Location: Holmes Beach
Do Not Show Listings
504 59TH ST, HOLMES BEACH, FL 34217
$1,795,00090 Days on yellowkey MLS ID: A4677906
Bed: 3 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 3126 Built: 2006 Tax: $8,402 (2025)Community: Holmes Beach 16Th UnitSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,402
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Live the island lifestyle in this custom-built, ELEVATED canal home located in a quiet, no-HOA neighborhood just minutes from the heart of Holmes Beach. Built in 2006, this well-constructed residence offers peace of mind, privacy, and easy access to everything Anna Maria Island is known for—beaches, local dining, boutique shopping, and waterfront parks. The home features an open, multi-level layout designed for comfortable island living, with three spacious bedrooms, multiple balconies and porches, and CANAL and OPEN-WATER views from several levels. The primary bedroom is privately located on the first living level, offering convenience and separation from the additional bedrooms above. Boating enthusiasts will appreciate the private dock with deep-water access and NO BRIDGE RESTRICTIONS, allowing quick access to open water. Additional features include an ELEVATOR, METAL ROOF, four-car garage, ample storage, and room to add a pool for enhanced outdoor living. As one of the few elevated homes in the area, this property offers notable structural integrity and the opportunity to enjoy Anna Maria Island living with confidence.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jessica Batten (941-962-3380)
506 58TH ST, HOLMES BEACH, FL 34217
$3,400,00078 Days on yellowkey MLS ID: A4679359
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3319 Built: 1963 Tax: $24,569 (2024)Community: Holmes Beach 14Th UnitSingle Family
Taxes:$24,569
Tax Year: 2024
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.
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Mike Polachek (941-524-0241)
2918 AVENUE E, HOLMES BEACH, FL 34217
$1,800,000349 Days on yellowkey MLS ID: A4650561
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2262 Built: 1997 Tax: $6,613 (2024)Community: IlexhurstSingle Family
Taxes:$6,613
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. This incredible home is built like a fortress. This architect designed concrete tri-level residence was constructed with artistry and represents a masterpiece of strength framed by a concrete girdle wrapped around solid pilings. Wake up to the scent of salt in the air and the sound of waves just steps away, this is not a vacation, this is your everyday! Picture yourself walking barefoot at the beach just about 500 feet from your home, everyday! The European 2 person elevator glides you through 2262 square feet encompassing 3 bedrooms, 2 bathrooms, an open kitchen, dining room and multiple living areas to the rooftop retreat where Gulf views await stretching endlessly Westward. The details of this home are custom for this one of a kind beach residence. Features include richly hued cherry wood floors, a 2025 primary bathroom shower conversion, electric roll-down hurricane shutters for peace of mind, a 2024 newer roof, a 2025 hurricane rated garage door and poured in place concrete exterior stairs located on the North and South.. Utilities are located underground. Enjoy Caribbean quality sunsets night after night over the gulf for jaw dropping vistas. Step onto one of the breezy balconies with your morning coffee for an incredible way to begin your day! At day's end, climb on up again to your private rooftop perch, kick back and inhale the sea air. Whether you're lounging in the living areas, gathering with friends in the family room, taking in panoramic views of the Gulf or taking the elevator down for a barefoot walk on the shoreline to collect shells and watch the sunset you'll be living your life like a vacation - every day! Be sure to check out the 3D Virtual Tour. One or more photo(s) has been virtually staged.
