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401 39th Street, Holmes Beach

Coastal Elegance Meets Modern Luxury Just Minutes from the Gulf. Discover the ultimate island living with this newer custom-built luxury beach home, just moments from the pristine shores of the Gulf. Designed for both style and functionality, this home features 4 spacious bedrooms, 4.5 bathrooms, plus a private study and inviting den, offering flexible spaces for work, relaxation, or entertaining. The heart of the home is the gourmet kitchen, boasting an oversized eat-in island, state-of-the-art appliances, and sleek, high-end finishes - a dream for any chef or entertainer. A private elevator provides easy access to all levels, while the 4-car garage ensures plenty of space for vehicles, beach gear, and more. Every material, finish, appliance, and fixture has been thoughtfully curated, with a list available. Whether you're seeking the perfect family beach retreat or vacation rental, this home offers the ultimate blend of luxury, comfort, and island lifestyle. Enjoy the convenience of being just a short walk to the beach, local shops, groceries, and popular island restaurants, putting the best of Anna Maria Island right at your doorstep.

4 Beds ⋅ 5 Baths ⋅ Casanas Sub SubDv. ⋅ 34217 Zip Code

Coastal Elegance Meets Modern Luxury Just Minutes from the Gulf. Discover the ultimate island living with this newer custom-built luxury beach home, just moments from the pristine shores of the Gulf. Designed for both style and functionality, this home features 4 spacious bedrooms, 4.5 bathrooms, plus a private study and inviting den, offering flexible spaces for work, relaxation, or entertaining. The heart of the home is the gourmet kitchen, boasting an oversized eat-in island, state-of-the-art appliances, and sleek, high-end finishes - a dream for any chef or entertainer. A private elevator provides easy access to all levels, while the 4-car garage ensures plenty of space for vehicles, beach gear, and more. Every material, finish, appliance, and fixture has been thoughtfully curated, with a list available. Whether you're seeking the perfect family beach retreat or vacation rental, this home offers the ultimate blend of luxury, comfort, and island lifestyle. Enjoy the convenience of being just a short walk to the beach, local shops, groceries, and popular island restaurants, putting the best of Anna Maria Island right at your doorstep.

3702 5th Avenue, Holmes Beach

$2,500,000

Set along the shimmering Gulf shoreline in the heart of Holmes Beach, this rare Anna Maria Island parcel invites you to bring your coastal vision to life. Just moments from powdery white sands and within easy reach of the area’s charming boutiques, local dining, and laid-back island attractions, the location strikes an ideal balance between tranquility and vibrant beach town energy. Whether you imagine a striking custom residence designed to capture sweeping Gulf views and unforgettable sunsets, or you’re looking to secure a prime investment in a highly desirable destination, the possibilities here are as expansive as the horizon. This is more than a homesite, it’s an opportunity to create a personalized retreat where every day feels like a getaway.

Casanas Sub SubDv. ⋅ 34217 Zip Code

Set along the shimmering Gulf shoreline in the heart of Holmes Beach, this rare Anna Maria Island parcel invites you to bring your coastal vision to life. Just moments from powdery white sands and within easy reach of the area’s charming boutiques, local dining, and laid-back island attractions, the location strikes an ideal balance between tranquility and vibrant beach town energy. Whether you imagine a striking custom residence designed to capture sweeping Gulf views and unforgettable sunsets, or you’re looking to secure a prime investment in a highly desirable destination, the possibilities here are as expansive as the horizon. This is more than a homesite, it’s an opportunity to create a personalized retreat where every day feels like a getaway.

