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Windsor Cay Realtor You Can Trust — From Disney Dreams to Investment Wins

Your Inside Connection to Windsor Cay

Thinking about buying or selling in Windsor Cay? 

I’m Mike Chen, your go-to Windsor Cay Realtor, and someone who knows this magical community not just as an agent—but as a fellow vacation homeowner, investor, and local expert. I’m here to guide you with real insight, real experience, and real results.

Why Windsor Cay Feels Like Home (Even If It’s Your Investment Property)

Our family’s story began with a trip to Walt Disney World. My kids called it the “Best Day Ever,” and that sparked a dream—to create vacation homes where other families could make those same magical memories. 

Since then, I’ve owned and operated multiple vacation homes across the Windsor communities, each one designed to deliver joy, value, and comfort.

Windsor Cay is the newest jewel in this resort crown—with world-class amenities, new-build homes, and unbeatable proximity to Disney. 

Whether you’re building your real estate portfolio or finding a vacation home that doubles as a smart investment, Windsor Cay is a place where both hearts and spreadsheets agree: it’s a win.

So what makes Windsor Cay such a standout in the Orlando vacation home market? Let’s break it down by location and resort perks.

Windsor Cay Resort Location Highlights

  • 8 miles to Walt Disney World (15 min)
  • 22 miles to Universal Orlando
  • 20 miles to Epic Universe (opening 2025)
  • Close to Cagan’s Crossing shops & dining
  • 40 minutes to Orlando International Airport
  • 12+ golf courses within 10 miles
  • 35 minutes to premium outlet shopping
  • 60 minutes to Port of Tampa
  • 90 minutes to Port Canaveral Cruise Terminal

Easy access to new high-speed rail (Miami to Orlando)

Top-Tier Resort Amenities

  • Full Bar & Café
  • Community Room for Meetings/Events
  • 24-Hour Manned Gated Entry
  • Fitness Center & Sports Courts
  • Water Slides, Lazy River, Splash Pad
  • Full-Service Concierge
  • Kids’ Playground

Why I Chose Windsor Cay—And Why You’ll Want Me in Your Corner

I’m not just a Realtor—I’m a vacation home owner, Airbnb Superhost, and the founder of FunStay Florida Vacation Homes. With over a decade in real estate investing and property management, I’ve walked in your shoes.

Whether you’re an out-of-state buyer, a first-time investor, or a seasoned owner looking to sell at peak value, I know how to guide you through every step—from choosing the best lot to designing a guest-ready listing that gets booked solid.

Here are just a few ways I can help as your Windsor Cay buyer’s agent:

  • Help you locate the best vacation home community that fits your budget and goals
  • Connect you with trusted partners for design and furniture packages
  • Recommend the best local property managers for hands-off income
  • Assist with setting up your Airbnb account and listing your home
  • Share tips on how to maximize your bookings from day one
  • Offer my hands-on experience as a vacation home owner of 9 units and operator of a successful Orlando booking company
Mike Chen Realtor
Mike Chen Realtor

From Dream to Doorstep: Helping You Buy in Windsor Cay

Buying in Windsor Cay isn’t just about signing paperwork. It’s about:

  • Finding the floorplan that fits your goals (5-10 bedrooms available!)
  • Navigating builder contracts with confidence
  • Choosing the right furniture packages and theming that boost bookings
  • Setting up your listing for Airbnb and VRBO success

When you work with me, you’re tapping into years of insider knowledge that turns your dream into a profitable, joyful reality.

