291 total properties
Did you mean the neighborhood Winter Park?
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 2814 SHERIFF WAY Winter Park, FL MLS# O6383098
  • Virtual Tour
1 of 55
$574,900
4

Beds

2.0

Baths

1,948

Sq.Ft.

2814 SHERIFF WAY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
  • Virtual Tour
1 of 47
OPEN HOUSE: Saturday 4/25 2:30 PM - 4:30 PM
$627,500
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

Courtesy of EQUITYPRO LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2501 WINTER PARK ROAD Winter Park, FL MLS# O6384756
$1,690,000
5

Beds

3.1

Baths

3,304

Sq.Ft.

2501 WINTER PARK ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 628 DUNBLANE DRIVE Winter Park, FL MLS# O6387091
  • Virtual Tour
1 of 54
$849,000
3

Beds

2.1

Baths

2,114

Sq.Ft.

628 DUNBLANE DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 647 RANDY LANE Winter Park, FL MLS# O6387217
  • Recently Listed
1 of 64
$1,795,000
4

Beds

3.1

Baths

2,851

Sq.Ft.

647 RANDY LANE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 629 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6386610
  • New Construction with Virtual Tour
1 of 46
$1,695,000
4

Beds

3.1

Baths

3,031

Sq.Ft.

629 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of CLASSIC HOMES
View 1108 FAIRWAY DRIVE Winter Park, FL MLS# O6386266
  • Virtual Tour
1 of 46
OPEN HOUSE: Saturday 4/25 2:00 PM - 4:00 PM
$725,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

1108 FAIRWAY DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7336 FOREST HILL COURT 240 Winter Park, FL MLS# O6386461
$169,900
2

Beds

1.1

Baths

990

Sq.Ft.

7336 FOREST HILL COURT 240

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1405 MILLER AVENUE Winter Park, FL MLS# O6386405
  • Virtual Tour
1 of 46
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1405 MILLER AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2500 LEE ROAD 122 Winter Park, FL MLS# O6384082
  • Virtual Tour
1 of 25
$179,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 122

Winter Park, FL

Courtesy of PINEAPPLE PLACE REALTY, LLC
View 200 SAINT ANDREWS BOULEVARD 705 Winter Park, FL MLS# O6386469
$180,000
1

Beds

1.0

Baths

727

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 705

Winter Park, FL

Courtesy of WINTER PARK REAL ESTATE CO LLC
View 7117 SWALLOW RUN G1 Winter Park, FL MLS# O6385942
$249,800
3

Beds

2.1

Baths

1,565

Sq.Ft.

7117 SWALLOW RUN G1

Winter Park, FL

Courtesy of COMPLETE FLORIDA REALTY LLC
View 643 DUNBLANE DRIVE Winter Park, FL MLS# O6386136
  • Virtual Tour
1 of 62
$699,800
3

Beds

2.0

Baths

1,575

Sq.Ft.

643 DUNBLANE DRIVE

Winter Park, FL

Courtesy of ZEN LIVING HOMES LLC
View 765 BAFFIE AVENUE Winter Park, FL MLS# O6384768
  • Virtual Tour
1 of 23
$380,000
2

Beds

1.0

Baths

936

Sq.Ft.

765 BAFFIE AVENUE

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 1500 GAY ROAD 20D Winter Park, FL MLS# O6385626
  • Virtual Tour
1 of 22
$262,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 20D

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 4768 TANGERINE AVENUE 4768 Winter Park, FL MLS# S5144503
$185,000
1

Beds

1.0

Baths

753

Sq.Ft.

4768 TANGERINE AVENUE 4768

Winter Park, FL

Courtesy of PROPERTY OUTLET INTERNATIONAL
View 669 W COMSTOCK AVENUE Winter Park, FL MLS# TB8479258
$190,000
Studio

Beds

0.0

Baths

669 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of HOMECOIN.COM
View 2454 BROOKSHIRE AVENUE Winter Park, FL MLS# O6384924
  • New Construction with Virtual Tour
1 of 34
$1,399,000
4

Beds

3.1

Baths

2,509

Sq.Ft.

2454 BROOKSHIRE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1000 S SEMORAN BOULEVARD 715 Winter Park, FL MLS# S5144243
$122,990
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 715

Winter Park, FL

Courtesy of LPT REALTY, 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

368

Estimated median home price

$775,000
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 51
$200K - 300K 22
$300K - 400K 19
$400K - 500K 31
$500K - 600K 21
$600K - 700K 25
$700K - 800K 16
$800K - 900K 13
$900K - 1M 10
$1M - Max 156

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 225
Townhouse 17
Condo 87
Commercial 3
Rental 95
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 4/21/2026)

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 4/21/2026.

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 4/21/2026.

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 4/21/2026.

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 4/21/2026.