46 total properties
Did you mean the neighborhood Winter Park?
View 640 N PARK AVENUE 26 Winter Park, FL MLS# O6456509
  • Recently Listed with Virtual Tour
1 of 19
$629,500
2

Beds

2.0

Baths

858

Sq.Ft.

640 N PARK AVENUE 26

Winter Park, FL

Courtesy of MICHAEL O'SHAUGHNESSY, INC.
View 1140 WASHINGTON AVENUE 16C Winter Park, FL MLS# O6456091
  • Recently Listed with Virtual Tour
1 of 10
OPEN HOUSE: Friday 11/13 4:00 PM - 7:00 PM
$739,000
3

Beds

2.1

Baths

2,069

Sq.Ft.

1140 WASHINGTON AVENUE 16C

Winter Park, FL

Courtesy of CHEVON EATON
View 1261 MICHIGAN AVENUE Winter Park, FL MLS# O6450090
  • Recently Listed with Virtual Tour
1 of 42
OPEN HOUSE: Saturday 11/14 1:00 PM - 3:00 PM
$650,000
3

Beds

2.1

Baths

1,798

Sq.Ft.

1261 MICHIGAN AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 1780 BRYAN AVENUE Winter Park, FL MLS# O6453790
  • Recently Listed with Virtual Tour
1 of 5
$825,000
0.0

Baths

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1401 PELHAM ROAD Winter Park, FL MLS# O6452727
$650,000
3

Beds

2.0

Baths

1,594

Sq.Ft.

1401 PELHAM ROAD

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 624 DUNRAVEN DRIVE Winter Park, FL MLS# O6443159
  • Virtual Tour
1 of 24
$620,000
3

Beds

2.0

Baths

1,762

Sq.Ft.

624 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1884 JESSICA COURT Winter Park, FL MLS# O6450978
  • Virtual Tour
1 of 33
$699,900
3

Beds

2.0

Baths

1,666

Sq.Ft.

1884 JESSICA COURT

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 2887 TEMPLE TRAIL Winter Park, FL MLS# O6450536
  • Virtual Tour
1 of 86
$695,000
2

Beds

2.1

Baths

1,801

Sq.Ft.

2887 TEMPLE TRAIL

Winter Park, FL

Courtesy of ADAIR REALTY INC
View 640 N PARK AVENUE 3 Winter Park, FL MLS# O6446483
$745,000
2

Beds

1.1

Baths

897

Sq.Ft.

640 N PARK AVENUE 3

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 518 GILBERT ROAD Winter Park, FL MLS# O6442915
  • Virtual Tour
1 of 48
$639,000
3

Beds

2.0

Baths

1,573

Sq.Ft.

518 GILBERT ROAD

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 2322 WOODCREST DRIVE Winter Park, FL MLS# O6445796
  • Virtual Tour
1 of 28
OPEN HOUSE: Saturday 11/14 11:00 AM - 1:00 PM
$650,000
4

Beds

2.0

Baths

1,650

Sq.Ft.

2322 WOODCREST DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2139 BLOSSOM LANE Winter Park, FL MLS# O6446509
  • Virtual Tour
1 of 6
$699,000
0.0

Baths

2139 BLOSSOM LANE

Winter Park, FL

Courtesy of ORLANDO BROTHERS REAL ESTATE LLC
View 100 S INTERLACHEN AVENUE 401 Winter Park, FL MLS# O6443942
$825,000
3

Beds

2.0

Baths

1,639

Sq.Ft.

100 S INTERLACHEN AVENUE 401

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 266 N RANGER BOULEVARD Winter Park, FL MLS# O6444727
$724,900
4

Beds

3.0

Baths

1,692

Sq.Ft.

266 N RANGER BOULEVARD

Winter Park, FL

Courtesy of ELITE PROPERTY REAL ESTATE LLC
View 1003 GOLFSIDE DRIVE Winter Park, FL MLS# O6444366
  • Virtual Tour
1 of 28
$749,900
3

Beds

3.0

Baths

2,145

Sq.Ft.

1003 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of QP HOMES REALTY LLC
View 250 CAROLINA AVENUE 202 Winter Park, FL MLS# O6442686
$649,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

250 CAROLINA AVENUE 202

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2345 BROOKSHIRE AVENUE Winter Park, FL MLS# O6439369
$795,000
3

Beds

3.0

Baths

2,488

Sq.Ft.

2345 BROOKSHIRE AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6442348
  • Virtual Tour
1 of 41
OPEN HOUSE: Saturday 11/14 12:00 PM - 2:00 PM
$637,500
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1431 PALM AVENUE Winter Park, FL MLS# O6441550
  • Virtual Tour
1 of 17
$799,999
0.0

Baths

1431 PALM AVENUE

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 2410 SHERBROOKE ROAD Winter Park, FL MLS# O6439553
  • Virtual Tour
1 of 73
$769,000
4

Beds

2.1

Baths

2,141

Sq.Ft.

2410 SHERBROOKE ROAD

Winter Park, FL

Courtesy of AMERICA REAL ESTATE COMPANY 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.