Location: Holmes Beach
Do Not Show Listings
4255 GULF DR #229, HOLMES BEACH, FL 34217
$624,00082 Days on yellowkey MLS ID: A4684618
1 Days Off yellowkey (back on 5/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1367 Built: 1981Monthly Fee: $1,040 Tax: $4,347 (2024)Community: Island VillageSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,347
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Rarely available 3 bedroom, two bath condo in Island Village. Nicely updated, spacious condo is perfectly positioned just across the street from the stunning white sand beaches of Anna Maria Island offering effortless access to the Gulf of Mexico's turquoise waters and spectacular sunsets. Meticulously maintained this condo features impact windows, new AC in 2021, and a new roof in 2025. The interior boasts fresh finishes with crown molding, wood flooring and spacious bedrooms that comfortably accommodate family or guests. Additional features include under-building parking with 2.5 dedicated spaces (plenty of room for vehicles plus a golf cart), plus a private storage shed for bikes, beach gear or seasonal items. The resort-style community has 2 community pools, a tennis court, and pickleball courts for active recreation. Perfect as a primary residence, second home, or vacation getaway in one of Florida's most coveted beach communities. This one checks every box!
Listing is courtesy of: PARADISE PALMS REALTY GROUP (941-300-1394)
Listing Agent: Linda Benedict (941-224-5364)
215 65TH ST, HOLMES BEACH, FL 34217
$1,529,000379 Days on yellowkey MLS ID: A4652336
5 Days Off yellowkey (back on 5/12/2026)
Bed: 3 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 2184 Built: 2006 Tax: $11,797 (2025)Community: BeachwalkersSpa: YesSingle Family
Taxes:$11,797
Tax Year: 2025
Remarks: Under contract-accepting backup offers. SHORT TERM RENTALS One block from the beach! Welcome to Sand Palace on Anna Maria Island! This elevated 3 bedroom, 2.5-bath coastal home offers the perfect blend of relaxation and as a successful rental investment just one block from the sugary sands of the Gulf. Designed for indoor-outdoor living, this tropical oasis features brand new siding, a private, fenced backyard with a heated pool and spa, creating the ultimate sanctuary for family getaways. Inside, the home has been freshly painted and exudes comfort with turnkey furnishings, wood floors, high ceilings, and granite countertops. The gourmet kitchen is equipped with solid wood cabinetry, stainless steel appliances, and a generous island with breakfast bar, ideal for entertaining. Enjoy added luxury with a private elevator, central vacuum, two A/C units, metal roof, and an oversized four-car garage offering ample storage. Expand your living space with two spacious 28' x 11' covered porches, one off the main living area and another off the primary suite. This property is zoned for weekly short-term rentals, making it an exceptional income-producing property. Whether you're seeking a smart short term rental investment, a second home, or a forever island retreat, this home checks all the boxes. Located just steps from the beach and close to shopping, dining, and island attractions, this is coastal living at its finest. Call for your private showing today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Hannah Hillyard (941-744-7358)
204 29TH ST, HOLMES BEACH, FL 34217
$675,00018 Days on yellowkey MLS ID: A4693429
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1140 Built: 1959 Tax: $1,591 (2025)Community: IlexhurstSingle Family
Taxes:$1,591
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
Remarks: Get a piece of paradise! This charming island home is tucked away on beautiful Anna Maria Island with 2-bedrooms an 1-bathroom. Two Zero Four 29th Street sits on a desirable 6,000-square-foot lot and offers endless possibilities. Whether you're looking to get your hands on a starter project and refresh the home and personalize it to your hearts content. Convert the garage to a true primary suite and add some games in the empty bonus room. Or... if you prefer to really put your imagination to the task, you could create your dream island retreat from the ground up. This property is a rare chance to own in one of the Gulf Coast’s most sought-after locations. The interior of the home has been recently refreshed and features beautiful terrazzo floors that add timeless Florida character. Outside, the location truly shines — just two blocks from the sparkling blue waters of the Gulf of Mexico and the sugar-soft sandy beaches that make island living so special. Enjoy all the perks of life on this barrier island: sunshine year-round, walkable access to local boutiques, favorite restaurants, and the laid-back coastal lifestyle that makes Anna Maria Island such a beloved destination. A great opportunity to enjoy now, invest in for later, or build something truly special. Come live the Anna Maria Life!
