326 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 3651 N GOLDENROD ROAD D102 Winter Park, FL MLS# O6401114
$157,900
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D102

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 446 MELROSE AVENUE Winter Park, FL MLS# O6402113
  • Virtual Tour
1 of 39
OPEN HOUSE: Sunday 6/21 2:00 PM - 4:00 PM
$1,625,000
4

Beds

2.0

Baths

2,640

Sq.Ft.

446 MELROSE AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
  • Virtual Tour
1 of 29
$534,900
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 1307 FORMOSA AVENUE Winter Park, FL MLS# O6400711
  • Virtual Tour
1 of 33
$373,800
2

Beds

1.0

Baths

1,150

Sq.Ft.

1307 FORMOSA AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 802 HAMILTON PLACE COURT Winter Park, FL MLS# O6398373
$1,324,000
4

Beds

3.1

Baths

2,843

Sq.Ft.

802 HAMILTON PLACE COURT

Winter Park, FL

Courtesy of FLORIDA CAPITAL REALTY
View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
  • Virtual Tour
1 of 13
$589,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

Courtesy of GALLOWAY REAL ESTATE
View 814 DENSMORE DR Winter Park, FL MLS# O6399773
  • Virtual Tour
1 of 24
$425,000
4

Beds

2.0

Baths

1,610

Sq.Ft.

814 DENSMORE DR

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 1741 WESTCHESTER AVENUE Winter Park, FL MLS# O6399014
$595,000
3

Beds

2.0

Baths

1,434

Sq.Ft.

1741 WESTCHESTER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
  • Virtual Tour
1 of 9
$349,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RICK SINGH REAL ESTATE
View 1830 EDWIN BOULEVARD Winter Park, FL MLS# O6400055
  • Virtual Tour
1 of 48
OPEN HOUSE: Saturday 6/20 11:00 AM - 1:00 PM
$625,000
3

Beds

2.0

Baths

1,287

Sq.Ft.

1830 EDWIN BOULEVARD

Winter Park, FL

View 927 FAIRWAY DRIVE Winter Park, FL MLS# TB8498515
  • Virtual Tour
1 of 29
$680,000
4

Beds

3.0

Baths

1,918

Sq.Ft.

927 FAIRWAY DRIVE

Winter Park, FL

Courtesy of FLAT FEE MLS REALTY
View 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6386578
  • Adult Community with Virtual Tour
1 of 29
$229,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE REALTY
View 2756 SHERIFF WAY Winter Park, FL MLS# O6402570
  • Virtual Tour
1 of 48
$595,000
3

Beds

2.0

Baths

1,812

Sq.Ft.

2756 SHERIFF WAY

Winter Park, FL

View 102 BELL PLACE Winter Park, FL MLS# O6398118
  • New Construction with Virtual Tour
1 of 46
$1,399,000
4

Beds

3.1

Baths

2,459

Sq.Ft.

102 BELL PLACE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1960 WINTER PARK ROAD Winter Park, FL MLS# O6398264
$899,000
Studio

Beds

0.0

Baths

1960 WINTER PARK ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1701 GOODRICH AVENUE Winter Park, FL MLS# O6400278
$709,000
3

Beds

2.0

Baths

1,528

Sq.Ft.

1701 GOODRICH AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1540 MILLER AVENUE Winter Park, FL MLS# O6398421
  • New Construction with Virtual Tour
1 of 55
$1,399,900
4

Beds

3.1

Baths

2,984

Sq.Ft.

1540 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 1618 INDIANA AVENUE Winter Park, FL MLS# O6398673
  • Virtual Tour
1 of 31
$675,000
4

Beds

2.0

Baths

1,604

Sq.Ft.

1618 INDIANA AVENUE

Winter Park, FL

Courtesy of NATIONAL REAL ESTATE
View 1565 FOREST AVENUE Winter Park, FL MLS# O6398694
  • Virtual Tour
1 of 37
OPEN HOUSE: Saturday 6/20 3:00 PM - 5:00 PM
$1,495,000
4

Beds

2.0

Baths

2,163

Sq.Ft.

1565 FOREST AVENUE

Winter Park, FL

Courtesy of NORDQUIST & COMPANY INC
View 3054 BLUEBROOK DRIVE Winter Park, FL MLS# O6398450
  • Virtual Tour
1 of 27
$410,000
3

Beds

2.0

Baths

1,939

Sq.Ft.

3054 BLUEBROOK DRIVE

Winter Park, FL

Courtesy of WEATHERSPOON REALTY INC

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

399

Estimated median home price

$799,000
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 2
$100K - 200K 43
$200K - 300K 24
$300K - 400K 23
$400K - 500K 29
$500K - 600K 31
$600K - 700K 30
$700K - 800K 19
$800K - 900K 14
$900K - 1M 9
$1M - Max 175

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 262
Townhouse 15
Condo 86
Commercial 7
Rental 71
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/19/2026)

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 6/19/2026.

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 6/19/2026.

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 6/19/2026.