Windsor Cay Resort Floorplans

Windsor Cay Homes For Sale Castaway
Windsor Cay Townhome Castaway

5 Bed/4.5 bath/ 2271 sq.ft/ Pool
Pricing / Fees

Windsor Cay Windston Model
Windsor Cay Windston Model

5 Bed / 4 Bath / 2490 sq.ft / Pool
Pricing / Fees

Windsor Cay Lakeshore
Windsor Cay Lakeshore Model

5 Bed / 4.5 Bath / 2587 sq.ft / Pool
Pricing / Fees

Windsor Cay Resort Hideaway
Windsor Cay Resort Hideaway

5 Bed/4Bath/2490 sq.ft / Pool
Pricing / Fees

Windsor Cay Resort Seashore
Windsor Cay Resort Seashore

7 Bed / 5.5Bath / 3281 sq.ft / Pool
Pricing / Fees

Windsor Cay Resort Baymont
Windsor Cay Resort Baymont

8 Bed / 6 Bath / 4,034 sq.ft / Pool
Pricing / Fees

Windsor Cay Clearwater
Windsor Cay Clearwater

9 Bed / 6 Bath / 4393 sq.ft / Pool
Pricing / Fees

Windsor Cay Clearwater Grand
Windsor Cay Clearwater Grand

10 Bed / 8 Bath / 4393 sq.ft / Pool
Pricing / Fees

GET IN TOUCH

Selling a Home in Windsor Cay? Let’s Maximize Every Dollar

Selling here takes more than a sign in the yard. It takes strategy.

I offer:

  • Targeted pricing based on Windsor-specific trends
  • Professional media: drone, video tours, and 3D walkthroughs
  • Exposure on 100+ platforms
  • Investor and buyer networks that are already looking

As someone who owns and manages homes just like yours, I know what buyers want—and how to position your property so it stands out and sells smart.

Stories from Families, Flippers, and Vacation Dreamers

Mike Chen really lives up to his review and amazing. I am an out of state buyer and you know how hard it is to not be there to see and evaluate the properties. But Mike made it so easy for us. He is extremely responsive, knowledgeable, thorough, and goes above and beyond. He really knows the market and has a strong network. He took away all worries and almost like a family member looking out for you. He made it seem we were there even though we were across the country. I would highly recommend him.

Mike Chen really lives up to his review and amazing. I am an out of state buyer and you know how hard it is to not be there to see and evaluate the properties. But Mike made it so easy for us. He is extremely responsive, knowledgeable, thorough, and goes above and beyond. He really knows the market and has a strong network. He took away all worries and almost like a family member looking out for you. He made it seem we were there even though we were across the country. I would highly recommend him.

Mike Chen really lives up to his review and amazing. I am an out of state buyer and you know how hard it is to not be there to see and evaluate the properties. But Mike made it so easy for us. He is extremely responsive, knowledgeable, thorough, and goes above and beyond. He really knows the market and has a strong network. He took away all worries and almost like a family member looking out for you. He made it seem we were there even though we were across the country. I would highly recommend him.

I’m Just a Call or Text Away—Let’s Chat

Ready to explore Windsor Cay or sell your home for top value? 

📞Text or call me directly at 503-888-8070, or email Mike@MikeChenRealtor.com.

No pressure. No fluff. Just honest answers, expert guidance, and a local partner who gets what makes Windsor Cay so special.


Your Go-To Windsor Cay Realtor for Buying or Selling Smart

Whether you’re buying your first vacation rental or selling a home in Windsor Cay, I’m here to help you win with confidence.

📍Let’s write your next chapter in the happiest place near Earth.

Frequently Asked Questions

What types of homes are in Windsor Cay?

New-build townhomes and single-family homes with 5 to 10 bedrooms, many with private pools.

How fast can you sell my Windsor Cay property?

Homes priced right and marketed well often sell within 1–3 weeks. I use data-driven strategy and high-exposure marketing to make that happen.

Do I need to be in Florida to buy or sell with you?

Nope! I work with out-of-state buyers and sellers all the time—virtual showings, digital docs, and local coordination make it seamless.

Can I buy a Windsor Cay home as an out-of-state investor?

Yes — I work with remote buyers all the time and handle everything locally on your behalf.

What’s your experience with Windsor Cay homes?

I’m not just a Realtor—I’m a Windsor community homeowner, investor, and Airbnb Superhost with years of firsthand experience.

Do you manage vacation rentals too?

Yes, I co-own FunStay Florida and can either manage it or connect you with trusted local partners.