229 total properties
Did you mean the neighborhood Winter Park?
View 321 SYLVAN BOULEVARD Winter Park, FL MLS# O6417674
$1,395,000
3

Beds

2.1

Baths

2,821

Sq.Ft.

321 SYLVAN BOULEVARD

Winter Park, FL

View 501 LAKEVIEW AVENUE Winter Park, FL MLS# O6325192
  • New Construction with Virtual Tour
1 of 59
$1,390,000
4

Beds

4.1

Baths

3,253

Sq.Ft.

501 LAKEVIEW AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1751 GOODRICH AVENUE Winter Park, FL MLS# O6377936
$1,380,000
4

Beds

3.1

Baths

2,170

Sq.Ft.

1751 GOODRICH AVENUE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 420 OHIO STREET Winter Park, FL MLS# O6399541
  • New Construction with Virtual Tour
1 of 8
$1,360,000
5

Beds

5.1

Baths

3,735

Sq.Ft.

420 OHIO STREET

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1881 LAKE SPIER DRIVE Winter Park, FL MLS# O6396357
$1,350,000
3

Beds

2.0

Baths

1,750

Sq.Ft.

1881 LAKE SPIER DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 1881 LAKE SPIER DRIVE Winter Park, FL MLS# O6396791
$1,350,000
Studio

Beds

0.0

Baths

1881 LAKE SPIER DRIVE

Winter Park, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 802 HAMILTON PLACE COURT Winter Park, FL MLS# O6398373
$1,324,000
4

Beds

3.1

Baths

2,843

Sq.Ft.

802 HAMILTON PLACE COURT

Winter Park, FL

Courtesy of FLORIDA CAPITAL REALTY
View 1649 HARMON AVENUE Winter Park, FL MLS# O6392216
  • Virtual Tour
1 of 57
$1,299,900
4

Beds

3.1

Baths

3,223

Sq.Ft.

1649 HARMON AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 100 S INTERLACHEN AVENUE 101 Winter Park, FL MLS# O6382597
$1,299,000
3

Beds

2.0

Baths

1,734

Sq.Ft.

100 S INTERLACHEN AVENUE 101

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1870 STAUNTON AVENUE Winter Park, FL MLS# O6391469
  • New Construction with Virtual Tour
1 of 10
$1,250,000
4

Beds

3.1

Baths

2,525

Sq.Ft.

1870 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1600 ALABAMA DRIVE 402 Winter Park, FL MLS# O6413153
$1,250,000
2

Beds

2.0

Baths

1,574

Sq.Ft.

1600 ALABAMA DRIVE 402

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View Address not provided Winter Park, FL MLS# O6406381
  • New Construction with Virtual Tour
1 of 25
$1,249,900
4

Beds

3.1

Baths

2,936

Sq.Ft.

Address not provided

Winter Park, FL

View 363 N PHELPS AVENUE Winter Park, FL MLS# O6401811
  • Virtual Tour
1 of 36
$1,249,000
4

Beds

3.0

Baths

2,871

Sq.Ft.

363 N PHELPS AVENUE

Winter Park, FL

View 3006 NORTHWOOD BOULEVARD Winter Park, FL MLS# O6419056
  • Recently Listed with Virtual Tour
1 of 46
$1,249,000
4

Beds

3.0

Baths

2,075

Sq.Ft.

3006 NORTHWOOD BOULEVARD

Winter Park, FL

View 1870 WALKER AVENUE Winter Park, FL MLS# O6390504
  • New Construction with Virtual Tour
1 of 32
$1,225,000
3

Beds

2.1

Baths

2,046

Sq.Ft.

1870 WALKER AVENUE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2111 MALLARD CIRCLE Winter Park, FL MLS# O6401350
  • Virtual Tour
1 of 28
$1,199,000
4

Beds

3.0

Baths

2,667

Sq.Ft.

2111 MALLARD CIRCLE

Winter Park, FL

View 1500 HARRIS CIRCLE Winter Park, FL MLS# O6379012
  • Virtual Tour
1 of 27
$1,195,000
2

Beds

3.0

Baths

2,096

Sq.Ft.

1500 HARRIS CIRCLE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 726/720 N PENNSYLVANIA AVENUE Winter Park, FL MLS# O6402984
$1,185,999
6

Beds

4.0

Baths

2,282

Sq.Ft.

726/720 N PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1981 BLUE RIDGE ROAD Winter Park, FL MLS# O6402961
  • Virtual Tour
1 of 52
$1,150,000
4

Beds

2.0

Baths

2,750

Sq.Ft.

1981 BLUE RIDGE ROAD

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1404 BORDER DRIVE Winter Park, FL MLS# O6412140
  • Virtual Tour
1 of 38
$1,150,000
4

Beds

4.0

Baths

2,469

Sq.Ft.

1404 BORDER DRIVE

Winter Park, FL

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

306

Estimated median home price

$735,000
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 4
$100K - 200K 41
$200K - 300K 18
$300K - 400K 14
$400K - 500K 25
$500K - 600K 21
$600K - 700K 24
$700K - 800K 11
$800K - 900K 11
$900K - 1M 5
$1M - Max 132

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 186
Townhouse 14
Condo 73
Commercial 7
Rental 72
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/10/2026)

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 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 7/11/2026.

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 7/11/2026.