3720 Gulf Drive, Holmes Beach

$1,700,000

PRICE IMPROVEMENT on this Ultimate Gulfside Retreat on Holmes Beach, Anna Maria Island! Successful Vacation Rental with WEEKLY RENTALS and NO HOA! Just 200 feet from the sugar-sand shores and turquoise waters of the Gulf of America! This updated, coastal-inspired three-level beach home with a private elevator offers the perfect blend of luxury, comfort, and investment potential. With over 2,000 sq. ft. of bright, open living space, 3 bedrooms, 3 Ensuite Bathrooms, plus a Half Bath, a private pool and hot tub, and SWEEPING GULF VIEWS from your balcony, this is truly the ultimate island escape. Currently a high-performing vacation rental generating over $120,000 annually with future bookings in place, this property also makes an ideal primary residence or second home. Offered fully furnished—including sleeper sofas—it’s ready to comfortably accommodate family, friends, and guests. The main level boasts a light-filled OPEN CONCEPT LIVING AREA with large windows and sliding glass doors overlooking lush tropical landscaping. The CHEF'S KITCHEN features newer stainless-steel appliances, dual refrigerators, expansive granite counters, a wine cooler, and Walk In Pantry. Entertaining is effortless with a breakfast bar, indoor dining space, and outdoor dining options. The primary suite on this level is a private retreat with dual walk-in closets and a spa-style ensuite bath featuring both a shower/tub combo and a separate walk-in shower, plus a water closet with bidet. Take the private elevator to the upper level where you’ll find a SECOND PRIMARY SUITE beautiful bathroom and walk-in closet, a third spacious bedroom with ensuite bathroom, and a separate laundry room. The ground floor welcomes you with a large foyer and a VERSITILE FLEX SPACE, perfect for storage, crafts, or a media room, along with access to the OVERSIZED 2-CAR GARAGE! Additional upgrades include a reverse osmosis system and three newer air conditioners for consistent comfort throughout the home. Step outside to your private, fenced outdoor oasis, complete with sparkling POOL, bubbling HOT TUB, and plenty of seating for lounging or alfresco dining while enjoying the Gulf breezes and breathtaking sunsets. Perfectly situated at Holmes Beach with its vibrant shops, restaurants and beaches, and less than 2 miles from the shops beaches and restaurants of Bradenton Beach—and just steps from the Gulf. Longboat Key, Sarasota, Siesta Key and SRQ Airport are also close by. This rare property combines island living at its best with proven rental income. Schedule your private showing today—your Anna Maria Island paradise awaits!

3 Beds ⋅ 4 Baths ⋅ Casanas Sub SubDv. ⋅ 34217 Zip Code

PRICE IMPROVEMENT on this Ultimate Gulfside Retreat on Holmes Beach, Anna Maria Island! Successful Vacation Rental with WEEKLY RENTALS and NO HOA! Just 200 feet from the sugar-sand shores and turquoise waters of the Gulf of America! This updated, coastal-inspired three-level beach home with a private elevator offers the perfect blend of luxury, comfort, and investment potential. With over 2,000 sq. ft. of bright, open living space, 3 bedrooms, 3 Ensuite Bathrooms, plus a Half Bath, a private pool and hot tub, and SWEEPING GULF VIEWS from your balcony, this is truly the ultimate island escape. Currently a high-performing vacation rental generating over $120,000 annually with future bookings in place, this property also makes an ideal primary residence or second home. Offered fully furnished—including sleeper sofas—it’s ready to comfortably accommodate family, friends, and guests. The main level boasts a light-filled OPEN CONCEPT LIVING AREA with large windows and sliding glass doors overlooking lush tropical landscaping. The CHEF'S KITCHEN features newer stainless-steel appliances, dual refrigerators, expansive granite counters, a wine cooler, and Walk In Pantry. Entertaining is effortless with a breakfast bar, indoor dining space, and outdoor dining options. The primary suite on this level is a private retreat with dual walk-in closets and a spa-style ensuite bath featuring both a shower/tub combo and a separate walk-in shower, plus a water closet with bidet. Take the private elevator to the upper level where you’ll find a SECOND PRIMARY SUITE beautiful bathroom and walk-in closet, a third spacious bedroom with ensuite bathroom, and a separate laundry room. The ground floor welcomes you with a large foyer and a VERSITILE FLEX SPACE, perfect for storage, crafts, or a media room, along with access to the OVERSIZED 2-CAR GARAGE! Additional upgrades include a reverse osmosis system and three newer air conditioners for consistent comfort throughout the home. Step outside to your private, fenced outdoor oasis, complete with sparkling POOL, bubbling HOT TUB, and plenty of seating for lounging or alfresco dining while enjoying the Gulf breezes and breathtaking sunsets. Perfectly situated at Holmes Beach with its vibrant shops, restaurants and beaches, and less than 2 miles from the shops beaches and restaurants of Bradenton Beach—and just steps from the Gulf. Longboat Key, Sarasota, Siesta Key and SRQ Airport are also close by. This rare property combines island living at its best with proven rental income. Schedule your private showing today—your Anna Maria Island paradise awaits!

