166 total properties
Did you mean the neighborhood Winter Park?
View 1652 BERKSHIRE AVENUE Winter Park, FL MLS# O6432617
$429,000
3

Beds

2.0

Baths

1,498

Sq.Ft.

1652 BERKSHIRE AVENUE

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 1909 TAYLOR AVENUE Winter Park, FL MLS# O6426549
$425,000
0.0

Baths

1909 TAYLOR AVENUE

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 3157 SHADY PINE AVENUE Winter Park, FL MLS# O6455299
  • Recently Listed with Virtual Tour
1 of 31
$425,000
3

Beds

2.0

Baths

1,495

Sq.Ft.

3157 SHADY PINE AVENUE

Winter Park, FL

Courtesy of MID-STATE PROPERTIES PSL LLC
View 712 BAFFIE AVENUE Winter Park, FL MLS# O6445837
$419,900
3

Beds

1.0

Baths

1,304

Sq.Ft.

712 BAFFIE AVENUE

Winter Park, FL

Courtesy of RP INVESTMENT REALTY LLC
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$419,000
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2126 ALBERT LEE PARKWAY Winter Park, FL MLS# O6435973
$415,000
3

Beds

2.0

Baths

1,187

Sq.Ft.

2126 ALBERT LEE PARKWAY

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2821 CHANTILLY AVENUE Winter Park, FL MLS# V4952171
$415,000
3

Beds

2.0

Baths

1,440

Sq.Ft.

2821 CHANTILLY AVENUE

Winter Park, FL

Courtesy of RISE REALTY OF FLORIDA LLC
View 603 CARNATION DRIVE Winter Park, FL MLS# TB8561386
  • Recently Listed with Virtual Tour
1 of 12
$399,900
4

Beds

2.0

Baths

1,427

Sq.Ft.

603 CARNATION DRIVE

Winter Park, FL

Courtesy of A-WARD WINNING REALTY LLC
View 2176 CRANDON AVENUE Winter Park, FL MLS# O6455726
  • Recently Listed with Virtual Tour
1 of 19
$399,000
2

Beds

1.0

Baths

959

Sq.Ft.

2176 CRANDON AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
$395,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RICK SINGH REAL ESTATE
View 1955 ELAND AVENUE Winter Park, FL MLS# O6433345
$394,900
3

Beds

2.0

Baths

1,494

Sq.Ft.

1955 ELAND AVENUE

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
View 2626 AMBERGATE ROAD Winter Park, FL MLS# O6439689
$380,000
3

Beds

1.0

Baths

1,143

Sq.Ft.

2626 AMBERGATE ROAD

Winter Park, FL

Courtesy of OLDE TOWN BROKERS INC
View 2531 PASSAMONTE DRIVE 4H Winter Park, FL MLS# O6452859
  • Recently Listed with Virtual Tour
1 of 28
$369,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2531 PASSAMONTE DRIVE 4H

Winter Park, FL

Courtesy of REDFIN CORPORATION
View 885 CARNATION DRIVE Winter Park, FL MLS# S5153456
$368,000
4

Beds

2.0

Baths

1,240

Sq.Ft.

885 CARNATION DRIVE

Winter Park, FL

Courtesy of RADIUS REALTY GROUP LLC
View 7506 CRANES CREEK COURT 30 Winter Park, FL MLS# S5156844
$365,000
3

Beds

2.1

Baths

1,861

Sq.Ft.

7506 CRANES CREEK COURT 30

Winter Park, FL

Courtesy of TRANSCONTINENTAL REALTY GROUP,
View 500 N PENNSYLVANIA AVENUE G Winter Park, FL MLS# G5117377
$349,500
2

Beds

1.0

Baths

709

Sq.Ft.

500 N PENNSYLVANIA AVENUE G

Winter Park, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1306 S PENNSYLVANIA AVENUE 5 Winter Park, FL MLS# O6443013
$347,500
2

Beds

1.0

Baths

830

Sq.Ft.

1306 S PENNSYLVANIA AVENUE 5

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2526 PASSAMONTE DRIVE 10F Winter Park, FL MLS# O6418710
$335,000
3

Beds

2.1

Baths

1,790

Sq.Ft.

2526 PASSAMONTE DRIVE 10F

Winter Park, FL

Courtesy of LEGACY CORNERSTONE INC
View 220 KILLARNEY BAY COURT 6-2 Winter Park, FL MLS# O6450663
$335,000
2

Beds

2.0

Baths

1,140

Sq.Ft.

220 KILLARNEY BAY COURT 6-2

Winter Park, FL

Courtesy of COLDWELL BANKER 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

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

PriceCount
$0 - 100K4
$100K - 200K32
$200K - 300K24
$300K - 400K17
$400K - 500K31
$500K - 600K23
$600K - 700K26
$700K - 800K18
$800K - 900K17
$900K - 1M12
$1M - Max153

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family211
Townhouse25
Condo79
Commercial15
Rental98
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(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.