Clearwater Homes with Sailboat Water Water Frontage

Clearwater Homes with Sailboat Water Water Frontage

Welcome to Clearwater, Florida—where sun-kissed beaches meet vibrant city life! Nestled in Pinellas County, Clearwater is renowned for its stunning coastline, making it a premier destination for both residents and visitors alike. With its warm climate, friendly community, and rich cultural scene, Clearwater offers a unique blend of relaxation and excitement.

One of the most sought-after features in Clearwater real estate is homes with sailboat water frontage. Imagine waking up to the gentle sound of waves lapping against your dock, with direct access to the sparkling waters of the Gulf of Mexico. These properties not only provide breathtaking views but also the ultimate lifestyle for boating enthusiasts. Whether you're cruising along the coastline or enjoying a sunset sail, having sailboat water access right from your backyard is a dream come true.

Clearwater’s waterfront homes are designed to enhance your living experience. Many of these properties boast expansive outdoor spaces perfect for entertaining, private docks for your sailboat, and luxurious amenities that cater to a coastal lifestyle. Picture yourself hosting family gatherings or intimate dinners while watching the sun dip below the horizon.

In addition to its stunning homes, Clearwater is home to world-famous attractions like Clearwater Beach, the vibrant Pier 60, and an array of dining and shopping options. The community is known for its warm hospitality and engaging events, making it an ideal place to call home.

Explore the enchanting waterfront properties Clearwater has to offer, and discover a lifestyle filled with sunshine, serenity, and endless possibilities!

Newest Clearwater Homes with Sailboat Water Water Frontage

18675 Us Highway 19 N Unit 328, Clearwater
$117,000
1 Beds ⋅ 1 Baths ⋅ Bay Aristocrat Village Mobile Home Park Unrec SubDv. ⋅ 33764 Zip Code
Located in Bay Aristocrat Village, a 55+ resident-owned waterfront co-op community in Clearwater, this charming 1 bedroom, 1 bath mobile home offers comfortable living with numerous recent updates. Recent improvements include energy-efficient vinyl Croft windows with tilt sash (2023), two mini-split heating and cooling units (2023), and a 10' x 10' raised composite front porch (2023) that was screened in during 2024. Additional upgrades include laminate flooring in the Florida Room (2023), vapor barrier replacement (2024), carport kick-outs added to the driveway (2025), and electrical outlet and lighting added to the shed (2026). Bay Aristocrat Village is a resident-owned 55+ waterfront co-op community offering an active Florida lifestyle with a full range of amenities. Residents enjoy a clubhouse with social events and activities, heated pool and spa, shuffleboard courts, game room, library, and creative spaces. Outdoor features include a private boat launch, kayak access, fishing piers, and a protected saltwater basin connected to Tampa Bay. The community also offers scenic outdoor gathering areas designed for both relaxation and engagement. Bay Aristocrat Village is a resident-owned cooperative community with monthly fees currently $360. Buyers should review all governing documents, fees, and approval requirements with the association. Corporate ownership, LLCs, and partnerships are prohibited. No seller financing available. ESA pet policies should be confirmed with the community office. Schedule your showing and experience the Bay Aristocrat Village lifestyle.

18675 Us Highway 19 N Unit 328, Clearwater
700 N Osceola Avenue Unit 406, Clearwater
$725,000
2 Beds ⋅ 3 Baths ⋅ Bayview Condo Clearwater Unit 406 (Aka-4e) SubDv. ⋅ 33755 Zip Code
SPECTACULAR WATER VIEWS FROM EVERY ROOM! Welcome to Bayview Condominiums and this beautifully updated residence offering captivating waterfront views throughout, including a direct view of the iconic Clearwater Memorial Causeway Bridge. Enjoy an ever-changing backdrop of sparkling blue water, passing boats, gorgeous Florida skies and the excitement of the nearby BayCare Sound entertainment venue. On special occasions, enjoy fireworks lighting up the waterfront—all from the comfort of home! Recent improvements include an updated kitchen featuring granite countertops and stainless steel appliances, beautiful maple engineered wood flooring, fresh interior paint throughout and new 8-track lighting. Abundant natural light and expansive water views create a bright, inviting atmosphere from room to room. The building offers incredible ammenties for both relaxation and entertaining. The beautiful private clubhouse provides an impressive gathering space for residents and their guests, perfect for special occasions, private meetings and social events. Step directly from the clubhouse into the expansive outdoor living and pool area, complete with comfortable seating, lounge chairs and outdoor grilling areas. Just a short walk from the pool, a beautiful waterfront boardwalk leads out to the community's intimate marina. Boat slips may be rented through the association on a first-come, first-served basis, subject to availability and association requirements. While Unit #406 does not have a rented slip, owners may work directly with the association regarding current or future slip availability—an outstanding opportunity for those who want to enjoy Clearwater's incredible boating lifestyle right outside their door. The secure two-story underground parking garage is also conveniently located just a short walk from the lobby or pool and this residence includes the exceptional benefit of TWO PRIVATE PARKING SPACES, #12 AND #13, ideally located on the G1 LEVEL—not G2. This unit also offers additional private storage #26 inside a private storgae room off the elvatoron G1. Secure bicycle racks are also conveniently located within the garage. The community is RENTAL FRIENDLY with a 6-month minimum rental period . It is also PET FRIENDLY up to 2 pets. Whether enjoying the shimmering water, watching the bridge come alive after dark, heading out for a day on the boat or taking in fireworks from home, Unit #406 offers a front-row seat to the very best of Clearwater waterfront living!

