Clearwater Beach Homes with Sailboat Water Water Frontage

Clearwater Beach Homes with Sailboat Water Water Frontage

Welcome to Clearwater Beach, Florida—where sun-kissed shores meet a vibrant community, creating the perfect backdrop for your dream home. Nestled in Pinellas County, Clearwater Beach is renowned for its stunning white sandy beaches, crystal-clear waters, and a lively atmosphere that attracts visitors and residents alike. Here, you can indulge in a plethora of outdoor activities, from sunbathing and swimming to boating and fishing, making it a true paradise for water enthusiasts.

One of the most sought-after features of Clearwater Beach real estate is the availability of homes with sailboat water frontage. Imagine waking up to breathtaking views of the sparkling Gulf of Mexico, with direct access to the water right from your backyard. These homes offer not only a luxurious lifestyle but also the unique opportunity to embrace the nautical lifestyle, whether you’re an avid sailor or simply enjoy the tranquility of waterfront living.

The charm of Clearwater Beach extends beyond its natural beauty. The area boasts a vibrant dining scene, trendy boutiques, and lively entertainment options, ensuring there’s never a dull moment. Plus, with a friendly community and excellent schools, it’s an ideal place for families, retirees, and everyone in between.

Whether you’re looking for a cozy beach cottage or an expansive waterfront estate, Clearwater Beach offers a diverse range of properties to suit your needs. Come explore this enchanting coastal gem, where your dream home awaits, complete with sailboat water frontage and the lifestyle you've always imagined.

Newest Clearwater Beach Homes with Sailboat Water Water Frontage

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

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

Rare Clearwater Beach waterfront opportunity in an exceptional cul-de-sac location. 290 Bayside Drive offers the ideal combination of privacy, waterfront living, and investment potential. Enjoy beautiful water views and a prime location just minutes from the Gulf beaches, boating, dining, shopping, and entertainment. This property presents an outstanding opportunity for investors, developers, or those seeking a premier coastal residence. The desirable waterfront setting and quiet cul-de-sac location create a unique opportunity to maximize the value of this sought-after Clearwater Beach property. Whether envisioned as a private waterfront retreat, vacation property, income-producing investment, or future development opportunity, this is a property with tremendous potential in one of Florida's most desirable coastal destinations. Opportunities like this are rarely available.

290 Bayside Drive, Clearwater

3 Beds ⋅ 2 Baths ⋅ Bayside Sub SubDv. ⋅ 33767 Zip Code

This Beautiful Airbnb is a dream home! “Coconut Cottage” is a rare find: a completely renovated original 1949 waterfront home in the highly sought-after neighborhood of Clearwater Beach, just a short walk from the sugar-sand beaches and crystal-clear waters of the Gulf of America. This completely updated home has 3 bedrooms, 2 baths, and offers ample natural light and waterfront views from almost every room. It features a modern kitchen with stainless steel appliances and a gas stove, three comfortable bedrooms, completely updated bathrooms, and indoor laundry, all of which provide a perfect setting for your ideal Florida life. The large backyard is a tropical oasis, complete with a resort-style saltwater pool and outdoor kitchen. It also features a dock with pontoon fittings, Trex decking & railing, low-voltage dock lighting, and a boat lift system with remote controls. The landscaping has a sprinkler system and ambient lighting. This popular Airbnb is an extraordinary investment opportunity for both generating income and/or creating your own personal vacation spot in wonderful Clearwater Beach. Financial details regarding Airbnb income and expenses are available for well-qualified buyers – contact the listing agent.

