47 total properties
Did you mean the neighborhood Winter Park?
View 512 N LAKEMONT AVENUE Winter Park, FL MLS# O6392353
  • Recently Listed with Virtual Tour
1 of 43
$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
  • Recently Listed with Virtual Tour
1 of 27
$550,000
1

Beds

2.0

Baths

1,149

Sq.Ft.

300 CAROLINA AVENUE 207

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1760 GREENWICH AVENUE Winter Park, FL MLS# O6392001
  • Recently Listed with Virtual Tour
1 of 18
OPEN HOUSE: Saturday 3/21 1:00 PM - 3:00 PM
$650,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

1760 GREENWICH AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
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 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
  • Recently Listed with Virtual Tour
1 of 17
$499,990
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 259 E CANTON AVENUE 259 Winter Park, FL MLS# O6389246
  • Recently Listed with Virtual Tour
1 of 36
$649,000
2

Beds

2.0

Baths

1,040

Sq.Ft.

259 E CANTON AVENUE 259

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 218 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6388723
  • Recently Listed with Virtual Tour
1 of 29
$635,000
3

Beds

2.0

Baths

1,618

Sq.Ft.

218 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 3131 LOWNDES DRIVE Winter Park, FL MLS# O6388846
  • Recently Listed with Virtual Tour
1 of 24
$542,000
4

Beds

2.0

Baths

2,126

Sq.Ft.

3131 LOWNDES DRIVE

Winter Park, FL

Courtesy of A +ROI PROPERTY
View 1926 NATALEN ROAD Winter Park, FL MLS# O6388308
  • Recently Listed with Virtual Tour
1 of 44
OPEN HOUSE: Saturday 3/21 1:00 PM - 4:00 PM
$649,900
3

Beds

2.0

Baths

1,469

Sq.Ft.

1926 NATALEN ROAD

Winter Park, FL

Courtesy of JAMIESON PROPERTIES, INC.
View 1354 INDIANA AVENUE Winter Park, FL MLS# O6387500
  • Recently Listed with Virtual Tour
1 of 39
$599,900
3

Beds

2.0

Baths

1,269

Sq.Ft.

1354 INDIANA AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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 275 N RANGER BOULEVARD Winter Park, FL MLS# TB8484642
$499,000
4

Beds

3.0

Baths

1,864

Sq.Ft.

275 N RANGER BOULEVARD

Winter Park, FL

Courtesy of ON POINT REALTY LLC
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 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
  • Recently Listed with Virtual Tour
1 of 50
$635,000
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

Courtesy of EQUITYPRO LLC
View 720 W WEBSTER AVENUE Winter Park, FL MLS# G5108643
  • Recently Listed with Virtual Tour
1 of 43
OPEN HOUSE: Saturday 3/21 10:00 AM - 4:00 PM
$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
$525,000
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
$575,000
3

Beds

2.1

Baths

1,616

Sq.Ft.

1781 INDIANA AVENUE A

Winter Park, FL

Courtesy of CARLISLE REALTY, LLC
View 1137 OAKS BOULEVARD Winter Park, FL MLS# O6379388
$634,900
2

Beds

1.1

Baths

1,149

Sq.Ft.

1137 OAKS BOULEVARD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 1860 STAUNTON AVENUE Winter Park, FL MLS# O6378461
$630,000
Studio

Beds

0.0

Baths

1860 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA 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

318

Estimated median home price

$737,350
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 - 100K6
$100K - 200K42
$200K - 300K23
$300K - 400K16
$400K - 500K28
$500K - 600K14
$600K - 700K22
$700K - 800K17
$800K - 900K8
$900K - 1M9
$1M - Max133

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family183
Townhouse17
Condo83
Commercial3
Rental87
Lots and Land24
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 3/18/2026)

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 3/21/2026.

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 3/21/2026.