Displaying: For Sale
Location: Holmes Beach
Property Type(s): Single Family
Beds: 4 to 4
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Holmes Beach - 33 properties found
243 S HARBOR DR, HOLMES BEACH, FL 34217
$2,900,000113 Days on yellowkey MLS ID: A4684027
1 Days Off yellowkey (back on 6/23/2026)
REDUCED by $100,000 (3.3%) on 06/01/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2016 Built: 2024 Tax: $8,421 (2024)Community: Sportsmans Harbor RevSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,421
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. This almost brand-new, (2024) fully furnished 4-bedroom, 4.5-bath luxury residence delivers the perfect blend of island relaxation and modern sophistication. Built to the highest standards and unaffected by recent hurricanes, it offers peace of mind along with exceptional design. A charming front entry welcomes you into a bright, open great-room floor plan that seamlessly connects the living area, dining space, and chef’s kitchen. The kitchen features a large entertaining island, premium finishes, and generous seating—ideal for hosting family and friends. The primary suite is a serene retreat with a spa-style ensuite bath, creating a private sanctuary for unwinding after a day in the sun. Two more king bedrooms all with en-suite bathrooms allow privacy for guests. Everyone will love the bunk room also with en-suite bathroom. Step outside to expansive outdoor spaces surrounded by lush tropical landscaping. Enjoy the Florida sunshine by the heated pool and infinity edge spa, relax with a drink in hand, or gather for evening conversations under the stars. The turfed backyard provides a lush area for pets and additional seating areas. The home also features rooftop deck with sweeping intercoastal water views, perfect for taking in unforgettable sunsets. Multiple balconies around the allows you to enjoy the incredible island weather. A spacious 2-car garage provides room for vehicles, a golf cart, and additional storage. Every detail has been thoughtfully designed for comfort, convenience, and effortless island living. Situated in one of Anna Maria Island’s most desirable areas, this home places you moments from everything that makes island life special. Take advantage of the private community boat ramp and quick access to the beautiful waters of Tampa Bay and the Gulf. Currently utilized as a short-term vacation rental with great rental revenue and many 5-star reviews, this home provides a fantastic investment opportunity.
Listing is courtesy of: LESLIE WELLS REALTY, INC. (941-776-5571)
Listing Agent: Leslie Wells (941-776-5571)
145 50TH ST, HOLMES BEACH, FL 34217
$2,149,000376 Days on yellowkey MLS ID: A4654712
REDUCED by $1,000 (0.0%) on 06/10/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2040 Built: 2008 Tax: $23,038 (2024)Community: Coastal Cottages IiSpa: NoSingle Family
Taxes:$23,038
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
Remarks: Imagine starting your mornings with a short stroll to the beach to watch the sunrise, spending afternoons in the turquoise Gulf waters, and ending your evenings with spectacular island sunsets! Welcome to island living at its finest, where a dedicated beach access awaits at the end of the street and the best of Anna Maria Island is just moments from your door. This beautiful 4-bedroom, 3.5-bath coastal retreat is perfectly positioned in one of the island’s most desirable locations, offering easy access to the beach, turquoise Gulf waters, local restaurants, boutiques, galleries, and the relaxed charm that makes Anna Maria Island so special. This home offers exceptional flexibility as a private coastal sanctuary, a high-performing weekly vacation rental, or the perfect combination of both. Whether you are seeking a peaceful island escape or a proven investment opportunity, this home delivers unmatched lifestyle appeal and value. Outdoors, a private tropical oasis sets the stage for effortless relaxation and entertaining. Lush landscaping, a heated pool, and multiple outdoor gathering areas invite you to unwind after a day at the beach, lounge poolside beneath the palms, or host family and friends on the covered patio. Inside, the bright open-concept floor plan offers a welcoming coastal feel with spacious living areas, comfortable entertaining spaces, and a well-appointed kitchen designed for gathering. Coastal-inspired interiors and thoughtful design create an inviting retreat for owners and guests alike. Located in the heart of Anna Maria Island, with nearby trolley stops providing easy access from Bean Point to Bridge Street, this home offers a rare opportunity to fully embrace the laid-back rhythm of one of Florida’s most sought-after beach communities!