Listing is courtesy of: WAGNER REALTY (941-761-3100)
Listing Agent: Sherry Flathman (941-592-3433)
505 75TH ST, HOLMES BEACH, FL 34217
$2,700,000206 Days on yellowkey MLS ID: A4665534
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 3778 Built: 1985 Tax: $15,606 (2024)Community: Island HomesSingle Family
Taxes:$15,606
Remarks: Discover paradise at this stunning canal front retreat that includes 5 bedrooms and 3.5-bathrooms. Located in the heart of Holmes Beach just a short stroll to the Gulf Beaches, restaurants, shops and more! This renovated gem offers modern elegance situated on a serene canal with direct access to Tampa Bay, ideal for boat lovers! Step inside to an open-concept living space, featuring Brazilian walnut floors, fireplace and natural light that shines through the impact hurricane windows and doors. Enjoy the gourmet kitchen, complete with custom cabinetry, sleek stainless steel appliances, marble countertops and more! The master suite is conveniently located on the main level with a walk in closet and a fireplace. It is a private oasis, boasting a spa-inspired ensuite with dual vanities and a walk-in shower. Four additional bedrooms provide ample space for family, guests, or a home office/gym. Outside, your tropical haven awaits. Dive into the sparkling pool, relax on the expansive deck, or take your boat straight from your private dock to explore the open waters. With lush landscaping and breathtaking canal views, this backyard is perfect for sunset gatherings or quiet mornings with coffee in hand. Located just steps from the pristine beaches of Anna Maria Island, this home offers the ultimate Florida lifestyle. This home has been lovingly enjoyed and very well taken care of by the full time owners. Schedule your private tour today!
Listing Agent: Jason Sato (941-778-7200)
8302 MARINA DR, HOLMES BEACH, FL 34217
$995,000108 Days on yellowkey MLS ID: A4675825
2 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1986 Tax: $5,125 (2024)Community: Holmes Beach 34Th UnitSingle Family
Taxes:$5,125
Remarks: Under contract-accepting backup offers. ALL RESONABLE OFFERS CONSIDERED!!! Elevated two-bedroom, two-bath home situated on a large lot in a quiet area of Holmes Beach. This well-maintained property features new hurricane-rated windows and sliders, providing comfort and peace of mind. A wraparound screened porch allows you to enjoy sun or shade throughout the day, ideal for relaxing or entertaining. The updated kitchen features quartz countertops, solid wood cabinetry, and a pantry with pull-out shelving for excellent storage and functionality. A gas cooktop is a desirable upgrade rarely found on the island. The primary bedroom includes an ensuite bathroom with a marble-top vanity and an oversized tile shower. The second bedroom offers access to a Jack-and-Jill bathroom and a convenient laundry room closet. Both bedrooms feature spacious walk-in closets. The expansive downstairs area provides ample room for parking, storage, and beach gear, along with an additional enclosed space offering flexible use as a hobby room, workshop, or storage area. Across the street are private, deeded docks; this property includes an unimproved dock space (#22), conveyed by a separate deed. The home has been lovingly cared for, has never been used as a rental, and is being offered turn-key furnished. A large enclosed backyard provides excellent privacy and ample room for a pool. Elevated construction and a generous lot enhance functionality and outdoor potential. Conveniently located near the beach, shopping, and dining, this home is ideal for full-time living, a vacation retreat, or an investment opportunity. Enjoy the 3-D view and walk around this comfy home!
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Cindy Jones (941-773-9770)
405 28TH ST, HOLMES BEACH, FL 34217
$2,995,000241 Days on yellowkey MLS ID: TB8418360
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3748 Built: 1972 Tax: $27,499 (2024)Community: Sunrise Park RepSingle Family
Taxes:$27,499
Remarks: Price Reduction! This newly renovated waterfront home on Anna Maria Island features nearly 80 feet of prime canal frontage, providing breathtaking views from almost every room of the property. A private boat dock and lift make this residence a paradise for boating enthusiasts, while also being only steps away from the beach. Step inside to discover a spacious open-concept living room with vaulted ceilings and two large balconies. A modern kitchen outfitted with high-end appliances, ample storage, and chic finishes overlooks your private pool and spa. The master bedroom features access to the back patio leading to the pool plus walk-in closet. The spa-like master bathroom centers around your stand-alone tub and frameless glass shower with dual his and her vanities. Recent renovations include electrical, plumbing, and air conditioning systems, impact-rated windows, new exterior siding, plus a new seawall and a new metal roof. Schedule your showing today!
Listing is courtesy of: PINEYWOODS REALTY LLC (813-225-1890)
Listing Agent: Lawrence Vargas (813-505-4808)
634 KEY ROYALE DR, HOLMES BEACH, FL 34217
$3,175,00051 Days on yellowkey MLS ID: A4683541
Bed: 4 Bath: 3.5 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 2011-built canal-front residence offering over 3,000 square feet of refined coastal living in one of Anna Maria Island’s most sought-after neighborhoods. Positioned high and built to modern standards, 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. 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 seeking a newer-build, low-maintenance waterfront home with strong construction and immediate boating access, 634 Key Royale Drive delivers exceptional value on Anna Maria Island.
Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC (941-224-3304)
Listing Agent: Jason Hrnak (941-773-6572)
607 NORTH POINT DR, HOLMES BEACH, FL 34217
$1,795,00049 Days on yellowkey MLS ID: A4682874
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1884 Built: 1987Monthly Fee: $117 Tax: $22,261 (2025)Community: Key RoyaleSingle 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Hannah Hillyard (941-744-7358)
424 62ND ST, HOLMES BEACH, FL 34217
$699,999380 Days on yellowkey MLS ID: A4645810
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1098 Built: 1974Monthly Fee: $100 Tax: $9,951 (2025)Community: Seaside Gardens RepSingle Family
Taxes:$9,951
Remarks: This beautifully restored, income producing property can be yours! Welcome to Island Delight on Anna Maria Island. Offered TURNKEY furnished with an active rental history and brand new roof, this property provides flexible options to enjoy paradise. Primely located just a few blocks from the turquoise waters and powdery sand of the Gulf, you can enjoy the the island's serene beauty whenever you wish. You'll love the private, heated, saltwater pool and spa as you walk through the gates of this charming home--adorned with beautiful pavers. Inside you'll find an inviting space with a large kitchen equipped with all new stainless steel appliances, kitchen cabinetry and fixtures. The granite countertops are a nice touch with bar seating at the peninsula. The bathroom is conveniently positioned between the two spacious bedrooms. The living space boasts an open concept to the spacious dining area, and an exterior door that leads out to your secluded and fenced deck area. The grand back yard space/deck is equipped with a sitting area, grilling space, outdoor shower and adorable shed for all your beach gear. The parking pad is large enough for two vehicles which makes parking on the island seamless! The community of Seaside Gardens has a low monthly HOA fee that includes water which makes owning a pool very cost effective. Even more, you have access to tennis courts, pickleball courts, shuffleboard, basketball court and a playground! With its unbeatable location and income potential, this property is an exceptional investment opportunity.
Listing Agent: Jessica Uglik, Pllc (941-212-7098)
204 66TH ST, HOLMES BEACH, FL 34217
$2,750,000173 Days on yellowkey MLS ID: A4669141
0 Days Off yellowkey (back on 3/28/2026)
Bed: 6 Bath: 5.0 Liv Area Sq Ft: 3472 Built: 2013 Tax: $46,263 (2025)Community: West Wind ShoresSingle Family
Taxes:$46,263
Remarks: Under contract-accepting backup offers. Paradise is Here! 6-Bedroom, 5-Bathroom Furnished, Turnkey Island Retreat in Holmes Beach Welcome to your dream beachside escape: This stunning 3-level single-family home is located just one block from the powdery sand beaches of the Gulf coast in highly sought-after Holmes Beach on Anna Maria Island. Weather you're Looking for a lucrative investment property or a private island oasis, this fully furnished, turnkey residence offers the best of both worlds. With 6 bedrooms and 5 bathrooms in total, there's plenty of room for everyone to spread out and enjoy the ultimate island lifestyle. This property boasts prime walkable access to the beach while maintaining a sense of privacy and tranquility. Highlighting each floor, the First Floor has a 2-car garage and a versatile bonus/game room with direct access to the pool and patio. The Second Floor features a Bright and airy open-concept kitchen, living and dining spaces, complete with a cozy dinette for casual meals. Three spacious bedrooms, two full bathrooms, and a convenient laundry room complete this level. The Third Floor provides a luxurious primary suite with a spa-like ensuite bathroom, two additional oversized bedrooms, and another 2 full bathrooms. The beautifully landscaped, fenced backyard is a true tropical paradise featuring a private pool and spa, along with outdoor dining and lounging areas perfect for relaxing or entertaining. Investors will appreciate the solid rental income potential while private buyers can immediately move in and embrace the laid-back Florida lifestyle. Don't miss this rare opportunity to own a slice of paradise on Anna Maria Island!
