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new vacation homes for sale in Orlando

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Windermere Luxury Homes

new custom homes and luxury homes Orlando Windermere Luxury and Custom homes are available in this stunning town between the theme parks and Orlando in Central Florida. Styles of luxury homes In Windermere vary as per the community and price.

The Town of Windermere is one of the wealthiest residential communities in Central Florida. Yet it comes as a surprise to many when they leave the asphalt and hit the private dirt roads around the lake. With a population of just over 2,000, Windermere, which is named after Lake Windermere in England, is a cross between an English village and a Caribbean Island, right here in the heart of Orlando.

Windermere is renowned for its privacy and this is one of the main reasons that world famous athletes, CEO’s and A-listers call it home. Upscale gated communities and huge estate homes stand side by side along the sand bottomed Chain of Lakes. Exclusivity is probably the one word which best describes Windermere and the Towne of Windermere strives to maintain its standards on behalf of its owners.

Casabella at Windermere - luxury homes on Butler Chain of Lakes

Casabella at Windermere luxury homes Orlando

Casabella at Windermere is latest luxury home community in the prestigious and highly sought after Windermere area of Orlando. Casabella at Windermere features estate-sized home sites and award-winning luxury homes built exclusively by Toll Brothers.

Casabella at Windermere is a new, gated community offering just 79 luxury single-family homes. Located in Windermere, the Casabella exclusive estate home community is located within minutes of upscale shopping and dining at the Mall at Millenia, Restaurant Row, and Winter Garden Village. First-class golf courses, world-famous attractions, and the Butler Chain of Lakes are all on your doorstep and provide endless activities for your family.

These stunning estate homes are priced between $750,000 and $1.5 million

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Bellaria Windermere

Casabella at Windermere luxury homes Orlando

Surrounded by the beautiful Butler Chain of Lakes, Bellaria is an intimate, gated community of luxury homes located in Windermere. Bellaria offers expansive home sites and elegant estate homes with luxury home features such as coffered ceilings, crown molding, walk-in closets, grand foyer entrance, tile roofs, covered lanais, and paver driveways.

This exclusive community in Windermere is within minutes of shopping and dining at the Mall at Millenia and Winter Garden Village. Championship golf courses, world-famous attractions, and the Butler Chain of Lakes provide endless activities for family members of all ages.

  • Bellaria features spacious 3/4 acre, 120'+ wide home sites.
  • Private, gated community with a 24-hour staffed gatehouse and just 65 home sites.
  • Variety of award-winning home designs with hundreds of available options to personalize your dream home.
  • Gourmet kitchen features natural gas cooking, granite countertops, tile backsplash, stainless steel KitchenAid® appliances, and Yorktowne® cabinets with smooth-glide drawers.

Bellaria offers 8 luxury home designs with prices starting from $807,995

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Casa del Lago on Lake Burden

Casa del Lago in Windermere luxury homes Orlando

Casa del Lago on Lake Burden in Windermere is one of the latest waterfront luxury home communities in this sought after location. Nestled close to the prestigious communities of Isleworth, Keene’s Pointe and Lake Butler Sound, Casa del Lago boasts pedigree neighbors.

Casa del Lago residents pass through stunning Spanish themed stone, wood and ornately dressed wrought iron gates. Entering this upscale community of picturesque luxury homes you are welcomed by the stone fountain, lush landscaping with beautiful splashes of bougainvilla which adorn the trellises.

Casa del Lago affords residents an immediate sense of luxury and privacy. The streets are highlighted by warm lighting along the sidewalks, which border the old-world privacy walls of the 88 custom built homes, 23 of which are sited directly on Lake Burden.

For those not fortunate enough to own by the water, you can always enjoy a stroll along the scenic boardwalk.

Homes from $550,000 to $2,000,000. Lots start from around $200,000

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Sawyer Sound on Little Lake Sawyer - Luxury lakefront homes

Sawyer Sound on Little Lake Sawyer in Windermere luxury homes Orlando

At Sawyer Sound on Little Lake Sawyer the lot sizes are 1/2 acre and larger with a minimum build of 3,000 square feet. These custom home designs in Windermere feature Mediterranean, Contemporary and French Country styles with no two homes looking alike.

We estimate that monthly HOA dues will fall somewhere between $250-350 per month.

