Discover Lake Cawood Estates—Windermere’s hidden gem offering spacious luxury, serene surroundings, and proximity to Disney magic without the crowds. 🌳🏡✨

Touring Lake Cawood Estates: Peaceful Luxury Hidden in Windermere

Welcome to Tour Tuesday, where we explore exceptional neighborhoods near Walt Disney World that offer more than convenience…they offer a complete lifestyle.

Today, we’re heading to a quiet, upscale pocket of Windermere that’s a hidden gem even among locals:

Lake Cawood Estates

This small, gated community offers elegant custom homes, tranquil lake views, and all the privacy you could want—just minutes from the magic.


📍 Where Is Lake Cawood Estates?

Tucked along Winter Garden Vineland Road, Lake Cawood Estates is situated between Windermere Prep and downtown Windermere, with easy access to:

  • 🏰 Walt Disney World – ~20 minutes to the front gates
  • 🛍️ Winter Garden Village – 10 minutes
  • 🏫 A-rated schools like Windermere High and Windermere Prep
  • 🌴 Butler Chain of Lakes recreation
  • 🚗 Easy routes to Horizon West, Hamlin, and downtown Orlando

It’s perfectly positioned to balance quiet retreat with modern convenience.


🏘️ What Makes Lake Cawood Estates Unique?

This isn’t a massive master-planned development.
It’s a boutique, gated enclave of luxury properties…each one custom-built and generously sized.

🏡 Features include:

  • Estate-style homes ranging from 3,500–7,000+ sq ft
  • Oversized half-acre+ lots with mature landscaping
  • Stunning lakefront and conservation views
  • 3- to 6-car garages, pool homes, and true indoor/outdoor living
  • Mediterranean, Traditional, and Transitional architectural styles

🧱 Many homes were built in the early 2000s, giving the neighborhood a mature, established feel—not a cookie-cutter aesthetic.

💰 Prices generally range from $1.3M to over $2.5M, depending on size, view, and upgrades.


🌳 Lifestyle & Amenities

Lake Cawood Estates is for those who value peace, privacy, and proximity to the things that matter most.

What you’ll love:

  • Gated entry for security and exclusivity
  • Private lake access for kayaking, paddleboarding, and serene sunset views
  • No through traffic…perfect for quiet walks and bike rides
  • Low HOA compared to similarly sized luxury communities
  • Minutes from world-class golf, dining, and shopping options in Windermere and Hamlin

This is luxury without the noise, built for people who value calm, connection, and character.


💬 What Locals Are Saying

“We wanted space for our kids to grow, but we didn’t want to give up the magic. This was the answer.” – Sarah H.

“It’s the kind of neighborhood you don’t stumble upon…you’re referred here by someone who knows.” – David and Liza F.

“We can host pool parties, watch the fireworks in the distance, and hear the birds every morning. It’s everything we wanted.” – Nora T.


If your ideal day starts with sunlight on the lake and ends with fireworks in the distance, all from the peace of your own private retreat…

Then Lake Cawood Estates might be your dream address.