330 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 1319 BESSMOR ROAD Winter Park, FL MLS# O6400395
$589,000
3

Beds

2.0

Baths

1,126

Sq.Ft.

1319 BESSMOR ROAD

Winter Park, FL

Courtesy of GALLOWAY REAL ESTATE
View 2829 ALOMA Winter Park, FL MLS# O6404107
  • Virtual Tour
1 of 36
$579,000
4

Beds

2.0

Baths

1,821

Sq.Ft.

2829 ALOMA

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 333 CORNWALL ROAD Winter Park, FL MLS# O6409379
$579,000
4

Beds

2.0

Baths

1,660

Sq.Ft.

333 CORNWALL ROAD

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 517 ROUGHBEARD ROAD Winter Park, FL MLS# O6399029
$565,000
3

Beds

2.0

Baths

1,873

Sq.Ft.

517 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
$560,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC
View 423 OLOLU DRIVE Winter Park, FL MLS# O6369976
  • Virtual Tour
1 of 51
$549,000
3

Beds

3.0

Baths

1,920

Sq.Ft.

423 OLOLU DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1809 HAMMERLIN AVENUE Winter Park, FL MLS# O6373616
$549,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1809 HAMMERLIN AVENUE

Winter Park, FL

Courtesy of NICOLE-HUDSON REALTY CORP
View 4033 YACHT COURT Winter Park, FL MLS# O6379135
  • Virtual Tour
1 of 26
$549,000
3

Beds

2.0

Baths

2,268

Sq.Ft.

4033 YACHT COURT

Winter Park, FL

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

Beds

2.0

Baths

1,930

Sq.Ft.

4053 COOL WATER COURT

Winter Park, FL

View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
$545,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 330 ELKHORN COURT Winter Park, FL MLS# O6376757
$544,900
3

Beds

2.0

Baths

1,570

Sq.Ft.

330 ELKHORN COURT

Winter Park, FL

View 528 SAINT DUNSTAN WAY Winter Park, FL MLS# O6414677
  • Recently Listed with Virtual Tour
1 of 35
$535,000
3

Beds

2.0

Baths

1,656

Sq.Ft.

528 SAINT DUNSTAN WAY

Winter Park, FL

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
View 1261 INDIANA AVENUE Winter Park, FL MLS# O6400698
$534,900
3

Beds

2.1

Baths

1,660

Sq.Ft.

1261 INDIANA AVENUE

Winter Park, FL

View 2718 SANDWELL DRIVE Winter Park, FL MLS# O6410283
$525,000
3

Beds

2.0

Baths

1,597

Sq.Ft.

2718 SANDWELL DRIVE

Winter Park, FL

View 1745 INDIANA AVENUE J Winter Park, FL MLS# O6402920
$524,000
3

Beds

2.1

Baths

1,616

Sq.Ft.

1745 INDIANA AVENUE J

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1944 NATALEN ROAD Winter Park, FL MLS# O6405802
$519,000
3

Beds

2.0

Baths

1,380

Sq.Ft.

1944 NATALEN ROAD

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 1807 HAMMERLIN AVENUE G Winter Park, FL MLS# O6391277
$515,000
3

Beds

2.1

Baths

1,818

Sq.Ft.

1807 HAMMERLIN AVENUE G

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
$515,000
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

View 2627 AMBERGATE ROAD Winter Park, FL MLS# O6093816
$510,000
4

Beds

3.0

Baths

1,805

Sq.Ft.

2627 AMBERGATE ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY

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

404

Estimated median home price

$742,000
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

PriceCount
$0 - 100K3
$100K - 200K48
$200K - 300K25
$300K - 400K20
$400K - 500K33
$500K - 600K30
$600K - 700K34
$700K - 800K19
$800K - 900K13
$900K - 1M9
$1M - Max170

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family258
Townhouse16
Condo94
Commercial7
Rental71
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 6/30/2026)

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 6/30/2026.

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 6/30/2026.