Windermere Florida Homes For Sale

Luxury Homes for Sale

Windermere Florida Real Estate

Looking for your Dream Home in Windermere? Contact me with your home specs and together we’ll find your perfect home! See more listings below.

About Windermere, Florida

Windermere, Florida is a picturesque town located in the heart of Orange County, just outside of Orlando. Known for its idyllic natural setting, luxurious homes, and excellent schools, Windermere is a highly sought-after destination for families and professionals alike.

Windermere is known as the Town Among The Lakes. The Windermere or Butler Chain of Lakes is famously composed of thirteen (13) interconnected lakes of varying sizes that flow as far south as the Everglades. The location is also close to historic Winter Garden (listed on the National Registry of Historic Places), championship golf courses, farmers markets, fine shopping and dining. The Orlando International Airport is an easy commute, and Walt Disney World, Universal Studios, and Sea World are just around the corner. Orange County schools include some of Windermere’s finest: Keenes Crossing Elementary, Bridgewater Middle School and Windermere High School.

Windermere Florida Luxury Homes

One of the main draws of Windermere is its location. Situated on the banks of the Butler Chain of Lakes, the town offers residents stunning waterfront views and easy access to boating, fishing, and other water activities. The Butler Chain of Lakes is a 14-lake chain that stretches across the southern part of Orange County, and is considered one of the most picturesque and desirable areas in the area. The town is also home to several parks and nature preserves, including the Windermere Park and Nature Preserve and the world renowned Isleworth Golf and Country Club.

The city of Windermere, Florida, is the prime location for you and your family, being only 30 minutes from Orlando, and about an hour from Daytona's Beaches, this community is a humble one with many scenic natural backdrops surrounding the Lake Butler Chain of Lakes. If you desire a premier luxury home in the inland areas of the city, or along one of the many lakes in the vicinity, then choosing Windermere is the place for you. If you have an inkling for riding through the historic district of Windermere, then you may enjoy some of the many beautiful old-fashioned homes and buildings either by vehicle or bicycle. For more information on Windermere, or its many luxury lakefront and standard luxury homes, please contact us.  

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A Family Friendly Community

For families, Windermere offers excellent schools and a safe and friendly community. The town is home to several top-rated schools, including Windermere Preparatory School and Olympia High School, which are known for their excellent academic programs and extracurricular activities. The town also boasts a low crime rate and a strong sense of community, making it a great place to raise children.

Ideal for Professionals & Retirees

Windermere is also a popular destination for professionals and retirees. The town offers easy access to major highways and is just a short drive from downtown Orlando, making it a convenient location for those who work in the city. Additionally, Windermere is home to several upscale neighborhoods, such as Keene’s Pointe and Isleworth, which offer luxurious homes and amenities to residents. These neighborhoods are known for their beautiful homes and exclusive communities, making them a popular choice for professionals and retirees.

A Rich History

One of the most appealing aspects of Windermere is its sense of history. The town was founded in the late 1800’s by a group of wealthy entrepreneurs and has since grown into a vibrant community with a rich history. The town is home to several historic sites, including the Windermere Union Church, which was built in 1887, and the Windermere Schoolhouse, which is now a museum. The town also hosts several annual events and festivals, such as the Windermere Art Festival and the Windermere Christmas Boat Parade, which celebrate the town’s rich history and community spirit.

Great Restaurants and Shopping

In addition to its natural beauty and rich history, Windermere is also known for its excellent dining and shopping options. The town is home to several popular restaurants, such as The Porch and The Rusty Spoon, which offer a variety of delicious brunch and lunch options.

Only minutes away an area lovingly nicknamed ‘Restaurant Row’ , if you like to dine out, this area will be your new favorite spot. This part of town is home to 16 popular restaurants. This ‘Row’ is a half mile stretch of Sand Lake Road that is filled with great restaurants. Online reviewers brag about the cuisine from Season’s 52, Dragonfly Sushi and Flemings Steakhouse- just to name a few. In fact, many people from other parts of Greater Orlando drive in to frequent this ‘foodie paradise’ because it offers such a large number of dining options , all within a close proximity to each other. You certainly won’t run out of new dishes to try when you close by in Windermere!

Karen loves to support local restaurants by celebrating with her team over dinner. “I love Eddie V’s Prime Seafood. I make a point to try and meet my out-of-state clients at one of the restaurants that is in the area where they are looking to purchase. This way they can get a feel for the community. At the same time, they get to try one of the restaurants that will be close by after they move into their new home.” explains Karen

This Orange County town also boasts several easy to access shopping centers such as the Windermere Village Shopping Center and the Windermere Farmers Market. Whether you feel like staying in or going out for a bite, you have all the options you need when you live in this part of Central Florida.

