Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

Welcome to Clearwater/Clearwater Beach, a stunning region located in Pinellas County, Florida. Known for its pristine beaches, vibrant atmosphere, and endless sunshine, Clearwater/Clearwater Beach is a paradise for those seeking a perfect blend of relaxation and excitement.

One of the most sought-after features in this area is the homes with sailboat water frontage. Imagine waking up to the gentle sound of waves and having your boat just steps away, ready to set sail into the crystal-clear waters of the Gulf of Mexico. Whether you are an avid sailor or simply appreciate the tranquility and beauty of waterfront living, Clearwater/Clearwater Beach offers a unique opportunity to indulge in waterfront luxury.

From charming beachfront cottages to modern waterfront estates, the real estate options in Clearwater/Clearwater Beach are as diverse as the stunning views that come with them. Whether you are looking for a permanent residence, a vacation home, or an investment property, you are sure to find the perfect match in this picturesque region.

With a thriving local community, a plethora of outdoor activities, and a vibrant dining and entertainment scene, Clearwater/Clearwater Beach has something for everyone. Come and experience the magic of waterfront living in this beautiful region – where every day feels like a vacation, and paradise is just outside your doorstep.

Newest Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

3 Beds ⋅ 2 Baths ⋅ Sandpipers Cove Condo SubDv. ⋅ 33767 Zip Code

Open House Friday, October 9th 11-2 PM. Experience elevated coastal living in this beautiful 3-bedroom, 2-bathroom waterfront condo that comes fully furnished, with a 3-night rental opportunity. Set on the 2nd floor, this home showcases sweeping water views from the large private balcony, creating an effortless backdrop for morning coffee, evening sunsets, and relaxed entertaining. Enjoy serene views of the water and community pool while embracing the laid-back luxury of waterfront living. Residents have full access to a heated pool, spa/hot tub, boat slip, water access, and your own cabana - offering the perfect blend of relaxation and recreation. The HOA fee includes water, sewer, trash, insurance, and community amenities at your convenience. A rare opportunity to enjoy coastal luxury living in Clearwater Beach, along with a 3 night minimum rental option giving you flexibility to make a vacation spot, rental income, or everyday use!

706 Bayway Boulevard Unit 203, Clearwater

1 Beds ⋅ 2 Baths ⋅ Island Walk Condo SubDv. ⋅ 33767 Zip Code

SPACIOUS 950-SQUARE-FOOT ONE-BEDROOM with a PRIVATE BALCONY, WATER VIEWS and VENTED IN-UNIT LAUNDRY in the waterfront community of Island Walk! While many condos on Island Estates do not offer a balcony or laundry inside the residence, this condo provides both! The living area and primary bedroom sliders open directly to the private balcony, where you can enjoy views of Mandalay Channel and the Intracoastal Waterway. With 950 square feet, this is a generously sized one-bedroom floor plan—comparable in size to some two-bedroom condos—with comfortable living, dining and entertaining spaces. UPDATED, FULLY FURNISHED and MOVE-IN READY, the condo offers an open kitchen with granite countertops and updated cabinetry, along with newer luxury vinyl flooring throughout. The updated full bathroom features a spacious full-size shower with custom glass doors and a large vanity with granite countertops. A dedicated guest half bath is ideal when entertaining or welcoming overnight guests. All major furniture will convey, allowing you to bring your suitcase and begin enjoying your Florida home immediately; select decorative and staging items do not convey. Additional features include inside storage S-34, bike storage and under-building parking space #59. HOA dues include cable and internet, water, exterior building maintenance, property management and flood insurance. Island Walk is a well-maintained waterfront building with a completed balcony and railing project featuring a Gemstone finish in 2019, a new roof in 2021, an exterior painting and building-envelope project in 2022, and an updated lobby project completed in 2024 that included fob-controlled automatic entry doors, updated mailboxes, and an updated call-box and resident directory system. More recent community improvements include new pool heaters and pumps, security cameras and an enhanced secure pool enclosure. The building has also completed its Milestone Inspection and SIRS. Community amenities include a waterfront heated pool and spa, tennis and pickleball courts, two grills and multiple outdoor dining and gathering areas. Pet-friendly with up to two pets weighing no more than 25 pounds each, and rental-friendly with a three-month minimum up to twice yearly. Marina slips may periodically become available for rent or purchase independently. Island Estates is a self-contained waterfront community offering shopping, dining, banking, a grocery store, the Clearwater Marine Aquarium and more—all just minutes from the white sugar sands of Clearwater Beach. Whether for a full-time residence, second home, 1031 exchange or coastal retreat, this condo is ready for you to start enjoying the Florida lifestyle! Come Live the Lifestyle! Come Live on the Island!

