Location: Holmes Beach
Do Not Show Listings
2806 GULF DR, HOLMES BEACH, FL 34217
$1,095,00020 Days on yellowkey MLS ID: A4686689
1 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 1500 Built: 1995 Tax: $14,829 (2025)Community: IlexhurstSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,829
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Effortless Island Living at this elevated 3BD/2BA home, where breezy interiors and sunlit spaces create the perfect island escape just steps from the sand. Located in a highly desirable weekly rental zone, this property offers exceptional flexibility and income potential. Inside, the living and dining area welcomes you with abundant natural light and easy access to the expansive front deck. The kitchen features generous counter space and a breakfast bar, making entertaining effortless, while the split bedroom layout provides comfort and privacy. Downstairs, an oversized garage delivers convenience with tandem space for up to four vehicles, along with plenty of room for beach gear, bikes, and additional storage. The low maintenance outdoor space lets you spend more time enjoying the coastal lifestyle, whether you're heading out for sunset walks or relaxing in the ocean breeze from the deck. With its unbeatable location, strong rental appeal, and inviting coastal feel, this property checks lots of the boxes. Bring your decorator touches and create your personal island vibe. Easy access on and off the island, close to shopping, dining, a trolley stop and the beach is right at your back door. What more or you waiting for? Make this your perfect little slice of island life!
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Darcie Duncan (941-779-0304)
4105 4TH AVE, HOLMES BEACH, FL 34217
$2,690,000243 Days on yellowkey MLS ID: TB8414779
Bed: 6 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 2453 Built: 2014 Tax: $32,227 (2024)Community: Villas On Fourth AveSpa: YesSingle Family
Taxes:$32,227
Tax Year: 2024
Remarks: STEPS FROM THE GULF – LUXURY SIX-BEDROOM COASTAL RETREAT IN HOLMES BEACH | Discover Summer’s Retreat, an architectural masterpiece where luxury meets the legendary white sands of Anna Maria Island. This remarkable six-bedroom, six-and-a-half-bath coastal estate represents one of the island’s most coveted properties—a rare find featuring six private en-suite bedrooms that seamlessly blend family sanctuary with proven investment excellence. Step into an oasis of sophisticated design where every detail has been thoughtfully curated. The expansive open-concept living space flows effortlessly from room to room, bathed in natural light that dances across premium finishes. The gourmet chef’s kitchen stands as the heart of the home, showcasing lustrous quartz countertops, professional-grade stainless steel appliances, and an impressive bar-top island that beckons both intimate conversations and grand celebrations. Four private balconies serve as personal retreats, each capturing the gentle Gulf breezes and offering front-row seats to nature’s daily theater. Crown this experience atop the spectacular rooftop deck, where panoramic sunsets paint the sky in brilliant oranges and pinks over the endless Gulf waters. The outdoor experience rivals any world-class resort. Immerse yourself in the heated saltwater pool with its luxurious sun shelf, perfect for lounging with a morning coffee or evening cocktail. The therapeutic spa provides the ultimate relaxation after days spent exploring island treasures. Tropical landscaping creates an intimate paradise, while the expansive covered patio transforms into an entertainer’s dream. The dedicated outdoor dining area and professional grilling station make every meal an event, whether hosting friends or enjoying quiet family moments under the stars. Location is everything, and Summer’s Retreat delivers the extraordinary. Literally steps across the street from pristine Manatee Beach access, your morning walk to sugar-sand shores takes mere moments. The vibrant Anna Maria Island Beach Café becomes your neighborhood gathering spot, while playgrounds ensure endless fun for families. The island’s charm extends beyond your doorstep—boutique shops, acclaimed restaurants, and the complimentary island trolley create a car-free lifestyle where every amenity is within reach. This isn’t just a home; it’s a gateway to the Anna Maria Island experience. Summer’s Retreat has established itself as a premier vacation rental destination, consistently generating exceptional returns for discerning investors. The unique combination of six en-suite bedrooms, luxury amenities, and unbeatable location creates unparalleled demand among visitors seeking the ultimate island experience. This property offers the rare opportunity to enjoy your own slice of paradise while building wealth through one of Florida’s most sought-after rental markets. Whether you envision lazy mornings on private balconies, sunset celebrations on your rooftop deck, or poolside gatherings with loved ones, Summer’s Retreat transforms every day into a vacation. This is more than a home—it’s your personal resort, your investment sanctuary, and your gateway to the incomparable Anna Maria Island lifestyle. Experience the extraordinary. Your coastal legacy awaits.
