10 Things To Know BEFORE Moving to Windermere FL {2025 Guide}

Are you thinking about moving to Windermere, Florida? This charming town in Orange County is a hidden gem, offering a perfect blend of luxury living, small-town charm, and proximity to Orlando’s world-class attractions. Nestled along the stunning Butler Chain of Lakes, Windermere is known for its upscale neighborhoods, top-rated schools, and vibrant community spirit. Whether you’re a family, professional, or retiree, Windermere has something for everyone. In this guide, we’ll share 10 reasons to move to Windermere, from its thriving real estate market to local favorites like the Windermere Brewing Company. As your trusted Windermere realtor, Andy Neal, a local luxury real estate expert, is here to help you find your dream home in this Florida paradise.

10 Reasons to Move to Windermere, Florida

1. Thriving Real Estate Market

Windermere’s real estate market is a major draw for homebuyers seeking luxury and value. The median home price is around $750,000, with options ranging from modern single-family homes to multimillion-dollar lakefront estates. Neighborhoods like Isleworth, Keene’s Pointe, and Lake Butler Sound offer gated communities with amenities like golf courses and private docks. The market is competitive, with homes often selling quickly due to high demand. Whether you’re looking for a cozy home in Windermere Downs (median price: $605,000) or a sprawling estate, Windermere’s diverse inventory has it all. Andy Neal, a Windermere luxury realtor, can guide you through the market and find a property that fits your lifestyle and budget.

2. Top-Rated Schools

Families love Windermere for its exceptional educational opportunities. The town is served by the Orange County Public Schools district, one of Florida’s best, with schools like Windermere Elementary, Gotha Middle, and Olympia High earning high marks for academics and extracurriculars. Private options, such as Windermere Preparatory School, offer prestigious International Baccalaureate programs. For higher education, the University of Central Florida (UCF) is just a 30-minute drive away. With such strong schools, Windermere is a top choice for families prioritizing education. Contact Andy Neal to find a home near the best schools for your children.

3. The Butler Chain of Lakes

Windermere’s crown jewel is the Butler Chain of Lakes, a series of 11 interconnected lakes offering breathtaking views and endless recreation. Residents enjoy boating, fishing, kayaking, paddleboarding, and waterskiing right in their backyard. Public access points like R.D. Keene Park make it easy to launch a boat or relax by the water. Neighborhoods like Windermere Downs even have a lakefront park with a sandy beach and community dock. The lakes create a serene, resort-like atmosphere that makes every day feel like a vacation. Andy Neal can help you find a lakefront home to maximize your waterfront lifestyle.

4. World-Class Golf Courses

Golf enthusiasts will feel right at home in Windermere, which boasts some of Florida’s finest courses. Isleworth Golf & Country Club, a championship course designed by Arnold Palmer, is a favorite among pros and celebrities. Keene’s Pointe, home to a Jack Nicklaus-designed course, offers stunning fairways and lake views. These private clubs provide not only golf but also social events, dining, and fitness facilities. Whether you’re a seasoned golfer or a beginner, Windermere’s courses elevate your game and lifestyle. Let Andy Neal show you homes in golf course communities tailored to your interests.

5. Windermere Brewing Company

For craft beer lovers, the Windermere Brewing Company is a local hotspot that adds to the town’s charm. Located in nearby Winter Garden, this brewery offers a cozy taproom with a rotating selection of handcrafted beers, from IPAs to stouts. It’s a great place to unwind with friends, enjoy live music, or sample seasonal brews. The brewery also hosts events like trivia nights and beer tastings, making it a community hub. After a day of house hunting with Andy Neal, stop by Windermere Brewing Company to experience the local flavor.

6. Vibrant Farmers Market

The Windermere Farmers Market, held every Friday in Town Square, is a beloved tradition that brings the community together. Shop for fresh produce, artisanal baked goods, local honey, and handmade crafts while enjoying live music and a family-friendly atmosphere. The market is a great way to meet neighbors and support local vendors. It’s also a perfect spot to grab a coffee and stroll through downtown Windermere’s tree-lined streets. Andy Neal can recommend homes near the market for easy access to this weekly event.

7. Food Truck Nights

Windermere’s Food Truck Nights add a fun, culinary twist to the town’s social scene. Held regularly at Town Square, these events feature a rotating lineup of food trucks serving everything from gourmet tacos to wood-fired pizzas and decadent desserts. Live music and outdoor seating create a festive vibe, making it a favorite for families and couples. It’s a great way to sample diverse cuisines without leaving town. Ask Andy Neal about upcoming Food Truck Night dates to plan your visit while exploring Windermere homes.

