320 total properties
Did you mean the neighborhood Winter Park?
View 1781 INDIANA AVENUE A Winter Park, FL MLS# O6381195
  • Recently Listed with Virtual Tour
1 of 47
$575,000
3

Beds

2.1

Baths

1,616

Sq.Ft.

1781 INDIANA AVENUE A

Winter Park, FL

Courtesy of CARLISLE REALTY, LLC
View 2036 VIA TUSCANY Winter Park, FL MLS# O6379888
  • Recently Listed
1 of 19
$2,000,000
3

Beds

2.0

Baths

2,148

Sq.Ft.

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 40 PALMER AVENUE Winter Park, FL MLS# O6380444
  • Recently Listed
1 of 13
$6,950,000
5

Beds

5.1

Baths

5,905

Sq.Ft.

40 PALMER AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 3204 NETHERWOOD Winter Park, FL MLS# O6380637
  • Recently Listed with Virtual Tour
1 of 35
$324,000
2

Beds

1.1

Baths

1,056

Sq.Ft.

3204 NETHERWOOD

Winter Park, FL

Courtesy of WATSON REALTY CORP.
View 2036 VIA TUSCANY Winter Park, FL MLS# O6380892
  • Recently Listed
1 of 6
$2,000,000
Studio

Beds

0.0

Baths

2036 VIA TUSCANY

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 2012 LOCH BERRY ROAD Winter Park, FL MLS# O6381093
  • Recently Listed with Virtual Tour
1 of 10
$2,699,000
5

Beds

4.1

Baths

3,800

Sq.Ft.

2012 LOCH BERRY ROAD

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 184 SANDLEWOOD TRAIL #2 Winter Park, FL MLS# O6380753
  • Recently Listed with Virtual Tour
1 of 30
$329,000
2

Beds

2.1

Baths

1,133

Sq.Ft.

184 SANDLEWOOD TRAIL #2

Winter Park, FL

Courtesy of NOELKE REALTY
View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6380457
  • Recently Listed
1 of 24
OPEN HOUSE: Sunday 2/22 2:00 PM - 4:00 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
$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
View 675 OVERSPIN DRIVE Winter Park, FL MLS# O6378975
  • Recently Listed with Virtual Tour
1 of 32
$800,000
4

Beds

3.1

Baths

3,062

Sq.Ft.

675 OVERSPIN DRIVE

Winter Park, FL

Courtesy of WEMERT GROUP REALTY LLC
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 151 OAKWOOD WAY Winter Park, FL MLS# O6380037
  • Recently Listed
1 of 75
$3,180,000
4

Beds

4.1

Baths

4,129

Sq.Ft.

151 OAKWOOD WAY

Winter Park, FL

Courtesy of CORCORAN PREMIER REALTY
View 234 DETMAR DRIVE Winter Park, FL MLS# O6379927
  • Recently Listed with Virtual Tour
1 of 45
$1,695,000
5

Beds

5.1

Baths

3,609

Sq.Ft.

234 DETMAR DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2412 CHANTILLY AVENUE Winter Park, FL MLS# O6381552
  • Recently Listed
1 of 4
OPEN HOUSE: Saturday 2/21 1:00 PM - 3:00 PM
$2,395,000
5

Beds

6.1

Baths

4,506

Sq.Ft.

2412 CHANTILLY AVENUE

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 2501 LAFAYETTE AVENUE Winter Park, FL MLS# O6381988
  • Recently Listed
1 of 3
$1,950,000
4

Beds

4.0

Baths

2,810

Sq.Ft.

2501 LAFAYETTE AVENUE

Winter Park, FL

Courtesy of REAL BROKER, 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 1000 S SEMORAN BOULEVARD S Winter Park, FL MLS# O6379459
  • Recently Listed with Virtual Tour
1 of 11
$128,500
2

Beds

2.0

Baths

1,072

Sq.Ft.

1000 S SEMORAN BOULEVARD S

Winter Park, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
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

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

320

Estimated median home price

$700,500
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 6
$100K - 200K 36
$200K - 300K 32
$300K - 400K 20
$400K - 500K 25
$500K - 600K 18
$600K - 700K 23
$700K - 800K 20
$800K - 900K 7
$900K - 1M 7
$1M - Max 126

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 180
Townhouse 18
Condo 85
Commercial 5
Rental 86
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 2/20/2026)

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 2/20/2026.

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 2/20/2026.

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 2/20/2026.