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    Windermere Real Estate Search

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    Orange County, Florida, has a reputation for being exceptional with coveted amenities and high-end residential communities. A fine example is the charming community of Windermere, nestled among the Butler Chain of Lakes. Windermere is home to roughly two thousand, five hundred people in the prestigious Orlando Metro Area. This small bedroom community offers prospective homebuyers the best of both worlds, with a cozy small-town ambiance and high-end exclusive communities in proximity to big-city services, amenities, and attractions. Because of its convenient location, Windermere has experienced consistent growth since 2000. 

    Originally comprising fewer than two square miles, the town of Windermere was established in 1925. In 2007, it annexed Butler Bay and is therefore slightly larger today. Many others that share the 34786 zip code share Windermere's name, but are considered part of unincorporated West Orange County. Windermere itself has much to offer prospective homebuyers. For example, there are many lovely historic structures in the town, including the Windermere Town Hall and the 1890 Windermere School.

    Further contributing to its appeal to homebuyers, Windermere is a family-friendly community served by the Orange County School District and the international and prestigious Windermere Preparatory School. It is in proximity to numerous entertainment, attraction, and recreation destinations and events, including all of the areas theme parks, I-Drive, and the Bay Hill Classic Golf Tournament. Weekly farmers market and monthly food truck night are very popular year-round in historic downtown Windermere. 

    Real estate in Windermere is surprisingly diverse for such a small community. Homes for sale in Windermere include attached and detached residences of differing ages, architectural styles, and sizes. There are modest Windermere properties with competitive listing prices, and there are sprawling luxury homes in exclusive estate communities in Windermere with listing prices well into the millions. Among Windermere's most noteworthy neighborhoods is the exclusive county club community of Isleworth, nestled on the Butler Chain of Lakes and home to many celebrities and professional sports figures. We would be delighted to answer all of your questions about currently listed properties in Windermere, Florida, so if you would like to learn more, please contact us as soon as it is convenient.

    Our website features the best Windermere real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

    You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

    Curious about what’s happening in the Windermere real estate market? Sign up for a Windermere Real Estate Market Report to see what’s active, under contract, and sold!

    Considering selling or refinancing your home? Get an INSTANT property valuation now!

    Contact us today to find out how we can be of assistance to you!

    Newest Windermere Homes & Condos for Sale

    11409 N Camden Commons Drive, Windermere image
    11409 N Camden Commons Drive, Windermere $1,100,000

    Don't miss out on this home inside the exclusive guard gated community of Keens Pointe and home to the Golden Bear Country Club featuring Jack Nicklaus golf course. This ...

    • 4 Beds
    • 4.5 Baths
    • Keenes Pointe SubDv.
    • 34786 Zip Code
    411 E 6th Avenue, Windermere image
    411 E 6th Avenue, Windermere $899,900

    Beautifully updated home in the heart of downtown Windermere on a spacious homesite just a short stroll to Main Street. Nestled among majestic oaks and down a long pavere...

    • 4 Beds
    • 3 Baths
    • Windermere Rep SubDv.
    • 34786 Zip Code
    12842 Jacob Grace Court, Windermere image
    12842 Jacob Grace Court, Windermere $1,388,800

    Custom Video www.12842jacobgrace.site/mls FIRST TIME EVER OFFERED FOR SALE, original owner and very first lot ever sold in Tildens Grove ! Pride of ownership is self e...

    • 5 Beds
    • 3.5 Baths
    • Tildens Grove Ph 01 47/65 SubDv.
    • 34786 Zip Code
    1825 Windermeredown Place, Windermere image
    1825 Windermeredown Place, Windermere $1,295,000

    One or more photo(s) has been virtually staged. Gorgeous Executive Estate on over an acre is SUPER SPACIOUS with versatile floor plan where rooms can be repurposed as you...

    • 6 Beds
    • 4.5 Baths
    • Windermere Downs Ph 03 SubDv.
    • 34786 Zip Code
    13534 Bramham Lane, Windermere image
    13534 Bramham Lane, Windermere $469,900

    * Multiple offers received, Seller has requested Highest and/or Best by 2:00 PM Monday April 4, 2023 * Attention Disney Lovers! On a quiet tree lined street approximatel...