Listing is courtesy of: ENGEL & VOLKERS ST. PETE (727-295-0000)
Listing Agent: Leisa Mohler-Erickson (239-789-7106)
4003 5TH AVE, HOLMES BEACH, FL 34217
$1,495,000174 Days on yellowkey MLS ID: A4669926
REDUCED by $3,000 (0.2%) on 04/02/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2200 Built: 2003 Tax: $22,346 (2024)Community: CasanasSingle Family
Taxes:$22,346
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
Remarks: Mediterranean-inspired coastal luxury just one block from the Gulf—this fully furnished, elevated single-family villa, “Island Oasis,” offers no HOA, complete privacy, and proven storm resilience with no damage to upper living areas. Solid construction, turnkey condition, and major system updates provide immediate peace of mind, especially with income projections between 153-193k annually, for those interested in renting. This exceptional Anna Maria Island retreat comfortably accommodates 8+ guests, featuring two king suites, a third bedroom suite with two queen beds, and additional sleeping space in the great room—ideal for personal use, multigenerational living, or income-producing potential. Recent upgrades include new roof (2024), refrigerator (2024), dishwasher (2025), washer/dryer (2024), AC units (2020 & 2017), and water heaters (2025 & 2019), along with a resurfaced pool with new coping, pavers, heater, and pump. Inside, the home showcases light-filled interiors, soaring ceilings, crown molding, and natural wood accents, blending refined coastal design with relaxed island comfort. The open-concept kitchen features wood cabinetry, tile backsplash, an eat-at island, and newer stainless appliances, flowing seamlessly into the main living and dining areas. Glass sliders open to a front piazza and private pool courtyard, creating effortless indoor-outdoor living. The primary suite offers a private balcony and a spa-style bath complete with a clawfoot soaking tub and walk-in shower, delivering a true owner’s retreat. Above it all, a rooftop terrace captures 360° sunrise and sunset views, with peek-a-boo Gulf and Bay views, setting the stage for unforgettable evenings in the delightful island breeze. Step outside and experience the Florida lifestyle—sun-drenched pool days, shaded terraces, and lush tropical landscaping create a private oasis just moments from the beach. A short walk leads you to the soft white sands of the Gulf, while nearby favorites like Skinny’s, Manatee Beach, Pine Avenue, boutique shopping, waterfront dining, and the free island trolley make island living effortless. Elevated, meticulously maintained, and offered fully furnished, this is a rare opportunity to own a resilient, income-capable coastal home in one of Florida’s most sought-after destinations. Anna Maria Island living at its finest—sun, sand, and effortless coastal luxury await.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Jo-Lee Mansfield (843-303-7463)
608 GLADSTONE LN, HOLMES BEACH, FL 34217
$1,835,00044 Days on yellowkey MLS ID: A4684704
REDUCED by $50,000 (2.7%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1692 Built: 1972Monthly Fee: $8 Tax: $17,697 (2024)Community: Key Royale 15Th AddSpa: NoSingle Family
Taxes:$17,697
Remarks: Tucked within the exclusive waterfront community of Key Royale on Anna Maria Island, this beautifully renovated canal-front residence offers an exceptional blend of island charm, privacy, and effortless island living. Designed to embrace the Florida lifestyle, the home is centered around a spectacular pool courtyard, where almost every room opens to the expansive outdoor living space, creating a seamless connection between indoors and out. Bathed in natural light due to its desirable southern exposure, the home invites sun-filled days by the pool and tranquil evenings under the coastal sky. The thoughtfully designed split floor plan features a private primary suite with ensuite bath, along with two additional guest bedrooms and a well-appointed second bathroom, offering comfort and flexibility for family and visiting guests. The home offers a new roof and seawall was replaced in 2006, ensuring lasting quality and peace of mind for years to come. Ideally situated on a deep-water canal, the property provides a 10,000 lb boat lift and dock with water and electric. Direct access to Tampa Bay, the Gulf of Mexico, and the Intracoastal Waterway, make it a dream for boating enthusiasts and lovers of life on the water. Also, located just moments from Anna Maria Island’s world-renowned beaches, charming boutiques, and acclaimed dining, this residence captures the essence of luxury coastal living in one of the island’s most coveted neighborhoods. Don't miss this extraordinary opportunity to experience the elegance, serenity, and waterfront lifestyle that make Key Royale truly exceptional.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Becky Sirigotis (941-201-8000)
234 85TH ST, HOLMES BEACH, FL 34217
$1,774,999377 Days on yellowkey MLS ID: A4648191
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1715 Built: 1989 Tax: $11,241 (2024)Community: Holmes Beach Thirty-Third UnitSpa: NoSingle Family
Taxes:$11,241
