Luxury, Lakes and Laid-Back Magic Just Minutes From Disney
Welcome to Windermere… the lakeside, oak-lined, sunset-soaked jewel of the Disney Bubble.
If Horizon West is the vibrant newcomer and Winter Garden is the charming small town, Windermere is the quiet, elegant, deeply coveted retreat where every day feels peaceful, intentional and… honestly… a little enchanted.
This is where the Butler Chain of Lakes wraps around stately streets, Spanish moss sways above winding sidewalks, and some of Central Florida’s most beautiful homes catch golden light every evening.
When people dream of luxury near Disney…
When they crave space, beauty, privacy and proximity…
Windermere is always near the top of the list.
Let’s explore what makes this community feel magical.
🌟 The Overall Vibe and Windermere Lifestyle
Windermere is the sophisticated side of the Disney Bubble.
It’s quiet.
It’s refined.
It’s mature in the best possible way.
Imagine:
- Beautiful neighborhoods framed by towering oak trees
- Winding roads with lake views at every turn
- Golf carts humming down streets on Saturday mornings
- Neighbors waving during sunset walks
- A peaceful, upscale energy that feels calm and welcoming
Windermere is built for people who want the luxury of space and the ease of Disney access without the bustle of busier suburbs.
It’s timeless… elegant… and full of little moments of magic.
🏡 Types of Homes and Price Ranges
Windermere is known for its high-end real estate.
It is one of Central Florida’s most prestigious places to live.
🏰 Luxury Estates
Gated communities, custom architecture, private docks and lakefront views.
Range: 2M to 12M+
🏡 Executive Homes
Beautiful single-family homes in established neighborhoods.
Range: High 700s to 1.7M+
🏘 Townhomes
Rare but available in a few clusters, offering low-maintenance luxury living.
Range: Low to mid 500s
🌅 Lakefront Homes
Windermere is famous for these.
Butler Chain of Lakes frontage is the crown jewel.
Range: 3M to 12M+
🔒 Gated Communities
Windermere has some of the most exclusive gated neighborhoods in the region, including:
- Isleworth
- Keene’s Pointe
- Waterstone
- Casabella
- Reserve at Lake Butler Sound
Privacy, prestige and postcard views… everywhere.
🏫 Schools and Education
Windermere is home to excellent schools that attract buyers from all over the country.
Highly rated options include:
- Windermere High School
- Windermere Elementary
- Gotha Middle School
- Sunset Park Elementary
- Windermere Preparatory School (private, world-class reputation)
Families relocating here are drawn by the combination of elite schools, safe neighborhoods, lake lifestyle, and Disney proximity.
🚗 Commute and Accessibility
Windermere offers surprisingly easy access to major areas while maintaining its peaceful charm.
To Magic Kingdom
8 to 15 minutes depending on your neighborhood
To EPCOT
15 minutes
To Hollywood Studios and Animal Kingdom
15 to 20 minutes
To Disney Springs
20 minutes with scenic routes available
To Universal
18 to 25 minutes
To Downtown Orlando
20 to 30 minutes
Windermere feels tucked away… yet perfectly connected.
🍽️ Local Perks: Dining, Shopping and Hidden Gems
Windermere’s charm comes from quality over quantity.
The town offers boutique experiences, scenic moments and upscale touches rather than big commercial corridors.
☕ Coffee Shops and Breakfast Spots
- Paloma Coffee Co.
- Allen’s Creamery and Coffee House
- Foxtail Coffee (nearby)
Perfect for morning walks and quiet work sessions.
🍽 Great Restaurants Nearby
Not all within Windermere’s tiny border, but extremely close:
- Big Fin Seafood Kitchen
- Hawkers
- The H Cuisine
- Urbain 40 Brasserie
- Bosphorous
- Toasted
- The Bend (Horizon West border)
Foodies LOVE living this close to the Restaurant Row scene.
🛍️ Shopping
Windermere intentionally keeps its core quaint and charming.
For bigger shopping:
- Winter Garden Village
- Hamlin in Horizon West
- Dr. Phillips shopping district
- The Grove
Everything is within a 10 to 20 minute drive without ever feeling congested.
