Location: Holmes Beach
Do Not Show Listings
6005 GULF DR #219, HOLMES BEACH, FL 34217
$700,00034 Days on yellowkey MLS ID: A4689996
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1011 Built: 1980 Tax: $7,704 (2025)Community: Playa EncantadaSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,704
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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)
105 49TH ST, HOLMES BEACH, FL 34217
$3,750,00083 Days on yellowkey MLS ID: A4683981
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2999 Built: 1940 Tax: $41,424 (2024)Community: JonesSingle Family
Taxes:$41,424
Tax Year: 2024
Remarks: Beachfront Bliss – Gulf Views from Every Angle! Just one house from the beach, this 4-bedroom, 4-bath coastal stunner delivers postcard-perfect Gulf views straight from the kitchen sink—yes, you’ll actually smile while scrubbing plates! Natural light throughout, high ceilings, 2 sided fireplace, wet bar in the living room, open living area that flows into a chef’s kitchen. Stainless steel appliances, gas stove, double ovens and more! The coastal chic blue countertops and tile throughout for easy beach sand clean up! Step outside to your wrap around balcony to dine and enjoy the gulf breeze. Backyard features your private heated pool that includes a sun shelf. All the bedrooms are spacious and have their own privacy. The primary suite is upstairs with even better views of the Gulf to wake up to. Enjoy your private balcony AND a spiral staircase leading up to the roof top deck, ideal to watch sunsets and dolphins jump in the water. Master bathroom has a huge walk-in shower, soak in tub, dual sinks and a large walk-in closet that includes a safe. The location is central to the island, close to everything and very convenient. 30 day minimum rental period. One house away from the Gulf, this may be the island’s best-kept secret!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jason Sato (941-778-7200)
8301 MARINA DR #8, HOLMES BEACH, FL 34217
$110,00094 Days on yellowkey MLS ID: A4681411
0 Days Off yellowkey (back on 4/17/2026)
Bed: Bath: 0.0 Tax: $630 (2024)Community: Boat SlipsDock-Rackominium
Taxes:$630
Remarks: Under contract-accepting backup offers. Rare opportunity to own a premium boat slip with a 7,500-pound boat lift in the highly sought-after boating community of Holmes Beach on beautiful Anna Maria Island. Whether you’re an avid angler, sunset cruiser, or weekend sandbar explorer, this is your chance to secure effortless access to some of Florida’s most spectacular waters. Perfectly positioned for convenience and adventure, this slip allows you to lower your boat and be cruising within minutes. Enjoy direct access to the Intracoastal Waterway, where calm, protected waters make for easy navigation whether you’re heading north toward Tampa Bay or south toward Sarasota. From there, it’s a quick and scenic ride out to the Gulf of Mexico — famous for its turquoise waters, world-class fishing, dolphin sightings, and breathtaking sunsets. Imagine spontaneous afternoons on the water — cruising to waterfront restaurants for lunch, anchoring at nearby sandbars, or casting a line for snook, redfish, grouper, and tarpon. Early morning fishing trips and sunset cocktail cruises become part of your everyday lifestyle. No trailering. No boat ramps. No waiting. Simply arrive, lower your 7,500-lb lift, and go. Anna Maria Island is celebrated for its relaxed coastal charm, old Florida character, and strong boating culture. Holmes Beach offers a central island location with easy access to marinas, waterfront dining, boutique shopping, and pristine white-sand beaches. From exploring Egmont Key to docking at nearby island favorites, the possibilities are endless. Boat slips with lifts of this capacity are exceptionally rare on Anna Maria Island, especially in such a prime location. Limited inventory, high demand, and the island’s protected footprint make opportunities like this few and far between. Whether you’re securing a long-term investment or elevating your boating lifestyle, this slip represents both convenience and exclusivity. If you’ve been waiting for the perfect place to keep your boat ready at a moment’s notice in one of Florida’s most desirable waterfront communities, this is it. Embrace the Anna Maria Island boating lifestyle — effortless days on the water, unforgettable sunsets, and the freedom to explore the Intracoastal and Gulf whenever the mood strikes.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
201 54TH ST, HOLMES BEACH, FL 34217
$2,100,00072 Days on yellowkey MLS ID: TB8480803
REDUCED by $100,000 (4.5%) on 04/30/2026
Bed: 5 Bath: 0.0 Liv Area Sq Ft: 2320 Built: 1947 Tax: $23,032 (2025)Community: S.C. CobbApartment
Taxes:$23,032
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
Remarks: This exceptional turnkey 5-bedroom, 5-bath duplex on Anna Maria Island offers a rare investment opportunity just moments from the white-sand beaches of the Gulf of Mexico, as well as the island’s charming shops and top-rated dining. Comprised of two beautifully renovated cottages—a 3BR/3BA and a 2BR/2BA, all en-suite—this unique property is connected by a solid 8-inch concrete block wall for excellent sound insulation, with separate street entrances that provide privacy for guests. Fully renovated down to the bare block in 2009, both residences feature raised ceilings, travertine floors and showers, granite countertops, crown molding, updated plumbing and electrical, new windows and doors, and quality finishes throughout. The 3-bedroom cottage includes a stunning primary suite with a 10-foot lighted tray ceiling, while each cottage enjoys its own private heated pool, maximizing rental appeal. With strong established rental history, this income-producing island property is the perfect blend of luxury, privacy, and prime location.
