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

$350,000
2 Beds ⋅ 2 Baths ⋅ 51 Island Way Condo SubDv. ⋅ 33767 Zip Code
PRICED TO SELL! WATERFRONT ISLAND LIVING! Welcome to one of the most desirable condominium communities in Island Estates, where coastal living meets the ultimate Florida lifestyle. This updated two-bedroom, two-bathroom waterfront residence offers views of the Intracoastal Waterway, two private balconies, and an opportunity to enjoy resort-style living. Designed with comfort and style in mind, this light and bright residence features an open-concept floor plan filled with natural light from expansive hurricane-rated sliding glass doors. The beautifully updated kitchen showcases attractive stone countertops, abundant cabinetry, and a functional design that flows effortlessly into the spacious living and dining areas, making it ideal for everyday living and entertaining. Vinyl plank flooring extends throughout the main living areas, while ceramic tile complements both updated bathrooms. The spacious primary suite easily accommodates a king-size bedroom set and features a private ensuite bathroom, generous closet space, and direct access to the main balcony. The guest bedroom also enjoys its own private balcony, creating a welcoming retreat for family and friends. Enjoy peaceful Intracoastal Waterway views from both the living room and primary suite. Living at 51 Island Way is about far more than owning a condominium—it's about embracing a true waterfront lifestyle. Island Estates is one of Clearwater's premier residential island communities, surrounded by sparkling waterways and known for its boating, fishing, walkability, and relaxed coastal atmosphere. Everyday conveniences, including a Publix grocery store, pharmacy, bank, post office, restaurants, bars, coffee shops, salons, and other neighborhood services, are all located right on the island. World-famous Clearwater Beach is just a short bicycle ride, an enjoyable walk, or a quick trip on the Jolly Trolley. Spend your days boating through the Intracoastal Waterway, cruising into the Gulf, fishing, kayaking, paddle boarding, enjoying the beach, or dining at one of the area's many waterfront restaurants before enjoying a spectacular Florida sunset. Community amenities include: secure building access, heated waterfront swimming pool and spa, sauna, tiki bar, tiki huts, clubroom for social gatherings, marina with boat slips available on a first-come, first-served basis, kayak storage, dedicated kayak launching dock, fishing, tennis court, pickleball, shuffleboard courts, waterfront grounds overlooking the Intracoastal Waterway, and an assigned private storage closet. Nature lovers will appreciate frequent visits from dolphins, manatees, tropical birds, and other native Florida wildlife, while boating enthusiasts will love immediate access to the Intracoastal Waterway and convenient routes to the Gulf of America. Whether you're searching for a full-time residence, a seasonal retreat, or an exceptional waterfront investment, this beautifully updated condominium offers the perfect combination of location, lifestyle, and value. If you've been dreaming of living on an island where every day feels like a vacation, this is your opportunity to make that dream a reality. Come experience why Island Estates remains one of the Tampa Bay area's most desirable waterfront communities—and why so many residents never want to leave. Call today to schedule your private showing!

51 Island Way Unit 311, Clearwater Beach
$1,425,000
3 Beds ⋅ 3 Baths ⋅ Island Estates Of Clearwater Unit 6-A SubDv. ⋅ 33767 Zip Code
ISLAND ESTATES OF CLEARWATER BEACH, A HIGHLY SOUGHT-AFTER SELF-CONTAINED WATERFRONT COMMUNITY. 3bdrm 2.5 bath solid block home with over 2200sqft *PLUS a bonus office offers- Deep water, boat lift, location next to cul-de-sac gets you right into the intracoastal waterway quicky. Completely updated. Beautiful kitchen, renovated bathrooms, customized double closets in master bdrm, 10ft ceilings, Wolf induction stove, Subzero refrigeration, Travertine flooring, Emtek hardware, Plantation shutters throughout, Epoxy garage flooring, large dock, Boat lift has new bunkers, Roofs 2021/2017, AC 2018. MOVE IN READY SPLIT PLAN home. As you enter immediately you will see water. large living/dining area 37x19 with French doors leading out to the patio with additional French doors leading out from the master bdrm. An inviting entertaining home with spacious bedrooms. *Per seller, the home is ready for 2nd story with LVL's 16” on centers* Much to appreciate in this self-contained Waterfront Community with everything you need, including gas station, restaurants, Grocery, UPS, the Clearwater Marine Aquarium, Jolley Trolley and more. Just a short walk or bike ride to Clearwater beach- always voted Top Beach for its perfect soft white sands. Book your private showing today! Straight 30min drive to Tampa International airport.

