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SEA SIDE GARDENS - A4688793 - 445 63RD ST, HOLMES BEACH, FL 34217 2 Days on yellowkey
$579,000 | Single Family Home | 2 beds | 2.0 baths
This is what Anna Maria Island living is all about. Located in the desirable Seaside Gardens community, this renovated 2-bedroom, 2-bath home offers spacious rooms, updated interiors, and a relaxed, airy feel. Inside, you’ll find new stainless steel appliances, quartz countertops in both the kitchen and bathrooms and waterproof luxury vinyl plank flooring throughout. A newer roof and windows add to the list of thoughtful updates. The generously sized bedrooms provide plenty of room to unwind, while the renovated bathrooms offer a clean, modern finish. A dedicated laundry room with washer, dryer, and ample storage adds everyday convenience. Step outside to a fully fenced backyard—perfect for entertaining friends and family along with a private driveway for on-site parking. Being offered furnished, this home is ready to enjoy as your personal island retreat or as an income-producing rental. Spend your days boating, playing pickleball, or relaxing on the beach, soaking in the turquoise waters and sugar-sand shoreline Anna Maria Island is known for. With community amenities and the Intracoastal Waterway just steps away, it’s easy to enjoy the laid-back island lifestyle. Golf carts and pets are welcome, and the trolley stop near the neighborhood entrance makes exploring the island simple and convenient. A comfortable, well-located home in a sought-after community—this is island living made easy.
Listing is courtesy of: DUNCAN REAL ESTATE, INC.
HOLMES BEACH DEV 3RD UNIT - A4688098 - 114 78TH ST, HOLMES BEACH, FL 34217 3 Days on yellowkey
$999,900 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Prime Holmes Beach opportunity just steps to the beautiful beaches of Anna Maria Island. Located on a quiet street in one of Holmes Beaches most desirable areas, this property is all about location, flexibility, and future upside. The existing structure has been impacted by Hurricane Helene and is ready for its next chapter. For investors, builders, or end users looking to capitalize on a high-demand island market, this is a chance to secure a well-positioned parcel with strong long-term potential. Holmes Beach continues to see consistent demand driven by its walkability to the beach, access to dining and shopping, and its appeal as both a second-home and income-producing market. Whether your strategy is to renovate, reposition, or build new, the fundamentals here support the investment. Short distance to the Gulf, close to everything on the island, and situated in an area where quality properties continue to command attention—this is a strategic play in a market where opportunities like this are increasingly limited.
Listing is courtesy of: RE/MAX ALLIANCE GROUP
ILEXHURST - A4686689 - 2806 GULF DR, HOLMES BEACH, FL 34217 8 Days on yellowkey
$1,095,000 | Single Family Home | 3 beds | 2.0 baths | 4 gar
Effortless Island Living at this elevated 3BD/2BA home, where breezy interiors and sunlit spaces create the perfect island escape just steps from the sand. Located in a highly desirable weekly rental zone, this property offers exceptional flexibility and income potential. Inside, the living and dining area welcomes you with abundant natural light and easy access to the expansive front deck. The kitchen features generous counter space and a breakfast bar, making entertaining effortless, while the split bedroom layout provides comfort and privacy. Downstairs, an oversized garage delivers convenience with tandem space for up to four vehicles, along with plenty of room for beach gear, bikes, and additional storage. The low maintenance outdoor space lets you spend more time enjoying the coastal lifestyle, whether you're heading out for sunset walks or relaxing in the ocean breeze from the deck. With its unbeatable location, strong rental appeal, and inviting coastal feel, this property checks lots of the boxes. Bring your decorator touches and create your personal island vibe. Easy access on and off the island, close to shopping, dining, a trolley stop and the beach is right at your back door. What more or you waiting for? Make this your perfect little slice of island life!
