311 total properties
Did you mean the neighborhood Winter Park?
View 632 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6250417
$1,050,000
3

Beds

2.0

Baths

2,342

Sq.Ft.

632 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 1741 MIZELL AVENUE Winter Park, FL MLS# O6410059
  • Virtual Tour
1 of 41
OPEN HOUSE: Saturday 7/11 2:00 PM - 4:00 PM
$1,050,000
3

Beds

2.0

Baths

2,015

Sq.Ft.

1741 MIZELL AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1138 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6420090
  • Recently Listed with Virtual Tour
1 of 35
$1,050,000
3

Beds

3.0

Baths

2,434

Sq.Ft.

1138 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1611 CHESTNUT AVENUE Winter Park, FL MLS# O6402502
  • Virtual Tour
1 of 50
OPEN HOUSE: Sunday 7/12 1:00 PM - 3:00 PM
$1,070,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

1611 CHESTNUT AVENUE

Winter Park, FL

View 2607 LAFAYETTE AVENUE Winter Park, FL MLS# O6314734
$1,095,000
4

Beds

3.1

Baths

2,770

Sq.Ft.

2607 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of FORTUNE INTERNATIONAL REALTY
View 1120 WISCONSIN AVENUE Winter Park, FL MLS# O6406800
$1,095,000
3

Beds

3.1

Baths

2,213

Sq.Ft.

1120 WISCONSIN AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1768 MONDRIAN CIRCLE Winter Park, FL MLS# O6375723
  • Virtual Tour
1 of 26
$1,099,000
3

Beds

3.1

Baths

2,193

Sq.Ft.

1768 MONDRIAN CIRCLE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2702 PARKLAND DRIVE Winter Park, FL MLS# O6397997
  • Virtual Tour
1 of 48
OPEN HOUSE: Sunday 7/12 1:00 PM - 3:00 PM
$1,099,000
5

Beds

3.0

Baths

2,656

Sq.Ft.

2702 PARKLAND DRIVE

Winter Park, FL

View 1981 BLUE RIDGE ROAD Winter Park, FL MLS# O6402961
  • Virtual Tour
1 of 52
$1,150,000
4

Beds

2.0

Baths

2,750

Sq.Ft.

1981 BLUE RIDGE ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1404 BORDER DRIVE Winter Park, FL MLS# O6412140
  • Virtual Tour
1 of 38
$1,150,000
4

Beds

4.0

Baths

2,469

Sq.Ft.

1404 BORDER DRIVE

Winter Park, FL

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 1500 HARRIS CIRCLE Winter Park, FL MLS# O6379012
  • Virtual Tour
1 of 27
$1,195,000
2

Beds

3.0

Baths

2,096

Sq.Ft.

1500 HARRIS CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2111 MALLARD CIRCLE Winter Park, FL MLS# O6401350
  • Virtual Tour
1 of 28
$1,199,000
4

Beds

3.0

Baths

2,667

Sq.Ft.

2111 MALLARD CIRCLE

Winter Park, FL

View 1870 WALKER AVENUE Winter Park, FL MLS# O6390504
  • New Construction with Virtual Tour
1 of 32
$1,225,000
3

Beds

2.1

Baths

2,046

Sq.Ft.

1870 WALKER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
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 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
  • Recently Listed with Virtual Tour
1 of 46
$1,249,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6406381
  • New Construction with Virtual Tour
1 of 25
$1,249,900
4

Beds

3.1

Baths

2,936

Sq.Ft.

Address not provided

Winter Park, FL

View 1870 STAUNTON AVENUE Winter Park, FL MLS# O6391469
  • New Construction with Virtual Tour
1 of 10
$1,250,000
4

Beds

3.1

Baths

2,525

Sq.Ft.

1870 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1600 ALABAMA DRIVE 402 Winter Park, FL MLS# O6413153
$1,250,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

1600 ALABAMA DRIVE 402

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6418198
  • Recently Listed with Virtual Tour
1 of 31
OPEN HOUSE: Saturday 7/11 12:00 PM - 4:00 PM
$1,275,000
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

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

309

Estimated median home price

$725,000
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 43
$200K - 300K 18
$300K - 400K 13
$400K - 500K 26
$500K - 600K 21
$600K - 700K 25
$700K - 800K 11
$800K - 900K 9
$900K - 1M 6
$1M - Max 133

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 189
Townhouse 13
Condo 76
Commercial 6
Rental 70
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/9/2026)

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.

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 7/9/2026.

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

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 7/9/2026.