39 total properties
Did you mean the neighborhood Winter Park?
View 1210 FAIRWAY DR Winter Park, FL MLS# O6398533
  • Recently Listed
1 of 38
$549,000
3

Beds

2.0

Baths

1,737

Sq.Ft.

1210 FAIRWAY DR

Winter Park, FL

Courtesy of CENTRAL FLORIDA PRIME REAL ESTATE LLC
View 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
  • Recently Listed
1 of 28
$470,000
3

Beds

2.0

Baths

1,606

Sq.Ft.

950 HANOVER AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6393725
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Saturday 4/18 12:00 PM - 2:00 PM
$560,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 837 APPALACHEE AVENUE Winter Park, FL MLS# O6393151
$439,000
4

Beds

2.0

Baths

1,771

Sq.Ft.

837 APPALACHEE AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 518 SHOREVIEW AVENUE Winter Park, FL MLS# O6392797
$490,090
2

Beds

2.0

Baths

1,609

Sq.Ft.

518 SHOREVIEW AVENUE

Winter Park, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
  • Recently Listed with Virtual Tour
1 of 45
$459,999
3

Beds

2.0

Baths

1,491

Sq.Ft.

405 LAKE FAIR LANE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 512 N LAKEMONT AVENUE Winter Park, FL MLS# O6392353
$500,000
3

Beds

2.0

Baths

1,413

Sq.Ft.

512 N LAKEMONT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 300 CAROLINA AVENUE 207 Winter Park, FL MLS# O6391523
$495,000
1

Beds

2.0

Baths

1,149

Sq.Ft.

300 CAROLINA AVENUE 207

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1807 HAMMERLIN AVENUE G Winter Park, FL MLS# O6391277
$580,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1807 HAMMERLIN AVENUE G

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 2779 SANBINA STREET Winter Park, FL MLS# O6388746
$460,000
3

Beds

2.0

Baths

1,405

Sq.Ft.

2779 SANBINA STREET

Winter Park, FL

Courtesy of MAINFRAME REAL ESTATE
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$499,990
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP REALTY LLC
View Address not provided Winter Park, FL MLS# S5145631
$440,000
4

Beds

2.0

Baths

1,296

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of EXP REALTY LLC
View 3131 LOWNDES DRIVE Winter Park, FL MLS# O6388846
$534,900
4

Beds

2.0

Baths

2,126

Sq.Ft.

3131 LOWNDES DRIVE

Winter Park, FL

Courtesy of A +ROI PROPERTY
View 958 HANOVER AVENUE Winter Park, FL MLS# O6388088
$490,000
4

Beds

3.0

Baths

1,378

Sq.Ft.

958 HANOVER AVENUE

Winter Park, FL

Courtesy of AGILE GROUP REALTY
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 720 W WEBSTER AVENUE Winter Park, FL MLS# G5108643
$550,000
3

Beds

2.0

Baths

1,356

Sq.Ft.

720 W WEBSTER AVENUE

Winter Park, FL

Courtesy of SERHANT
View 4033 YACHT COURT Winter Park, FL MLS# O6379135
  • Virtual Tour
1 of 26
$549,000
3

Beds

2.0

Baths

2,268

Sq.Ft.

4033 YACHT COURT

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1036 ARAGON AVENUE Winter Park, FL MLS# O6382491
$510,000
2

Beds

1.0

Baths

1,073

Sq.Ft.

1036 ARAGON AVENUE

Winter Park, FL

Courtesy of WATSON REALTY CORP
View 1781 INDIANA AVENUE A Winter Park, FL MLS# O6381195
$545,000
3

Beds

2.1

Baths

1,616

Sq.Ft.

1781 INDIANA AVENUE A

Winter Park, FL

Courtesy of CARLISLE REALTY, LLC
View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
$495,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE 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

347

Estimated median home price

$779,000
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 - 100K4
$100K - 200K50
$200K - 300K21
$300K - 400K17
$400K - 500K28
$500K - 600K19
$600K - 700K22
$700K - 800K15
$800K - 900K11
$900K - 1M10
$1M - Max150

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family211
Townhouse13
Condo89
Commercial3
Rental90
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 4/14/2026)

Information deemed reliable but not guaranteed.

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 4/15/2026.

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 4/15/2026.