VILLAS ON FIFTH AVE - A4687756 - 4118 5TH AVE, HOLMES BEACH, FL 34217 14 Days on yellowkey
$2,495,000 | Single Family Home | 6 beds | 3.5 baths
Welcome to your dream coastal retreat on Anna Maria Island—where luxury, location, and income potential come together seamlessly. This stunning 6-bedroom, 4-bathroom elevated home is a rare find—a property of this size and scale can no longer be built in Holmes Beach. Perfectly positioned just steps from the public beach and turquoise waters of the Gulf, as well as nearby restaurants, shopping, and local attractions, this Mediterranean-style home delivers the ultimate island lifestyle. Thoughtfully designed for both comfort and high-performing investment, it boasts an exceptional rental history to match. Inside, you’ll find a spacious, thoughtfully designed layout ideal for hosting large groups and families. The home features an open floor plan, high ceilings, spacious bedrooms, a 4-person elevator, and multiple balconies, including private outdoor spaces off both primary suites and an additional balcony off the kitchen—perfect for morning coffee, sunset cocktails, or simply enjoying the coastal breeze. The heart of the home opens into a bright, airy living space, complemented by lower level bonus game room that adds an extra layer of entertainment and flexibility. An elevator provides seamless access to all three levels, while ample storage throughout ensures everyday comfort and convenience. Step outside to your own private paradise—a true backyard oasis featuring a sparkling pool, relaxing jacuzzi, a covered dining area, and a spacious conversation lounge—offering the perfect setting to unwind and entertain after a day at the beach. Major recent upgrades (2025), totaling over $100,000, include a new terracotta tile roof, a new pool pump and heater, updated soffits and fascia, and refreshed and reenforced rear decking—providing peace of mind and long-term value. Additional highlights include: Parking for up to 6 vehicles—a rare island luxury Proven rental income with 10 years of consistent, stellar reviews Strong rental projections exceeding $150,000 annually Whether you're searching for a high-performing investment property, a second home, or a full-time coastal escape, this Anna Maria Island gem checks every box.
Listing is courtesy of: SATO REAL ESTATE INC.
KEY ROYALE 8TH ADD - A4687421 - 635 KEY ROYALE DR, HOLMES BEACH, FL 34217 16 Days on yellowkey
$7,485,000 | Single Family Home | 4 beds | 4.0 baths
This bayfront Key Royale home is ideally situated on the southern side of Key Royale, offering a more protected setting away from the north wind and enhancing year-round outdoor enjoyment. Truly a World of Its Own—delightful bayfront living with sweeping views of the crystal-clear waters of Anna Maria Sound and Tampa Bay. This elevated, single-level custom-built coastal residence is a tribute to exceptional design, premier location, and impeccable construction, finishes, and taste. Calm coastal hues and shell stone travertine flooring flow throughout the soaring living spaces, highlighted by tongue-and-groove ceilings with solid wood beams. The home showcases custom cabinetry with 100-year-old pine accents, extensive millwork, and a handcrafted TV feature wall. Additional features include a Control4 AV system, upgraded custom lighting and fans, an elevator, 8-foot solid core interior doors, whole-home sound system, plantation shutters, custom motorized window treatments, and central vacuum. The chef’s kitchen is equipped with Thermador commercial-grade appliances, a built-in pantry, and double laminated-edge granite countertops. Expansive bay views are captured from nearly every angle, while sliding glass doors open to an elegant 63-foot balcony complete with an outdoor kitchen and Trex staircase leading to the pool area below. Three of the four bedrooms are ensuite, all featuring rich Ipe wood flooring, custom closet systems, and luxurious bathrooms finished with travertine flooring and Moen body spray shower systems. Built to the highest standards, the exterior boasts a commercial-grade 24-gauge standing seam metal roof, PGT impact windows and doors, second-floor block construction, poured concrete porches, a Cantera entry door, and Icynene attic insulation. The spacious garage includes insulated doors and durable epoxy flooring. Outdoors, the home transforms into a private waterfront retreat with a bayside freeform pool and spa, expansive travertine deck for lounging and dining, and a covered cabana. Boating enthusiasts will appreciate the Trex dock with water and electric, along with 28,000 lb and 10,000 lb boat lifts. This stunning residence is a decorator’s masterpiece and a true feast for the senses. It presents a rare opportunity to embrace an extraordinary coastal lifestyle. Sold turnkey furnished less personal exceptions!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA
SPORTSMANS HARBOR REV - A4687047 - 216 N HARBOR DR #A, HOLMES BEACH, FL 34217 17 Days on yellowkey
$3,100,000 | Single Family Home | 4 beds | 4.5 baths
Pre-Construction. To be built. Brought to you by Noah Thomas Builders, designed to capture the essence of elevated island living while delivering strong long-term value. This home is intentionally designed with a flowing, open layout balanced by thoughtfully separated spaces—creating the ideal environment for both private use and high-end guest accommodations. The main living area is anchored by a statement kitchen featuring an oversized island, premium appliance package, custom cabinetry, and clean, coastal finishes that feel both refined and effortless. Outdoor living is curated as a private resort-style experience, thoughtfully positioned to function as its own extension of the home. The space is designed to center around a private pool and spa, with ample room for covered lounging, outdoor dining, and entertaining. Whether hosting guests or enjoying a quiet evening, the outdoor environment is intended to feel relaxed—capturing the essence of island living. Elevating the experience even further, the rooftop deck offers a private escape above it all—an ideal setting for sunset views, evening gatherings, and capturing the coastal breeze. This signature feature not only enhances everyday living but adds a distinct advantage for those considering rental potential. Every detail of the home is designed with both luxury and resilience in mind, including a private elevator, whole-home generator, impact-rated windows and doors, and construction planned to meet or exceed current FEMA and coastal building standards—delivering both peace of mind and long-term durability. Positioned in the heart of Holmes Beach on Anna Maria Island, you’re just moments from the beach, local restaurants, marinas, and the island trolley. Whether envisioned as a private coastal retreat, an income-producing luxury rental, or a long-term hold in a high-demand market, this property represents a rare opportunity to secure a thoughtfully designed, high-quality new construction home in an exceptional island setting. Finishes, materials, and specifications may change during the build process. Pricing, availability, and final details subject to adjustment prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST
KEY ROYALE 15TH ADD - A4686733 - 680 KEY ROYALE DR, HOLMES BEACH, FL 34217 22 Days on yellowkey
$2,495,000 | Single Family Home | 3 beds | 3.0 baths | 1 gar
Stunning Fully Remodeled Canal-Front Oasis in Prestigious Key Royale! Welcome to your slice of paradise, a beautifully reimagined 3-bedroom, 3-bathroom waterfront retreat on exclusive Anna Maria Island. This coastal gem has undergone a complete remodel, blending contemporary luxury with relaxed island living in the sought-after Key Royale community, home to the island’s only private golf course and just moments from pristine Gulf beaches. Step inside to discover an open, light-filled floor plan with high-end finishes throughout: sleek new kitchens with premium appliances, elegant quartz countertops, and custom cabinetry; spa-like bathrooms featuring designer fixtures and walk-in showers; and spacious bedrooms offering serene comfort. Every detail has been thoughtfully updated for effortless Florida living. Outside, your private backyard paradise awaits – a sparkling heated pool and spa with a chiller for year-round enjoyment, perfect for cooling off on warm summer days or soaking under the stars. The expansive lanai provides ample space for outdoor dining, lounging, and entertaining while overlooking the serene canal. Boaters will love the direct canal access with a 12,000 lb boat lift and private dock with electric– ideal for quick runs to the Gulf, fishing, or exploring the Intracoastal waterways. No bridges to the bay means easy outings! Located in the heart of Holmes Beach on Anna Maria Island, you’re just minutes from world-class white-sand beaches, charming restaurants, boutique shops, and the laid-back vibe that makes this area a top vacation and year-round destination. Schedule your private showing today!
ILEXHURST - A4684724 - 2913 GULF DR, HOLMES BEACH, FL 34217 27 Days on yellowkey
$1,099,000 | Single Family Home | 2 beds | 2.0 baths
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
BAY PALMS ADD 8TH UN - A4685680 - 531 72ND ST, HOLMES BEACH, FL 34217 28 Days on yellowkey
$4,500,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
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
HOLMES BEACH 11TH UNIT - A4685639 - 303 55TH ST, HOLMES BEACH, FL 34217 30 Days on yellowkey
$4,495,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar
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.