Remarks: Tucked away on a quiet, picturesque street in the heart of Holmes Beach, this ELEVATED WATERFRONT retreat offers a rare private coastal sanctuary. Perfectly positioned on a sprawling 225-foot waterfront SAILBOAT-DEPTH CANAL with NO FIXED BRIDGES and DIRECT ACCESS to Bimini Bay, the Intracoastal Waterway, and the shimmering GULF OF MEXICO. Wrapped in lush, tropical landscaping and framed by a natural mangrove shoreline, a 40+ ft TimberTech COMPOSITE DOCK stretches gracefully into the water; ready to welcome your large boat or sailboat. What sets this home apart is not just its breathtaking setting, but the peace of mind it offers. ELEVATED and STORM-TESTED, this home proudly boasts ZERO HURRICANE DAMAGE - a true rarity on the island. Built with an impressive LIST OF UPGRADES for ultimate resilience: breakaway garage walls REINFORCED with CONCRETE SUPPORTS, a 2023 standing seam ALUMINUM ROOF with underlayment that is MIAMI-DADE STANDARDS, HURRICANE-IMPACT windows and doors with UV protection, and hidden vent soffits and fascia. Step inside and feel the relaxed elegance of this coastal gem. SUNLIGHT floods through every room, dancing off the stunning plank-style porcelain tile floors and creating a warm, inviting atmosphere. The OPEN CONCEPT great room flows seamlessly into a beautifully updated kitchen where your inner chef can run wild. Outfitted with rich maple cabinetry, sparkling Quartz countertops, and top-tier stainless steel appliances. The oversized walk-in pantry is perfect for keeping all your culinary essentials tucked away. The home's bathrooms echo the same attention to detail, featuring gorgeous tilework, granite countertops, upgraded Toto commodes, and brand-new copper piping and plumbing (2025). Every corner has been meticulously cared but it’s the outdoor living that truly sets this property apart. Your private backyard oasis was designed for both relaxation and unforgettable entertaining. Expansive WRAP-AROUND DECKING, crafted from premium materials and beautifully maintained, offers plenty of space to gather with family and friends. The FENCED IN DECKING also is perfect for pets to roam safely, while the CUSTOM KAYAK LAUNCH invites spontaneous paddles through the tranquil canal waters. Dreaming of a pool? APPROVED PLANS are ready and waiting to transform this outdoor space into your personal tropical paradise. Down at the dock, life slows down. Watch dolphins play, drop a line, or simply sip a cool drink as the sun melts into the Gulf horizon. The wide canal offers ample space for larger vessels - a true rarity on the island. Additional features include a spacious 3-CAR GARAGE with TWO LARGE STORAGE areas perfect for paddleboards, fishing gear, or even a golf cart. Conveniently, a 50-amp outlet has been installed for a RV, boat lift or even a hot tub. Ample guest parking is a major plus when it comes to this property and could even accommodate a RV, boat with trailer or whatever your heart desires! Plus a proactive termite protection system. Best of all? This serene retreat is just a short stroll to the sugar-sand beaches of Anna Maria Island, charming local shops, and island-favorite restaurants - all easily accessible via the free island trolley. Whether you’re searching for a full-time coastal residence, a seasonal getaway, or a savvy investment (zoned R-1 with 30-day minimum rentals), this home checks every box. Come experience the magic of Holmes Beach waterfront living where every day feels like a vacation.
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Mike Polachek (941-524-0241)
727 KEY ROYALE DR, HOLMES BEACH, FL 34217
$3,800,000427 Days on yellowkey MLS ID: TB8348338
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3640 Built: 1988Monthly Fee: $150 Tax: $45,927 (2024)Community: North Point Harbour Unit ThreeSingle Family
Taxes:$45,927
Remarks: Experience an unparalleled coastal retreat in the exclusive North Point Harbor enclave of Holmes Beach, situated on the highly coveted northern end of Anna Maria Island. This meticulously maintained, 3,640 sq. ft. custom-built estate is a waterfront masterpiece, offering direct, deep-water access to the Gulf of Mexico and Tampa Bay from the prestigious, quiet shores of Key Royale. The residence features a thoughtful and expansive layout consisting of 5 bedrooms plus a versatile bonus room and 6 bathrooms (4 full, 2 half), perfectly blending grand-scale functionality with sophisticated artisan craftsmanship. Built with a focus on both aesthetic elegance and structural longevity, the home boasts a durable metal roof, refined vinyl wood and tile flooring throughout the open-concept living spaces, and two massive balconies specifically designed to capture breathtaking, panoramic water views from nearly every room. For the maritime enthusiast, the property’s private dock and dedicated boat slip provide the ultimate convenience: effortless, no-bridge navigation for a yacht or sportfish, allowing for easy access to the open waters of the Gulf or the fishing grounds of Egmont Key. Beyond the residence, the lifestyle is defined by the unique character of Anna Maria Island (AMI). Known for its "Old Florida" charm, AMI strictly limits high-rise development, ensuring unobstructed views and sunset vistas. This golf-cart-friendly community allows for a seamless transition from the front door to the pristine white sands of the Gulf beaches or the boutique shops and world-class dining found along Pine Avenue and Gulf Drive. The Key Royale area is revered for its serenity, offering a private golf club and a tranquil atmosphere tucked away from main thoroughfares. North Point Harbor further elevates this experience with meticulously maintained grounds and private tennis courts for residents. Strategically positioned, the property is a short boat ride or drive from the cultural hubs of Sarasota and St. Petersburg, providing a quiet escape from the hustle and bustle of mainland life. This home offers the security of an impeccable history with no flood damage, standing as a move-in-ready property maintained to the highest technical standards. Whether hosting a gathering in the chef-inspired kitchen, enjoying a quiet evening on the screened lanai overlooking the pool, or launching a vessel for a sunset cruise, this property offers a lifestyle of coastal elegance and resort-style luxury. It is a standout choice for any buyer who values infrastructure as much as aesthetics. From the durable building envelope to the artisan-finished interiors, every detail of this Key Royale estate has been curated to provide a high-quality home in a sought-after island destination. Embrace the island life where the only daily deadline is the sunset, and the backyard is a gateway to the finest waterways in the world.