690 Island Way Unit 511, Clearwater Beach

2 Beds ⋅ 2 Baths ⋅ Island Point 1 Condo SubDv. ⋅ 33767 Zip Code

Morning sun sets the tone at 644 Island Way #406, a bright 4th-floor condo on Island Estates built for easy coastal living. This 2-bedroom, 2-bath residence spans 1,315 square feet with an open floor plan that connects the kitchen, dining, and living areas. The kitchen and both baths have been beautifully updated, and the layout flows effortlessly into a window-lined dining area with views of the surrounding island. A stylish dry bar adds extra counter space and doubles as the perfect entertaining setup, while stone countertops and recessed lighting add a polished, finished touch. Floor-to-ceiling windows in the living room create a beautiful sitting area, the perfect spot to unwind and take in the views. Both bedrooms are generously sized, and the primary suite offers a spacious walk-in closet. An in-unit washer and dryer complete the everyday convenience. This home is truly turnkey and ready to enjoy from day one, whether as a primary residence or a seasonal escape. Waterfront living here comes with real amenities: a heated community pool, a community room, a kayak launch, and one dedicated covered parking space included with the unit. Boat slips can be rented directly through the association, subject to availability. Rentals are allowed once per year, with the building capped at nine rental units total, keeping the community quiet and owner-focused. Just minutes to the world-famous Clearwater Beach — consistently ranked among Florida's best — plus the Clearwater Marine Aquarium, local shopping, fine dining, and everything else this incredible area has to offer. Fully updated and ready to enjoy, 644 Island Way #406 is a rare find on Island Estates. Schedule your private showing today and don't miss out!

644 Island Way Unit 406, Clearwater

2 Beds ⋅ 2 Baths ⋅ 51 Island Way Condo SubDv. ⋅ 33767 Zip Code

THE VIEW IS THE VALUE! Bring your contractor, your vision, and your design ideas to this desirable 11th-floor corner residence offering some truly spectacular panoramic waterfront views in Island Estates. With two separate balconies capturing sweeping views to the North, East and South, this 2-bedroom, 2-bath home offers an extraordinary opportunity to create a waterfront residence that is completely your own. Enjoy beautiful sunrises and sunsets throughout the year, sparkling water views from multiple vantage points, and an abundance of natural light that fills the residence.The spacious floor plan provides an excellent canvas for renovation. Rather than paying for someone else's finishes, bring your contractor and transform this home to reflect your own taste and lifestyle while taking full advantage of the incredible 11th-floor setting and breathtaking views.Enjoy resort-style waterfront amenities including a heated pool and spa, tiki bar, tennis, pickleball and shuffleboard courts, marina with boat slips available for approximately $60/month, kayak launch, saunas, BBQ areas, and inviting waterfront seating. Additional conveniences include optional covered parking, private storage, laundry facilities on every floor, secure keyless entry, and on-site management. The monthly fee includes cable, high-speed internet, water, sewer, trash, building insurance and reserves. Ideally located in sought-after Island Estates, just steps from Clearwater Marine Aquarium, Publix, restaurants and everyday conveniences, with easy access to Clearwater Beach, Pier 60 and the Jolley Trolley. Bring your contractor and your imagination—the interior can be transformed, but panoramic views like these simply cannot be recreated. This is your opportunity to design the waterfront home you've always wanted in one of Clearwater's most desirable island communities.

