Location: Holmes Beach
Do Not Show Listings
306 66TH ST, HOLMES BEACH, FL 34217
$1,475,000155 Days on yellowkey MLS ID: A4678590
REDUCED by $75,000 (4.8%) on 06/09/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1502 Built: 1962 Tax: $15,256 (2024)Community: Key Royale TerraceSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$15,256
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Welcome to LivinGood, a thoughtfully redesigned beach home where effortless indoor-outdoor living shines. Slide open the glass doors and step directly into your private pool and entertainment area, keeping family and guests seamlessly connected without the need to climb a single set of stairs. This completely remodeled 3-bedroom, 2-bath pool home is offered turnkey furnished and blends modern luxury with laid-back beachside charm, with beach access just minutes away. Inside, impeccable craftsmanship is highlighted by restored terrazzo floors, a gourmet kitchen with quartz countertops, all-wood custom cabinetry, and a high-end gas range, a split floor plan for added privacy, and fully updated bathrooms with modern finishes. The home is equipped with a tankless water heater, two mini-split units, a top-of-the-line Trane A/C system, and an EV charger for comfort and efficiency. Outdoors, enjoy a custom high-end pool built by one of the top pool builders on AMI, a screened-in lanai, lush low-maintenance turf, a putting green, built-in closets, ample storage, and close proximity to the island’s best dining and shopping. Everything has been thoughtfully designed with the end user in mind. Schedule your private showing today!
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Joey Hutchinson (941-518-5585)
525 68TH ST, HOLMES BEACH, FL 34217
$6,145,000224 Days on yellowkey MLS ID: A4671356
REDUCED by $5,000 (0.1%) on 06/02/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3574 Built: 2025 Tax: $11,692 (2024)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$11,692
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
Remarks: Just Completed Coastal Southern Retreat on the Grand Canal! Welcome to 525 68th Street, an elegant newly completed Southern-style residence perfectly positioned along the coveted Grand Canal in Holmes Beach. This 4-bedroom, 4.5-bath masterpiece offers timeless charm blended with modern coastal luxury. Each spacious en suite bedroom exudes comfort and style, while a private study provides the perfect quiet escape. The open-concept chef’s kitchen is designed for entertaining, featuring premium appliances, custom cabinetry, and designer finishes. An elevator connects all levels, leading to expansive porches and a stunning rooftop deck with panoramic views of Tampa Bay and the Gulf of Mexico—ideal for sunset gatherings or morning coffee. Step outside to your private oasis—lush tropical landscaping surrounds a heated pool and spa, creating a serene setting for relaxation or waterfront entertaining. With some of the best boating water on Anna Maria Island and quick access to the Intracoastal and Gulf, this property is a boater’s dream. Beautifully designer-furnished and move-in ready, this home invites you to enjoy island living at its finest—just moments from the charming shops, restaurants, and sugar-sand beaches of Holmes Beach. Spend your holidays in pure coastal elegance!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Charles Buky (941-228-6086)
302 67TH ST, HOLMES BEACH, FL 34217
$1,399,900195 Days on yellowkey MLS ID: A4674440
REDUCED by $50,100 (3.5%) on 05/27/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1552 Built: 1960 Tax: $6,504 (2025)Community: 67Th Coastal Cottages Or2448/1887Spa: NoSingle Family
Taxes:$6,504
Tax Year: 2025
Remarks: The fabulously updated kitchen and open floor plan, make this 3 bedroom/2 bath half duplex a picture perfect island escape. Ideally situated on a quiet corner lot in the heart of the island, it is a straight walk down the street to the sugar sand beach, making it a popular vacation rental too! The split bedroom plan is perfect for hosting, and the updated, private, heated pool and trellis invite you to step out your wall of sliders and enjoy the Florida sunshine. You will love 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. Step out for a dip in the pool from your large primary en suite with high ceilings, and a bathroom with dual vanity and a walk in shower. Your spacious guest rooms on the other side of the house, 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 home!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Erin Leathem (941-448-5616)
