Location: Holmes Beach
Do Not Show Listings
303 55TH ST, HOLMES BEACH, FL 34217
$4,375,000107 Days on yellowkey MLS ID: A4685639
REDUCED by $120,000 (2.7%) on 05/13/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3356 Built: 2026 Tax: $9,277 (2025)Community: Holmes Beach 11Th UnitSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,277
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Brand new construction completed in 2026, luxury home in the heart of Holmes Beach on beautiful Anna Maria Island, just two blocks from the white-sand Gulf beaches. This fully professionally furnished 4-bedroom, 4.5-bath coastal retreat offers the perfect blend of modern design and island living. The open-concept floor plan features a spacious living area with high ceilings and abundant natural light, flowing seamlessly into a chef’s kitchen equipped with premium Thermador appliances, custom cabinetry, a large center island, and a convenient under-counter ice maker—perfect for entertaining family and guests. Each bedroom includes its own en-suite bath, providing privacy and comfort, while the additional half bath is ideal for visitors. Equipped with an elevator going from the ground floor to the beautiful rooftop deck. Professionally designed and sold turnkey furnished, this home is ready for immediate enjoyment or use as a luxury vacation rental. Owner will be listing it as a brand new short-term rental as well. Step outside to your private resort-style backyard oasis featuring a heated pool and spa, covered lounge area, and a custom putting green surrounded by tropical landscaping and turf along with a beautiful custom deck. Multiple outdoor entertaining spaces create the perfect setting for relaxing after a day at the beach. Located only a short stroll—approximately two blocks—from the Gulf of Mexico, this exceptional property offers easy access to pristine beaches, dining, and shopping while maintaining the privacy of a quiet island neighborhood. Whether you’re seeking a full-time residence, second home, or high-end investment property, this brand new Holmes Beach home delivers luxury, location, and the ultimate Anna Maria Island lifestyle.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sean Sabbia (813-748-8701)
528 KEY ROYALE DR, HOLMES BEACH, FL 34217
$2,650,00043 Days on yellowkey MLS ID: A4692749
REDUCED by $100,000 (3.6%) on 06/05/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2846 Built: 1959 Tax: $9,556 (2025)Community: Key Royale 1St AddSpa: NoSingle Family
Taxes:$9,556
Remarks: One or more photo(s) has been virtually staged. Welcome to this extensively renovated waterfront residence in the highly desirable Key Royale community. This 4-bedroom, 4-bath home pairs elevated coastal living with modern improvements and direct boating access to the Gulf. Renovated from top to bottom, including a redesigned chef’s kitchen features high-end finishes and opens to spacious living and entertaining areas, while each bathroom has been updated with clean, contemporary detail. The property includes a new roof, four new A/C units, updated landscaping, a new garage door, and new garage flooring. For added flexibility, the private fourth bedroom above the garage has its own entrance—ideal for guests, multigenerational living, a home office, or a bonus flex space. Designed for entertaining, the home offers a new wet bar and effortless indoor-outdoor flow. Outside, enjoy private canal frontage with a boat lift and direct Gulf access—perfect for boating and island living. Move-in ready and beautifully appointed, this home delivers luxury, versatility, and a true waterfront lifestyle just minutes from renowned beaches, dining, and shopping. Discover modern elegance and relaxed coastal charm in one of Anna Maria Island’s premier boating communities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Amy Bien (443-398-1458)
5803 DE PALMAS AVE, HOLMES BEACH, FL 34217
$1,075,000111 Days on yellowkey MLS ID: A4684894
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1010 Built: 1968 Tax: $14,839 (2025)Community: Neptunes GardensSpa: YesSingle Family
Taxes:$14,839
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
Remarks: Come make your island dream a reality! This updated 3 bed/2 bath coastal charmer is just steps to the sugar sand beach, with a heated, salt water pool with full spa features! Create your own style in this cute cottage, where the hard work has already been done for you! New Luxury Vinyl Plank throughout, fresh paint, new doors, new bathrooms, new cabinetry and new appliances, means nothing left for you to do but add your personal styling! Bring your coastal creativity and create the perfect décor for you! You will love the ease of relaxing in your open family room and cooking in your updated kitchen with breakfast bar! With 3 bedrooms and a split floor plan, you have room for guests while enjoying the privacy of your own en suite. Make this your full time island escape or enjoy the benefit of income from the short term rentals that are allowed on this quiet street just steps to the soft sand of the Gulf beach! Priced to move, so you can make it your own, this one is ready to make your beach house dream come true!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Erin Leathem (941-448-5616)