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)
Listing Agent: Billi Gartman (941-545-8877)
212 72ND, HOLMES BEACH, FL 34217
$2,985,000387 Days on yellowkey MLS ID: A4651200
Bed: 4 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 2272 Built: 2019 Tax: $23,423 (2023)Community: 7173900; West Wind Shores; Lot 16; Block 21; Pb 7/Spa: YesSingle Family
Taxes:$23,423
Tax Year: 2023
Remarks: Newly renovated - Stunning 4-bedroom, 6.5-bath is perfect for beach lovers just a block from the Gulf of Mexico beaches. This island home features a backyard with a private pool and tiki bar, hot tub, BBQ area, covered patio with a foosball table, and a rooftop deck with water views. The main living space, includes a kitchen with a beautiful backsplash and quartz countertops, solid wood cabinets, island seating, couches, and a bright dining room with access to a covered deck overlooking the pool. The third floor hosts the primary bedroom, a private balcony with rooftop deck access, and an ensuite bathroom with a double vanity and a large shower. Outdoor amenities also include a pool, spa, This home is just a quick walk to the beach, and guests can easily take the trolley to Pine Ave for local delicacies, fish at the historic AMI city pier, or kayak in the bay waters.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Gregg Bayer (941-799-9096)
311 63RD ST, HOLMES BEACH, FL 34217
$1,699,000108 Days on yellowkey MLS ID: A4680267
REDUCED by $26,000 (1.5%) on 05/04/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1900 Built: 1971 Tax: $12,289 (2024)Community: Holmes Beach 17Th UnitApartment
Taxes:$12,289
Remarks: Own 2 Vacation / Investment Properties for the price of 1 with this Island Duplex -Live & Vacation in 1 Side / Rent the other with Strong Income Potential . Just a short 8 min. healthy walk to the beaches and downtown Homes Beach. This fully renovated duplex offers two private 2 BR/2BA residences, each with its own private entrance and each with a private heated and cooled pool ideal for renter interest. Designed for both easy living and high-performance rentals. This property is offered Turnkey Furnished with upgraded furniture and appliances as well as well as enclosed outside storage for each unit filled with Pool and Beach Toys. Each unit features an open-concept layout, updated systems including smart TV"S, private outdoor living spaces and a resort-style tropical setting. New AC'S, Hot water heaters and Decorative Metal Roof added in 2025. This is an ideal opportunity for Investors or Buyers seeking a personal Island Retreat that generates income as a weekly rental. Prime Location, Proven Performance with rentals in place for Effortless Island Living!