Listing is courtesy of: HUNT BROTHERS REALTY, INC. (941-388-7017)
Listing Agent: Jennifer Albright (941-284-3092)
522 68TH ST, HOLMES BEACH, FL 34217
$3,045,00027 Days on yellowkey MLS ID: L4962247
REDUCED by $150,000 (4.7%) on 06/22/2026
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2409 Built: 1969 Tax: $20,981 (2025)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$20,981
Tax Year: 2025
Remarks: Experience the ultimate island lifestyle in this exquisite coastal retreat on Anna Maria Island. Nestled on one of the island’s most breathtaking tropical lots, this beautifully updated four-bedroom, three-and-a-half-bath residence offers deepwater canal access to the Gulf and the perfect blend of luxury, comfort, and waterfront living. Sold fully furnished and including a golf cart for added convenience, the home underwent an extensive remodel in 2021 and has been thoughtfully upgraded throughout. Recent improvements include a new seawall and dock with a 10,000-pound boat lift upgraded in 2024, as well as a whole-house propane generator installed in 2026. The property has also had no flood damage. Inside, expansive wood-look plank tile flooring creates a warm and inviting atmosphere throughout the home. The stunning chef’s kitchen features quartz countertops, custom cabinetry, and premium high-end appliances. The main living level includes three spacious guest bedrooms, while the entire upper level is dedicated to a luxurious primary suite complete with dual vanities, a spa-inspired bathroom, and an oversized walk-in closet with washer/dryer. Additional highlights include a 200-square-foot insulated storage attic, a private man cave, and a unique indoor entertainment space featuring an indoor grill, bar, and television area that flows seamlessly to the resort-style pool and outdoor living space. From your private dock, enjoy direct boating access to nearby beaches, waterfront dining, and all the charm that island living has to give. This exceptional property is a rare opportunity to own a true waterfront paradise on one of Florida’s most sought-after islands. Don’t miss your chance to make this dream home your reality.
Listing is courtesy of: BERRY REALTY & APPRAISAL SERVICES PA (863-224-6857)
Listing Agent: Tina Ford (863-581-2443)
605 N POINT DR, HOLMES BEACH, FL 34217
$2,950,000119 Days on yellowkey MLS ID: A4683720
REDUCED by $300,000 (9.2%) on 06/21/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3214 Built: 2012Monthly Fee: $167 Tax: $22,644 (2024)Community: North Point Harbour Unit OneSpa: NoSingle Family
Taxes:$22,644
Remarks: Nestled at one of the highest elevations on Anna Maria Island, this exceptional coastal retreat is located in the highly sought-after North Point Harbour community of Holmes Beach. Built in 2012 with hurricane-rated windows and doors, the home offers both refined elegance and peace of mind, perfectly blending luxury with the relaxed sophistication of island living. A cheerful front porch welcomes you inside, setting the tone for the warmth and charm found throughout. Soaring ceilings and gleaming marble floors create a light, airy ambiance, while coastal architectural details — including multiple porches and charming balconettes — add character and dimension to the design. The beautifully appointed living room is flooded with natural sunlight through two sets of French doors that frame tranquil canal views stretching toward Bimini Bay. These doors open to capture sunny mornings and breathtaking evening sunsets, seamlessly blending indoor and outdoor living. The open floor plan flows effortlessly into the dining and kitchen areas, creating an ideal setting for intimate family meals or hosting guests with ease. The spacious first-floor primary suite serves as a peaceful sanctuary, complete with a lovely ensuite bath and a private deck — perfect for quiet evenings under the coastal sky. Two additional bedrooms are also located on the first floor, including a second ensuite bedroom and a third bedroom with its own bath, offering comfort and privacy for family and visitors alike. Even everyday tasks feel elevated in the expansive and beautifully designed laundry and utility room, conveniently located off the kitchen and garage — a space so thoughtfully appointed it hardly feels like a utility area. The entire second floor is dedicated to a spectacular private suite. This luxurious retreat features two charming balconettes, a