201 N HARBOR DR, HOLMES BEACH, FL 34217
$4,500,00023 Days on yellowkey MLS ID: TB8509893
Bed: 5 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 3928 Built: 1985 Tax: $18,164 (2025)Community: Sportsmans Harbor RevSpa: YesSingle Family
Taxes:$18,164
Remarks: Located in the heart of Holmes Beach on Anna Maria Island, this reimagined waterfront home offers deep-water boating access, direct Gulf views, elevator access, and a beach location that is hard to beat, just steps from the front door to the sand. Set on one of the closest canal-front streets to the beach, the property provides protected dockage, quick access to Tampa Bay, downtown St. Petersburg, and the Gulf of Mexico, along with the everyday ease of true island living. Originally rebuilt from the block in 2022 in collaboration with Richard Haas, the home was thoughtfully redesigned with clean architectural lines, quality coastal construction, and low-maintenance ownership in mind. The result is a modern Anna Maria Island waterfront residence built for comfort, efficiency, and long-term durability without sacrificing style, function, or quality. Inside, the living spaces were designed to maximize natural light and keep water views connected to daily life. The main living area, kitchen, and secondary primary suite all capture direct Gulf views, while large glass openings connect the interior spaces to the outdoor terraces. A custom floating red oak staircase serves as a striking architectural focal point and adds warmth to the clean modern design. The kitchen was designed for both entertaining and everyday use, featuring Cosentino Quartz counters, custom full-height cabinetry, JennAir Professional appliances, and a walk-in pantry. More than fifteen slabs of quartz were incorporated throughout the kitchen and bedroom suites, creating a consistent level of finish throughout the home. Smart-home features, remote-controlled shades, custom lighting, elevator access, and thoughtfully curated finishes contribute to a comfortable and efficient living environment. A newly installed dock and Golden boat lift accommodate larger vessels, while recent dredging improves canal access for serious boaters. A pool package is in permitting, allowing the next owner to create a custom outdoor living space without navigating the island's permitting process from the beginning. The primary suite offers a private retreat with a custom-built walk-in closet and a spa-inspired bath featuring Toto fixtures, dual vanities, and multi-function shower features. Additional upgrades include dual high-efficiency HVAC systems, buried gas storage, generator readiness, tankless water heaters, and water-softening systems. Combining modern coastal architecture, deep-water boating access, Gulf views, updated construction, and one of the most walkable beach locations on Anna Maria Island, this Holmes Beach waterfront residence represents a rare opportunity within Florida's luxury coastal market. Easy access to North bridge/Manatee Ave via two different routes. Note: Pool is AI generated and is not present on the property, however permit is in final stages and pool is included in the price.
Listing is courtesy of: COLDWELL BANKER REALTY (813-286-6563)
Listing Agent: Jennifer Zales (813-758-3443)
120 52ND ST, HOLMES BEACH, FL 34217
$760,00023 Days on yellowkey MLS ID: A4693940
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1050 Built: 1973 Tax: $6,442 (2025)Community: Not ApplicableHalf Duplex
Taxes:$6,442
Remarks: Short Sale. Live a life you don't need a vacation from in this beautifully updated, turnkey-furnished beach villa just STEPS from the sugar-sand beaches of the Gulf. Located on the desirable west side of Holmes Beach, this charming 2-bedroom, 1.5-bath townhouse offers approximately 1,050 sq ft of coastal living with no major roads to cross on your way to the beach. Recently renovated, this home features a stunning new kitchen completed in 2025 with custom cabinetry, granite countertops, and state-of-the-art stainless-steel appliances. Fresh interior paint, new tile flooring throughout, and hardwood stairs create a clean, modern feel with no carpeting to maintain. Additional updates include a NEW ROOF IN 2024 & an A/C SYSTEM INSTALLED IN 2020. Enjoy your morning coffee in the inviting front seating area or unwind in the private fenced courtyard, perfect for grilling, entertaining, or relaxing after a day at the beach. With no condo fees, excellent rental potential, and a prime location just moments from shopping, dining, and everything Holmes Beach has to offer, this property presents an exceptional opportunity as a vacation getaway, investment property, or year-round residence. *** SELLER offering $10,000 credit towards closing costs on an agreed upon contract.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Christine Spelman (941-713-3501)
