Location: Holmes Beach , 34217
Do Not Show Listings
309 57TH ST, HOLMES BEACH, FL 34217
$999,999103 Days on yellowkey MLS ID: A4685855
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1982 Built: 1979 Tax: $4,508 (2025)Community: Holmes Beach 13Th UnitSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,508
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Discover this 4 bedroom, 3 bathroom versatile home, perfectly positioned on Anna Maria Island for effortless coastal living. Located on a spacious 0.23-acre lot (approximately 9,988 sq ft), this property offers many possibilities!! If desired, this home can easily be changed back to a duplex with some modifications making it a 3 bedroom, 2 bathroom unit on one side and a cozy mother in law suite that is 1 bedroom, 1 bathroom unit on the other. Whether you're seeking a multi-generational home, a vacation retreat with rental potential, or an income-generating investment, this setup provides flexibility and charm in one of Florida's most desirable beach communities. Ideal for families or entertaining, featuring ample room for comfortable island-style living. Step outside to a backyard with plenty of space to add your dream pool, creating a private oasis for relaxation under the Florida sun. Or keep the awesome Koi pond and zen feels of the backyard. With its prime location, you're just a short stroll from pristine white-sand beaches and gorgeous sunsets. Walking distance to Holmes Beach restaurants and shops. Schedule a showing today!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Barbara Sato (941-778-7200)
6005 GULF DR #219, HOLMES BEACH, FL 34217
$695,00067 Days on yellowkey MLS ID: A4689996
REDUCED by $5,000 (0.7%) on 05/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1011 Built: 1980 Tax: $7,704 (2025)Community: Playa EncantadaSpa: YesCondo
Taxes:$7,704
Remarks: Enjoy coastal living at Playa Encantada on Anna Maria Island, where short-term rentals are permitted! This beautifully maintained second-floor condo features 2 bedrooms and 2 bathrooms and comes fully furnished, making it truly move-in ready. Located in one of the island’s most sought-after beachfront communities, residents enjoy a wide range of amenities including private beach access, a heated swimming pool, spa, tennis and pickleball courts, shuffleboard, elevator access, covered parking, and convenient beach entry just across the street. The unit offers desirable southern exposure with views overlooking the tennis courts. Inside, you’ll find a beautifully remodeled kitchen with elegant quartz countertops, stainless steel appliances, including a spacious double oven and an open-concept layout ideal for entertaining. The primary suite features a generous walk-in closet and a beautifully updated bathroom with a walk-in shower. Crown molding and tile flooring throughout add a refined touch. Additional highlights include an in-unit washer and dryer, a tankless water heater, stainless appliances installed in 2023 and an A/C system installed in 2021. Step out onto the large covered lanai to enjoy Florida’s lush scenery and stunning skies. A private owner’s storage room along with a dedicated parking spot is also included on the ground level. With a two-week minimum rental policy, this property offers excellent potential as an income-producing investment or a relaxing second home. Experience the best of the Florida lifestyle, including convenient private beach access with limited public entry nearby for added privacy. The condo is ideally located near a trolley stop, offering free and easy transportation to nearby restaurants and shops. Call for your private showing today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Hannah Hillyard (941-744-7358)
7324 GULF DR #12, HOLMES BEACH, FL 34217
$2,349,000357 Days on yellowkey MLS ID: A4657719
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2046 Built: 2005Monthly Fee: $1,928 Tax: $15,107 (2025)Community: La Casa Costiera Ph 1Spa: YesCondo
Taxes:$15,107
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
Remarks: RARE AND FABULOUS GULF FRONT 3B/2.5B LUXURY CONDO AT LA CASA COSTIERA W/ 2300 SQ. FT. La Casa Costiera allows for weekly rentals and has EVERYTHING you could want for in a beach condo on Anna Maria Island! 3RD LEVEL END UNIT with partial Gulf of Mexico views, semi-private ELEVATOR comes to your front door, TURN KEY FURNISHED, 2 car covered secure and reserved garage parking spaces, beach storage closet, private beach access, heated pool, an in-ground spa, a picnic area with a gas grill, a charcoal grill, outdoor fireplace and owners are allowed to have 2 large pets! The condominium built in 2005 by Brent Whitehead Construction has a beautiful exterior that fuses Italian Tuscan and Spanish Mediterranean style on the powdery-white sands of the Gulf of Mexico. This spacious, light-filled condominium has an elegant owner's suite with grand entry, plus two other very generously sized and appointed guest rooms. The wet bar with wine cooler and the electric fireplace along with the high ceilings complete with crown moldings and Andersen Impact doors and windows with custom window treatments and plantation shutters adds to the wonderful luxury beachfront atmosphere. Sliders open to Gulf breezes on the large balcony with beach views and perfect for dining or relaxing. Amazing Holmes Beach location, and the free AMI trolley stops out front! Whether you're looking for a vacation home, an investment property, or a place to call your own, this Condo offers a perfect blend of luxury, comfort and convenience.
