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Craftsman Homes for Sale in Windermere, FL

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  • /39

    $1,098,000

    $22K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,625 Sq Ft

    13525 Gorgona Isle Dr, Windermere, FL 34786

    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 entertaining.A dramatic two-story foyer creates a

    Agent Photo

    Roo Klaers

    COLDWELL BANKER REALTY

    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

    713 Main St, Windermere, FL 34786
  • /100

    $3,350,000

    $150K 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

    $1,499,000

    Pre-Foreclosure
    • 3 Beds
    • 2 Baths
    • 2,188 Sq Ft

    20 Oakdale St, Windermere, FL 34786

    Welcome to 20 Oakdale Street, an exceptional waterfront luxury residence in the highly sought-after Town of Windermere with direct access to Lake Down and the Butler Chain of Lakes offering an ideal blend of elegance, privacy, and Florida lifestyle, this beautiful home is perfectly positioned to enjoy the area's charming small-town atmosphere while remaining just minutes from world-class dining,

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    20 Oakdale St, Windermere, FL 34786
  • /25

    $530,000

    $219K 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
  • /62

    $624,000

    • 4 Beds
    • 2.5 Baths
    • 2,776 Sq Ft

    12580 Cragside Ln, Windermere, FL 34786

    A rare first-time offering in the highly sought-after Lakes of Windermere, 12580 Cragside Lane is a meticulously maintained, original-owner residence with timeless appeal. Set on a desirable corner homesite, this thoughtfully designed single-story home offers 2,776 SF of living space w/ 4 bedrooms, 2 1/2 baths & a floor plan that gracefully balances formal entertaining w/ comfortable everyday

    Padgett McCormick KELLY PRICE & COMPANY LLC

    12580 Cragside Ln, Windermere, FL 34786

Home Price Trends

Median Sale Price
$840,000
Median Single Family Sale Price
$1,085,990
Median Townhouse Sale Price
$397,000
Median 2 Bedroom Sale Price
$350,000
Average Price Per Sq Ft
$368
Number of Homes for Sale
259
Last 12 months Home Sales
684
Months of Supply
4.50
Median List Price
$950,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
0%
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