110 Devon Drive, Clearwater

2 Beds ⋅ 2 Baths ⋅ Cabana Club Condo SubDv. ⋅ 33767 Zip Code

STEP INTO THIS RESIDENCE AND IMMEDIATELY TAKE IN THE STUNNING, UNFORGETTABLE DIRECT GULF FRONT VIEWS! Located directly on the beautiful, powder soft sands of Sand Key Beach, with stunning 180-degree views of the Gulf, this 2-bedroom PLUS DEN, 2 full bath, split floor plan offers almost 1,400 sqft of spacious living area. The open kitchen offers A BEACH VIEW, custom cabinetry and a breakfast bar. Kitchen, dining and living room areas all enjoy fabulous Gulf Views. Off the kitchen is the den that could be an office or 3rd bedroom. Step out to your private 150ft covered balcony and feel the ocean breezes and breathtaking turquoise water views of the Gulf. The Gulf front master suite has a sizable walk-in closet, private access to the balcony and an ensuite bath with a double sink vanity, soaking tub and walk in shower. Bedrooms are spacious and bathrooms are generously sized. The condo has electric storm shutters (2024) on the balcony and over the patio doors. NEW AC 2019, NEW Tankless Water Heater 2019. Cabana Club offers extraordinary resort-style lifestyle with an array of amenities just steps from your door. Enjoy the Gulf-front fitness center, heated saltwater pool, basketball court, pickleball courts, and shuffleboard. Additional tennis courts are conveniently located directly across the street at Bay Park, which also features a playground and picnic areas. This unit includes assigned under-building parking space #21, along with convenient ground-level storage for beach chairs, umbrellas, and other beach gear. This exclusive Sand Key location has quick access to the Tampa airport, area dining, cultural events, shopping with convenience to St. Petersburg and other central Florida attractions. THIS IS THE EPITOME OF THE FLORIDA LIFESTYLE, CALL TODAY!

1586 Gulf Boulevard Unit 2502, Clearwater

2 Beds ⋅ 2 Baths ⋅ Dans Island On Sand Key Condo SubDv. ⋅ 33767 Zip Code

REMODELED BEACHFRONT RESIDENCE! Experience the very best of Clearwater Beach from Dan’s Island, an established Gulf-front community offering exceptional views, generous residences, and an enviable beachfront lifestyle. This beautifully updated 2-bedroom, 2-bath residence encompasses approximately 1,880 square feet and is distinguished by sweeping Gulf of Mexico views and an extraordinary wraparound balcony of approximately 900 square feet—creating an expansive extension of the living space and a front-row setting for Clearwater’s spectacular sunsets. Inside, the residence feels open, sophisticated, and remarkably spacious. One of the larger floor plans in the community, it features a gracious great room with wood flooring, an electric fireplace, and new sliding glass doors that frame the Gulf and open seamlessly to the balcony. The scale of the outdoor space is particularly impressive, with ample room for multiple seating and entertaining areas surrounded by water views. The kitchen is well appointed with custom wood cabinetry, solid-surface countertops, and stainless-steel appliances, while the desirable split-bedroom configuration provides privacy for owners and guests alike. Both the primary suite and guest suite enjoy beautiful Gulf views and direct balcony access, allowing the waterfront setting to remain an integral part of nearly every room. Updated bathrooms feature custom cabinetry and frameless glass shower enclosures for a clean, refined finish. Dan’s Island offers the amenities expected of a true beachfront community, including a 24-hour manned guardhouse, Gulf-front social room, fitness center overlooking the water, racquetball and basketball courts, and a heated pool and spa just steps from the beach. For boating enthusiasts, privately owned boat slips are located directly across the street and may occasionally become available for purchase or lease. Ideally positioned on Clearwater Beach with convenient access to restaurants, shopping, boating, and recreation, the residence is also within easy reach of both St. Pete-Clearwater International Airport and Tampa International Airport. A rare combination of substantial interior space, exceptional outdoor living, direct beach access, and panoramic Gulf views—this is Florida waterfront living at its finest.