    • 3 Beds
    • 2 Baths
    • Lakes/Windermere-Peachtree SubDv.
    • 34786 Zip Code
    11486 Misty Oak Alley, Windermere image
    11486 Misty Oak Alley, Windermere $499,900

    Beautiful single family home with 3 bedrooms and 2 1/2 baths located in the Ashlin Park Community in Windermere. The kitchen is upgraded with stainless steel appliances....

    • 3 Beds
    • 2.5 Baths
    • Ashlin Park Ph 1 SubDv.
    • 34786 Zip Code
    11644 Ashlin Park Boulevard, Windermere image
    11644 Ashlin Park Boulevard, Windermere $600,000

    This lovely two-story home found in desirable Ashlin Park offers the convenience of a premium location to A- rated schools in Windermere. This home features exquisite upg...

    • 4 Beds
    • 2.5 Baths
    • Ashlin Park Ph 1 SubDv.
    • 34786 Zip Code
    12264 Montalcino Circle, Windermere image
    12264 Montalcino Circle, Windermere $6,295,000

    A masterpiece of artful design nestled in Windermere, Florida, this one-of-a kind, Lake Burden home immediately transports you to a level of world-class beauty, serenity...

    • 4 Beds
    • 4.5 Baths
    • Casa Del Lago Rep SubDv.
    • 34786 Zip Code
    12224 Mckinnon Road, Windermere image
    12224 Mckinnon Road, Windermere $1,799,000

    One acre of Windermere lakefront living, with no HOA! This home is situated on Lake Crescent, which is crystal clear and the largest private lake in Windermere. When the ...

    • 4 Beds
    • 4.5 Baths
    • Butler Bay SubDv.
    • 34786 Zip Code
    12846 Langstaff Drive, Windermere image
    12846 Langstaff Drive, Windermere — Lake Reams Townhomes $365,000

    Rare Lake Reams Townhome in Windermere, Fl. 1380 sq ft, 2 bedroom, 2.5 bath Home on Beautiful Mature Oak Tree Lined Street. 2 Car Garage with Courtyard in between. Ne...

    • 2 Beds
    • 2.5 Baths
    • Lakes/Windermere-Lk Reams Twnh SubDv.
    • 34786 Zip Code
    12856 Strode Lane, Windermere image
    12856 Strode Lane, Windermere — Lot 244 $430,000

    Two story town home in excellent condition and newly painted inside! The kitchen features wood cabinets, granite counter tops, backsplash and a large island. The lighting...

    • 3 Beds
    • 2.5 Baths
    • Windermere Sound Ph 2 SubDv.
    • 34786 Zip Code
    9725 Chestnut Ridge Drive, Windermere image
    9725 Chestnut Ridge Drive, Windermere $4,399,000

    This home features 6885 square feet of AC living space and 11,000 square feet under roof! The home is situated inside Isleworth, a gated community with 24 hour security b...

    • 5 Beds
    • 6 Baths
    • Isleworth SubDv.
    • 34786 Zip Code
    5507 Worsham Ct, Windermere image
    5507 Worsham Ct, Windermere $5,950,000

    This stunning custom estate overlooks the fourteenth green on Isleworth Golf and Country Club, one of the world’s most prestigious private golf club communities. As you c...

    • 5 Beds
    • 5.5 Baths
    • Isleworth SubDv.
    • 34786 Zip Code
    9247 Legado Drive, Windermere image
    9247 Legado Drive, Windermere — Mattamy Homes $820,000

    Luxury first rental property in Windermere with excellent schools. The property is located in the best and largest lot of the condominium and with a privileged view of th...

    • 4 Beds
    • 2.5 Baths
    • Legado SubDv.
    • 34786 Zip Code
    1810 Westover Reserve Boulevard, Windermere image
    1810 Westover Reserve Boulevard, Windermere $999,000

    Rare opportunity to own a home in the sought-after gated community of Westover Reserve in the heart of Windermere! An enclave of only 81 homes, this community offers imma...

