Homes for Sale Near Martha B. King Middle in Holmes Beach - 89 homes

Remarks: You must see this charming 1940s Craftsman cottage tucked into the historic heart of Anna Maria Island! This beautifully renovated two-bedroom, two-bath homestead blends timeless Old Florida character with effortless coastal charm. The home’s distinctive pecky pine exterior pay homage to its heritage while creating a warm, inviting island aesthetic that reflects the relaxed spirit of Anna Maria’s historic beach community. Inside, the home opens into a light-filled open floor plan designed for easy coastal living and effortless entertaining. The living, dining, and kitchen areas flow seamlessly together, creating a welcoming gathering space filled with natural light and breezy island ambiance. Whether enjoying a quiet morning coffee or hosting friends after a day at Anna Maria’s beautiful beaches, the layout makes the home feel both spacious and intimate. A convenient indoor laundry room is thoughtfully tucked away, adding modern practicality to this historic retreat. The home features a well-designed split floor plan, offering privacy and comfort for residents and guests alike. The primary bedroom suite includes a private ensuite bath, creating a peaceful retreat at the end of the day. On the opposite side of the home, the second bedroom features charming built-in bunks, perfect for family or visiting guests, with easy access to the second full bath. Step outside to discover a beautifully landscaped private pool enclosure, surrounded by lush tropical greenery that creates a tranquil island oasis. It’s the perfect spot to relax, unwind, and soak in the peaceful rhythm of Anna Maria’s laid-back island lifestyle. All of this is located just two blocks from Anna Maria’s world-famous sugar-sand beaches, and only moments from the island’s beloved restaurants, charming boutiques, and local shops. Spend your days biking to breakfast cafés, strolling to dinner with sunset views, or exploring the unique coastal storefronts that make Anna Maria so special. This lovingly restored cottage offers a rare opportunity to own a piece of historic island charm paired with modern comfort in one of Florida’s most treasured beach communities.

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Becky Sirigotis (941-201-8000)

Remarks: Discover the epitome of coastal sophistication with this exquisite British West Indies waterfront residence, perfectly nestled on Anna Maria Island. Spanning over 5,000 square feet, this luxurious home is designed for those who love to entertain and indulge in the finer things in life. Step inside to find two lavish primary suites, an elevator, and multiple terraces that offer breathtaking views. The entertainment options are endless with a stylish media room featuring a beverage center, ideal for movie nights or hosting friends. Every corner of this home exudes elegance, from the solid wood cabinetry and custom millwork to the stunning hardwood and travertine flooring. The open floor plan seamlessly connects to an eat-in kitchen, boasting a large central island, double oven, butler’s pantry, and granite surfaces, making it a chef’s paradise. For more formal gatherings, the separate dining room sets the perfect scene. An office or den is conveniently located on the main level, offering a quiet retreat for work or relaxation. Two additional bedrooms share a spacious bathroom complete with a walk-in shower, ensuring comfort for family or guests. Outdoors, the multiple living areas provide serene views of the canal and Bimini Bay, with direct access to the Intracoastal waterway. The lavish outdoor amenities include a saltwater pool with a sun shelf and spa, and a 70-foot dock equipped with a 13,000-pound boat lift, perfect for boating enthusiasts. Entertain in style on the expansive covered lanai, featuring an outdoor kitchen and ample space for gatherings. Additional features such as plantation shutters, a state-of-the-art security system, oversized closets, and a 3-plus car garage enhance the allure of this property. Don’t miss your chance to own this stunning waterfront retreat. Call today for your private viewing and step into a lifestyle of unparalleled luxury.

Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)

Listing Agent: Gregg Bayer (941-799-9096)

Remarks: Beautifully renovated two-bedroom, two-bathroom condo short distance to the beach. Everything in the condo is brand new, from the furnishings and kitchen appliances to the decorations on the walls. Kitchen with updated cabinets with soft close and solid granite countertops. Island with plenty of seating for entertaining. Sold as is with all brand new high-end furniture, flat-screen TVs with roku for unlimited entertainment options. It's ready for you to pack your bags and move in, or you can start renting it out and begin making money right away. This condo features a lovely semi-private courtyard that is perfect for entertaining guests at a dinner party or relaxing with a coffee in the morning. There is also a shared pool with a rock waterfall and plenty of space to lay out and soak up the sun. The property is currently a vacation rental with a proven rental history. The landscaping has been cleaned up and is ready for any personal touches you would like to add. The photos in MLS are from before the storms and do not reflect the changes that have been made. Furnishings, appliances, etc. have been replaced and are brand new. Due to property bookings the photos will be scheduled at a later date *** Price adjustment*** Major price drop recently made ** Buyers are motivated to sell** Bring your buyers on over and make an offer ***

Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)

Listing Agent: Jennifer Chatt (941-465-0045)

Remarks: Welcome to an extraordinary waterfront retreat on beautiful Anna Maria Island featuring over 100 feet of deep-water canal frontage, private dockage, direct Gulf access with no bridges, and the rare advantage of weekly rentals allowed, making it an exceptional investment opportunity. Fully reimagined by Eason Builder Group, this stunning 3-bedroom, 3.5-bath coastal residence blends elevated luxury craftsmanship with effortless island living — offering exceptional boating access, resort-style outdoor spaces, walkability to the beach, and outstanding income-producing potential. From the moment you arrive, lush tropical landscaping and timeless coastal architecture create an immediate sense of relaxed sophistication. Inside, every detail has been thoughtfully curated with custom millwork, wood coffered ceilings, wide-plank flooring, designer lighting, layered textures, upscale furnishings, and beautifully integrated indoor-outdoor living spaces. The open-concept floor plan centers around a spectacular chef’s kitchen featuring premium appliances, quartz countertops, custom cabinetry, designer tilework, statement pendants, and a handcrafted wood-accent range hood. Each bedroom feels like a private boutique retreat, including a custom-designed bunk room ideal for hosting guests and maximizing luxury vacation rental appeal. Spa-inspired bathrooms showcase elevated tile selections, custom vanities, and refined coastal finishes throughout. Outside, the home transforms into a true private island resort with a spectacular pool and spa, expansive sun deck, tropical landscaping, multiple lounge areas, outdoor dining spaces, and a fully equipped summer kitchen designed for unforgettable entertaining. For boating enthusiasts, the private dock provides effortless access for boats, paddleboards, kayaks, and jet skis — perfect for exploring nearby sandbars, waterfront restaurants, and the turquoise Gulf waters. Located moments from Anna Maria Island’s famous white sand beaches, Pine Avenue boutiques, cafés, and waterfront dining, this exceptional furnished property is perfectly suited as a luxury primary residence, island getaway, or high-performing vacation rental investment offering the ultimate island lifestyle.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)

Listing Agent: Christy Travis (941-545-5284)

Remarks: Your dream view, just got a dream price! Luxury 5 Bedroom Waterfront + Dock | 3-Min Walk to Beach -Exceptional waterfront retreat perfectly positioned in the heart of Anna Maria Island. Just a three-minute stroll to the soft sugar sands of Manatee Beach, this stunning five-bedroom, three-and-a-half-bath residence delivers coastal luxury at every turn—complete with a private dock with ladder where manatees often glide by, a heated pool and spa, and a show-stopping rooftop deck with Gulf and Bay views. Designed for unforgettable gatherings, Coral Castle seamlessly blends upscale comfort with relaxed island charm! Outdoor Living at Its Finest, the rooftop deck is the crown jewel of Coral Castle—offering breathtaking sunrise and sunset views over both the Gulf and Bay. Start your mornings with coffee and ocean breezes or unwind in the evening with a cocktail as the sky glows in brilliant island hues. The tropical backyard is a private sanctuary featuring a heated pool, spa, lounge seating, and outdoor grill, perfect for post-beach relaxation or entertaining under the stars. From the private dock, enjoy peaceful water views—and keep watch for friendly manatees passing by, an unforgettable hallmark of island living. Stylish Interiors Made for Comfort-Step inside to a bright, open-concept living space filled with natural light and coastal elegance. The living room offers plush seating, a flat-screen TV, and sliding glass doors that open directly to the outdoor patio—blurring the line between indoor and outdoor living. The chef-inspired kitchen is fully equipped with stainless steel appliances, generous counter space, and a wine fridge, making meal prep effortless. Gather inside at the dining table or dine alfresco beneath the covered patio for a true island experience. Sleep in Luxury- Primary Suite: King bed, private balcony, vaulted shiplap ceiling, walk-in closet, spa-style ensuite with soaking tub and walk-in shower; Second Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Third Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Fourth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo; and Fifth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo. Prime Island Location- Enjoy peaceful mornings fishing from the dock or take a short drive to Pine Avenue and Bridge Street, where you’ll discover charming boutiques, local dining, and island favorites. Whether your days are spent boating, lounging by the pool, or soaking in rooftop views, Coral Castle delivers the perfect balance of relaxation and adventure. Every detail is designed to create lasting memories—from manatee sightings to sunset cocktails on the rooftop. This is more than a stay—it’s a true Anna Maria Island experience. Currently operating as a vacation rental with solid history and a strong start to 2026—ideal personal-use + income opportunity.

Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)

Listing Agent: Shauna Ruby (941-544-2070)

Remarks: Fantastic Vacation Rental Loved By All Generations Welcome to the ultimate island vacation home. Located in a weekly rental zone, it is positioned to be an outstanding income producing property with strong vacation rental history and bookings secured into Summer 2026, making it an exceptional investment opportunity for any buyer. This fully renovated ground level retreat is designed for effortless living, easy accessibility, and unforgettable stays. Families and guests of all ages love the spacious layout and the simple walk to the beach. Just a quick two minute stroll to soft sand and nightly sunsets, this home delivers everything families want in a perfect Anna Maria Island getaway. Beautifully renovated in 2025 inside and out, this 3-bedroom, 2 bath home offers 1,777 square feet of fresh modern style on a generous 7,022 square foot lot. Every key system has been updated for comfort and peace of mind including new drywall, insulation, AC ductwork, water heater, high impact windows, and a 2023 metal roof. The new kitchen features stylish cabinetry and brand-new appliances. Both bathrooms have been refreshed with new vanities and finishes, and the home includes a new washer and dryer with custom laundry cabinetry. Step outside to your private oasis with a heated pool powered by a new pool heater, lush new landscaping, updated irrigation, and plenty of space to relax in the sun. The large garage is ideal for beach gear, bikes, a golf cart, or a fun game area for guests. The home is being sold fully turnkey furnished with all new furniture and décor so it is ready to drop your bags and enjoy from day one. This is a rare opportunity to own a fully updated, high performing, guest friendly vacation rental on Anna Maria Island. A home that generations can enjoy together. A home that renters will return to year after year. Your slice of paradise is ready. Don't wait, call for your private showing today and start enjoying island life.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Kathy Harman (941-900-9828)

Remarks: Welcome to this charming 2 bedroom, 2 bath beach house in Holmes Beach on the highly desirable Anna Maria Island. Perfect for someone looking for a private residence, a vacation getaway or an investment opportunity. This popular vacation rental, that enjoys many repeat guests each year, comes FULLY FURNISHED & TURN-KEY READY including the recreational equipment! As you walk up the stairs to the front deck, you will see a gas grill and lovely table for delightful Al Fresco dining! When you enter the large living room, you immediately sense the casual elegance and cheerful, natural lighting. The dining room sliders open to the spacious private screened deck.The fully equipped kitchen has granite countertops with ample space for easy meal prep. Upstairs, you will find 2 bedrooms and a hall bath. The living room includes a sleeper sofa with a Posturepedic mattress for extra sleeping space. Downstairs, you will find a large game room, laundry room (with new washer and dryer) and a 2nd full bathroom. Through the laundry room, you will find the lower back deck with a gas firepit which is ideal at night under the stars. Immerse yourself in the island's natural beauty with a short walk to the beach or hop on the nearby trolley for effortless island exploration. Drop your kayak in the nearby canal that leads to Bimini Bay and you may encounter dolphins and manatees as you paddle along! As you unwind from the day, you may want to walk to the beach to enjoy Anna Maria Island's world class sunsets. This beach house has been lovingly cared for and meticulously maintained. Roof (2021) A/C (2017) and serviced regularly. DishWasher (2023) Water heater (2017) Washer/Dryer (2024). Experience the unique charm of Anna Maria Island. Don't miss out on this incredible opportunity! Call today for your private showing!

Listing is courtesy of: SIGNATURE REALTY ASSOCIATES (813-689-3115)

Listing Agent: Liz Young (813-787-1386)

Remarks: Come make your island dream a reality! This updated 3 bed/2 bath coastal charmer is just steps to the sugar sand beach, with a heated, salt water pool with full spa features! Create your own style in this cute cottage, where the hard work has already been done for you! New Luxury Vinyl Plank throughout, fresh paint, new doors, new bathrooms, new cabinetry and new appliances, means nothing left for you to do but add your personal styling! Bring your coastal creativity and create the perfect décor for you! You will love the ease of relaxing in your open family room and cooking in your updated kitchen with breakfast bar! With 3 bedrooms and a split floor plan, you have room for guests while enjoying the privacy of your own en suite. Make this your full time island escape or enjoy the benefit of income from the short term rentals that are allowed on this quiet street just steps to the soft sand of the Gulf beach! Priced to move, so you can make it your own, this one is ready to make your beach house dream come true!

Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)

Listing Agent: Erin Leathem (941-448-5616)

Remarks: Located in the heart of Holmes Beach on Anna Maria Island, this reimagined waterfront home offers deep-water boating access, direct Gulf views, elevator access, and a beach location that is hard to beat, just steps from the front door to the sand. Set on one of the closest canal-front streets to the beach, the property provides protected dockage, quick access to Tampa Bay, downtown St. Petersburg, and the Gulf of Mexico, along with the everyday ease of true island living. Originally rebuilt from the block in 2022 in collaboration with Richard Haas, the home was thoughtfully redesigned with clean architectural lines, quality coastal construction, and low-maintenance ownership in mind. The result is a modern Anna Maria Island waterfront residence built for comfort, efficiency, and long-term durability without sacrificing style, function, or quality. Inside, the living spaces were designed to maximize natural light and keep water views connected to daily life. The main living area, kitchen, and secondary primary suite all capture direct Gulf views, while large glass openings connect the interior spaces to the outdoor terraces. A custom floating red oak staircase serves as a striking architectural focal point and adds warmth to the clean modern design. The kitchen was designed for both entertaining and everyday use, featuring Cosentino Quartz counters, custom full-height cabinetry, JennAir Professional appliances, and a walk-in pantry. More than fifteen slabs of quartz were incorporated throughout the kitchen and bedroom suites, creating a consistent level of finish throughout the home. Smart-home features, remote-controlled shades, custom lighting, elevator access, and thoughtfully curated finishes contribute to a comfortable and efficient living environment. A newly installed dock and Golden boat lift accommodate larger vessels, while recent dredging improves canal access for serious boaters. A pool package is in permitting, allowing the next owner to create a custom outdoor living space without navigating the island's permitting process from the beginning. The primary suite offers a private retreat with a custom-built walk-in closet and a spa-inspired bath featuring Toto fixtures, dual vanities, and multi-function shower features. Additional upgrades include dual high-efficiency HVAC systems, buried gas storage, generator readiness, tankless water heaters, and water-softening systems. Combining modern coastal architecture, deep-water boating access, Gulf views, updated construction, and one of the most walkable beach locations on Anna Maria Island, this Holmes Beach waterfront residence represents a rare opportunity within Florida's luxury coastal market. Easy access to North bridge/Manatee Ave via two different routes. Note: Pool is AI generated and is not present on the property, however permit is in final stages and pool is included in the price.

Listing is courtesy of: COLDWELL BANKER REALTY (813-286-6563)

Listing Agent: Jennifer Zales (813-758-3443)

Remarks: Short Sale. Live a life you don't need a vacation from in this beautifully updated, turnkey-furnished beach villa just STEPS from the sugar-sand beaches of the Gulf. Located on the desirable west side of Holmes Beach, this charming 2-bedroom, 1.5-bath townhouse offers approximately 1,050 sq ft of coastal living with no major roads to cross on your way to the beach. Recently renovated, this home features a stunning new kitchen completed in 2025 with custom cabinetry, granite countertops, and state-of-the-art stainless-steel appliances. Fresh interior paint, new tile flooring throughout, and hardwood stairs create a clean, modern feel with no carpeting to maintain. Additional updates include a NEW ROOF IN 2024 & an A/C SYSTEM INSTALLED IN 2020. Enjoy your morning coffee in the inviting front seating area or unwind in the private fenced courtyard, perfect for grilling, entertaining, or relaxing after a day at the beach. With no condo fees, excellent rental potential, and a prime location just moments from shopping, dining, and everything Holmes Beach has to offer, this property presents an exceptional opportunity as a vacation getaway, investment property, or year-round residence. *** SELLER offering $10,000 credit towards closing costs on an agreed upon contract.

Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)

Listing Agent: Christine Spelman (941-713-3501)

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)

Remarks: Under contract-accepting backup offers. Wake up to sweeping views of the Gulf of Mexico from this beautifully maintained two-bedroom, two-bath condo in Sun Plaza West. I direct Gulf front complex on Anna Maria Island. Filled with natural light, this home offers comfortable and inviting coastal living, featuring ceramic tile flooring throughout, Cambria granite countertops, Jen-Air appliances, PGT impact windows, and Hunter Douglas blinds that enhance both style and function. Thoughtfully placed dimmer switches create a warm, customizable ambiance, while beautiful Gulf views can be enjoyed year-round from the living spaces and bedrooms. The condo comes fully furnished, making it truly move-in ready and ideal for immediate enjoyment or rental use. Enjoy coffee in the morning off the cozy balcony off the master or enjoy happy hour on the amazing beaches of the Anna Maria. The home was completely renovated recently, offering all new electrical and plumbing throughout. Enjoy the ease of laundry inside the home for easy cleaning, as well as updated finishes and a well-designed layout that balances comfort and functionality. Recent upgrades provide added peace of mind, including a brand-new air conditioning system installed in 2023 and a new hot water heater in 2024. Residents enjoy a variety of desirable community amenities, including a sparkling pool, tennis court, and pickleball court—perfect for both relaxation and an active lifestyle. A private 8x10 storage unit, offering ample space for beach gear, bikes, or seasonal items. Whether you’re seeking a full-time residence, a vacation retreat, or an investment opportunity, this Gulf-view condo offers an exceptional combination of comfort, quality finishes, thoughtful updates, and coastal scenery in a sought-after setting. This is the perfect home for living the Anna Maria Life!

Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)

Listing Agent: Billi Gartman (941-545-8877)

Remarks: GULF FRONT - Spacious and Beautifully Maintained and Renovated 1 Bedroom/1 Bath Condo in the Heart of Holmes Beach. Breathtaking Gulf Views to behold from every room. The kitchen, windows and sliding doors have been updated and the AC was replaced in 2025. This unit features a covered, open balcony allowing for your own Private Outdoor Space while relishing in the balmy Gulf breezes. Commodious Open living/dining area is painted in calm, neutral colors and ceramic tile flows throughout. The bedroom features full gulf views, a large walk-in closet and ensuite bath with separate vanity area and combination tub/shower. The updated kitchen provides plentiful and aesthetic cabinetry, a closet pantry, newer appliances, desk area and Washer and Dryer. Martinique South offers a Gulf side pool, tennis/pickle ball courts, an elevator, secure entrance, large Community living space with full Gulf Views, a complete kitchen, bathrooms, and outdoor covered patio. The Community Room is ideal for parties and large gatherings. Pride of ownership shines in this community where friends are neighbors and neighbors are friends. This lovely unit is offered turn-key furnished, with room for your personal touches as well as a carport and storage room. Located within walking distance of Holmes Beach amenities. Magnificent sunsets, strolls along the white sand beach, passing dolphins, the cry of the seabirds and the comforting sound of the surf await...

Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)

Listing Agent: Adele Holland (941-587-6328)

Remarks: 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!

Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)

Listing Agent: Shauna Ruby (941-544-2070)

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)

Remarks: Experience elevated coastal living in the exclusive North Point Harbor community of Holmes Beach, located on the highly desirable northern end of Anna Maria Island. This impeccably maintained custom waterfront estate spans approximately 3,640 square feet and offers direct deep-water access to both the Gulf of Mexico and Tampa Bay from the peaceful shores of Key Royale. Designed with both luxury and functionality in mind, the home features 5 bedrooms, a versatile bonus room, and 6 bathrooms (4 full and 2 half), showcasing timeless craftsmanship and a spacious, thoughtfully designed layout. Built for lasting quality and refined coastal style, the residence features a durable metal roof, elegant vinyl wood and tile flooring throughout the open living spaces, and two expansive balconies perfectly positioned to capture stunning panoramic water views from nearly every angle. Seller financing may be available, subject to terms. For boating enthusiasts, the private dock and dedicated boat slip offer effortless, no-bridge access to open Gulf waters and the renowned fishing grounds surrounding Egmont Key — ideal for accommodating a yacht or sportfishing vessel. Beyond the home itself, enjoy the unmatched lifestyle of Anna Maria Island, celebrated for its charming “Old Florida” atmosphere and strict building limitations that preserve breathtaking views and laid-back island character. This golf-cart-friendly community offers easy access to pristine Gulf beaches, boutique shopping, and exceptional dining along Pine Avenue and Gulf Drive. Key Royale is especially sought after for its quiet, tucked-away setting, private golf club, and serene waterfront surroundings, while North Point Harbor residents also enjoy beautifully maintained grounds and private tennis courts. Conveniently located just a short drive or boat ride from both Sarasota and St. Petersburg, this property offers the perfect balance of peaceful island living and access to vibrant cultural destinations. Meticulously cared for with no flood damage history, the home is truly move-in ready and maintained to exceptional standards. Whether entertaining from the chef-inspired kitchen, relaxing on the screened lanai overlooking the pool, or setting out for a sunset cruise from your private dock, this extraordinary property delivers the ultimate blend of coastal sophistication, resort-style comfort, and enduring quality. From its resilient construction to its artisan finishes, every detail has been carefully curated to create a premier waterfront retreat in one of Florida’s most coveted island destinations. Embrace the Anna Maria Island lifestyle — where every sunset feels unforgettable and the water is always just steps away.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Robert Johnson (813-364-2250)