105 49TH ST, HOLMES BEACH, FL 34217
$3,490,000119 Days on yellowkey MLS ID: A4683981
REDUCED by $260,000 (6.9%) on 05/20/2026
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2999 Built: 1940 Tax: $41,424 (2024)Community: JonesSingle Family
Taxes:$41,424
Tax Year: 2024
Remarks: Beachfront Bliss – Gulf Views from Every Angle! Just one house from the beach, this 4-bedroom, 4-bath coastal stunner delivers postcard-perfect Gulf views straight from the kitchen sink—yes, you’ll actually smile while scrubbing plates! Natural light throughout, high ceilings, 2 sided fireplace, wet bar in the living room, open living area that flows into a chef’s kitchen. Stainless steel appliances, gas stove, double ovens and more! The coastal chic blue countertops and tile throughout for easy beach sand clean up! Step outside to your wrap around balcony to dine and enjoy the gulf breeze. Backyard features your private heated pool that includes a sun shelf. All the bedrooms are spacious and have their own privacy. The primary suite is upstairs with even better views of the Gulf to wake up to. Enjoy your private balcony AND a spiral staircase leading up to the roof top deck, ideal to watch sunsets and dolphins jump in the water. Master bathroom has a huge walk-in shower, soak in tub, dual sinks and a large walk-in closet that includes a safe. The location is central to the island, close to everything and very convenient. 30 day minimum rental period. One house away from the Gulf, this may be the island’s best-kept secret!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jason Sato (941-778-7200)
8321 MARINA DR, HOLMES BEACH, FL 34217
$4,295,000113 Days on yellowkey MLS ID: A4685020
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2775 Built: 1974 Tax: $23,777 (2024)Community: Holmes Beach 34Th Unit RepSingle Family
Taxes:$23,777
Remarks: One or more photo(s) has been virtually staged. Spectacular Waterfront Key West-Style Home on Bimini Bay!! This beautifully maintained 4 bedroom, 3 bathroom single-family home, offering 2,775 sq ft of living space on a spacious 9,400 sq ft lot. Meticulously crafted with thoughtful architecture, interiors and landscaping by legendary award-winning architect, Emily Anne Smith. As you step in, you’ll notice the double height ceilings, unique, blue glass chandelier in the entry that leads into the spacious open floor plan. Large slider impact doors that create natural light and provide stunning views of Bimini bay. The living room is warmed by a modern linear fireplace complemented by a wall of custom illuminated floating shelves and built-in cabinetry with an exquisite backlit blue agate Antolini countertop. A chef's dream, the kitchen is equipped with Monogram Professional Series appliances, quartz countertops and a thoughtful layout. Abutting the kitchen is the large laundry room leading to an oversized two car garage. A first floor primary suite has privacy and features an oversized en suite bathroom with double marble vanity. In addition, the first floor has a full bathroom with a frameless glass shower, custom blue glass waterfall sink and two generously sized bedrooms. The entire second level luxurious main suite features breathtaking water views, cathedral ceilings, dual custom walk-in closets, a large spa-like bathroom with a freestanding jetted tub surrounded by backlit quarzite counters, Bisazza tile, modern crystal chandelier, dual Carrara marble vanities, and spacious modern reclaimed wood porcelain tile walk-in shower. An expansive rooftop terrace and gazebo, not to be missed, offers a stunning 360-degree view of Anna Maria Island. Step outside to entertain on the expansive pool deck with a large pool, or retreat to the private upper deck for quiet sunsets and bay breezes. Resort style outdoor area includes an outdoor kitchen and bar, outdoor shower, covered fishing station, dual lift and dock area for jet skis and ample space to accommodate a large yacht, fishing or sport boat, making indoor/outdoor living and entertaining flawless. Brand new Interior and exterior paint throughout! Enjoy deep-water frontage with no bridges to the Gulf of Mexico and your own 9,000 lb boat lift — perfect for boating enthusiasts who want effortless Gulf access and quick runs to the open water. The home is just a short golf cart ride gorgeous sand beaches, making it ideal for beach lovers, families, or those seeking the ultimate Florida island lifestyle.