1600 Gulf Boulevard Unit 1013, Clearwater

6 Beds ⋅ 7 Baths ⋅ Belleair Beach Unit 1 Unrec SubDv. ⋅ 33786 Zip Code

An extraordinary opportunity to own a premier beachfront estate in the highly sought-after community of Belleair Beach. Positioned directly on the pristine sands of the Gulf of Mexico, this expansive 80-foot-wide by 259-foot-long beachfront lot offers breathtaking panoramic water views, nightly sunsets, and endless potential to create a custom luxury estate tailored to your vision. The existing 9,069 total square foot residence can absolutely be enjoyed as-is, renovated, or serve as a placeholder while planning your future beach house. This estate boasts 6 bedrooms and 5 full baths and 2 half baths. Designed for entertainment, the gourmet kitchen is a chef's delight. Featuring state-of-the-art appliances, wood cabinetry, and a spacious island with cooktop and hood, all perfect for culinary creations. Entertain in the oversized formal dining room or the formal living room. You and your guests will love spending time in the large upstairs game room and full bar. Retreat to one of the two lavish primary suites, one downstairs and one upstairs. Wake up to the sound of waves gently crashing against the shore. Outside, a private oasis awaits, an oversized resort style sparkling pool and covered deck with direct access to the 80 feet of white sugar sand beachfront deeded extending beyond the seawall which leaves room beachside for chairs or even jet skis. This property offers true Gulf-front ownership—ideal for long-term investment or redevelopment. Set behind private gates, the property provides exceptional privacy and generous land footprint—an increasingly rare find along the Gulf Coast. The large lot size allows for the construction of a substantial future residence, offering ample space for a grand custom home with resort-style amenities, expansive outdoor living areas, and direct beach access. Whether your vision includes multiple levels, generous square footage, a pool and spa, or expansive terraces overlooking the Gulf, this property offers the flexibility to build at scale. Located on Belleair Beach and just minutes from Clearwater Beach and Indian Rocks Beach, you will enjoy close proximity to world-class dining, shopping, and vibrant entertainment while maintaining the tranquility and exclusivity Belleair Beach is known for. Beachfront lots of this size and caliber are increasingly scarce. 1520 Gulf Blvd represents a rare opportunity to secure an irreplaceable piece of Gulf-front land with unlimited future potential. Schedule a private tour today to explore the possibilities.

1520 Gulf Boulevard, Belleair Beach

2 Beds ⋅ 2 Baths ⋅ Cabana Club Condo SubDv. ⋅ 33767 Zip Code

Experience elevated coastal living at Cabana Club Unit 1106, offering direct gulf-front views along the white sand beaches of Sand Key. With 1,410 square feet of spacious, single-level living, this move-in-ready residence pairs an exceptional beachfront setting with the ease and convenience of resort-style amenities. The generous great room and primary suite open through double doors to the private balcony, creating a seamless connection to the outdoors, where Gulf breezes and the sound of the waves provide the ideal coastal backdrop. Inside, the residence has been thoughtfully maintained and updated with new impact windows and new air conditioner. Within a private, gated community, Cabana Club offers direct access to Sand Key’s beautiful beach, along with a geothermal-heated pool and fitness center overlooking the Gulf. An assigned under-building garage space provides added convenience, with elevator access directly from the garage level. Ideally just south of Clearwater Beach, Sand Key is known for its quieter stretch of coastline while offering easy access to nearby waterfront dining, boating, shopping and entertainment. Whether you’re looking for a full-time residence or a relaxing gulf-front retreat, this is an opportunity to enjoy the best of Florida coastal living. Furnishings are also available as an option, offering the opportunity for a turnkey coastal escape.

1582 Gulf Boulevard Unit 1106, Clearwater

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

ENJOY PRIVATE LUXURY RESIDENTIAL WATERFRONT LIVING WITHIN A SHORT WALKING DISTANCE OF CLEARWATER BEACH! Lushly landscaped with a rich circular pavered driveway, this elegant 4 bedroom, 3 bath. 4 car garage residence offers beautiful finishes, wonderful water views, and easy boating access to the intracoastal waterway and the Gulf. A richly-appointed covered entry opens to a 20ft high foyer with a dazzling circular staircase to the 1st living level. Exceptional tilework, lovely millwork and wood trim, and stunning vistas welcome you to the attractive open living room with covered balcony overlooking the waterfront. A huge open-concept contemporary kitchen boasts coastal white shaker-style cabinetry, quartz counters, high-quality appliances, gas cooking, dedicated wine/beverage chiller, an ice maker, an island bar with serving center, casual dining area, a Juliette waterfront balcony and an impressive waterfront sitting area. Adjacent to the kitchen is the laundry facility with double washer/dryer and substantial storage. Through charming double doors, you’ll discover the inviting executive office/den – spacious enough for numerous office configurations. The upper level contains a magnificent owner’s suite with sweeping views of the water, with the grand bedroom opening to a private covered waterfront balcony. A large central sitting area, with tumbled marble dual-sided fireplace, overlooks the waterfront and transitions to a luxurious owner’s bath with attractive quartz vanities, stand-along soaking tub with views of the waterfront, a private and exquisite glass-tile walk-in shower, a private rest room, and two separate walk-in closets with closet systems. A second upper-level bedroom suite enjoys front and rear waterviews, a graceful full bath, and a sizeable walk-in closet. Two additional guest bedrooms have attractive engineered hardwood floors, fine closet systems, and share a delightful covered balcony. All bedrooms and baths are splendid in their finish and appearance. From your lower-level landing, step out to the gorgeous 720sqft covered deck with covered hot tub and area plumbed for a covered outdoor gas kitchen, with additional areas for lounging and dining. Beyond the covered deck rests a generously-sized pool deck – perfect for outdoor entertaining. Your updated sea wall supports a composite dock with two jet ski lifts, step down for kayak/paddleboard launch, and moorings for a yacht or large cruiser. The home provides a 3-stop elevator and many extras! The best of boating and the beach, within easy walking distance of dining, shopping and entertainment.

