Refine Search
Map
Sort by
$1,799,000
3 Beds ⋅ 2 Baths ⋅ Jones Sub SubDv. ⋅ 34217 Zip Code
Welcome to your island paradise, just steps from the sugary white sands of Manatee Beach, where gentle Gulf breezes and the laid-back Anna Maria Island lifestyle await. This beautifully maintained elevated concrete block home offers the perfect blend of coastal elegance, modern updates, and exceptional investment potential. The home is situated on an oversized corner lot, providing privacy and peaceful outdoor living. Featuring 3 bedrooms, 2 bathrooms, and a private elevator, this spacious home is designed for both comfortable everyday living and effortless vacation enjoyment. The open-concept floor plan is filled with natural light and centers around a large kitchen island, perfectly positioned beneath an oversized window overlooking the sparkling pool and rear deck—ideal for entertaining family and friends or enjoying an alfresco meal! The generous primary suite is a true retreat, offering a huge walk-in closet and a luxurious ensuite bath complete with a relaxing Jacuzzi soaking tub. Step outside to your private tropical oasis featuring a newly resurfaced (2022) heated saltwater pool and spa, surrounded by an elegant brick paver deck and professionally landscaped grounds. Enjoy morning coffee on the new front deck (2022) or unwind on the spacious rear deck while soaking in the peaceful island atmosphere and enjoying endless sunsets. The oversized lower level provides incredible flexibility with ample space for a home gym, game room, workshop, or additional storage. A large driveway and covered carports provide abundant parking for family and guests. Major updates include a durable metal roof installed in 2020 offering peace of mind for years to come. Inside features tray ceilings, crown molding, updated lighting and fresh paint in beachy neutral tones. Located in one of Anna Maria Island's most desirable areas, you'll love being able to stroll to Manatee Beach, restaurants, boutiques, and local entertainment. Hop aboard the free island trolley and explore everything the island has to offer—from historic Pine Avenue to Bridge Street and breathtaking Gulf sunsets. With weekly rentals permitted, this property offers outstanding flexibility as a full-time residence, vacation getaway, or income-producing investment, allowing rental income to help offset ownership expenses. Whether you're searching for your dream beach home or an exceptional island investment, this coastal retreat truly offers the best of Anna Maria Island living.

140 50th Street, Holmes Beach
$5,495,000
4 Beds ⋅ 5 Baths ⋅ Sunrise Park SubDv. ⋅ 34217 Zip Code
Imagine waking to the gentle lap of the Intracoastal Waterway just beyond your windows, where 240 feet of prime waterfront unfolds into sweeping panoramic vistas that stretch across the bay. This architecturally stunning custom residence has uncompromising attention to detail, commands one of Holmes Beach’s most coveted bayfront settings — a true waterfront sanctuary on Anna Maria Island’s serene shores. Spanning 4,007 square feet under air with 4 bedrooms and 4.5 bathrooms, this home is a masterclass in coastal luxury living. Sun-drenched interiors flow effortlessly to expansive outdoor realms, where a beach-entry pool beckons for effortless days of swimming and lounging beneath Florida’s endless blue skies. Two private docks and two boat lifts put you seconds from open water — perfect for spontaneous sunset cruises, fishing excursions, or simply watching dolphins play against the horizon. Step inside and discover thoughtfully designed living spaces that embrace the views from nearly every room. A dedicated mother-in-law suite offers privacy and comfort for extended family or guests, while the generous 3-car garage ensures ample room for vehicles, toys, and beach gear. Just a short, leisurely walk to the Gulf of Mexico’s sugar-sand beaches, this location delivers the ultimate island lifestyle: effortless access to world-class shelling, dining, and the laid-back charm that defines Anna Maria Island. Whether entertaining on the waterfront terraces, retreating to the poolside oasis, or simply savoring quiet mornings with coffee overlooking the water, this home captures the essence of elevated coastal living. Rare, refined, and ready for its next chapter — this is island living at its absolute finest.

522 Bayview Drive, Holmes Beach
$1,085,000
3 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
The ultimate island investment or low-maintenance personal paradise has arrived! This fully remodeled 3-bedroom, 2-bathroom villa offers the rare freedom of zero HOA fees combined with high-income weekly rental potential. Originally built with solid mid-century bones, the property carries an effective year built of 2009 and has just undergone a spectacular, top-to-bottom luxury transformation. Step inside to a bright, airy great room boasting vaulted ceilings and elegant crown molding throughout. The stunning chef’s kitchen features a massive island with counter seating, brand-new cabinetry, quartz countertops, and all-new Stainless Steel appliances. Total peace of mind is yours with BRAND-NEW impact-rated windows, exterior doors, and sliding glass doors, complemented by fresh interior/exterior paint and new ceramic tile flooring. The outdoor space is a private tropical oasis, showcasing fresh landscaping with a full irrigation system/landscape lighting and a fully fenced yard. The sparkling heated pool is ready for year-round enjoyment with a brand-new pool heater and pool pump. Offered completely turnkey furnished, this island gem is move in and rental-ready from day one!