Listing Agent: Cindy Quinn, Pa (941-780-8000)
3303 6TH AVE #B, HOLMES BEACH, FL 34217
$695,00012 Days on yellowkey MLS ID: A4696837
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 800 Built: 1978 Tax: $13,310 (2025)Community: CasanasHalf Duplex
Taxes:$13,310
Remarks: Welcome to your dream coastal getaway! As captured in the stunning aerial view, this charming two-bedroom, two-bathroom half duplex boasts a prime location less than two blocks from the white sands of Anna Maria and local shops. The property is purposefully elevated for peace of mind, providing the added benefit of ample ground-level storage and covered parking underneath. Zoned for weekly rentals, this home offers incredible flexibility as a versatile island retreat or a highly desirable vacation destination. Inside, the bright and airy kitchen is beautifully appointed with crisp white cabinetry, gleaming countertops, a breakfast bar with vibrant seating, and modern stainless steel appliances, including a premium gas range for effortless cooking. The coastal aesthetic continues into the restful bedrooms, highlighting a spacious setup complete with low-maintenance tile flooring and large windows that invite plenty of natural light. Whether you are looking for a personal slice of paradise or a flexible property in an unbeatable location, this beachside gem is ready to welcome you home.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Joey Hutchinson (941-518-5585)
616 FOXWORTH LN, HOLMES BEACH, FL 34217
$2,095,000162 Days on yellowkey MLS ID: A4677576
REDUCED by $55,000 (2.6%) on 05/14/2026
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2350 Built: 1971Monthly Fee: $8 Tax: $12,552 (2025)Community: Key Royale 13Th AddSpa: NoSingle Family
Taxes:$12,552
Remarks: Step into effortless luxury with this meticulously renovated canal-front retreat, ideally located on 100 feet of waterfront, on an 11,543 sq ft lot in the heart of the Key Royale community. Designed for relaxed coastal living, this beautifully updated 3-bedroom, 3.5-bath home offers the perfect blend of style, comfort, and waterfront lifestyle. The home has a chef-inspired kitchen featuring wood cabinetry, quartz countertops, a gas range, wall oven, wet bar with wine refrigerator, and a generous center island perfectly suited for both everyday living and elegant entertaining. Walls of sliding glass doors bathe the interior in natural light and open to a private outdoor oasis, creating a seamless indoor-outdoor flow. Two of the bedrooms have private ensuite baths, including the primary bedroom which features a spacious bedroom with an en-suite bath with a soaking tub, a walk-in shower and an outdoor shower providing comfort and privacy. Outside, enjoy the resort-style pool designed for lounging in both sun and shade, or take in peaceful canal views framed by lush tropical landscaping. A new irrigation system and new elegant landscape lighting have also been installed. A true boater’s dream, the property features a private dock with electric and water, plus a 10,000 lb boat lift and kayak launch, offering quick access to the sparkling waters of Bimini Bay, Tampa Bay and beyond. Additional updates include a roof installed in 2017 for added peace of mind. Just a short stroll or bike ride from Anna Maria Island’s sugary beaches and moments from charming shops, dining, and island attractions; the location is as exceptional as the home itself. Residents of Key Royale have the option to join the private Key Royale Club, a 9-hole golf course with a clubhouse, creating a lifestyle that perfectly balances boating, golf, and island leisure. Bring your boat, fishing poles, golf cart, and clubs and start living the island lifestyle you’ve been dreaming of. This is a rare opportunity to own a truly special slice of waterfront paradise.
