13

5-Bedroom Homes for Sale in Windermere

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  • /80

    $3,750,000

    • 6 Beds
    • 5.5 Baths
    • 6,819 Sq Ft

    2828 Marquesas Ct, Windermere, FL 34786

    Gorgeous Private Lakefront Custom Brick Estate over 10,000 sq ft under roof, just under 7,000 sq ft under HVAC. First Time Ever on Market! Step thru the Gorgeous Leaded Glass Doors into this Magnificent Estate the Entry made for Royalty Custom Magnolia Curved Staircase with custom Italian Marble Flooring installed 2024. Updated Massive Chandler with Sconces lighting grace the Staircase. To the

    Carolyn Cook DALTON WADE INC

    2828 Marquesas Ct, Windermere, FL 34786
  • /85

    $3,499,000

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

    4301 Down Point Ln, Windermere, FL 34786

    PRICE IMPROVEMENT *** Up to $25,000 in Buyer Closing Cost CREDIT Available with Preferred Lender! *** Inquire for further information *** 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. Upon entry, be captivated by

    Ashley Boyd BHHS FLORIDA REALTY

    4301 Down Point Ln, Windermere, FL 34786
  • /86

    $4,899,000

    • 7 Beds
    • 10.5 Baths
    • 5,935 Sq Ft

    225 Magnolia St, Windermere, FL 34786

    LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWNUnveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakes—a residence that redefines lakefront luxury in the exclusive town of Windermere. Custom-built in 2019, this Mediterranean-inspired estate is a sanctuary of sophistication, offering unparalleled waterfront living with direct frontage

    George Doulamis COMPASS FLORIDA LLC

    225 Magnolia St, Windermere, FL 34786
  • /44

    $4,395,000

    • 5 Beds
    • 6.5 Baths
    • 5,639 Sq Ft

    801 W 2nd Ave, Windermere, FL 34786

    Experience the epitome of lakefront living on the Butler Chain of Lakes with this exceptional Windermere estate. On one of the area’s desirable streets, this home offers over $350,000 of recent luxurious upgrades, including a new kitchen and fireplace, new windows and doors, landscape lighting, new landscaping, a newly painted exterior and roof. The home also boasts a newly added $85,000 dock,

    Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

    801 W 2nd Ave, Windermere, FL 34786
  • /32

    $1,200,000

    • 5 Beds
    • 3 Baths
    • 2,918 Sq Ft

    3443 Wild Myrtle Ct, Windermere, FL 34786

    Welcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a serene 1.2-acre cul-de-sac lot in the esteemed Lake Butler Estates of Windermere, Florida. This expansive 5-bedroom, 3-bathroom residence offers 2,918 square feet of thoughtfully designed living space, combining modern updates with timeless charm.The home boasts a formal living room featuring a whitewashed

    Michael Julian JULIAN PROPERTIES, INC.

    3443 Wild Myrtle Ct, Windermere, FL 34786
  • /14

    $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
  • /55

    $2,499,000

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

    409 W 2nd Ave, Windermere, FL 34786

    Surrounded by glistening lakes and shaded by towering oaks, Windermere offers an unbeatable blend of natural beauty and small-town charm. Friendly neighbors, golf cart-friendly streets, and walkability to cafes, shops, parks, and a local brewery make everyday living feel like a getaway. Enjoy sandy beaches, tennis and pickleball courts, and easy access to kayaking, fishing, and boating on the

    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
  • /77

    $2,650,000

    • 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
  • /31

    $2,499,000

    • 5 Beds
    • 5.5 Baths
    • 4,094 Sq Ft

    11113 Lake Butler Blvd, Windermere, FL 34786

    Welcome to this beautiful, unique and modern home, built less than 3 years ago. Secluded in a great sized lot and within the sought-after and exclusive City of Windermere, known for its lush nature landscape trails, recreation parks, restaurants, cozy stores, beautiful lakes, great schools and much more!!! This luxury property also has a HOA 1/24th private deeded land with lake access, dock and

    Stella Freeman QUATTRO R E SOLUTIONS LLC

    11113 Lake Butler Blvd, 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
  • /65

    $2,900,000

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

    800 W 2nd Ave, Windermere, FL 34786

    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 of the Pool & Lake -

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    800 W 2nd Ave, Windermere, FL 34786
  • /13

    $2,200,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,994 Sq Ft

    1020 Oakdale St, Windermere, FL 34786

    Under Construction. Extraordinary new construction estate by renowned builder Davila Homes, nestled in the heart of Downtown Windermere. Meticulously designed and artfully executed, this five-bedroom, four-and-a-half-bathroom residence offers 3,994 square feet of luxurious living space. From the moment you step inside, you're enveloped in elevated elegance, soaring ceilings, rich custom millwork,

    Christopher Christensen COMPASS FLORIDA LLC

    1020 Oakdale St, Windermere, FL 34786

Home Trends in Windermere, FL

Housing Trends

Median Sale Price
$1,177,500
Median Single Family Sale Price
$1,360,000
Average Price Per Sq Ft
$511
Number of Homes for Sale
27
Last 12 months Home Sales
54
Months of Supply
6.00
Median List Price
$1,499,950
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-4%
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