51 Island Way Unit 1100, Clearwater

2 Beds ⋅ 2 Baths ⋅ Ultimar One Condo SubDv. ⋅ 33767 Zip Code

This remodeled beautifully appointed 2-bedroom, 2-bath split-bedroom condominium offers 1,579 sq ft of thoughtfully designed living space, with abundant natural light & water views from every room. The open-concept floor plan creates an effortless flow for both everyday living and elegant entertaining. At the heart of the residence is a spectacular chef’s kitchen featureing premium appliances, custom cabinetry, and a statement island that oiffers seating. Designed for both intimate gatherings and grand entertaining with 2 wine refrigerators. Perfectly suited for entertaining guests or enjoying relaxed evenings at home. Also opens to livivng/dining area. Small office or breakfast area on one end with views of the Intracoastal. The desirable custom split-bedroom layout provides privacy and comfort for residents and guests alike. Primary bedroom has wall of windows & opens to wrap around balcony. Ensuite bath with multi shower heads & shower bench in large shower with water view. Dual sink vanityl Walki - in closet with organizers. Large guest bedroom to accomodate a king sized bed. Two private balconies extend the living experience outdoors, offering the rare opportunity to enjoy both beautiful sunrises and spectacular Gulf sunsets. Whether beginning your day with a morning coffee overlooking the water or winding down as the sky transforms at sunset, the views are truly extraordinary. Adding to the convenience and exclusivity is a private garage within the secured parking garage, a highly sought-after amenity. Set within the resort-style luxury community of Ultimar on Sand Key, this exceptional residence offers the best of coastal Florida living—elevated, and surrounded by some of the area’s most beautiful waterfront scenery. A rare opportunity to own a Gulf-front residence where every room, every balcony, and every moment is connected to the water. True Resort Style complex has 3 geo thermal heated pools w/spas, 3 tennis courts, pickle ball, basketball ct, putting green, croquet lawn, grill area, firepit area, shuffleboard, corn hole, gym, steam & sauna, billiards rm, media rm, social rm with catering kitchen and baby grand piano. Walk to great restaurants & shops or catch the Beach Trolley right out in front of the building. A short drive to Tampa & the airport plus all of the sports venues of our championship teams. Buyer to verify room dimensions. PRIVATE GARAGE #63 in parking garage. START LIVING THE FLORIDA BEACH LIFESTYLE TODAY!! Call for your persoal tour!

1520 Gulf Boulevard Unit 1107, Clearwater

4 Beds ⋅ 4 Baths ⋅ Island Estates Of Clearwater SubDv. ⋅ 33767 Zip Code

Come see and experience Florida luxury, waterfront living at 319 Midway. Located in Island Estates, one of Clearwater Beach’s most sought after communities. From the moment you enter enjoy breathtaking views of the intracoastal waters, water front views from the kitchen, dining, bedrooms, and balcony as well as from the pool and generous back yard and patio. You have direct gulf access within minutes from the private dock and boat lift in order to take advantage of boating, fishing, waterfront dining, and sunset runs from your own backyard. This four bedroom, three and a half bath residence is light, sophisticated and sleek. The open plan moves easily from formal rooms to everyday spaces, functioning effortlessly for entertaining a full house as it does for a quiet weeknight. The kitchen is outfitted with top of the line appliances, an extra-large refrigerator, and a beverage fridge. Outside, an expansive covered patio gives you shade and sun in equal measure. Upstairs, a wide balcony stretches the views even further. Both levels are hard to leave with these relaxing views, glimpses of dolphin and boats along with the lovely breeze coming in cooled by the water. 319 Midway...a home... and a lifestyle.

