250 total properties
Did you mean the neighborhood Winter Park?
View 1913 WOODCREST DRIVE B Winter Park, FL MLS# O6366067
  • Recently Listed with Virtual Tour
1 of 22
$225,000
2

Beds

2.0

Baths

987

Sq.Ft.

1913 WOODCREST DRIVE B

Winter Park, FL

Courtesy of FUTURE HOME REALTY INC
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5139410
  • Recently Listed with Virtual Tour
1 of 37
$750,000
Studio

Beds

0.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2042 YORKSHIRE DRIVE Winter Park, FL MLS# O6366830
$499,000
Studio

Beds

0.0

Baths

2042 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 4876 TANGERINE AVENUE 4876 Winter Park, FL MLS# G5105277
$160,000
1

Beds

1.0

Baths

763

Sq.Ft.

4876 TANGERINE AVENUE 4876

Winter Park, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 1835 JESSICA COURT Winter Park, FL MLS# O6364599
$599,000
2

Beds

2.0

Baths

1,637

Sq.Ft.

1835 JESSICA COURT

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1817 JESSICA COURT Winter Park, FL MLS# O6364894
$525,000
3

Beds

2.0

Baths

1,870

Sq.Ft.

1817 JESSICA COURT

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 200 SAINT ANDREWS BOULEVARD 1905 Winter Park, FL MLS# O6360351
  • Recently Listed with Virtual Tour
1 of 24
$179,900
2

Beds

2.0

Baths

987

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 1905

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1611 WALNUT AVENUE Winter Park, FL MLS# O6365438
  • Recently Listed with Virtual Tour
1 of 41
$1,150,000
4

Beds

3.0

Baths

2,635

Sq.Ft.

1611 WALNUT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 676 DUNBLANE DRIVE Winter Park, FL MLS# O6365557
  • Recently Listed with Virtual Tour
1 of 35
$750,000
3

Beds

2.0

Baths

1,827

Sq.Ft.

676 DUNBLANE DRIVE

Winter Park, FL

Courtesy of BALDWIN PARK REALTY LLC
View 1929 S LAKEMONT AVENUE Winter Park, FL MLS# O6364557
  • Recently Listed with Virtual Tour
1 of 32
$949,000
3

Beds

3.1

Baths

2,160

Sq.Ft.

1929 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 503 W CANTON AVENUE Winter Park, FL MLS# O6367552
  • Recently Listed with Virtual Tour
1 of 37
$1,157,000
3

Beds

2.1

Baths

2,342

Sq.Ft.

503 W CANTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 875 W LYMAN AVENUE Winter Park, FL MLS# O6363961
$475,000
2

Beds

2.0

Baths

760

Sq.Ft.

875 W LYMAN AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2817 FITZOOTH DRIVE Winter Park, FL MLS# O6364062
$639,000
3

Beds

2.0

Baths

1,619

Sq.Ft.

2817 FITZOOTH DRIVE

Winter Park, FL

Courtesy of DJ & LINDSEY REAL ESTATE
View 1847 AZALEA AVENUE Winter Park, FL MLS# O6365286
$420,000
4

Beds

2.1

Baths

1,477

Sq.Ft.

1847 AZALEA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3236 KNOTTYPINE AVENUE Winter Park, FL MLS# O6364200
$429,000
3

Beds

2.0

Baths

1,578

Sq.Ft.

3236 KNOTTYPINE AVENUE

Winter Park, FL

Courtesy of URBAN-O REAL ESTATE SOLUTIONS
View 151 N ORLANDO AVENUE #115 Winter Park, FL MLS# O6362403
$298,000
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE #115

Winter Park, FL

Courtesy of CREEGAN GROUP
View 623 SAINT JOHNS COURT 623 Winter Park, FL MLS# O6362363
$200,000
2

Beds

2.0

Baths

1,120

Sq.Ft.

623 SAINT JOHNS COURT 623

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 1134 WASHINGTON AVENUE 13 Winter Park, FL MLS# O6362206
$675,000
3

Beds

3.1

Baths

2,083

Sq.Ft.

1134 WASHINGTON AVENUE 13

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2632 MANDAN TRAIL Winter Park, FL MLS# O6362577
$799,900
4

Beds

2.1

Baths

2,441

Sq.Ft.

2632 MANDAN TRAIL

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 1807 YORKSHIRE DRIVE Winter Park, FL MLS# TB8451098
$1,450,000
4

Beds

4.1

Baths

3,565

Sq.Ft.

1807 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of WEEKLEY HOMES REALTY COMPANY

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

299

Estimated median home price

$649,000
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

PriceCount
$0 - 100K7
$100K - 200K40
$200K - 300K21
$300K - 400K18
$400K - 500K30
$500K - 600K26
$600K - 700K21
$700K - 800K22
$800K - 900K5
$900K - 1M11
$1M - Max98

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family174
Townhouse19
Condo78
Commercial5
Rental108
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 12/25/2025)

Information deemed reliable but not guaranteed.

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Data is updated as of 12/25/2025.

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 12/25/2025.

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 12/25/2025.

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 12/25/2025.