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Windermere, FL Homes for Sale with In-Law Suite

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  • /100

    $5,499,000

    • 6 Beds
    • 5.5 Baths
    • 6,448 Sq Ft

    1455 Kelso Blvd, Windermere, FL 34786

    Discover 11,699 sqft of total luxury at 1455 Kelso Blvd, a stunning lakefront estate in Windermere’s Kelso on Lake Butler community. Set on nearly an acre with 119 feet of frontage on Lake Butler, this fully renovated 6-bedroom, 5.5-bath home offers over 6,448 sqft of living square footage. Features include a gourmet kitchen, first-floor primary suite with lake views, an attached in-law suite

    Julie Sanchez THE REAL ESTATE COLLECTION LLC

    1455 Kelso Blvd, Windermere, FL 34786
  • /85

    $3,775,000

    • 5 Beds
    • 4 Baths
    • 6,834 Sq Ft

    4301 Down Point Ln, Windermere, FL 34786

    Awake to awe-inspiring sunrises from this unparalleled lakefront estate on LAKE DOWN, nestled within the renowned BUTLER CHAIN of LAKES. Experience the tranquility and exclusivity of Sunset Bay without the burden of HOA fees. Currently, this residence offers one of the most competitive prices per square foot for lakefront homes in Windermere of similar stature (6,000-7,000 sqft). Upon entry, be

    Ashley Boyd BHHS FLORIDA REALTY

    4301 Down Point Ln, Windermere, FL 34786
  • /65

    $3,100,000

    • 5 Beds
    • 4.5 Baths
    • 5,111 Sq Ft

    800 W 2nd Ave, Windermere, FL 34786

    Major Price Reduction * Detached Guest Suite overlooking Pool with Fireplace has Private Entrance in Courtyard - Courtyard Pool with Waterfall from the Heated Spa has the feel of an Olde World European Resort - Formal Living Room with Fireplace - Formal Dining Room with Fireplace - Family Room with Fireplace - Large Kitchen with Wine Cellar and Pantry in the Heart of the Home has incredible views

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    800 W 2nd Ave, Windermere, FL 34786
  • /5

    $1,850,000

    • 5 Beds
    • 6 Baths
    • 6,375 Sq Ft

    11056 Clipper Ct, Windermere, FL 34786

    Professional Pictures Coming Soon * Huge 5 Bedroom 6 Bath Multi-Generational Pool Home Has 1 Full Suite on 1st Floor & 2 Spacious Suites on the 2nd Floor * Open Floorplan * The Marina Bay Community Includes a Waterfront Marina and Launch Ramp for your boat that is directly connected to Lake Down and the Butler Chain of Lakes * Oversized 4 Car Garage with Drive Through Doors on Front & Rear of the

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    11056 Clipper Ct, Windermere, FL 34786
  • /45

    $1,250,000

    • 4 Beds
    • 3.5 Baths
    • 2,868 Sq Ft

    6125 Foxfield Ct, Windermere, FL 34786

    Popular Keene's Pointe in Windermere! 24 Hour attendant gated community. Located on the 1st Fairway, this beautiful 4 Bedroom, 3 1/2 Baths Villa Style home will not disappoint. Primary Bedroom with a expansive bathroom, along with 2 other bedrooms with en-suite baths are all located on the 1st floor. 1 Bedroom with 1/2 bath upstairs. Large open Dinng and Living Room overlook the screened

    Mary Ann Thompson RE/MAX Solutions

    6125 Foxfield Ct, Windermere, FL 34786
  • /55

    $2,499,000

    • 5 Beds
    • 4.5 Baths
    • 4,688 Sq Ft

    409 W 2nd Ave, Windermere, FL 34786

    Welcome to Second Avenue, a serene peninsula in the heart of Old Windermere. This recently remodeled home offers 5 bedrooms, 4.5 baths, including a detached poolside Guest House, seamlessly blending sleek architectural lines with the warmth of natural light.Designed for both comfort and sophistication, the home features cathedral ceilings and expansive windows, creating bright, airy living spaces

    Amanda Black UPSIDE REAL ESTATE INC

    409 W 2nd Ave, Windermere, FL 34786
  • /91

    $20,000,000

    • 7 Beds
    • 8.5 Baths
    • 10,649 Sq Ft

    11900 Lake Butler Blvd, Windermere, FL 34786

    Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all

    Julie Bettosini STOCKWORTH REALTY GROUP

    11900 Lake Butler Blvd, Windermere, FL 34786
  • /72

    $1,699,000

    • 5 Beds
    • 4 Baths
    • 3,810 Sq Ft

    8424 Lake Burden Cir, Windermere, FL 34786

    Keene's Pointe - 24 hour gated/attended community in Windermere, Florida, featuring The Golden Bear Club, an 18-hole course designed by Jack Nicklaus offering golf, fitness, tennis, swimming and dining. This pristine home has been completely renovated and features 5 bedrooms and 4 baths, formal dining, private office and much more. From the moment you enter this charming home you are greeted by

    Teresa Stewart SOUTHERN REALTY GROUP LLC

    8424 Lake Burden Cir, Windermere, FL 34786
  • /76

    $2,749,999

    • 4 Beds
    • 4.5 Baths
    • 5,118 Sq Ft

    8148 Tibet Butler Dr, Windermere, FL 34786

    Keene’s Pointe – exclusive 24-hour gated/attended community in highly desired Windermere, Florida.  This stunning FULLY REMODELED overlooks the third green/fourth tee box of The Golden Bear Club, an 18 hole golf course designed by Jack Nicklaus featuring golf, tennis, fitness, dining and swimming, with beautiful pond and lake views.  The entire home boasts hardwood flooring, designer touches,

    Teresa Stewart SOUTHERN REALTY GROUP LLC

    8148 Tibet Butler Dr, Windermere, FL 34786
  • /72

    $2,790,000

    • 6 Beds
    • 5.5 Baths
    • 4,599 Sq Ft

    1003 Oakdale St, Windermere, FL 34786

    Never Lived In Since Completely Remodeled and Expanded - Total of 6 Bedrooms - 5 Full Baths - 1 Pool or Guest Bath - Primary Suite & Guest Suite on 1st Floor - 4 More Bedrooms & 3 Bathrooms on 2nd Floor - Huge Bonus Room / Theatre / Game Room with Full Bathroom Over Garage - Separate Office on 1st Floor - 12 Foot Wide Folding Glass Doors Overlooking The Screened Pool & Lake Bessie - Newly

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    1003 Oakdale St, Windermere, FL 34786
  • /61

    $11,900,000

    • 6 Beds
    • 9 Baths
    • 14,435 Sq Ft

    4200 Down Point Ln, Windermere, FL 34786

    Nestled along almost 1,000’ of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2-acre peninsula reveals a masterpiece of architectural brilliance designed by Nasrallah and built by Ray Coudriet. The grand entry sets the tone, with a majestic staircase, a 25+ft hand-painted rotunda ceiling,

    Frank Del Toro REVEL REALTY LLC

    4200 Down Point Ln, Windermere, FL 34786

Home Trends in Windermere, FL

Housing Trends

Median Sale Price
$910,000
Median Single Family Sale Price
$1,150,000
Median Townhouse Sale Price
$418,000
Median 2 Bedroom Sale Price
$310,000
Average Price Per Sq Ft
$381
Number of Homes for Sale
147
Last 12 months Home Sales
327
Months of Supply
5.40
Median List Price
$999,500
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
12%
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