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Craftsman Homes for Sale in Windermere, FL

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  • /41

    $1,120,000

    Open Sat 2PM - 4PM
    • 6 Beds
    • 4.5 Baths
    • 4,625 Sq Ft

    13525 Gorgona Isle Dr, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless

    Agent Photo

    Roo Klaers

    COLDWELL BANKER REALTY

    (407) 842-8447

    13525 Gorgona Isle Dr, Windermere, FL 34786
  • /82

    $2,175,000

    $110K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 5,031 Sq Ft

    713 Main St, Windermere, FL 34786

    Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with excellent walkability. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a

    Agent Photo

    Kari Fleck

    THE REAL ESTATE COLLECTION LLC

    (407) 494-6941

    713 Main St, Windermere, FL 34786
  • /100

    $3,450,000

    Open Sat 11AM - 1PM $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 5,273 Sq Ft

    10577 Down Lakeview Cir, Windermere, FL 34786

    Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with

    Simon Simaan THE SIMON SIMAAN GROUP

    10577 Down Lakeview Cir, Windermere, FL 34786
  • /30

    $698,000

    Open Sat 12PM - 4PM
    • 3 Beds
    • 2 Baths
    • 2,108 Sq Ft

    13836 Bluebird Pond Rd, Windermere, FL 34786

    Step into this impeccably maintained, move-in ready home in Summerport—one of Windermere’s most sought-after communities. With its high ceilings and elegant crown molding, the home feels both grand and inviting. The kitchen features quartz countertops, a hot water dispenser, a cozy café area, and a walk-in pantry. Recent updates include a new HVAC system and water heater, a 2021 roof, and R-38

    Keith Gordon GETMOREOFFERS

    13836 Bluebird Pond Rd, Windermere, FL 34786
  • /25

    $539,000

    $210K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,151 Sq Ft

    6673 Duncaster St, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Located in the highly sought-after Windermere area, this 3-bedroom, 2-bath residence offers 2,151 heated square feet of functional and versatile living space. The layout includes a formal living room, a spacious great room, and a dedicated den/study, providing flexibility for work, entertaining, or additional living areas. A covered lanai extends

    Lilyan Machuca MY REALTY GROUP, LLC.

    6673 Duncaster St, Windermere, FL 34786

Home Trends in Windermere, FL

Housing Trends

Median Sale Price
$830,000
Median Single Family Sale Price
$1,100,000
Median Townhouse Sale Price
$395,000
Median 2 Bedroom Sale Price
$294,000
Average Price Per Sq Ft
$368
Number of Homes for Sale
233
Last 12 months Home Sales
669
Months of Supply
4.20
Median List Price
$975,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-1%
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