363 total properties
Did you mean the neighborhood Winter Park?
View 2234 HOWARD DRIVE Winter Park, FL MLS# O6441596
  • Recently Listed with Virtual Tour
1 of 17
$2,295,000
4

Beds

5.1

Baths

3,295

Sq.Ft.

2234 HOWARD DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 930 ENCLAVE PLACE Winter Park, FL MLS# O6403032
  • New Construction with Virtual Tour
1 of 16
$2,275,000
5

Beds

4.1

Baths

3,813

Sq.Ft.

930 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 1885 TEMPLE DRIVE Winter Park, FL MLS# O6359471
  • Virtual Tour
1 of 59
$2,195,000
5

Beds

3.1

Baths

3,691

Sq.Ft.

1885 TEMPLE DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1271 PALMER AVENUE Winter Park, FL MLS# O6441038
  • Virtual Tour
1 of 61
$2,195,000
4

Beds

4.1

Baths

2,850

Sq.Ft.

1271 PALMER AVENUE

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 304 SANTIAGO DRIVE Winter Park, FL MLS# O6447782
  • Virtual Tour
1 of 58
$2,195,000
5

Beds

4.1

Baths

4,213

Sq.Ft.

304 SANTIAGO DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1803 Barker Drive Winter Park, FL MLS# 1087618
$2,190,000
4

Beds

3.0

Baths

3,463

Sq.Ft.

1803 Barker Drive

Winter Park, FL

Brevard
View 1803 BARKER DRIVE Winter Park, FL MLS# O6442064
  • Virtual Tour
1 of 45
$2,190,000
4

Beds

3.0

Baths

3,463

Sq.Ft.

1803 BARKER DRIVE

Winter Park, FL

Courtesy of DENOVO REALTY
View 918 ENCLAVE PLACE Winter Park, FL MLS# O6439116
  • Recently Listed
1 of 8
$2,125,000
5

Beds

4.1

Baths

3,713

Sq.Ft.

918 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2036 VIA TUSCANY Winter Park, FL MLS# O6448788
  • Recently Listed
1 of 14
$2,100,000
0.0

Baths

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1355 HIBISCUS AVENUE Winter Park, FL MLS# O6450044
$2,100,000
5

Beds

5.1

Baths

4,155

Sq.Ft.

1355 HIBISCUS AVENUE

Winter Park, FL

Courtesy of PALMANO GROUP RE BROKERAGE LLC
View 555 E LAKE SUE AVENUE Winter Park, FL MLS# O6442775
$2,095,000
4

Beds

4.0

Baths

3,776

Sq.Ft.

555 E LAKE SUE AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1951 WINTER PARK ROAD Winter Park, FL MLS# O6441816
$2,089,000
4

Beds

3.1

Baths

3,479

Sq.Ft.

1951 WINTER PARK ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 914 ENCLAVE PLACE Winter Park, FL MLS# O6391825
  • New Construction
1 of 3
$2,070,000
5

Beds

4.1

Baths

3,617

Sq.Ft.

914 ENCLAVE PLACE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 240 N PHELPS AVENUE Winter Park, FL MLS# O6415360
  • New Construction with Virtual Tour
1 of 44
$2,050,000
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 525 S LAKEMONT AVENUE Winter Park, FL MLS# O6428654
  • New Construction with Virtual Tour
1 of 59
$1,999,990
4

Beds

3.1

Baths

3,330

Sq.Ft.

525 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1415 GROVE TERRACE Winter Park, FL MLS# O6423553
  • Virtual Tour
1 of 20
$1,995,000
0.0

Baths

1415 GROVE TERRACE

Winter Park, FL

Courtesy of GOLDEN GROUP REALTY LLC
View 2007 EDWIN BOULEVARD Winter Park, FL MLS# O6439783
  • New Construction
1 of 4
$1,995,000
4

Beds

3.1

Baths

3,314

Sq.Ft.

2007 EDWIN BOULEVARD

Winter Park, FL

Courtesy of DREAM FINDERS REALTY GROUP CORP
View 3075 N GOLDENROD ROAD Winter Park, FL MLS# O6426621
$1,950,000
4,687

Sq.Ft.

3075 N GOLDENROD ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 513 DUNRAVEN DRIVE Winter Park, FL MLS# O6444889
$1,950,000
5

Beds

4.1

Baths

3,560

Sq.Ft.

513 DUNRAVEN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2260 MULBRY DRIVE Winter Park, FL MLS# O6441026
  • New Construction with Virtual Tour
1 of 12
$1,925,000
5

Beds

4.0

Baths

3,246

Sq.Ft.

2260 MULBRY DRIVE

Winter Park, FL

Courtesy of KONA REALTY SERVICES 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

361

Estimated median home price

$769,000
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 34
$200K - 300K 22
$300K - 400K 21
$400K - 500K 30
$500K - 600K 28
$600K - 700K 34
$700K - 800K 17
$800K - 900K 14
$900K - 1M 14
$1M - Max 144

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 214
Townhouse 20
Condo 78
Commercial 15
Rental 85
Lots and Land 25
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/20/2026)

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 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 10/20/2026.

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.

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 10/20/2026.