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: David Ahrens, Pllc (650-288-7661)
5803 IMPERIORE AVE, HOLMES BEACH, FL 34217
$1,150,000136 Days on yellowkey MLS ID: A4673548
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1969 Tax: $13,135 (2024)Community: Neptunes GardensSingle Family
Taxes:$13,135
Remarks: Smart Buyers: This Price Improvement Is For You. Weekly rental! Exceptional Investment Steps from Holmes Beach. Welcome to Blue Oasis, a fully renovated ground-level retreat just steps from Holmes Beach and the turquoise waters of the Gulf of Mexico. This stunning 2-bedroom, 2-bath home combines modern luxury with island charm. Featuring a versatile den with a pocket door for added privacy, it’s perfect for a home office or guest space. The den includes a stylish daybed with trundle, offering extra sleeping accommodations without sacrificing comfort or design. Every detail has been thoughtfully upgraded, including a new roof (Summer 2025), freshly finished walls, baseboards, doors, and paint throughout, plus custom closet organizers for added functionality. The kitchen and both bathrooms feature all-new soft-close cabinetry and fixtures, complemented by brand-new appliances—dishwasher, refrigerator, gas range/oven, and washer. Comfort is ensured with a new A/C (November 2024-mounted up from the ground), while the new pool pump with Pentair automation adds convenience and efficiency. The master bath boasts a completely redesigned shower with new tile and hardware, and the entire home is furnished with all-new furniture and décor, from beds, mattresses, and nightstands to a stylish sofa, chairs, dining set, and coastal accents. Outdoors, enjoy new patio furniture, umbrellas, lighting, and a perfect sized pool with optional spa jets plus a shed stocked with new beach chairs and a beach cart. Rinse off in the outdoor shower offering both hot and cold water. Additional upgrades include new TVs in every room, palm tree shutters, creating a turnkey property that’s ready to impress. With its prime location just a four-minute walk to the beach, easy access to shops and dining, and exceptional rental performance, Blue Oasis delivers a fantastic ROI and lifestyle appeal—perfect as a short-term rental, second home, or long-term investment in one of Florida’s most sought-after coastal markets. Make your move on this turnkey coastal gem today!
Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)
Listing Agent: Shauna Ruby (941-544-2070)
510 69TH ST, HOLMES BEACH, FL 34217
$1,070,00077 Days on yellowkey MLS ID: A4679951
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1500 Built: 1976 Tax: $5,314 (2024)Community: Bay Palms AddSingle Family
Taxes:$5,314
Remarks: This stunning completely renovated 2-bedroom, 2-bathroom home offers 1,500 square feet of bright, open-concept living space designed for effortless island lifestyle. Step inside to find a seamless flow between the gourmet kitchen, dining area, and spacious living room—perfect for relaxing with friends, family gatherings, or simply soaking in the Florida sunshine that pours through large windows. The thoughtful renovation shines through with contemporary finishes, high-quality fixtures, and a fresh, inviting palette that feels brand new yet timeless. Both bedrooms provide comfortable retreats, while the well-appointed bathrooms add a touch of luxury. Situated on a prime lot in desirable Holmes Beach, you'll enjoy generous outdoor space—ideal for morning coffee, evening barbecues, or creating your own tropical oasis. Just moments from the sands of Manatee Public Beach and the calm Gulf waters, this home puts you in the center of Anna Maria Island's relaxed charm: pristine beaches, boutique shops, waterfront dining, and easy access to everything the island offers.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Craig O'Rourke (877-366-2213)
518 74TH ST, HOLMES BEACH, FL 34217
$2,700,000195 Days on yellowkey MLS ID: A4666701
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2343 Built: 1969 Tax: $22,274 (2024)Community: Bay PalmsSingle Family
Taxes:$22,274
Remarks: Under contract-accepting backup offers. Tropical Waterfront Oasis in Holmes Beach! Welcome to 518 74th Street, a stunningly remodeled coastal retreat that captures the essence of island living. This open-concept residence offers 3 spacious bedrooms, 3.5 luxurious baths, and is being sold designer furnished for a move-in ready experience. Step inside to find a chef’s kitchen with high-end finishes, custom cabinetry, and generous counter space perfect for entertaining. Each bedroom features its own walk-in closet and private bath, blending comfort with elegance. Outside, paradise awaits with 80 feet of deep sailboat-water frontage, a new seawall, and direct boating access to the Gulf. The backyard is a private tropical sanctuary, complete with a resort-style pool and spa surrounded by lush mature landscaping and fruit trees. Just a short stroll to the beach, this home offers the perfect blend of luxury, relaxation, and convenience. Whether you’re seeking a full-time residence or a vacation escape, this tropical waterfront gem is ready to welcome you.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Charles Buky (941-228-6086)
