Welcome to Windermere

Impressive homes and a luxurious lifestyle await.

Windermere is one of Orlando’s exclusive communities, tucked away in a quiet area that beckons residents to experience peace and tranquility. With stunning gated residential areas and a beautiful chain of lakes, Windermere is ideally removed from it all while still offering locals access to the best of everything that the Orlando area is known for. Luxurious and stately, Windermere is still inviting and friendly, with locals who are eager to answer any question and welcome new residents to the area with open arms.

What to Love

  • Stunning architecture
  • A peaceful vibe
  • Top-rated schools
  • Elite and extravagant

Local Lifestyle

As one of the oldest established communities in the Orlando area, Windermere is prestigious and popular. Real estate here goes quickly, with so many people eager to experience the historic vibe and elegant homes in Windermere. Residential amenities in Windermere are top-of-the-line, with excellent schools, well-appointed common areas, and lots of exciting festivals and parades that incite and encourage community spirit. Plus, living in Windermere offers locals easy access to the abundant upscale shopping and restaurants that Orlando features.

Dining, Entertainment, & Shopping

Windermere is close to the Butler Chain of Lakes, a beautiful, scenic outdoor destination perfect for watersports and fishing. Many guests travel to this lake chain to take photos and enjoy the area’s peace and tranquility.

Golf enthusiasts will love the inviting vibe and the upscale amenities at the Golden Bear Club, a private country club that features a golf course designed by sports legend Jack Nicklaus. There’s also a luxury clubhouse, perfect for unwinding before or after your stint on the course. Isleworth Golf & Country Club is another popular country club in the Windermere area. With incredible facilities, a divine restaurant, and architecture that defies description, this country club is a top choice for special events in addition to golf excursions.

There are lots of charming restaurants in Windermere. While Yellow Dog Eats might be a casual eatery on the outside, this American-style restaurant serves up some of the best barbecue in Florida, including brisket, ribs, and pulled pork. Fleming’s Prime Steakhouse & Wine Bar is a fabulous high-end steakhouse well-known for its hand-cut steaks and tender, delicious lobster tails. Don’t miss the decadent desserts, which change based on the season and are the perfect way to end a fantastic meal. For breakfast, check out the Dixie Cream Cafe. This bright, charming cafe is known for its fluffy pancakes, tender omelets, and homemade cake.

The Mexican Camel is a unique restaurant offerings in Orlando that allows guests to build their own bowls from an expansive array of fresh vegetable and protein options. The vibrant interior decor will make you feel at home as you indulge in a delicious meal that conjures up images of Old Mexico. Regardless of your meal preferences, the Windermere area has something to satisfy.

Things to Do

Community spirit is encouraged in Windermere, with special events and festivals that encourage residents to get out and meet their neighbors. The Windermere Farmers Market is a local event that brings out vendors eager to showcase their wares. You’ll find anything from baked goods and handmade jewelry to fresh produce and hand-squeezed lemonade here. For divine music and conviviality, head out to Music Among the Lakes. This annual event features music from the Orlando Philharmonic Orchestra and the Florida Symphony Youth Orchestra and is free for Windermere residents.

Light Up Windermere is a great way to celebrate the spirit of the season. The biggest food truck event of the year, Light Up Windermere takes place every November at the Windermere town hall. Here, you’ll discover some truly delicious goodies from the area’s best-loved food trucks and vendors and marvel at the light displays that make Windermere come alive with the holiday spirit. Outside Windermere’s city limits, there’s more to see, do, and enjoy. Restaurant Row offers some of the most upscale dinings in the state, with steakhouses, seafood eateries, and decadent pastry shops.


Work With Us

The Tate Advisory Group is ready and willing to assist you with all of your real estate needs. Contact us today to get started with your home buying or selling process!

Tate Advisory Group




(407) 476-8855



The Tate Advisory Group is a team of real estate agents affiliated with Compass. Compass Florida, LLC d/b/a Compass is a licensed real estate broker and abides by equal housing opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit propertyalready listed. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

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