166 total properties
Did you mean the neighborhood Winter Park?
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6449858
  • Virtual Tour
1 of 30
$575,000
3

Beds

2.0

Baths

1,804

Sq.Ft.

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6449843
  • Virtual Tour
1 of 30
$575,000
0.0

Baths

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2141 LAKE DRIVE Winter Park, FL MLS# O6453477
  • Virtual Tour
1 of 25
$569,900
3

Beds

2.0

Baths

1,824

Sq.Ft.

2141 LAKE DRIVE

Winter Park, FL

Courtesy of SHORES REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 7525 LODGE POLE TRAIL Winter Park, FL MLS# O6417303
$550,000
4

Beds

2.0

Baths

1,936

Sq.Ft.

7525 LODGE POLE TRAIL

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 257 LINCOLNSHIRE ROAD Winter Park, FL MLS# O6453656
$550,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

257 LINCOLNSHIRE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1003 LAKE BELL DRIVE Winter Park, FL MLS# O6418278
  • Virtual Tour
1 of 30
$549,900
3

Beds

2.0

Baths

1,837

Sq.Ft.

1003 LAKE BELL DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
  • Virtual Tour
1 of 31
$540,000
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
  • Virtual Tour
1 of 37
$535,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2627 AMBERGATE ROAD Winter Park, FL MLS# O6433352
  • Virtual Tour
1 of 16
$530,000
4

Beds

3.0

Baths

1,745

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 510 FITZWALTER DRIVE Winter Park, FL MLS# O6448189
  • Virtual Tour
1 of 27
$530,000
3

Beds

2.0

Baths

1,385

Sq.Ft.

510 FITZWALTER DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2641 CARVELL COURT Winter Park, FL MLS# O6430894
  • Virtual Tour
1 of 37
$525,000
4

Beds

2.0

Baths

2,126

Sq.Ft.

2641 CARVELL COURT

Winter Park, FL

Courtesy of CHAMBERLAIN REALTY LLC
View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
$524,900
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 731 BONGART ROAD Winter Park, FL MLS# O6448911
$519,900
4

Beds

3.0

Baths

1,842

Sq.Ft.

731 BONGART ROAD

Winter Park, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
  • Virtual Tour
1 of 27
$515,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 1061 ARAGON AVENUE 1061 Winter Park, FL MLS# S5152353
$510,000
3

Beds

2.1

Baths

1,669

Sq.Ft.

1061 ARAGON AVENUE 1061

Winter Park, FL

Courtesy of WATSON REALTY CORP
View 808 DENSMORE DRIVE Winter Park, FL MLS# O6451977
  • Recently Listed with Virtual Tour
1 of 26
$509,999
3

Beds

2.0

Baths

1,460

Sq.Ft.

808 DENSMORE DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
  • Virtual Tour
1 of 30
$499,900
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 230 STRATHY LANE Winter Park, FL MLS# O6371054
  • Virtual Tour
1 of 12
$499,000
2

Beds

1.0

Baths

920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 2231 NAIRN DRIVE Winter Park, FL MLS# O6369016
  • Virtual Tour
1 of 19
$499,000
3

Beds

2.0

Baths

1,088

Sq.Ft.

2231 NAIRN DRIVE

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 230 STRATHY LANE Winter Park, FL MLS# O6426909
$499,000
920

Sq.Ft.

230 STRATHY LANE

Winter Park, FL

Courtesy of PARK TOWN 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

357

Estimated median home price

$849,000
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 4
$100K - 200K 32
$200K - 300K 24
$300K - 400K 17
$400K - 500K 31
$500K - 600K 23
$600K - 700K 26
$700K - 800K 18
$800K - 900K 17
$900K - 1M 12
$1M - Max 153

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 211
Townhouse 25
Condo 79
Commercial 15
Rental 98
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 11/12/2026)

Information deemed reliable but not guaranteed.

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 11/12/2026.