTON DRIVE Winter Park, FL MLS# O6455524
  • Recently Listed with Virtual Tour
1 of 32
OPEN HOUSE: Sunday 11/15 12:00 PM - 2:00 PM
$1,100,000
3

Beds

3.0

Baths

2,626

Sq.Ft.

531 WORTHINGTON DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2885 ROXBURY ROAD Winter Park, FL MLS# O6456440
  • Recently Listed with Virtual Tour
1 of 20
$450,000
3

Beds

2.0

Baths

1,511

Sq.Ft.

2885 ROXBURY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 662 TRINIDAD COURT 662 Winter Park, FL MLS# O6456448
$177,000
1

Beds

1.0

Baths

759

Sq.Ft.

662 TRINIDAD COURT 662

Winter Park, FL

Courtesy of CLARA HERRERA 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

360

Estimated median home price

$842,500
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 32
$200K - 300K 25
$300K - 400K 18
$400K - 500K 32
$500K - 600K 23
$600K - 700K 26
$700K - 800K 17
$800K - 900K 17
$900K - 1M 11
$1M - Max 155

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 213
Townhouse 23
Condo 80
Commercial 15
Rental 99
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 11/13/2026)

Information deemed reliable but not guaranteed.

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 11/13/2026.