Listing is courtesy of: IVP OF FLORIDA INC (941-778-1000)
Listing Agent: Mel Neely, Pa (941-809-5565)
6006 GULF DR #214, HOLMES BEACH, FL 34217
$789,900126 Days on yellowkey MLS ID: A4678332
REDUCED by $105,100 (11.7%) on 05/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1154 Built: 1980 Tax: $11,060 (2025)Community: Playa EncantadaCondo
Taxes:$11,060
Remarks: Set within the beachfront enclave of Playa Encantada, this beautifully maintained two-bedroom, two-bath residence offers an effortless coastal lifestyle just steps from the sand and the island trolley — placing the area's finest shops, restaurants, and attractions within easy reach. Inside, an open and light-filled layout creates an inviting sense of space. The kitchen is appointed with granite countertops, stainless steel appliances, and generous cabinetry, while the living and dining areas flow seamlessly onto a private balcony overlooking the heated pool — an ideal setting to take in the Gulf breezes and glimpses of the water beyond. Both bedrooms are generously sized, with the primary suite featuring a private en-suite bath. Residents enjoy a thoughtful collection of resort-style amenities, including a heated pool, tennis courts, shuffleboard, and private beach access. A flexible two-week minimum rental policy further enhances its appeal, offering an exceptional opportunity as a seasonal retreat or income-producing investment.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Darcie Duncan (941-779-0304)
3604 GULF DR #A and B, HOLMES BEACH, FL 34217
$1,399,000127 Days on yellowkey MLS ID: A4679453
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1500 Built: 1968 Tax: $14,985 (2024)Community: CasanasSpa: YesApartment
Taxes:$14,985
Remarks: OVER 150K INCOME OVER LAST 12 MONTHS!!! Embrace the pinnacle of island luxury with this impeccably designed, turnkey Holmes Beach duplex—operating as a successful Airbnb and ready for seamless ownership transition. Each side features two spacious bedrooms and one bath, complete with gleaming marble countertops, white shaker cabinetry, elegant, natural-flow tile backsplashes and breathtaking remodeled bathrooms. With fresh paint, brand-new flooring, and a 2022 roof, the home is both stunning and secure. Every door and window is hurricane-rated and newly installed—offering peace of mind in every detail. Outdoors, one side boasts a heated pool with newly installed heater and a gorgeous waterfall feature, while the other side offers a soothing hot tub just installed in 2025 as well. Two outdoor showers add to the coastal experience, surrounded by lush, meticulously maintained landscaping. With five parking spots and separate entrances, you can host larger groups as a whole or individual parties in each unit and your guests will fall in love with this location when they find out public beach access is less than a block away! This duplex is uniquely positioned for maximum rental flexibility. Weekly rentals are fully allowed, making this a prime investment. High-end furnishings down to the last detail—silverware, plates, bedding, towels—ensure a seamless guest experience. Just steps from the vibrant charm of historic Bridge Street—known for its waterfront dining, boutique shops, and lively atmosphere—and minutes from the serene Bean Point, this property is at the heart of one of Florida’s top destinations. This is more than a home; it’s a fully operational, luxurious escape. Whether you’re continuing its rental success or claiming it for yourself, this is an unparalleled opportunity for coastal living and investment combined.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Johnny Hopper, Pa (941-524-1706)
5400 GULF DR #32, HOLMES BEACH, FL 34217
$939,00079 Days on yellowkey MLS ID: N6143360
REDUCED by $36,595 (3.8%) on 05/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1188 Built: 1969 Tax: $1,588 (2025)Community: 5400 Gulf Drive Apts 2Condo
Taxes:$1,588
Remarks: BEACHFRONT PROPERTY…...…..... OPEN TO SELLER FINANCING........FULLY FURNISHED........... BUILDING NEVER FLOODED………FULLY RENOVATED…….IMPACT WINDOWS…….........BREATHTAKING OCEAN AND BEACH VIEWS……….HOA PAYS EVERYTHING BUT ELECTRIC……………. Rarely does a beachfront opportunity like this come along. In a community where properties seldom hit the market, this residence stands out as one of the most desirable—MERE STEPS FROM THE SAND, overlooking the Gulf, and located in a building that has never flooded. With only 44 residences in the entire community and fewer than a dozen offering water views like this, opportunities here are incredibly limited. From the moment you step into the living room, your eyes are drawn to the sparkling blue water of the Gulf, reminding you that the beach is not just nearby… it’s part of your everyday life. Walk outside and within moments your feet are in the sand, or spend the afternoon relaxing beside the