339 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 433 CAROLINA AVENUE Winter Park, FL MLS# O6406911
$1,395,000
5

Beds

3.1

Baths

2,771

Sq.Ft.

433 CAROLINA AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1347 CHAPMAN CIRCLE Winter Park, FL MLS# O6408189
$1,395,000
4

Beds

3.1

Baths

2,922

Sq.Ft.

1347 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of ORLANDO PROPERTY ADVISORS
View 501 LAKEVIEW AVENUE Winter Park, FL MLS# O6325192
  • New Construction with Virtual Tour
1 of 59
$1,390,000
4

Beds

4.1

Baths

3,253

Sq.Ft.

501 LAKEVIEW AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 266 W LYMAN AVENUE Winter Park, FL MLS# O6406526
$1,375,000
3

Beds

3.0

Baths

2,000

Sq.Ft.

266 W LYMAN AVENUE

Winter Park, FL

Courtesy of MAROON REALTY GROUP LLC
View 106 S INTERLACHEN AVENUE 118 Winter Park, FL MLS# O6380506
$1,360,000
3

Beds

2.0

Baths

1,834

Sq.Ft.

106 S INTERLACHEN AVENUE 118

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 420 OHIO STREET Winter Park, FL MLS# O6399541
  • New Construction with Virtual Tour
1 of 8
$1,360,000
5

Beds

5.1

Baths

3,735

Sq.Ft.

420 OHIO STREET

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1881 LAKE SPIER DRIVE Winter Park, FL MLS# O6396357
$1,350,000
3

Beds

2.0

Baths

1,750

Sq.Ft.

1881 LAKE SPIER DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 1881 LAKE SPIER DRIVE Winter Park, FL MLS# O6396791
$1,350,000
Studio

Beds

0.0

Baths

1881 LAKE SPIER DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 1649 HARMON AVENUE Winter Park, FL MLS# O6392216
  • Virtual Tour
1 of 57
$1,349,900
4

Beds

3.1

Baths

3,223

Sq.Ft.

1649 HARMON AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 802 HAMILTON PLACE COURT Winter Park, FL MLS# O6398373
$1,349,000
4

Beds

3.1

Baths

2,843

Sq.Ft.

802 HAMILTON PLACE COURT

Winter Park, FL

Courtesy of FLORIDA CAPITAL REALTY
View 100 S INTERLACHEN AVENUE 101 Winter Park, FL MLS# O6382597
$1,299,000
3

Beds

2.0

Baths

1,734

Sq.Ft.

100 S INTERLACHEN AVENUE 101

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1500 HARRIS CIRCLE Winter Park, FL MLS# O6379012
  • Virtual Tour
1 of 27
$1,295,000
2

Beds

3.0

Baths

2,096

Sq.Ft.

1500 HARRIS CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2111 MALLARD CIRCLE Winter Park, FL MLS# O6401350
  • Virtual Tour
1 of 24
$1,295,000
4

Beds

3.0

Baths

2,667

Sq.Ft.

2111 MALLARD CIRCLE

Winter Park, FL

Courtesy of BREC PROPERTIES INC
View 2465 BANCHORY ROAD Winter Park, FL MLS# O6403997
  • Recently Listed
1 of 42
$1,295,000
4

Beds

5.0

Baths

3,971

Sq.Ft.

2465 BANCHORY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 1651 WESTCHESTER AVENUE Winter Park, FL MLS# O6384358
$1,275,000
3

Beds

2.1

Baths

2,426

Sq.Ft.

1651 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of SERHANT
View 1870 STAUNTON AVENUE Winter Park, FL MLS# O6391469
  • New Construction with Virtual Tour
1 of 10
$1,250,000
4

Beds

3.1

Baths

2,525

Sq.Ft.

1870 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View Address not provided Winter Park, FL MLS# O6406381
  • Recently Listed with Virtual Tour
1 of 25
$1,249,900
4

Beds

3.1

Baths

2,936

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
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

Courtesy of CREEGAN GROUP
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

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

390

Estimated median home price

$787,500
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 2
$100K - 200K 49
$200K - 300K 23
$300K - 400K 24
$400K - 500K 29
$500K - 600K 22
$600K - 700K 29
$700K - 800K 20
$800K - 900K 16
$900K - 1M 10
$1M - Max 166

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 246
Townhouse 15
Condo 88
Commercial 7
Rental 73
Lots and Land 27
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/23/2026)

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.

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

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

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.

Data is updated as of 5/24/2026.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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.

Data is updated as of 5/24/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

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.

Data is updated as of 5/24/2026.

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.

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 5/24/2026.