319 Midway Island, Clearwater

3 Beds ⋅ 4 Baths ⋅ Bayside Sub 3 SubDv. ⋅ 33767 Zip Code

90 FEET OF WATERFRONT • PRIVATE DOCK • POOL & SPA • FULLY FURNISHED • WALK TO CLEARWATER BEACH A rare opportunity to own an oversized waterfront property in the heart of Clearwater Beach. Set on an approximately 90' x 130' homesite, 136 Bayside Drive offers an exceptional combination of approximately 90 feet of waterfront, private dock, pool and spa, generous outdoor living spaces, and an unbeatable location just moments from Clearwater Beach. This single-story residence offers 3 bedrooms, 3.5 baths and approximately 2,329 SF of comfortable living space, featuring an updated kitchen and baths, terrazzo flooring, and an open layout designed to embrace the waterfront setting. Outside is where the Clearwater Beach lifestyle truly comes to life. The expansive pool terrace overlooking the water creates the perfect setting for entertaining, relaxing poolside, or enjoying sunset dinners beneath the covered patio. Beyond the pool, a private dock and approximately 90 feet of waterfront place the boating lifestyle right outside your door. The home is being offered fully furnished and completely turnkey, allowing the new owner to begin enjoying the Clearwater Beach lifestyle from day one. Furnishings are included with the sale, creating an effortless opportunity for a primary residence, second home, or investment property with established rental history. Morning coffee overlooking the water. Afternoons by the pool. Sunset dinners on the patio. Your boat at your private dock. Clearwater Beach just moments away. This is more than a waterfront home—it’s the Clearwater Beach lifestyle.

136 Bayside Drive, Clearwater Beach

3 Beds ⋅ 2 Baths ⋅ Sandpipers Cove Condo SubDv. ⋅ 33767 Zip Code

RARE CONDO INVESTMENT OPPORTUNITY at Sandpiper’s Cove! Stunning, built in 2019, TURN-KEY 3-bedroom, 2-bath luxury waterfront condo located on the south end of CLEARWATER BEACH. This beautifully furnished 5TH-FLOOR CORNER UNIT showcases spectacular, wide-open water views, enhanced by its higher-floor location and corner windows that fill the residence with natural light and capture the surrounding waterfront. Large sliders from the Great Room and Primary Suite open to an oversized balcony spanning the back of the unit - your own incredible outdoor living space to enjoy breathtaking sunsets, coastal breezes, passing boats, and watch dolphins from your own balcony. Inside, the bright and spacious open-concept design features high ceilings, wood-plank tile flooring, crown molding and remote-controlled privacy shades in both the Great Room and Primary Bedroom. The chef-inspired kitchen is beautifully appointed with GE Café stainless steel appliances, custom soft-close cabinetry and a generous peninsula overlooking the dining and living areas — perfect for entertaining. The spacious Primary Suite offers beautiful water views, direct balcony access, a sitting area, walk-in closet and a luxurious ensuite bath with dual vanities and an oversized glass-enclosed shower. Setting Sandpiper’s Cove apart is its RARE 3-DAY MINIMUM RENTAL allowance — an exceptional feature offering tremendous flexibility and strong income potential in one of Florida’s most popular beach destinations. Enjoy it as your own coastal retreat when you choose, and rent it when you’re away. Whether you're looking for a primary residence, second home, vacation retreat or income-producing property, this condo offers a unique combination of luxury, lifestyle and investment opportunity. Unit also includes a PRIVATE CABANA - perfect for beach and water-toy storage and conveniently located near the WATERSIDE HEATED POOL & SPA. Residents and guests also enjoy private community docks with direct Gulf access, a furnished pool deck, BBQ area, elevator, secure boutique 14-unit building and covered parking. Enjoy the ultimate Clearwater Beach lifestyle - boating, kayaking, paddleboarding, fishing, island hopping, or simply walking to the world-famous white sand beach, restaurants, shopping and entertainment. Call today for your private showing!