8010 MARINA DR, HOLMES BEACH, FL 34217
$1,095,000151 Days on yellowkey MLS ID: A4678584
1 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1469 Built: 1957 Tax: $15,450 (2024)Community: Holmes Beach 30Th UnitSingle Family
Taxes:$15,450
Remarks: Renovation-Ready asset + Dock! Seize the opportunity to create something truly special on Anna Maria Island. Located on an oversized 9,282 sq ft corner lot, this 3-bedroom, 3-bath residence offers rare flexibility and exceptional upside in one of Florida’s most desirable coastal markets. Currently featuring 1,868 square feet under roof, the home presents a blank canvas ready to be reimagined as your custom island retreat. Zoned for duplex use, the property opens the door to multiple possibilities—whether a full renovation, new construction, or income-producing strategy. Highlights include- Deeded dock (needing some clean-up work), located across the street. Existing pool and pool deck, ideal for year-round island living One-car garage plus carport for convenience and storage Private backyard, perfect for entertaining or quiet relaxation Previously utilized as a 7-night rental with a strong rental history The property was impacted by Hurricane Helene and is being offered AS IS. It has been thoroughly cleaned out and is ready for its next chapter—whether restored or completely re-envisioned. This is a rare chance to secure a generously sized corner lot with zoning flexibility on Anna Maria Island. Bring your vision, contractor, or architect and make it your own. Contact me today for details or to schedule a private showing.
Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)
Listing Agent: Shauna Ruby (941-544-2070)
403 75TH ST, HOLMES BEACH, FL 34217
$2,395,000414 Days on yellowkey MLS ID: A4650766
REDUCED by $90,000 (3.6%) on 06/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1900 Built: 1955 Tax: $17,404 (2024)Community: Bay Palms Add Fourth UnitSpa: YesSingle Family
Taxes:$17,404
Remarks: Charming Coastal Cottage in Holmes Beach. Welcome to this newly and meticulously remodeled coastal retreat, ideally located in the heart of Holmes Beach. This one-of-a-kind, artsy beach cottage blends timeless charm with modern elegance and smart technology. Step through the inviting rain glass double doors into a spacious open-concept living, dining, and kitchen area, where a dramatic lighted cupola and vaulted ceilings create a stunning first impression. A custom shell stone fireplace with a wood mantle adds warmth to the cozy seating area—perfect for relaxing or entertaining. The chef’s kitchen is a true showstopper, featuring an oversized, lighted quartz island with seating, beadboard cabinetry, and a custom wave-patterned glass backsplash. High-end appliances include an ILVE Majestic 4-burner gas stove with griddle, GE Café refrigerator, wine fridge, and porcelain farm sink—all designed with entertaining in mind.Craftsmanship continues throughout with custom millwork, shiplap accents, paneled walls, and solid-core doors. Oversized sliding glass doors open to reveal a tropical backyard oasis, complete with a free-form heated pool and spa, paver patio with artificial turf. The lush, mature landscaping with up lighting show off the tall palm trees, perfect for a evening cocktail party under the stars. The southern-facing yard is perfect for dining, lounging, and soaking up the sun. Each of the three bedrooms and 2.5 baths showcases custom chrome period fixtures, retro-inspired sinks, and designer details. Tech-savvy buyers will love the smart home features, including Lutron lighting controls, LED lighting, Sonos sound system, security cameras, and plantation shutters. The property includes a 250-gallon buried propane tank serving the on-demand water heater, gas grill, pool heater, and stove. It’s also generator-ready with existing plumbing and wiring in place. There is city dockage close by for boating enthusiast's This extraordinary home offers a rare blend of beachy charm and premium amenities including a "She Shed" which offers additional luxurious living space. Words cannot describe the uniqueness of this feature so call now for your private showing of this amazing property.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Gregg Bayer (941-799-9096)
2913 GULF DR, HOLMES BEACH, FL 34217
$999,00097 Days on yellowkey MLS ID: A4684724
REDUCED by $50,000 (4.8%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1048 Built: 1940 Tax: $13,580 (2024)Community: IlexhurstSingle Family