440 Palm Island Se, Clearwater Beach
$2,300,000
3 Beds ⋅ 3 Baths ⋅ Ultimar Three Condo SubDv. ⋅ 33767 Zip Code
Step into the inviting entryway with hardwood floors, designer wallpaper & shell mirror. Exceptional Clearwater Beach completely remodeled condo features fantastic waterfront views of the Gulf, direct access to a vast Sand Key white sand beach and ideal vantage points for scenic sunrises to sunsets. The spacious open floor plan is accented by wall-to-wall, floor-to-ceiling windows and sliding glass doors that provide unobstructed views from nearly every room. Spanning 2,563 square feet, this updated three-bedroom, three-bathroom home feels even more expansive due to 10-foot high ceilings throughout that optimize the abundant natural light and natural beauty defining this location.Two covered balconies create ideal areas for al fresco dining, entertaining guests or relaxing while relishing the east to west elevated views from this eleventh floor residence. Designed for convenience and comfort, the layout includes a formal living room and family room, dining area that easily accommodates seating for friends & family, a fully outfitted gourmet kitchen with custom cabinetry, stainless steel appliances, quartz counters, countertop dining, and adjoining walk-in pantry, a separate laundry room plus butler’s pantry. Split bedroom plan provides privacy for owners as well as guests. The primary bedroom ensuite includes direct access to the Gulfside balcony, a walk-in closet and luxurious bath with marble shower, marble tub surround, custom cabinetry dual sink vanity with marble top. Desgner lighting throughout & designer funrishing included. Sun shades at windows & sliders with remote in the living room & primary bedroom. The Ultimar is a world class condo complex on Sand Key of famous Clearwater Beach. Miles of pure white sand. Lush tropical landscaped grounds are expertly maintained. 24 hr guard gated. True Resort Style complex has 3 geo thermal heated pools w/spas, 3 tennis courts, pickle ball, basketball court, 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. START LIVING THE FLORIDA BEACH LIFESTYLE TODAY!! Buyer to verify room dimensions. Sold furnished & turnkey. PRIVATE GARAGE #101 in parking garage. Call for your private tour!

1560 Gulf Boulevard Unit 1101, Clearwater Beach
$399,000
2 Beds ⋅ 2 Baths ⋅ Sea Island North 3 Condo SubDv. ⋅ 33767 Zip Code
Experience refined coastal living in this extensively renovated unit, where every detail has been thoughtfully upgraded with quality craftsmanship and timeless style. Filled with natural light, the inviting interior showcases breathtaking panoramic views of Mandalay Bay and an airy, open-concept design perfect for everyday living and entertaining. The enclosed lanai serves as an exceptional extension of the living space, providing the perfect setting to relax and take in the waterfront scenery. At the heart of the home, the beautifully updated kitchen features an impressive granite island, premium finishes, and generous prep space that will delight both casual cooks and seasoned chefs. Designer upgrades continue throughout with elegant tile flooring, recessed lighting, modern interior doors, and custom built-in cabinetry that maximizes both storage and functionality. A full-size in-unit washer and dryer add everyday convenience. Major improvements include impact-resistant, UV-protected windows, updated electrical, a newer water heater, water softener, HVAC system, wine refrigerator, and numerous additional enhancements that provide lasting value and peace of mind. Residents enjoy easy access via both the elevator and stairs, along with outstanding waterfront amenities. Spend evenings on the community dock watching spectacular sunsets, grilling with friends, launching a kayak, fishing, or taking advantage of available water, electric, and boat access. Nestled in the highly desirable Island Way community, this well-maintained building has successfully completed its required Milestone Inspection with no current assessments. Just minutes from Clearwater Beach, Publix, popular restaurants, and the vibrant entertainment of downtown Clearwater, this exceptional waterfront property offers the ideal blend of comfort, convenience, and coastal lifestyle. Buyers should verify all rules, regulations, and leasing guidelines directly with the homeowners association.