large walk-in closet, a spa-like ensuite bath with dual sinks, and a separate office or sitting room — an ideal haven for guests or multi-generational living. Outdoors, boating enthusiasts will appreciate the impressive 20,000-pound boat lift and expansive wraparound dock situated on a short, deep-water canal. With direct access through Bimini Bay to Tampa Bay, the Gulf of Mexico, and the Intracoastal Waterway, this property offers effortless navigation to some of Florida’s most beautiful waters. Life in North Point Harbour is as enriching as it is relaxing. Spend mornings at the nearby Key Royale Golf Club for an early tee time, afternoons joining friends at the community pool or enjoying a friendly match on the tennis courts or padel, and evenings cruising from your private dock into Bimini Bay as the sun melts into the horizon. Here, everyday flows seamlessly from recreation to relaxation, creating a true island lifestyle defined by beauty, convenience, and connection to the water. This extraordinary North Point Harbour residence embodies the very best of elevated coastal living — where thoughtful design, superior craftsmanship, and an unparalleled waterfront location come together to create a truly remarkable island home.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Becky Sirigotis (941-201-8000)
634 KEY ROYALE DR, HOLMES BEACH, FL 34217
$2,999,999122 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)
501 68TH ST, HOLMES BEACH, FL 34217
$2,790,00055 Days on yellowkey MLS ID: A4691893
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2044 Built: 1973 Tax: $12,337 (2025)Community: Bay Palms 13Th UnitSpa: YesSingle Family
Taxes:$12,337
Remarks: Waterfront luxury and exceptional boating access await at this stunning Grand Canal home in Holmes Beach on Anna Maria Island. Situated on one of the island's most desirable deep-water canals, this beautifully updated 4-bedroom, 3-bath residence offers direct boating access to Tampa Bay and the Gulf of Mexico with no fixed bridges, making it a rare opportunity for serious boaters and waterfront enthusiasts. Designed to embrace the island lifestyle, this furnished home (with a few exceptions) enjoys coveted southern exposure, creating a bright and inviting atmosphere throughout the day. Tropical landscaping, a mature mango tree, and a fenced backyard provide privacy, while the heated pool, oversized spa, and expansive 12' x 60' dock with a 20,000-pound boat lift create the perfect waterfront retreat. Inside, walls of impact-rated sliding glass doors showcase spectacular water views and seamlessly connect indoor and outdoor living spaces. White Italian oak-inspired plank tile flooring flows throughout, while the family room features vaulted tongue-and-groove ceilings and a custom entertaining bar. The chef's kitchen is beautifully appointed with quartz countertops, custom cabinetry with appliance garages, a large center island, and premium Fisher & Paykel and Bosch appliances. The thoughtfully designed floor plan includes spacious guest accommodations, a hidden laundry room, and a private primary suite with walk-in closet, water closet, and direct access to a secluded outdoor oasis overlooking the canal. A flexible den easily serves as a fourth bedroom, home office, or additional guest space. Extensive 2021 improvements provide both luxury and peace of mind, including a new roof, impact windows and sliders, and updated dock and pilings. Additional upgrades include all-new Schedule 40 drain piping beneath the slab and a 2025-installed 26KW whole-house generator with a 500-gallon propane tank, ensuring reliable backup power year-round. The covered waterfront lanai is pre-plumbed and wired for a future outdoor kitchen, creating an ideal setting for entertaining family and friends. Additional features include an oversized garage, carport, and ample parking. Located on the prestigious Grand Canal in the heart of Holmes Beach, just minutes from Anna Maria Island's award-winning beaches, waterfront dining, boutique shopping, and island attractions, this exceptional property offers one of the finest boating locations on Anna Maria Island and the perfect combination of luxury waterfront living, deep-water access, and relaxed coastal elegance.** Property information received from third-party sources is considered reliable but is not guaranteed. All information should be independently verified by buyers and buyer's agent.
