337 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 4026 TENITA DRIVE Winter Park, FL MLS# O6430278
  • Virtual Tour
1 of 26
$599,000
3

Beds

2.0

Baths

2,031

Sq.Ft.

4026 TENITA DRIVE

Winter Park, FL

View 1021 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6429124
  • Recently Listed with Virtual Tour
1 of 7
$1,295,000
Studio

Beds

0.0

Baths

1021 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 531 W SWOOPE AVENUE Winter Park, FL MLS# O6430119
$635,000
2

Beds

2.0

Baths

1,188

Sq.Ft.

531 W SWOOPE AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 669 W COMSTOCK AVENUE Winter Park, FL MLS# TB8535201
$249,000
Studio

Beds

0.0

Baths

669 W COMSTOCK AVENUE

Winter Park, FL

View 645 PANSY AVENUE Winter Park, FL MLS# O6428967
  • Virtual Tour
1 of 60
$2,390,000
4

Beds

4.1

Baths

3,661

Sq.Ft.

645 PANSY AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1695 LEE ROAD A101 Winter Park, FL MLS# O6429942
  • Virtual Tour
1 of 22
$154,900
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A101

Winter Park, FL

View 351 STARLING ROAD Winter Park, FL MLS# O6429698
$499,900
3

Beds

1.1

Baths

1,979

Sq.Ft.

351 STARLING ROAD

Winter Park, FL

View 2781 ABBEY ROAD Winter Park, FL MLS# O6429991
  • Virtual Tour
1 of 29
$520,000
3

Beds

2.0

Baths

1,596

Sq.Ft.

2781 ABBEY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1061 ARAGON AVENUE 1061 Winter Park, FL MLS# S5152353
$510,000
3

Beds

2.1

Baths

1,669

Sq.Ft.

1061 ARAGON AVENUE 1061

Winter Park, FL

Courtesy of WATSON REALTY CORP
View 1871 BRYAN AVENUE Winter Park, FL MLS# O6424945
  • Virtual Tour
1 of 28
$625,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

1871 BRYAN AVENUE

Winter Park, FL

View 228 RIPPLING LANE Winter Park, FL MLS# O6429407
  • Virtual Tour
1 of 55
$540,000
3

Beds

2.0

Baths

1,618

Sq.Ft.

228 RIPPLING LANE

Winter Park, FL

View 525 S LAKEMONT AVENUE Winter Park, FL MLS# O6428654
  • New Construction with Virtual Tour
1 of 59
$1,999,990
4

Beds

3.1

Baths

3,330

Sq.Ft.

525 S LAKEMONT AVENUE

Winter Park, FL

View 1071 ARAGON AVENUE Winter Park, FL MLS# O6429215
  • Virtual Tour
1 of 34
$575,000
2

Beds

2.1

Baths

1,851

Sq.Ft.

1071 ARAGON AVENUE

Winter Park, FL

View 405 Lake Fair Lane Winter Park, FL MLS# A12062271
  • Virtual Tour
1 of 18
$434,990
3

Beds

2.0

Baths

405 Lake Fair Lane

Winter Park, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 2525 LAFAYETTE AVENUE Winter Park, FL MLS# O6428823
  • New Construction with Virtual Tour
1 of 10
$1,749,000
4

Beds

3.1

Baths

2,715

Sq.Ft.

2525 LAFAYETTE AVENUE

Winter Park, FL

View 1840 LAUREL ROAD Winter Park, FL MLS# O6428841
  • New Construction with Virtual Tour
1 of 12
$2,299,000
5

Beds

5.0

Baths

2,868

Sq.Ft.

1840 LAUREL ROAD

Winter Park, FL

View 433 GILBERT ROAD Winter Park, FL MLS# O6428430
  • Virtual Tour
1 of 36
$669,900
3

Beds

2.0

Baths

1,770

Sq.Ft.

433 GILBERT ROAD

Winter Park, FL

View 2826 AMBERGATE ROAD Winter Park, FL MLS# O6427973
  • Virtual Tour
1 of 46
$460,000
3

Beds

2.0

Baths

1,521

Sq.Ft.

2826 AMBERGATE ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1546 MILLER AVENUE Winter Park, FL MLS# O6428019
  • New Construction with Virtual Tour
1 of 36
$1,419,900
4

Beds

3.1

Baths

2,984

Sq.Ft.

1546 MILLER AVENUE

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 305 Winter Park, FL MLS# O6428044
$115,000
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 305

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

369

Estimated median home price

$699,000
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 41
$200K - 300K 22
$300K - 400K 14
$400K - 500K 38
$500K - 600K 31
$600K - 700K 37
$700K - 800K 11
$800K - 900K 11
$900K - 1M 10
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 225
Townhouse 24
Condo 78
Commercial 9
Rental 76
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 9/3/2026)

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 9/3/2026.