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    The Downtown Winter Garden Area

    Winter Garden › The Downtown Winter Garden Area

    Living in the Original & Downtown Winter Garden Area

    the Downtown Winter Garden AreaWhat we call the Downtown Winter Garden Area is actually the original town of Winter Garden. This was where the main residential areas were and the citrus groves were found to the South in what is now the Winter Garden Village area and the booming Horizon West area.

    Comprising well over 30 neighborhoods including the area is centered around the historic downtown core along Plant Street. This area is the hub of activity and where you will not only find Town Hall, but most of the social activity in the town.

    You will find homes ranging from the early 1900's to new construction with all the latest and greatest features.  Most of the options in this area are single family homes, but you will also find several townhome options in the area.

    Where is the Downtown Area in Winter Garden?

    The Downtown or Original Winter Garden area is now located in what would be just the Northern section of the growing Winter Garden Area.  It is North of the Florida Turnpike, West of the 429 Expressway, East of the Oakland Area of Winter Garden and South of Lake Apopka.

    The area includes most of what was considered Winter Garden, before the community started growing South toward Disney when the 429 expressway opened up former Orange Groves for development.

    Hwy 50 runs East-West through it's southern section and Plant Street (438) runs diagonally through the area including through the heart of Downtown Winter Garden.  The area is well known for the popular West Orange Trail running through this areas many neighborhoods.

    How Far from the Downtown Winter Garden Area to...

    • Downtown Orlando: 17 miles
    • Disney & Universal: 17 miles
    • Orlando International Airport: 25 miles
    • Port Canaveral & Cocoa Beach: 70 miles

    Downtown Winter Garden Area Neighborhoods

    The Downtown Winter Garden AreaNeighborhoods in the Downtown and Northern Area of Winter Garden include:

    • Brandy Creek
    • Chapin Station
    • Courtlea Oaks
    • Courtlea Park
    • Covington Chase
    • Crown Point Springs
    • Daniels Crossing
    • Downtown Winter Garden
    • Fullers Crossing
    • Fullers Landing
    • Heritage at Plant Street
    • Island Pointe
    • Kings Bay
    • Lake Cove Pointe
    • Lakeview Reserve
    • Magnolia Wood
    • McAllister Landing
    • Oakglen Estates
    • Oaks at Brandy Lake
    • Park Place
    • Regal Pointe
    • Stanton Estates
    • Sterling Pointe
    • Timbercreek Pines
    • Traditions
    • Trails of Winter Garden
    • Tuscany
    • Walkers Grove
    • Winter Oaks

    Attractions within the Downtown Winter Garden AreaDowntown Winter Garden Attractions and Events

    There is Always something happening in the Downtown Winter Garden area. Whether it's a special holiday event, weekend celebration or just a random Tuesday afternoon.

    Attractions

    • Winter Garden Heritage Museum
    • Central Florida Railroad Museum
    • SoBo Art Gallery
    • Downtown Splash Pad
    • Garden Theater
    • Stroll or Bike the West Orange Trail
    • Crooked Can Brewery

    Events

    • First Fridays on the Plaza
    • Saturday Farmers Market
    • Cruz-N-Car Show
    • Blues & BBQ
    • Evening at the POPS
    • Spring Fever in the Garden
    • 4th of July Party in the Park
    • Halloweenfest
    • Light Up Winter Garden
    • Annual Christmas Parade

    There are also an overwhelming number of dining and bar options available.

    Many of the neighborhoods fall within the Golf Cart Zone which allows residents to use their golf carts to reach the central downtown area rather than having to drive.  The West Orange Trail also connects many neighborhoods to the downtown area, so it is common to see many residents utilizing the trail rather than car.

    Downtown Winter Garden Area Latest Listings

    229 1st Street, Winter Garden image
    229 1st Street, Winter Garden $279,965

    great investment opportunity, 2 house on one property. first is a 4bed 2 bath, second house is 2bed 2bath, both properties have been fully renovated, new floors. new kitc...

    • 6 Beds
    • 3 Baths
    • Twin City Dev Co Sub SubDv.
    • 34787 Zip Code
    226 Surprise Drive, Winter Garden image
    226 Surprise Drive, Winter Garden $739,990

    Immediate occupancy on this gorgeous new construction home by Stanley Martin. Just one block from Dillard Elementary and less than a mile from Plant Street, this is your ...

    • 4 Beds
    • 3.5 Baths
    • Dillard Pointe SubDv.
    • 34787 Zip Code
    244 Surprise Drive, Winter Garden image
    244 Surprise Drive, Winter Garden $742,500

    Immediate occupancy on this gorgeous new construction home by Stanley Martin. Just one block from Dillard Elementary and less than a mile from Plant Street, this is your ...

    • 4 Beds
    • 3.5 Baths
    • Dillard Pointe SubDv.
    • 34787 Zip Code
    819 Mcpherson Place, Winter Garden image
    819 Mcpherson Place, Winter Garden $539,000

    Ready, Set, Move! This 5 bedroom 3 1/2 bath home has a spacious open 1st floor with an amazing floorplan. Formal spaces greet you as you enter this fantastic Winter Gar...

    • 5 Beds
    • 3.5 Baths
    • Fullers Crossing Ph 03 A-G SubDv.
    • 34787 Zip Code
    420 E Cypress Street, Winter Garden image
    420 E Cypress Street, Winter Garden $574,900

    This stunning, move-in ready home is on a large lot in a hot neighborhood. From the open-concept kitchen and living space to the large fenced-in backyard, there is plenty...

    • 3 Beds
    • 2 Baths
    • Overstreet Crate SubDv.
    • 34787 Zip Code
    232 Surprise Drive, Winter Garden image
    232 Surprise Drive, Winter Garden $787,990

    Immediate occupancy on this gorgeous new construction home by Stanley Martin. Just one block from Dillard Elementary and less than a mile from Plant Street, this is your ...

