Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

Welcome to Clearwater and Clearwater Beach, a sun-soaked paradise nestled in Pinellas County, Florida. Renowned for its stunning sugar-white sands and crystal-clear waters, this vibrant coastal community offers a perfect blend of relaxation and adventure. Whether you're drawn by the allure of vibrant nightlife, exquisite dining, or the simple pleasure of a sunset stroll along the beach, Clearwater Beach has something for everyone.

Among the most sought-after properties in this idyllic region are homes with sailboat water frontage. Imagine waking up each morning to the gentle sound of waves lapping at your private dock, where your sailboat awaits. These exceptional homes provide not only breathtaking views but also direct access to the Gulf of Mexico, making them a dream come true for boating enthusiasts and water lovers alike. With spacious layouts, modern amenities, and outdoor spaces perfect for entertaining, these residences offer a lifestyle that harmonizes with the beauty of nature.

Clearwater Beach is more than just a picturesque destination; it’s a community that embraces a laid-back lifestyle, with a calendar full of events, festivals, and activities. From the lively Pier 60 sunset celebrations to the tranquility of Caladesi Island State Park, there’s always something to explore.

Whether you’re looking for a primary residence, a vacation home, or a lucrative investment, Clearwater and Clearwater Beach are the perfect locales to find your dream home with sailboat water frontage. Experience the magic of coastal living and make Clearwater your home today!

Newest Clearwater/Clearwater Beach Homes with Sailboat Water Water Frontage

$439,000
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
$329,900
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
$1,165,000
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
$1,995,000
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
$2,525,000
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
$1,095,000
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
$2,790,000
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 Beach
$549,000
2 Beds ⋅ 2 Baths ⋅ Clearwater Point 3 SubDv. ⋅ 33767 Zip Code
ELEVATED 3RD-FLOOR CONDO • DIRECT WATER VIEWS FROM EVERY ROOM • PRIVATE BEACH • THREE HEATED POOLS • NEW HURRICANE-RATED WINDOWS • BEAUTIFULLY UPDATED • NEW A/C & WATER HEATER 2026 Welcome to waterfront living at Clearwater Point, ideally located on the peaceful southern end of Clearwater Beach. Set directly along the Intracoastal Waterway, this beautifully updated, light-filled residence combines spectacular water views with an exceptional resort-style lifestyle—including exclusive access to the community’s private beach and three heated swimming pools. From the moment you enter, the wide-open water views take center stage. A welcoming foyer opens to a spacious, thoughtfully designed floor plan, with the remodeled kitchen, dining area, and living spaces flowing together for easy everyday living and entertaining. The updated kitchen features light cabinetry, granite countertops, a designer tile backsplash, and stainless-steel appliances. Beautiful new luxury vinyl plank flooring runs throughout the residence, creating a fresh, cohesive coastal feel. Major improvements include new hurricane-rated windows, a new A/C system, and a new water heater—all in 2026. Both bedrooms are privately positioned on the opposite side of the residence and feature their own beautiful water views. Elevator access and laundry facilities are conveniently located just steps from the unit, and a dedicated parking space is located directly in front of the building. And then there are the VIEWS! Enjoy sweeping Intracoastal panoramas from the Florida room, living room, and primary bedroom as dolphins play, boats cruise by, and spectacular sunsets light up the sky—all from the comfort of home. Clearwater Point offers the kind of amenities that make every day feel like a vacation. Residents enjoy three heated pools, a private beach just steps from the community, a hot tub, tennis and pickleball courts, shuffleboard, waterfront grilling and dining areas, and a cozy fire pit with surrounding seating. Whether you're taking a morning walk on the sand, cooling off in one of the pools, grilling dinner by the water, or watching the sunset, this community delivers the Florida lifestyle. The community balconies are also scheduled for replacement this fall. Leave the car at home and walk to nearby restaurants, shopping, and attractions, or hop aboard the Beach Trolley to explore Clearwater Beach. Pier 60, Clearwater Marine Aquarium, cafés, restaurants, and countless recreational activities are all nearby, with convenient access to both Tampa International Airport and St. Pete-Clearwater International Airport. No dogs are permitted, and rentals require a 90-day minimum.

868 Bayway Boulevard Unit 307, Clearwater Beach
$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. 2026 Pro Forma indicates a 4.9% cap rate based on rentals through July 2026.

110 Devon Drive, 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
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