Remarks: BEACHY KEEN… Just steps from the pristine shores of Anna Maria Island, this exceptional townhome is ideal as a weekend escape, a seasonal retreat from Old Man Winter, or a smart investment while retirement plans are still taking shape. Whether you’re tired of renting, dreaming of a coastal getaway, or looking to diversify with Florida real estate, this property checks all the boxes. Inside, you’ll find an updated kitchen designed to delight the family chef, featuring newer stainless-steel appliances, rich granite countertops, and classic shaker cabinetry. Stunning Brazilian rosewood flooring flows throughout the open, inviting floor plan, complemented by a dedicated dining area perfect for relaxed gatherings. A conveniently located first-floor powder room offers added convenience for guests. The expansive lanai off the living area is ideal for outdoor entertaining and provides easy access to the community pool. Upstairs, two spacious ensuite bedrooms each feature a private bath and their own balcony—perfect for morning coffee or unwinding at the end of the day. A two-car garage offers ample space for vehicles and other island essentials. Located less than 500 yards from the Gulf, your new home away from home invites daily beach walks, refreshing coastal breezes, and spectacular sunsets. Enjoy the island’s charming shops, restaurants, and community amenities including tennis, pickleball, and a baseball field. Come for the weekend, stay for the season, or plan for the future—either way, you’ll be glad you made this move.

Listing is courtesy of: FINE PROPERTIES (941-782-0000)

Listing Agent: Richard Capps (941-920-7500)

Remarks: Welcome to "Captains Quarters" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $125k in rental revenue in 2025. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

Listing is courtesy of: PINEYWOODS REALTY LLC (813-225-1890)

Listing Agent: Amanda Cornett (941-807-2811)

Remarks: Under contract-accepting backup offers. NEW PRICE! BRING YOUR BUYERS! This is a ONE OF A KIND - ELEVATED home with a PRIVATE POOL & your own garage, this is like single family home living - for under $1m on Anna Maria Island! This updated 2 bed/2 bath picture perfect, island dream is ideally situated on a quiet corner, just two short blocks from the Gulf Beaches! This UPDATED island sanctuary surrounds you in coastal charm. The luxury vinyl large plank flooring throughout is ideal for beach living, and ties the open living and dining room together. The fully renovated kitchen with quartz counters, is equipped with stainless steel appliances and ample shaker style white cabinetry. Your guests will enjoy their private accommodations just next to their updated full bath with white subway tile surround and new vanity with Moen faucet. Upstairs you will relish the privacy of your primary retreat. The sunlight brightens your spacious room that includes a large walk in closet. Your en suite bath has a glass enclosed shower, with tile bench and pebble stone shower flooring. And outdoors, you can relax on your front porch, or cool off in YOUR VERY OWN pool! Embrace the island life in this lovely land condo, and use it as a short term rental when you are away. THERE IS NOTHING LIKE IT at this price - come make it your own today!

Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)

Listing Agent: Erin Leathem (941-448-5616)

Remarks: This oversized lot features an expansive seawall, a brand-new dock, and a 16,000-pound boat lift, offering endless possibilities to build your custom dream home or renovate the existing residence to fit your lifestyle. Enjoy the outdoor Florida lifestyle with a large built-in pool and spa, complete with a new heater. Situated on one of the widest canals in Holmes Beach, this property provides easy boating access through Bimini Bay and directly out to the open waters of the Bay. A rare waterfront gem that truly must be seen to be appreciated!

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Charles Buky (941-228-6086)