HOLMES BEACH DEV 1ST UNIT - A4684654 - 117 81ST ST, HOLMES BEACH, FL 34217 31 Days on yellowkey
$2,950,000 | Single Family Home | 4 beds | 3.5 baths
Welcome to 117 81st Street in Holmes Beach, a custom-designed coastal retreat steps to the beach that has been completely renovated inside and out, offering the perfect blend of modern luxury and effortless island living. This beautifully updated 4-bedroom, 3.5-bath home is being sold turnkey furnished, making it move-in ready or immediately available as a high-performing rental investment. The first-floor open layout is designed for both entertaining and everyday comfort, featuring a spacious living area that flows seamlessly into the gourmet kitchen and dining space. The kitchen is a true centerpiece of the home, showcasing a large island with custom concrete countertops, distinctive range accents, and ample space for gathering. Adjacent to the kitchen, the dining room features a built-in bar with open shelving, creating the perfect setting for hosting guests or enjoying relaxed island evenings. A conveniently located half bath is also situated on the main living level. All four bedrooms are located on the upper level, offering privacy and a well-designed layout for families and guests. The spacious primary suite serves as a relaxing retreat and features a beautifully designed bathroom with an oversized walk-in shower. A fun and functional bunk room with its own en suite bathroom provides the perfect space for kids or visiting guests, while two additional bedrooms share a Jack-and-Jill bathroom, creating a comfortable and efficient layout for larger groups. Step outside to your private backyard oasis featuring a brand-new heated pool and spa, a covered patio with warm wood ceilings, outdoor grill area, multiple lounge spaces, and two inviting fire pits—perfect for entertaining or unwinding after a day at the beach. Additional upgrades include a brand-new metal roof, along with extensive renovations throughout the home that make this property feel completely refreshed and modern. Located just steps from the white sand beaches of Anna Maria Island, the home is also conveniently close to the island’s best restaurants, shops, and local attractions. Whether you’re looking for a high-revenue producing short-term rental, a primary residence, or a private Florida retreat, this exceptional property offers incredible versatility in one of the island’s most desirable locations.
Listing is courtesy of: COLDWELL BANKER REALTY
SPORTSMANS HARBOR REV - A4684262 - 227 S HARBOR DR, HOLMES BEACH, FL 34217 31 Days on yellowkey
$3,650,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar
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.
KEY ROYALE 15TH ADD - A4684704 - 608 GLADSTONE LN, HOLMES BEACH, FL 34217 32 Days on yellowkey
$1,885,000 | Single Family Home | 3 beds | 2.0 baths
Tucked within the exclusive waterfront community of Key Royale on Anna Maria Island, this beautifully renovated canal-front residence offers an exceptional blend of island charm, privacy, and effortless island living. Designed to embrace the Florida lifestyle, the home is centered around a spectacular pool courtyard, where almost every room opens to the expansive outdoor living space, creating a seamless connection between indoors and out. Bathed in natural light due to its desirable southern exposure, the home invites sun-filled days by the pool and tranquil evenings under the coastal sky. The thoughtfully designed split floor plan features a private primary suite with ensuite bath, along with two additional guest bedrooms and a well-appointed second bathroom, offering comfort and flexibility for family and visiting guests. The home offers a new roof and seawall was replaced in 2006, ensuring lasting quality and peace of mind for years to come. Ideally situated on a deep-water canal, the property provides a 10,000 lb boat lift and dock with water and electric. Direct access to Tampa Bay, the Gulf of Mexico, and the Intracoastal Waterway, make it a dream for boating enthusiasts and lovers of life on the water. Also, located just moments from Anna Maria Island’s world-renowned beaches, charming boutiques, and acclaimed dining, this residence captures the essence of luxury coastal living in one of the island’s most coveted neighborhoods. Don't miss this extraordinary opportunity to experience the elegance, serenity, and waterfront lifestyle that make Key Royale truly exceptional.