Listing is courtesy of: ENGEL & VOLKERS TAMPA DOWNTOWN (813-863-1986)
Listing Agent: Razin Mcfarland (813-484-0519)
6201 HOLMES BLVD, HOLMES BEACH, FL 34217
$1,450,000124 Days on yellowkey MLS ID: A4675506
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 1822 Built: 1968 Tax: $9,121 (2025)Community: Holmes Beach 17Th UnitSpa: NoSingle Family
Taxes:$9,121
Remarks: INCREDIBLE VALUE! 5 BEDROOM HOME ON ANNA MARIA ISLAND WITH PROVEN RENTAL HISTORY- THIS IS THE ONE!!! Imagine owning a place where every day feels like a vacation. Located on a peaceful corner lot in the heart of Holmes Beach, this spacious 5-bedroom pool home offers the perfect balance of relaxed island living and modern comfort—just steps from everything that makes this island so special. Designed for connection and comfort, the home features an airy, open layout filled with natural light and coastal character. The kitchen anchors the space with recent updates, stainless steel appliances, and generous prep areas, making it ideal for hosting family and friends after long beach days. Sliding glass doors lead to a private outdoor retreat, where a sun-drenched pool, expansive patio, and side courtyard create a setting made for entertaining, relaxing, and making memories. The primary suite feels like a private escape, complete with an updated bathroom, walk-in closet, and direct access to the pool—perfect for morning swims or quiet evenings outdoors. With five bedrooms accommodating up to 10 guests, the home offers flexibility for full-time living, extended stays, or hosting visitors with ease. Major upgrades add value and peace of mind, including fully renovated bathrooms, updated kitchen features, and a metal roof installed in 2022. The home is thoughtfully maintained and ready to be enjoyed from day one. What truly sets this property apart is the lifestyle. Walk to the sugar-white beaches of the Gulf, bike to local cafés and shops, enjoy sunset strolls, and embrace the easygoing rhythm that makes Anna Maria Island one of Florida’s most beloved coastal communities. Weekly rentals are permitted, providing the option to enjoy the home while also benefiting from its income potential. Whether you’re searching for a beach home, a family getaway, or a smart island investment, this Holmes Beach property delivers space, location, and lifestyle—all in one unforgettable setting. Come experience why people fall in love with Anna Maria Island… and never want to leave.
Listing Agent: Christy Travis (941-545-5284)
212 72ND, HOLMES BEACH, FL 34217
$2,985,000349 Days on yellowkey MLS ID: A4651200
Bed: 4 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 2272 Built: 2019 Tax: $23,423 (2023)Community: 7173900; West Wind Shores; Lot 16; Block 21; Pb 7/Spa: YesSingle Family
Taxes:$23,423
Tax Year: 2023
Remarks: Newly renovated - Stunning 4-bedroom, 6.5-bath is perfect for beach lovers just a block from the Gulf of Mexico beaches. This island home features a backyard with a private pool and tiki bar, hot tub, BBQ area, covered patio with a foosball table, and a rooftop deck with water views. The main living space, includes a kitchen with a beautiful backsplash and quartz countertops, solid wood cabinets, island seating, couches, and a bright dining room with access to a covered deck overlooking the pool. The third floor hosts the primary bedroom, a private balcony with rooftop deck access, and an ensuite bathroom with a double vanity and a large shower. Outdoor amenities also include a pool, spa, This home is just a quick walk to the beach, and guests can easily take the trolley to Pine Ave for local delicacies, fish at the historic AMI city pier, or kayak in the bay waters.