220 36th Street, Holmes Beach

$1,260,000

Discover your slice of paradise on Anna Maria Island! This meticulously maintained, ELEVATED, turnkey furnished, home offers the quintessential Gulf Beach lifestyle, located just ONE BLOCK from the pristine gulf beaches, you can effortlessly walk to sun, sand, and surf. Featuring 3 bedrooms & 3 bathrooms, this elevated home provides ample space for relaxation and entertaining. Step into a world of comfort and style with new flooring throughout, creating a fresh and inviting open atmosphere. The remodeled kitchen, boasting gorgeous quartz countertops and stainless steel appliances, is perfect for entertaining. Relax and unwind in your private, heated pool, surrounded by lush, tropical landscaping that ensures complete privacy. Enjoy your morning coffee or evening cocktails on one of the multiple lanais, designed for ultimate relaxation. The outdoor dining area is perfect for al fresco meals with family and friends. Leave the car behind and stroll to the charming shops, delectable dining, and convenient grocery store that Anna Maria Island offers. This prime location offers unparalleled convenience. The spacious garage provides a fantastic opportunity for a game room or convenient golf cart parking. Impact windows/sliding doors and newer tile roof provide peace of mind and enhanced energy efficiency. Importantly, the elevated design ensured this property remained untouched by recent storm damage to the living space. This home is a PROVEN VACATION RENTAL, generating consistent income - 2023 - 129K, 2024 - 124K, 2025 - 100K+ so far, and 2026 - 37K so far and is ready for its next fortunate owner. Don't miss this chance to own a piece of paradise on Anna Maria Island, where every day feels like a vacation. Schedule your showing today!"

3 Beds ⋅ 3 Baths ⋅ Casanas Sub SubDv. ⋅ 34217 Zip Code

Discover your slice of paradise on Anna Maria Island! This meticulously maintained, ELEVATED, turnkey furnished, home offers the quintessential Gulf Beach lifestyle, located just ONE BLOCK from the pristine gulf beaches, you can effortlessly walk to sun, sand, and surf. Featuring 3 bedrooms & 3 bathrooms, this elevated home provides ample space for relaxation and entertaining. Step into a world of comfort and style with new flooring throughout, creating a fresh and inviting open atmosphere. The remodeled kitchen, boasting gorgeous quartz countertops and stainless steel appliances, is perfect for entertaining. Relax and unwind in your private, heated pool, surrounded by lush, tropical landscaping that ensures complete privacy. Enjoy your morning coffee or evening cocktails on one of the multiple lanais, designed for ultimate relaxation. The outdoor dining area is perfect for al fresco meals with family and friends. Leave the car behind and stroll to the charming shops, delectable dining, and convenient grocery store that Anna Maria Island offers. This prime location offers unparalleled convenience. The spacious garage provides a fantastic opportunity for a game room or convenient golf cart parking. Impact windows/sliding doors and newer tile roof provide peace of mind and enhanced energy efficiency. Importantly, the elevated design ensured this property remained untouched by recent storm damage to the living space. This home is a PROVEN VACATION RENTAL, generating consistent income - 2023 - 129K, 2024 - 124K, 2025 - 100K+ so far, and 2026 - 37K so far and is ready for its next fortunate owner. Don't miss this chance to own a piece of paradise on Anna Maria Island, where every day feels like a vacation. Schedule your showing today!"

4002 6th Avenue, Holmes Beach

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