HOLMES BEACH FOURTEENTH UNIT - A4685187 - 504 58TH ST, HOLMES BEACH, FL 34217 35 Days on yellowkey
$1,450,000 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Recently renovated 3 bedroom, 2 bath canal front home on a beautiful, deep water, natural-lined mangrove canal with a boat dock. This meticulously cared for home is located on a very quiet street in Holmes Beach. A shady, private paver lined courtyard sits canal side and is a serene spot to escape. PGT Hurricane rated windows & doors installed Oct. 2021, new metal roof installed 2025, new A/C, ductwork & insulation 2025 and all new appliances 2025. Centrally located on the island just steps from Holmes Beach City Park & Public Event Venue, with pickleball courts, a dog park and The Island Library. Walking distance to great dining options & local shopping boutiques. Hop on your golf cart to enjoy the pristine beach & Gulf located just minutes from your door! One car garage and ample driveway parking. This great home is truly "island living" at its best.
Listing is courtesy of: MIKE NORMAN REALTY INC.
SPORTSMANS HARBOR REV - A4684027 - 243 S HARBOR DR, HOLMES BEACH, FL 34217 38 Days on yellowkey
$3,000,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar
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.
JONES - A4683981 - 105 49TH ST, HOLMES BEACH, FL 34217 42 Days on yellowkey
$3,750,000 | Single Family Home | 4 beds | 4.0 baths
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!
HAVERKOS COURT - A4683517 - 205 HAVERKOS CT, HOLMES BEACH, FL 34217 43 Days on yellowkey
$1,525,000 | Single Family Home | 3 beds | 2.0 baths
Welcome to your slice of paradise on beautiful Anna Maria Island! This 3-bedroom, 2-bath island retreat is ideally located just 2.5 blocks from the sugar-sand beaches of the Gulf of Mexico, offering the ultimate coastal lifestyle in one of Florida’s most sought-after destinations. Designed for relaxation and entertaining, the home features an amazing ground-level pool with spa — your own private tropical oasis perfect for soaking up the Florida sunshine or unwinding after a day at the beach. The spacious layout comfortably accommodates family and guests, making every stay feel like a vacation. Enjoy being within walking distance to all that Anna Maria has to offer — charming local shops, great dining, grocery options, and more. Leave the car behind and embrace the true island lifestyle. In addition to being a wonderful personal getaway or primary residence, this property is a great rental home with strong appeal to vacationers seeking location, comfort, and exceptional outdoor living. Its proximity to the beach, walkability, and desirable pool/spa amenities make it highly attractive for short-term rental opportunities. Whether you're looking for an island escape, investment property, or both — this home delivers the very best of Anna Maria Island. Come live your Anna Maria Life!
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE
NORTH POINT HARBOUR UNIT ONE - A4683720 - 605 N POINT DR, HOLMES BEACH, FL 34217 44 Days on yellowkey
$3,395,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
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.
THE VILLAS ON 50TH STREET - A4683830 - 130 50TH ST, HOLMES BEACH, FL 34217 45 Days on yellowkey
$2,799,000 | Single Family Home | 6 beds | 4.5 baths | 2 gar
Own the sunset and step into a lifestyle buyers dream about—and renters actively seek out. Just moments from the Gulf, this stunning 6-bedroom, 4.5-bath coastal retreat delivers the perfect blend of luxury, comfort, and exceptional income potential. Designed to host and impress, the home lives like a private resort. Outside, guests are drawn to the resort-style pool with a sun shelf, a relaxing hot tub, and a tranquil waterfall feature. The outdoor bar and expansive patio create an effortless entertaining space, while the rooftop deck offers unforgettable Gulf-view sunsets that elevate every stay. Inside, the bright, open-concept design is made for connection, comfortably accommodating large groups, families, or vacation guests. High-end finishes meet relaxed coastal style, creating a space that feels both upscale and welcoming—exactly what today’s buyers and renters are looking for. Whether you're building a strong vacation rental portfolio or securing your own coastal escape, this property stands out as a high-demand, memory-making destination with proven appeal.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC
KEY ROYALE - A4682874 - 607 NORTH POINT DR, HOLMES BEACH, FL 34217 45 Days on yellowkey
$1,795,000 | Single Family Home | 3 beds | 2.0 baths
CANAL FRONT IN KEY ROYALE - NORTH POINT HARBOUR WITH COMMUNITY POOL AND TENNIS COURTS. Experience unparalleled luxury in this exquisite and elevated waterfront home. Beautifully remodeled with a NEW ROOF (2025) and turnkey furnished 3-bedroom, 2-bathroom waterfront home, offering nearly 2,000 square feet of luxurious living space and includes a community pool and tennis courts! The home sits at 11 feet elevation and had no flood damage. Located in the highly sought-after North Point Harbour community of Key Royale on Anna Maria Island, this home epitomizes an idyllic blend of elegance and tranquility. Having undergone tasteful renovations, this canal-front gem is fully furnished and move-in ready. It boasts 83 feet of waterfront with a private dock and a 12,000 lb boat lift, allowing you to embark on sunset cruises directly from your backyard into the open water with no bridges obstructing your path. The primary suite is a true retreat with a balcony overlooking the water, complete with a luxurious en-suite bathroom, walk-in closet. Additional bedrooms are generously sized and elegantly appointed. A lovely courtyard patio overlooking the water invites you to enjoy the outdoors and dine alfresco. North Point Harbour residents enjoy exclusive access to the community pool, tennis and pickleball courts, and clubhouse. Additionally, you have the option to join the private Key Royale Golf Club, featuring the island’s only golf course, along with dining and social activities. This home is just a golf cart ride away from Anna Maria Island’s stunning beaches and all its attractions, perfect for embracing the island lifestyle year-round or as a seasonal retreat. This home combines the best of luxury living with the beauty and serenity of a waterfront setting. Don’t miss the opportunity to make this dream home yours.
KEY ROYALE 7TH ADD - A4683541 - 634 KEY ROYALE DR, HOLMES BEACH, FL 34217 47 Days on yellowkey
$3,175,000 | Single Family Home | 4 beds | 3.5 baths
Elevated waterfront living in Key Royale — built for confidence, designed for ease. Welcome to 634 Key Royale Drive, a 2011-built canal-front residence offering over 3,000 square feet of refined coastal living in one of Anna Maria Island’s most sought-after neighborhoods. Positioned high and built to modern standards, this home delivers peace of mind along with sweeping water views from nearly every room. Bright, sun-filled interiors open seamlessly through French doors to a private outdoor retreat featuring a heated pool, Trex dock, 10,000-lb boat lift, and jet ski lift — ideal for boaters who want quick access to Tampa Bay and the Gulf. Inside, the kitchen has just been refreshed with new quartz countertops and pairs beautifully with stainless appliances and an oversized breakfast bar built for gathering. Two brand-new AC units provide efficient climate control, complemented by Icynene spray-foam insulation and two Rinnai tankless water heaters for energy-conscious living. The main-level primary suite captures peaceful canal views and features dual vanities, a soaking tub, and custom port windows. Upstairs offers three additional guest bedrooms, two baths, and a breezy balcony overlooking the water. Built with impact-rated windows and doors and showing no storm damage to date, this elevated home offers the structural integrity today’s buyers are seeking — without sacrificing comfort or style. An oversized garage with 12’ ceilings and a 9’ door easily accommodates a boat, golf cart, or additional storage. Located in the desirable Key Royale community of Holmes Beach, you’re minutes to the beach, golf, dining, and island favorites — yet tucked away in a quiet canal setting. For buyers seeking a newer-build, low-maintenance waterfront home with strong construction and immediate boating access, 634 Key Royale Drive delivers exceptional value on Anna Maria Island.