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)
Listing Agent: Gregg Bayer (941-799-9096)
529 67TH ST, HOLMES BEACH, FL 34217
$1,499,00076 Days on yellowkey MLS ID: TB8471553
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1308 Built: 1972 Tax: $6,858 (2024)Community: Bay Palms AddSpa: NoSingle Family
Taxes:$6,858
Remarks: Welcome to your slice of island living in the heart of Holmes Beach. Perfectly positioned on a deep-water canal, this 2- bedroom, 2-bath ground-level home offers the ultimate Florida lifestyle for boaters and beach lovers. With a 60-foot dock equipped with water and electric, a 10,000 lb boat lift, you can launch your boat, kayak, or paddle board directly from your backyard. Southern exposure bathes the property in warm natural light, making the winter months especially enjoyable while enhancing outdoor living year-round. Inside, the home is thoughtfully designed for comfort and efficiency, featuring Simonton Storm Seeker high-impact windows throughout, contributing to low maintenance and utility costs. Step outside and enjoy island-style living with a covered pergola and patio, plus an enclosed outdoor shower to rinse off after a day on the water or at the beach, which is three blocks away. Whether you’re searching for a full-time residence, vacation home, or investment opportunity, this canal-front gem delivers the best of boating, beach access, and easy island living in one exceptional property.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
215 64TH ST, HOLMES BEACH, FL 34217
$3,095,000154 Days on yellowkey MLS ID: A4671772
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2690 Built: 2008 Tax: $13,043 (2025)Community: Casa Del Mare Vii CondoSpa: YesSingle Family
Taxes:$13,043
Remarks: Discover the Coastal Chic Beach House, a stunning residence featuring four bedrooms and 3.5 baths, which has undergone an impressive transformation by renowned interior designer Adrian Griffin. This home is designed for multi-generational living and boasts an array of sophisticated interior elements including an elevator and a high end Aerus whole house air filtration system, a custom bunk room, and exquisite designer tile and millwork. The main floor showcases a spacious kitchen and dining area equipped with luxurious quartz countertops and new LG and GE appliances. Designed with an open layout, the living space is bright and inviting, adorned with modern coastal furnishings. Glass doors seamlessly connect the interior to the sun deck, perfect for soaking up the beautiful Florida weather. A conveniently placed staircase provides easy access to the pool and spa area. The primary suite offers easy access to an open deck on the front of the home. The expansive bathroom has a walk in shower and soaking tub with custom coastal tile. On the upper level, you will find an ensuite, two generously sized bedrooms, a three-person bunk room, and an additional large bathroom. The decor throughout reflects a contemporary coastal aesthetic that exudes timeless elegance. The exterior features a a large private back yard with a Tiki Hut and generously sized freeform pool, recently resurfaced, complemented by a custom spa. Lush tropical landscaping is enhanced by programmable color lighting that illuminates the front and back gardens. The covered lanai offers a shaded and rain proof area ideal for entertaining, while glass doors lead to a bonus room equipped with ping-pong table. Conveniently situated within walking distance to the beach and local shops and restaurants, this property also provides easy access to a trolley stop. This beach house is an ideal second home or vacation rental, fully furnished and ready for occupancy with everything needed from beach gear to baby essentials. To schedule your exclusive private showing, please contact the listing agent—24-hour notice is appreciated.
130 50TH ST, HOLMES BEACH, FL 34217
$2,799,00057 Days on yellowkey MLS ID: A4683830
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2947 Built: 2010 Tax: $37,816 (2024)Community: The Villas On 50Th StreetSingle Family
Taxes:$37,816
Remarks: Own the sunset and step into a lifestyle buyers dream about—and renters actively seek out. Just moments from the Gulf, this stunning 6-bedroom, 4.5-bath coastal retreat delivers the perfect blend of luxury, comfort, and exceptional income potential. Designed to host and impress, the home lives like a private resort. Outside, guests are drawn to the resort-style pool with a sun shelf, a relaxing hot tub, and a tranquil waterfall feature. The outdoor bar and expansive patio create an effortless entertaining space, while the rooftop deck offers unforgettable Gulf-view sunsets that elevate every stay. Inside, the bright, open-concept design is made for connection, comfortably accommodating large groups, families, or vacation guests. High-end finishes meet relaxed coastal style, creating a space that feels both upscale and welcoming—exactly what today’s buyers and renters are looking for. Whether you're building a strong vacation rental portfolio or securing your own coastal escape, this property stands out as a high-demand, memory-making destination with proven appeal.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Lisa Tucker (863-206-2938)
