264 total properties
Did you mean the neighborhood Winter Park?
View 1016 HOWELL BRANCH ROAD Winter Park, FL MLS# O6386288
  • Recently Listed with Virtual Tour
1 of 64
$1,699,000
4

Beds

3.0

Baths

3,142

Sq.Ft.

1016 HOWELL BRANCH ROAD

Winter Park, FL

Courtesy of PLAID PROPERTIES, LLC
View 234 DETMAR DRIVE Winter Park, FL MLS# O6379927
  • Virtual Tour
1 of 45
OPEN HOUSE: Sunday 3/22 2:00 PM - 4:00 PM
$1,695,000
5

Beds

5.1

Baths

3,609

Sq.Ft.

234 DETMAR DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 629 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6386610
  • Recently Listed with Virtual Tour
1 of 46
OPEN HOUSE: Saturday 3/21 1:00 PM - 4:00 PM
$1,695,000
4

Beds

3.1

Baths

3,031

Sq.Ft.

629 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of CLASSIC HOMES
The time to sell is now! THE TIME TO SELL IS NOW!
View 1810 HOLLYWOOD AVENUE Winter Park, FL MLS# O6377320
  • New Construction with Virtual Tour
1 of 10
$1,689,000
4

Beds

3.1

Baths

2,604

Sq.Ft.

1810 HOLLYWOOD AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 446 ALBERTA DRIVE Winter Park, FL MLS# O6319233
  • Virtual Tour
1 of 69
$1,675,000
4

Beds

2.1

Baths

3,263

Sq.Ft.

446 ALBERTA DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1705 ELIZABETHS WALK Winter Park, FL MLS# O6389723
$1,650,000
5

Beds

5.0

Baths

3,820

Sq.Ft.

1705 ELIZABETHS WALK

Winter Park, FL

Courtesy of HOMEVEST REALTY
View 1510 MILLER AVENUE Winter Park, FL MLS# O6350503
  • New Construction with Virtual Tour
1 of 70
OPEN HOUSE: Saturday 3/21 12:00 PM - 4:00 PM
$1,634,900
5

Beds

4.1

Baths

3,252

Sq.Ft.

1510 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 1340 PLACE PICARDY Winter Park, FL MLS# O6382113
  • Virtual Tour
1 of 34
$1,599,000
3

Beds

3.1

Baths

3,459

Sq.Ft.

1340 PLACE PICARDY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1113 VIA DEL MAR Winter Park, FL MLS# O6379697
  • Virtual Tour
1 of 9
$1,595,000
3

Beds

2.0

Baths

2,012

Sq.Ft.

1113 VIA DEL MAR

Winter Park, FL

Courtesy of BAY HILL REALTY LLC
View 607 ELLEN DRIVE Winter Park, FL MLS# O6354269
  • New Construction with Virtual Tour
1 of 34
$1,575,000
4

Beds

3.2

Baths

2,812

Sq.Ft.

607 ELLEN DRIVE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1523 MILLER AVENUE Winter Park, FL MLS# O6371649
  • New Construction
1 of 6
$1,550,000
5

Beds

4.0

Baths

3,164

Sq.Ft.

1523 MILLER AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 507 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6377844
$1,550,000
4

Beds

3.1

Baths

2,985

Sq.Ft.

507 COUNTRY CLUB DRIVE

Winter Park, FL

Courtesy of SOTERA LIVING
View 132 BURKS CIRCLE Winter Park, FL MLS# O6354963
  • Virtual Tour
1 of 32
$1,525,000
4

Beds

4.1

Baths

3,022

Sq.Ft.

132 BURKS CIRCLE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 141 W LAKE SUE AVENUE Winter Park, FL MLS# O6345896
$1,500,000
Studio

Beds

0.0

Baths

141 W LAKE SUE AVENUE

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 246 PALMER AVENUE Winter Park, FL MLS# O6388115
  • Virtual Tour
1 of 55
$1,500,000
2

Beds

2.0

Baths

2,281

Sq.Ft.

246 PALMER AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 246 PALMER AVENUE Winter Park, FL MLS# O6388117
  • Virtual Tour
1 of 24
$1,500,000
Studio

Beds

0.0

Baths

246 PALMER AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1473 Berkshire Avenue Winter Park, FL MLS# 1048892
  • New Construction with Virtual Tour
1 of 55
OPEN HOUSE: Saturday 3/21 11:00 AM - 2:00 PM
$1,499,000
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
1 of 53
OPEN HOUSE: Saturday 3/21 11:00 AM - 2:00 PM
$1,499,000
5

Beds

4.0

Baths

2,895

Sq.Ft.

1473 BERKSHIRE AVENUE

Winter Park, FL

Courtesy of GOLDEN GROUP REALTY LLC
View 340 ALBERTA DRIVE Winter Park, FL MLS# O6345231
  • Virtual Tour
1 of 70
OPEN HOUSE: Friday 3/20 3:00 PM - 5:00 PM
$1,495,000
4

Beds

4.0

Baths

3,226

Sq.Ft.

340 ALBERTA DRIVE

Winter Park, FL

Courtesy of REAL ESTATE FIRM OF ORLANDO
View 102 BELL PLACE Winter Park, FL MLS# O6354345
  • New Construction with Virtual Tour
1 of 78
$1,479,000
4

Beds

3.1

Baths

2,459

Sq.Ft.

102 BELL PLACE

Winter Park, FL

Courtesy of INVESTOR'S REAL ESTATE 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

318

Estimated median home price

$737,350
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 42
$200K - 300K 23
$300K - 400K 16
$400K - 500K 28
$500K - 600K 14
$600K - 700K 22
$700K - 800K 17
$800K - 900K 8
$900K - 1M 9
$1M - Max 133

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 183
Townhouse 17
Condo 83
Commercial 3
Rental 87
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 3/18/2026)

Information deemed reliable but not guaranteed.

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 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 3/20/2026.

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 3/20/2026.

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 3/20/2026.

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 3/20/2026.