324 64th Street, Holmes Beach
$2,175,000
3 Beds ⋅ 3 Baths ⋅ Key Royale SubDv. ⋅ 34217 Zip Code
Welcome to your light-filled Key Royale retreat—an effortlessly elegant coastal charmer on Anna Maria Island. Beautifully refreshed and thoughtfully designed, this home embraces the best of indoor-outdoor living with an open floor plan and walls of sliding glass doors that frame sparkling pool and tranquil water views. As you enter the home, you’re greeted by a bright and spacious living room with inviting views of the outdoors beyond. This welcoming space flows seamlessly into the kitchen and dining area, creating the perfect setting for indoor/outdoor entertaining and everyday enjoyment as living room opens to a covered patio, offering generous space for outdoor dining and lounging. At the heart of the home, a brand-new kitchen shines with a large island, breakfast bar, and dedicated dining area—perfect for gathering and hosting. A well-appointed butler’s pantry adds both function and style, featuring a desk workspace, second sink, and ample cabinetry. Enjoy cooking with top-tier appliances, including dual ovens and sleek induction cooktop. The spacious primary suite is a private sanctuary, where sliders and French doors lead to a serene backyard and a charming back porch—ideal for unwinding with evening cocktails as the sun sets. This sanctuary is also appointed with an ample walk- in closet for your comfort and convenience. Step outside to your own tropical oasis: a sparkling pool and spa, lush lawn, and a sandy beach area complete with a cozy fire pit. Boating enthusiasts will love the oversized dock equipped with a 10,000 lb boat lift, providing gorgeous sunset views over Bimini Bay and direct access to the Gulf, Tampa Bay, and the Intracoastal Waterway. Beyond the beauty, thoughtful upgrades provide peace of mind. In 2022 the seawall was replaced and sewer pipes were scoped and lined with PVC, a flood mitigation system has been installed, and all windows are hurricane-rated. This is more than a home—it’s a lifestyle. Start your mornings with sunlight dancing on the water, spend afternoons cruising the bay or playing a round at the nearby Key Royale Club, and end your days exploring Anna Maria Island’s renowned beaches, boutique shops, and charming restaurants. This property is a true island gem, perfectly capturing the relaxed elegance of coastal living.

617 Dundee Lane, Holmes Beach
$7,485,000
4 Beds ⋅ 4 Baths ⋅ Key Royale SubDv. ⋅ 34217 Zip Code
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!

635 Key Royale Drive, Holmes Beach
$999,000
2 Beds ⋅ 2 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code
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.

2913 Gulf Drive, Holmes Beach
$2,950,000
4 Beds ⋅ 4 Baths ⋅ North Point Harbour SubDv. ⋅ 34217 Zip Code
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.

605 N Point Drive, Holmes Beach
$2,699,000
6 Beds ⋅ 5 Baths ⋅ Jones Sub SubDv. ⋅ 34217 Zip Code
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.

130 50th Street, Holmes Beach
$3,975,000
4 Beds ⋅ 5 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
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!

215 83rd Street, Holmes Beach
$2,399,000
6 Beds ⋅ 6 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code
Welcome to Sands of Time, a recently updated six-bedroom, four-and-a-half-bathroom coastal retreat located less than two blocks from the white-sand beaches in the heart of Holmes Beach on Anna Maria Island. Thoughtfully designed and professionally decorated, this home blends relaxed beach style with upscale comfort, making it ideal as a primary residence, second home, or high-performing investment property. Inside, the spacious layout comfortably accommodates family and guests, with multiple living areas and a fully equipped kitchen designed for entertaining and everyday living alike. High-capacity laundry is conveniently located on the main floor, perfect after long days at the beach. Four private balconies invite you to enjoy morning coffee or evening breezes, while the home’s open flow creates a welcoming atmosphere throughout. The outdoor living space is a true highlight. A private heated pool and spa with a waterslide anchor a beautifully updated backyard featuring a bar with seating, lounge chairs, a large outdoor dining area, an outdoor shower, and a stainless-steel grill. A covered lanai beside the pool offers ample seating and an outdoor television, making it an ideal gathering place day or night. As evening falls, the backyard transforms into a tropical oasis with illuminated palms and ambient lighting. Entertainment continues indoors and in the oversized garage, which has been converted into a game space complete with a ping pong table, foosball table, and arcade game. When it’s time to unwind, the home offers six well-appointed bedrooms, each with a flat-screen television. Four bedrooms feature king beds, including three with en suite bathrooms and private balconies. One bedroom includes two twin beds, while another offers two sets of bunk beds, creating a perfect space for kids or guests. A half bath is located on the main floor, with an additional full bathroom upstairs. Situated on a quiet stretch of Holmes Boulevard, the property offers both privacy and convenience. Shops, restaurants, and island favorites along Pine Avenue are just minutes away, and the free island trolley stops nearby, providing easy access to all seven miles of Anna Maria Island. From boutique shopping and dining to fishing, boating, kayaking through mangroves, dolphin tours, and unforgettable sunsets, everything the island is known for is within easy reach. Sands of Time delivers the best of island living with space, style, and an unbeatable location in the heart of Holmes Beach. Schedule your private showing today!