beautiful community pool just steps from your door. The community itself reflects a level of pride that is immediately noticeable, with beautifully maintained tropical landscaping and grounds that create a true island retreat the moment you arrive. Inside, the home has been fully renovated with thoughtful custom design and a bright open-concept layout, creating a space that feels both refined and relaxed. A custom kitchen anchors the living area, complemented by high-end finishes, California Closets custom storage, and impact windows throughout that bring in natural light while offering protection and efficiency. Being sold fully furnished, the next owner can simply arrive with a suitcase and immediately begin living the island dream—sunrise walks along the Gulf, evenings watching the sunset paint the water, and weekends filled with friends, family, and ocean breezes. With the HOA covering nearly everything except electricity, ownership here is refreshingly simple. Combined with the rare availability in this community and the possibility of seller financing, this is more than just a condo—it’s an opportunity to own a piece of Holmes Beach paradise that very few ever get the chance to call their own.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Garrett Sedlacek (913-461-6882)
4805 2ND AVE, HOLMES BEACH, FL 34217
$2,439,000116 Days on yellowkey MLS ID: A4679778
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2634 Built: 2009 Tax: $26,346 (2024)Community: 2Nd Ave & 49Th StreetSpa: NoSingle Family
Taxes:$26,346
Remarks: Anna Maria Island Coastal retreat, located west of Gulf Drive and only two blocks to the beach, offers the perfect blend of luxury, comfort, and investment potential. Featuring four bedrooms and three and half bathrooms and a bonus living area, this home has potential as a primary residence, vacation getaway, or income-producing property. The open concept interior showcases high ceilings, tile floors throughout, and a kitchen complete with granite counters, solid wood cabinetry, stainless steel appliances, and a large granite island ideal for entertaining. The spacious bedrooms offer large walk-in closets, while the bathrooms feature large tile showers, and the primary suite includes a relaxing jacuzzi tub. Three decks provide space for entertaining or sunset viewing. Outdoor living shines with a private tropically landscaped yard, heated pool and a fun tiki bar complete with TV, creating a true island oasis. The lower level features a two car garage with epoxy floors, storage area for beach equipment and a bonus game room. An elevator shaft offers the potential of future elevator installation. Close to world class beaches, dining, and shopping, this home has it all, capturing the ultimate Anna Maria Island lifestyle.
Listing Agent: Karen Mccall (276-971-2739)
303 58TH ST, HOLMES BEACH, FL 34217
$2,349,000169 Days on yellowkey MLS ID: A4674192
REDUCED by $100,999 (4.1%) on 05/06/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2524 Built: 2006 Tax: $26,409 (2024)Community: Casa Bella Of Anna Maria IslandSingle Family
Taxes:$26,409
Remarks: AMAZING LOCATION • COMPLETELY UPDATED • BRAND NEW POOL • BRAND NEW ROOF • TURN-KEY FURNISHED Casa Bella is a spacious and beautifully updated 4-bedroom, 3-bath home offering more than 2,500 sq ft in the heart of Holmes Beach. Located just steps from shopping and dining and only a 5-MINUTE WALK TO BEACH, this property is situated in one of Anna Maria Island’s most desirable WEEKLY RENTAL ZONES, making it an excellent investment opportunity or a ready-to-enjoy personal beach retreat. This home has undergone extensive recent updates, including new wood flooring throughout, a brand-new spool (pool with spa jets), and a brand-new roof. Casa Bella is offered turn-key furnished, featuring a thoughtfully curated collection of artwork and unique furnishings. The coastal-style interior includes a large great room, fully stocked updated kitchen with custom cabinetry, stainless steel appliances, stone countertops, and a spacious dining area. The home comfortably accommodates up to 10 guests, with three bedrooms featuring king beds and a fourth bedroom designed with two twin-over-twin bunk sets—ideal for families or renters. Additional features include A LOWER LEVEL RECREATION ROOM with a ping-pong table, three updated bathrooms with spa-style finishes, 2 owner closets and three screened porch areas, perfect for enjoying morning coffee or evening breezes. Situated on a LARGE CORNER LOT with lush tropical landscaping, the outdoor area offers a private FENCED backyard oasis with ample space for dining, entertaining, and relaxing by the pool. Turn the key and start enjoying the ideal Holmes Beach lifestyle—whether as a personal coastal retreat or a strong VACATION RENTAL PERFORMER, Casa Bella offers flexibility, comfort, and an exceptional location.
