301 total properties
Did you mean the neighborhood Winter Park?
View 1429 CHAPMAN CIRCLE Winter Park, FL MLS# O6257912
  • Virtual Tour
1 of 36
$1,349,950
4

Beds

4.0

Baths

3,116

Sq.Ft.

1429 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 800 HAMILTON PLACE COURT Winter Park, FL MLS# O6321816
$1,295,000
3

Beds

3.1

Baths

3,363

Sq.Ft.

800 HAMILTON PLACE COURT

Winter Park, FL

Courtesy of EPIC REAL ESTATE ADVISORS LLC
View 1400 S PENNSYLVANIA AVENUE Winter Park, FL MLS# TB8344918
$1,250,000
4

Beds

3.0

Baths

2,310

Sq.Ft.

1400 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of JACK KELLER INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 501 W CANTON AVENUE Winter Park, FL MLS# O6344716
  • Virtual Tour
1 of 29
$1,225,000
3

Beds

2.1

Baths

2,372

Sq.Ft.

501 W CANTON AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 726 and 720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6281793
$1,215,000
6

Beds

4.0

Baths

2,284

Sq.Ft.

726 and 720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 726/720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6282473
$1,215,000
6

Beds

4.0

Baths

2,284

Sq.Ft.

726/720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 1600 PALMER AVENUE Winter Park, FL MLS# O6361587
  • Recently Listed with Virtual Tour
1 of 49
$1,200,000
3

Beds

2.1

Baths

2,550

Sq.Ft.

1600 PALMER AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1981 BLUE RIDGE ROAD Winter Park, FL MLS# O6337890
  • Virtual Tour
1 of 51
$1,199,900
4

Beds

2.0

Baths

2,750

Sq.Ft.

1981 BLUE RIDGE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1822 GREENWICH AVENUE Winter Park, FL MLS# A4669605
$1,199,900
3

Beds

2.0

Baths

1,627

Sq.Ft.

1822 GREENWICH AVENUE

Winter Park, FL

Courtesy of FLATFEE.COM
View 100 S INTERLACHEN AVENUE 404 Winter Park, FL MLS# O6330566
$1,195,000
2

Beds

2.0

Baths

1,220

Sq.Ft.

100 S INTERLACHEN AVENUE 404

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 100 S INTERLACHEN AVENUE 415 Winter Park, FL MLS# O6354679
$1,195,000
2

Beds

2.0

Baths

1,267

Sq.Ft.

100 S INTERLACHEN AVENUE 415

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1150 KENWOOD AVENUE Winter Park, FL MLS# O6355666
  • Virtual Tour
1 of 41
$1,190,000
3

Beds

2.1

Baths

2,557

Sq.Ft.

1150 KENWOOD AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 503 W CANTON AVENUE Winter Park, FL MLS# O6367552
  • Recently Listed with Virtual Tour
1 of 37
$1,157,000
3

Beds

2.1

Baths

2,342

Sq.Ft.

503 W CANTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1611 WALNUT AVENUE Winter Park, FL MLS# O6365438
  • Virtual Tour
1 of 41
$1,150,000
4

Beds

3.0

Baths

2,635

Sq.Ft.

1611 WALNUT AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 240 E Lake Sue Ave Winter Park, FL MLS# F10537698
  • Virtual Tour
1 of 15
$1,107,750
2

Beds

2.0

Baths

1,329

Sq.Ft.

240 E Lake Sue Ave

Winter Park, FL

View 2607 LAFAYETTE AVENUE Winter Park, FL MLS# O6314734
$1,095,000
4

Beds

3.1

Baths

2,770

Sq.Ft.

2607 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of FORTUNE INTERNATIONAL REALTY
View 2607 Lafayette Ave Winter Park, FL MLS# A11826269
  • Virtual Tour
1 of 71
$1,095,000
4

Beds

3.1

Baths

2,770

Sq.Ft.

2607 Lafayette Ave

Winter Park, FL

Courtesy of FORTUNE CHRISTIE'S INTERNATIONAL REAL ESTATE
View 632 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6250417
$1,050,000
3

Beds

2.0

Baths

2,342

Sq.Ft.

632 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 2260 HAWICK LANE Winter Park, FL MLS# O6343603
  • Virtual Tour
1 of 5
$995,000
Studio

Beds

0.0

Baths

2260 HAWICK LANE

Winter Park, FL

Courtesy of DAVEN REAL ESTATE INC
View 913 MOSS LANE Winter Park, FL MLS# O6307671
  • Virtual Tour
1 of 38
$975,000
3

Beds

2.0

Baths

1,887

Sq.Ft.

913 MOSS LANE

Winter Park, FL

Courtesy of VECTOR 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

301

Estimated median home price

$639,000
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 6
$100K - 200K 40
$200K - 300K 21
$300K - 400K 19
$400K - 500K 32
$500K - 600K 26
$600K - 700K 21
$700K - 800K 22
$800K - 900K 5
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 176
Townhouse 19
Condo 77
Commercial 5
Rental 108
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 12/28/2025)

Information deemed reliable but not guaranteed.

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Data is updated as of 12/29/2025.

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Data is updated as of 12/29/2025.

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 12/29/2025.

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 12/29/2025.