306 total properties
Did you mean the neighborhood Winter Park?
View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6380457
  • Recently Listed
1 of 24
OPEN HOUSE: Saturday 2/7 11:00 AM - 1:00 PM
$1,249,000
3

Beds

2.0

Baths

1,907

Sq.Ft.

1836 GRINNELL TERRACE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 106 S INTERLACHEN AVENUE 118 Winter Park, FL MLS# O6380506
  • Recently Listed
1 of 55
OPEN HOUSE: Saturday 2/7 11:00 AM - 1:00 PM
$1,495,000
3

Beds

2.0

Baths

1,834

Sq.Ft.

106 S INTERLACHEN AVENUE 118

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 764 W COMSTOCK AVENUE Winter Park, FL MLS# O6379596
  • Recently Listed with Virtual Tour
1 of 39
$474,000
2

Beds

1.0

Baths

925

Sq.Ft.

764 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 600 W WEBSTER AVENUE Winter Park, FL MLS# O6378330
  • Recently Listed
1 of 5
$295,000
2

Beds

1.0

Baths

754

Sq.Ft.

600 W WEBSTER AVENUE

Winter Park, FL

Courtesy of REALTY ONE GROUP MVP
View 1500 GAY ROAD 5 Winter Park, FL MLS# S5143213
  • Recently Listed with Virtual Tour
1 of 17
$195,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 5

Winter Park, FL

Courtesy of TRANSCEND REALTY
View 1137 OAKS BOULEVARD Winter Park, FL MLS# O6379388
  • Recently Listed
1 of 29
$644,900
2

Beds

1.1

Baths

1,149

Sq.Ft.

1137 OAKS BOULEVARD

Winter Park, FL

Courtesy of RE/MAX 200 REALTY
View 2748 LION HEART ROAD Winter Park, FL MLS# O6379237
  • Recently Listed with Virtual Tour
1 of 49
OPEN HOUSE: Saturday 2/7 12:00 PM - 3:00 PM
$500,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

2748 LION HEART ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 151 OAKWOOD WAY Winter Park, FL MLS# O6380037
  • Recently Listed
1 of 75
OPEN HOUSE: Saturday 2/7 12:00 PM - 3:00 PM
$3,180,000
4

Beds

4.1

Baths

4,129

Sq.Ft.

151 OAKWOOD WAY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 4872 ORANGE AVENUE Winter Park, FL MLS# O6380333
  • Recently Listed with Virtual Tour
1 of 18
$375,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

4872 ORANGE AVENUE

Winter Park, FL

Courtesy of ALFA REAL ESTATE LLC
View 1113 VIA DEL MAR Winter Park, FL MLS# O6379697
  • Recently Listed with 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 831/833 HUNTINGTON COURT Winter Park, FL MLS# O6378801
  • Recently Listed with Virtual Tour
1 of 43
$1,100,000
6

Beds

4.0

Baths

2,915

Sq.Ft.

831/833 HUNTINGTON COURT

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1742 TEMPLE DRIVE Winter Park, FL MLS# O6378905
  • Recently Listed with Virtual Tour
1 of 73
$3,549,995
4

Beds

5.0

Baths

3,658

Sq.Ft.

1742 TEMPLE DRIVE

Winter Park, FL

Courtesy of ROI AVE LLC
View 2015 N PARK AVENUE Winter Park, FL MLS# O6372603
  • Recently Listed with Virtual Tour
1 of 62
$2,495,000
5

Beds

4.1

Baths

3,963

Sq.Ft.

2015 N PARK AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 200 SAINT ANDREWS BOULEVARD 2302 Winter Park, FL MLS# O6377760
  • Recently Listed with Virtual Tour
1 of 18
$195,000
2

Beds

2.0

Baths

987

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2302

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1860 STAUNTON AVENUE Winter Park, FL MLS# O6378554
  • Recently Listed with Virtual Tour
1 of 10
$1,195,000
4

Beds

3.1

Baths

2,525

Sq.Ft.

1860 STAUNTON AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1564 CAVENDISH ROAD Winter Park, FL MLS# O6380505
$470,000
2

Beds

1.0

Baths

1,140

Sq.Ft.

1564 CAVENDISH ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 100 S INTERLACHEN AVENUE 404 Winter Park, FL MLS# O6375851
  • Recently Listed
1 of 36
OPEN HOUSE: Sunday 2/8 2:00 PM - 4:00 PM
$1,165,000
2

Beds

2.0

Baths

1,220

Sq.Ft.

100 S INTERLACHEN AVENUE 404

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 501 DARCEY DRIVE Winter Park, FL MLS# O6378578
  • Recently Listed with Virtual Tour
1 of 39
$1,675,000
5

Beds

4.1

Baths

3,033

Sq.Ft.

501 DARCEY DRIVE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 2600 EUSTON ROAD Winter Park, FL MLS# O6380534
$650,000
6

Beds

3.0

Baths

3,145

Sq.Ft.

2600 EUSTON ROAD

Winter Park, FL

Courtesy of YOUNG REAL ESTATE
View 147 S INTERLACHEN AVENUE 202 Winter Park, FL MLS# L4959060
  • Recently Listed with Virtual Tour
1 of 31
$2,695,000
3

Beds

4.1

Baths

3,272

Sq.Ft.

147 S INTERLACHEN AVENUE 202

Winter Park, FL

Courtesy of HELLOSOLD 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

300

Estimated median home price

$687,500
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 7
$100K - 200K 34
$200K - 300K 29
$300K - 400K 16
$400K - 500K 26
$500K - 600K 18
$600K - 700K 25
$700K - 800K 18
$800K - 900K 5
$900K - 1M 8
$1M - Max 114

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 170
Townhouse 17
Condo 78
Commercial 6
Rental 91
Lots and Land 21
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 2/6/2026)

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 2/7/2026.

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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 2/7/2026.

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 2/7/2026.