197 total properties
Did you mean the neighborhood Winter Park?
View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
$495,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 958 HANOVER AVENUE Winter Park, FL MLS# O6388088
$490,000
4

Beds

3.0

Baths

1,378

Sq.Ft.

958 HANOVER AVENUE

Winter Park, FL

Courtesy of AGILE GROUP 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 3601 MIDIRON DRIVE Winter Park, FL MLS# O6368849
$489,000
Studio

Beds

0.0

Baths

3601 MIDIRON DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 3207 LOWNDES DRIVE Winter Park, FL MLS# O6362285
$485,000
3

Beds

2.0

Baths

2,028

Sq.Ft.

3207 LOWNDES DRIVE

Winter Park, FL

Courtesy of MILLER GRANT AND COMPANY
View 1010 GARDEN DRIVE Winter Park, FL MLS# O6400287
$485,000
Studio

Beds

0.0

Baths

1010 GARDEN DRIVE

Winter Park, FL

Courtesy of WATSON REALTY CORP.
View 240 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6330690
$480,000
4

Beds

2.0

Baths

1,718

Sq.Ft.

240 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of A+ REALTY PROFESSIONALS, INC
View 501 HERITAGE BOULEVARD Winter Park, FL MLS# S5145746
$479,900
4

Beds

2.0

Baths

1,376

Sq.Ft.

501 HERITAGE BOULEVARD

Winter Park, FL

Courtesy of EXP REALTY LLC
View 346 S RANGER BOULEVARD Winter Park, FL MLS# S5134662
$475,000
3

Beds

2.0

Baths

1,592

Sq.Ft.

346 S RANGER BOULEVARD

Winter Park, FL

Courtesy of IMPERIAL REALTY OF FLORIDA INC
View 950 HANOVER AVENUE Winter Park, FL MLS# O6398273
    1 of 28
    OPEN HOUSE: Saturday 5/23 1:00 PM - 4:00 PM
    $470,000
    3

    Beds

    2.0

    Baths

    1,606

    Sq.Ft.

    950 HANOVER AVENUE

    Winter Park, FL

    Courtesy of COMPASS FLORIDA LLC
    View 7618 WAUNATTA COURT Winter Park, FL MLS# V4946886
    $457,000
    3

    Beds

    3.0

    Baths

    1,970

    Sq.Ft.

    7618 WAUNATTA COURT

    Winter Park, FL

    Courtesy of PHOENIX REALTY ADVISORS LLC
    View 405 LAKE FAIR LANE Winter Park, FL MLS# O6393594
    • Virtual Tour
    1 of 45
    OPEN HOUSE: Saturday 5/23 11:00 AM - 2:00 PM
    $455,000
    3

    Beds

    2.0

    Baths

    1,491

    Sq.Ft.

    405 LAKE FAIR LANE

    Winter Park, FL

    Courtesy of EXP REALTY LLC
    View 2779 SANBINA STREET Winter Park, FL MLS# O6388746
    $439,000
    3

    Beds

    2.0

    Baths

    1,405

    Sq.Ft.

    2779 SANBINA STREET

    Winter Park, FL

    Courtesy of MAINFRAME REAL ESTATE
    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

    Courtesy of EXP REALTY LLC
    View 814 DENSMORE DR Winter Park, FL MLS# O6399773
    • Virtual Tour
    1 of 24
    $425,000
    4

    Beds

    2.0

    Baths

    1,610

    Sq.Ft.

    814 DENSMORE DR

    Winter Park, FL

    Courtesy of ORANGE SLICE PROPERTIES
    View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
    • Recently Listed with Virtual Tour
    1 of 33
    $425,000
    940

    Sq.Ft.

    157 E NEW ENGLAND AVENUE 302

    Winter Park, FL

    Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
    View 3054 BLUEBROOK DRIVE Winter Park, FL MLS# O6398450
    $410,000
    3

    Beds

    2.0

    Baths

    1,939

    Sq.Ft.

    3054 BLUEBROOK DRIVE

    Winter Park, FL

    Courtesy of WEATHERSPOON REALTY INC
    View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
    $410,000
    3

    Beds

    2.0

    Baths

    1,402

    Sq.Ft.

    7532 AZUREBROOK COURT

    Winter Park, FL

    Courtesy of RE/MAX TOWN & COUNTRY REALTY
    View 340 KILLARNEY BAY COURT 4-4 Winter Park, FL MLS# O6407259
    • Recently Listed with Virtual Tour
    1 of 37
    OPEN HOUSE: Saturday 5/23 1:00 PM - 3:00 PM
    $410,000
    2

    Beds

    2.1

    Baths

    1,428

    Sq.Ft.

    340 KILLARNEY BAY COURT 4-4

    Winter Park, FL

    Courtesy of KELLER WILLIAMS WINTER PARK
    View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
    • Recently Listed with Virtual Tour
    1 of 22
    $410,000
    3

    Beds

    2.0

    Baths

    1,122

    Sq.Ft.

    1092 EASTBROOK BOULEVARD

    Winter Park, FL

    Courtesy of JC FLORIDA REALTY 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

    390

    Estimated median home price

    $787,500
    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

    PriceCount
    $0 - 100K2
    $100K - 200K49
    $200K - 300K23
    $300K - 400K24
    $400K - 500K29
    $500K - 600K22
    $600K - 700K29
    $700K - 800K20
    $800K - 900K16
    $900K - 1M10
    $1M - Max166

    Homes for Sale by Type in Winter Park, FL

    Property TypeCount
    Single Family246
    Townhouse15
    Condo88
    Commercial7
    Rental73
    Lots and Land27
    Condo/Town/CoOp0
    CoOp0
    Multi Family4
    Mobile Home0
    Farms0

    (Data as of 5/23/2026)

    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 5/23/2026.

    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 5/23/2026.

    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 5/23/2026.

    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 5/23/2026.