700 N Osceola Avenue Unit 406, Clearwater
2153 Karan Way, Clearwater
$960,000
4 Beds ⋅ 3 Baths ⋅ Marla Grove Estates SubDv. ⋅ 33763 Zip Code
Welcome to a truly one-of-a-kind waterfront retreat in unincorporated Clearwater near Dunedin. Situated on over half an acre along the shores of Harbor Lake, this fully renovated property offers an exceptional blend of luxury living and resort-style amenities, while also offering the rare benefit of being located outside of a flood zone with no HOA restrictions. Extensively renovated in 2025 with upgrades including a new roof, new water heater, newly resurfaced pool, and new pool heater, this expansive residence features 4 bedrooms plus an enclosed sunroom/office, 3 bathrooms, and approximately 2,867 square feet. Step outside into your own private lakeside oasis featuring a heated pool, expansive entertaining areas, and direct access to Harbor Lake — a rare 40-acre spring-fed lake where boating, kayaking, and fishing are permitted. The oversized fenced lot includes abundant parking with room for boats, RVs, and recreational vehicles. The spacious primary suite and additional upstairs bedroom open to a large screened balcony overlooking the pool and lake, offering breathtaking sunset views and a true retreat-like experience. Whether used as a full-time residence, second home, luxury vacation property, or short-term rental, this property offers unmatched versatility. Furnishings available separately for purchase, making this a potential turnkey opportunity. Ideally positioned near Dunedin, Clearwater Beach, Honeymoon Island, MLB Spring Training fields, golf courses, shopping, dining, and Tampa International Airport. This exceptional property delivers the best of Florida waterfront living with privacy, flexibility, and lifestyle at its core. Rarely does a property combine this level of location, land, water access, renovation quality, and income potential in one offering.

2153 Karan Way, Clearwater
24 N Pine Circle, Belleair
$3,679,000
5 Beds ⋅ 7 Baths ⋅ Eagles Nest Point SubDv. ⋅ 33756 Zip Code
Virtually Staged. Exceptional waterfront estate in Belleair’s coveted North Pine Circle, offering unobstructed open-water views of Clearwater and beyond. The soaring 21 feet high entry foyer and wraparound balconies introduce the home’s grand scale and elegant architectural design with breathtaking bay and intercoastal waterway sunsets. Designed for both everyday living and delightful entertainment, the interior features rich woodwork, custom details, and streaming natural light throughout. Highlights include waterfront living and dining areas. The family room boasts a custom coffered ceiling, gas fireplace, wet bar, wine refrigerator and custom built-in entertainment center. The gourmet kitchen is complete with Sub-Zero and Wolf appliances, Brazilian granite countertops, dual sinks, Bosch digital dishwasher, and center island with plenty of storage, a granite breakfast bar, solid Buttercream wood cabinets, and reach in pantries with stainless steel revolving shelves. The expansive pantry/laundry room provides its own sink and LG ThinQ Front Load Washer/Dryer. Additional luxury features include a fully appointed executive’s office with hand carved cherry wood built desk, filing and storage cabinets, oak wood herringbone floors and ensuite guest bathroom. The giant game room showcases a climate-controlled hand-crafted cherry wood wine storage. Four ensuite bedrooms with private balconies, including a stunning waterfront primary suite with fireplace, built-in entertainment center, spa-style bath with granite finishes, jetted tub, dual vanities, and two giant walk-in closets. A private elevator serves all 3 floors accessible from the 4 car garage. The upper level includes a spacious multipurpose bedroom, full whirlpool bath and separate shower, generous closet space, and a private balcony with panoramic water views. Enjoy the waterfront resort-style pool and spa, lush tropical landscaping, and a private dock equipped with a pontoon lift and 54,000-pound boat lift. - Centrally located minutes from Belleair Beach, Belleair Country Club, Pelican Golf Club, Clearwater Beach, and the Morton Plant Hospital/BayCare Medical Centers