611 DUNDEE LN, HOLMES BEACH, FL 34217
$1,789,000130 Days on yellowkey MLS ID: A4673753
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1735 Built: 1970 Tax: $11,540 (2025)Community: Key Royale 9Th AddSingle Family
Taxes:$11,540
Remarks: Welcome to your beautifully renovated coastal retreat on Anna Maria Island, perfectly situated on a peaceful canal with direct access to Bimini Bay and the Intracoastal waterways with no bridges in your way. From the moment you arrive, the curb appeal sets the tone with fresh stucco, crisp new exterior paint, and a circular driveway that brings you to your private coastal oasis. Step inside to a bright, modern living space that showcases tile flooring throughout and a full interior transformation framed by crown molding. A spacious den/flex room expands the home’s versatility, offering the perfect spot for a cozy lounge, guest space, office, or anything your lifestyle calls for. The heart of the home is the chef’s kitchen, thoughtfully redesigned with custom cabinetry, upgraded quartz countertops, and all new high-end appliances including a top-of-the-line Wolf dual fuel range with a custom hood. The layout flows effortlessly for entertaining or everyday living, giving the space an elevated yet welcoming feel. The primary bedroom features a beautifully designed ensuite bathroom with a seamless glass shower, coastal-inspired tilework, and a custom-built walk-in closet. The second bedroom offers plenty of space and sits conveniently near the guest bathroom, which showcases the same elevated coastal finishes found in the primary suite. Just off the main living area, the indoor laundry room adds convenience with a brand new Speed Queen washer and dryer. Make your way to the backyard to take in the true essence of canal-front living. A brand new in-ground heated saltwater pool and spa creates a private resort-style oasis, surrounded by serene water views that invite you to unwind or entertain in style. Enjoy a boat dock with a 10,000 pound lift and direct access to open water for effortless boating adventures. Recent improvements include a new Trane HVAC system and a one-year-old Rinnai tankless water heater for added efficiency and comfort. The home also offers updated PVC drainage, copper wiring, and impact windows throughout, giving you long-term confidence and peace of mind. This ideal location places you just around the corner from a nine-hole executive golf course and only a short golf cart ride away from Anna Maria Island’s award-winning beaches, charming boutiques, and coastal dining. With luxury updates, thoughtful design, and unbeatable access to the water, this home offers the best of island living. Schedule your showing today!
Listing Agent: Kaisen Mitchell (941-726-7657)
4118 5TH AVE, HOLMES BEACH, FL 34217
$2,495,00018 Days on yellowkey MLS ID: A4687756
Bed: 6 Bath: 3.5 Liv Area Sq Ft: 2786 Built: 2009 Tax: $12,482 (2025)Community: Villas On Fifth AveSingle Family
Taxes:$12,482
Remarks: Welcome to your dream coastal retreat on Anna Maria Island—where luxury, location, and income potential come together seamlessly. This stunning 6-bedroom, 4-bathroom elevated home is a rare find—a property of this size and scale can no longer be built in Holmes Beach. Perfectly positioned just steps from the public beach and turquoise waters of the Gulf, as well as nearby restaurants, shopping, and local attractions, this Mediterranean-style home delivers the ultimate island lifestyle. Thoughtfully designed for both comfort and high-performing investment, it boasts an exceptional rental history to match. Inside, you’ll find a spacious, thoughtfully designed layout ideal for hosting large groups and families. The home features an open floor plan, high ceilings, spacious bedrooms, a 4-person elevator, and multiple balconies, including private outdoor spaces off both primary suites and an additional balcony off the kitchen—perfect for morning coffee, sunset cocktails, or simply enjoying the coastal breeze. The heart of the home opens into a bright, airy living space, complemented by lower level bonus game room that adds an extra layer of entertainment and flexibility. An elevator provides seamless access to all three levels, while ample storage throughout ensures everyday comfort and convenience. Step outside to your own private paradise—a true backyard oasis featuring a sparkling pool, relaxing jacuzzi, a covered dining area, and a spacious conversation lounge—offering the perfect setting to unwind and entertain after a day at the beach. Major recent upgrades (2025), totaling over $100,000, include a new terracotta tile roof, a new pool pump and heater, updated soffits and fascia, and refreshed and reenforced rear decking—providing peace of mind and long-term value. Additional highlights include: Parking for up to 6 vehicles—a rare island luxury Proven rental income with 10 years of consistent, stellar reviews Strong rental projections exceeding $150,000 annually Whether you're searching for a high-performing investment property, a second home, or a full-time coastal escape, this Anna Maria Island gem checks every box.
