31 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 1138 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6420090
  • Recently Listed with Virtual Tour
1 of 35
$1,050,000
3

Beds

3.0

Baths

2,434

Sq.Ft.

1138 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1600 ALABAMA DRIVE 402 Winter Park, FL MLS# O6413153
$1,250,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

1600 ALABAMA DRIVE 402

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1321 FAIRVIEW AVENUE Winter Park, FL MLS# O6412568
$1,200,000
Studio

Beds

0.0

Baths

1321 FAIRVIEW AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1404 BORDER DRIVE Winter Park, FL MLS# O6412140
  • Virtual Tour
1 of 38
$1,175,000
4

Beds

4.0

Baths

2,469

Sq.Ft.

1404 BORDER DRIVE

Winter Park, FL

View 241 W LAKE SUE AVENUE Winter Park, FL MLS# O6411621
$999,000
3

Beds

2.1

Baths

2,304

Sq.Ft.

241 W LAKE SUE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1120 WISCONSIN AVENUE Winter Park, FL MLS# O6406800
$1,095,000
3

Beds

3.1

Baths

2,213

Sq.Ft.

1120 WISCONSIN AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 616 BRECHIN DRIVE Winter Park, FL MLS# O6409911
  • Virtual Tour
1 of 44
$1,045,000
4

Beds

4.1

Baths

2,638

Sq.Ft.

616 BRECHIN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1741 MIZELL AVENUE Winter Park, FL MLS# O6410059
  • Virtual Tour
1 of 41
$1,050,000
3

Beds

2.0

Baths

2,015

Sq.Ft.

1741 MIZELL AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 269 E CANTON AVENUE 269 Winter Park, FL MLS# O6404706
$989,500
1

Beds

1.1

Baths

1,109

Sq.Ft.

269 E CANTON AVENUE 269

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View Address not provided Winter Park, FL MLS# O6406381
  • New Construction with Virtual Tour
1 of 25
$1,249,900
4

Beds

3.1

Baths

2,936

Sq.Ft.

Address not provided

Winter Park, FL

View 1600 S PENNSYLVANIA AVENUE Winter Park, FL MLS# NS1088189
$1,200,000
3

Beds

2.0

Baths

2,158

Sq.Ft.

1600 S PENNSYLVANIA AVENUE

Winter Park, FL

View 1600 S PENNSYLVANIA AVENUE Winter Park, FL MLS# NS1088189
$1,200,000
3

Beds

2.0

Baths

2,158

Sq.Ft.

1600 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of EXIT REAL ESTATE PROPERTY SOL
View 2232 BANCHORY ROAD Winter Park, FL MLS# O6404702
  • Virtual Tour
1 of 44
$1,115,000
4

Beds

3.0

Baths

2,597

Sq.Ft.

2232 BANCHORY ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1611 CHESTNUT AVENUE Winter Park, FL MLS# O6402502
  • Virtual Tour
1 of 45
$1,070,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

1611 CHESTNUT AVENUE

Winter Park, FL

View 1725 CAROLLEE LANE Winter Park, FL MLS# O6402656
  • Virtual Tour
1 of 41
$1,005,000
3

Beds

2.0

Baths

2,335

Sq.Ft.

1725 CAROLLEE LANE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 726/720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6402984
$1,185,999
6

Beds

4.0

Baths

2,282

Sq.Ft.

726/720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1981 BLUE RIDGE ROAD Winter Park, FL MLS# O6402961
  • Virtual Tour
1 of 52
$1,150,000
4

Beds

2.0

Baths

2,750

Sq.Ft.

1981 BLUE RIDGE ROAD

Winter Park, FL

View 2111 MALLARD CIRCLE Winter Park, FL MLS# O6401350
  • Virtual Tour
1 of 28
$1,245,000
4

Beds

3.0

Baths

2,667

Sq.Ft.

2111 MALLARD CIRCLE

Winter Park, FL

View 363 N PHELPS AVENUE Winter Park, FL MLS# O6401811
  • Virtual Tour
1 of 36
$1,249,000
4

Beds

3.0

Baths

2,871

Sq.Ft.

363 N PHELPS AVENUE

Winter Park, FL

View 2702 PARKLAND DRIVE Winter Park, FL MLS# O6397997
  • Virtual Tour
1 of 48
$1,139,750
5

Beds

3.0

Baths

2,656

Sq.Ft.

2702 PARKLAND DRIVE

Winter Park, FL

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

404

Estimated median home price

$742,000
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 3
$100K - 200K 48
$200K - 300K 25
$300K - 400K 20
$400K - 500K 33
$500K - 600K 30
$600K - 700K 34
$700K - 800K 19
$800K - 900K 13
$900K - 1M 9
$1M - Max 170

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 258
Townhouse 16
Condo 94
Commercial 7
Rental 71
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/30/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 7/1/2026.