325 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 616 BRECHIN DRIVE Winter Park, FL MLS# O6409911
  • Virtual Tour
1 of 44
$999,000
4

Beds

4.1

Baths

2,638

Sq.Ft.

616 BRECHIN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1138 S PENNSYLVANIA AVENUE Winter Park, FL MLS# O6420090
$999,000
3

Beds

3.0

Baths

2,434

Sq.Ft.

1138 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 471 HOLT AVENUE Winter Park, FL MLS# O6437590
  • Recently Listed with Virtual Tour
1 of 27
$995,999
4

Beds

3.0

Baths

2,528

Sq.Ft.

471 HOLT AVENUE

Winter Park, FL

Courtesy of FLORIDA HOME TEAM REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1611 CHESTNUT AVENUE Winter Park, FL MLS# O6402502
  • Virtual Tour
1 of 51
OPEN HOUSE: Sunday 9/6 2:00 PM - 4:00 PM
$995,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

1611 CHESTNUT AVENUE

Winter Park, FL

View 269 E CANTON AVENUE 269 Winter Park, FL MLS# O6404706
  • Virtual Tour
1 of 44
OPEN HOUSE: Sunday 9/6 12:00 PM - 2:00 PM
$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 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
$975,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

View 1800 MAGNOLIA AVENUE Winter Park, FL MLS# NS1087637
$950,000
4

Beds

2.1

Baths

2,431

Sq.Ft.

1800 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
  • Virtual Tour
1 of 7
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • New Construction with Virtual Tour
1 of 9
$918,000
4

Beds

2.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 29
$899,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1405 MILLER AVENUE Winter Park, FL MLS# O6386405
  • Virtual Tour
1 of 46
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1405 MILLER AVENUE

Winter Park, FL

View 1621 CHESTNUT AVENUE Winter Park, FL MLS# O6435086
  • Recently Listed with Virtual Tour
1 of 35
$899,000
3

Beds

2.1

Baths

2,022

Sq.Ft.

1621 CHESTNUT AVENUE

Winter Park, FL

View 437 N CAPEN AVENUE Winter Park, FL MLS# O6414283
  • Virtual Tour
1 of 36
$849,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

437 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 724 MONMOUTH WAY Winter Park, FL MLS# O6424409
  • Virtual Tour
1 of 36
$848,900
5

Beds

3.1

Baths

2,832

Sq.Ft.

724 MONMOUTH WAY

Winter Park, FL

View 338 BLUE HERON DRIVE Winter Park, FL MLS# O6410174
  • Virtual Tour
1 of 44
$840,000
3

Beds

3.0

Baths

2,017

Sq.Ft.

338 BLUE HERON DRIVE

Winter Park, FL

View 1507 GOLFSIDE DRIVE Winter Park, FL MLS# O6395355
  • Virtual Tour
1 of 42
$830,000
3

Beds

2.0

Baths

2,003

Sq.Ft.

1507 GOLFSIDE DRIVE

Winter Park, FL

View 1431 PALM AVENUE Winter Park, FL MLS# O6433195
  • Virtual Tour
1 of 38
OPEN HOUSE: Sunday 9/6 10:00 AM - 12:00 PM
$825,000
2

Beds

2.0

Baths

1,540

Sq.Ft.

1431 PALM AVENUE

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 1927 ELAND AVENUE Winter Park, FL MLS# O6381009
  • Virtual Tour
1 of 68
$820,000
5

Beds

3.0

Baths

2,242

Sq.Ft.

1927 ELAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
  • Virtual Tour
1 of 38
$810,000
3

Beds

3.1

Baths

2,030

Sq.Ft.

1265 ARLINGTON PL

Winter Park, FL

View 1278 S PENNSYLVANIA AVENUE 13 Winter Park, FL MLS# O6417455
  • Recently Listed with Virtual Tour
1 of 16
$799,000
3

Beds

2.1

Baths

1,957

Sq.Ft.

1278 S PENNSYLVANIA AVENUE 13

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. 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

358

Estimated median home price

$705,000
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 39
$200K - 300K 22
$300K - 400K 15
$400K - 500K 37
$500K - 600K 27
$600K - 700K 36
$700K - 800K 11
$800K - 900K 10
$900K - 1M 10
$1M - Max 148

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 218
Townhouse 21
Condo 77
Commercial 9
Rental 78
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 9/5/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

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

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being 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.

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 9/6/2026.