770 Island Way Unit N204, Clearwater
$265,000
1 Beds ⋅ 1 Baths ⋅ Horizon House Co-Op SubDv. ⋅ 33767 Zip Code
DIRECT VIEWS OF CLEARWATER BEACH & THE SPARKLING GULF OF AMERICA! Welcome to this move-in-ready, spacious waterfront 1-bedroom, 1-bathroom co-op located on the highly desirable Island Estates in Clearwater Beach. From the moment you enter, you are greeted by breathtaking panoramic water views of Clearwater Harbor that can be enjoyed from every room. The home features large southwest-facing windows that fill the space with natural light and showcase stunning sunsets over the water and the beauty of Clearwater Beach. The bedroom offers oversized windows with incredible waterfront views, creating a peaceful retreat where you can wake up to the beauty of the coast. The unit is offered with furnishings optional, making it easy to move right in and start enjoying the Florida lifestyle. Additional features include an upgraded FOB entry system for added security and convenience. The community offers an impressive array of amenities and services, including cable TV, internet, water, sewer, trash, electricity, insurance, exterior maintenance, grounds maintenance, repairs, pest control, pool maintenance, recreational facilities, and on-site management. Enjoy resort-style living with a community pool, fishing pier, boat dock, outdoor grilling area, recreation center, library, fitness room, indoor bike storage, free laundry facilities, private storage closets located on your floor, and game areas featuring ping pong and pool tables. Perfectly situated on Island Estates, you are just steps away from popular restaurants, shopping, grocery stores, and entertainment. The Clearwater Marine Aquarium is directly across the street, along with the iconic Island Way Grill and convenient Jolly Trolley service, providing easy access to Clearwater Beach and surrounding attractions. Experience waterfront living at its finest with spectacular views, incredible amenities, and an unbeatable location in one of Clearwater Beach’s most desirable communities.

31 Island Way Unit 505, Clearwater Beach
$325,000
2 Beds ⋅ 2 Baths ⋅ Horizon House Co-Op SubDv. ⋅ 33767 Zip Code
OUTSTANDING VALUE AND OPPORTUNITY TO OWN A PIECE OF PARADISE MINUTES TO CLEARWATER BEACH! Horizon House is one of the best maintained buildings since NO RENTALS and NO PETS allowed except for service/therapy pets. This sizable 2 bedroom, 2 bath condo with over 1,400sf is the epitome of living the Florida lifestyle. Enjoy endless sunrises by day and twinkling city lights by night from the 14th floor. WATER VIEW FROM EVERY ROOM! Upon entering, you get the wow effect from the dazzling water view of Clearwater Harbor. You can see all the way north to Dunedin! You’ll have a front row seat to the area fireworks, including the $1 million City of Clearwater display. The master suite is spacious with built-in cabinets and there’s room for a home office or sitting area. Imagine waking up every day to the stunning colorful sunrises. The master suite is appointed with a private bath and updated vanity. An added feature of this larger 2 bedroom is extra space in the master bedroom which creates a **coveted walk-in closet.** The guest bedroom has plenty of room too! Currently, it has a set of bunk beds and a full size bed. Newer flooring throughout, no carpet! The heated waterfront pool and fishing dock with cleaning station are located directly on the Intracoastal and boat slips are available as first come first serve. Don’t want to wait for a boat slip? Buy your own dock from Island Estates Marina. Bike and kayak storage also available. You'll love living on Island Estates, with fine dining, post office, gas station, new Publix and playground. PLUS you're less than a mile to the sugar white sands of Clearwater Beach. Building is a co-op, HOA fee INCLUDES ELECTRIC, water, trash, basic cable, HVAC, water heater, community generator, use of FREE washer/dryer and security guard. Call today, this is THE PERFECT Florida getaway!

31 Island Way Unit 1404, Clearwater
$750,000
2 Beds ⋅ 2 Baths ⋅ Isle Of Sand Key 1 Condo SubDv. ⋅ 33767 Zip Code
WATER VIEW FROM EVERY ROOM!!! OUTSTANDING VALUE FOR THIS SPACIOUS CONDO WITH WRAP AROUND CORNER BALCONY. This 2 bedroom, 2 bath, 1,500sqft condo with 1 car carport brings to you the best of boating and the beach. This cozy NE corner residence in the quiet GATED waterfront community of Isle of Sand Key is tucked away from Gulf Blvd, but is only a short 3-minute walk to the powder soft sands of Sand Key Beach. The first come, first serve boat slips allow for fast, easy access to the Intracoastal waterway and the Gulf. The kitchen with breakfast bar is ready for your culinary creations, featuring a GORGEOUS INTRACOASTAL WATER VIEW. Newer washer/dryer installed. There’s plenty of space for an 8-10 dining set for large families. The sizable 300sf master suite enjoys both Gulf and Intracoastal views and you can even hear the sound of the ocean! The walk-in closet is enormous! Step out onto the balcony and your cares instantly melt away. You have panoramic water views in every direction. The Isle of Sand Key gated community offers relaxing resort amenities such as a solar-heated community pool, BBQ area, covered sitting area, docks for fishing, boat slips (first come), sauna and fitness center! Only minutes away from award-winning Clearwater Beach. With its uncommon size & sleeping capabilities, this residence is ideal for entertaining with extended stays for families & guests. A great location & terrific value! UPGRADES: NEW AC 2019, NEW Water heater 2025, NEW Impact Windows 2018. **BE SURE TO CHECK OUT THE 3D VIRTUAL TOUR LINK.**

