354 total properties
Did you mean the neighborhood Winter Park?
View 1905 BONANZA CT Winter Park, FL MLS# O6398772
  • Recently Listed with Virtual Tour
1 of 34
OPEN HOUSE: Sunday 4/19 11:00 AM - 1:00 PM
$490,000
4

Beds

2.0

Baths

1,774

Sq.Ft.

1905 BONANZA CT

Winter Park, FL

Courtesy of REAL LIVING R E SOLUTIONS
View 1661 WOODLAND Winter Park, FL MLS# O6399334
  • Recently Listed with Virtual Tour
1 of 15
$1,300,000
Studio

Beds

0.0

Baths

1661 WOODLAND

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1661 WOODLAND AVENUE Winter Park, FL MLS# O6399348
  • Recently Listed with Virtual Tour
1 of 58
$1,300,000
3

Beds

3.1

Baths

3,215

Sq.Ft.

1661 WOODLAND AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 2361 MULBRY DRIVE Winter Park, FL MLS# O6396840
  • Recently Listed with Virtual Tour
1 of 87
OPEN HOUSE: Saturday 4/18 12:00 PM - 2:00 PM
$2,395,000
4

Beds

4.0

Baths

3,111

Sq.Ft.

2361 MULBRY DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1398 GROVE TERRACE Winter Park, FL MLS# O6399698
  • Recently Listed with Virtual Tour
1 of 55
$2,195,000
4

Beds

3.1

Baths

3,450

Sq.Ft.

1398 GROVE TERRACE

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 814 DENSMORE DR Winter Park, FL MLS# O6399773
  • Recently Listed with Virtual Tour
1 of 24
$425,000
4

Beds

2.0

Baths

1,610

Sq.Ft.

814 DENSMORE DR

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 1807 MAGNOLIA AVENUE Winter Park, FL MLS# O6396616
  • Recently Listed with Virtual Tour
1 of 38
$1,199,000
5

Beds

3.0

Baths

2,618

Sq.Ft.

1807 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
  • Recently Listed with Virtual Tour
1 of 24
$609,900
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 3651 N GOLDENROD ROAD E106 Winter Park, FL MLS# O6399937
  • Recently Listed with Virtual Tour
1 of 27
$172,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD E106

Winter Park, FL

Courtesy of USCO CAPITAL GROUP
View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
  • Recently Listed with Virtual Tour
1 of 9
$349,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RICK SINGH REAL ESTATE
View 1830 EDWIN BOULEVARD Winter Park, FL MLS# O6400055
  • Recently Listed with Virtual Tour
1 of 52
OPEN HOUSE: Saturday 4/18 11:00 AM - 1:00 PM
$679,800
3

Beds

2.0

Baths

1,287

Sq.Ft.

1830 EDWIN BOULEVARD

Winter Park, FL

Courtesy of ZEN LIVING HOMES LLC
View 2020 VIA TUSCANY Winter Park, FL MLS# O6400063
  • Recently Listed
1 of 94
$4,195,000
4

Beds

4.1

Baths

4,665

Sq.Ft.

2020 VIA TUSCANY

Winter Park, FL

Courtesy of VISTA CAY REALTY COMPANY
View 3028 GEORGE MASON AVENUE J-7E Winter Park, FL MLS# O6398380
  • Recently Listed with Virtual Tour
1 of 25
$105,000
2

Beds

2.0

Baths

1,088

Sq.Ft.

3028 GEORGE MASON AVENUE J-7E

Winter Park, FL

Courtesy of EXP REALTY LLC
View 3172 CROWN JEWEL COURT Winter Park, FL MLS# O6397498
  • Recently Listed with Virtual Tour
1 of 24
$339,900
3

Beds

2.1

Baths

1,406

Sq.Ft.

3172 CROWN JEWEL COURT

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1441 CARDINAL COURT Winter Park, FL MLS# O6399395
  • Recently Listed with Virtual Tour
1 of 85
$4,285,000
4

Beds

5.1

Baths

4,066

Sq.Ft.

1441 CARDINAL COURT

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1785 WALNUT AVENUE Winter Park, FL MLS# O6399577
  • Recently Listed with Virtual Tour
1 of 35
$825,000
Studio

Beds

0.0

Baths

1785 WALNUT AVENUE

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
View 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6386578
  • Recently Listed with Virtual Tour
1 of 29
$229,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE REALTY
View 102 BELL PLACE Winter Park, FL MLS# O6398118
  • Recently Listed with Virtual Tour
1 of 46
OPEN HOUSE: Saturday 4/18 1:00 PM - 4:00 PM
$1,399,000
4

Beds

3.1

Baths

2,459

Sq.Ft.

102 BELL PLACE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1960 WINTER PARK ROAD Winter Park, FL MLS# O6398264
$899,000
Studio

Beds

0.0

Baths

1960 WINTER PARK ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1540 MILLER AVENUE Winter Park, FL MLS# O6398421
  • Recently Listed with Virtual Tour
1 of 55
OPEN HOUSE: Saturday 4/18 12:00 PM - 3:00 PM
$1,399,900
4

Beds

3.1

Baths

2,984

Sq.Ft.

1540 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION

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

355

Estimated median home price

$795,000
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 50
$200K - 300K 22
$300K - 400K 18
$400K - 500K 29
$500K - 600K 19
$600K - 700K 23
$700K - 800K 14
$800K - 900K 13
$900K - 1M 10
$1M - Max 153

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 215
Townhouse 14
Condo 89
Commercial 3
Rental 91
Lots and Land 27
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 4/16/2026)

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 4/17/2026.

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 4/17/2026.

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 4/17/2026.

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.

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 4/17/2026.