Holmes Beach Homes with Sailboat Water Water Frontage

Holmes Beach Homes with Sailboat Water Water Frontage

Welcome to Holmes Beach, a hidden gem nestled in the heart of Florida's Manatee County. This enchanting coastal community offers an idyllic escape for those seeking a serene lifestyle by the water. Renowned for its stunning beaches and vibrant atmosphere, Holmes Beach is the perfect blend of relaxation and adventure.

One of the most sought-after features of homes in this charming subdivision is their sailboat water frontage. Imagine waking up each morning to the gentle sound of waves lapping against your dock, with direct access to the sparkling waters of the Gulf of Mexico. Whether you're an avid sailor or simply enjoy the tranquility of waterfront living, these properties provide the ultimate coastal experience.

Holmes Beach boasts a variety of beautiful homes, each uniquely designed to capture the essence of island life. From spacious single-family residences to charming beach cottages, there is something for everyone. Many of these homes feature expansive outdoor spaces, perfect for entertaining or simply soaking up the sun. With lush landscaping and breathtaking views, you’ll find yourself in a paradise that feels like a permanent vacation.

Beyond the allure of waterfront living, Holmes Beach is also home to a vibrant community with an array of local shops, dining options, and recreational activities. Explore the nearby nature trails, indulge in fresh seafood at local eateries, or spend your days lounging on the pristine sandy shores.

In Holmes Beach, every day feels like a getaway. Discover the magic of sailboat water frontage and make your dream of coastal living a reality in this charming Florida enclave.

Newest Holmes Beach Homes with Sailboat Water Water Frontage

$5,995,000
5 Beds ⋅ 5 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
Tucked along an extraordinary 225 feet of waterfront, this custom coastal retreat distills the very essence of island living—breathtaking water views, exceptional privacy, and thoughtfully designed spaces that move effortlessly between serene relaxation and spirited entertaining. A palm-lined driveway sets the tone, where timeless architecture and lush tropical landscaping leave an unforgettable first impression. This residence carries rare local significance as the very first custom home built by Ross Built Construction, masterfully designed by renowned architect Gene Aubry. It stands as a lasting testament to their craftsmanship and creativity—and their contribution to luxury coastal living on Anna Maria Island. Their influence resonates throughout: a thoughtful floor plan, an exceptional command of natural light, and a seamless connection between indoor and outdoor living. Inside, travertine tile and hand-scraped maple flooring flow through a light-filled interior crowned by soaring vaulted ceilings in the living and kitchen areas. The chef's kitchen is as functional as it is beautiful, appointed with stone countertops, copper sinks, a gas range with pot filler, premium appliances, and a generous center island that anchors the home's main gathering spaces. Five spacious ensuite bedrooms, a dedicated den/office, and an upstairs bonus room offer effortless flexibility for family and guests. The primary suite is a private sanctuary unto itself, featuring a remodeled spa-inspired bath with custom built-in shelving and elegant finishes throughout. Designed to embrace the waterfront lifestyle, expansive glass doors open to an impressive 1,400-square-foot veranda overlooking the sparkling saltwater pool and tranquil waterways beyond. Boaters will appreciate the private dock and 10,000-lb boat lift for effortless access to open water, while an oversized three-car garage, elevator, impact-rated windows and doors, Sonos sound system, mosquito misting system, rainwater cistern, and exterior irrigation system deliver convenience and lasting peace of mind. Perfectly positioned in the heart of Holmes Beach, the property is just moments from the sugar-sand beaches of the Gulf, beloved local restaurants, boutiques, and island shops—a rare pairing of private waterfront sanctuary and walkable island convenience. Whether savoring spectacular sunsets from the veranda, entertaining poolside, strolling to nearby dining, or setting out for a day on the water, this remarkable residence offers something exceedingly rare: not only an extraordinary waterfront home, but a meaningful piece of island history, where inspired architecture, enduring craftsmanship, and an unrivaled setting come together in perfect harmony.

526 56th Street, Holmes Beach
$985,000
2 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
Discover the best of island living in beautiful Holmes Beach! Nestled on a quiet street in a peaceful neighborhood, you’ll love the combination of boating access and close proximity to the beach this home has to offer. Elevated with impact windows, this 2-bedroom, 2-bathroom home is turnkey furnished and includes a deeded, unimproved boat slip at the end of 85th Street, perfect for boating enthusiasts and those seeking the ultimate coastal lifestyle. New roof installed in August 2025. The downstairs area has been professionally remediated and renovated, while the upstairs living area remained untouched by hurricanes in 2024. Situated on an expansive 9,000sqft lot, there is ample space to add a pool and create your own private oasis. Whether you’re seeking a primary residence or a tropical getaway, this property is ideal for enjoying Anna Maria Island living. Book your showing today!