4255 GULF DR #116, HOLMES BEACH, FL 34217
$589,000355 Days on yellowkey MLS ID: A4657522
REDUCED by $10,000 (1.7%) on 05/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1430 Built: 1981Monthly Fee: $1,040 Tax: $2,906 (2025)Community: Island VillageSpa: NoCondo
Taxes:$2,906
Remarks: Virtually Staged. Virtually Staged. NEW ROOF installed in 2025! Welcome to this freshly remodeled, elevated 2-bedroom, 2-bathroom end-unit condo with a flex room at Island Village in Holmes Beach. Perfectly located just one block from the pristine sands of Anna Maria Island. This bright and airy condo has been thoughtfully updated, featuring a clean, modern aesthetic. It includes two dedicated parking spaces under building and includes a storage room. The interior has been freshly painted and new tile floors installed in the kitchen and flex room. One of the standout upgrades is the enclosed flex room, now fully under air with the recent extension of the A/C system. This versatile bonus room serves as a wonderful flex space, featuring a large closet and offering endless possibilities for use. Use it as a bright and inviting sunroom filled with natural light, a comfortable home office that inspires productivity, or a cozy retreat that effortlessly adapts to your lifestyle needs. This sun-filled retreat is enhanced with sliding glass doors and Phifer weave sunscreen shades, offering views of the lush, park-like surroundings. The kitchen is designed with both style and functionality in mind, featuring durable Corian countertops, a breakfast bar, a Whirlpool full-size stainless-steel refrigerator and freezer, and custom Kitchen Craftmade Cabinetry. The primary bedroom includes sliding glass doors that open to the air-conditioned flex room, a large walk-in closet, and an en-suite bathroom with a walk-in shower. The second bedroom offers another ensuite bath, making it ideal for guests or family members. A dedicated laundry room with a full-size washer and dryer adds everyday convenience. Recent updates include a NEW ROOF in 2025, an upgraded electric meter in 2024, and refreshed exterior paint completed in 2021. The condo also includes an osmosis water filtration system. This condo is part of Island Village condominiums, a well-maintained, maintenance-free community where the HOA covers cable TV, internet, water, sewer, trash, insurance, and upkeep of the grounds, exterior, community pools, and tennis courts. Residents enjoy access to two heated pools and two tennis/pickleball courts, offering ample recreational opportunities year-round, and owners are permitted to rent their condo up to three times yearly, with a minimum rental period of one month. Located only two blocks to direct beach access, this condo is ideally positioned within easy access to over 20 public beach access points, 12 parks, popular restaurants, and local shops. Don’t miss this rare opportunity to own a beautifully updated condo in one of Anna Maria Island’s most desirable communities. Schedule your tour today and experience the relaxed, tropical lifestyle of Island Village. Be sure and check out the 3D walkthrough and floor plan for this lovely condo in Island Village.
462 63RD ST, HOLMES BEACH, FL 34217
$750,000190 Days on yellowkey MLS ID: A4674852
2 Days Off yellowkey (back on 5/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1356 Built: 1972Monthly Fee: $150 Tax: $9,733 (2025)Community: Seaside Gardens RepVilla
Taxes:$9,733
Remarks: Under contract-accepting backup offers. Tucked away in the waterfront community of Seaside Gardens, this fully remodeled coastal home offers a bright, modern interior paired with the kind of peace of mind that’s hard to come by thanks to thoughtful upgrades like Endura flood panels, Endura cabinetry, and durable tile flooring throughout. Designed with both comfort and resilience in mind, the layout features two ensuite bedrooms for ultimate privacy, a skylight that fills the main living space with natural light, and a sleek kitchen outfitted with stainless steel appliances and crisp finishes. A sun-drenched Florida room at the back of the home frames stunning open water views and opens directly to the waterfront deck where your private dock awaits, ideal for boating enthusiasts or simply soaking up the coastal lifestyle. From the backyard and boat dock, enjoy spectacular sunset views that paint the sky each evening. Just steps away, you'll find a community park, tennis courts, pickleball courts, and a dog park, adding even more to the lifestyle appeal. There’s also a detached storage shed for your bikes, beach chairs, or tools. Located in a weekly vacation rental zone, this home is not only a tranquil retreat but also a strong investment opportunity just minutes from Anna Maria Island’s sugar sand beaches and a short walk to charming shops and local dining favorites.
