85 total properties
Did you mean the neighborhood Winter Park?
View 2306 LEE ROAD Winter Park, FL MLS# O6390092
  • Recently Listed with Virtual Tour
1 of 7
$119,568
2,289

Sq.Ft.

2306 LEE ROAD

Winter Park, FL

Courtesy of CENTURY 21 CARIOTI
View 687 HAROLD AVENUE Winter Park, FL MLS# O6387921
  • Recently Listed
1 of 3
$84,000
4,500

Sq.Ft.

687 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
View 4550 PALMETTO AVENUE Winter Park, FL MLS# O6388575
  • Recently Listed with Virtual Tour
1 of 28
$78,750
4,206

Sq.Ft.

4550 PALMETTO AVENUE

Winter Park, FL

Courtesy of SOLANTIS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 3029 FORSYTH ROAD Winter Park, FL MLS# O6348919
  • Virtual Tour
1 of 10
$42,000
1,500

Sq.Ft.

3029 FORSYTH ROAD

Winter Park, FL

Courtesy of C BRENNER INC
View 663 HAROLD AVENUE Winter Park, FL MLS# O6387903
  • Recently Listed with Virtual Tour
1 of 6
$42,000
10,429

Sq.Ft.

663 HAROLD AVENUE

Winter Park, FL

Courtesy of RCI REAL ESTATE INC.
View 7307 SANDSCOVE COURT 5 Winter Park, FL MLS# O6392725
  • Recently Listed
1 of 21
$42,000
23,760

Sq.Ft.

7307 SANDSCOVE COURT 5

Winter Park, FL

Courtesy of FUSILIER MANAGEMENT GROUP
View 7507 ALOMA AVENUE 3B Winter Park, FL MLS# O6353856
$28,800
1,444

Sq.Ft.

7507 ALOMA AVENUE 3B

Winter Park, FL

Courtesy of MUSA REALTY COMPANY INC
View 1221 RICHMOND ROAD Winter Park, FL MLS# O6365952
$19,000
5

Beds

5.1

Baths

5,164

Sq.Ft.

1221 RICHMOND ROAD

Winter Park, FL

Courtesy of LA ROSA REALTY LLC
View 1742 TEMPLE DRIVE Winter Park, FL MLS# O6378161
  • New Construction with Virtual Tour
1 of 27
$17,000
4

Beds

5.0

Baths

3,658

Sq.Ft.

1742 TEMPLE DRIVE

Winter Park, FL

Courtesy of ROI AVE LLC
View 1860 VIA CONTESSA Winter Park, FL MLS# O6389081
  • Recently Listed
1 of 90
$13,500
8

Beds

6.0

Baths

7,000

Sq.Ft.

1860 VIA CONTESSA

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 311 E MORSE BOULEVARD 1-5 Winter Park, FL MLS# O6376059
  • Adult Community
1 of 52
$8,950
3

Beds

3.0

Baths

2,462

Sq.Ft.

311 E MORSE BOULEVARD 1-5

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 300 KILLARNEY DRIVE Winter Park, FL MLS# O6361584
$7,900
4

Beds

3.0

Baths

2,476

Sq.Ft.

300 KILLARNEY DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1016 HOWELL BRANCH ROAD Winter Park, FL MLS# O6392422
  • Recently Listed with Virtual Tour
1 of 61
$7,200
4

Beds

3.0

Baths

3,142

Sq.Ft.

1016 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of PLAID PROPERTIES, LLC
View 519 PARK NORTH COURT Winter Park, FL MLS# O6365855
$7,000
4

Beds

3.2

Baths

3,302

Sq.Ft.

519 PARK NORTH COURT

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1350 LYNDALE BOULEVARD Winter Park, FL MLS# O6361248
$6,995
4

Beds

3.2

Baths

3,478

Sq.Ft.

1350 LYNDALE BOULEVARD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2075 JEWELL AVENUE Winter Park, FL MLS# O6386721
  • Recently Listed with Virtual Tour
1 of 65
$6,995
5

Beds

4.0

Baths

2,918

Sq.Ft.

2075 JEWELL AVENUE

Winter Park, FL

Courtesy of URBANISTA BROKERS
View 527 LANGHOLM DRIVE Winter Park, FL MLS# O6387427
  • Recently Listed with Virtual Tour
1 of 18
$6,750
4

Beds

3.1

Baths

3,276

Sq.Ft.

527 LANGHOLM DRIVE

Winter Park, FL

Courtesy of WOODRUFF REALTY, INC.
View 1049 N KENTUCKY AVENUE Winter Park, FL MLS# O6373029
$6,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

1049 N KENTUCKY AVENUE

Winter Park, FL

Courtesy of THE AGENCY FL
View 301 W COMSTOCK AVENUE Winter Park, FL MLS# O6385827
  • New Construction with Virtual Tour
1 of 12
$6,000
2

Beds

2.1

Baths

1,500

Sq.Ft.

301 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of THE SYDGAN CORP
View 1130 WASHINGTON AVENUE 11C Winter Park, FL MLS# O6384586
$5,995
3

Beds

2.1

Baths

2,069

Sq.Ft.

1130 WASHINGTON AVENUE 11C

Winter Park, FL

Courtesy of FUSILIER MANAGEMENT GROUP

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

318

Estimated median home price

$737,350
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 6
$100K - 200K 42
$200K - 300K 23
$300K - 400K 16
$400K - 500K 28
$500K - 600K 14
$600K - 700K 22
$700K - 800K 17
$800K - 900K 8
$900K - 1M 9
$1M - Max 133

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 183
Townhouse 17
Condo 83
Commercial 3
Rental 87
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 3/18/2026)

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 3/22/2026.