133 total properties
Did you mean the neighborhood Winter Park?
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
$605,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5139410
$605,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
$599,999
0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 822 SYMONDS AVENUE Winter Park, FL MLS# O6441180
$599,999
0.0

Baths

822 SYMONDS AVENUE

Winter Park, FL

Courtesy of NEWBERRY REALTY & DEV GRP INC.
View 1946 STRATHAVEN ROAD Winter Park, FL MLS# O6411329
$599,000
4

Beds

3.0

Baths

2,102

Sq.Ft.

1946 STRATHAVEN ROAD

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 4026 TENITA DRIVE Winter Park, FL MLS# O6430278
$599,000
3

Beds

2.0

Baths

2,031

Sq.Ft.

4026 TENITA DRIVE

Winter Park, FL

Courtesy of RUBY DAVIS, BROKER
View 508 BRECHIN DRIVE Winter Park, FL MLS# O6439220
$599,000
3

Beds

2.0

Baths

1,783

Sq.Ft.

508 BRECHIN DRIVE

Winter Park, FL

Courtesy of MTL REALTY LLC
View 1071 ARAGON AVENUE Winter Park, FL MLS# O6429215
$575,000
2

Beds

2.1

Baths

1,851

Sq.Ft.

1071 ARAGON AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1259 INDIANA AVENUE Winter Park, FL MLS# O6434701
  • Virtual Tour
1 of 67
OPEN HOUSE: Saturday 10/31 1:00 PM - 4:00 PM
$575,000
2

Beds

2.1

Baths

1,648

Sq.Ft.

1259 INDIANA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 112 BELL PLACE Winter Park, FL MLS# O6446595
  • Virtual Tour
1 of 31
$575,000
3

Beds

2.0

Baths

2,253

Sq.Ft.

112 BELL PLACE

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 1399 ALOMA AVENUE Winter Park, FL MLS# O6449858
  • Recently Listed with 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
  • Recently Listed with Virtual Tour
1 of 30
$575,000
0.0

Baths

1399 ALOMA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 346 ELKHORN COURT Winter Park, FL MLS# O6449383
$575,000
4

Beds

2.0

Baths

1,891

Sq.Ft.

346 ELKHORN COURT

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
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
  • Recently Listed with Virtual Tour
1 of 34
$550,000
3

Beds

2.0

Baths

1,610

Sq.Ft.

257 LINCOLNSHIRE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
$549,900
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1003 LAKE BELL DRIVE Winter Park, FL MLS# O6418278
$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
$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
$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
$530,000
4

Beds

3.0

Baths

1,745

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK

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

360

Estimated median home price

$799,999
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 - 100K3
$100K - 200K35
$200K - 300K20
$300K - 400K15
$400K - 500K31
$500K - 600K26
$600K - 700K35
$700K - 800K16
$800K - 900K15
$900K - 1M13
$1M - Max151

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family215
Townhouse22
Condo77
Commercial15
Rental90
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 10/30/2026)

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 10/30/2026.