Taxes:$13,580
Remarks: You must see this charming 1940s Craftsman cottage tucked into the historic heart of Anna Maria Island! This beautifully renovated two-bedroom, two-bath homestead blends timeless Old Florida character with effortless coastal charm. The home’s distinctive pecky pine exterior pay homage to its heritage while creating a warm, inviting island aesthetic that reflects the relaxed spirit of Anna Maria’s historic beach community. Inside, the home opens into a light-filled open floor plan designed for easy coastal living and effortless entertaining. The living, dining, and kitchen areas flow seamlessly together, creating a welcoming gathering space filled with natural light and breezy island ambiance. Whether enjoying a quiet morning coffee or hosting friends after a day at Anna Maria’s beautiful beaches, the layout makes the home feel both spacious and intimate. A convenient indoor laundry room is thoughtfully tucked away, adding modern practicality to this historic retreat. The home features a well-designed split floor plan, offering privacy and comfort for residents and guests alike. The primary bedroom suite includes a private ensuite bath, creating a peaceful retreat at the end of the day. On the opposite side of the home, the second bedroom features charming built-in bunks, perfect for family or visiting guests, with easy access to the second full bath. Step outside to discover a beautifully landscaped private pool enclosure, surrounded by lush tropical greenery that creates a tranquil island oasis. It’s the perfect spot to relax, unwind, and soak in the peaceful rhythm of Anna Maria’s laid-back island lifestyle. All of this is located just two blocks from Anna Maria’s world-famous sugar-sand beaches, and only moments from the island’s beloved restaurants, charming boutiques, and local shops. Spend your days biking to breakfast cafés, strolling to dinner with sunset views, or exploring the unique coastal storefronts that make Anna Maria so special. This lovingly restored cottage offers a rare opportunity to own a piece of historic island charm paired with modern comfort in one of Florida’s most treasured beach communities.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Becky Sirigotis (941-201-8000)
504 69TH ST, HOLMES BEACH, FL 34217
$1,295,00070 Days on yellowkey MLS ID: A4688938
REDUCED by $30,000 (2.3%) on 06/03/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1960 Built: 1968 Tax: $13,415 (2025)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$13,415
Remarks: This newly remodeled open floor plan Anna Maria Island Hideaway is nestled in the heart of the island in Holmes Beach just off of Marina Drive. Just 4 blocks to the award winning white sandy beaches of Anna Maria. With this home you will enjoy a comparatively large and spacious floor plan and a “old Florida” feel of the quiet neighborhood along with the benefit of the totally private back yard and gorgeous marina water views from the front. This home has large hurricane-rated windows with Levolor Custom Sheer Shade window coverings, new ceramic tile flooring throughout, a beautifully revamped kitchen with new GE stainless steel appliances, a separate indoor laundry room with new GE large capacity front load washer/dryer and plenty of additional cupboard storage, and newly tiled spa-like bathrooms. Comfort is assured at all times with a brand-new Carrier A/C with heat pump and smart home thermostat and a tankless water heater for never-ending hot showers. The backyard is a private tropical oasis featuring an updated and heated saltwater pool with new pump, pool heater and salt chlorinator, a top of the line 2022 HotSprings Vanguard saltwater hot tub, lush irrigated and lighted landscaping, a 6ft privacy fence surround, and a massive fan cooled and lighted tiki-covered paver patio for outdoor TV and entertaining. The home exterior has updated HardiePlank siding, a 2019 roof, and beautifully landscaped yard along with the marina canal views right across the street. Just a short 4 block walk to the Gulf beaches and close to everything that makes Anna Maria Island great: top restaurants and pubs, free Island Trolley, boutiques, and all the beach and cart-riding fun you can handle to provide the ultimate island living experience. Finally, and very importantly, this home has no HOA, no Master Association, no CDD fees, and can be (is currently) Homesteaded to keep property taxes manageable.
