374 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 40 PALMER AVENUE Winter Park, FL MLS# O6380444
  • New Construction
1 of 21
$7,250,000
5

Beds

5.1

Baths

5,905

Sq.Ft.

40 PALMER AVENUE

Winter Park, FL

View 1260 ALABAMA DRIVE Winter Park, FL MLS# O6387200
$6,900,000
6

Beds

5.2

Baths

6,396

Sq.Ft.

1260 ALABAMA DRIVE

Winter Park, FL

View 2661 Via Tuscany Winter Park, FL MLS# B26030158
  • New Construction with Virtual Tour
1 of 44
$6,888,888
4

Beds

4.1

Baths

4,636

Sq.Ft.

2661 Via Tuscany

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1571 WOODLAND AVENUE Winter Park, FL MLS# O6411706
  • Virtual Tour
1 of 75
$6,000,000
5

Beds

6.2

Baths

7,397

Sq.Ft.

1571 WOODLAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2228 AZALEA PLACE Winter Park, FL MLS# O6416342
  • Virtual Tour
1 of 72
$5,600,000
5

Beds

5.1

Baths

5,152

Sq.Ft.

2228 AZALEA PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 313 SYLVAN DRIVE Winter Park, FL MLS# O6407606
  • New Construction with Virtual Tour
1 of 10
$5,500,000
4

Beds

4.1

Baths

4,775

Sq.Ft.

313 SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2025 SUMMERLAND AVENUE Winter Park, FL MLS# O6426204
$5,295,000
5

Beds

4.1

Baths

4,432

Sq.Ft.

2025 SUMMERLAND AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2211 Azalea Place Winter Park, FL MLS# A11824988
  • Adult Community with Virtual Tour
1 of 394
$5,250,000
5

Beds

6.1

Baths

7,278

Sq.Ft.

2211 Azalea Place

Winter Park, FL

View 231 CHELTON CIRCLE Winter Park, FL MLS# O6414890
  • Virtual Tour
1 of 67
$4,950,000
4

Beds

5.2

Baths

5,550

Sq.Ft.

231 CHELTON CIRCLE

Winter Park, FL

View 1180 VIA LUGANO Winter Park, FL MLS# O6413198
  • Virtual Tour
1 of 67
$4,900,000
5

Beds

5.1

Baths

4,961

Sq.Ft.

1180 VIA LUGANO

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2525 TEMPLE DRIVE Winter Park, FL MLS# O6427787
  • Virtual Tour
1 of 51
$4,750,000
5

Beds

4.1

Baths

4,542

Sq.Ft.

2525 TEMPLE DRIVE

Winter Park, FL

View 857 BROCK STREET Winter Park, FL MLS# O6432219
  • New Construction with Virtual Tour
1 of 11
$4,650,000
5

Beds

5.1

Baths

4,827

Sq.Ft.

857 BROCK STREET

Winter Park, FL

View 540 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6431538
$4,600,000
Studio

Beds

0.0

Baths

540 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1525 GRANVILLE DRIVE Winter Park, FL MLS# O6422951
  • New Construction with Virtual Tour
1 of 56
$4,595,000
5

Beds

5.1

Baths

5,211

Sq.Ft.

1525 GRANVILLE DRIVE

Winter Park, FL

View 503 N INTERLACHEN AVENUE Winter Park, FL MLS# O6331207
$4,500,000
Studio

Beds

0.0

Baths

503 N INTERLACHEN AVENUE

Winter Park, FL

View 702 VIA BELLA Winter Park, FL MLS# O6437125
  • Virtual Tour
1 of 41
$4,400,000
4

Beds

5.1

Baths

3,720

Sq.Ft.

702 VIA BELLA

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2403 EUSTON ROAD Winter Park, FL MLS# O6434678
  • Recently Listed with Virtual Tour
1 of 11
$4,299,000
Studio

Beds

0.0

Baths

2403 EUSTON ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 229 ALEXANDER PLACE Winter Park, FL MLS# O6412911
  • Virtual Tour
1 of 53
$4,250,000
4

Beds

4.2

Baths

4,431

Sq.Ft.

229 ALEXANDER PLACE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1417 WILLIAMS DRIVE Winter Park, FL MLS# O6428414
  • New Construction with Virtual Tour
1 of 55
$3,999,000
5

Beds

5.1

Baths

4,891

Sq.Ft.

1417 WILLIAMS DRIVE

Winter Park, FL

View 1441 CARDINAL COURT Winter Park, FL MLS# O6399395
  • Virtual Tour
1 of 85
$3,995,000
4

Beds

5.1

Baths

4,066

Sq.Ft.

1441 CARDINAL COURT

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

374

Estimated median home price

$697,250
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 41
$200K - 300K 23
$300K - 400K 13
$400K - 500K 39
$500K - 600K 31
$600K - 700K 37
$700K - 800K 11
$800K - 900K 11
$900K - 1M 9
$1M - Max 155

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 229
Townhouse 24
Condo 80
Commercial 9
Rental 78
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 9/1/2026)

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 9/1/2026.