401 28TH ST, HOLMES BEACH, FL 34217
$1,800,00075 Days on yellowkey MLS ID: A4681048
REDUCED by $180,000 (9.1%) on 04/17/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1656 Built: 1965 Tax: $15,915 (2025)Community: Sunrise ParkSpa: YesSingle Family
Taxes:$15,915
Remarks: Wake up to coastal living in this beautifully remodeled 3-bedroom, 2-bath canal-front home designed for relaxed island life. Spend your mornings paddle boarding or kayaking from your backyard, afternoons boating with easy access to the Intracoastal, Tampa Bay, and Gulf of America, and evenings unwinding in your private pool and spa. The stylish kitchen features high-end Thor appliances, perfect for entertaining after a day on the water. New flooring throughout, a spacious garage, and dedicated parking for a boat trailer or RV add everyday convenience. Lush tropical landscaping surrounds the property, and the beach is just a quick, easy walk away, bringing the best of waterfront and beachside living together in one exceptional home.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Amy Ward (386-623-2525)
531 72ND ST, HOLMES BEACH, FL 34217
$4,500,00040 Days on yellowkey MLS ID: A4685680
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3500 Built: 1959 Tax: $11,428 (2025)Community: Bay Palms Add 8Th UnSingle Family
Taxes:$11,428
Remarks: Spectacular bay views define this recently renovated 4-bedroom, 4-bath waterfront home in Holmes Beach, set on a large bayfront lot with exceptional waterfrontage and sweeping open water vistas. Positioned at the end of a quiet bayside street, the property captures some of the most expansive bay views on Anna Maria Island. Renovated within the past year, the home blends updated finishes with distinctive architectural details and inviting gathering spaces. The main living area features a wood burning fireplace, while large windows and sliding glass doors frame the bay and fill the home with natural light. A tongue-and-groove wood ceiling adds warmth and coastal character throughout the primary living space. The updated kitchen includes built-in appliances, custom cabinetry, and generous prep space, opening to the dining and living areas for easy entertaining. A standout feature is the second-floor great room, an expansive and versatile retreat offering elevated water views and abundant natural light. The space includes 4 day beds, a full bath, and an adjacent artist space, creating flexible accommodations for guests or creative pursuits. Outdoor living takes full advantage of the setting with a private pool and expansive waterfront patio areas overlooking the bay, providing ideal spaces for lounging, dining, and enjoying coastal breezes and stunning sunsets. Located just moments from the beaches, shops, and restaurants of Anna Maria Island, this property offers recent renovations, generous living spaces, and exceptional bayfront views in one of Holmes Beach's most desirable waterfront settings.
Listing Agent: Dee Munn (407-346-4422)
607 NORTH POINT DR, HOLMES BEACH, FL 34217
$1,795,00057 Days on yellowkey MLS ID: A4682874
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1884 Built: 1987Monthly Fee: $117 Tax: $22,261 (2025)Community: Key RoyaleSpa: NoSingle Family
Taxes:$22,261
Remarks: CANAL FRONT IN KEY ROYALE - NORTH POINT HARBOUR WITH COMMUNITY POOL AND TENNIS COURTS. Experience unparalleled luxury in this exquisite and elevated waterfront home. Beautifully remodeled with a NEW ROOF (2025) and turnkey furnished 3-bedroom, 2-bathroom waterfront home, offering nearly 2,000 square feet of luxurious living space and includes a community pool and tennis courts! The home sits at 11 feet elevation and had no flood damage. Located in the highly sought-after North Point Harbour community of Key Royale on Anna Maria Island, this home epitomizes an idyllic blend of elegance and tranquility. Having undergone tasteful renovations, this canal-front gem is fully furnished and move-in ready. It boasts 83 feet of waterfront with a private dock and a 12,000 lb boat lift, allowing you to embark on sunset cruises directly from your backyard into the open water with no bridges obstructing your path. The primary suite is a true retreat with a balcony overlooking the water, complete with a luxurious en-suite bathroom, walk-in closet. Additional bedrooms are generously sized and elegantly appointed. A lovely courtyard patio overlooking the water invites you to enjoy the outdoors and dine alfresco. North Point Harbour residents enjoy exclusive access to the community pool, tennis and pickleball courts, and clubhouse. Additionally, you have the option to join the private Key Royale Golf Club, featuring the island’s only golf course, along with dining and social activities. This home is just a golf cart ride away from Anna Maria Island’s stunning beaches and all its attractions, perfect for embracing the island lifestyle year-round or as a seasonal retreat. This home combines the best of luxury living with the beauty and serenity of a waterfront setting. Don’t miss the opportunity to make this dream home yours.
