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10 Things to Know Before Moving to Windermere, FL

10 Things to Know Before Moving to Windermere, FL Written by Brittany Slagle

Are you considering moving to a place where upscale living meets small-town charm? Then look no further; Windermere, Florida, is the place for you.

Located in Orange County, this charming city is home to 2,949 people. Windermere is known for its beautiful landscapes, luxurious homes, close-knit community, and excellent schools. It is, however, essential to familiarize yourself with some important aspects of the area before making the move to this city.

Let’s consider 10 things to know before moving to Windermere, FL!

1. Windermere has an upscale community

Windermere boasts an upscale community that attracts residents seeking a luxurious lifestyle. The town is known for its upscale neighborhoods, affluent properties, and elegant custom-built homes. One of the exemplary upscale neighborhoods in Windermere is Keene’s Pointe.

These residences feature stunning architecture, spacious interiors, and amenities such as private pools and waterfront views. Windermere is also home to prestigious golf and country clubs, such as the Isleworth Golf & Country Club, that provide members with access to championship courses, fitness centers, and fine dining experiences.

The town offers upscale shopping options and high-end dining establishments, catering to the tastes of its affluent residents. Noteworthy shopping and dining options are The Market at Windermere and the Vineyard Wine Bar and Healthy Bistro, respectively.

2. Natural beauty surrounds the city

Situated amidst the stunning Butler Chain of Lakes, Windermere boasts breathtaking natural beauty. The area is blessed with picturesque waterways, towering oak trees, and an abundance of lush green.

Windermere is also committed to preserving its natural environment, as evident in its strict building codes and architectural standards. Living in Windermere allows you to immerse yourself in the town’s natural splendor, providing a serene escape from city life and opportunities to appreciate the captivating beauty that surrounds them.

Tibet-Butler Nature Preserve, Lakefront Park, and Isleworth Grove Park are popular nature parks in this city.

3. Residents have a strong community spirit

Windermere prides itself on its strong sense of community, which is evident in the active participation and engagement of its residents. The town organizes various events and initiatives that bring neighbors together, fostering connections and a sense of unity.

Also, the town’s emphasis on education and family values further enhances the community spirit as families come together to support the education and development of children. Windermere’s strong community spirit makes it a place where you’ll feel welcomed and get all the support you need to settle in.

4. Windermere has 7 public schools

Windermere is home to 7 public schools, including elementary schools, middle schools, and high schools. The Orange County Public School District serves the area, offering highly rated educational institutions that prioritize academic excellence, extracurricular activities, and well-rounded education. In addition, there are private schools in this city too.

Overall, Windermere schools are renowned for their excellent performances. Notable schools here include Windermere Elementary School, Horizon West Middle School, and Windermere High School.

5. Enjoy outdoor recreation at Tibet-Butler Nature Preserve

With its prime location surrounded by lakes and parks, outdoor enthusiasts will find Windermere a haven for recreational activities.

A top choice for outdoor activities and nature appreciation in Windermere is Tibet-Butler Nature Preserve. Spanning 440 acres, it offers diverse ecosystems, well-maintained trails, and opportunities for hiking, walking, and birdwatching. You can explore the preserve’s rich biodiversity, including native plants and wildlife.

The preserve also provides picnic areas and shelters, making it a great place for families and groups to enjoy a day in nature. You’d love hanging out here.

6. Windermere is close to downtown Orlando and some major attractions

Windermere is located just a short distance from downtown Orlando. This allows for quick exploration of the city’s lively downtown area, renowned for its culinary scene, nightlife, and cultural attractions.

Additionally, Windermere’s favorable location places it within close reach of world-famous theme parks like Walt Disney World Resort and Universal Orlando Resort. You can enjoy the thrilling rides, enchanting experiences, and magical atmosphere of these renowned destinations.

Overall, Windermere’s location ensures that you can easily access the excitement and entertainment of downtown Orlando and the major attractions in the area.

7. Exclusive Golf and Country Clubs

If you’re a golf lover, then you will be pleased to discover that Windermere is home to several prestigious golf and country clubs. These exclusive clubs offer world-class facilities, championship courses, and a refined social atmosphere for those who enjoy the sport or seek an upscale lifestyle.

Some of the golf clubs that you can join here include the Isleworth Golf & Country Club, Keene’s Pointe Golf Club, Windermere Country Club, and Orange Tree Golf Club.

8. The city has limited commercial development

Windermere maintains limited commercial development to preserve its small-town atmosphere, natural environment, and residential character. The town implements strict zoning regulations to prioritize low-density residential areas and control commercial growth. This approach helps protect the picturesque lakes, green landscapes, and serene surroundings that define Windermere.

While commercial options within Windermere are limited, residents have access to a range of amenities in nearby urban areas like Orlando and Winter Garden. Windermere also supports local businesses that align with the community’s values, fostering a unique shopping experience. 

Overall, Windermere’s limited commercial development strikes a balance between meeting residents’ needs and preserving the town’s distinctive ambiance.

9. Windermere’s living expenses are 43% higher than the U.S. average

Living in Windermere comes with a higher cost of living compared to other areas in Florida. The cost of living here is 43% higher than the national average. The luxurious homes, exclusive amenities, and desirable locations contribute to the elevated cost of housing, goods, and services.

Groceries are 3% higher than the national average; a loaf of bread costs $4.00, a gallon of milk is sold for $2.50, and a hamburger is sold for $5.38. Transport expenses are also higher than the national average by 1%. The housing cost is much higher than the national average; the median home price is $666,339.

Utility and healthcare costs are, however, less than the national average by 7% and 9%, respectively. Living in Windermere is quite expensive, and it is important to consider this aspect when planning your budget.

10. Windermere has strict building codes and architectural standards

Windermere has established strict building codes and architectural standards to preserve its unique character and aesthetic appeal. These regulations are designed to ensure that new construction and renovations align with the desired aesthetic, blend seamlessly with existing structures, and maintain the town’s historic character.

The guidelines cover aspects such as architectural styles, materials, design elements, setbacks, lot sizes, landscaping, and building materials and finishes. Windermere’s review and approval process ensures that construction projects comply with these standards.

If you plan on building or renovating a property, be prepared to comply with these regulations to maintain the town’s visual harmony.


Moving to Windermere promises a high-quality lifestyle in a beautiful setting, with a close-knit community, upscale neighborhoods and a range of recreational opportunities at your doorstep. You should, however, weigh the drawbacks, such as the high cost of living, limited commercial development, strict building codes, and architectural standards before making the move to Windermere, FL!

Learn More About Living in Windermere, FL

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