8. Proximity to Orlando Attractions

Living in Windermere means you’re just 10–15 miles from Orlando’s world-famous attractions. Spend a day at Walt Disney World, Universal Studios, or SeaWorld, all within a 15–20-minute drive. Orlando’s vibrant dining, shopping, and nightlife, including spots like Dr. Phillips’ Restaurant Row, are also nearby. Windermere offers the best of both worlds: a peaceful retreat with easy access to urban excitement. Andy Neal can help you find a home that balances tranquility with proximity to Orlando’s hotspots.

9. Safe and Family-Friendly Community

Windermere is one of Florida’s safest towns, with crime rates significantly lower than state and national averages. The town’s small population of about 3,500 fosters a tight-knit, welcoming community where neighbors know each other. Family-friendly amenities, like Tibet-Butler Nature Preserve for hiking and Fernwood Park for picnics, abound. Community events, such as holiday parades and outdoor movie nights, strengthen local bonds. For families seeking safety and connection, Windermere is ideal. Andy Neal can guide you to neighborhoods like Summerport or Reserve at Belmere that cater to family living.

10. Strong Job Market Nearby

While Windermere is primarily residential, its proximity to Orlando provides access to a robust job market. Key industries include tourism (theme parks and hotels), healthcare (AdventHealth, Orlando Health), technology (growing tech hub), and education (UCF, local schools). Orange County’s unemployment rate is around 3.5%, below the national average, and Windermere’s median household income of $125,000 reflects its affluent economy. The average commute to Orlando is 25–30 minutes via highways like SR 429. Andy Neal can help you find a home with convenient access to your workplace.

Cost of Living in Windermere

Windermere’s upscale lifestyle comes with a higher cost of living, but the quality of life justifies the expense. Here’s a breakdown:

• Housing: Median home prices are $750,000, with rentals averaging $2,500–$3,000/month for a three-bedroom home. Luxury estates can exceed $2 million.

• Utilities: Monthly costs for electricity, water, and internet range from $150–$250.

• Groceries: A family of four spends $800–$1,200/month, slightly above the national average.

• Transportation: Gas is about $3.50/gallon, and car ownership is essential due to limited public transit.

• Overall: The cost of living index is 120 (national average: 100), driven by housing.

For help navigating the housing market, contact Andy Neal, who specializes in finding homes that fit your budget and lifestyle.

Pros and Cons of Living in Windermere

Pros

• Safe, family-friendly community with low crime rates.

• Access to the Butler Chain of Lakes for recreation.

• Top-rated schools and private education options.

• World-class golf courses and luxury amenities.

• Proximity to Orlando’s theme parks and entertainment.

Cons

• High cost of living, especially housing.

• Limited public transportation, requiring a car.

• Tourist traffic near theme parks during peak seasons.

• Hurricane risk during June–November.

Moving to Windermere: Tips from Andy Neal

Ready to make Windermere your home? Here are tips from Andy Neal, your Windermere realtor:

• Partner with a Local Expert: Andy’s deep knowledge of Windermere’s neighborhoods, from Isleworth to Windermere Downs, ensures you find the perfect home.

• Visit First: Explore the farmers market, Food Truck Nights, or the lakes to experience Windermere’s vibe. Andy can arrange personalized tours.

• Plan for Costs: Budget for higher housing costs and hurricane preparedness. Andy can suggest affordable neighborhoods like Summerport.

• Connect Locally: Join community events or visit Windermere Brewing Company to meet neighbors. Andy can share upcoming event details.

Final Thoughts

Moving to Windermere, Florida, offers a chance to live in a luxurious, lakefront community with top schools, vibrant local culture, and access to Orlando’s attractions. From the thriving real estate market to the Windermere Brewing Company and weekly farmers market, Windermere blends small-town charm with upscale living. Whether you’re drawn to golf courses, food truck nights, or the serene Butler Chain of Lakes, this town has it all.

Let Andy Neal, your trusted Windermere realtor, guide you to your dream home. With his expertise in luxury real estate and passion for Windermere, Andy will make your move seamless. Contact Andy Neal today to explore Windermere real estate and start your new chapter in this Florida paradise!