Listing Agent: Darcie Duncan (941-779-0304)
2915 AVENUE C, HOLMES BEACH, FL 34217
$1,094,000228 Days on yellowkey MLS ID: A4668577
REDUCED by $30,500 (2.7%) on 06/11/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1040 Built: 1979 Tax: $12,026 (2024)Community: IlexhurstSpa: YesSingle Family
Taxes:$12,026
Tax Year: 2024
Remarks: PRIME LOCATION | BRAND NEW RENOVATIONS | ELEVATED-LUXURY-LIVING | ELEVATOR | FENCED SALTWATER POOL | MOVE-IN READY | Located on a peaceful street and embraced by the natural beauty of a mangrove preserve, this elevated coastal residence delivers privacy, modern luxury, and a coveted Holmes Beach lifestyle. Thoughtfully renovated over seven months between 2023 and 2024 with the owners investing $275,000 in premium renovations and high-end additions, the home blends timeless design with state-of-the-art upgrades—creating a tranquil retreat just moments from award-winning Gulf beaches, local dining, and island conveniences. Inside, sunlit living spaces showcase elegant finishes and open-concept design. The kitchen is a modern showpiece, featuring sleek granite countertops, white shaker cabinetry, under-cabinet lighting, and a reverse osmosis water system. Two spacious bedrooms and two spa-inspired bathrooms offer comfort and style, complemented by plantation shutters, smooth ceilings, and a whole-home water filtration system. No detail has been overlooked—from new electrical wiring and panel with underground service to a NEW GARAGE DOOR AND OPENER (2025) and a fully accessible 750-LB CAPACITY ELEVATOR for effortless living. Outdoors, a private fenced backyard oasis invites relaxation with a BRAND NEW ELEVATED SALTWATER POOL (2025) surrounded by lush tropical landscaping enhanced with $20,000 in new plantings, including orange trees and lavender bushes. The serene mangrove backdrop ensures rare tranquility, natural beauty, and panoramic views from your bedroom. The lower level includes a TWO-CAR TANDEM GARAGE and an additional 480 SQUARE FOOT BONUS ROOM with durable polyaspartic-coated flooring. Currently serving as a spacious room for entertainment this can easily be turned into a gym or extra office space—plus an outdoor shower and additional storage. Zoned for MONTHLY VACATION RENTALS and already having a strong rental history, this property offers both investment appeal and a luxurious personal retreat. Located minutes from the Manatee Bridge, Bridge Street, and the North End of Anna Maria Island, this Holmes Beach jewel captures the essence of refined coastal island living. Don’t miss your slice of paradise — schedule your private tour today!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Dean Hinterstoisser (941-726-0314)
511 BAYVIEW DR, HOLMES BEACH, FL 34217
$5,140,000173 Days on yellowkey MLS ID: A4675904
REDUCED by $150,000 (2.8%) on 06/05/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3353 Built: 2020 Tax: $24,007 (2024)Community: Sunrise ParkSpa: YesSingle Family
Taxes:$24,007
Remarks: Experience the ultimate island paradise in this practically NEW CONSTRUCTION LUXURY WATERFRONT HOME, thoughtfully designed with solid concrete block construction and cutting-edge design and technology. Spanning over 3,300+ square feet, this stunning residence offers 4 bedrooms and 5 full bathrooms, blending elegance, durability, and effortless coastal living. Perfectly positioned just a few short blocks from the Gulf of America, the home also boasts PANORAMIC Intracoastal waterfront views, creating a rare and breathtaking dual-water lifestyle. The half-elevated design provides peace of mind while enhancing views and architectural appeal. Indoors, no detail has been overlooked. Highlights include a butler’s pantry, an upstairs coffee bar just outside the primary suite, and expansive open-concept living spaces ideal for both everyday comfort and entertaining. The luxurious primary retreat offers a serene escape with spa-inspired finishes and seamless indoor-outdoor flow. Step outside to your private waterfront oasis featuring an infinity pool, hot tub, and a fully equipped outdoor kitchen, all designed to maximize sunset views and coastal breezes. Whether hosting guests or enjoying a quiet evening under the stars, this outdoor space is truly exceptional. With waterfront living, modern luxury, and a premier island location, this home offers everything you could ask for—and more. A rare opportunity to own a refined coastal sanctuary that perfectly balances style, comfort, and location. Schedule your private showing today!
