219 total properties
Did you mean the neighborhood Winter Park?
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
  • Virtual Tour
1 of 7
$459,900
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 259 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6419225
$459,900
3

Beds

2.0

Baths

1,248

Sq.Ft.

259 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 316 BECKETT COURT Winter Park, FL MLS# O6411108
  • Virtual Tour
1 of 33
$450,000
4

Beds

2.0

Baths

1,651

Sq.Ft.

316 BECKETT COURT

Winter Park, FL

Courtesy of VINTAGE REALTY SOLUTIONS
The time to sell is now! THE TIME TO SELL IS NOW!
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$449,900
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP REALTY LLC
View JESSICA COURT Winter Park, FL MLS# O6419256
  • Virtual Tour
1 of 11
$449,000
Studio

Beds

0.0

Baths

JESSICA COURT

Winter Park, FL

View 2611 LOTAFUN AVENUE Winter Park, FL MLS# O6422197
  • Virtual Tour
1 of 34
$449,000
3

Beds

2.0

Baths

1,838

Sq.Ft.

2611 LOTAFUN AVENUE

Winter Park, FL

View 2007 CORNELL AVENUE Winter Park, FL MLS# O6428423
  • Recently Listed with Virtual Tour
1 of 35
$449,000
3

Beds

2.0

Baths

1,154

Sq.Ft.

2007 CORNELL AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2041 JEWELL AVENUE Winter Park, FL MLS# O6420660
  • Virtual Tour
1 of 30
$439,900
3

Beds

1.0

Baths

1,508

Sq.Ft.

2041 JEWELL AVENUE

Winter Park, FL

Courtesy of IAD REAL ESTATE
View 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
  • Virtual Tour
1 of 45
$435,000
3

Beds

2.0

Baths

1,491

Sq.Ft.

405 LAKE FAIR LANE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 405 Lake Fair Lane Winter Park, FL MLS# A12062271
  • Recently Listed with Virtual Tour
1 of 18
$434,990
3

Beds

2.0

Baths

405 Lake Fair Lane

Winter Park, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View Address not provided Winter Park, FL MLS# S5145631
  • Virtual Tour
1 of 11
$430,000
4

Beds

2.0

Baths

1,296

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2249 MINNESOTA AVENUE Winter Park, FL MLS# O6419820
$429,900
4

Beds

2.0

Baths

1,536

Sq.Ft.

2249 MINNESOTA AVENUE

Winter Park, FL

View 2323 DEVON COURT Winter Park, FL MLS# O6418530
  • Virtual Tour
1 of 35
$429,000
4

Beds

2.0

Baths

2,403

Sq.Ft.

2323 DEVON COURT

Winter Park, FL

View 814 DENSMORE DR Winter Park, FL MLS# O6399773
  • Virtual Tour
1 of 24
$425,000
4

Beds

2.0

Baths

1,610

Sq.Ft.

814 DENSMORE DR

Winter Park, FL

View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
View 644 N KNOWLES AVENUE 3 Winter Park, FL MLS# O6420484
$425,000
1

Beds

1.0

Baths

767

Sq.Ft.

644 N KNOWLES AVENUE 3

Winter Park, FL

View 1909 TAYLOR AVENUE Winter Park, FL MLS# O6426549
$425,000
Studio

Beds

0.0

Baths

1909 TAYLOR AVENUE

Winter Park, FL

View 2568 LOTAFUN AVENUE Winter Park, FL MLS# W7887744
  • Recently Listed with Virtual Tour
1 of 25
$409,900
3

Beds

2.0

Baths

1,201

Sq.Ft.

2568 LOTAFUN AVENUE

Winter Park, FL

View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
$399,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

View 3054 BLUEBROOK DRIVE Winter Park, FL MLS# O6398450
  • Virtual Tour
1 of 44
$389,500
3

Beds

2.0

Baths

1,939

Sq.Ft.

3054 BLUEBROOK DRIVE

Winter Park, FL

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

353

Estimated median home price

$725,000
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 7
$100K - 200K 39
$200K - 300K 21
$300K - 400K 14
$400K - 500K 34
$500K - 600K 28
$600K - 700K 32
$700K - 800K 14
$800K - 900K 11
$900K - 1M 11
$1M - Max 142

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 218
Townhouse 22
Condo 77
Commercial 9
Rental 68
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 8/7/2026)

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 8/7/2026.

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 8/7/2026.