Winston Estates Real Estate

Welcome to Winston Estates, a hidden gem nestled in the heart of Clearwater Beach, Florida. This charming subdivision offers a perfect blend of coastal living and suburban tranquility, making it an ideal retreat for families, retirees, and anyone seeking a slice of paradise.

Winston Estates boasts a collection of beautifully designed homes, each reflecting the unique charm and character of the Sunshine State. With lush landscaping and well-maintained streets, the neighborhood exudes a welcoming atmosphere that invites you to explore and connect with your neighbors. Residents here enjoy spacious yards, perfect for outdoor gatherings, gardening, or simply soaking up the Florida sun.

One of the standout features of Winston Estates is its prime location. Just a short drive away, you'll find the pristine beaches of Clearwater, known for their soft white sands and crystal-clear waters. Spend your weekends basking in the sun, enjoying water sports, or indulging in fresh seafood at local eateries. The vibrant beach lifestyle is complemented by a variety of shopping and dining options, ensuring that everything you need is just around the corner.

Families will appreciate the nearby schools and parks, providing ample opportunities for recreation and education. With a strong sense of community and a laid-back atmosphere, Winston Estates is the perfect place to call home.

If you're looking for a peaceful retreat that offers both relaxation and adventure, Winston Estates in Clearwater Beach is the ideal choice. Come experience the enchanting lifestyle that awaits you in this delightful subdivision!

Newest Listings in Winston Estates

$695,000

2 Beds ⋅ 2 Baths ⋅ Winston Estates SubDv. ⋅ 33786 Zip Code ⋅ TB8540721 MLS ⋅ Active Status

Welcome to your beautifully updated beach retreat in desirable Belleair Beach! Meticulously maintained and truly move-in ready, this 2-bedroom, 2-bath split-plan home with a 1-car garage is ideally located just a 2-minute walk from the beach. The current owner has thoughtfully upgraded the home throughout, creating a stylish and comfortable space designed for easy coastal living. Recent improvements include fresh interior and exterior paint, remodeled bathrooms, a beautifully renovated kitchen, new tile flooring, a new water heater, washer and dryer, new interior doors and hardware, new A/C ductwork, and a renovated garage. Impact-rated windows and multi-slide patio doors were installed in 2020. The updated kitchen features quartz countertops and backsplash, new appliances, and a wonderful view of the oversized backyard through the expansive glass sliders. The spacious primary suite offers a wall of closets and a private bath with a walk-in shower. The versatile guest bedroom or office provides generous closet space and is complemented by a beautifully renovated guest bath with a tub/shower combination. Step outside to your private backyard oasis, complete with tropical landscaping and a large shaded entertaining area—perfect for hosting family and friends. With plenty of room to add a pool, the backyard offers exceptional potential for creating your own outdoor paradise. A newly paved driveway and thoughtfully landscaped grounds enhance the home's curb appeal. Just steps from the beach, this home offers the opportunity to enjoy the relaxed Belleair Beach lifestyle without sacrificing convenience. Residents enjoy access to a boat ramp, fishing piers, tennis courts, a park, and a playground. With restrictions on public parking and commercial businesses, Belleair Beach offers a peaceful, residential atmosphere and a more private beach experience. Whether you're looking for a full-time residence, vacation getaway, or coastal retreat, this home is ready for you to move in, relax, and enjoy everything beach living has to offer. Start your mornings with coffee on the beach and end your evenings watching spectacular sunsets!

114 12th Street, Clearwater Beach

$1,499,000

3 Beds ⋅ 3 Baths ⋅ Winston Estates SubDv. ⋅ 33786 Zip Code ⋅ TB8534318 MLS ⋅ Active Status

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, Clearwater Beach

$5,495,000

5 Beds ⋅ 6 Baths ⋅ Winston Estates SubDv. ⋅ 33786 Zip Code ⋅ TB8502133 MLS ⋅ Active Status

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

$449,000

Winston Estates SubDv. ⋅ 33786 Zip Code ⋅ TB8459702 MLS ⋅ Active Status

Virtually Staged. BUILD YOUR CUSTOME HOME- SEE PHOTOS FOR SOME OPTIONS! Buildable Vacant Lot close to beach access in Belleair Beach, FL – Potential Gulf & Intracoastal Views Rare buildable residential lot in the exclusive Town of Belleair Beach, Florida. Located on a quiet barrier island just steps from the Gulf of Mexico, this vacant lot presents an outstanding opportunity to design and build a custom coastal home with potential Gulf of Mexico and Intracoastal Waterway views from an elevated structure (buyer to verify). Surrounded by established luxury residences, this property is ideal for builders, investors, or buyers seeking a primary residence or second home in one of Pinellas County’s most desirable beach communities. Property Highlights Buildable residential lot in Belleair Beach, FL Barrier island location near the Gulf of Mexico Potential Gulf & Intracoastal Waterway views from an elevated home Deeded beach access nearby Quiet, residential-only town (no hotels or commercial development) Directly across from the Belleair Beach Community Center Minutes to Clearwater Beach, Belleair Bluffs, Indian Rocks Beach, and Sand Key Close to boating, fishing, dining, shopping, and golf Location & Lifestyle Belleair Beach is known for its private feel, limited public access, and residential character. With no commercial zoning and strict development standards, the town offers a peaceful coastal environment that preserves long-term value. Across the street, the Belleair Beach Community Center provides tennis and basketball courts, a playground, shaded picnic areas, Intracoastal shoreline access, and community events—an exceptional amenity for a vacant land offering. Boating & Water Access Just over the Belleair Beach Causeway, a public marina and boat ramp offer convenient access to the Intracoastal Waterway and the Gulf of Mexico—perfect for boating, fishing, and waterfront recreation. Investment & Build Potential Vacant land in Belleair Beach is extremely limited. Building an elevated coastal home may allow for both Gulf and Intracoastal views, enhancing lifestyle appeal and resale value (subject to design, elevation, and local approvals). Whether building a full-time residence, seasonal retreat, or luxury investment property, this lot offers exceptional upside in a tightly held coastal market. Schedule a Site Visit Walk the lot, review building options, and explore the potential this property offers. Contact us today for additional information.

Causeway Boulevard, Clearwater Beach

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