Winston Estates Homes with Pool

Winston Estates Homes with Pool

Welcome to Winston Estates, a hidden gem nestled in the heart of Clearwater Beach, Florida. This charming subdivision is a delightful blend of coastal living and modern convenience, making it an ideal place for families, retirees, and anyone looking to embrace the Florida lifestyle.

Winston Estates boasts a collection of beautifully designed homes, many of which feature private pools that provide the perfect oasis for relaxation and entertainment. Imagine stepping out of your back door into your very own backyard paradise, where you can soak up the sun, host summer barbecues, or unwind with a refreshing swim after a long day. The homes are thoughtfully crafted with spacious layouts, modern finishes, and lush landscaping that enhances the overall appeal of the community.

Located just minutes from the pristine sandy shores of Clearwater Beach, residents of Winston Estates enjoy easy access to a vibrant beach lifestyle. Take a leisurely stroll along the shoreline, indulge in water sports, or savor fresh seafood at nearby restaurants. The area is also home to an array of shopping, dining, and recreational opportunities, ensuring that you never run out of things to do.

Winston Estates is not just a place to live; it’s a community where neighbors become friends and memories are made. With its prime location, beautiful homes with pools, and a welcoming atmosphere, Winston Estates offers the perfect backdrop for your next chapter in life. Come discover the charm and tranquility of this lovely subdivision today!

Newest Winston Estates Homes with Pool

$1,025,000
4 Beds ⋅ 3 Baths ⋅ A12062264 MLS
"Live where every day feels like a vacation". Just a 3 min stroll to the sugar- white sands of Belleair Beach where you can enjoy breathtaking Gulf sunsets every evening! This beautifully upgraded 4-bedrooms/ 3-bathrooms home with almost 3,000 sqft blends timeless coastal elegance with modern luxury. Featuring a stunning designer kitchen, open living areas, recently resurfaced pool with new heat pump, screened & outdoor summer kitchen. All the Bedrooms are upstairs for added privacy, beautifully renovated bathrooms, newer Roof (under warranty) freshly painted inside and out, LED lights and ceramic/ white porcelain floors throughout the entire home. The Impact windows & doors and New appliances are some of the highlights of this property. The elevated construction offers valuable peace of mind with NO FLOODING during recent storms. A rare opportunity to own a move-in-ready Beach home in one of Florida’s most desirable coastal private communities. Sellers are very motivated, schedule your private showing today and fall in love with this beauty! First OPEN HOUSE on 08/09/26 from 12- 3:00 pm. Come visit us!

107 Causeway Boulevard, Belleair Beach
$5,495,000
5 Beds ⋅ 6 Baths ⋅ TB8502133 MLS
Set along the pristine deepwater shoreline of 1203 Bay Dr, Belleair Beach, FL 33786, where elevated coastal living, breathtaking water views, and impeccable design come together across three expansive levels. Perfectly positioned to capture wide-open water vistas, this home is filled with natural light, enhanced by large windows and an open-concept layout that seamlessly connects the main living spaces. The living room opens to a private balcony, as does the primary suite above—creating multiple vantage points to take in the serene waterfront setting. The three car garage opens to a lower foyer with stairs or your own elevator, a bedroom and full bathroom and a large flex space ideal for a gym, game room, or additional lounge—perfect for guests or easy access from the pool and outdoor areas. The second level serves as the heart of the home, designed for both everyday comfort and upscale entertaining. The open floor plan flows effortlessly between the living room, dining area, and chef’s kitchen. A stylish dry bar in the living room, complete with a wine fridge and beverage refrigerator, adds a sophisticated touch. The kitchen is a true showpiece, featuring dual islands (one with a sink) and premium appliances including a Wolf gas range with pot filler, Wolf oven and microwave, Sub-Zero refrigerator, and Bosch dishwasher. A laundry room with sink is conveniently located just off the kitchen. This level also includes three bedrooms and two and a half bathrooms, along with elegant finishes such as coffered ceilings and extensive custom built-ins. Occupying the entire third level, the primary suite is a private sanctuary designed for ultimate luxury. The bedroom and spa-inspired bathroom each feature a fireplace, while the bath offers dual toilets with bidet, a clawfoot soaking tub, and a walk-in shower. The custom his-and-hers closet is truly exceptional—highlighted by a boutique-style dressing space of remarkable scale and design. Throughout the home, thoughtful upgrades include a central audio system, built-in vacuum, and a full ADT security and camera system. Three zoned air conditioning systems, including a 5-ton unit for the main living area, ensure year-round comfort. Outdoor living is equally impressive, with two fully equipped outdoor kitchens—one featuring an ice maker, refrigerator, and grill, and the other with a Wolf stove and hood—ideal for hosting. The backyard is a private resort, complete with a pool and spa with waterfall, a built-in firepit, outdoor shower, putting green, and maintenance-free landscaping. For boating enthusiasts, the property offers true deepwater access, accommodating larger vessels with ease. The oversized double dock is equipped with lighting and water, along with a 30,000 lb boat lift and a 15,000 lb jet ski lift—delivering a premier waterfront lifestyle in Belleair Beach, Florida. This is a rare opportunity to own a meticulously designed waterfront residence where every detail—inside and out—has been curated for luxury, comfort, and unforgettable coastal living.

1203 Bay Drive, Clearwater Beach
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