374 total properties
Did you mean the neighborhood Winter Park?
View 1813 HARLAND PARK DRIVE Winter Park, FL MLS# O6403483
  • Recently Listed
1 of 56
OPEN HOUSE: Saturday 5/2 2:00 PM - 4:00 PM
$1,995,000
4

Beds

3.1

Baths

3,551

Sq.Ft.

1813 HARLAND PARK DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 3371 RIVER VIEW WAY 46 Winter Park, FL MLS# O6403947
  • Recently Listed
1 of 45
OPEN HOUSE: Saturday 5/2 1:00 PM - 3:00 PM
$205,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

3371 RIVER VIEW WAY 46

Winter Park, FL

Courtesy of REALTY ONE GROUP EVOLVE
View 450 LAKEWOOD DRIVE Winter Park, FL MLS# O6403490
  • Recently Listed with Virtual Tour
1 of 77
OPEN HOUSE: Saturday 5/2 12:00 PM - 3:00 PM
$2,500,000
5

Beds

4.2

Baths

4,572

Sq.Ft.

450 LAKEWOOD DRIVE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 1864 GRINNELL TERRACE Winter Park, FL MLS# O6403822
  • Recently Listed
1 of 43
$1,599,000
5

Beds

3.1

Baths

3,028

Sq.Ft.

1864 GRINNELL TERRACE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 2237 WOODCREST DRIVE Winter Park, FL MLS# O6404115
$490,000
3

Beds

2.0

Baths

1,492

Sq.Ft.

2237 WOODCREST DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1611 CHESTNUT AVENUE Winter Park, FL MLS# O6402502
  • Recently Listed with Virtual Tour
1 of 45
OPEN HOUSE: Friday 5/1 4:00 PM - 6:00 PM
$1,100,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

1611 CHESTNUT AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1550 NORFOLK AVENUE Winter Park, FL MLS# O6402927
  • Recently Listed with Virtual Tour
1 of 29
OPEN HOUSE: Saturday 5/2 1:00 PM - 3:00 PM
$725,000
3

Beds

2.0

Baths

1,762

Sq.Ft.

1550 NORFOLK AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 688 BRECHIN DRIVE Winter Park, FL MLS# O6403080
  • Recently Listed with Virtual Tour
1 of 31
OPEN HOUSE: Saturday 5/2 11:00 AM - 1:00 PM
$724,900
4

Beds

2.0

Baths

1,599

Sq.Ft.

688 BRECHIN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 1437 MILLER AVENUE Winter Park, FL MLS# O6403858
$750,000
5

Beds

4.0

Baths

2,150

Sq.Ft.

1437 MILLER AVENUE

Winter Park, FL

Courtesy of ORLANDO REAL ESTATE LLC
View 3282 OAK LAKE PLACE 3282 Winter Park, FL MLS# O6403912
  • Recently Listed with Virtual Tour
1 of 27
$169,500
2

Beds

1.1

Baths

990

Sq.Ft.

3282 OAK LAKE PLACE 3282

Winter Park, FL

Courtesy of BUSBY REALTY LLC
View 1821 PINETREE ROAD Winter Park, FL MLS# O6395725
  • Recently Listed with Virtual Tour
1 of 63
OPEN HOUSE: Saturday 5/2 12:00 PM - 2:00 PM
$6,997,000
5

Beds

6.1

Baths

5,006

Sq.Ft.

1821 PINETREE ROAD

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1077 MINNESOTA AVENUE Winter Park, FL MLS# O6403223
  • Recently Listed with Virtual Tour
1 of 54
OPEN HOUSE: Saturday 5/2 12:00 PM - 3:00 PM
$1,625,000
4

Beds

4.0

Baths

3,046

Sq.Ft.

1077 MINNESOTA AVENUE

Winter Park, FL

Courtesy of SHAHRAM SONDI + CO.
View 4947 N PALM AVENUE Winter Park, FL MLS# O6403459
  • Recently Listed with Virtual Tour
1 of 27
$550,000
1,088

Sq.Ft.

4947 N PALM AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 3053 GEORGE MASON AVENUE 8A Winter Park, FL MLS# O6402957
  • Recently Listed with Virtual Tour
1 of 29
$75,000
1

Beds

1.0

Baths

809

Sq.Ft.

3053 GEORGE MASON AVENUE 8A

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1780 BRYAN AVENUE Winter Park, FL MLS# O6402643
  • Recently Listed with Virtual Tour
1 of 8
$849,000
Studio

Beds

0.0

Baths

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 525 OLOLU DRIVE Winter Park, FL MLS# S5148431
  • Recently Listed
1 of 42
$515,000
3

Beds

3.0

Baths

1,786

Sq.Ft.

525 OLOLU DRIVE

Winter Park, FL

Courtesy of CAISSA REALTY INVESTMENT INC
View 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
  • Recently Listed with Virtual Tour
1 of 25
$250,000
3

Beds

2.1

Baths

1,578

Sq.Ft.

7484 CANFORD COURT 8

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1660 WALNUT AVENUE Winter Park, FL MLS# O6395277
  • Recently Listed with Virtual Tour
1 of 43
$1,650,000
4

Beds

3.1

Baths

2,249

Sq.Ft.

1660 WALNUT AVENUE

Winter Park, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1725 CAROLLEE LANE Winter Park, FL MLS# O6402656
  • Recently Listed with Virtual Tour
1 of 41
OPEN HOUSE: Saturday 5/2 2:00 PM - 4:00 PM
$1,015,000
3

Beds

2.0

Baths

2,335

Sq.Ft.

1725 CAROLLEE LANE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1900 WINTER PARK ROAD Winter Park, FL MLS# O6402566
  • Recently Listed with Virtual Tour
1 of 22
$941,000
4

Beds

2.0

Baths

1,511

Sq.Ft.

1900 WINTER PARK ROAD

Winter Park, FL

Courtesy of RE/MAX ASSURED

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

370

Estimated median home price

$784,500
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 4
$100K - 200K 49
$200K - 300K 22
$300K - 400K 19
$400K - 500K 28
$500K - 600K 19
$600K - 700K 27
$700K - 800K 20
$800K - 900K 10
$900K - 1M 10
$1M - Max 162

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 227
Townhouse 16
Condo 87
Commercial 5
Rental 96
Lots and Land 27
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/1/2026)

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 5/1/2026.

The data relating to real estate on this web site comes in part from the Internet Data Exchange (IDX) program of The Fort Lauderdale Board of Realtors. Real estate listings held by firms other than Weichert Realtors, include the Listing Broker’s Firm Name.

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 5/1/2026.

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 5/1/2026.

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 5/1/2026.