The 2026 buyer’s guide to the most desirable communities in Windermere, Florida.

Windermere isn’t just a place… it’s a feeling.

Tree-lined streets, shimmering lakes, luxury estates, golf courses, gated communities… and that peaceful, upscale lifestyle that’s minutes from Walt Disney World but feels like a world of its own.

If you’re searching for the most prestigious, private, and beautiful neighborhoods near the magic, Windermere is the gold standard.

This guide breaks down the top Windermere neighborhoods so you can compare lifestyle, home styles, amenities, and which community fits your dream life.

Let’s explore the best of the best.

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⭐ 1. Keene’s Pointe

The crown jewel of Windermere living.

Keene’s Pointe is one of Windermere’s most celebrated communities, known for:

• Guard-gated privacy
• A Jack Nicklaus-designed golf course (The Golden Bear Club)
• Gorgeous lakefront estates
• Family-friendly streets + parks
• Country club lifestyle
• Mature trees and natural beauty

Who it’s best for

Buyers seeking top-tier luxury, golf lovers, lakefront seekers, and anyone wanting the “classic Windermere” experience.

Why buyers love it

Keene’s Pointe feels peaceful, upscale, and perfectly maintained… with some of the most beautiful streets in Central Florida.

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⭐ 2. Windermere Trails

Modern, convenient, and close to everything.

Windermere Trails sits on the east side of Windermere, offering:

• Newer homes (2013+)
• Community pool + splash pad
• Walking trails
• Easy access to Lakeside Village shopping
• Quick drive to Disney via Reams Road

Who it’s best for

Families, Disney professionals, and buyers wanting newer homes without a luxury price point.

Why buyers love it

It delivers modern comfort, great schools, easy errands, and quick Disney access.

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⭐ 3. Lakes of Windermere

Charming architecture + strong community feel.

This neighborhood features:

• Craftsman-style homes
• Front-porch living
• Community pool + parks
• Walking trails and ponds
• Easy access to shops and dining

Who it’s best for

Buyers who value community feel, neighborly energy, and walkability.

Why buyers love it

It’s picture-perfect, friendly, and has that “storybook Florida neighborhood” charm.

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⭐ 4. Isleworth

Ultra-luxury living at its finest.

Isleworth is nationally recognized and features:

• 24/7 guard-gated estate living
• World-class golf
• Private lakes + boat docks
• Celebrity residents
• Architectural masterpieces

Who it’s best for

Buyers seeking elite, first-class luxury with absolute privacy and security.

Why buyers love it

It’s simply one of the most luxurious communities in Florida… a true status address.

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⭐ 5. Summerport

Beautiful lake views + accessible price points.

Summerport is a large, established community offering:

• Lakeside walking paths
• Multiple parks and playgrounds
• Community clubhouse & pool
• Good schools
• Mix of single-family homes and townhomes

Who it’s best for

Families and buyers wanting great community amenities without luxury pricing.

Why buyers love it

It balances affordability, natural beauty, and convenience.

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⭐ 6. Reserve at Lake Butler Sound

Elegant, gated living on the Butler Chain of Lakes.

This is one of Windermere’s most exclusive neighborhoods, known for:

• Guard-gated privacy
• Custom luxury homes
• Lakefront estates
• Beautiful landscaping

Who it’s best for

High-end luxury buyers wanting pristine, peaceful surroundings.

Why buyers love it

It offers exclusivity, prestige, and stunning lake access.

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⭐ 7. Lake Cypress Cove

Quiet sophistication with natural surroundings.

A smaller gated community featuring:

• Custom homes
• Large lots
• Easy access to major roads
• Peaceful, secluded living

Who it’s best for

Buyers wanting luxury in a smaller, private setting.

Why buyers love it

It’s one of Windermere’s “hidden gems” with gorgeous homes and low traffic.

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⭐ 8. Windermere Downs

A rare blend of privacy, personality, and lake access.

Windermere Downs is beloved for:

• Larger lots
• Mature landscaping
• Unique home styles
• Private community boat ramp
• Lake Crosse access

Who it’s best for

Buyers craving space, charm, and a non-cookie-cutter neighborhood.

Why buyers love it

It feels peaceful, natural, and beautifully tucked away.

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⭐ 9. Tildens Grove

Elegant, spacious, gated, and family-friendly.

Tildens Grove offers:

• Luxury lakefront homes
• Quiet, well-managed community
• Wide streets and green space

Who it’s best for

Families wanting a safe, upscale gated community with room to grow.

Why buyers love it

It’s beautiful, spacious, and located near schools and conveniences.

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⭐ 10. Bellaria

Exclusive, guard-gated, and architecturally stunning.

Bellaria is known for:

• Estate-level luxury
• European-inspired architecture
• Custom homes on oversized lots
• Elegant landscaping

Who it’s best for

Buyers seeking true estate living in a private, elegant environment.

Why buyers love it

It’s breathtaking… and incredibly prestigious.

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🗺️ Which Windermere Neighborhood Is Right for You?

Every Windermere neighborhood has its own personality.
Your perfect fit depends on:

• Your budget
• Your lifestyle
• Your priorities
• Your commute needs
• Your Disney proximity goals
• How you want your everyday life to feel

And that’s where having a local, strategic, buyer-focused guide makes all the difference.

You don’t have to figure it out alone… and you shouldn’t.
Windermere is full of nuance, hidden gems, and opportunities you might never find on a map.

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✨ Ready to Find the Perfect Windermere Neighborhood?

Windermere has some of the most beautiful communities in Central Florida… and I’d love to help you explore them with confidence.

👉 Schedule your Disney Bubble Relocation Strategy Call
Let’s compare neighborhoods, narrow down your best matches, and create a clear plan for your move.