136 Devon Drive, Clearwater Beach

4 Beds ⋅ 4 Baths ⋅ Dans Island On Sand Key Condo SubDv. ⋅ 33767 Zip Code

A singular Sand Key PENTHOUSE offering 3,532 square feet of impeccably updated living space sitting on top of a Gulf front building. Upon arriving at the Penthouse level, you are treated to a luminous four bedroom, four bath residence. Your new living room boasts approximately 840 square feet of living space with walls of glass flowing effortlessly onto two graceful wraparound terraces. Inside your new home you will be drawn to your unobstructed views of the Gulf and Intracoastal from everywhere you can see. Offering panoramic views from Belleair Shores to Clearwater Beach and beyond. With nightly SUNSETS mirrored by Intracoastal SUNRISES. Designed for both grand entertaining and intimate living, the chef’s kitchen showcases Cristallo Quartzite counters, renowned for their exotic and rare crystalline translucency that illuminates at night. The chef's kitchen features premium JennAir appliances, drawer refrigeration and freezer, induction cooktop, double ovens and a butler's pantry just steps away. Two secluded primary suites elevate the home’s sense of refinement. The principal suite featuring an electric fireplace, generous walk in closets and a spa inspired bath. Outside, the terraces function as private promenades above the shoreline, with an uninterrupted horizon as far as the eye can see. Completing this exceptional offering: a coveted UNDER-BUILDING parking space located just outside the lobby entrance. You get a 135 square feet of PRIVATE STORAGE space on the garage level. You also get temperature controlled storage units on the PENTHOUSE LEVEL. Dan’s Island privileges include 24 hour guard, gated security, an oceanfront heated pool, separate spa, and a poolside grilling area. A separate building housing full time management offices, fitness center with Sauna and a clubhouse. You get full Gulf views while working out in the fitness center, a full caterer's kitchen, bar area to stock for your parties, billiards, racquetball, inside basketball court and two Gulf facing balconies. Experience a rare beachfront residence—elegant, elevated, and utterly timeless. This is a MUST-SEE! Schedule your private showing today!

1660 Gulf Boulevard Unit PH1, Clearwater Beach

2 Beds ⋅ 2 Baths ⋅ Dans Island On Sand Key Condo SubDv. ⋅ 33767 Zip Code

Virtually Staged. INCREDIBLE PANORAMIC SOUTH, WEST and EAST FACING WATER VIEWS!! This rare LARGE corner residence offers 80 feet of wraparound balcony to enjoy the sunsets 365 days a year! Dan's Island is a highly sought-after community offering an exceptional opportunity to enjoy the very best of Clearwater Beach coastal living. Filled with natural light, this inviting 2-bedroom, 2-bath residence features a spacious living area and thoughtfully designed split-bedroom floor plan, providing privacy and comfort for both owners and guests. The generously sized primary suite features engineered hardwood flooring, walk-in closet, a private en-suite bath with dual vanities, rich wood cabinetry and granite countertops. The spacious guest bedroom with another walk-in closet and full guest bath provide comfortable accommodations for family and visitors. The well-appointed kitchen offers abundant cabinetry, granite countertops, stainless steel appliances and a built-in wine rack, while an interior laundry room and ample storage add everyday convenience. Additional upgrades include a HVAC system (2023), new roof (2026) and updated exterior landscaping and grounds. Dan’s Island offers an impressive array of resort-style amenities, including a beautiful clubhouse, fitness center, racquetball court, recreational facilities and inviting social spaces, as well as 24 hour security. Step outside to the expansive swimming pool and enjoy the spectacular waterfront setting just steps from the Gulf. Ideally located on Clearwater Beach, this exceptional residence puts you close to beautiful beaches, boating, dining, shopping and entertainment while offering the relaxed waterfront lifestyle Florida is famous for. Whether enjoyed as a full-time residence or coastal retreat, this rare corner unit combines spectacular views, an outstanding location and resort-style amenities in one of Clearwater Beach’s most desirable waterfront communities.