Listing Agent: Marlen Ryan (941-799-1046)
102 68TH ST #102, HOLMES BEACH, FL 34217
$759,000158 Days on yellowkey MLS ID: A4675905
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 986 Built: 1977Monthly Fee: $1,200 Tax: $9,465 (2024)Community: Seaside Beach HouseCondo
Taxes:$9,465
Remarks: Wake up to endless Gulf views in this stunning 1-bedroom, full Gulf-front condo, perfectly positioned in an exclusive boutique building of just 10 residences. Floor-to-ceiling vistas of sugar-white sand and emerald waters create a front-row seat to breathtaking sunrises, sunsets, and the soothing rhythm of the waves. This well-maintained beachfront condominium offers the rare combination of privacy, peace of mind, and investment potential. Owners enjoy a large beachfront pool, strong financial reserves, and a pride of ownership that’s evident throughout the property. Located directly on the beach, this residence also features weekly rental flexibility, making it an exceptional opportunity for those seeking both personal enjoyment and strong short-term rental income. Whether you’re looking for a serene coastal retreat or a proven investment in a high-demand rental market, this Gulf-front gem delivers on every level. Boutique. Beachfront. Income-producing. This is coastal living at its finest. This property is a weekly rental. AC is 2023.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Shannon O'Brien Kerney (941-737-5153)
600 MANATEE AVE #116, HOLMES BEACH, FL 34217
$499,90070 Days on yellowkey MLS ID: A4683381
REDUCED by $39,100 (7.3%) on 04/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1179 Built: 1977 Tax: $2,241 (2025)Community: Westbay Cove ICondo
Taxes:$2,241
Remarks: OWNER VERY MOTIVATED !! West Bay Cove in Holmes Beach! This fully updated condo is being offered turnkey furnished, making it an ideal vacation getaway, income-producing rental, or full-time home in paradise.PICKLE BALL ! The bright corner layout offers open, inviting living spaces and a peaceful setting overlooking the pool, creating the perfect spot to unwind after a day at the beach. Thoughtful updates throughout give the home a fresh, coastal feel that’s ready to enjoy from day one. Westbay Cove is a beautifully maintained waterfront community on the Intracoastal Waterway with stunning Tampa Bay views, lush tropical landscaping, two heated pools, and tennis court. Just a couple of blocks to the beach and close to the trolley line, pier, local dining, and shopping—with convenient on and off island access. Don’t miss your chance to own a slice of Anna Maria Island.Walk to Publix, Shopping, Dining and the Gulf!
Listing is courtesy of: BOYD REALTY (941-750-8844)
Listing Agent: Brenda Boyd May (941-730-8589)
6250 HOLMES BLVD #37, HOLMES BEACH, FL 34217
$850,000137 Days on yellowkey MLS ID: A4677811
0 Days Off yellowkey (back on 5/6/2026)
REDUCED by $10,000 (1.2%) on 04/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1536 Built: 1992Monthly Fee: $885 Tax: $4,005 (2025)Community: North Beach Village IiSpa: NoTownhouse
Taxes:$4,005
Remarks: Under contract-accepting backup offers. Income Producing - Turnkey - Fully Furnished - Vacation Rental Property located in the desirable North Beach Village community. 3D tour showing 360 degree views of the home available for a virtual walkthrough. Start generating rental income from day one with this highly successful income property, with over $30,000 in bookings already for 2026 and almost $10K in 2027! Whether you’re searching for a full-time island residence, a seasonal getaway, or a proven income-producing property, this exceptional offering truly checks every box. Experience the best of Anna Maria Island living, where every day feels like a vacation. This property allows weekly rentals, 52 weeks a year, providing maximum flexibility and earning potential. Located in the desirable pet-friendly North Beach Village community—with no size or breed restrictions—residents and guests alike enjoy a relaxed coastal lifestyle, complete with a large community pool ideal for swimming laps or unwinding