Lots range between $225k and $475k. Homes are starting from the $800’s

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Emerson Pointe - Luxury lakefront residences

Emerson Pointe luxury homes Orlando

Emerson Pointe is stunning waterfront community nestled on a private peninsula in Bay Hill along the distinguished Butler Chain of Lakes. Emerson Pointe is an exclusive Orlando, 24 hour guard gated community, a secluded waterfront enclave, featuring 72 prime home sites and endless unobstructed views of the surrounding landscape behind the elegant gated entrance.

These stunning estate homes are priced from $900,000

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The Gardens at Keene's Pointe - Luxury lakefront residences

Emerson Pointe luxury homes Orlando

The Gardens at Keene’s Pointe are the final village of new homes at this wonderful community in the Windermere Golf and Country Club. These Lakefront homes afford owners with spectacular lake views Cinderella’s Castle and where the Disney fireworks as they reflect on the shimmering waters at dusk.

Classic European style aptly describes The Gardens of Keene’s Pointe in Windermere. Adorned with its sparkling fountains and pergolas set amongst native flora and heritage citrus.

Facing west over the sand-bottomed Lake Burden, The Gardens of Keene’s Pointe represents a stylish European enclave for owners who appreciate the finer things in life.

The Clubhouse which is the heart of The Golden Bear Jack Nicklaus designed Signature Golf Course is only minutes away from The Gardens. Here you can practice your serve on the tennis courts or work of some energy in the stunning gym which overlooks the swimming pool and recreational area.

Home construction at The Gardens at Keene’s Pointe are by the Preferred Builder Guild

These stunning estate homes are priced from $1,200,000

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Waterstone - Luxury homes

Waterstone luxury homes in Windermere Orlando

Waterstone is one of the last great lakeside parcels in Windermere. Featuring 120 home sites, the private gated community of Waterstone is an idyllic place to call home. With the Butler Chain of Lakes as your backdrop, you can embrace the tranquility of this sanctuary and unwind alongside nature and the sparkling waters of Lake Butler.

Once you have crossed the cobblestone bridge, you are met by an oasis full of fragrances from the lush landscaping. Pristine lakes will catch your eye and nature trails which beckon, offering quiet contemplation.

Although Waterstone is intimate in size, the home sites are generous. Lakefront, preserve, manor or courtyard, each home site offers an impressive setting for magnificent homes rich in detail and craftsmanship.

You are only minutes from the city, but you will not know it until you pass back over the cobblestone bridge and leave through the gates. Waterstone’s stunning natural surroundings offer the ideal setting for the new home you deserve.

These stunning estate homes are priced from $500,000 to several million

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Windermere residents and visitors alike, enjoy swimming, fishing and boating in the cool waters, when not out enjoying the bright lights of Orlando which are just minutes away.

Windermere is ‘on the doorstep’ of the theme parks, shopping malls, world-class restaurants, concert venues and some of the best golf courses in the U.S. including the Jack Nicklaus Signature, Golden Bear Club at Keene’s Pointe, just minutes away. When you wish to stay really local you can visit Main Street which abounds with unique boutiques, roadside cafes and eateries.

Windermere is among America’s top 15% of wealthiest communities and as the numbers of wealthy grow, so does the real estate development at Windermere. With so many affluent families looking for the perfect community, Windermere is happy to oblige within reason. There are a number of prestigious new communities in construction in the Windermere area seeking new families who appreciate the finer things in life.

Windermere also offers several excellent public and private schools from which to choose and ‘NeighborhoodScout’ recently released a special report identifying Windermere as the best town for families and children in Florida.


Windermere has always strived to be self-sufficient and now that confidence has returned to the real estate market, we are seeing new investments which will bolster the community in the future. Prices in Windermere remained strong during the economic meltdown and are now going from strength to strength. If you are looking for a quality residence or fantastic vacation home, which offers privacy, charm and a unique atmosphere then allow us to show you around the best real estate that Windermere has to offer.

Contact us today to schedule the first day of the rest of your life in Windermere.

Looking to buy Orlando Luxury homes for sale but don’t know where to begin? Luxury homes and condos, custom homes and townhouses, lakefront homes, golf front mansions are all here for sale in Windermere Florida.

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Regardless of your budget there is a huge choice of luxury homes for sale in Orlando. Prices are still considerably well below peak levels and we occassionally come across homes that have been discounted by upwards of $1 million dollars. Prestigious communities in the Windemere area such as Isleworth and Bay Hill currently represent some of the best buys in all of Florida.

For more information about what is available please use the form to the right and include your exact criteria in the comments section.

If you have any questions or wish to schedule an appointment use the contact us page or call us directly on (+1) 407-383-1051.

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