Listing Agent: Shannon O'Brien Kerney (941-737-5153)
6201 HOLMES BLVD, HOLMES BEACH, FL 34217
$1,440,000186 Days on yellowkey MLS ID: A4675506
REDUCED by $10,000 (0.7%) on 05/16/2026
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 1822 Built: 1968 Tax: $9,121 (2025)Community: Holmes Beach 17Th UnitSpa: NoSingle Family
Taxes:$9,121
Remarks: INCREDIBLE VALUE! 5 BEDROOM HOME ON ANNA MARIA ISLAND WITH PROVEN RENTAL HISTORY- THIS IS THE ONE!!! Imagine owning a place where every day feels like a vacation. Located on a peaceful corner lot in the heart of Holmes Beach, this spacious 5-bedroom pool home offers the perfect balance of relaxed island living and modern comfort—just steps from everything that makes this island so special. Designed for connection and comfort, the home features an airy, open layout filled with natural light and coastal character. The kitchen anchors the space with recent updates, stainless steel appliances, and generous prep areas, making it ideal for hosting family and friends after long beach days. Sliding glass doors lead to a private outdoor retreat, where a sun-drenched pool, expansive patio, and side courtyard create a setting made for entertaining, relaxing, and making memories. The primary suite feels like a private escape, complete with an updated bathroom, walk-in closet, and direct access to the pool—perfect for morning swims or quiet evenings outdoors. With five bedrooms accommodating up to 10 guests, the home offers flexibility for full-time living, extended stays, or hosting visitors with ease. Major upgrades add value and peace of mind, including fully renovated bathrooms, updated kitchen features, and a metal roof installed in 2022. The home is thoughtfully maintained and ready to be enjoyed from day one. What truly sets this property apart is the lifestyle. Walk to the sugar-white beaches of the Gulf, bike to local cafés and shops, enjoy sunset strolls, and embrace the easygoing rhythm that makes Anna Maria Island one of Florida’s most beloved coastal communities. Weekly rentals are permitted, providing the option to enjoy the home while also benefiting from its income potential. Whether you’re searching for a beach home, a family getaway, or a smart island investment, this Holmes Beach property delivers space, location, and lifestyle—all in one unforgettable setting. Come experience why people fall in love with Anna Maria Island… and never want to leave.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
95 52ND ST, HOLMES BEACH, FL 34217
$6,900,000121 Days on yellowkey MLS ID: A4680380
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3325 Built: 2003 Tax: $71,226 (2025)Community: Gutierrez RevSpa: YesSingle Family
Taxes:$71,226
Remarks: Views abound in this exquisite beachfront retreat in the heart of Anna Maria Island. This 3-bedroom, 3.5-bath Coastal West Indies–inspired residence showcases exceptional craftsmanship, including custom millwork, solid oak flooring, vaulted ceilings, designer draperies, and Roman shades throughout. An open-concept floor plan fills the home with natural light, while expansive windows and glass doors frame picturesque Gulf views and create seamless indoor-outdoor living—ideal for entertaining. The gourmet kitchen is beautifully appointed with solid wood cabinetry, a paneled refrigerator, custom solid-surface countertops, and a Thermador range. The primary suite is a private sanctuary where you’ll awaken to sweeping views of the turquoise waters of the Gulf. The spa-inspired bath features dual vanities and a luxurious walk-in shower with a striking stone waterfall accent. Hand-carved custom wood doors enhance the suite’s privacy, while a private sitting area just outside provides an additional space to unwind. The third level offers two well-appointed guest suites, each with breathtaking views and elegantly finished en-suite baths.On the lower level, a welcoming foyer with a custom staircase and private elevator provides access to all floors. The oversized two-car garage includes built-in storage cabinetry, and a versatile bonus area offers additional space for entertaining or recreation. Set on a lush half-acre lot with mature landscaping and thoughtfully designed outdoor lighting, the property highlights a stunning beachside pool and spa, covered lanai, private outdoor shower, and roll-down hurricane shutters. Multiple decks provide the perfect vantage point for sunset views and tranquil beach watching.Schedule your private showing today and experience the ultimate in beachfront living.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
6400 FLOTILLA DR #15, HOLMES BEACH, FL 34217
$629,000231 Days on yellowkey MLS ID: TB8439383
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1177 Built: 1978 Tax: $2,337 (2024)Community: Westbay Point & MooringsCondo
Taxes:$2,337
Remarks: Condo on Anna Maria Island, FULLY FURNISHED 2 bed 2 bath, perfectly situated within 1 MILE OF THE BEACH. HIGH AND DRY! Enjoy the breezy GLASSED IN FLORIDA ROOM overlooking the pool or close the sliding glass windows to enjoy the view with air conditioning. Front entrance opens into the shady SCREENED-IN LANAI, LAUNDRY CLOSET is to the left with stackable WASHER/DRYER. Convenient STORAGE CLOSET/WORKSHOP to the right. Original parquet flooring in the foyer. Kitchen has a large pass through opening to the dinning room. Home provides a spacious dwelling area with living/dinning room combo. RECENT UPDATES: ROOF, HVAC, WATER HEATER, and CARPET. Remote controlled ELECTRONIC HURRICANE SHUTTERS for extra protection. Community includes a private BOAT RAMP, BOAT DOCK that doubles as a fishing pier, 2 HEATED POOLS, SPA, TENNIS COURTS, KAYAK/PADDLEBOARD STORAGE and open parking. MAINTENANCE FREE LIVING: CONDO FEE INCLUDES: cable tv, high-speed internet, water, sewer, trash, ground maintenance, exterior maintenance, master insurance, pool, spa and more. Just a 2-minute walk to the CENTRAL PARK which features a DOG PARK, PICKLEBALL COURTS, SKATE PARK, BASKET BALL, BALL PARK, PLAYGROUND and OUT DOOR FITNESS CENTER. Minutes away from sandy beaches and sunshine, the entire island is GOLF CART FRIENDLY, making it easy to explore. Enjoy a cozy atmosphere with local bike shop, restaurants, shopping options, and multiple access points to the beach.
