215 total properties
Did you mean the neighborhood Winter Park?
View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
$515,000
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

Courtesy of CAISSA REALTY INVESTMENT INC
View 1745 INDIANA AVENUE J Winter Park, FL MLS# O6402920
$524,000
3

Beds

2.1

Baths

1,616

Sq.Ft.

1745 INDIANA AVENUE J

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
  • Virtual Tour
1 of 25
$250,000
3

Beds

2.1

Baths

1,578

Sq.Ft.

7484 CANFORD COURT 8

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 1900 WINTER PARK ROAD Winter Park, FL MLS# O6402566
$849,900
4

Beds

2.0

Baths

1,511

Sq.Ft.

1900 WINTER PARK ROAD

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 2829 ALOMA Winter Park, FL MLS# O6404107
  • Virtual Tour
1 of 36
$579,000
4

Beds

2.0

Baths

1,821

Sq.Ft.

2829 ALOMA

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 639 SAINT JOHNS COURT 639 Winter Park, FL MLS# O6402025
$199,900
2

Beds

2.0

Baths

1,120

Sq.Ft.

639 SAINT JOHNS COURT 639

Winter Park, FL

Courtesy of PLATINUM REALTY GROUP FLORIDA INC
View 1822 YORKSHIRE DRIVE Winter Park, FL MLS# O6401364
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1 of 42
$598,000
3

Beds

3.0

Baths

1,620

Sq.Ft.

1822 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1250 S DENNING DRIVE 117 Winter Park, FL MLS# O6401802
$240,000
2

Beds

1.1

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 117

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1881 W FAIRBANKS AVENUE Winter Park, FL MLS# O6401500
$700,000
1,264

Sq.Ft.

1881 W FAIRBANKS AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2889 ROUEN AVENUE Winter Park, FL MLS# L4961275
$399,500
3

Beds

2.0

Baths

1,144

Sq.Ft.

2889 ROUEN AVENUE

Winter Park, FL

Courtesy of HELLOSOLD LLC
View 3651 N GOLDENROD ROAD D102 Winter Park, FL MLS# O6401114
$159,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D102

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
  • Virtual Tour
1 of 29
$539,000
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1307 FORMOSA AVENUE Winter Park, FL MLS# O6400711
  • Virtual Tour
1 of 33
$373,800
2

Beds

1.0

Baths

1,150

Sq.Ft.

1307 FORMOSA AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1010 GARDEN DRIVE Winter Park, FL MLS# O6400287
  • Virtual Tour
1 of 37
$485,000
Studio

Beds

0.0

Baths

1010 GARDEN DRIVE

Winter Park, FL

Courtesy of WATSON REALTY CORP.
View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
  • Virtual Tour
1 of 13
$595,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

Courtesy of GALLOWAY REAL ESTATE
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

Courtesy of ORANGE SLICE PROPERTIES
View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
$595,000
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
  • Virtual Tour
1 of 9
$349,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RICK SINGH REAL ESTATE
View 1830 EDWIN BOULEVARD Winter Park, FL MLS# O6400055
  • Virtual Tour
1 of 52
$639,900
3

Beds

2.0

Baths

1,287

Sq.Ft.

1830 EDWIN BOULEVARD

Winter Park, FL

Courtesy of ZEN LIVING HOMES LLC
View 927 FAIRWAY DRIVE Winter Park, FL MLS# TB8498515
  • Virtual Tour
1 of 29
$680,000
4

Beds

3.0

Baths

1,918

Sq.Ft.

927 FAIRWAY DRIVE

Winter Park, FL

Courtesy of FLAT FEE MLS 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

399

Estimated median home price

$800,000
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 3
$100K - 200K 45
$200K - 300K 24
$300K - 400K 25
$400K - 500K 29
$500K - 600K 22
$600K - 700K 30
$700K - 800K 22
$800K - 900K 15
$900K - 1M 10
$1M - Max 174

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 261
Townhouse 13
Condo 86
Commercial 7
Rental 77
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/31/2026)

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 5/31/2026.

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 5/31/2026.

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 5/31/2026.

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 5/31/2026.