337 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 259 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6419225
  • Recently Listed with Virtual Tour
1 of 26
$465,500
3

Beds

2.0

Baths

1,248

Sq.Ft.

259 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
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 981 ARAGON AVENUE Winter Park, FL MLS# O6420093
  • Recently Listed with Virtual Tour
1 of 7
$535,000
2

Beds

1.0

Baths

857

Sq.Ft.

981 ARAGON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2249 MINNESOTA AVENUE Winter Park, FL MLS# O6419820
  • Recently Listed with Virtual Tour
1 of 81
$429,900
4

Beds

2.0

Baths

1,536

Sq.Ft.

2249 MINNESOTA AVENUE

Winter Park, FL

View 2774 BANCHORY ROAD Winter Park, FL MLS# O6418821
  • Recently Listed
1 of 34
$645,000
3

Beds

2.0

Baths

1,560

Sq.Ft.

2774 BANCHORY ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1003 LAKE BELL DRIVE Winter Park, FL MLS# O6418278
$649,900
3

Beds

2.0

Baths

1,837

Sq.Ft.

1003 LAKE BELL DRIVE

Winter Park, FL

View JESSICA COURT Winter Park, FL MLS# O6419256
  • Recently Listed with Virtual Tour
1 of 11
$449,000
Studio

Beds

0.0

Baths

JESSICA COURT

Winter Park, FL

View 751 WARRENTON ROAD Winter Park, FL MLS# TB8522073
  • Recently Listed with Virtual Tour
1 of 16
$319,900
3

Beds

2.0

Baths

1,196

Sq.Ft.

751 WARRENTON ROAD

Winter Park, FL

View 1826 BANCHORY ROAD Winter Park, FL MLS# O6419474
$779,000
4

Beds

2.1

Baths

2,391

Sq.Ft.

1826 BANCHORY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View Address not provided Winter Park, FL MLS# O6419422
  • Recently Listed
1 of 34
$229,900
2

Beds

1.1

Baths

1,219

Sq.Ft.

Address not provided

Winter Park, FL

View 2652 ABBEY ROAD Winter Park, FL MLS# O6419026
  • Virtual Tour
1 of 44
$625,000
5

Beds

2.0

Baths

1,938

Sq.Ft.

2652 ABBEY ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 7488 WHISPERWOOD DRIVE 28 Winter Park, FL MLS# O6419151
  • Recently Listed with Virtual Tour
1 of 64
$230,000
2

Beds

2.1

Baths

1,578

Sq.Ft.

7488 WHISPERWOOD DRIVE 28

Winter Park, FL

View 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
  • Recently Listed with Virtual Tour
1 of 46
$1,300,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

View 2344 WOODCREST DRIVE Winter Park, FL MLS# O6418782
  • Recently Listed with Virtual Tour
1 of 22
$729,900
4

Beds

2.0

Baths

1,764

Sq.Ft.

2344 WOODCREST DRIVE

Winter Park, FL

View 2625 PARK PLACE DRIVE Winter Park, FL MLS# O6413031
  • Recently Listed with Virtual Tour
1 of 55
$1,950,000
4

Beds

4.1

Baths

3,460

Sq.Ft.

2625 PARK PLACE DRIVE

Winter Park, FL

View 332 FLEET ROAD Winter Park, FL MLS# O6414829
  • Virtual Tour
1 of 35
$595,000
4

Beds

2.0

Baths

2,355

Sq.Ft.

332 FLEET ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Recently Listed with Virtual Tour
1 of 26
$250,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

View 512 W SWOOPE AVENUE Winter Park, FL MLS# O6417375
  • Recently Listed with Virtual Tour
1 of 46
$1,399,000
3

Beds

2.1

Baths

2,585

Sq.Ft.

512 W SWOOPE AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 4053 COOL WATER COURT Winter Park, FL MLS# O6419831
  • Recently Listed
1 of 41
$549,000
3

Beds

2.0

Baths

1,930

Sq.Ft.

4053 COOL WATER COURT

Winter Park, FL

View 2361 ROXBURY ROAD Winter Park, FL MLS# O6418164
  • Recently Listed with Virtual Tour
1 of 34
$599,000
3

Beds

2.0

Baths

1,723

Sq.Ft.

2361 ROXBURY ROAD

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

394

Estimated median home price

$750,000
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 4
$100K - 200K 46
$200K - 300K 26
$300K - 400K 19
$400K - 500K 30
$500K - 600K 29
$600K - 700K 34
$700K - 800K 17
$800K - 900K 13
$900K - 1M 9
$1M - Max 167

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 249
Townhouse 17
Condo 92
Commercial 7
Rental 69
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/3/2026)

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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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.

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 7/3/2026.

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

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 7/3/2026.