633 KEY ROYALE DR, HOLMES BEACH, FL 34217
$3,350,00065 Days on yellowkey MLS ID: A4690877
REDUCED by $145,000 (4.1%) on 06/02/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1910 Built: 1968 Tax: $15,831 (2025)Community: Key Royale 8Th AddSingle Family
Taxes:$15,831
Remarks: FULL INTERCOASTAL WATER VIEWS!!! A rare waterfront opportunity awaits on beautiful Anna Maria Island. Set on an oversized homesite along Key Royale Drive, this exceptional property offers the perfect canvas to build your island dream home. The backyard is a tranquil retreat offering world-class sunrise views over the intercoastal waterway, along with direct fishing and boating access to the Gulf. Just down the street, the Key Royale Club features a private 9-hole golf course, dining, and social amenities. You’re also only a short golf cart ride away from Anna Maria Island’s top-rated restaurants, boutique shopping, and pristine white-sand beaches. The existing 3-bedroom, 3-bathroom home sustained water damage from Hurricane Helene and has been partially gutted, providing a clean slate for redevelopment. The spacious backyard already includes a sparkling pool, private dock, and room to add a boat lift — an ideal foundation for waterfront living. Whether you’re seeking a full-time residence, luxury vacation home, or investment property, the possibilities here are endless!
749 MANATEE AVE #749, HOLMES BEACH, FL 34217
$650,00046 Days on yellowkey MLS ID: A4690595
REDUCED by $39,900 (5.8%) on 05/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1977 Tax: $5,437 (2024)Community: Westbay Cove SouthCondo
Taxes:$5,437
Remarks: JAW-DROPPING WATER VIEWS! Located on one of the highest sea level slices of land on the island. Revel & Relax as you experience amazing water views. Prepare to be enthralled by the mesmerizing beauty of the sparkling waters of Sarasota Bay, teaming with playful dolphins, graceful manatees, and the colorful spectacle of Florida's native birds. Witness spectacular sunrises, behold the magnificent moon while casting its illuminating reflection upon Sarasota Bay, all from this incredible place. This building sits on one of the highest points on the island. We are on the water with an incredible water view and we didn't get damaged (unlike our close communities) THIS IS HUGE Excellent investment. NON-OBSTRUCTED view in this Waterfront condo. You won't find a better view around this price. Enjoy spectacular sunrises and sunsets from every room. Sit on the Lanai and watch the yachts as they await the Manatee Bridge to lift so they can go under, this is a beautiful site as they cruise the blue waters. This beautifully remodeled condo on the bay is one of the few dog friendly communities. So many big ticket $$$$$$ items are newer inclusive of the HVAC, roof, Hurricane rated sliders and windows, hot water heater, stackable LG full capacity Laundry, duct work, baseboard and cove moulding throughout. The doors and all trim work has been upgraded to solid wood. There is new high end lighting, renewed electric and plumbing, and the list goes on. Popcorn ceilings gone!!! This is great considering the post hurricane prices now to renovate. WALK to the beach, dining, nightlife, grocery, drug store, liquor store and more. Are you a bird watcher? If so you will love the birds you view all day as they fly close to you coming to and fro from nearby Robinson Preserve. One of the nicest things about this place is you don't get stuck during season in all the traffic on the island and its easy to get off to the main land without the long wait that the owners on the north end or south end have. Community has a kayak launch and pickleball as well as tennis and a large heated pool with views of the water.