6908 Holmes Boulevard, Holmes Beach
$3,495,000
4 Beds ⋅ 6 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
Striking modern luxury meets investment potential at The Black Pearl, a four-bedroom, five-and-a-half-bath residence located just a short walk from the beaches of Holmes Beach, downtown shopping and dining, and the island trolley. This architecturally distinctive black-and-white home features a private black-bottom infinity-edge pool, resort-style outdoor living, and a rooftop deck with panoramic Gulf views. Designed for both lifestyle and performance, the home offers a bright open-concept interior, gourmet kitchen with island seating, and four king bedroom suites—each with a private ensuite bath—plus a bonus den with additional sleeping flexibility. Outdoor amenities include a full outdoor kitchen, multiple lounge and dining areas, outdoor shower, and ample on-site parking. Currently part of the Exclusive Vacations luxury rental program, the property offers immediate access to a professionally managed, high-end short-term rental platform focused on premium positioning, elevated guest experience, and revenue optimization. A rare opportunity to own a visually iconic, walkable luxury home with proven short-term rental appeal on Anna Maria Island.

5612 Guava Street, Holmes Beach
$2,150,000
5 Beds ⋅ 4 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
Discover a versatile two-unit property in Holmes Beach offering the flexibility many buyers seek on Anna Maria Island. With a combined total of 5 bedrooms and 4 bathrooms, this property includes two fully turnkey residences: Pool Party South, a 3-bedroom, 2-bath main home, and Pool Party North, a 2-bedroom, 2-bath secondary unit. This configuration is well suited for those looking for a two-unit island home, a vacation property with short-term rental potential, or a second home that can help offset expenses when not in use. Both units feature coastal-inspired updates, including modern tile flooring, granite countertops, stainless steel appliances, newer roofs, and comfortable furnishings. Offered turnkey, the property is ready for immediate enjoyment or rental use. Weekly rentals are permitted, providing owners the flexibility to enjoy the island on their own schedule while generating income when away—an important consideration for buyers seeking short-term rental options on Anna Maria Island. The outdoor living area enhances the relaxed Florida lifestyle with a heated pool and spa, outdoor bar with sink, and multiple areas for dining and lounging. The oversized lot adds a sense of privacy, creating an inviting retreat for both owners and guests. This layout appeals to a variety of uses, including a multi-residence setup, a dual-unit investment property, or a home offering separation between living space and guest accommodations while maintaining rental flexibility. Located just a short walk to the Gulf beaches, as well as nearby dining, shopping, and island amenities, this property captures the ease and charm of Holmes Beach living. For buyers searching for an updated two-unit home with a pool, walkable beach access, and strong rental potential, Pool Party South and Pool Party North provide a compelling blend of lifestyle and opportunity on Anna Maria Island.

314 61st Street, Holmes Beach
$1,059,000
2 Beds ⋅ 2 Baths ⋅ Neptunes Gardens SubDv. ⋅ 34217 Zip Code
Smart Buyers: This Price Improvement Is For You. Weekly rental! Exceptional Investment Steps from Holmes Beach. Welcome to Blue Oasis, a fully renovated ground-level retreat just steps from Holmes Beach and the turquoise waters of the Gulf of Mexico. This stunning 2-bedroom, 2-bath home combines modern luxury with island charm. Featuring a versatile den with a pocket door for added privacy, it’s perfect for a home office or guest space. The den includes a stylish daybed with trundle, offering extra sleeping accommodations without sacrificing comfort or design. Every detail has been thoughtfully upgraded, including a new roof (Summer 2025), freshly finished walls, baseboards, doors, and paint throughout, plus custom closet organizers for added functionality. The kitchen and both bathrooms feature all-new soft-close cabinetry and fixtures, complemented by brand-new appliances—dishwasher, refrigerator, gas range/oven, and washer. Comfort is ensured with a new A/C (November 2024-mounted up from the ground), while the new pool pump with Pentair automation adds convenience and efficiency. The master bath boasts a completely redesigned shower with new tile and hardware, and the entire home is furnished with all-new furniture and décor, from beds, mattresses, and nightstands to a stylish sofa, chairs, dining set, and coastal accents. Outdoors, enjoy new patio furniture, umbrellas, lighting, and a perfect sized pool with optional spa jets plus a shed stocked with new beach chairs and a beach cart. Rinse off in the outdoor shower offering both hot and cold water. Additional upgrades include new TVs in every room, palm tree shutters, creating a turnkey property that’s ready to impress. With its prime location just a four-minute walk to the beach, easy access to shops and dining, and exceptional rental performance, Blue Oasis delivers a fantastic ROI and lifestyle appeal—perfect as a short-term rental, second home, or long-term investment in one of Florida’s most sought-after coastal markets. Make your move on this turnkey coastal gem today!

5803 Imperiore Avenue, Holmes Beach