Listing is courtesy of: SALTY MERMAID REAL ESTATE LLC
HOLMES BEACH 17TH UNIT - A4681843 - 501 65TH ST, HOLMES BEACH, FL 34217 47 Days on yellowkey
$1,750,000 | Single Family Home | 4 beds | 3.0 baths | 1 gar
**Seller is offering a $25,000 incentive for a contract closed before June 1st!** Discover a rare opportunity in Holmes Beach: a fully renovated four-bedroom, three-bathroom waterfront home offering immediate access to the Intracoastal Waterway and the Gulf of America, along with direct beach access just steps away. Every element of this property is brand new, creating a true turnkey residence equally suited for personal enjoyment or investment. Set on a deep-water canal with no bridges to open water, the home is designed for effortless boating. The composite dock and electric boat lift allow for quick departures to the Gulf, while the brand-new pool anchors a private outdoor setting ideal for entertaining or quiet relaxation. Whether returning from a day on the water or an afternoon at the beach 2 blocks away, the outdoor spaces are designed to complement the island lifestyle. Inside, the renovation reflects a clean, modern coastal design with thoughtful functionality throughout. Four spacious bedrooms and three beautifully appointed bathrooms provide flexibility for hosting family and guests. Upgrades such as instant hot water at every faucet and an EV-ready charging connection add everyday convenience, while the garage offers valuable storage (an increasingly important feature on Anna Maria Island) plus potential for a future ADU conversion (buyer to verify zoning, permits, and feasibility). Holmes Beach remains one of the most desirable enclaves on Anna Maria Island, known for its walkability, local dining, boutique shopping, and relaxed sophistication. With monthly rentals permitted, this home offers exceptional versatility as a primary residence, seasonal retreat, or income-producing property. Completely updated, impeccably located, and ready for immediate occupancy and with all furniture available for separate purchase, it represents island living at its finest.
Listing is courtesy of: KW SUNCOAST
KEY ROYALE 9TH ADD - A4679856 - 625 DUNDEE LN, HOLMES BEACH, FL 34217 52 Days on yellowkey
$2,200,000 | Single Family Home | 3 beds | 2.0 baths
Under contract-accepting backup offers. Welcome to 625 Dundee Lane, a beautifully remodeled waterfront retreat offering the perfect blend of modern luxury and coastal living. This stunning 3-bedroom, 2-bathroom home has been completely updated with brand-new finishes throughout, offering a fresh and thoughtfully updated living experience in a prime canal-front setting. Situated on a scenic canal with 90 feet of water views from the backyard, this property is a boater’s dream. The private dock and boat lift provide quick and easy access to open water, making sunset cruises and weekend adventures effortless. Inside, you’ll find a thoughtfully redesigned interior featuring light-filled living spaces, all-new upgrades, and storm windows for added comfort and peace of mind. Every detail has been refreshed to create a clean, modern aesthetic while maintaining a warm, coastal feel. Step outside to your private waterfront oasis complete with a pool and spa, perfectly positioned to capture long water views and breathtaking sunsets. Whether you’re relaxing in the spa, entertaining poolside, or enjoying a quiet evening by the canal, this backyard is designed for true Florida living. Ideally located close to beautiful beaches, shopping, and top-rated restaurants, this home offers the perfect balance of tranquility and convenience. Don’t miss this opportunity to own a fully remodeled canal-front pool home with exceptional water access and unforgettable views.
PELICAN PERCH - A4682621 - 3007 AVENUE F, HOLMES BEACH, FL 34217 52 Days on yellowkey
$4,200,000 | Single Family Home | 8 beds | 6.0 baths
One or more photo(s) has been virtually staged. Beachfront property on the sugary sands of Anna Maria Island! Experience the pinnacle of waterfront living with majestic sunsets and breathtaking Gulf views. This beachfront property offers two separate structures and is zoned as a Land-Condominium with ability to have four separate condominium units. Being sold turnkey, the beachside house offers a total of four bedrooms and four baths and can be divided into two separate condominium units. The downstairs two bedrooms, two baths are ideal for guests and family for space and privacy. The bottom floor was recently repaired and updated due to damage from Hurricane Helene. The upstairs unit is in mint condition and outfitted with cathedral ceilings, laminate floors, granite kitchen counters and stainless steel appliances. The living area provides panoramic Gulf views and opens up to the exterior balcony to enjoy grilling out and listening to the sound of crashing waves to help take away all your worries. The turnkey back house has two separate units, upstairs and downstairs, which are ideal for additional guest and rental income. The upstairs and downstairs units are being rented and have a full schedule for potential future rental reservations. Each unit offers two bedrooms and one bath. This property offers so many opportunities to make it your own. With 50-by-100 feet of non-buildable lot owned by the seller, the property offers its private beach access. It's all about the view, the beach, the aqua blue waters and sunsets. This property is being sold as three parcels. Schedule your showing today to see this amazing property.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY
HOLMES BEACH 34TH UNIT - TB8475905 - 213 84TH ST, HOLMES BEACH, FL 34217 56 Days on yellowkey
$2,250,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Under contract-accepting backup offers. Positioned on a naturally elevated homesite for enhanced drainage and reduced flood exposure, this custom-built Anna Maria Island retreat delivers the perfect blend of luxury, flexibility, and proven investment potential. Offered turnkey furnished, the residence features 4 bedrooms, 3 full baths, and a layout designed for effortless full-time living or high-performing vacation use. The light-filled main living level showcases soaring cathedral ceilings, an open-concept great room, and retractable glass doors that create seamless indoor-outdoor living to the expansive deck. The chef’s kitchen is built to impress with double ovens, commercial-size refrigerator, custom cabinetry, soapstone countertops, large island seating, and a brand-new ZLINE gas cooktop, all enhanced by suspended track lighting. Recent improvements include fresh interior and exterior paint, fresh sod and landscaping, an upgraded irrigation system, and a new pool heater and pump — delivering true move-in-ready peace of mind. The private primary suite offers a balcony retreat, walk-in closet, soaking tub, and walk-in shower. Two additional upstairs guest rooms share a spacious bath, while the fourth bedroom on the lower level provides direct pool access and an additional full bath — ideal for guests or multi-generational living. Outdoor living steals the show with a heated pool and spa, waterfall feature, gas firepit, built-in seating, and lush tropical landscaping for maximum privacy and year-round enjoyment. Zoned R1 with 30-night minimum rentals and a strong established rental history, this property offers exceptional flexibility for personal use, seasonal escapes, or income production. Located moments from the Gulf beaches, dining, and shopping of Anna Maria Island, this elevated, furnished coastal home is the total package.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE
HOLMES BEACH 31ST UNIT AMD - A4680377 - 529 77TH ST, HOLMES BEACH, FL 34217 59 Days on yellowkey
$5,795,000 | Single Family Home | 5 beds | 4.0 baths
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.
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE
SPORTSMANS HARBOR REV - A4681733 - 214 N HARBOR DR #A, HOLMES BEACH, FL 34217 60 Days on yellowkey
Pre-Construction. To be built. Brought to you by Noah Thomas Builders, designed with both lifestyle and long-term value in mind, this modern coastal residence is planned to showcase a spacious, open-concept design with thoughtfully separated living areas and a layout ideal for both personal use and guest accommodations. The design emphasizes comfort, privacy, and functionality—features that appeal to today’s luxury coastal buyers and renters alike. The open-concept design is anchored by a chef-inspired kitchen envisioned with a large gathering island, premium appliance selections, custom cabinetry, and refined coastal finishes—perfect for entertaining and maximizing guest appeal. Flowing seamlessly into the main living areas, the design emphasizes effortless indoor-outdoor living, with outdoor spaces to include a private pool and spa, creating a true island retreat. A true standout feature is the rooftop deck, planned as a private island retreat ideal for sunset views, entertaining, and elevated outdoor living—an amenity that significantly enhances both lifestyle enjoyment and rental desirability. Additional features include a private elevator, whole home generator, impact-rated windows and doors, and construction planned to meet or exceed current FEMA and coastal building standards, delivering durability, resiliency, and peace of mind. Located in the heart of Holmes Beach on Anna Maria Island, this homesite offers walkable access to sugar-sand beaches, restaurants, marinas, and the island trolley. Bradenton Beach remains one of the Gulf Coast’s most desirable and supply-constrained markets, making new construction opportunities particularly attractive from an investment perspective. Whether envisioned as a luxury second home, income-producing property, or long-term coastal hold, this project offers the opportunity to secure a high-quality, FEMA-compliant new construction asset in a proven beach market with enduring demand. Finishes, materials, and specifications may change during the build process. Pricing, availability, and final details subject to adjustment prior to completion.