Listing is courtesy of: SANTANA AND COMPANY REAL ESTATE (941-226-9664)
Listing Agent: Ruth Santana (941-226-9664)
3014 GULF DR, HOLMES BEACH, FL 34217
$1,075,000159 Days on yellowkey MLS ID: A4678029
REDUCED by $20,000 (1.8%) on 05/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1320 Built: 1977 Tax: $12,953 (2024)Community: IlexhurstSpa: YesSingle Family
Taxes:$12,953
Remarks: Welcome to "Pineapple Paradise" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $130k 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)
145 50TH ST, HOLMES BEACH, FL 34217
$2,149,000375 Days on yellowkey MLS ID: A4654712
REDUCED by $1,000 (0.0%) on 06/10/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2040 Built: 2008 Tax: $23,038 (2024)Community: Coastal Cottages IiSpa: NoSingle Family
Taxes:$23,038
Remarks: Imagine starting your mornings with a short stroll to the beach to watch the sunrise, spending afternoons in the turquoise Gulf waters, and ending your evenings with spectacular island sunsets! Welcome to island living at its finest, where a dedicated beach access awaits at the end of the street and the best of Anna Maria Island is just moments from your door. This beautiful 4-bedroom, 3.5-bath coastal retreat is perfectly positioned in one of the island’s most desirable locations, offering easy access to the beach, turquoise Gulf waters, local restaurants, boutiques, galleries, and the relaxed charm that makes Anna Maria Island so special. This home offers exceptional flexibility as a private coastal sanctuary, a high-performing weekly vacation rental, or the perfect combination of both. Whether you are seeking a peaceful island escape or a proven investment opportunity, this home delivers unmatched lifestyle appeal and value. Outdoors, a private tropical oasis sets the stage for effortless relaxation and entertaining. Lush landscaping, a heated pool, and multiple outdoor gathering areas invite you to unwind after a day at the beach, lounge poolside beneath the palms, or host family and friends on the covered patio. Inside, the bright open-concept floor plan offers a welcoming coastal feel with spacious living areas, comfortable entertaining spaces, and a well-appointed kitchen designed for gathering. Coastal-inspired interiors and thoughtful design create an inviting retreat for owners and guests alike. Located in the heart of Anna Maria Island, with nearby trolley stops providing easy access from Bean Point to Bridge Street, this home offers a rare opportunity to fully embrace the laid-back rhythm of one of Florida’s most sought-after beach communities!
Listing is courtesy of: HUNT BROTHERS REALTY, INC. (941-388-7017)
Listing Agent: Jennifer Albright (941-284-3092)
306 66TH ST, HOLMES BEACH, FL 34217
$1,475,000159 Days on yellowkey MLS ID: A4678590
REDUCED by $75,000 (4.8%) on 06/09/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1502 Built: 1962 Tax: $15,256 (2024)Community: Key Royale TerraceSingle Family
Taxes:$15,256
Remarks: Welcome to LivinGood, a thoughtfully redesigned beach home where effortless indoor-outdoor living shines. Slide open the glass doors and step directly into your private pool and entertainment area, keeping family and guests seamlessly connected without the need to climb a single set of stairs. This completely remodeled 3-bedroom, 2-bath pool home is offered turnkey furnished and blends modern luxury with laid-back beachside charm, with beach access just minutes away. Inside, impeccable craftsmanship is highlighted by restored terrazzo floors, a gourmet kitchen with quartz countertops, all-wood custom cabinetry, and a high-end gas range, a split floor plan for added privacy, and fully updated bathrooms with modern finishes. The home is equipped with a tankless water heater, two mini-split units, a top-of-the-line Trane A/C system, and an EV charger for comfort and efficiency. Outdoors, enjoy a custom high-end pool built by one of the top pool builders on AMI, a screened-in lanai, lush low-maintenance turf, a putting green, built-in closets, ample storage, and close proximity to the island’s best dining and shopping. Everything has been thoughtfully designed with the end user in mind. Schedule your private showing today!