Listing Agent: Liz Blandford (941-224-3304)
215 83RD ST, HOLMES BEACH, FL 34217
$4,300,000135 Days on yellowkey MLS ID: A4681928
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2675 Built: 2024 Tax: $10,876 (2024)Community: Holmes Beach 31St Unit AmdSpa: YesSingle Family
Taxes:$10,876
Remarks: Sunsational is a freshly built & beautiful new home in Holmes Beach! This four bedroom, 4 and half bathroom pool home is impeccably built by Moss Construction and designed by award winning designer Emily Moss Designs. Which will be featured in Design Magazine soon, it's just THAT amazing! The facade of this incredible home feels like luxury and the minute you step inside it won't disappoint. The textures, the colors, the style of each room creates the perfect home for you to live and or continue renting as an investment home. They thought of everything and there is no lack of detail at every turn. So many things to bring to light about this gorgeous home but one of the most prominent is the back yard. It's literally a space full of beauty and fun. It's Florida outdoor living at its finest. Games, heated pool and spa as well as enough balconies for everyone. The great room creates a space large enough for everyone to come together for dining, movies or anything else the family wants to do together. Sunsation also gives you and your family or guests the ability to get away into their own spaces. With a small media room with wet bar upstairs you can spread out to in case you just can't agree on a movie. There are numerous balconies to escape to and enjoy the warm air and great views of Holmes Beach. Every bedroom is large and cozy. Three of the bedrooms are en-suites and ready for and your guests and you must see the bunk room. EVERY youngster will dive into bed and love the feel of fun in this super creative use of space. Just 2.5 blocks to the coveted sugary beaches of Anna Maria Island. Spend the morning walking the beach, collecting shells and feel the ocean breeze. Come back from the beach and spend the day at a home you literally may never want to leave. If you do decide to venture out, you are a golf cart ride or a bike ride away from it all. Hop on the free Trolley and head out to all the hubs of each cities shops and restaurants. This home is amazing and you simply must come see your new home and start living the Anna Maria Life now!
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)
Listing Agent: Billi Gartman (941-545-8877)
8106 GULF DR #A&B, HOLMES BEACH, FL 34217
$1,449,00057 Days on yellowkey MLS ID: TB8500298
REDUCED by $101,000 (6.5%) on 06/05/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 1600 Built: 1980 Tax: $22,689 (2025)Community: EdgemereSingle Family
Taxes:$22,689
Remarks: Virtually Staged. COASTAL INVESTMENT OPPORTUNITY! TURNKEY ELEVATED DUPLEX JUST ONE BLOCK FROM THE GULF INCLUDING A DEEDED BOAT SLIP! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach! The perfect blend of personal retreat and income producing opportunity positioned just one block from the Gulf with your own private residential beach access. Each unit features 2 bedroom/2 bathroom and has been thoughtfully updated with coastal-inspired style, featuring newer appliances, updated furnishings and comfortable mattresses your guests will rave about, and they already do, with excellent reviews in place. Enjoy peace of mind knowing this home had a prelisting inspection, noting a solid metal roof & A/C system as well as hurricane-impact windows and sliding doors (just 4 years old). Step outside and soak in the island lifestyle. Both units offer private balconies with Adirondack chairs, perfect for morning coffee or sunset breezes. The fully fenced yard (just 6 months old) provides space to add a pool, while the grill in the side yard invites gatherings for relaxed coastal evenings. After a day at the beach, rinse off in the outdoor shower and store your gear in the owner’s storage room. Each unit is equipped with its own laundry/utility room complete with washer and dryer plus golf cart plug-ins for added convenience. The property also includes 2 kayaks, a paddleboard, and bikes, making it easy to enjoy everything the island has to offer. For water lovers, the bonus doesn’t stop there! This property includes a DEEDED BOAT SLIP nearby, giving you quick access to the water anytime you please! "The Launch Pad" is perfect for kayaks, which are included with the property. Bring your imagination for a future dock/boat slip. Built for durability and security, the home is elevated and equipped with flood systems and was regularly maintained for pest and rodent control for added confidence. Located just one street from the Anna Maria City limits, this property allows for weekly rentals, maximizing income potential. Whether you choose to live in one unit and rent the other or lease both for strong returns, this duplex offers flexibility and exceptional value in a prime coastal location. Ideal as a personal getaway, full-time residence or high-performing investment! Follow your nose to the salt air and chase the gorgeous sunset. This is your chance to own a slice of paradise with built-in income potential. No shoes required!
