Winston Estates Homes for Sale

Welcome to Winston Estates, a prestigious subdivision nestled in the heart of Clearwater Beach, Pinellas County, Florida. This exclusive community offers a luxurious and tranquil lifestyle for those seeking the perfect blend of comfort and sophistication.

Winston Estates is renowned for its meticulously designed homes that boast modern architecture, high-end finishes, and spacious layouts. From cozy single-family homes to lavish estates, there is a diverse range of properties available to suit every taste and preference.

Living in Winston Estates means enjoying the best of both worlds - a serene residential setting with convenient access to the vibrant amenities of Clearwater Beach. Residents can explore pristine beaches, upscale dining options, boutique shops, and a thriving arts and culture scene just minutes away from their doorstep.

If you are in the market for a new home, Winston Estates offers a selection of exquisite properties for sale. Whether you are looking for a primary residence, a vacation home, or an investment property, you are sure to find the perfect match in this coveted subdivision.

Don't miss the opportunity to experience luxury living at its finest in Winston Estates. Contact us today to learn more about available homes for sale and start your journey towards finding your dream home in this prestigious community.

Newest Winston Estates Homes for Sale

$1,599,000

3 Beds ⋅ 3 Baths ⋅ Winston Estates SubDv. ⋅ 33786 Zip Code

Designed by its original owner, an architect with an eye for timeless design and exceptional craftsmanship, this one-owner Belleair Beach residence is a true testament to pride of ownership. Meticulously maintained inside and out, the home welcomes you with outstanding curb appeal, a paver driveway, and beautifully landscaped, low-maintenance tropical grounds that perfectly complement its coastal setting. The lower level features an impeccably finished living space not included in the square footage, offering remarkable flexibility with a spacious living and dining area, kitchenette, generous bedroom, walk-in closet, and a full bath with a walk-in shower. With direct access to the beautifully landscaped backyard, this versatile space is ideal for guests, multigenerational living, a private home office, or extended stays. Upstairs, natural light fills the open-concept living spaces, where stunning wood floors, a cozy fireplace, and thoughtfully designed gathering areas create an inviting atmosphere. The beautifully appointed kitchen is both elegant and functional, showcasing glazed solid maple cabinetry, granite countertops, stainless-steel appliances, a professional-style vent hood, and a massive walk-in pantry. A large center island with pendant lighting and abundant seating flows effortlessly into the adjacent dining area, making entertaining a delight. A cleverly designed spiral staircase leads to a charming loft-style room, creating the perfect space for a home office, reading retreat, hobby room, or creative studio. A spacious laundry room and convenient half bath add to the home's thoughtful design. The desirable split-bedroom floor plan provides privacy for the luxurious primary suite, complete with a huge walk-in closet, sliding doors leading to a private balcony, and a spa-inspired ensuite featuring a double-sink vanity, soaking tub, and walk-in shower. The additional bedrooms are generously sized with plentiful storage and share a Jack-and-Jill bath with dual vanities and a tub/shower combination. Every detail reflects the exceptional care this home has received over the years. Located just steps from the pristine Gulf beaches of Belleair Beach and only minutes from the Belleair Causeway, shopping, dining, and countless recreational opportunities, this is a rare opportunity to own a truly special coastal home where quality, comfort, and location come together beautifully.

114 13th Street, Belleair Beach

$5,495,000

5 Beds ⋅ 6 Baths ⋅ Winston Estates SubDv. ⋅ 33786 Zip Code

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, Belleair Beach

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