706 Bayway Boulevard Unit 501, Clearwater

2 Beds ⋅ 2 Baths ⋅ Clearwater Point 2 SubDv. ⋅ 33767 Zip Code

Panoramic Intracoastal and Clearwater skyline views, with dolphin sightings and boats heading out to open water, greet you from this beautifully renovated and furnished turnkey 2 BR / 2BA first floor, southeast-facing residence on the southern shore of Clearwater Beach. Set in the Gulf House at Clearwater Point, this split-plan condominium blends high-end finishes with an unbeatable coastal location in a well-maintained, amenity filled three-story building complex. Continuous porcelain tile is complemented by Armstrong WoodHaven ceiling planks and five upgraded ceiling fans (2024). Solid wood doors and trim throughout, louvered closet doors, and keyless entry. All windows and sliders are hurricane impact-rated (sliders replaced 2025) with custom-fitted coverings. Sliders open to a private paver patio and green space with direct beach access. The kitchen features solid wood soft-close cabinetry with pull-out drawers, quartz countertops, glass subway tile backsplash, and a pantry. Stainless steel appliances includes a newer Whirlpool refrigerator (2025). A custom laundry cabinet houses new (2026) GE front-load compact HE stackable washer with matching ventless dryer. The primary suite offers dual closets, patio access, and an en suite bath with solid wood cabinetry, quartzite countertops, and a custom porcelain tile shower. The second bathroom also features solid wood cabinetry and quartzite countertops, with tile surrounding the tub. Additional storage includes an entry closet with custom glass doors and a hall closet with built-in shelving. Other updates include HVAC (2019), water heater (2023), plumbing (2024), and electrical panel (2025). The condo includes covered reserved parking and private storage locker. Sold fully furnished, including two televisions, kitchenware, linens, and all finishings, so the buyer can move in immediately. Clearwater Point offers expansive private waterfront with beach access, three heated pools and a spa, pickleball, tennis, and shuffleboard courts, and beachfront grills, a picnic area, and a fire pit. Easy access to Tampa International and St. Pete-Clearwater airports, boating, golf, and area attractions, with walkability to dining and shopping.

865 S Gulfview Boulevard Unit 109, Clearwater Beach

2 Beds ⋅ 2 Baths ⋅ Mandalay Beach Club Condo SubDv. ⋅ 33767 Zip Code

Experience elevated coastal living from this beautifully renovated ninth-floor residence in the San Marco Tower at Mandalay Beach Club, one of Clearwater Beach’s most established and sought-after Gulf-front communities. This spacious two-bedroom, two-bath, turnkey condo features a desirable split-bedroom floor plan and exceptional south-and-west views encompassing the resort-style pool, sweeping Gulf views, Pier 60, Clearwater Harbor and the Memorial Causeway. The thoughtfully remodeled interior showcases sophisticated finishes and a cohesive contemporary design. Wood-look plank tile flows throughout the main living areas, while engineered hardwood flooring adds warmth to both bedrooms. The renovated kitchen features quartz countertops, a granite-composite sink, Reverse Osmosis system, induction cooktop, wine cooler, designer backsplash and lighting, and premium appliances, including a Fulgor Milano refrigerator. Both bathrooms have been beautifully updated. The primary suite offers a spa-inspired bath with a waterfall shower, along with a convenient coffee bar and beverage refrigerator. A stylish barn door provides added privacy between the guest bedroom and bathroom, creating a comfortable and welcoming space for guests. Floor-to-ceiling glass fills the residence with natural light and draws attention to the remarkable views. Newly installed PGT impact-resistant sliding glass doors further enhance comfort and peace of mind. Additional highlights include new washer and dryer, updated interior doors and hardware, ceiling fans and window treatments, a HVAC system with a transferable service warranty, climate-controlled storage and one deeded parking space within the private garage. Mandalay Beach Club offers an exceptional resort-style lifestyle with direct access to Clearwater Beach’s sugar-white sand, a beachfront heated pool and spa, fitness center, sauna and showers, clubhouse with kitchen, billiards room, grilling stations, on-site management and 24-hour guarded security. Located just steps from Pier 60, award-winning restaurants, shopping, water activities, nightly sunset celebrations and signature events such as the Sugar Sand Festival, this residence places the best of Clearwater Beach at your doorstep. Offered Turnkey, Unit #905 is ready to be enjoyed as a primary residence or elegant beachfront retreat, offering an exceptional opportunity to experience the views, convenience and lifestyle that make Mandalay Beach Club so highly regarded.