Listing is courtesy of: COASTAL KEY REALTY LLC (941-993-9380)
Listing Agent: Amy Jones (941-993-9380)
531 72ND ST, HOLMES BEACH, FL 34217
$4,500,000105 Days on yellowkey MLS ID: A4685680
5 Days Off yellowkey (back on 6/2/2026)
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: Under contract-accepting backup offers. 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Dee Munn (407-346-4422)
215 82ND ST, HOLMES BEACH, FL 34217
$3,900,00025 Days on yellowkey MLS ID: A4695448
Bed: 4 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 2686 Built: 2027 Tax: $9,268 (2025)Community: Holmes Beach 31St Unit AmdSpa: YesSingle Family
Taxes:$9,268
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, this exceptional new coastal residence offers a rare opportunity to own luxury new construction in the heart of Holmes Beach, just moments from the sugar-white sands and turquoise waters of Anna Maria Island. Thoughtfully designed to embrace the island lifestyle, this custom home will feature expansive open-concept living spaces, soaring ceilings, designer finishes, and seamless indoor-outdoor living throughout. Multiple guest suites with private ensuite baths provide comfort and privacy for family and visitors, while the primary suite serves as a luxurious retreat complete with a spa-inspired bathroom, oversized walk-in closet, and private access to outdoor living spaces. Designed for both convenience and luxury, the residence will include a private elevator providing easy access to all levels of the home. Covered lanais, a resort-style pool and spa, and a dedicated pool bath create the ideal setting for effortless indoor-outdoor living and entertaining. Generous gathering spaces allow family and guests to enjoy the Florida lifestyle year-round, while the rooftop observation deck provides a spectacular venue for sunset views, coastal breezes, and panoramic island vistas. At the heart of the home, the chef's kitchen is planned to feature custom cabinetry, premium countertops, upscale appliances, a large center island, and effortless flow into the living and dining areas, creating an ideal environment for entertaining and everyday living. Whether utilized as a primary residence, seasonal retreat, or investment property, this home offers exceptional versatility in one of Florida's most desirable beach communities. Holmes Beach continues to attract visitors and homeowners alike with its pristine beaches, boating opportunities, waterfront dining, boutique shopping, and relaxed coastal charm. Ideally located near Gulf beaches, marinas, restaurants, and local attractions, this property provides convenient access to everything Anna Maria Island has to offer. Built to current FEMA-compliant flood elevation requirements and the latest coastal construction standards, the residence is designed to deliver enhanced storm resiliency, modern efficiency, and peace of mind while maintaining the luxury finishes and craftsmanship expected from a Noah Thomas Builders home. Secure this opportunity early and experience the elevated coastal lifestyle, exceptional attention to detail, and quality construction. Finishes, materials, specifications, pricing, and availability are subject to change during the construction process and prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
227 S HARBOR DR, HOLMES BEACH, FL 34217
$3,400,000108 Days on yellowkey MLS ID: A4684262
REDUCED by $100,000 (2.9%) on 06/01/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3274 Built: 2023 Tax: $45,830 (2024)Community: Sportsmans Harbor RevSingle Family
Taxes:$45,830
Remarks: Experience elevated coastal living in this brand-new, designer-finished 4BR/4.5BA luxury home located just a 5-minute walk to the pristine beaches of Anna Maria Island. Thoughtfully crafted with high-end finishes and a bright, open-concept layout, this residence blends modern elegance with relaxed island charm. Currently utilized as a successful short term vacation rental with proven rental revenue. 4 spacious ensuite bedrooms, including three king suites with walk-in showers Gorgeous open living area with abundant natural light and upscale coastal décor Chef’s kitchen featuring modern cabinetry, stone counters, and stainless appliances Private heated pool with in-ground spa, surrounded by lush tropical landscaping Expansive rooftop deck offering panoramic views and unforgettable sunsets Fully furnished with professionally curated interiors Designed for relaxation and entertaining, the outdoor oasis includes a sparkling pool, spa, covered lounging areas, multiple decks including a rooftop deck ideal for sunrise coffee or sunset cocktails. The fenced yard provides privacy while maintaining a breezy, coastal feel. Situated in the heart of Holmes Beach, this home offers walkable access to sugar-sand beaches, local dining, boutiques, and the island’s free trolley. Enjoy the perfect blend of tranquility and convenience in one of Florida’s most desirable beach communities. This unique property can be utilized as primary residence, second home, or high-performing vacation rental investment property. This property delivers luxury, comfort, and strong rental appeal in a premier island location.
Listing is courtesy of: LESLIE WELLS REALTY, INC. (941-776-5571)
Listing Agent: Leslie Wells (941-776-5571)
305 55TH ST, HOLMES BEACH, FL 34217
$4,295,000218 Days on yellowkey MLS ID: A4672370
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3010 Built: 2024 Tax: $6,834 (2024)Community: Holmes Beach 11Th UnitSingle Family
Taxes:$6,834
Remarks: Welcome to "Black Pearl"! Discover refined island living in this exceptional 2024 custom-built residence, ideally situated just 1.5 blocks from the pristine Gulf beaches. Designed with sophistication and comfort in mind, this 4-bedroom, 4-bath elevated home offers a seamless blend of modern elegance and coastal charm. The light-filled great room showcases designer furnishings, premium finishes, and expansive living and dining spaces. The gourmet kitchen is a true showpiece, featuring quartz countertops, custom wood cabinetry, Dacor high end appliances, large island and wet bar with ice maker just off the dining room. Four spacious bedrooms and bathrooms provide privacy and luxury for residents and guests alike. An elevator services every level from the outside pool area all the way up to the roof top deck complete with firepit, enhancing ease of living. Step outside to your private resort-style sanctuary complete with a heated pool, spa, and lush tropical landscaping with turf. Multiple covered balconies and outdoor living areas create inviting spaces for relaxation or elevated entertaining. Offered fully furnished, this residence embodies turnkey luxury on Anna Maria Island. A rare opportunity to own a newly constructed coastal retreat in one of Holmes Beach’s most desirable locations on a dead end street. The home is barely lived in and is just being started as a weekly rental the end of November which will become a superb investment property or make it your very own. Do not miss out on this amazing property! Schedule your showing today!