Listing is courtesy of: FLORIDA EXECUTIVE REALTY (813-972-3430)
Listing Agent: Danielle Redner (813-967-0175)
212 72ND, HOLMES BEACH, FL 34217
$2,985,000412 Days on yellowkey MLS ID: A4651200
Bed: 4 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 2272 Built: 2019 Tax: $23,423 (2023)Community: 7173900; West Wind Shores; Lot 16; Block 21; Pb 7/Spa: YesSingle Family
Taxes:$23,423
Tax Year: 2023
Remarks: Newly renovated - Stunning 4-bedroom, 6.5-bath is perfect for beach lovers just a block from the Gulf of Mexico beaches. This island home features a backyard with a private pool and tiki bar, hot tub, BBQ area, covered patio with a foosball table, and a rooftop deck with water views. The main living space, includes a kitchen with a beautiful backsplash and quartz countertops, solid wood cabinets, island seating, couches, and a bright dining room with access to a covered deck overlooking the pool. The third floor hosts the primary bedroom, a private balcony with rooftop deck access, and an ensuite bathroom with a double vanity and a large shower. Outdoor amenities also include a pool, spa, This home is just a quick walk to the beach, and guests can easily take the trolley to Pine Ave for local delicacies, fish at the historic AMI city pier, or kayak in the bay waters.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Gregg Bayer (941-799-9096)
309 57TH ST, HOLMES BEACH, FL 34217
$999,999104 Days on yellowkey MLS ID: A4685855
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1982 Built: 1979 Tax: $4,508 (2025)Community: Holmes Beach 13Th UnitSingle Family
Taxes:$4,508
Remarks: Discover this 4 bedroom, 3 bathroom versatile home, perfectly positioned on Anna Maria Island for effortless coastal living. Located on a spacious 0.23-acre lot (approximately 9,988 sq ft), this property offers many possibilities!! If desired, this home can easily be changed back to a duplex with some modifications making it a 3 bedroom, 2 bathroom unit on one side and a cozy mother in law suite that is 1 bedroom, 1 bathroom unit on the other. Whether you're seeking a multi-generational home, a vacation retreat with rental potential, or an income-generating investment, this setup provides flexibility and charm in one of Florida's most desirable beach communities. Ideal for families or entertaining, featuring ample room for comfortable island-style living. Step outside to a backyard with plenty of space to add your dream pool, creating a private oasis for relaxation under the Florida sun. Or keep the awesome Koi pond and zen feels of the backyard. With its prime location, you're just a short stroll from pristine white-sand beaches and gorgeous sunsets. Walking distance to Holmes Beach restaurants and shops. Schedule a showing today!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Barbara Sato (941-778-7200)
511 BAYVIEW DR, HOLMES BEACH, FL 34217
$5,140,000174 Days on yellowkey MLS ID: A4675904
REDUCED by $150,000 (2.8%) on 06/05/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3353 Built: 2020 Tax: $24,007 (2024)Community: Sunrise ParkSpa: YesSingle Family
Taxes:$24,007
Remarks: Experience the ultimate island paradise in this practically NEW CONSTRUCTION LUXURY WATERFRONT HOME, thoughtfully designed with solid concrete block construction and cutting-edge design and technology. Spanning over 3,300+ square feet, this stunning residence offers 4 bedrooms and 5 full bathrooms, blending elegance, durability, and effortless coastal living. Perfectly positioned just a few short blocks from the Gulf of America, the home also boasts PANORAMIC Intracoastal waterfront views, creating a rare and breathtaking dual-water lifestyle. The half-elevated design provides peace of mind while enhancing views and architectural appeal. Indoors, no detail has been overlooked. Highlights include a butler’s pantry, an upstairs coffee bar just outside the primary suite, and expansive open-concept living spaces ideal for both everyday comfort and entertaining. The luxurious primary retreat offers a serene escape with spa-inspired finishes and seamless indoor-outdoor flow. Step outside to your private waterfront oasis featuring an infinity pool, hot tub, and a fully equipped outdoor kitchen, all designed to maximize sunset views and coastal breezes. Whether hosting guests or enjoying a quiet evening under the stars, this outdoor space is truly exceptional. With waterfront living, modern luxury, and a premier island location, this home offers everything you could ask for—and more. A rare opportunity to own a refined coastal sanctuary that perfectly balances style, comfort, and location. Schedule your private showing today!
Listing Agent: Shannon O'Brien Kerney (941-737-5153)
525 68TH ST, HOLMES BEACH, FL 34217
$6,145,000229 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
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)
618 GLADSTONE LN, HOLMES BEACH, FL 34217
$2,750,00036 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.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Joey Hutchinson (941-518-5585)
303 55TH ST, HOLMES BEACH, FL 34217
$4,375,000105 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
$2,650,00041 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)
105 49TH ST, HOLMES BEACH, FL 34217
$3,490,000117 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 Agent: Jason Sato (941-778-7200)
8321 MARINA DR, HOLMES BEACH, FL 34217
$4,295,000111 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.
531 72ND ST, HOLMES BEACH, FL 34217
$4,500,000103 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
$3,900,00023 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
$3,400,000106 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.
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