Listing Agent: Hannah Hillyard (941-744-7358)
215 81ST ST, HOLMES BEACH, FL 34217
$1,500,0006 Days on yellowkey MLS ID: A4690200
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2020 Built: 2002 Tax: $9,235 (2025)Community: Beachwalk Twnhms Ph 2Spa: YesSingle Family
Taxes:$9,235
Remarks: Nestled near the north end of Anna Maria Island, 215 81st Street is a three-bedroom, two and a half bath home boasting over 2,000 square feet of living space—an Airbnb gem zoned for weekly rentals. Just two blocks from some of the island’s most pristine beaches, this property offers a true tropical paradise out back. The fully fenced oasis features a gorgeous pool with a built-in hot tub, while the expansive paver-lined lounge area creates a true island escape. The elevated design includes a two-car garage and a game room—currently set up with a ping pong table but offering ample space to add additional attractions for guests. The second floor invites you into a bright, open living, dining, and kitchen area with a half bath, complemented by a massive, screened-in balcony deck (freshly screened in less then a year ago) overlooking the pool oasis below—perfect for soaking in the tropical ambiance. You will also find a dedicated interior laundry room with full size washer and dryer on this floor as well. On the third floor, you’ll find three spacious bedrooms and two full baths, with the primary suite offering not only luxury but also absolutely gorgeous views from every angle—a panoramic reminder of the beauty that surrounds you on Anna Maria Island. This home is packed with recent updates: a 2022 roof, 2019 AC, and a brand-new water heater. The exterior shines with hardie board siding installed less than a year ago and fresh paint. Beyond the home, you’re a stone’s throw from Pine Avenue’s charm and all that Anna Maria offers—laid-back vibes, local eateries, and coastal culture. Fully furnished and turnkey, this is both a thriving investment and an island escape waiting for you.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Johnny Hopper, Pa (941-524-1706)
506 58TH ST, HOLMES BEACH, FL 34217
$3,300,00086 Days on yellowkey MLS ID: A4679359
REDUCED by $100,000 (2.9%) on 04/19/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3319 Built: 1963 Tax: $24,569 (2024)Community: Holmes Beach 14Th UnitSpa: YesSingle Family
Taxes:$24,569
Remarks: 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. 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. This is more than a home—it is a refined island retreat, custom crafted for those who seek privacy, comfort, and tranquility, with the rare privilege of a secluded waterfront setting and immediate access to one of Florida’s most cherished beach communities.
634 KEY ROYALE DR, HOLMES BEACH, FL 34217
$3,175,00059 Days on yellowkey MLS ID: A4683541
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3020 Built: 2011 Tax: $43,872 (2024)Community: Key Royale 7Th AddSingle Family
Taxes:$43,872
Remarks: Elevated waterfront living in Key Royale — built for confidence, designed for ease. Welcome to 634 Key Royale Drive, a thoughtfully built canal-front home offering over 3,000 square feet of refined coastal living in one of Anna Maria Island’s most sought-after neighborhoods. Designed for buyers seeking island living, boatable water access, and a low-maintenance lifestyle, this home delivers peace of mind along with sweeping water views from nearly every room. Bright, sun-filled interiors open seamlessly through French doors to a private outdoor retreat featuring a heated pool, Trex dock, 10,000-lb boat lift, and jet ski lift — ideal for boaters who want quick access to Tampa Bay and the Gulf. Equipped with a private irrigation well, providing a cost-efficient water source for maintaining the lawn and landscaping, the outdoor space is as practical as it is inviting. Inside, the kitchen has just been refreshed with new quartz countertops and pairs beautifully with stainless appliances and an oversized breakfast bar built for gathering. Two brand-new AC units provide efficient climate control, complemented by Icynene spray-foam insulation and two Rinnai tankless water heaters for energy-conscious living. The main-level primary suite captures peaceful canal views and features dual vanities, a soaking tub, and custom port windows. Upstairs offers three additional guest bedrooms, two baths, and a breezy balcony overlooking the water. Built with impact-rated windows and doors and showing no storm damage to date, this elevated home offers the structural integrity today’s buyers are seeking — without sacrificing comfort or style. An oversized garage with 12’ ceilings and a 9’ door easily accommodates a boat, golf cart, or additional storage. Located in the desirable Key Royale community of Holmes Beach, you’re minutes to the beach, golf, dining, and island favorites — yet tucked away in a quiet canal setting. For buyers looking to enjoy the best of Anna Maria Island with minimal upkeep and immediate boating access, 634 Key Royale Drive delivers a rare combination of lifestyle, location, and long-term value.
Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC (941-224-3304)
Listing Agent: Jason Hrnak (941-773-6572)
15 SEASIDE CT, HOLMES BEACH, FL 34217
$599,000412 Days on yellowkey MLS ID: A4642333
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 978 Built: 1963Monthly Fee: $150 Tax: $7,635 (2024)Community: Seaside Gardens RepSingle Family
Taxes:$7,635
Remarks: Waterfront opportunity awaits on Anna Maria Island! Discover the potential to craft your ideal coastal retreat in the evolving Seaside Gardens community of Holmes Beach. With direct, no-bridge access to the Gulf, this property is perfectly suited for boating enthusiasts, offering generous dock space and a 2020 seawall backed by a transferable 60-year warranty. Located just a short half-mile from the island’s renowned sugar-sand beaches, you can enjoy sun-filled days and peaceful mornings watching the sunrise over the water. Nearby, you’ll find the best of island living—local restaurants, lively gathering spots, coffee shops, and a marina—all just minutes away. Outdoor amenities, including tennis, pickleball, and basketball courts, along with a convenient boat launch, are right around the corner. Whether you envision building a custom waterfront home overlooking Watson’s Bayou or enhancing the existing structure to unlock its full value, the possibilities here are wide open. With strong short-term rental appeal in a highly desirable location, this is a rare chance to secure your place in paradise.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Shandra Holbrook (502-905-8528)
23 SEASIDE CT, HOLMES BEACH, FL 34217
$599,000513 Days on yellowkey MLS ID: A4629905
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 978 Built: 1963Monthly Fee: $150 Tax: $9,252 (2023)Community: Seaside Gardens RepSingle Family
Taxes:$9,252
Remarks: HUGE PRICE REDUCTION – now under $600K! NEW ROOF! Investor alert! Opportunities like this on Anna Maria Island are rare, especially at this price point. Here’s your chance to bring your dream home to life in picturesque Holmes Beach within the transforming Seaside Gardens community. This is your blank canvas to create the ultimate waterfront retreat and boater’s paradise, with no bridges to the Gulf and generous dock potential allowing for quick and easy access to open water. The location is unbeatable, just 0.5 miles to the sugar-white sand beaches and even closer to the vibrant heart of Holmes Beach, where you’ll find charming restaurants, lively taverns, coffee shops, a marina, and more. You can even see the nearby boat launch from the property. For those who enjoy staying active, tennis, pickleball, and basketball courts are all just steps away. Wake up to peaceful views of Watson’s Bayou and design your ideal 2-bedroom island escape. Whether you envision a private coastal getaway or a high-performing short-term rental, the possibilities are exceptional. Don’t miss this opportunity—the island lifestyle has never been more attainable.
605 N POINT DR, HOLMES BEACH, FL 34217
$3,395,00056 Days on yellowkey MLS ID: A4683720
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3214 Built: 2012Monthly Fee: $167 Tax: $22,644 (2024)Community: North Point Harbour Unit OneSpa: NoSingle Family
Taxes:$22,644
Remarks: Nestled at one of the highest elevations on Anna Maria Island, this exceptional coastal retreat is located in the highly sought-after North Point Harbour community of Holmes Beach. Built in 2012 with hurricane-rated windows and doors, the home offers both refined elegance and peace of mind, perfectly blending luxury with the relaxed sophistication of island living. A cheerful front porch welcomes you inside, setting the tone for the warmth and charm found throughout. Soaring ceilings and gleaming marble floors create a light, airy ambiance, while coastal architectural details — including multiple porches and charming balconettes — add character and dimension to the design. The beautifully appointed living room is flooded with natural sunlight through two sets of French doors that frame tranquil canal views stretching toward Bimini Bay. These doors open to capture sunny mornings and breathtaking evening sunsets, seamlessly blending indoor and outdoor living. The open floor plan flows effortlessly into the dining and kitchen areas, creating an ideal setting for intimate family meals or hosting guests with ease. The spacious first-floor primary suite serves as a peaceful sanctuary, complete with a lovely ensuite bath and a private deck — perfect for quiet evenings under the coastal sky. Two additional bedrooms are also located on the first floor, including a second ensuite bedroom and a third bedroom with its own bath, offering comfort and privacy for family and visitors alike. Even everyday tasks feel elevated in the expansive and beautifully designed laundry and utility room, conveniently located off the kitchen and garage — a space so thoughtfully appointed it hardly feels like a utility area. The entire second floor is dedicated to a spectacular private suite. This luxurious retreat features two charming balconettes, a large walk-in closet, a spa-like ensuite bath with dual sinks, and a separate office or sitting room — an ideal haven for guests or multi-generational living. Outdoors, boating enthusiasts will appreciate the impressive 20,000-pound boat lift and expansive wraparound dock situated on a short, deep-water canal. With direct access through Bimini Bay to Tampa Bay, the Gulf of Mexico, and the Intracoastal Waterway, this property offers effortless navigation to some of Florida’s most beautiful waters. Life in North Point Harbour is as enriching as it is relaxing. Spend mornings at the nearby Key Royale Golf Club for an early tee time, afternoons joining friends at the community pool or enjoying a friendly match on the tennis courts or padel, and evenings cruising from your private dock into Bimini Bay as the sun melts into the horizon. Here, everyday flows seamlessly from recreation to relaxation, creating a true island lifestyle defined by beauty, convenience, and connection to the water. This extraordinary North Point Harbour residence embodies the very best of elevated coastal living — where thoughtful design, superior craftsmanship, and an unparalleled waterfront location come together to create a truly remarkable island home.
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