    • 4 Beds
    • 3.5 Baths
    • Dillard Pointe SubDv.
    • 34787 Zip Code
    214 Surprise Drive, Winter Garden image
    214 Surprise Drive, Winter Garden $784,990

    Immediate occupancy on this gorgeous new construction home by Stanley Martin. Just one block from Dillard Elementary and less than a mile from Plant Street, this is your ...

    • 4 Beds
    • 3.5 Baths
    • Dillard Pointe SubDv.
    • 34787 Zip Code
    1072 Island Pointe Drive, Winter Garden image
    1072 Island Pointe Drive, Winter Garden $575,000

    One or more photo(s) has been virtually staged. Multiple offers received. Please submit highest and best offer by 6 PM, Saturday, June 10th. Welcome home to this stunni...

    • 4 Beds
    • 3 Baths
    • Island Pointe Sub SubDv.
    • 34787 Zip Code
    474 Hazelnut Court, Winter Garden image
    474 Hazelnut Court, Winter Garden — 25g $849,997

    Welcome to the epitome of modern living at Park Place in Winter Garden! This stunning corner lot townhome offers the perfect blend of luxury and convenience. With 3 bedro...

    • 3 Beds
    • 2.5 Baths
    • Park Place/Winter Garden SubDv.
    • 34787 Zip Code
    971 Butterfly Boulevard, Winter Garden image
    971 Butterfly Boulevard, Winter Garden — 971 $225,000

    Charming 3 Bedroom 2 Bathroom Winter Garden One Level Townhome. The main living area has vaulted ceilings with a skylight bringing in tons of natural light. The owners' s...

    • 3 Beds
    • 2 Baths
    • Westside Twnhms Ph 04 SubDv.
    • 34787 Zip Code
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    Address Search

    Realtor David MyersDavid Myers 407-801-3286
    Your Winter Garden Real Estate Expert

    Winter Garden Areas

    • Downtown Winter Garden
    • Horizon West
    • Oakland
    • Winter Garden Village

    Downtown Winter Garden Area Neighborhoods

    • Downtown Winter Garden
    • Brandy Creek
    • Chapin Station
    • Courtlea Oaks
    • Courtlea Park
    • Covington Chase
    • Crown Point Springs
    • Daniels Crossing
    • Fullers Crossing
    • Fullers Landing
    • Heritage at Plant Street
    • Island Pointe
    • Kings Bay
    • Lake Cove Pointe
    • Lakeview Reserve
    • Magnolia Wood
    • McAllister Landing
    • Oakglen Estates
    • Oaks at Brandy Lake
    • Park Place
    • Regal Pointe
    • Stanton Estates
    • Sterling Pointe
    • Timbercreek Pines
    • Traditions
    • Trails of Winter Garden
    • Tuscany
    • Walkers Grove
    • Winter Oaks

    Winter Garden Village Area Neighborhoods

    • Alexander Ridge
    • Amberleigh
    • Avalon Reserve
    • Avalon Ridge (NEW)
    • Banana Bay Estates
    • Bay Isle
    • Belle Meade
    • Black Lake Park
    • Black Lake Preserve
    • Bradford Creek
    • Bronsons Landing
    • Canopy Oaks
    • Carriage Pointe
    • Cobblestone
    • Country Lakes
    • Cypress Reserve
    • Daniels Landing
    • Deerfield Place
    • Emerald Ridge
    • Foxcrest
    • Glynwood
    • Grove Park
    • Grovehurst
    • Hickory Hammock
    • Johns Lake Pointe
    • Lake Roberts Landing
    • Orange Cove
    • The Orchard
    • Oxford Chase
    • Regency Oaks
    • Reserve at Carriage Pointe
    • Roper Reserve
    • Sanctuary at Twin Waters
    • Southern Pines
    • Stone Creek
    • Stoneybrook West
    • Sunset Lakes
    • Tilden Place
    • Twinwaters
    • Waterside
    • Westfield Lakes
    • Windermere Crossing
    • Windward Cay
    • Wintermere Harbor
    • Wintermere Pointe
    • Woodbridge on the Green

    Horizon West Area Neighborhoods

    • Avalon Cove
    • Cove At Hamlin
    • Enclave at Hamlin
    • Encore at Ovation
    • Hamilton Gardens
    • Hamlin Reserve
    • Hawksmoor
    • Highland Ridge (NEW)
    • Highlands Summerlake
    • Independence
    • Isles Of Lake Hancock
    • Lake Hancock Preserve
    • Lakeshore
    • Lakeside at Hamlin
    • Lakeview Pointe
    • Lakeview Preserve
    • Latham Park
    • Mezzano (NEW)
    • Orchard Hills
    • Orchard Park
    • Osprey Ranch (NEW)
    • Overlook At Hamlin
    • Panther View
    • Ravenna
    • Sanctuary at Hamlin
    • Storey Grove
    • Summerlake
    • Summerlake Groves
    • Waterleigh
    • Watermark
    • Westhaven Ovation (NEW)
    • Wincey Groves
    • Winding Bay

    Oakland Area Neighborhoods

    • Deer Island
    • Downtown Oakland
    • Hull Island
    • Johns Cove
    • Johns Landing
    • Longleaf at Oakland
    • Oakland Hills
    • Oakland Park
    • Oakland Trails
    • Trailside Station
    • Tucker Oaks
    • Verde Park

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  • David Myers - Broker Associate
    WinterGardenNeighborhoodRealty.com Team
    Ziro Realty, LLC
    619 Celebration Ave
    Celebration, FL 34747
    Call/Text: 407-801-3286
    https://www.WinterGardenNeighborhoodRealty.com





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