11 San Marco Street Unit 905, Clearwater

3 Beds ⋅ 3 Baths ⋅ Residences At Sandpearl Resort Condo SubDv. ⋅ 33767 Zip Code

From the moment you enter this coastal retreat at Sandpearl, the beauty of Clearwater Beach takes center stage. This South by Southwest and Southeast corner "D" residence offers 3 bedrooms, 2.5 baths, and a gracious open floor plan designed to enjoy both the tranquility of the coast and the energy of the city. *** Expansive Gulf views unfold from the main living areas and continue onto the west terrace, with sweeping panoramas of the Gulf of Mexico, Pier 60, Clearwater Beach and its seemingly endless coastline. Winter brings beautiful sunsets across the water, while the east-facing windows and smaller balcony offer a completely different perspective, with city views that become especially striking after dark. *** Inside, the residence feels refined yet comfortable, with a layout that provides privacy while remaining open and welcoming for year-round entertaining. Thoughtful finishes give the interiors a timeless character, including distinctive flooring, newly updated kitchen countertops, wood cabinetry, stone counters, detailed millwork, designer paint treatments, bespoke moldings, and custom tile and textures throughout. *** Life at Sandpearl extends well beyond the residence. Owners enjoy a resort-style setting with concierge services, 24-hour security, a Bermuda pool, BBQ area, billiards room, state-of-the-art fitness center, and an impressive social room. Under-building parking and a storage unit also convey. *** With the Gulf and sunsets on one side and sparkling city lights on the other, this corner residence offers a peaceful coastal retreat with the amenities and lifestyle of one of Clearwater Beach's signature resort communities.

11 Baymont Street Unit 807, Clearwater

3 Beds ⋅ 3 Baths ⋅ Pelican Port SubDv. ⋅ 33767 Zip Code

WATERFRONT TOWNHOME WITH PRIVATE BOAT DOCK & 12,000-LB LIFT ON ISLAND ESTATES! Enjoy the space, privacy and boating lifestyle of a waterfront home combined with the convenience of association-maintained living. Unlike many waterfront properties in the Clearwater Beach area, this residence is a townhome with an HOA—not a condominium—making it a unique opportunity on desirable Island Estates. This spacious multi-level corner residence offers approximately 2,200 square feet, 3 bedrooms, 3 baths plus a loft, with a private entry and added privacy from its corner location. Vaulted ceilings and an open floor plan create a light, spacious feel, complemented by an updated kitchen, renovated bathrooms and updated flooring. The oversized 2-car garage provides additional storage for bicycles, beach gear, paddleboards and all the toys that come with Florida waterfront living. Additional improvements include an updated garage door and new A/C in 2025. Step outside to your private dock and 12,000-lb boat lift and enjoy convenient access to Clearwater's surrounding waterways and the Gulf of Mexico. Whether heading out for a day of boating, fishing or simply relaxing along the waterfront, having your boat just outside your door is what the Florida lifestyle is all about. The $950 monthly HOA fee provides substantial value and includes water, gas, garbage, Spectrum cable and internet, exterior maintenance and association insurance, along with maintenance of the community swimming pool. Enjoy the comfort of waterfront homeownership while the association handles many of the exterior responsibilities—leaving more time for the things you moved to Florida to enjoy. Located on Island Estates, one of Clearwater's established waterfront communities, you'll find an exceptionally convenient island lifestyle with Publix, restaurants, shopping, banking, medical services and everyday conveniences right within the community. Walk, bike or take the Jolley Trolley to world-famous Clearwater Beach, with its sugar-white sand, waterfront restaurants, entertainment, Pier 60 and spectacular Gulf sunsets. Island Estates also provides convenient access to Clearwater Marine Aquarium, downtown Clearwater and the greater Tampa Bay area, with Tampa International and St. Pete-Clearwater International airports within easy reach. From boating and beaches to dining, biking and sunset cruises, this waterfront townhome offers the opportunity to enjoy the Clearwater Beach lifestyle every day—not just while you're on vacation.

301 Island Way Unit E, Clearwater

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