280 total properties
Did you mean the neighborhood 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 240 N PHELPS AVENUE Winter Park, FL MLS# O6415360
  • New Construction with Virtual Tour
1 of 44
OPEN HOUSE: Saturday 10/31 1:00 PM - 3:00 PM
$1,999,900
5

Beds

4.1

Baths

2,889

Sq.Ft.

240 N PHELPS AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 2614 PARKLAND DRIVE Winter Park, FL MLS# O6444165
  • Virtual Tour
1 of 54
$1,890,000
4

Beds

3.1

Baths

3,307

Sq.Ft.

2614 PARKLAND DRIVE

Winter Park, FL

Courtesy of JW GASTON LLC
View 751 PANSY AVENUE Winter Park, FL MLS# O6432554
  • Virtual Tour
1 of 44
$1,875,000
3

Beds

3.1

Baths

2,703

Sq.Ft.

751 PANSY AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 281 BREWER AVENUE Winter Park, FL MLS# O6424364
  • Virtual Tour
1 of 46
$1,800,000
5

Beds

4.1

Baths

4,029

Sq.Ft.

281 BREWER AVENUE

Winter Park, FL

Courtesy of HENTHORN REAL ESTATE
View 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6416565
  • New Construction with Virtual Tour
1 of 22
$1,795,000
4

Beds

4.0

Baths

2,819

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 922 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6424685
$1,795,000
4

Beds

4.0

Baths

3,440

Sq.Ft.

922 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 101 S NEW YORK AVENUE 311 Winter Park, FL MLS# O6416927
$1,775,000
3

Beds

3.1

Baths

3,112

Sq.Ft.

101 S NEW YORK AVENUE 311

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 1840 ANZLE AVENUE Winter Park, FL MLS# O6374102
  • New Construction with Virtual Tour
1 of 12
$1,750,000
4

Beds

2.1

Baths

2,350

Sq.Ft.

1840 ANZLE AVENUE

Winter Park, FL

Courtesy of B LIVE COMMERCIAL AND RESIDENT
View 1225 SHARON PLACE Winter Park, FL MLS# O6443546
  • Virtual Tour
1 of 78
$1,749,000
5

Beds

3.1

Baths

3,097

Sq.Ft.

1225 SHARON PLACE

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 1840 BRYAN AVENUE Winter Park, FL MLS# O6431360
  • Virtual Tour
1 of 53
$1,725,000
4

Beds

3.1

Baths

3,727

Sq.Ft.

1840 BRYAN AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 1641 HIBISCUS AVENUE Winter Park, FL MLS# O6453343
$1,725,000
4

Beds

3.2

Baths

3,594

Sq.Ft.

1641 HIBISCUS AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2613 LAFAYETTE AVENUE Winter Park, FL MLS# O6447662
  • New Construction with Virtual Tour
1 of 24
$1,699,900
4

Beds

3.1

Baths

2,661

Sq.Ft.

2613 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 2308 MULBRY DRIVE Winter Park, FL MLS# O6432803
  • New Construction with Virtual Tour
1 of 12
$1,699,000
4

Beds

3.1

Baths

2,530

Sq.Ft.

2308 MULBRY DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2343 VERSAILLES AVENUE Winter Park, FL MLS# O6432029
$1,699,000
4

Beds

3.1

Baths

3,307

Sq.Ft.

2343 VERSAILLES AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1420 MAGNOLIA AVENUE Winter Park, FL MLS# O6404564
  • Virtual Tour
1 of 67
$1,690,000
4

Beds

3.1

Baths

3,174

Sq.Ft.

1420 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. 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

351

Estimated median home price

$775,000
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 20
$300K - 400K 16
$400K - 500K 32
$500K - 600K 24
$600K - 700K 36
$700K - 800K 16
$800K - 900K 13
$900K - 1M 14
$1M - Max 143

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 207
Townhouse 22
Condo 76
Commercial 15
Rental 87
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 10/28/2026)

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 10/29/2026.

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 10/29/2026.