after a day at the beach. This beautifully decorated condo is nestled within a quiet community and is just a three-minute walk to the sugar-sand shoreline. Enjoy being moments away from charming local shops, popular island restaurants, and all the laid-back character Anna Maria Island is known for. Prefer to leave the car behind? The free island trolley stop nearby makes getting around effortless. Outdoor enthusiasts will appreciate nearby amenities including a dog park, playground, basketball courts, pickleball, and tennis courts, all just minutes away. Inside, this inviting island retreat offers 1,536 square feet of bright, open living space, featuring three bedrooms, two and a half bathrooms, and indoor laundry. Recent updates include a new roof (2025) and a standout primary bathroom unlike any other in the community. The spacious primary suite boasts a large walk-in shower with seating, dual-sink vanity, linen closet, and a private commode area, creating a true spa-like retreat. The home also features hurricane shutters and a hurricane-rated reinforced garage door, offering peace of mind for owners and guests alike. Neutral flooring and soothing paint tones throughout create a calm, coastal atmosphere that both owners and guests will love. Multiple outdoor living spaces enhance the island experience, including a screened-in porch tucked among the trees for added privacy, two large balconies, and a private ground-level deck—perfect for enjoying island breezes and outdoor dining. A large sleeper sofa allows plenty of room for extra guests. On the ground level, in addition to the main living area, you’ll find a generous 10' x 14' bonus space, ideal for a home office, gym, or game room. There is also an oversized 9'6" x 8' owner’s closet/storage room, providing the perfect place to securely store personal belongings while the property is rented. Offered fully furnished and truly turnkey, this exceptional property presents a rare opportunity to own a slice of paradise with outstanding income potential. Whether you’re investing, vacationing, or settling in year-round, this home delivers the ultimate island lifestyle—sun, sand, and serenity just steps from your door. Shared condominium expenses may result in lower overall carrying costs compared to some single-family homes.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kim Bowersox (407-383-3519)
506 69TH ST, HOLMES BEACH, FL 34217
$1,095,000713 Days on yellowkey MLS ID: A4613878
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1470 Built: 1968 Tax: $8,674 (2023)Community: Bay Palms AddSingle Family
Taxes:$8,674
Remarks: This beautifully updated 2 bedroom, 2 bath pool home offers comfort, flexibility, and exceptional value in the heart of Holmes Beach, featuring a spacious bonus room that can easily function as a third bedroom, office, game room, bunk room, or creative space tailored to your needs. Now offered at a newly improved price, this property presents an exciting opportunity to own a versatile island retreat just minutes from the beach. Wrapped in mature tropical landscaping, the private backyard oasis is designed for both relaxation and entertaining, complete with a heated pool, outdoor shower, firepit area, and multiple shaded lounging spaces perfect for unwinding after a day in the sun. Inside, the open concept layout enhances the flow between living and dining areas, with pocket sliders that open fully to the spacious rear porch, creating seamless indoor and outdoor living. The fully remodeled kitchen is a true highlight, showcasing crisp white cabinetry, sleek countertops, stainless steel appliances, and a generous island ideal for gathering. The primary suite offers a peaceful escape with a well appointed ensuite bath featuring a walk in shower, double vanity, and accessible design. Additional features include a one car garage with a freshly coated floor. Located just a short golf cart ride from the beach, shopping, and dining, this move in ready home delivers easygoing island living with the flexibility today’s buyers are looking for.
