399 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 1500 GAY ROAD 17D Winter Park, FL MLS# O6408516
  • Recently Listed with Virtual Tour
1 of 36
$259,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 17D

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 2973 SANBINA STREET Winter Park, FL MLS# O6407521
  • Recently Listed with Virtual Tour
1 of 36
$377,880
3

Beds

2.0

Baths

1,128

Sq.Ft.

2973 SANBINA STREET

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 2661 Via Tuscany Winter Park, FL MLS# B26030158
  • Recently Listed 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 2430 CHANTILLY AVENUE Winter Park, FL MLS# O6401352
  • Recently Listed with Virtual Tour
1 of 49
$1,665,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

2430 CHANTILLY AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 643 N PARK AVENUE Winter Park, FL MLS# O6403591
  • Recently Listed with Virtual Tour
1 of 82
$4,295,000
3

Beds

3.2

Baths

4,231

Sq.Ft.

643 N PARK AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1407 MILLER AVENUE Winter Park, FL MLS# O6406408
  • Recently Listed with Virtual Tour
1 of 44
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1407 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 926 ENCLAVE PLACE Winter Park, FL MLS# O6408030
  • Recently Listed
1 of 3
$2,235,000
5

Beds

4.1

Baths

4,150

Sq.Ft.

926 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 505 CORNWALL ROAD Winter Park, FL MLS# O6408759
  • Recently Listed with Virtual Tour
1 of 42
OPEN HOUSE: Sunday 5/31 12:00 PM - 2:00 PM
$675,000
4

Beds

2.0

Baths

1,813

Sq.Ft.

505 CORNWALL ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2228 HOWARD DRIVE Winter Park, FL MLS# O6407733
  • Recently Listed with Virtual Tour
1 of 9
$2,460,000
4

Beds

3.1

Baths

3,294

Sq.Ft.

2228 HOWARD DRIVE

Winter Park, FL

Courtesy of COLEDEV REAL ESTATE LLC
View 910 ENCLAVE PLACE Winter Park, FL MLS# O6406803
$1,899,000
5

Beds

4.1

Baths

3,620

Sq.Ft.

910 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 930 ENCLAVE PLACE Winter Park, FL MLS# O6403032
  • Recently Listed
1 of 4
$2,050,000
5

Beds

4.1

Baths

3,813

Sq.Ft.

930 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
  • Recently Listed with Virtual Tour
1 of 23
$399,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

Courtesy of JC FLORIDA REALTY LLC
View 2215 WOODCREST DRIVE Winter Park, FL MLS# O6407540
  • Recently Listed
1 of 39
$719,000
4

Beds

2.0

Baths

1,688

Sq.Ft.

2215 WOODCREST DRIVE

Winter Park, FL

Courtesy of ADAIR REALTY INC
View 340 KILLARNEY BAY COURT 4-4 Winter Park, FL MLS# O6407259
  • Recently Listed with Virtual Tour
1 of 37
OPEN HOUSE: Sunday 5/31 12:00 PM - 3:00 PM
$395,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

340 KILLARNEY BAY COURT 4-4

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
  • Recently Listed with Virtual Tour
1 of 33
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE 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 1600 S PENNSYLVANIA AVENUE Winter Park, FL MLS# NS1088189
  • Recently Listed with Virtual Tour
1 of 49
$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
  • Recently Listed with Virtual Tour
1 of 49
$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
View 1420 MAGNOLIA AVENUE Winter Park, FL MLS# O6404564
  • Recently Listed with Virtual Tour
1 of 67
OPEN HOUSE: Sunday 5/31 2:00 PM - 4:00 PM
$1,750,000
4

Beds

3.1

Baths

3,174

Sq.Ft.

1420 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 627 DUNBLANE DRIVE Winter Park, FL MLS# O6405036
  • Recently Listed with Virtual Tour
1 of 36
$899,000
4

Beds

3.0

Baths

2,086

Sq.Ft.

627 DUNBLANE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK

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

398

Estimated median home price

$797,500
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 3
$100K - 200K 45
$200K - 300K 24
$300K - 400K 26
$400K - 500K 29
$500K - 600K 22
$600K - 700K 30
$700K - 800K 21
$800K - 900K 14
$900K - 1M 10
$1M - Max 174

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 260
Townhouse 13
Condo 86
Commercial 7
Rental 78
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/30/2026)

Information deemed reliable but not guaranteed.

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 5/31/2026.

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 5/31/2026.

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 5/31/2026.

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.

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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 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 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 5/31/2026.