266 total properties
Did you mean the neighborhood Winter Park?
View 501 W CANTON AVENUE Winter Park, FL MLS# O6344716
  • Virtual Tour
1 of 29
$1,225,000
3

Beds

2.1

Baths

2,372

Sq.Ft.

501 W CANTON AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 244 OSCEOLA COURT Winter Park, FL MLS# O6372232
$1,200,000
4

Beds

2.1

Baths

1,837

Sq.Ft.

244 OSCEOLA COURT

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1602 ALABAMA DRIVE 403 Winter Park, FL MLS# O6373348
$1,195,000
2

Beds

2.0

Baths

1,402

Sq.Ft.

1602 ALABAMA DRIVE 403

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1860 STAUNTON AVENUE Winter Park, FL MLS# O6378554
  • New Construction with Virtual Tour
1 of 10
$1,195,000
4

Beds

3.1

Baths

2,525

Sq.Ft.

1860 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 100 S INTERLACHEN AVENUE 404 Winter Park, FL MLS# O6375851
$1,165,000
2

Beds

2.0

Baths

1,220

Sq.Ft.

100 S INTERLACHEN AVENUE 404

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1800 MAGNOLIA AVENUE Winter Park, FL MLS# NS1087637
  • Recently Listed with Virtual Tour
1 of 65
OPEN HOUSE: Saturday 3/28 12:00 PM - 3:00 PM
$1,150,000
4

Beds

2.1

Baths

2,431

Sq.Ft.

1800 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 503 W CANTON AVENUE Winter Park, FL MLS# O6367552
  • Virtual Tour
1 of 45
$1,146,000
3

Beds

2.1

Baths

2,342

Sq.Ft.

503 W CANTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1802 ARBOR PARK DRIVE Winter Park, FL MLS# O6372857
$1,125,000
4

Beds

3.0

Baths

1,808

Sq.Ft.

1802 ARBOR PARK DRIVE

Winter Park, FL

Courtesy of TBRO REALTY LLC
View 1541 WESTCHESTER AVENUE Winter Park, FL MLS# O6374409
$1,100,000
3

Beds

2.1

Baths

2,578

Sq.Ft.

1541 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1541 WESTCHESTER AVENUE Winter Park, FL MLS# O6374414
$1,100,000
Studio

Beds

0.0

Baths

1541 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1768 MONDRIAN CIRCLE Winter Park, FL MLS# O6375723
  • Recently Listed with 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 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 2607 Lafayette Ave Winter Park, FL MLS# A11826269
  • Virtual Tour
1 of 71
$1,095,000
4

Beds

3.1

Baths

2,770

Sq.Ft.

2607 Lafayette Ave

Winter Park, FL

Courtesy of FORTUNE CHRISTIE'S INTERNATIONAL REAL ESTATE
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 1836 GRINNELL TERRACE Winter Park, FL MLS# O6380457
$1,050,000
3

Beds

2.0

Baths

1,907

Sq.Ft.

1836 GRINNELL TERRACE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 456 CAROLINA AVENUE Winter Park, FL MLS# O6385625
  • Virtual Tour
1 of 46
$1,010,000
3

Beds

3.0

Baths

1,615

Sq.Ft.

456 CAROLINA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1822 GREENWICH AVENUE Winter Park, FL MLS# A4669605
$995,000
3

Beds

2.0

Baths

1,627

Sq.Ft.

1822 GREENWICH AVENUE

Winter Park, FL

Courtesy of FLATFEE.COM
View 1405 MILLER AVENUE Winter Park, FL MLS# O6386405
  • Virtual Tour
1 of 46
$950,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1405 MILLER AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 870 CARVER STREET Winter Park, FL MLS# O6360210
  • New Construction with Virtual Tour
1 of 53
$949,900
3

Beds

3.0

Baths

1,875

Sq.Ft.

870 CARVER STREET

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 29
$949,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA 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

328

Estimated median home price

$762,500
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 46
$200K - 300K 21
$300K - 400K 16
$400K - 500K 29
$500K - 600K 15
$600K - 700K 22
$700K - 800K 17
$800K - 900K 10
$900K - 1M 9
$1M - Max 139

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 192
Townhouse 19
Condo 83
Commercial 3
Rental 86
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 3/24/2026)

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 3/25/2026.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 3/25/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include 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 3/25/2026.

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 3/25/2026.