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
529 77TH ST, HOLMES BEACH, FL 34217
$5,695,000129 Days on yellowkey MLS ID: A4680377
REDUCED by $100,000 (1.7%) on 05/07/2026
Bed: 5 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 5300 Built: 2012 Tax: $68,935 (2024)Community: Holmes Beach 31St Unit AmdSpa: YesSingle Family
Taxes:$68,935
Remarks: Discover the epitome of coastal sophistication with this exquisite British West Indies waterfront residence, perfectly nestled on Anna Maria Island. Spanning over 5,000 square feet, this luxurious home is designed for those who love to entertain and indulge in the finer things in life. Step inside to find two lavish primary suites, an elevator, and multiple terraces that offer breathtaking views. The entertainment options are endless with a stylish media room featuring a beverage center, ideal for movie nights or hosting friends. Every corner of this home exudes elegance, from the solid wood cabinetry and custom millwork to the stunning hardwood and travertine flooring. The open floor plan seamlessly connects to an eat-in kitchen, boasting a large central island, double oven, butler’s pantry, and granite surfaces, making it a chef’s paradise. For more formal gatherings, the separate dining room sets the perfect scene. An office or den is conveniently located on the main level, offering a quiet retreat for work or relaxation. Two additional bedrooms share a spacious bathroom complete with a walk-in shower, ensuring comfort for family or guests. Outdoors, the multiple living areas provide serene views of the canal and Bimini Bay, with direct access to the Intracoastal waterway. The lavish outdoor amenities include a saltwater pool with a sun shelf and spa, and a 70-foot dock equipped with a 13,000-pound boat lift, perfect for boating enthusiasts. Entertain in style on the expansive covered lanai, featuring an outdoor kitchen and ample space for gatherings. Additional features such as plantation shutters, a state-of-the-art security system, oversized closets, and a 3-plus car garage enhance the allure of this property. Don’t miss your chance to own this stunning waterfront retreat. Call today for your private viewing and step into a lifestyle of unparalleled luxury.
634 KEY ROYALE DR, HOLMES BEACH, FL 34217
$2,999,999117 Days on yellowkey MLS ID: A4683541
REDUCED by $175,001 (5.5%) on 05/04/2026
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. The property is also equipped with a private artesian well for irrigation, providing a reliable and cost-efficient water source to maintain the lush tropical landscaping while helping reduce monthly utility costs. 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. Recently reduced in price, this waterfront property presents an exceptional opportunity for buyers looking to enjoy the best of Anna Maria Island with minimal upkeep, immediate boating access, and long-term value in one of the island’s premier neighborhoods.
Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC (941-224-3304)
Listing Agent: Jason Hrnak (941-773-6572)
6401 MARINA DR, HOLMES BEACH, FL 34217
$2,390,00030 Days on yellowkey MLS ID: A4693685
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2031 Built: 1973Monthly Fee: $150 Tax: $8,704 (2025)Community: Seaside Gardens RepSpa: YesSingle Family
Taxes:$8,704
Remarks: Welcome to an extraordinary waterfront retreat on beautiful Anna Maria Island featuring over 100 feet of deep-water canal frontage, private dockage, direct Gulf access with no bridges, and the rare advantage of weekly rentals allowed, making it an exceptional investment opportunity. Fully reimagined by Eason Builder Group, this stunning 3-bedroom, 3.5-bath coastal residence blends elevated luxury craftsmanship with effortless island living — offering exceptional boating access, resort-style outdoor spaces, walkability to the beach, and outstanding income-producing potential. From the moment you arrive, lush tropical landscaping and timeless coastal architecture create an immediate sense of relaxed sophistication. Inside, every detail has been thoughtfully curated with custom millwork, wood coffered ceilings, wide-plank flooring, designer lighting, layered textures, upscale furnishings, and beautifully integrated indoor-outdoor living spaces. The open-concept floor plan centers around a spectacular chef’s kitchen featuring premium