Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

Welcome to Clearwater and Clearwater Beach, where sun-kissed shores meet vibrant community life! Nestled in the heart of Pinellas County, this stunning coastal paradise is renowned for its pristine beaches, crystal-clear waters, and a lifestyle that embraces both relaxation and adventure. Clearwater Beach, often celebrated as one of the top beaches in the United States, offers a picturesque backdrop for those seeking a tranquil escape or an active lifestyle filled with water sports, dining, and entertainment.

One of the most enchanting features of Clearwater is its sailboat water frontage, a dream come true for boating enthusiasts and water lovers alike. Imagine stepping out of your beautiful waterfront home and onto your sailboat, ready to explore the Gulf of Mexico or enjoy a sunset cruise along the coastline. Homes with sailboat water frontage in Clearwater Beach provide not only direct access to the water but also breathtaking views and a unique lifestyle that blends luxury with leisure.

The real estate market here offers a diverse selection of properties, from charming beach cottages to luxurious waterfront estates. Each home is a gateway to an unparalleled lifestyle, where you can indulge in fishing, paddleboarding, or simply soaking up the sun on your private dock. Clearwater Beach is more than just a destination; it’s a community filled with friendly neighbors, vibrant festivals, and a rich cultural scene.

Whether you’re looking for a vacation home or a permanent residence, Clearwater and Clearwater Beach offer an idyllic setting for your next chapter. Embrace the coastal dream and discover the magic of living by the water!

Newest Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

$650,000
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 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 condominium includes a deeded covered parking space and a private storage unit. 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
$1,692,000
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 two-year-old HVAC system with a transferable 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
$2,790,000
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
$849,000
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
$3,390,000
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
$1,995,000
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
$875,000
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. 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. 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
$1,375,000
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
$865,000
2 Beds ⋅ 2 Baths ⋅ Cabana Club Condo SubDv. ⋅ 33767 Zip Code
DIRECT GULF-FRONT LIVING ON SAND KEY with unobstructed views of the Gulf and direct access to the white-sand beach! This spacious 2-bedroom, 2-bath residence at Cabana Club offers 1,410 square feet of single-level living in a private, gated beachfront community just south of Clearwater Beach. The generous great room and primary suite both open through double doors to the private balcony, where Gulf breezes, spectacular sunsets and the sound of the waves create the perfect coastal backdrop. Thoughtfully maintained and move-in ready, the residence features new impact windows and a new air-conditioning. An assigned under-building garage space and elevator access from the garage level add everyday convenience. Cabana Club offers a true resort-style setting with direct beach access, a geothermal-heated pool and fitness center overlooking the Gulf. Located on sought-after Sand Key, enjoy a quieter stretch of coastline while remaining close to Clearwater Beach, waterfront dining, boating, shopping and entertainment. Ideal as a full-time residence or Gulf-front retreat, with furnishings also available for the opportunity to create a turnkey Florida beach escape.

1582 Gulf Boulevard Unit 1106, Clearwater
$2,950,000
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
$2,900,000
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
$1,325,000
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
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