221 85th Street, Holmes Beach
$4,295,000
4 Beds ⋅ 3 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
One or more photo(s) has been virtually staged. Spectacular Waterfront Key West-Style Home on Bimini Bay!! This beautifully maintained 4 bedroom, 3 bathroom single-family home, offering 2,775 sq ft of living space on a spacious 9,400 sq ft lot. Meticulously crafted with thoughtful architecture, interiors and landscaping by legendary award-winning architect, Emily Anne Smith. As you step in, you’ll notice the double height ceilings, unique, blue glass chandelier in the entry that leads into the spacious open floor plan. Large slider impact doors that create natural light and provide stunning views of Bimini bay. The living room is warmed by a modern linear fireplace complemented by a wall of custom illuminated floating shelves and built-in cabinetry with an exquisite backlit blue agate Antolini countertop. A chef's dream, the kitchen is equipped with Monogram Professional Series appliances, quartz countertops and a thoughtful layout. Abutting the kitchen is the large laundry room leading to an oversized two car garage. A first floor primary suite has privacy and features an oversized en suite bathroom with double marble vanity. In addition, the first floor has a full bathroom with a frameless glass shower, custom blue glass waterfall sink and two generously sized bedrooms. The entire second level luxurious main suite features breathtaking water views, cathedral ceilings, dual custom walk-in closets, a large spa-like bathroom with a freestanding jetted tub surrounded by backlit quarzite counters, Bisazza tile, modern crystal chandelier, dual Carrara marble vanities, and spacious modern reclaimed wood porcelain tile walk-in shower. An expansive rooftop terrace and gazebo, not to be missed, offers a stunning 360-degree view of Anna Maria Island. Step outside to entertain on the expansive pool deck with a large pool, or retreat to the private upper deck for quiet sunsets and bay breezes. Resort style outdoor area includes an outdoor kitchen and bar, outdoor shower, covered fishing station, dual lift and dock area for jet skis and ample space to accommodate a large yacht, fishing or sport boat, making indoor/outdoor living and entertaining flawless. Brand new Interior and exterior paint throughout! Enjoy deep-water frontage with no bridges to the Gulf of Mexico and your own 9,000 lb boat lift — perfect for boating enthusiasts who want effortless Gulf access and quick runs to the open water. The home is just a short golf cart ride gorgeous sand beaches, making it ideal for beach lovers, families, or those seeking the ultimate Florida island lifestyle.

8321 Marina Drive, Holmes Beach
$3,300,000
4 Beds ⋅ 6 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
Nestled along a serene canal and embraced by a curtain of mature tropical palms, this custom-remodeled residence unfolds as a private coastal estate, an intimate sanctuary where luxury, tranquility, and effortless island living exist in perfect harmony. Masterfully re-imagined by Eason Builder Group, the home was completely gutted and rebuilt just four years ago, and last year the entire first level was once again fully renovated, resulting in a residence that feels both newly crafted and timelessly refined. From the moment you arrive, a sense of seclusion and calm sets in. As you walk up to the home, an old-growth Gumbo Limbo greets you. Sunlight filters through new hurricane-impact windows, illuminating interiors designed to feel open yet intimate, grand yet soothing. The main living space becomes a natural gathering place, anchored by a custom-built-in entertainment center and a coffee station. An elegant touch that invites slow mornings, refined evenings, and effortless entertaining. Sonos surround sound flows throughout the home, creating an ambient soundtrack for daily life, while a fully integrated security and camera system offers peace of mind and quiet confidence. Complementing the home's HURRICANE-IMPACT WINDOWS, professionally INSTALLED FLOOD PANELS provide an additional safeguard, reflecting the thoughtful attention to both luxury and long-term resilience found throughout the property. The kitchen stands as a statement of both beauty and performance, where quartz countertops, solid-wood glass-front cabinetry, a sculptural range hood, designer pendant lighting, and stainless-steel Bosch appliances come together in a space crafted for culinary artistry and connection. It opens seamlessly to the dining area, where a wood-burning travertine stone fireplace adds warmth and architectural presence, setting the stage for candlelit dinners and lingering conversations. Two luxurious primary suites, one on each level offers the rare indulgence of privacy and flexibility. Each is finished with shiplap walls, porcelain tile, recessed lighting, and abundant natural light. The upper-level retreat opens to a private balcony overlooking the pool and tropical grounds, a serene perch for sunrise reflections and evening breezes. Its spa-inspired ensuite features a quartz walk-in shower, while the first-floor primary bath is appointed with a solid-wood double vanity, continuing the home’s narrative of tailored craftsmanship and understated elegance. Completing the residence are two additional bedrooms with a shared bath and an upstairs bonus room ideal for recreation, fitness, or creative pursuits. Beyond the interiors, the estate reveals its most captivating chapter. The backyard unfolds as a secluded resort, where a glistening pool and spa are framed by layered, well-established tropical landscaping that has matured into a living wall of privacy. Covered and open-air lounges invite both sun-drenched afternoons and starlit evenings, while a turf-lined grilling and gathering area provides an elevated setting for alfresco dining. Just beyond the palms, the canal stretches quietly behind the property, creating the illusion that the waterway is an extension of your own grounds and inviting a lifestyle of boating, paddleboarding, and sunset cruises from your private dock. When you venture beyond this sanctuary, the unmistakable charm of Holmes Beach awaits.

506 58th Street, Holmes Beach
Start Your Search