Windward Cay RESIDENTIAL HOMES FOR SALE

Tired of crowded, cookie-cutter developments with tiny yards and sky-high HOA fees? Windward Cay in Winter Garden offers something you don’t find everywhere—spacious homes, scenic views, and a prime location tucked away from the chaos.

Why Windward Cay Stands Out

✔ Spacious Homes Built to Last – Ranging from 2,300 to 3,800 square feet, these 3 to 5-bedroom homes offer plenty of room to live, work, and entertain.

✔ No Overcrowded Neighborhood Vibes – You’re not packed in like sardines. Larger lots, mature landscaping, and peaceful streets make this feel like home.

✔ Homes with Character, Not Cookie-Cutter Boxes – These homes have unique designs, quality craftsmanship, and thoughtful layouts—not just another row of identical houses.

✔ Scenic Views & Green Spaces – Many homes back up to conservation areas, giving you beautiful backyard views and extra privacy.

✔ Minutes from Everything – Shopping, dining, and entertainment at Winter Garden Village are just 2 miles away, plus you have easy access to SR-429 and the Florida Turnpike.

✔ Parks & Outdoor Fun Nearby – Braddock Park and George Bailey Park are just minutes away, offering sports fields, playgrounds, and picnic areas.

✔ Near Top-Rated Golf Courses – If you love to golf, you’re close to West Orange Country Club and Stoneybrook West Golf Club.

What You Need to Know Before Buying Here

📌 HOA Fees Exist, But They’re Reasonable – Unlike some new developments, the HOA here is manageable. However, it’s always good to check the latest fees.

📌 Zoning for Schools Can Change – Windward Cay falls under Orange County Public Schools, including Keene’s Crossing Elementary, Bridgewater Middle, and Windermere High School—but it’s smart to confirm school zoning before buying.

📌 The Commute is Convenient, But Check Traffic – If you work in downtown Orlando, Lake Nona, or the Disney area, make sure to check traffic patterns before committing.

Why Savvy Buyers & Investors Love Windward Cay

🏡 Home Values Are Rising – Winter Garden continues to grow and appreciate, making this a smart long-term investment.

📈 Smaller, Well-Kept Communities Hold Value – Unlike massive developments where homes lose uniqueness over time, Windward Cay’s charm and exclusivity help maintain high resale values.

💰 More Space, Less Competition – If you’re tired of losing bidding wars in newer developments, this low-inventory, high-demand area might be your best bet.

🚗 Easy Access = High Buyer Interest – Being close to 429, Turnpike, and Hamlin Town Center means homeowners here always have buyer demand when they decide to sell.

Thinking About Buying or Selling in Windward Cay? Let’s Talk Strategy

I’m Mike Chen, and I specialize in finding buyers the right home before it’s gone and helping sellers maximize their property’s value.

🔹 For Buyers – Homes in Windward Cay don’t hit the market often. I’ll help you find hidden opportunities and negotiate a strong deal.

🔹 For Sellers – With low inventory and high demand, I’ll make sure your home gets top-dollar offers fast.

🔹 For Investors – This community’s strong resale value and desirable location make it a great long-term investment.

Don’t Wait—Here’s Why Acting Now Is Key

• Homes Here Sell Fast → With limited inventory, if you wait, someone else will grab it.
• Winter Garden’s Market is Heating Up → Every year, prices go higher—buying now means locking in your value early.
• Interest Rates Can Shift Anytime → Even a small rate increase can make a big difference in your monthly mortgage.

Windward Cay is a Rare Find—If You See a Home Here, Don’t Hesitate

Looking for luxury homes or new construction in Winter Garden? I can help. Let’s find the perfect property for you—whether it’s your forever home or your next big investment.

This small, exclusive community gives you privacy, space, and a prime location—a combination that’s hard to come by.

📩 Schedule a Free Consultation

💡 Make a Smart Move. Sell for More. Buy Right.

📞 Call or text me now—let’s make it happen.

TOP NEIGHBORHOODS NEAR WINDWARD CAY IN WINTER GARDEN:

Amberleigh / Bay Isle At Black Lake / Black Lake Park / Brandy Creek / Cambridge Crossing / Carriage Pointe / Cobblestone of Winter Garden / Crown Point Springs / Daniels Crossing / Daniels Landing / Deerfield Place / Edgewater Beach / Emerald Ridge / Foxcrest / Fullers Crossing / Glynwood / Grove Park At Stonecrest / Grovehurst / Independence / Island Pointe / Isles of Lake Hancock / Johns Landing / Johns Lake Point / Lake Cove Pointe / Latham Park / Oakglen Estates / Orange Cove / Orchard Hills / Park Avenue Estates / Regal Pointe / Regency Oaks At Stone Crest / Shadow Lawn / Southern Pines Condominiums / Verde Park / Waterleigh / Watermark / Westfield Lakes / Winter Garden Shores / Wintermere Harbor / Wintermere Pointe

THINGS TO DO IN WINDWARD CAY 

Discover Local History at the Central Florida Railroad Museum / Attend Fridays on the Plaza / Experience Local Art at the SoBo Art Gallery / Unwind at The Grove Resort & Water Park / Unwind at Newton Park / Explore the West Orange Trail / Visit the Winter Garden Farmers Market / Experience a Show at the Garden Theatre / Shop and Dine at Plant Street Market / 

WHAT’S NEARBY WINDWARD CAY

Animal Kingdom – 12 miles
Magic Kingdom – 11 miles
Epcot – 13 miles
Universal Orlando – 14 miles
Discovery Cove – 16 miles
SeaWorld Orlando – 15 miles
Orlando Vineland Premium Outlets – 14 miles
Orange County Convention Center – 15 miles
Epic Universe – 17 miles
Pointe Orlando – 15 miles
ICON Park – 14 miles
Disney Springs – 13 miles
The Mall at Millenia – 13 miles
Orlando International Airport – 22 miles
Downtown Orlando – 15 miles
Kennedy Space Center – 59 miles
Port Canaveral – 68 miles