1621 Gulf Boulevard Unit 1408, Clearwater Beach
$369,000
2 Beds ⋅ 2 Baths ⋅ Horizon House Co-Op SubDv. ⋅ 33767 Zip Code
Welcome to this beautifully updated 5th-floor, 2-bedroom, 2-bath residence at the highly sought-after 31 Island Way Co-op, where spectacular water views, spacious interiors, and resort-style amenities create the ultimate Florida waterfront lifestyle. The elevated 5th-floor location offers breathtaking vistas and an abundance of natural light throughout. Enjoy truly maintenance-free living with an extensive monthly fee that includes **electricity, water, sewer, cable television, basic Wi-Fi, building insurance, professional property management, and lobby attendants.** This well-managed community allows you to focus on enjoying your surroundings rather than worrying about everyday expenses and upkeep. Residents have access to an impressive array of amenities designed to enhance every aspect of daily living. Relax beside the geothermal-heated waterfront pool, stay active in the **fully renovated fitness center, gather with friends in the stylish lobby seating areas, or host special events in the spacious clubhouse and social rooms. Additional conveniences include Free laundry facilities, private storage closets on each floor, indoor bicycle storage, a library, billiards, ping pong, and numerous recreational gathering spaces. The building has undergone significant updates, including a state-of-the-art secured entry system, modernized elevators, upgraded HVAC systems, renovated common areas, updated lobby flooring, and an enhanced fitness facility, providing comfort, security, and long-term value. Outdoor enthusiasts will appreciate the fishing pier, boat dock, outdoor grilling areas, and boat slips available on a first-come, first-served basis for a nominal monthly fee. The association maintains full reserves and handles exterior maintenance and common areas, offering exceptional peace of mind. Ideally located on Island Way, you'll be just minutes from everything Clearwater has to offer. Take a short walk, bike ride, or trolley trip to local shops, restaurants, grocery stores, the Clearwater Marine Aquarium, and the sugar-sand beaches of world-famous Clearwater Beach. The convenient Jolly Trolley stop directly across the street makes exploring the area effortless. Don't miss this opportunity to own a stunning 5th-floor waterfront residence in one of Clearwater's most desirable communities where every day feels like a vacation. This Property does not allow pets or rentals.

31 Island Way Unit 508, Clearwater Beach
$499,900
2 Beds ⋅ 2 Baths ⋅ Island Point 1 Condo SubDv. ⋅ 33767 Zip Code
Experience the best of Island Estates living in this pristine, UPDATED, FULLY FURNISHED, move-in ready 2-bedroom, 2-bath condominium. Showcasing chic décor, premium finishes, and an open floor plan, this beautifully updated residence features luxury vinyl flooring throughout. The gourmet kitchen offers stainless steel appliances, solid surface countertops, a breakfast bar, and a stylish dry bar in the dining area that's perfect for entertaining. Located on the fourth floor, this bright and inviting home enjoys beautiful morning sun and partial Intracoastal water views. The spacious floor plan offers generously sized bedrooms, with the guest bedroom large enough to accommodate two queen-size beds. The primary suite features two closets, including a walk-in closet, along with abundant storage throughout the home, including storage solutions throughout the property. In unit washer and dryer are also included for added convenience. Major updates include the HVAC system and water heater (2020). This secure building offers key fob entry, security cameras, an assigned covered parking space #20. The HOA fee includes cable, water, and high-speed internet. Perfectly located on Island Estates, you'll be just minutes from Clearwater Beach and within walking distance of Publix, banks, restaurants including Island Way Grill, shops, the Clearwater Marine Aquarium, and a variety of waterfront activities. Enjoy scenic waterfront walks, bike rides, or simply relax and embrace the coastal lifestyle this highly desirable community has to offer. Boating enthusiasts will appreciate the private community dock on the Channel, with boat slips available for rent through management (subject to availability), as well as a kayak rack. Spend your evenings relaxing by the waterfront pool or private dock while watching spectacular sunsets, dolphins, and boats cruise by. Don't miss this exceptional opportunity to own a beautifully updated, fully furnished waterfront condominium in one of Clearwater's most desirable communities. Furnishings are included, making this the perfect primary residence, vacation home, or investment opportunity.