1600 Gulf Boulevard Unit 911, Clearwater Beach

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

(SELECT PHOTOS HAVE BEEN VIRTUALLY EDITED TO ILLUSTRATE THE HOME’S REMODELING POTENTIAL.) TRULY ONE-OF-A-KIND WATERFRONT OPPORTUNITY—THE ONLY LOT IN ALL OF ISLAND ESTATES WITH APPROXIMATELY 300 LINEAR FEET OF SEAWALL! Even more remarkable, this property has NEVER FLOODED. Situated on an expansive, elevated corner lot of approximately 20,691 square feet along the Intracoastal Waterway, this exceptional property offers an extraordinary amount of waterfrontage, with seawalls on two sides and direct water access from two directions. Designed to embrace the Florida waterfront lifestyle, the property features a private dock with convenient boating access and a large, beautifully maintained waterfront swimming pool. The block-masonry residence with tile roof offers approximately 3,315 square feet of heated living space, 6 bedrooms, 4 bathrooms and a 2-car garage. An impressive approximately 1,200-square-foot hurricane-glass-enclosed porch showcases sweeping water views toward North Clearwater Beach and St. Joseph Sound, creating an incredible space for relaxing and entertaining. From your own backyard, watch dolphins and abundant marine and bird life by day, then enjoy the shimmering lights of Clearwater Beach across the water in the evening. With its remarkable waterfrontage, oversized lot and spectacular setting, this property presents an exceptional opportunity to update the existing residence and create a truly extraordinary waterfront estate. Located in the highly desirable Island Estates boating community, you are just minutes from world-famous Clearwater Beach and conveniently close to Publix, banking, dining, the Clearwater Marine Aquarium and numerous local attractions. Enjoy boating from your backyard, beautiful sunrises and sunsets, and an exceptional coastal lifestyle from one of Island Estates’ most distinctive waterfront properties.

891 Island Way, Clearwater Beach

2 Beds ⋅ 2 Baths ⋅ Isle Of Sand Key 1 Condo SubDv. ⋅ 33767 Zip Code

Experience the very best of Florida's waterfront lifestyle in this beautifully renovated corner residence in the highly desirable Isle of Sand Key. This move in ready condominium has been completely reimagined from top to bottom, with no detail overlooked and no expense spared, capturing spectacular sunrises over the Intracoastal Waterway and unforgettable sunsets over the Gulf from virtually every room. The bright, open interior features new tile flooring, fresh paint, updated plumbing, and elegant crown molding throughout, all part of a complete 2022 renovation. The designer kitchen boasts new shaker style cabinetry, quartz countertops, and stainless steel appliances. The spacious family room opens through a hurricane rated door, updated in 2023, to an expansive wraparound balcony with panoramic water views. The primary suite offers a custom walk in closet and a spa inspired ensuite with custom tile work, while the guest bedroom enjoys its own stunning water views and an updated hall bath. Major systems have been recently updated and meticulously maintained, including PGT impact windows (2019), a new hot water heater (2021), a new electrical panel and encapsulated A/C ductwork (2022), and a brand new A/C unit (2024). The community offers true peace of mind with 24 hour guarded, gated entry, an on-site building manager Monday through Friday, and a full time maintenance technician five days a week. Additional highlights include covered parking and a heated waterfront pool. Boating enthusiasts will appreciate the rare opportunity to lease one of only 28 boat slips, complete with the option to purchase the 10,000 lb. boat lift from the current owner. The community boasts a new 400 ft. long boat dock (2025) with water and electricity pre-wired with 240 volt service. Best of all, the powder soft white sands of Sand Key Beach are just across the street, with restaurants and shops only minutes away. This is the perfect blend of comfort, convenience, and relaxed coastal elegance.

1621 Gulf Boulevard Unit 607, Clearwater Beach

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