appliances, quartz countertops, custom cabinetry, designer tilework, statement pendants, and a handcrafted wood-accent range hood. Each bedroom feels like a private boutique retreat, including a custom-designed bunk room ideal for hosting guests and maximizing luxury vacation rental appeal. Spa-inspired bathrooms showcase elevated tile selections, custom vanities, and refined coastal finishes throughout. Outside, the home transforms into a true private island resort with a spectacular pool and spa, expansive sun deck, tropical landscaping, multiple lounge areas, outdoor dining spaces, and a fully equipped summer kitchen designed for unforgettable entertaining. For boating enthusiasts, the private dock provides effortless access for boats, paddleboards, kayaks, and jet skis — perfect for exploring nearby sandbars, waterfront restaurants, and the turquoise Gulf waters. Located moments from Anna Maria Island’s famous white sand beaches, Pine Avenue boutiques, cafés, and waterfront dining, this exceptional furnished property is perfectly suited as a luxury primary residence, island getaway, or high-performing vacation rental investment offering the ultimate island lifestyle.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
203 N HARBOR DR, HOLMES BEACH, FL 34217
$3,175,000151 Days on yellowkey MLS ID: A4678835
REDUCED by $120,000 (3.6%) on 04/22/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2636 Built: 2011 Tax: $43,372 (2024)Community: Sportsmans Harbor RevSpa: YesSingle Family
Taxes:$43,372
Remarks: Your dream view, just got a dream price! Luxury 5 Bedroom Waterfront + Dock | 3-Min Walk to Beach -Exceptional waterfront retreat perfectly positioned in the heart of Anna Maria Island. Just a three-minute stroll to the soft sugar sands of Manatee Beach, this stunning five-bedroom, three-and-a-half-bath residence delivers coastal luxury at every turn—complete with a private dock with ladder where manatees often glide by, a heated pool and spa, and a show-stopping rooftop deck with Gulf and Bay views. Designed for unforgettable gatherings, Coral Castle seamlessly blends upscale comfort with relaxed island charm! Outdoor Living at Its Finest, the rooftop deck is the crown jewel of Coral Castle—offering breathtaking sunrise and sunset views over both the Gulf and Bay. Start your mornings with coffee and ocean breezes or unwind in the evening with a cocktail as the sky glows in brilliant island hues. The tropical backyard is a private sanctuary featuring a heated pool, spa, lounge seating, and outdoor grill, perfect for post-beach relaxation or entertaining under the stars. From the private dock, enjoy peaceful water views—and keep watch for friendly manatees passing by, an unforgettable hallmark of island living. Stylish Interiors Made for Comfort-Step inside to a bright, open-concept living space filled with natural light and coastal elegance. The living room offers plush seating, a flat-screen TV, and sliding glass doors that open directly to the outdoor patio—blurring the line between indoor and outdoor living. The chef-inspired kitchen is fully equipped with stainless steel appliances, generous counter space, and a wine fridge, making meal prep effortless. Gather inside at the dining table or dine alfresco beneath the covered patio for a true island experience. Sleep in Luxury- Primary Suite: King bed, private balcony, vaulted shiplap ceiling, walk-in closet, spa-style ensuite with soaking tub and walk-in shower; Second Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Third Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Fourth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo; and Fifth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo. Prime Island Location- Enjoy peaceful mornings fishing from the dock or take a short drive to Pine Avenue and Bridge Street, where you’ll discover charming boutiques, local dining, and island favorites. Whether your days are spent boating, lounging by the pool, or soaking in rooftop views, Coral Castle delivers the perfect balance of relaxation and adventure. Every detail is designed to create lasting memories—from manatee sightings to sunset cocktails on the rooftop. This is more than a stay—it’s a true Anna Maria Island experience. Currently operating as a vacation rental with solid history and a strong start to 2026—ideal personal-use + income opportunity.
