281 total properties
Did you mean the neighborhood Winter Park?
View 1220 HOWELL BRANCH ROAD Winter Park, FL MLS# O6437591
$950,000
3

Beds

2.0

Baths

1,487

Sq.Ft.

1220 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of PARK PLACE REAL ESTATE
View 913 MOSS LANE Winter Park, FL MLS# O6441449
  • Virtual Tour
1 of 30
$950,000
3

Beds

2.0

Baths

1,887

Sq.Ft.

913 MOSS LANE

Winter Park, FL

Courtesy of VECTOR REALTY
View 1411 DEVON ROAD Winter Park, FL MLS# O6449441
  • Recently Listed with Virtual Tour
1 of 47
$950,000
2

Beds

2.0

Baths

1,947

Sq.Ft.

1411 DEVON ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1138 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6420090
$925,000
3

Beds

3.0

Baths

2,434

Sq.Ft.

1138 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 471 HOLT AVENUE Winter Park, FL MLS# O6437590
  • Virtual Tour
1 of 27
$925,000
4

Beds

3.0

Baths

2,528

Sq.Ft.

471 HOLT AVENUE

Winter Park, FL

Courtesy of FLORIDA HOME TEAM REALTY LLC
View 1927 S LAKEMONT AVENUE Winter Park, FL MLS# O6426102
$915,000
3

Beds

3.1

Baths

2,093

Sq.Ft.

1927 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of IAD REAL ESTATE
View 2572 FIFESHIRE DRIVE Winter Park, FL MLS# O6442325
  • Virtual Tour
1 of 47
$899,900
4

Beds

2.1

Baths

2,578

Sq.Ft.

2572 FIFESHIRE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
  • Virtual Tour
1 of 7
$899,000
0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 269 E CANTON AVENUE 269 Winter Park, FL MLS# O6404706
$899,000
1

Beds

1.1

Baths

1,109

Sq.Ft.

269 E CANTON AVENUE 269

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
$899,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

Courtesy of ORLANDO HOMES GROUP LLC
View 311 E MORSE BOULEVARD 4-5 Winter Park, FL MLS# O6432808
  • Adult Community with Virtual Tour
1 of 39
$895,000
2

Beds

2.0

Baths

1,763

Sq.Ft.

311 E MORSE BOULEVARD 4-5

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 618 BLAIRSHIRE CIRCLE Winter Park, FL MLS# O6439298
$875,000
4

Beds

3.0

Baths

1,876

Sq.Ft.

618 BLAIRSHIRE CIRCLE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 870 N PHELPS AVENUE Winter Park, FL MLS# O6445731
  • Virtual Tour
1 of 15
$850,000
4

Beds

3.0

Baths

2,301

Sq.Ft.

870 N PHELPS AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 870 N PHELPS AVENUE Winter Park, FL MLS# O6445759
  • Virtual Tour
1 of 15
$850,000
0.0

Baths

870 N PHELPS AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 775 MCINTYRE AVENUE 9 Winter Park, FL MLS# O6449033
$849,999
3

Beds

2.1

Baths

2,052

Sq.Ft.

775 MCINTYRE AVENUE 9

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, LLC
View 2011 HARMON AVENUE Winter Park, FL MLS# O6453173
  • Recently Listed
1 of 2
$849,900
4

Beds

3.0

Baths

2,434

Sq.Ft.

2011 HARMON AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 36
$849,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 437 N CAPEN AVENUE Winter Park, FL MLS# O6414283
  • Virtual Tour
1 of 36
$849,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

437 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1621 CHESTNUT AVENUE Winter Park, FL MLS# O6435086
  • Virtual Tour
1 of 35
$845,000
3

Beds

2.1

Baths

2,022

Sq.Ft.

1621 CHESTNUT AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 338 BLUE HERON DRIVE Winter Park, FL MLS# O6410174
  • Virtual Tour
1 of 42
$836,000
3

Beds

3.0

Baths

2,017

Sq.Ft.

338 BLUE HERON DRIVE

Winter Park, FL

Courtesy of STOCKWORTH REALTY GROUP

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

365

Estimated median home price

$825,000
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 34
$200K - 300K 21
$300K - 400K 16
$400K - 500K 31
$500K - 600K 26
$600K - 700K 33
$700K - 800K 16
$800K - 900K 17
$900K - 1M 13
$1M - Max 154

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 218
Townhouse 23
Condo 79
Commercial 15
Rental 90
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 11/1/2026)

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 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 11/2/2026.

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 11/2/2026.