An Active and Vibrant Community

Despite its quaint size, downtown Windermere is a vibrant and active community. This part of town is home to several active community organizations, including the Windermere Rotary Club and the Windermere Women’s Club, which offer residents a variety of opportunities to get involved and make a difference in the community. Additionally, locals can take advantage of a wide range of recreational activities, such as tennis, golf and swimming, making it a great place to stay active and healthy.

Central Florida Lifestyle

Central Florida is one of the most interesting and inspiring places to live, or even visit as a annual destination. Beautiful breezes, supportive communities and amenities that could put you in paradise, are just some of the key features of this area of Florida. Florida is known around the nation as the sunshine state, and for good reason. Because of the state's close proximity to the Equator, the climate and overall temperatures stay in the 90's in the summer, and cool down to the mid 40's in the winter. With this kind of temperate climate, the opportunities for fun in the sun are endless, with attractions including, Downtown Orlando's Universal Studios, Disney World, Epcot, Wet 'n' Wild, Sea World, and much more to do in the city. Thankfully, central Florida is home of some of the most interesting and affordable luxury homes in the city of Windermere.

Overall, Windermere is a wonderful town that offers residents a unique combination of natural beauty, rich history, and a strong sense of community. Whether you are a family looking for a safe and friendly community or a professional looking for luxury living at its best, Windermere is a great place to call home. With its excellent schools, beautiful homes, and endless recreational opportunities, Windermere is a Florida town that truly has something for everyone.

Featured Listings

Homes for Sale in Windermere, FL

9621 Windy Ridge

WINDERMERE , FL 34786

  • Status: Active
  • Price: $13,950,000.00
  • Square Feet: 20445
  • Bedrooms: 9
  • Bathrooms: 16
  • Price Per Square Foot: $682.32
  • Listing Last Updated:

4200 Down Point

WINDERMERE , FL 34786

  • Status: Active
  • Price: $13,900,000.00
  • Square Feet: 14435
  • Bedrooms: 6
  • Bathrooms: 9
  • Price Per Square Foot: $962.94
  • Listing Last Updated:

9832 Laurel Valley

WINDERMERE , FL 34786

  • Status: Active
  • Price: $13,250,000.00
  • Square Feet: 11100
  • Bedrooms: 6
  • Bathrooms: 10
  • Price Per Square Foot: $1193.69
  • Listing Last Updated:

11301 Bridge House

WINDERMERE , FL 34786

  • Status: Active
  • Price: $11,995,000.00
  • Square Feet: 9267
  • Bedrooms: 5
  • Bathrooms: 9
  • Price Per Square Foot: $1294.38
  • Listing Last Updated:

5507 Worsham Court

WINDERMERE , FL 34786

  • Status: Active
  • Price: $8,650,000.00
  • Square Feet: 10200
  • Bedrooms: 5
  • Bathrooms: 11
  • Price Per Square Foot: $848.04
  • Listing Last Updated:

9313 Tibet Pointe

WINDERMERE , FL 34786

  • Status: Active
  • Price: $7,999,000.00
  • Square Feet: 8792
  • Bedrooms: 6
  • Bathrooms: 8
  • Price Per Square Foot: $909.80
  • Listing Last Updated:

12264 Montalcino

WINDERMERE , FL 34786

  • Status: Active
  • Price: $6,500,000.00
  • Square Feet: 7875
  • Bedrooms: 4
  • Bathrooms: 8
  • Price Per Square Foot: $825.40
  • Listing Last Updated:

11618 Vinci

WINDERMERE , FL 34786

  • Status: Active
  • Price: $6,000,000.00
  • Square Feet: 5260
  • Bedrooms: 5
  • Bathrooms: 6
  • Price Per Square Foot: $1140.68
  • Listing Last Updated:

9139 Tibet Pointe

WINDERMERE , FL 34786

  • Status: Active
  • Price: $5,995,000.00
  • Square Feet: 10341
  • Bedrooms: 6
  • Bathrooms: 9
  • Price Per Square Foot: $579.73
  • Listing Last Updated:

Recent Closings

Sold Homes in Windermere, FL

13772 Summerport Trail

WINDERMERE , FL 34786

  • Status: Sold
  • Price: $423,000.00
  • Square Feet: 2024
  • Bedrooms: 4
  • Bathrooms: 3
  • Price Per Square Foot: $208.99
  • Listing Last Updated:
Karen Arbutine

About Karen Arbutine

Windermere Florida Real Estate Agent


Contact Karen today to embark on the journey of buying or selling a home in Windermere, FL. We offer complimentary consultations and valuations, providing you with valuable insights into the market and the potential value of your property.