5608 GULF DR #114, HOLMES BEACH, FL 34217
$1,090,000155 Days on yellowkey MLS ID: A4679026
2 Days Off yellowkey (back on 5/31/2026)
REDUCED by $100,000 (8.4%) on 05/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1236 Built: 1981Monthly Fee: $1,150 Tax: $6,403 (2024)Community: Sun Plaza WestSpa: NoCondo
Taxes:$6,403
Remarks: Under contract-accepting backup offers. Wake up to sweeping views of the Gulf of Mexico from this beautifully maintained two-bedroom, two-bath condo in Sun Plaza West. I direct Gulf front complex on Anna Maria Island. Filled with natural light, this home offers comfortable and inviting coastal living, featuring ceramic tile flooring throughout, Cambria granite countertops, Jen-Air appliances, PGT impact windows, and Hunter Douglas blinds that enhance both style and function. Thoughtfully placed dimmer switches create a warm, customizable ambiance, while beautiful Gulf views can be enjoyed year-round from the living spaces and bedrooms. The condo comes fully furnished, making it truly move-in ready and ideal for immediate enjoyment or rental use. Enjoy coffee in the morning off the cozy balcony off the master or enjoy happy hour on the amazing beaches of the Anna Maria. The home was completely renovated recently, offering all new electrical and plumbing throughout. Enjoy the ease of laundry inside the home for easy cleaning, as well as updated finishes and a well-designed layout that balances comfort and functionality. Recent upgrades provide added peace of mind, including a brand-new air conditioning system installed in 2023 and a new hot water heater in 2024. Residents enjoy a variety of desirable community amenities, including a sparkling pool, tennis court, and pickleball court—perfect for both relaxation and an active lifestyle. A private 8x10 storage unit, offering ample space for beach gear, bikes, or seasonal items. Whether you’re seeking a full-time residence, a vacation retreat, or an investment opportunity, this Gulf-view condo offers an exceptional combination of comfort, quality finishes, thoughtful updates, and coastal scenery in a sought-after setting. This is the perfect home for living the Anna Maria Life!
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)
Listing Agent: Billi Gartman (941-545-8877)
15 SEASIDE CT, HOLMES BEACH, FL 34217
$599,000477 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
$599,000578 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
Tax Year: 2023
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.
6300 FLOTILLA DR #105, HOLMES BEACH, FL 34217
$410,000258 Days on yellowkey MLS ID: A4668176
4 Days Off yellowkey (back on 5/29/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1023 Built: 1976 Tax: $2,174 (2024)Community: Shell Point Unit IvCondo
Taxes:$2,174
Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT! Watch dolphins play in Watson's Bayou. Soak up your spectacular bay views in a private setting with all the amenities - tennis/pickleball court, heated swimming pool, putting green, clubhouse, waterfront park, and shuffleboard. This NEWLY RENOVATED GROUND FLOOR unit has luxury vinyl plank flooring throughout, new kitchen, appliances, and new baths, as well as fresh paint…all ready for your furniture and finishing touch. The utility/craft room has served as an art studio for the past two owners, or you can add a washer and dryer according to your preference. Close to restaurants and the beach for an amazing seasonal or year-round experience. Come see the view!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Stephen Arters (941-876-8886)
5200 GULF DR #107, HOLMES BEACH, FL 34217
$699,999149 Days on yellowkey MLS ID: A4680141
REDUCED by $69,001 (9.0%) on 05/29/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1057 Built: 1970 Tax: $8,534 (2024)Community: Martinique Apts SouthCondo
Taxes:$8,534
Remarks: Wake up to salt air and sunset skies in this 2 bedroom, 2 bath beachfront condo on the sugar-white sands of Anna Maria/Holmes Beach. Perfectly positioned on the Gulf, this coastal retreat offers effortless island living with direct beach access just steps from your door. Inside, the light-filled layout features an open living and dining area, well-appointed kitchen, and spacious bedrooms designed for comfort after a day in the sun. Not to mention this unit comes with THREE storage units AND a private garage (STORAGE AREAS #45, 46, & 47 AND GARAGE #38). Enjoy morning coffee with Gulf breezes, evening walks along the shoreline, and year-round sunsets that never get old. Whether you’re searching for a full-time residence, a vacation getaway, or an investment opportunity, this condo places you in the heart of one of Florida’s most beloved barrier islands—close to charming shops, local dining, and the laid-back lifestyle Anna Maria Island is known for. Beach life doesn’t get better than this.
