289 total properties
Did you mean the neighborhood Winter Park?
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

View 1298 BEACHVIEW AVENUE Winter Park, FL MLS# O6405064
$4,200,000
Studio

Beds

0.0

Baths

1298 BEACHVIEW AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6404545
  • Virtual Tour
1 of 42
$780,000
5

Beds

3.0

Baths

2,194

Sq.Ft.

739 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of SERHANT
The time to sell is now! THE TIME TO SELL IS NOW!
View 1351 MAGNOLIA AVENUE Winter Park, FL MLS# O6404105
$3,100,000
5

Beds

4.1

Baths

3,460

Sq.Ft.

1351 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 7327 FOREST HILL COURT 223 Winter Park, FL MLS# O6403841
$180,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7327 FOREST HILL COURT 223

Winter Park, FL

View 1611 CHESTNUT AVENUE Winter Park, FL MLS# O6402502
  • Virtual Tour
1 of 50
$1,040,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

1611 CHESTNUT AVENUE

Winter Park, FL

View 3282 OAK LAKE PLACE 3282 Winter Park, FL MLS# O6403912
$154,500
2

Beds

1.1

Baths

990

Sq.Ft.

3282 OAK LAKE PLACE 3282

Winter Park, FL

View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
  • Virtual Tour
1 of 27
$535,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

View 1780 BRYAN AVENUE Winter Park, FL MLS# O6402643
  • Virtual Tour
1 of 8
$849,000
Studio

Beds

0.0

Baths

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
  • Virtual Tour
1 of 26
$240,000
3

Beds

3.0

Baths

1,578

Sq.Ft.

7484 CANFORD COURT 8

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1725 CAROLLEE LANE Winter Park, FL MLS# O6402656
  • Virtual Tour
1 of 41
$1,005,000
3

Beds

2.0

Baths

2,335

Sq.Ft.

1725 CAROLLEE LANE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 420 OHIO STREET Winter Park, FL MLS# O6399541
  • New Construction with Virtual Tour
1 of 8
$1,275,000
4

Beds

4.0

Baths

2,900

Sq.Ft.

420 OHIO STREET

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 726/720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6402984
$1,185,999
6

Beds

4.0

Baths

2,282

Sq.Ft.

726/720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 363 N PHELPS AVENUE Winter Park, FL MLS# O6401811
  • Virtual Tour
1 of 36
$1,249,000
4

Beds

3.0

Baths

2,871

Sq.Ft.

363 N PHELPS AVENUE

Winter Park, FL

View 2838 WRIGHT AVENUE Winter Park, FL MLS# O6399931
  • New Construction with Virtual Tour
1 of 10
$2,399,000
5

Beds

4.1

Baths

3,479

Sq.Ft.

2838 WRIGHT AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2889 ROUEN AVENUE Winter Park, FL MLS# L4961275
$365,000
3

Beds

2.0

Baths

1,144

Sq.Ft.

2889 ROUEN AVENUE

Winter Park, FL

View 446 MELROSE AVENUE Winter Park, FL MLS# O6402113
  • Virtual Tour
1 of 39
$1,625,000
4

Beds

2.0

Baths

2,640

Sq.Ft.

446 MELROSE AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 802 HAMILTON PLACE COURT Winter Park, FL MLS# O6398373
$1,324,000
4

Beds

3.1

Baths

2,843

Sq.Ft.

802 HAMILTON PLACE COURT

Winter Park, FL

Courtesy of FLORIDA CAPITAL REALTY
View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
  • Virtual Tour
1 of 13
$589,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

Courtesy of GALLOWAY REAL ESTATE
View 1398 GROVE TERRACE Winter Park, FL MLS# O6399698
  • Virtual Tour
1 of 58
$2,095,000
4

Beds

3.1

Baths

3,450

Sq.Ft.

1398 GROVE TERRACE

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

303

Estimated median home price

$799,000
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 7
$100K - 200K 39
$200K - 300K 16
$300K - 400K 14
$400K - 500K 22
$500K - 600K 22
$600K - 700K 22
$700K - 800K 10
$800K - 900K 11
$900K - 1M 7
$1M - Max 133

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 185
Townhouse 13
Condo 72
Commercial 7
Rental 67
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/16/2026)

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 7/17/2026.

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 7/17/2026.