Listing Agent: Adrienne Carter (310-428-0200)
628 DUNDEE LN, HOLMES BEACH, FL 34217
$4,250,000134 Days on yellowkey MLS ID: A4672773
2 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 3788 Built: 2019 Tax: $34,499 (2024)Community: Key Royale 9Th AddSingle Family
Taxes:$34,499
Remarks: Waterfront Luxury Awaits YOU! Experience the ultimate Anna Maria Island lifestyle in this stunning custom-built, canal-front residence, perfectly positioned on a quiet street in Key Royale of Holmes Beach. Built with impeccable craftsmanship and thoughtful design, this exceptional 4-bedroom, 5-bathroom home delivers coastal elegance and resort-style living just steps from the sugar-white sands of the Gulf of Mexico. Step inside to soaring ceilings, an abundance of natural light, and high-end finishes throughout. The open-concept great room flows seamlessly to the outdoor living spaces which includes an outdoor kitchen with a green egg and dining. Convenient full pool bath and 2 laundry rooms to note! A true standout feature is the temperature-controlled 500+ bottle wine cellar – an exquisite touch for the discerning collector. The gourmet kitchen is a chef’s dream, featuring premium appliances like Wolf induction cooktop, custom cabinetry, and a large center island that overlooks the canal, dual dishwashers, and a walk-in pantry. Each of the four spacious bedrooms offers privacy and comfort, with luxurious en-suite bathrooms and generous closet space. Outside, paradise unfolds: a heated pool and spa invite year-round relaxation, while the expansive covered lanai and low-maintenance artificial turf create a lush, private oasis. Boaters will love the private dock with 16,000 lb boat lift and direct access to Tampa Bay and the Gulf – no bridges, quick out to open water. Additional highlights include are wet bar with mini fridge for effortless entertaining, Whole-home generator for complete peace of mind, Two-car garage with epoxy flooring, Elevated construction and impact-resistant windows/doors, extra storage room, and a huge outdoor shower. This is more than a home – it’s a lifestyle. Properties with this combination of luxury finishes, waterfront access, and thoughtful design rarely come available. Schedule your private showing today!
