165 total properties
Did you mean the neighborhood Winter Park?
View 1009 LAKE BELL DRIVE Winter Park, FL MLS# O6410167
$650,000
Studio

Beds

0.0

Baths

1009 LAKE BELL DRIVE

Winter Park, FL

View 2923 ANTIQUE OAKS CIRCLE 34 Winter Park, FL MLS# S5150301
$180,000
2

Beds

2.0

Baths

1,105

Sq.Ft.

2923 ANTIQUE OAKS CIRCLE 34

Winter Park, FL

View 200 SAINT ANDREWS BOULEVARD 704 Winter Park, FL MLS# O6411608
$164,999
1

Beds

1.0

Baths

793

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 704

Winter Park, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1707 HARMON AVENUE Winter Park, FL MLS# O6409180
  • Virtual Tour
1 of 37
OPEN HOUSE: Saturday 7/25 1:00 PM - 3:00 PM
$639,000
3

Beds

2.0

Baths

1,669

Sq.Ft.

1707 HARMON AVENUE

Winter Park, FL

View 925 S SEMORAN BOULEVARD 103 Winter Park, FL MLS# O6409391
$373,000
1,454

Sq.Ft.

925 S SEMORAN BOULEVARD 103

Winter Park, FL

View 1500 GAY ROAD 17D Winter Park, FL MLS# O6408516
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1 of 38
$249,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 17D

Winter Park, FL

View 2973 SANBINA STREET Winter Park, FL MLS# O6407521
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1 of 36
$377,880
3

Beds

2.0

Baths

1,128

Sq.Ft.

2973 SANBINA STREET

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
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 2482 ROXBURY ROAD Winter Park, FL MLS# O6406443
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1 of 20
$375,000
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
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

View 731 BONGART ROAD Winter Park, FL MLS# O6406004
$499,000
4

Beds

3.0

Baths

1,526

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

View 3371 RIVER VIEW WAY 46 Winter Park, FL MLS# O6403947
$205,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

3371 RIVER VIEW WAY 46

Winter Park, FL

View 7327 FOREST HILL COURT 223 Winter Park, FL MLS# O6403841
$180,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7327 FOREST HILL COURT 223

Winter Park, FL

View 3282 OAK LAKE PLACE 3282 Winter Park, FL MLS# O6403912
$154,500
2

Beds

1.1

Baths

990

Sq.Ft.

3282 OAK LAKE PLACE 3282

Winter Park, FL

View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
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1 of 27
$535,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
1 of 42
OPEN HOUSE: Saturday 7/25 2:30 AM - 5:00 PM
$495,900
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

View 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
  • Virtual Tour
1 of 26
$240,000
3

Beds

3.0

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
$194,900
2

Beds

2.0

Baths

1,120

Sq.Ft.

639 SAINT JOHNS COURT 639

Winter Park, FL

View 1822 YORKSHIRE DRIVE Winter Park, FL MLS# O6401364
  • Virtual Tour
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

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

381

Estimated median home price

$799,000
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 43
$200K - 300K 24
$300K - 400K 18
$400K - 500K 29
$500K - 600K 24
$600K - 700K 33
$700K - 800K 14
$800K - 900K 15
$900K - 1M 9
$1M - Max 165

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 233
Townhouse 20
Condo 84
Commercial 11
Rental 68
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 7/23/2026)

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 7/24/2026.

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 7/24/2026.