5300 GULF DR #508, HOLMES BEACH, FL 34217
$949,900268 Days on yellowkey MLS ID: A4663927
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1057 Built: 1971 Tax: $12,939 (2024)Community: Martinique Apts NorthCondo
Taxes:$12,939
Remarks: Sweeping Gulf sunsets, sugar-white sand, and the unmistakable charm of Anna Maria Island — now offered at a refreshed price. Perched on the 5th floor of the Martinique, this rarely available beachfront residence puts the entire horizon at your feet, where turquoise water stretches as far as the eye can see and the nightly sunset show never plays the same way twice. Floor-to-ceiling glass pulls the Gulf straight into the open living space and primary suite, with sunlight shifting from gold to rose to amber across the day. Inside, a crisp coastal palette of stone countertops, shaker cabinetry, and a generous breakfast bar makes entertaining effortless, while two spacious bedrooms and two full baths offer comfort and privacy for family and guests. Beyond your door, the Martinique delivers true resort living — heated beachfront pool, tennis courts, and direct access to powder-soft sand and the calm, shimmering Gulf. A deeded garage and private storage keep paddleboards, bikes, and beach gear at the ready. And then there's the island itself. Anna Maria's seven-mile ribbon of old-Florida charm is yours to roam: hop the free island trolley to Pine Avenue's boutiques and cafés, cast a line off the beach, paddleboard the bayside flats, or settle in at the Sandbar for dinner with your toes in the sand. With no high-rises and a pace all its own, Anna Maria stays quietly, beautifully unchanged — the kind of place where seasons melt into one long coastal summer. A refreshed price on one of the Gulf's most coveted addresses. This is your spring to claim it.
5701 CARISSA ST, HOLMES BEACH, FL 34217
$3,295,00051 Days on yellowkey MLS ID: A4688232
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3124 Built: 1968 Tax: $17,433 (2025)Community: Holmes Gulf To Bay DevSingle Family
Taxes:$17,433
Remarks: Tucked away in a quiet area of the island in a lush, tropical setting just moments from the beach, this beautiful 5BD/4BA residence captures the essence of coastal living with effortless style and thoughtful functionality, offering an exceptional opportunity in a desirable weekly rental zone. Framed by swaying palms and vibrant landscaping, the home welcomes you into a light-filled interior where a spacious living room with soaring ceilings, elegant plantation shutters, and a cozy gas fireplace creates an inviting space to gather and unwind. The open flow continues into a well appointed kitchen equipped with everything the family chef could want including a dining nook, but that family chef will love the scullery area with an additional stove and dishwasher for all the family gatherings. The scullery opens to the exterior where the outdoor grill and pizza oven are right at your finger tips. Two ensuite bedrooms, including a serene primary suite, offer comfort and privacy, while the remaining spacious bedrooms provide generous accommodations for the whole family. Step outside to a private pool area designed for soaking up the Florida sunshine, featuring a pool chiller for year-round comfort and surrounded by ample space for lounging and entertaining, along with two convenient outdoor showers. Practical features abound with natural gas service, a whole house generator, a durable metal roof, impact windows and more. There is also an exterior storage shed for all the beach toys, and abundant parking including two circular driveways on this corner lot. Located in the heart of Holmes Beach this location can’t be beat with a short walk to local shops, eateries and most importantly the sugar white sand and turquoise gulf waters.
101 66TH ST #6, HOLMES BEACH, FL 34217
$775,000102 Days on yellowkey MLS ID: A4682831
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 939 Built: 2009 Tax: $8,795 (2024)Community: Mainsail Beach InnSpa: YesCondo
Taxes:$8,795
Remarks: Experience the perfect blend of luxury beachfront living and strong investment potential with this rare Gulf-front condo-hotel residence on Anna Maria Island, designed in the timeless style of a charming New England coastal inn. This intimate 12-unit boutique community offers direct access to the sandy beaches of the Gulf of Mexico and delivers one of the most desirable beachfront locations in Florida. Unit #6 is ideally positioned on the second floor and accessed by both an elegant staircase and elevator, offering convenience along with privacy and elevation for enhanced views. This spacious 2-bedroom, 2.5-bath beachfront condo features beautiful original hardwood flooring, crown molding, and a bright open layout designed for coastal comfort. A rare highlight of the residence is its two private balconies, one extending from the living room and the other from the primary suite, providing panoramic Gulf views, pool views, and unforgettable sunset skies—perfect for morning coffee, evening relaxation, or listening to waves rolling onto the shore. The interior is thoughtfully appointed with built-in closets, in-unit washer and dryer, and a fully turnkey package that includes furnishings, décor, beach equipment, kayaks, and paddleboards, allowing for immediate enjoyment without additional setup. As part of a professionally managed condo-hotel investment property, owners benefit from up to 120 days of personal use a year while the on-site management team handles rentals the remainder of the time. With its prime beachfront location on Anna Maria Island, the property consistently achieves strong occupancy rates, making it an attractive income-producing vacation rental investment. Even better, ownership allows you to enjoy months of personal beachfront living annually while rental income helps offset operating costs, creating both lifestyle value and financial efficiency. Offered fully turnkey, this residence checks every box for buyers seeking a luxury beachfront condo on Anna Maria Island, a Gulf-front vacation rental investment property, or a low-maintenance coastal retreat in Florida. Simply bring your swimsuit and start enjoying beachfront living at its finest—where lifestyle, location, and long-term value all come together in one exceptional opportunity.