525 68TH ST, HOLMES BEACH, FL 34217
$6,145,000228 Days on yellowkey MLS ID: A4671356
REDUCED by $5,000 (0.1%) on 06/02/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3574 Built: 2025 Tax: $11,692 (2024)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$11,692
Remarks: Just Completed Coastal Southern Retreat on the Grand Canal! Welcome to 525 68th Street, an elegant newly completed Southern-style residence perfectly positioned along the coveted Grand Canal in Holmes Beach. This 4-bedroom, 4.5-bath masterpiece offers timeless charm blended with modern coastal luxury. Each spacious en suite bedroom exudes comfort and style, while a private study provides the perfect quiet escape. The open-concept chef’s kitchen is designed for entertaining, featuring premium appliances, custom cabinetry, and designer finishes. An elevator connects all levels, leading to expansive porches and a stunning rooftop deck with panoramic views of Tampa Bay and the Gulf of Mexico—ideal for sunset gatherings or morning coffee. Step outside to your private oasis—lush tropical landscaping surrounds a heated pool and spa, creating a serene setting for relaxation or waterfront entertaining. With some of the best boating water on Anna Maria Island and quick access to the Intracoastal and Gulf, this property is a boater’s dream. Beautifully designer-furnished and move-in ready, this home invites you to enjoy island living at its finest—just moments from the charming shops, restaurants, and sugar-sand beaches of Holmes Beach. Spend your holidays in pure coastal elegance!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Charles Buky (941-228-6086)
600 MANATEE AVE #145, HOLMES BEACH, FL 34217
$549,000105 Days on yellowkey MLS ID: A4685147
REDUCED by $50,000 (8.3%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1179 Built: 1977Monthly Fee: $925 Tax: $2,232 (2025)Community: Westbay Cove IiCondo
Taxes:$2,232
Remarks: First-floor corner unit with amazing bay views in the waterfront community of Westbay Cove on Anna Maria Island. This 2 bedroom, 2 bathroom condo offers a bright, functional layout with abundant natural light and peaceful views of the bay. The kitchen features custom cabinetry, tile backsplash, and newer appliances, and opens to the main living area and enclosed Florida room. The Florida room adds additional living space and is the perfect place to enjoy morning coffee while taking in the bay breezes and sunrise skies. The primary suite includes a walk-in closet, private sliding-door access to the Florida room, and an updated en suite bath with a quartz vanity and tile flooring. The guest bedroom is generously sized with dual closets and an ensuite bathroom featuring quartz countertops and a custom tiled shower. The guest bedroom also has private access to the screened front lanai. Additional features include hurricane-rated windows (sliders are not hurricane-rated), updated flooring, and a new stackable washer and dryer in the screened front lanai. The unit is being sold turnkey furnished, making it move-in ready for seasonal use, full-time living, or investment. Westbay Cove is a well-maintained bayfront community on Anna Maria Island offering two pools and beautifully landscaped waterfront grounds. Located just minutes from Anna Maria Island beaches, restaurants, and shopping.