503 BAYVIEW DR, HOLMES BEACH, FL 34217
$899,00083 Days on yellowkey MLS ID: A4676121
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1960 Tax: $4,973 (2025)Community: Sunrise Park RepSingle Family
Taxes:$4,973
Remarks: One or more photo(s) has been virtually staged. Reduced, ACT FAST! Three-bedroom Anna Maria Island beach home, 300 steps to the island's world class beaches! This Holmes Beach retreat, located on Anna Maria Island, is ready and waiting for you! Discover this fully updated, bright and airy split plan, three-bedroom home spanning over 1,100 square feet, thoughtfully designed with open living space combining the kitchen and living room areas. Located on a quiet cul-de-sac, this home sits right in the Island’s sweet spot between the Cortez and Manatee Bridges, providing easy access on and off the island. You’re just a short walk or golf cart ride away from white sandy beaches, restaurants, shops, and a convenient free trolley stop. You will see all properties were not created equal as you step into your own tropical, completely private backyard oasis complete with screened in lanai, wet bar and highly sought after southern exposure. Bask in the sun, don't sit in the cold shadows with a subpar exposure. Enjoy a beautiful, heated saltwater pool equipped with sprayers, fountains, and a sun platform for ultimate relaxation. A multilevel waterfall pond adds to the tranquil atmosphere, featuring a charming bridge that leads you over the pond directly to the gorgeous pool area. The expansive 9,000-square-foot lot is enhanced by landscaping stones, providing ease of maintenance. The home features a metal roof and impact windows for peace of mind. It boasts 2025 appliances, including a washer and dryer, along with all-new cabinetry and quartz countertops in both the kitchen and master bath. Fresh paint and 5-inch base molding through-out complete the modern look and feel. This property is offered turnkey furnished and is rental ready for monthly stays. RV and boat parking allowed! There is nothing to do here but relax and enjoy your surroundings: take a dip in the pool, stroll to the beach, indulge in the varied dining options this island has to offer, from tiki bars to fine dining. Enjoy the manatees and dolphins playing in the canal across the street and parrots flying overhead! Immerse yourself in all the serenity and joys this beautiful island has to offer. Whether you’re seeking relaxation or adventure, this home provides the perfect base for enjoying Anna Maria Island’s unique charm and vibrant lifestyle. All NEW in 2025, Washer, Dryer, Refrigerator, Range, Dishwasher, Microwave, High Velocity Range Hood, Pool Heater, Pool Pump, Water Heater, Kitchen Cabinets and Quartz Countertops, Master Bath Cabinets and Quartz Countertop, Guest Bathroom with New Vanity and Top, All Furniture and Bedding. Impact Windows installed 2021 and 2022, Metal Roof installed 2018.
Listing is courtesy of: REALTY MARK ASSOCIATES (561-245-5400)
Listing Agent: Raymond Nesci (941-468-1608)
635 KEY ROYALE DR, HOLMES BEACH, FL 34217
$7,485,00020 Days on yellowkey MLS ID: A4687421
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3648 Built: 2015 Tax: $55,473 (2025)Community: Key Royale 8Th AddSingle Family
Taxes:$55,473
Remarks: This bayfront Key Royale home is ideally situated on the southern side of Key Royale, offering a more protected setting away from the north wind and enhancing year-round outdoor enjoyment. Truly a World of Its Own—delightful bayfront living with sweeping views of the crystal-clear waters of Anna Maria Sound and Tampa Bay. This elevated, single-level custom-built coastal residence is a tribute to exceptional design, premier location, and impeccable construction, finishes, and taste. Calm coastal hues and shell stone travertine flooring flow throughout the soaring living spaces, highlighted by tongue-and-groove ceilings with solid wood beams. The home showcases custom cabinetry with 100-year-old pine accents, extensive millwork, and a handcrafted TV feature wall. Additional features include a Control4 AV system, upgraded custom lighting and fans, an elevator, 8-foot solid core interior doors, whole-home sound system, plantation shutters, custom motorized window treatments, and central vacuum. The chef’s kitchen is equipped with Thermador commercial-grade appliances, a built-in pantry, and double laminated-edge granite countertops. Expansive bay views are captured from nearly every angle, while sliding glass doors open to an elegant 63-foot balcony complete with an outdoor kitchen and Trex staircase leading to the pool area below. Three of the four bedrooms are ensuite, all featuring rich Ipe wood flooring, custom closet systems, and luxurious bathrooms finished with travertine flooring and Moen body spray shower systems. Built to the highest standards, the exterior boasts a commercial-grade 24-gauge standing seam metal roof, PGT impact windows and doors, second-floor block construction, poured concrete porches, a Cantera entry door, and Icynene attic insulation. The spacious garage includes insulated doors and durable epoxy flooring. Outdoors, the home transforms into a private waterfront retreat with a bayside freeform pool and spa, expansive travertine deck for lounging and dining, and a covered cabana. Boating enthusiasts will appreciate the Trex dock with water and electric, along with 28,000 lb and 10,000 lb boat lifts. This stunning residence is a decorator’s masterpiece and a true feast for the senses. It presents a rare opportunity to embrace an extraordinary coastal lifestyle. Sold turnkey furnished less personal exceptions!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Ryan Sheck (863-581-4005)