644 Island Way Unit 405, Clearwater
$825,000
3 Beds ⋅ 3 Baths ⋅ Sunwatch On Island Estates SubDv. ⋅ 33767 Zip Code
Virtually Staged. Experience breathtaking water views and resort-style living from this stunning northeast corner residence in sought-after Sunwatch Condominiums on Island Estates. Perched on the 8th floor, this move-in-ready condo showcases panoramic vistas of the Intracoastal Waterway, St. Joseph Sound, Downtown Clearwater, and even Dunedin in the distance. Designed to maximize natural light and waterfront scenery, this spacious split-bedroom floor plan offers privacy for both owners and guests. The open-concept living area flows seamlessly to an expansive balcony where you can enjoy passing yachts, dolphins, personal watercraft, and seabird activity. A private balcony off the primary suite provides the perfect retreat for enjoying spectacular seasonal sunsets, while the guest bedrooms enjoy access to their own wraparound balcony. Recent updates include luxury vinyl tile flooring throughout, creating a fresh, modern feel. A rare and highly desirable feature unique to this unit is the climate-controlled storage room conveniently located inside the residence near the guest bath, rather than on an exterior balcony as found in most Sunwatch units. For added convenience and security, this home includes under-building assigned parking space #83. Sunwatch offers an exceptional waterfront lifestyle on 3.8 acres and over 300 ft of waterfront, located within the vibrant, self-contained Waterfront Community of Island Estates. The amenities rival a private resort, including two swimming pools, spa, fitness center, two tennis courts, pickleball courts, billiards and meeting room, party room, two covered waterfront pavilions, grilling areas, beautifully landscaped grounds, and marina slips when available, and two exclusive guest suites for owners. Milestone and SIRS studies are done and fully funded. A full-time property manager and maintenance supervisor provide additional peace of mind. Located just minutes from Clearwater Beach and within walking distance of dining, shopping, services, and the Clearwater Marine Aquarium, this pet-friendly community allows one-year minimum rentals, making it an excellent full-time residence, seasonal retreat, or 1031 exchange opportunity. Come discover why Island Estates is one of Clearwater's most desirable waterfront communities. Your Florida lifestyle awaits.

670 Island Way Unit 800, Clearwater Beach
$2,450,000
3 Beds ⋅ 3 Baths ⋅ Mandalay Beach Club Condo SubDv. ⋅ 33767 Zip Code
Welcome to Unit 901 at Mandalay Beach Club, an exceptional 9th-floor beachfront residence in one of Clearwater Beach’s most admired luxury communities. Renowned for its sugar sand beaches, crystal-clear Gulf waters, and vibrant coastal lifestyle, Clearwater Beach is consistently recognized as one of the premier beach destinations in the country. This beautifully updated 3-bedroom, 2.5-bath condominium was completely remodeled in 2025, including all three bathrooms, and features refined finishes and modern design throughout. The desirable split-bedroom floor plan offers privacy and comfort, making it ideal for full-time living, a seasonal retreat, or hosting family and guests. Enjoy stunning panoramic Gulf and beach views from your private balcony, the perfect place to relax and take in spectacular sunsets. Residents of Mandalay Beach Club enjoy an unmatched resort-style lifestyle with 24-hour guarded security, a beautiful beachfront pool and spa, a state-of-the-art fitness center with sauna and showers, and an elegant clubhouse. A/C unit is 1 years old with a 5 year warranty which is transferable. Experience luxury coastal living at its finest in one of Clearwater Beach’s most sought-after addresses.

10 Papaya Street Unit 901, Clearwater Beach
$799,000
3 Beds ⋅ 3 Baths ⋅ Skiff Harbour Twnhs Condo SubDv. ⋅ 33767 Zip Code
0WNER FINANCING AVAILABLE.!! Meticulously maintained and beautifully updated home. This exceptional waterfront townhome is light, bright, and filled with natural sunlight thanks to multiple skylights and abundant windows throughout. Showcasing designer finishes, quality craftsmanship, and thoughtful upgrades throughout, this home offers the perfect blend of style, comfort, and functionality while showing like a model. Priced to sell in todays market, this 3-bedroom, 3 full bath residence offers water views and outdoor living space from all three levels, allowing you to enjoy the coastal setting from nearly every room. Enjoy access to a private NEW10K boat lift and a waterfront swimming pool shared by only eight other townhomes, creating an exclusive and relaxed waterfront lifestyle. Recent improvements include all new hurricane-impact windows and doors, new flooring, fresh interior paint, updated appliances, custom blinds, closet organizers, a water softener system, electric vehicle charging hookup, and numerous additional upgrades. Every detail has been carefully considered, making this a truly move-in-ready, turnkey property. Contact the listing agent for a complete list of updates and features.

218 Skiff Point, Clearwater Beach
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