Listing Agent: April Green (941-773-1680)
302 67TH ST, HOLMES BEACH, FL 34217
$1,399,900199 Days on yellowkey MLS ID: A4674440
REDUCED by $50,100 (3.5%) on 05/27/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1552 Built: 1960 Tax: $6,504 (2025)Community: 67Th Coastal Cottages Or2448/1887Spa: NoSingle Family
Taxes:$6,504
Remarks: The fabulously updated kitchen and open floor plan, make this 3 bedroom/2 bath half duplex a picture perfect island escape. Ideally situated on a quiet corner lot in the heart of the island, it is a straight walk down the street to the sugar sand beach, making it a popular vacation rental too! The split bedroom plan is perfect for hosting, and the updated, private, heated pool and trellis invite you to step out your wall of sliders and enjoy the Florida sunshine. You will love the coastal charm of the beach inspired décor, with wainscoted walls, freshly painted interior, white wood trim, tile flooring throughout, recessed lighting, stainless steel appliances, quartz counters, farmhouse sink and white shaker style cabinetry to the ceiling. Step out for a dip in the pool from your large primary en suite with high ceilings, and a bathroom with dual vanity and a walk in shower. Your spacious guest rooms on the other side of the house, are privately situated and enjoy ample natural light through large windows. This slice of paradise is perfectly situated, with easy beach access and just down the street from the free trolley stop. Enjoy your island time stress free in this like-new home!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Erin Leathem (941-448-5616)
8010 MARINA DR, HOLMES BEACH, FL 34217
$1,095,000155 Days on yellowkey MLS ID: A4678584
1 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1469 Built: 1957 Tax: $15,450 (2024)Community: Holmes Beach 30Th UnitSingle Family
Taxes:$15,450
Remarks: Renovation-Ready asset + Dock! Seize the opportunity to create something truly special on Anna Maria Island. Located on an oversized 9,282 sq ft corner lot, this 3-bedroom, 3-bath residence offers rare flexibility and exceptional upside in one of Florida’s most desirable coastal markets. Currently featuring 1,868 square feet under roof, the home presents a blank canvas ready to be reimagined as your custom island retreat. Zoned for duplex use, the property opens the door to multiple possibilities—whether a full renovation, new construction, or income-producing strategy. Highlights include- Deeded dock (needing some clean-up work), located across the street. Existing pool and pool deck, ideal for year-round island living One-car garage plus carport for convenience and storage Private backyard, perfect for entertaining or quiet relaxation Previously utilized as a 7-night rental with a strong rental history The property was impacted by Hurricane Helene and is being offered AS IS. It has been thoroughly cleaned out and is ready for its next chapter—whether restored or completely re-envisioned. This is a rare chance to secure a generously sized corner lot with zoning flexibility on Anna Maria Island. Bring your vision, contractor, or architect and make it your own. Contact me today for details or to schedule a private showing.
Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)
Listing Agent: Shauna Ruby (941-544-2070)
403 75TH ST, HOLMES BEACH, FL 34217
$2,395,000418 Days on yellowkey MLS ID: A4650766
REDUCED by $90,000 (3.6%) on 06/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1900 Built: 1955 Tax: $17,404 (2024)Community: Bay Palms Add Fourth UnitSpa: YesSingle Family
Taxes:$17,404
Remarks: Charming Coastal Cottage in Holmes Beach. Welcome to this newly and meticulously remodeled coastal retreat, ideally located in the heart of Holmes Beach. This one-of-a-kind, artsy beach cottage blends timeless charm with modern elegance and smart technology. Step through the inviting rain glass double doors into a spacious open-concept living, dining, and kitchen area, where a dramatic lighted cupola and vaulted ceilings create a stunning first impression. A custom shell stone fireplace with a wood mantle adds warmth to the cozy seating area—perfect for relaxing or entertaining. The chef’s kitchen is a true showstopper, featuring an oversized, lighted quartz island with seating, beadboard cabinetry, and a custom wave-patterned glass backsplash. High-end appliances include an ILVE Majestic 4-burner gas stove with griddle, GE Café refrigerator, wine fridge, and porcelain farm sink—all designed with entertaining in mind.Craftsmanship continues throughout with custom millwork, shiplap accents, paneled walls, and solid-core doors. Oversized sliding glass doors open to reveal a tropical backyard oasis, complete with a free-form heated pool and spa, paver patio with artificial turf. The lush, mature landscaping with up lighting show off the tall palm trees, perfect for a evening cocktail party under the stars. The southern-facing yard is perfect for dining, lounging, and soaking up the sun. Each of the three bedrooms and 2.5 baths showcases custom chrome period fixtures, retro-inspired sinks, and designer details. Tech-savvy buyers will love the smart home features, including Lutron lighting controls, LED lighting, Sonos sound system, security cameras, and plantation shutters. The property includes a 250-gallon buried propane tank serving the on-demand water heater, gas grill, pool heater, and stove. It’s also generator-ready with existing plumbing and wiring in place. There is city dockage close by for boating enthusiast's This extraordinary home offers a rare blend of beachy charm and premium amenities including a "She Shed" which offers additional luxurious living space. Words cannot describe the uniqueness of this feature so call now for your private showing of this amazing property.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Gregg Bayer (941-799-9096)
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