    • 4 Beds
    • 5 Baths
    • Westover Reserve Ph 01 SubDv.
    • 34786 Zip Code
    11545 Brickyard Pond Lane, Windermere image
    11545 Brickyard Pond Lane, Windermere $1,699,765

    Magnificent Lakefront home set on a calm cul-de-sac! This spectacular residence treats you to ample privacy, space, and comfort in Windermere. Occupying an oversized 3/4-...

    • 6 Beds
    • 6.5 Baths
    • Lake Burden South Ph I SubDv.
    • 34786 Zip Code
    12525 Montalcino Circle, Windermere image
    12525 Montalcino Circle, Windermere $989,000

    ENOUGH LOOKING!! CHECK OUT this Gorgeous POOL home located in the Exclusive GATED Community Casa Del Lago in Windermere. This home has a lovely **courtyard feature** at t...

    • 4 Beds
    • 3.5 Baths
    • Casa Del Lago Rep SubDv.
    • 34786 Zip Code
    8057 Tibet Butler Drive, Windermere image
    8057 Tibet Butler Drive, Windermere $1,695,000

    THIS HOME IS THE ENTERTAINERS DREAM HOME! Located in the best community of Central Florida, it has a guard gated, golf, tennis and lakefront country club with a Signatur...

    • 4 Beds
    • 4 Baths
    • Keenes Pointe Unit 2 SubDv.
    • 34786 Zip Code
    11444 Misty Oak Alley, Windermere image
    11444 Misty Oak Alley, Windermere $599,990 ▼

    Don’t miss out on this absolutely remarkable, MOVE-IN ready home which will accommodate any family's needs. Upon entering the home you are greeted with many upgrades: hig...

    • 4 Beds
    • 2.5 Baths
    • Ashlin Park Ph 1 SubDv.
    • 34786 Zip Code
    11952 Camden Park Drive, Windermere image
    11952 Camden Park Drive, Windermere $1,690,000

    Welcome to your own private oasis in one of the largest lots at Keene’s Pointe! With plenty of space, both indoor and outdoor, a formal living and dining room, a kitchen ...

    • 5 Beds
    • 4 Baths
    • Keenes Pointe SubDv.
    • 34786 Zip Code
    11129 Lake Butler Boulevard, Windermere image
    11129 Lake Butler Boulevard, Windermere $849,000 ▲

    Rare Opportunity to own 1 of the last affordable move in ready homes in Downtown Windermere - Recent sales of new homes are over $2.0 on this street - The Lot is 100 feet...

    • 3 Beds
    • 2 Baths
    • Wauseon Ridge SubDv.
    • 34786 Zip Code
    9306 Blanche Cove Drive, Windermere image
    9306 Blanche Cove Drive, Windermere $17,500,000

    Sophisticated elegance masterfully packaged into a custom-crafted lakefront mansion built specifically for the ultimate sports enthusiast, situated behind the secured man...

    • 5 Beds
    • 6.5 Baths
    • Isleworth SubDv.
    • 34786 Zip Code
    11237 Camden Park Drive, Windermere image
    11237 Camden Park Drive, Windermere $1,200,000

    Welcome to your dream home located in the desirable Keene's Pointe community! This updated and upgraded 4 bedroom, 4 bath pool home boasts 3,492 square feet of luxurious ...

    • 4 Beds
    • 4 Baths
    • Keenes Pointe Unit 7 SubDv.
    • 34786 Zip Code
    5139 Isleworth Country Club Dr, Windermere image
    5139 Isleworth Country Club Dr, Windermere $7,500,000

    With a fabulous location along the front nine of Isleworth’s renowned championship golf course overlooking Hole 3, this expansive estate showcases just under 14,000 squar...

    • 7 Beds
    • 7.5 Baths
    • Isleworth SubDv.
    • 34786 Zip Code
    10430 Birch Tree Lane, Windermere image
    10430 Birch Tree Lane, Windermere $1,475,000

    Now is your opportunity to own a luxurious estate home in the highly sought after Windermere Downs neighborhood! This 6 bedroom, 4.5 bath Brierhill custom-built home sits...

    • 6 Beds
    • 4.5 Baths
    • Windermere Downs Ph 03 SubDv.
    • 34786 Zip Code
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