Listing is courtesy of: WAGNER REALTY (941-383-5577)
Listing Agent: Ed Taaffe (636-346-6165)
3607 E BAY DR #211, HOLMES BEACH, FL 34217
$499,999105 Days on yellowkey MLS ID: A4682620
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 980 Built: 1996 Tax: $2,211 (2024)Community: Sandy Pointe IiCondo
Taxes:$2,211
Remarks: All the work is done. New flooring, new bathrooms, stainless appliances, updated kitchen, new bathroom vanities, showers have been updated with new tile, flooring. Hurricane windows, new siding new roof. Enjoy Island living and Island fun great location and walkable distance to the beach, shopping, restaurants, trolley, live music, bike rentals. Stunning Two-Bedroom, Two Bathroom condo on Anna Maria Island. Discover the perfect condo that has 2 car garage parking, with extra storage for bikes and kayaks. Views of the intracoastal, looking over a tropical preserve. PETS ALLOWED, NO flooding issues when you live on the top floor. two car parking tandem. Enjoy sipping coffee on the screen porch and watching the sun rise. Living on the top floor you have high ceilings that are vaulted. Having this condo could be a great permanent residence, a winter getaway or weekly vacation rental or an investment property. Don't miss the chance to experience island living at it's best. Walk to the beach hear the waves and watch the most breath-taking sunsets every night. Community pool, extra storage areas for floats, kayaks beach gear. Just two blocks to the beach. This unit is zoned weekly rental and could be a active vacation rental.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sharon Hightower (941-330-5054)
6908 HOLMES BLVD, HOLMES BEACH, FL 34217
$2,499,000127 Days on yellowkey MLS ID: A4679284
Bed: 6 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 2621 Built: 2013 Tax: $27,085 (2024)Community: 6906 Holmes BlvdSpa: YesSingle Family
Taxes:$27,085
Remarks: 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!
Listing Agent: Don Purvis (901-240-2180)
2908 AVENUE C, HOLMES BEACH, FL 34217
$975,00080 Days on yellowkey MLS ID: A4685256
REDUCED by $15,000 (1.5%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1040 Built: 1979 Tax: $4,078 (2025)Community: IlexhurstSpa: NoSingle Family
Taxes:$4,078
Remarks: Beach Vibes! This secluded island retreat offers a relaxed, easygoing vibe just a few blocks from the soft sands of the beach. You can settle right in and enjoy the fresh updates, including a brand-new metal roof and a refreshed interior featuring a 2-bedroom, 2-bathroom layout. The living space is bright and airy, with hard-surface flooring throughout and no carpet to worry about after a day by the water. The kitchen is ready for your favorite recipes with stainless steel appliances and neatly painted cabinets. Outside, the wrap-around deck provides a great spot to catch a breeze, while the covered front porch and large paver driveway offer plenty of room for vehicles and visitors. Tucked away on a quiet residential street in Holmes Beach, you are perfectly positioned near local shops, favorite dining spots, and the island’s grocery store. This is a wonderful chance to own a piece of paradise in a central yet peaceful location.
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Marcia Van Ginhoven (704-497-0664)
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