Listing Agent: Ryan Sheck (863-581-4005)
727 KEY ROYALE DR, HOLMES BEACH, FL 34217
$3,750,00029 Days on yellowkey MLS ID: TB8512426
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3640 Built: 1988Monthly Fee: $150 Tax: $46,302 (2025)Community: North Point Harbour Unit ThreeSingle Family
Taxes:$46,302
Remarks: Experience elevated coastal living in the exclusive North Point Harbor community of Holmes Beach, located on the highly desirable northern end of Anna Maria Island. This impeccably maintained custom waterfront estate spans approximately 3,640 square feet and offers direct deep-water access to both the Gulf of Mexico and Tampa Bay from the peaceful shores of Key Royale. Designed with both luxury and functionality in mind, the home features 5 bedrooms, a versatile bonus room, and 6 bathrooms (4 full and 2 half), showcasing timeless craftsmanship and a spacious, thoughtfully designed layout. Built for lasting quality and refined coastal style, the residence features a durable metal roof, elegant vinyl wood and tile flooring throughout the open living spaces, and two expansive balconies perfectly positioned to capture stunning panoramic water views from nearly every angle. Seller financing may be available, subject to terms. For boating enthusiasts, the private dock and dedicated boat slip offer effortless, no-bridge access to open Gulf waters and the renowned fishing grounds surrounding Egmont Key — ideal for accommodating a yacht or sportfishing vessel. Beyond the home itself, enjoy the unmatched lifestyle of Anna Maria Island, celebrated for its charming “Old Florida” atmosphere and strict building limitations that preserve breathtaking views and laid-back island character. This golf-cart-friendly community offers easy access to pristine Gulf beaches, boutique shopping, and exceptional dining along Pine Avenue and Gulf Drive. Key Royale is especially sought after for its quiet, tucked-away setting, private golf club, and serene waterfront surroundings, while North Point Harbor residents also enjoy beautifully maintained grounds and private tennis courts. Conveniently located just a short drive or boat ride from both Sarasota and St. Petersburg, this property offers the perfect balance of peaceful island living and access to vibrant cultural destinations. Meticulously cared for with no flood damage history, the home is truly move-in ready and maintained to exceptional standards. Whether entertaining from the chef-inspired kitchen, relaxing on the screened lanai overlooking the pool, or setting out for a sunset cruise from your private dock, this extraordinary property delivers the ultimate blend of coastal sophistication, resort-style comfort, and enduring quality. From its resilient construction to its artisan finishes, every detail has been carefully curated to create a premier waterfront retreat in one of Florida’s most coveted island destinations. Embrace the Anna Maria Island lifestyle — where every sunset feels unforgettable and the water is always just steps away.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Robert Johnson (813-364-2250)
512 67TH ST, HOLMES BEACH, FL 34217
$1,850,00042 Days on yellowkey MLS ID: A4693792
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1737 Built: 1972 Tax: $18,412 (2025)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$18,412
Remarks: This oversized lot features an expansive seawall, a brand-new dock, and a 16,000-pound boat lift, offering endless possibilities to build your custom dream home or renovate the existing residence to fit your lifestyle. Enjoy the outdoor Florida lifestyle with a large built-in pool and spa, complete with a new heater. Situated on one of the widest canals in Holmes Beach, this property provides easy boating access through Bimini Bay and directly out to the open waters of the Bay. A rare waterfront gem that truly must be seen to be appreciated!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Charles Buky (941-228-6086)
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