🌅 Outdoor Lifestyle and Natural Beauty
Windermere is pure outdoor magic.
🌊 The Butler Chain of Lakes
A boater’s paradise.
One of the most beautiful freshwater lake systems in Florida.
Perfect for:
- Waterskiing
- Wakeboarding
- Kayaking
- Sunset cruises
- Lake hopping
🌳 Parks and Trails
- Fernwood Park
- Palmer Park
- Lake Street Park
- Tibet-Butler Nature Preserve (nearby)
- Lakeside walking paths everywhere
🏌️ Golf
Windermere is golfer heaven.
Nearby courses include:
- Isleworth Country Club
- Keene’s Pointe’s Jack Nicklaus-designed course
- Orange County National
- Disney’s Magnolia and Palm (short drive)
Windermere blends peaceful nature with upscale recreation in a way few communities can.
🏘 Notable Neighborhoods in Windermere
🌟 Isleworth
Ultra exclusive. Celebrity residents. Lakefront estates. Private golf. Peak luxury.
🌊 Keene’s Pointe
Gorgeous homes, golf course, lakes and a strong sense of community.
🌿 Reserve at Lake Butler Sound
Gated, elegant, stunning architecture, lush landscaping.
🌞 Windermere Trails
Perfect for families. Parks, pools, amenities, easy access.
🌼 Lakes of Windermere
Charming, friendly, great amenities and quick access to dining and shopping.
🍃 Waterstone
Prestige, privacy and absolutely stunning homes.
🌲 Belmere
European-inspired architecture, gated entry, central location.
Windermere offers the most curated neighborhood selection in all of the Disney Bubble.
💰 HOAs, Taxes and Cost of Living
Windermere leans upscale.
Most communities have HOAs, especially the gated ones.
Typical benefits include:
- Beautiful landscaping
- Community security
- Amenities
- Luxurious entrances and common areas
- Lake maintenance (in some communities)
Taxes are competitive for the region and Florida’s no state income tax is a big perk for relocating professionals and retirees.
Windermere’s cost of living is higher than nearby towns, but it’s directly tied to its exclusivity, lake access and prestige.
🌟 Who Windermere Is Perfect For
🏰 Luxury Buyers
If you’re upsizing, seeking resort-level living or craving privacy, this is your dream.
🌅 Empty Nesters and Retirees
Quiet streets, stunning water views and peaceful energy.
👨👩👧 Families Wanting the Best Schools
Elite schools in a safe, beautiful environment.
🎢 Disney Devotees
Imagine being able to see fireworks on your evening walk.
🌴 Lifestyle-Driven Relocators
People who want peace, beauty, walkability and thoughtful community design.
💼 Executives and Remote Professionals
Windermere offers the space and serenity needed for high performance.
Windermere is the elevated side of the Disney Bubble lifestyle.
🌈 Final Thoughts: The Magic of Windermere
Windermere feels like stepping into a postcard where nature and luxury coexist perfectly.
It’s:
- Calm
- Beautiful
- Prestigious
- Quiet
- Mature
- Lake-filled
- Warm
And… it’s minutes from the most magical place on earth.
This is the Disney Bubble community for people who want a life that feels intentional, peaceful and full of joy.
If your heart lights up at the idea of sunset lake walks, tree-lined streets and a life where the parks are close but peace is closer… Windermere might be your happily ever after.
⭐ Ready to Explore Windermere Homes?
If Windermere is calling your name, I would love to be your guide.
👉 Schedule your Disney Bubble Buyer Consultation today.
Let’s find your dream home near the magic.
I’m Timothy Carter, your dedicated Disney World Orlando area relocation expert with The Funk Collection brokered by eXp Realty.
I specialize in helping Disney lovers & theme park enthusiasts find their perfect home or vacation investment property. I’m here to help turn your dreams into reality!
You’ll find everything you need to know about living in the greater Orlando area – from neighborhood guides, real estate tips & the lifestyle of living near the theme parks, to insider advice on relocating to this magical place.
My family moved to Orlando to LIVE the ultimate Disney lifestyle!
You can too! I can help! Click here —-> Meet With Timothy Carter

