185 total properties
Did you mean the neighborhood Winter Park?
View 1760 BRYAN AVENUE Winter Park, FL MLS# O6348488
  • Virtual Tour
1 of 8
$800,000
Studio

Beds

0.0

Baths

1760 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1770 BRYAN AVENUE Winter Park, FL MLS# O6348521
  • Virtual Tour
1 of 7
$800,000
Studio

Beds

0.0

Baths

1770 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1780 BRYAN AVENUE Winter Park, FL MLS# O6365369
  • Recently Listed with Virtual Tour
1 of 8
$800,000
4

Beds

2.0

Baths

1,617

Sq.Ft.

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 2632 MANDAN TRAIL Winter Park, FL MLS# O6362577
  • Virtual Tour
1 of 30
$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 1278 S PENNSYLVANIA AVENUE 13 Winter Park, FL MLS# O6330567
$769,000
3

Beds

2.1

Baths

1,957

Sq.Ft.

1278 S PENNSYLVANIA AVENUE 13

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 625 BRECHIN DRIVE Winter Park, FL MLS# O6280564
  • Virtual Tour
1 of 42
$765,000
3

Beds

2.0

Baths

1,827

Sq.Ft.

625 BRECHIN DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2002 KAROLINA AVENUE Winter Park, FL MLS# O6327155
$750,000
Studio

Beds

0.0

Baths

2002 KAROLINA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
  • Virtual Tour
1 of 30
$750,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1712 GOLFSIDE DRIVE Winter Park, FL MLS# O6359653
  • Virtual Tour
1 of 44
$750,000
4

Beds

2.0

Baths

2,111

Sq.Ft.

1712 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 676 DUNBLANE DRIVE Winter Park, FL MLS# O6365557
  • 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 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 1213 LINDENWOOD LANE Winter Park, FL MLS# O6362048
  • Recently Listed with Virtual Tour
1 of 29
$750,000
4

Beds

2.0

Baths

2,505

Sq.Ft.

1213 LINDENWOOD LANE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1324 INDIANA AVENUE Winter Park, FL MLS# O6357852
  • Virtual Tour
1 of 21
$745,000
4

Beds

2.1

Baths

1,692

Sq.Ft.

1324 INDIANA AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 2955 LOLISSA LANE Winter Park, FL MLS# O6345484
  • Virtual Tour
1 of 58
$739,000
4

Beds

3.0

Baths

3,538

Sq.Ft.

2955 LOLISSA LANE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 300 CAROLINA AVENUE 201 Winter Park, FL MLS# O6366544
  • Recently Listed with Virtual Tour
1 of 19
$739,000
2

Beds

2.0

Baths

1,305

Sq.Ft.

300 CAROLINA AVENUE 201

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 3018 NORTHWOOD BOULEVARD Winter Park, FL MLS# G5103499
$733,000
3

Beds

2.0

Baths

1,761

Sq.Ft.

3018 NORTHWOOD BOULEVARD

Winter Park, FL

Courtesy of ROCK SPRINGS REALTY, LLC
View 3377 FORSYTH ROAD Winter Park, FL MLS# O6173998
  • Virtual Tour
1 of 15
$725,000
4,104

Sq.Ft.

3377 FORSYTH ROAD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 770 W WEBSTER AVENUE Winter Park, FL MLS# O6323574
  • Virtual Tour
1 of 34
$725,000
4

Beds

2.0

Baths

1,008

Sq.Ft.

770 W WEBSTER AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 770 W WEBSTER AVENUE REAR LOT Winter Park, FL MLS# O6323647
$725,000
Studio

Beds

0.0

Baths

770 W WEBSTER AVENUE REAR LOT

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2418 WHITEHALL CIRCLE Winter Park, FL MLS# O6288728
$715,000
3

Beds

2.0

Baths

2,134

Sq.Ft.

2418 WHITEHALL CIRCLE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY

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

301

Estimated median home price

$639,000
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 6
$100K - 200K 40
$200K - 300K 21
$300K - 400K 19
$400K - 500K 32
$500K - 600K 26
$600K - 700K 21
$700K - 800K 22
$800K - 900K 5
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 176
Townhouse 19
Condo 77
Commercial 5
Rental 108
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 12/29/2025)

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 12/29/2025.

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 12/29/2025.

Copyright 2025 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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 12/29/2025.

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 12/29/2025.