330 total properties
Did you mean the neighborhood Winter Park?
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 2700 CADY WAY Winter Park, FL MLS# O6347690
  • Recently Listed
1 of 49
$649,000
4

Beds

2.0

Baths

1,876

Sq.Ft.

2700 CADY WAY

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1037 N VIRGINIA AVENUE Winter Park, FL MLS# O6419694
  • Recently Listed with Virtual Tour
1 of 35
$649,000
3

Beds

1.0

Baths

1,101

Sq.Ft.

1037 N VIRGINIA AVENUE

Winter Park, FL

View 1037 N VIRGINIA AVENUE Winter Park, FL MLS# O6419696
  • Recently Listed
1 of 18
$649,000
Studio

Beds

0.0

Baths

1037 N VIRGINIA AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
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 1926 NATALEN ROAD Winter Park, FL MLS# O6388308
  • Virtual Tour
1 of 44
$638,900
3

Beds

2.0

Baths

1,469

Sq.Ft.

1926 NATALEN ROAD

Winter Park, FL

Courtesy of JAMIESON PROPERTIES, INC.
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5137596
  • Virtual Tour
1 of 30
$630,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2612 ROXBURY ROAD Winter Park, FL MLS# S5139410
  • Virtual Tour
1 of 37
$630,000
5

Beds

3.0

Baths

2,472

Sq.Ft.

2612 ROXBURY ROAD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2600 EUSTON ROAD Winter Park, FL MLS# O6397890
  • Virtual Tour
1 of 36
$630,000
6

Beds

3.0

Baths

3,145

Sq.Ft.

2600 EUSTON ROAD

Winter Park, FL

Courtesy of AROD PARTNERS REALTY
View 685 OVERSPIN DRIVE Winter Park, FL MLS# O6415537
$629,000
3

Beds

2.1

Baths

2,112

Sq.Ft.

685 OVERSPIN DRIVE

Winter Park, FL

View 1830 EDWIN BOULEVARD Winter Park, FL MLS# O6400055
  • Virtual Tour
1 of 48
$625,000
3

Beds

2.0

Baths

1,287

Sq.Ft.

1830 EDWIN BOULEVARD

Winter Park, FL

View 2652 ABBEY ROAD Winter Park, FL MLS# O6419026
  • Recently Listed with 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 2708 LION HEART ROAD Winter Park, FL MLS# O6387685
  • Virtual Tour
1 of 47
$617,500
3

Beds

2.0

Baths

1,785

Sq.Ft.

2708 LION HEART ROAD

Winter Park, FL

View 661 SELKIRK DRIVE Winter Park, FL MLS# O6354700
  • Virtual Tour
1 of 19
$600,000
3

Beds

2.1

Baths

2,150

Sq.Ft.

661 SELKIRK DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS HERITAGE REALTY
View 1821 KILLARNEY DRIVE Winter Park, FL MLS# O6410660
$599,999
Studio

Beds

0.0

Baths

1821 KILLARNEY DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 2758 BANCHORY ROAD Winter Park, FL MLS# O6329628
  • Virtual Tour
1 of 37
$598,000
3

Beds

2.1

Baths

1,539

Sq.Ft.

2758 BANCHORY ROAD

Winter Park, FL

Courtesy of MR VARGAS PROPERTY MANAGEMENT LLC
View 1822 YORKSHIRE DRIVE Winter Park, FL MLS# O6401364
  • Virtual Tour
1 of 42
$598,000
3

Beds

3.0

Baths

1,620

Sq.Ft.

1822 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
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 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 508 DUNRAVEN DRIVE Winter Park, FL MLS# O6412363
$595,000
3

Beds

2.0

Baths

1,370

Sq.Ft.

508 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
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

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

405

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 3
$100K - 200K 46
$200K - 300K 26
$300K - 400K 20
$400K - 500K 32
$500K - 600K 31
$600K - 700K 34
$700K - 800K 19
$800K - 900K 13
$900K - 1M 9
$1M - Max 172

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 260
Townhouse 17
Condo 92
Commercial 7
Rental 70
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/29/2026)

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 6/29/2026.

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 6/29/2026.

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 6/29/2026.