24 N Pine Circle, Belleair
429 St Andrews Drive, Belleair
$6,749,000
5 Beds ⋅ 8 Baths ⋅ Belleview Island Sub SubDv. ⋅ 33756 Zip Code
This private, world-class waterfront estate sits within the exclusive double-gated enclave of Belleview Island. Perfectly positioned on a rare double lot, the property offers breathtaking panoramic views of Clearwater Harbor and the historic Donald Ross–designed Belleair Golf and Country Club, Florida’s first golf course. A true boater’s paradise, the protected cove features a custom dock with a jet ski lift, along with 60,000 lb. and 80,000 lb. boat lifts, providing quick and direct access to Clearwater Pass and the Gulf of America. Inside, the custom-built residence showcases refined craftsmanship and elegant living spaces. A grand, custom staircase introduces the home and opens into an expansive great room designed for sophisticated entertaining, complete with a dining area, wet bar, custom built-ins, and sweeping water views. The gourmet kitchen offers a large island, custom cabinetry, granite countertops, a butler’s pantry, and a charming breakfast room overlooking both the bay and golf course. The second floor is a private retreat featuring a luxurious primary suite with its own balcony, vaulted ceilings, fireplace, and dual spa-caliber bathrooms—one with a walk-in shower and the other with a whirlpool tub—plus two walk-in closets. Three additional guest suites each include marble bathrooms and walk-in closets. Outdoor living is exceptional, with a beautifully designed pool house featuring an open wood ceiling, wine refrigerator, and grilling area, all overlooking an elegant paver pool deck. The 1,100 sq ft air-conditioned three-car garage offers high ceilings ideal for car lifts, while the landscaped grounds and custom paver driveway enhance the home’s grand presence. Engineered for long-term resilience, this elevated block construction features custom electric hurricane shutters, a whole-home Generac generator, and a new seawall (2023). The home further benefits from updated AC systems (all under warranty), a new pool and hot tub heater, tankless water heater, water softener, solar panels, LED lighting throughout, and numerous updated appliances. This exceptional residence combines pedigree, privacy, craftsmanship, and unmatched waterfront living. Secure your place in the winner's circle and experience one of Belleview Island’s finest estates.

429 St Andrews Drive, Belleair
100 Pierce Street Unit 1001, Clearwater
$385,000
2 Beds ⋅ 2 Baths ⋅ Pierce 100 Condo SubDv. ⋅ 33756 Zip Code
Now is your chance to enjoy waterfront living in downtown Clearwater. The seller is motivated. If you’ve been searching for a residence with exceptional water views, this is a rare opportunity. This remodeled and fully furnished 2-bedroom, 2-bath home at Pierce 100 sits on the desirable north side of the building, overlooking the Clearwater Marina, BayCare Sound Amphitheater, Coachman Park, and the causeway to Clearwater Beach. From your private balconies, enjoy sweeping water views, daily dolphin sightings, holiday fireworks, concerts in the park, and stunning sunsets. Inside, the bright, open living area is designed to maximize natural light and scenery. The updated master suite features a clean, contemporary look, while the modern kitchen—recently refreshed with new appliances—offers an ideal layout for cooking and entertaining. Owner will consider carrying financing. Pierce 100 enhances the waterfront lifestyle with amenities directly on the water, including a resort-style pool, fishing pier, and outdoor grill area. The Monte Carlo Room provides flexible space for private gatherings, parties, or meetings. This residence combines location, views, and modern updates in one of Clearwater’s most desirable waterfront communities. Schedule your private showing today—to experience Downtown Clearwater and make your move.

100 Pierce Street Unit 1001, Clearwater
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