Windermere Waterfront Homes for Sale

Exclusive Lakefront Living on the Butler Chain of Lakes

If you’re searching for breathtaking lake views, gated estates, and one of the most prestigious addresses in Central Florida—welcome to Windermere. Nestled among crystal-clear lakes, Windermere offers a rare blend of natural beauty, luxury living, and privacy, just minutes from Orlando’s top golf courses, schools, and attractions.

Discover the finest Windermere waterfront homes for sale today, from grand waterfront mansions to custom lakefront homes with private docks.

Why Choose a Waterfront Home in Windermere?

• Direct access to the Butler Chain of Lakes, one of Florida’s most desirable freshwater systems

• Quiet, upscale neighborhoods with luxury custom builds

• Gated communities offering privacy, security, and resort-style amenities

• Proximity to Disney World, Winter Garden Village, and top-rated Orange County schools

• High property value appreciation and strong long-term investment potential

Top Waterfront Communities in Windermere

Isleworth Golf & Country Club

World-renowned gated community with estate homes along Lake Louise, Lake Chase, and Lake Butler. Offers elite golf, tennis, spa services, and concierge-level security.

Keene’s Pointe

Gated golf and waterfront community with private docks and scenic lakefront lots. Home to The Golden Bear Club and a range of high-end custom homes.

Lake Butler Sound

Guard-gated luxury enclave featuring Mediterranean-inspired estates with serene lakefront views on the shores of Lake Butler.

Glenmuir & Bellaria

Custom lakefront homes in boutique-style gated neighborhoods, perfect for buyers seeking elegance, space, and seclusion.

What You’ll Find in Windermere Waterfront Homes

• Expansive lots with mature landscaping and gated entries

• Unobstructed lake or canal views with western-facing sunset exposure

• Private boat docks, jet ski lifts, and covered boathouses

• Resort-style pools, outdoor kitchens, and entertainment-ready spaces

• High-end finishes, custom architecture, and smart-home upgrades

Things to Do Near Windermere Waterfront Homes

Living lakefront in Windermere means enjoying the best of Florida’s outdoor recreation and upscale conveniences—all just minutes from your door.

Outdoor Activities

• Boating, jet skiing, tubing, and sunset cruising on the Butler Chain of Lakes

• Kayaking and paddleboarding in peaceful coves and canals

• Scenic walking paths, parks, and green space in downtown Windermere

• Championship golfing at Isleworth Golf & Country Club or The Golden Bear Club

• Weekly farmers markets and seasonal outdoor events in the heart of town

Dining & Shopping

• The Grove Orlando – Boutique shopping, salons, and local eateries

• Restaurant Row (Sand Lake Road) – Upscale dining with lake views and international cuisine

• Winter Garden Village – Popular shopping plaza with retail, restaurants, and grocery stores

• Downtown Windermere – Quaint cafes, wine bars, and local favorites

• Easy access to Walt Disney World Resort for dining, entertainment, and nightlife

Work With a Windermere Waterfront Real Estate Specialist

I’m Mike Chen, a local expert in Orlando luxury real estate. I’ve helped discerning buyers find their perfect waterfront home in Windermere—from off-market estates to show-ready listings. With deep local knowledge, negotiation expertise, and an investor’s mindset, I’ll help you make a smart and rewarding move.

• Access to exclusive listings on the Butler Chain of Lakes

• Expertise in lake regulations, dock permits, and flood zone considerations

• Concierge-level service from showing to closing

• 5-star client reviews and proven results in luxury home sales

Let’s Find Your Dream Waterfront Property

Whether you want a quiet retreat with sunset views or an entertainer’s paradise with full lake access, I’ll help you navigate Windermere’s elite waterfront market with ease.

Start your search with confidence.

📩 Schedule a Free Consultation

Let’s discuss your goals!

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Frequently Asked Questions (FAQs)

What is the Butler Chain of Lakes?

A highly sought-after chain of 13 connected lakes offering over 5,000 acres of boating, fishing, and recreation. It’s a top destination for luxury lakefront living in Central Florida.

Can I have a boat dock in Windermere?

Yes. Many lakefront homes feature private docks, and Windermere has clear permitting processes for dock construction and maintenance.

Are there new construction waterfront homes in Windermere?

New builds are limited due to land availability, but you can still find luxury custom homes or renovate existing estates on premium lakefront lots.

What makes Windermere different from other waterfront areas?

Windermere offers a combination of gated communities, top schools, estate homes, and access to one of Florida’s cleanest lake systems—all just minutes from Orlando’s best attractions.