129 total properties
Did you mean the neighborhood Winter Park?
View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
  • Recently Listed with Virtual Tour
1 of 35
OPEN HOUSE: Sunday 5/17 1:00 PM - 4:00 PM
$410,000
3

Beds

2.0

Baths

1,402

Sq.Ft.

7532 AZUREBROOK COURT

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2482 ROXBURY ROAD Winter Park, FL MLS# O6406443
  • Recently Listed with Virtual Tour
1 of 20
$400,000
2

Beds

1.0

Baths

913

Sq.Ft.

2482 ROXBURY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
  • Recently Listed with Virtual Tour
1 of 33
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
  • Recently Listed with Virtual Tour
1 of 31
OPEN HOUSE: Saturday 5/16 1:00 PM - 3:00 PM
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 731 BONGART ROAD Winter Park, FL MLS# O6406004
  • Recently Listed
1 of 44
$499,000
4

Beds

3.0

Baths

1,526

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 819 DENSMORE DRIVE Winter Park, FL MLS# O6405658
  • Virtual Tour
1 of 39
$375,000
3

Beds

2.0

Baths

1,300

Sq.Ft.

819 DENSMORE DRIVE

Winter Park, FL

Courtesy of DON HARKINS REALTY LLC
View 2500 LEE ROAD 232 Winter Park, FL MLS# O6404916
  • Recently Listed with Virtual Tour
1 of 26
$164,900
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 232

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 721 DUNBAR STREET Winter Park, FL MLS# O6405338
  • Virtual Tour
1 of 36
$399,999
2

Beds

2.0

Baths

1,018

Sq.Ft.

721 DUNBAR STREET

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1695 LEE ROAD E116 Winter Park, FL MLS# O6399346
  • Recently Listed with Virtual Tour
1 of 29
$125,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E116

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 4772 TANGERINE AVENUE 4772 Winter Park, FL MLS# O6405042
  • Recently Listed with Virtual Tour
1 of 32
OPEN HOUSE: Saturday 5/16 1:00 PM - 3:00 PM
$199,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4772 TANGERINE AVENUE 4772

Winter Park, FL

Courtesy of THE WILKINS WAY LLC
View 3371 RIVER VIEW WAY 46 Winter Park, FL MLS# O6403947
  • Recently Listed with Virtual Tour
1 of 45
OPEN HOUSE: Saturday 5/16 12:00 PM - 2:00 PM
$205,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

3371 RIVER VIEW WAY 46

Winter Park, FL

Courtesy of REALTY ONE GROUP EVOLVE
View 2237 WOODCREST DRIVE Winter Park, FL MLS# O6404115
$490,000
3

Beds

2.0

Baths

1,492

Sq.Ft.

2237 WOODCREST DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 7327 FOREST HILL COURT 223 Winter Park, FL MLS# O6403841
  • Recently Listed with Virtual Tour
1 of 18
$190,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7327 FOREST HILL COURT 223

Winter Park, FL

Courtesy of M L VAZ REALTY INC
View 3282 OAK LAKE PLACE 3282 Winter Park, FL MLS# O6403912
  • Recently Listed with Virtual Tour
1 of 27
$169,500
2

Beds

1.1

Baths

990

Sq.Ft.

3282 OAK LAKE PLACE 3282

Winter Park, FL

Courtesy of BUSBY REALTY LLC
View 3053 GEORGE MASON AVENUE 8A Winter Park, FL MLS# O6402957
$75,000
1

Beds

1.0

Baths

809

Sq.Ft.

3053 GEORGE MASON AVENUE 8A

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
  • Recently Listed
1 of 42
$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
  • Recently Listed with 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
View 639 SAINT JOHNS COURT 639 Winter Park, FL MLS# O6402025
  • Recently Listed with Virtual Tour
1 of 42
$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 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

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

379

Estimated median home price

$795,000
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 50
$200K - 300K 21
$300K - 400K 20
$400K - 500K 31
$500K - 600K 22
$600K - 700K 26
$700K - 800K 18
$800K - 900K 13
$900K - 1M 9
$1M - Max 166

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 236
Townhouse 13
Condo 87
Commercial 7
Rental 77
Lots and Land 27
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 0

(Data as of 5/14/2026)

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 5/15/2026.

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 5/15/2026.

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 5/15/2026.