302 67TH ST, HOLMES BEACH, FL 34217
$1,450,000129 Days on yellowkey MLS ID: A4674440
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1552 Built: 1960Community: 67Th Coastal Cottages Or2448/1887Single Family
Taxes:
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Remarks: This one has it all! Beautifully remodeled with a fabulous updated kitchen and open floor plan, this 3 bedroom/2 bath half duplex lives like a single family home, with a private, heated pool and just steps to the direct beach access! Ideally situated on a quiet corner lot in the heart of the island, it is a popular vacation rental! The split bedroom plan is perfect for hosting, and the updated pool and trellis invite you to step out your family room sliders and enjoy the Florida sunshine. Don’t miss a minute of relaxation in the coastal charm of the beach inspired décor, with wainscoted walls, freshly painted interior, white wood trim, tile flooring throughout, recessed lighting, stainless steel appliances, quartz counters, farmhouse sink and white shaker style cabinetry to the ceiling. You will love your large primary en suite, with a walk out to the pool, high ceilings, and a bathroom with dual vanity and a walk in shower. Your spacious guest rooms are privately situated and enjoy ample natural light through large windows. This slice of paradise is perfectly situated, with easy beach access and just down the street from the free trolley stop. Enjoy your island time stress free in this like-new spot, and enjoy the benefits of the short term rental income when you’re not on island time!
Listing Agent: Erin Leathem (941-448-5616)
104 SUNSET LN, HOLMES BEACH, FL 34217
$16,750,000125 Days on yellowkey MLS ID: A4674426
Bed: 5 Bath: 6.5 Liv Area Sq Ft: 8962 Built: 2023Community: Sunset CoveSingle Family
Remarks: Imagine owning a beach retreat on an island beloved by travelers from around the world yet still cherished for its warm, small-town charm. Newsweek recently named Anna Maria Island the #1 Most Popular Beach Town in America, and nestled along its pristine shoreline is Sunset Dream, an extraordinary 8,563 sq ft under-air contemporary beachfront estate designed to celebrate panoramic Gulf views at every turn. Every element of this fully furnished, modern masterpiece is intentional and bespoke. Imported “corner-less” wraparound glass walls frame 180-degree vistas of the Gulf of Mexico, creating an uninterrupted connection to the shoreline. The chef-inspired kitchen redefines entertaining with a layout that allows guests to watch the cooking experience as if they’re part of a live culinary show. A secondary hidden catering kitchen supports large gatherings with ease. This gourmet space includes a dual-faucet Galley Workstation® sink, full-size Sub-Zero® refrigerator and freezer, dedicated red and white wine coolers, a beverage bar, and a built-in Frame® TV. The main living area showcases curated Menotti® Italian furnishings, a white grand piano, a sleek linear gas fireplace, and exquisite finishes that highlight superior craftsmanship. Oversized Euro Doors® open fully, inviting the outdoors in and creating a spectacular indoor–outdoor lifestyle. For game days or cinematic evenings, the media room is a standout feature. Hand-cut paulownia wood wall coverings warm the space, while smart home controls dim the room and bring a 155" screen to life. A smoked-oak bar and dual keg system elevate the experience. The third-level primary suite continues the theme of breathtaking Gulf views with its own floor-to-ceiling wraparound glass walls. A built-in breakfast bar and custom leather bed with a hidden TV lift offer comfort and luxury. The spa-inspired primary bath includes dual water closets and a sculptural tub surrounded by corner-less glass overlooking the beach, a true statement of artistry and retreat. The ground-level terrace is an oasis designed for relaxation and connection. Lounge beside the full-sized pool with in-water bar seating, unwind in the spa, or admire the dramatic one-story waterfall. The space seamlessly opens to a poolside bar and indoor entertaining lounge. To complete the experience, Sunset Dream is equipped with a comprehensive smart home and security system and comes fully furnished for immediate enjoyment. Close at noon and toast to your new lifestyle with a glass of wine at sunset, right from your terrace as the sky melts into the Gulf.
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