29 total properties
Did you mean the neighborhood Winter Park?
View 814 DENSMORE DR Winter Park, FL MLS# O6399773
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1 of 24
$425,000
4

Beds

2.0

Baths

1,610

Sq.Ft.

814 DENSMORE DR

Winter Park, FL

View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
$349,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

View 3054 BLUEBROOK DRIVE Winter Park, FL MLS# O6398450
$389,500
3

Beds

2.0

Baths

1,939

Sq.Ft.

3054 BLUEBROOK DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
$460,000
3

Beds

2.0

Baths

1,606

Sq.Ft.

950 HANOVER AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
$444,900
3

Beds

2.0

Baths

1,491

Sq.Ft.

405 LAKE FAIR LANE

Winter Park, FL

View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$458,000
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

View Address not provided Winter Park, FL MLS# S5145631
$430,000
4

Beds

2.0

Baths

1,296

Sq.Ft.

Address not provided

Winter Park, FL

View 958 DUPONT AVENUE Winter Park, FL MLS# O6371341
$375,000
3

Beds

2.0

Baths

1,572

Sq.Ft.

958 DUPONT AVENUE

Winter Park, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
$459,900
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY

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

367

Estimated median home price

$750,000
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

PriceCount
$0 - 100K7
$100K - 200K41
$200K - 300K23
$300K - 400K16
$400K - 500K33
$500K - 600K25
$600K - 700K32
$700K - 800K15
$800K - 900K12
$900K - 1M12
$1M - Max151

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family224
Townhouse20
Condo81
Commercial11
Rental69
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 7/31/2026)

Information deemed reliable but not guaranteed.

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 8/1/2026.