238 total properties
Did you mean the neighborhood Winter Park?
View 1780 MIZELL AVENUE Winter Park, FL MLS# O6361633
  • New Construction
1 of 44
$1,595,000
4

Beds

4.0

Baths

2,743

Sq.Ft.

1780 MIZELL AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1473 Berkshire Avenue Winter Park, FL MLS# 1048892
  • New Construction with Virtual Tour
1 of 55
$1,589,904
5

Beds

4.0

Baths

2,895

Sq.Ft.

1473 Berkshire Avenue

Winter Park, FL

Brevard
View 1473 BERKSHIRE AVENUE Winter Park, FL MLS# O6320741
  • New Construction with Virtual Tour
1 of 53
$1,589,904
5

Beds

4.0

Baths

2,895

Sq.Ft.

1473 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of GOLDEN GROUP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1408 CHAPMAN CIRCLE Winter Park, FL MLS# O6357486
  • Virtual Tour
1 of 57
$1,525,000
4

Beds

4.0

Baths

3,237

Sq.Ft.

1408 CHAPMAN CIRCLE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 102 BELL PLACE Winter Park, FL MLS# O6354345
  • New Construction with Virtual Tour
1 of 51
$1,499,000
4

Beds

3.1

Baths

2,459

Sq.Ft.

102 BELL PLACE

Winter Park, FL

Courtesy of INVESTOR'S REAL ESTATE LLC
View 1807 YORKSHIRE DRIVE Winter Park, FL MLS# TB8451098
  • New Construction
1 of 3
$1,450,000
4

Beds

4.1

Baths

3,565

Sq.Ft.

1807 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of WEEKLEY HOMES REALTY COMPANY
View 1540 MILLER AVENUE Winter Park, FL MLS# O6350580
  • New Construction
1 of 4
$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 525 LAKEVIEW AVENUE Winter Park, FL MLS# O6325165
  • New Construction with Virtual Tour
1 of 7
$1,390,000
4

Beds

4.1

Baths

3,253

Sq.Ft.

525 LAKEVIEW AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 501 LAKEVIEW AVENUE Winter Park, FL MLS# O6325192
  • New Construction with Virtual Tour
1 of 7
$1,390,000
4

Beds

4.1

Baths

3,253

Sq.Ft.

501 LAKEVIEW AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 2015 SUMMERFIELD ROAD Winter Park, FL MLS# O6357615
  • New Construction with Virtual Tour
1 of 50
OPEN HOUSE: Saturday 1/3 12:00 PM - 3:00 PM
$1,375,000
4

Beds

4.0

Baths

3,024

Sq.Ft.

2015 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 952 MOSS LANE Winter Park, FL MLS# TB8388549
  • Virtual Tour
1 of 55
$1,369,950
4

Beds

2.2

Baths

3,474

Sq.Ft.

952 MOSS LANE

Winter Park, FL

Courtesy of THE SHOP REAL ESTATE CO.
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 1673 MAYFIELD AVENUE Winter Park, FL MLS# O6369267
  • Recently Listed with Virtual Tour
1 of 44
$1,300,000
4

Beds

4.0

Baths

2,540

Sq.Ft.

1673 MAYFIELD AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. 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
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
  • 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

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

291

Estimated median home price

$650,000
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 39
$200K - 300K 22
$300K - 400K 18
$400K - 500K 26
$500K - 600K 23
$600K - 700K 21
$700K - 800K 21
$800K - 900K 4
$900K - 1M 11
$1M - Max 100

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 168
Townhouse 19
Condo 75
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 12/31/2025)

Information deemed reliable but not guaranteed.

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Data is updated as of 1/1/2026.

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 1/1/2026.

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 1/1/2026.

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 1/1/2026.