204 75TH ST, HOLMES BEACH, FL 34217
$1,574,000210 Days on yellowkey MLS ID: A4672818
REDUCED by $25,000 (1.6%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1777 Built: 1953 Tax: $17,655 (2025)Community: Bay Palms AddSpa: NoSingle Family
Taxes:$17,655
Remarks: Fantastic Vacation Rental Loved By All Generations Welcome to the ultimate island vacation home. Located in a weekly rental zone, it is positioned to be an outstanding income producing property with strong vacation rental history and bookings secured into Summer 2026, making it an exceptional investment opportunity for any buyer. This fully renovated ground level retreat is designed for effortless living, easy accessibility, and unforgettable stays. Families and guests of all ages love the spacious layout and the simple walk to the beach. Just a quick two minute stroll to soft sand and nightly sunsets, this home delivers everything families want in a perfect Anna Maria Island getaway. Beautifully renovated in 2025 inside and out, this 3-bedroom, 2 bath home offers 1,777 square feet of fresh modern style on a generous 7,022 square foot lot. Every key system has been updated for comfort and peace of mind including new drywall, insulation, AC ductwork, water heater, high impact windows, and a 2023 metal roof. The new kitchen features stylish cabinetry and brand-new appliances. Both bathrooms have been refreshed with new vanities and finishes, and the home includes a new washer and dryer with custom laundry cabinetry. Step outside to your private oasis with a heated pool powered by a new pool heater, lush new landscaping, updated irrigation, and plenty of space to relax in the sun. The large garage is ideal for beach gear, bikes, a golf cart, or a fun game area for guests. The home is being sold fully turnkey furnished with all new furniture and décor so it is ready to drop your bags and enjoy from day one. This is a rare opportunity to own a fully updated, high performing, guest friendly vacation rental on Anna Maria Island. A home that generations can enjoy together. A home that renters will return to year after year. Your slice of paradise is ready. Don't wait, call for your private showing today and start enjoying island life.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Kathy Harman (941-900-9828)
618 GLADSTONE LN, HOLMES BEACH, FL 34217
$2,750,00031 Days on yellowkey MLS ID: A4694012
0 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2211 Built: 1972Monthly Fee: $8 Tax: $4,283 (2025)Community: Key Royale 15Th AddSingle Family
Taxes:$4,283
Remarks: Under contract-accepting backup offers. Experience the pinnacle of Anna Maira Island living in this stunning waterfront estate, situated in the highly sought-after boating and golf community of Key Royale. Freshly completed in 2026, this residence has undergone a meticulous, "to-the-studs" transformation. Offering the ultimate peace of mind, the property sits at a noticeably higher elevation than most homes on the island, features a brand-new metal roof, and is fully equipped with premium PGT windows and full hurricane impact-rated protection throughout. Offered furnished with designer-curated pieces, the expansive, light-filled open floor plan flows effortlessly across premium large-format tile flooring. At the heart of the home is a fully equipped kitchen, anchored by a massive island, custom cabinetry, a beautiful coastal-blue tile backsplash, and top-tier GE Café stainless steel appliances. An adjacent butler’s pantry, complete with an additional sink, ample storage, microwave, and a dedicated wine refrigerator, ensures effortless hosting. Accommodations include a highly flexible fourth bedroom, perfectly suited for a private home office, media room, or custom bunk room to maximize guest comfort. The interior spaces seamlessly transition to a spectacular backyard paradise through massive impact sliding glass doors. Positioned on one of the largest canals on Key Royale, this property is a boater’s dream, with an expansive private dock with direct, deep-water access. Designed for sunset entertaining, the expansive outdoor living space centers around a newly resurfaced PebbleTec pool, framed by elegant shellstone pavers and a large covered patio. The perfectly manicured grounds are framed by mature palm trees, professional exterior lighting, and a full irrigation system. Located just moments away from the exclusive Key Royale Club, offering the island’s premier private golf and social amenities, this fully updated masterpiece delivers coastal luxury.
529 67TH ST, HOLMES BEACH, FL 34217
$1,499,000134 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)
303 55TH ST, HOLMES BEACH, FL 34217
$4,375,000100 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
Taxes:$9,277
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
$2,650,00036 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
$1,075,000104 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
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!
201 N HARBOR DR, HOLMES BEACH, FL 34217
$4,500,00016 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)
105 49TH ST, HOLMES BEACH, FL 34217
$3,490,000112 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
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
$4,295,000106 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.
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