42 total properties
Did you mean the neighborhood Winter Park?
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6369571
  • Recently Listed with Virtual Tour
1 of 19
$499,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1518 PINEWOOD DRIVE Winter Park, FL MLS# O6369600
  • Recently Listed with Virtual Tour
1 of 18
$499,900
3

Beds

2.0

Baths

1,197

Sq.Ft.

1518 PINEWOOD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
  • Recently Listed with Virtual Tour
1 of 7
$499,000
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 824 GARRETT COURT Winter Park, FL MLS# O6368324
  • Recently Listed with Virtual Tour
1 of 35
$449,000
4

Beds

2.0

Baths

1,738

Sq.Ft.

824 GARRETT COURT

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 640 N PARK AVENUE 5 Winter Park, FL MLS# O6367841
  • Recently Listed with Virtual Tour
1 of 28
$450,000
1

Beds

1.0

Baths

673

Sq.Ft.

640 N PARK AVENUE 5

Winter Park, FL

Courtesy of PARK TOWN REAL ESTATE LLC
View 2350 CADY WAY Winter Park, FL MLS# O6367536
  • Recently Listed with Virtual Tour
1 of 31
$575,000
4

Beds

2.0

Baths

1,854

Sq.Ft.

2350 CADY WAY

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2835 BONGART ROAD Winter Park, FL MLS# O6367949
$439,900
3

Beds

3.0

Baths

1,880

Sq.Ft.

2835 BONGART ROAD

Winter Park, FL

Courtesy of FUTURE HOME REALTY INC
View 1347 ORCHID AVENUE Winter Park, FL MLS# S5140042
$449,900
4

Beds

2.0

Baths

1,490

Sq.Ft.

1347 ORCHID AVENUE

Winter Park, FL

Courtesy of SHELDON PROFESSIONALS INC
View 2042 YORKSHIRE DRIVE Winter Park, FL MLS# O6366830
$499,000
Studio

Beds

0.0

Baths

2042 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1817 JESSICA COURT Winter Park, FL MLS# O6364894
$525,000
3

Beds

2.0

Baths

1,870

Sq.Ft.

1817 JESSICA COURT

Winter Park, FL

Courtesy of KELLY PRICE & COMPANY LLC
View 875 W LYMAN AVENUE Winter Park, FL MLS# O6363961
$475,000
2

Beds

2.0

Baths

760

Sq.Ft.

875 W LYMAN AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1909 EDWIN BOULEVARD Winter Park, FL MLS# O6362682
$440,000
3

Beds

2.0

Baths

1,355

Sq.Ft.

1909 EDWIN BOULEVARD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 714 DENTON ROAD Winter Park, FL MLS# O6362464
  • Virtual Tour
1 of 32
$449,900
3

Beds

3.0

Baths

1,786

Sq.Ft.

714 DENTON ROAD

Winter Park, FL

Courtesy of COLONIALTOWN REALTY
View 2743 MERRIE OAKS ROAD Winter Park, FL MLS# O6361079
$439,000
3

Beds

2.0

Baths

1,661

Sq.Ft.

2743 MERRIE OAKS ROAD

Winter Park, FL

Courtesy of ONE45 REALTY LLC
View 2042 YORKSHIRE DRIVE Winter Park, FL MLS# O6359841
$499,000
3

Beds

2.0

Baths

1,573

Sq.Ft.

2042 YORKSHIRE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 422 S RANGER BOULEVARD Winter Park, FL MLS# O6359171
$520,000
4

Beds

2.0

Baths

1,680

Sq.Ft.

422 S RANGER BOULEVARD

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 443 S LAKEMONT AVENUE Winter Park, FL MLS# O6356128
$450,000
3

Beds

2.0

Baths

1,364

Sq.Ft.

443 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of MILLER GRANT AND COMPANY
View 2412 MIDDLETON AVENUE Winter Park, FL MLS# O6356193
$549,000
3

Beds

2.0

Baths

1,340

Sq.Ft.

2412 MIDDLETON AVENUE

Winter Park, FL

Courtesy of REAL ESTATE INVESTMENTS BY BOR
View 7502 WAUNAQUA DRIVE Winter Park, FL MLS# O6355169
$567,000
5

Beds

3.0

Baths

2,615

Sq.Ft.

7502 WAUNAQUA DRIVE

Winter Park, FL

Courtesy of REALTY TECH INC
View 1651 N PARK AVENUE Winter Park, FL MLS# O6354776
$505,000
3

Beds

2.0

Baths

1,263

Sq.Ft.

1651 N PARK AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE

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

$649,900
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

PriceCount
$0 - 100K6
$100K - 200K40
$200K - 300K22
$300K - 400K20
$400K - 500K27
$500K - 600K26
$600K - 700K21
$700K - 800K22
$800K - 900K5
$900K - 1M11
$1M - Max100

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family174
Townhouse19
Condo78
Commercial5
Rental109
Lots and Land19
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 12/30/2025)

Information deemed reliable but not guaranteed.

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 12/30/2025.

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 12/30/2025.