Listing is courtesy of: CHIRINO REAL ESTATE (813-642-3325)
Listing Agent: Ana Chirino (813-642-3325)
302 67TH ST, HOLMES BEACH, FL 34217
$1,450,000166 Days on yellowkey MLS ID: A4674440
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: This one has it all! Beautifully remodeled with a fabulous updated kitchen and open floor plan, this 3 bedroom/2 bath half duplex lives like a single family home, with a private, heated pool and just steps to the direct beach access! Ideally situated on a quiet corner lot in the heart of the island, it is a popular vacation rental! The split bedroom plan is perfect for hosting, and the updated pool and trellis invite you to step out your family room sliders and enjoy the Florida sunshine. Don’t miss a minute of relaxation in 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. You will love your large primary en suite, with a walk out to the pool, high ceilings, and a bathroom with dual vanity and a walk in shower. Your spacious guest rooms 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 spot, and enjoy the benefits of the short term rental income when you’re not on island time!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Erin Leathem (941-448-5616)
412 80TH ST, HOLMES BEACH, FL 34217
$775,000385 Days on yellowkey MLS ID: TB8381151
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 866 Built: 1978 Tax: $4,570 (2025)Community: 80Th & MarinaCondo
Taxes:$4,570
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)
680 KEY ROYALE DR, HOLMES BEACH, FL 34217
$2,395,00063 Days on yellowkey MLS ID: A4686733
REDUCED by $100,000 (4.0%) on 04/14/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2000 Built: 1972 Tax: $12,379 (2025)Community: Key Royale 15Th AddSpa: YesSingle Family
Taxes:$12,379
Remarks: Stunning Fully Remodeled Canal-Front Oasis in Prestigious Key Royale! Welcome to your slice of paradise, a beautifully reimagined 3-bedroom, 3-bathroom waterfront retreat on exclusive Anna Maria Island. This coastal gem has undergone a complete remodel, blending contemporary luxury with relaxed island living in the sought-after Key Royale community, home to the island’s only private golf course and just moments from pristine Gulf beaches. Step inside to discover an open, light-filled floor plan with high-end finishes throughout: sleek new kitchens with premium appliances, elegant quartz countertops, and custom cabinetry; spa-like bathrooms featuring designer fixtures and walk-in showers; and spacious bedrooms offering serene comfort. Every detail has been thoughtfully updated for effortless Florida living. Outside, your private backyard paradise awaits – a sparkling heated pool and spa with a chiller for year-round enjoyment, perfect for cooling off on warm summer days or soaking under the stars. The expansive lanai provides ample space for outdoor dining, lounging, and entertaining while overlooking the serene canal. Boaters will love the direct canal access with a 12,000 lb boat lift and private dock with electric– ideal for quick runs to the Gulf, fishing, or exploring the Intracoastal waterways. No bridges to the bay means easy outings! Located in the heart of Holmes Beach on Anna Maria Island, you’re just minutes from world-class white-sand beaches, charming restaurants, boutique shops, and the laid-back vibe that makes this area a top vacation and year-round destination. Schedule your private showing today!
4200 GULF DR #205, HOLMES BEACH, FL 34217
$1,200,000132 Days on yellowkey MLS ID: A4677335
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1979 Tax: $11,620 (2024)Community: GulfsandsCondo
Taxes:$11,620
Remarks: Gulf Sands is located in a great location on Anna Maria Island. The unit offers a renovated 2-bedroom, 2-bath coastal escape with Gulf views, private balcony, full kitchen with in-unit laundry, a shared heated pool, and direct private beach access, perfect for island living with amenities and proximity to local attractions and dining. New Air Conditioning unit in 2024. All information should be independently verified by buyers and buyers agents.
Listing is courtesy of: MIKE NORMAN REALTY INC. (941-778-6696)
Listing Agent: Rochelle Bowers (941-920-4533)
510 69TH ST, HOLMES BEACH, FL 34217
$990,000114 Days on yellowkey MLS ID: A4679951
REDUCED by $80,000 (7.5%) on 04/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1500 Built: 1976 Tax: $5,314 (2024)Community: Bay Palms AddSingle Family
Taxes:$5,314
Remarks: This stunning completely renovated 2-bedroom, 2-bathroom home offers 1,500 square feet of bright, open-concept living space designed for effortless island lifestyle. Step inside to find a seamless flow between the gourmet kitchen, dining area, and spacious living room—perfect for relaxing with friends, family gatherings, or simply soaking in the Florida sunshine that pours through large windows. The thoughtful renovation shines through with contemporary finishes, high-quality fixtures, and a fresh, inviting palette that feels brand new yet timeless. Both bedrooms provide comfortable retreats, while the well-appointed bathrooms add a touch of luxury. Situated on a prime lot in desirable Holmes Beach, you'll enjoy generous outdoor space—ideal for morning coffee, evening barbecues, or creating your own tropical oasis. Just moments from the sands of Manatee Public Beach and the calm Gulf waters, this home puts you in the center of Anna Maria Island's relaxed charm: pristine beaches, boutique shops, waterfront dining, and easy access to everything the island offers.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Craig O'Rourke (877-366-2213)
3701 5TH AVE #1, HOLMES BEACH, FL 34217
$669,00055 Days on yellowkey MLS ID: A4686018
REDUCED by $26,000 (3.7%) on 04/28/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1430 Built: 1982 Tax: $3,272 (2025)Community: Gulf View TwnhsSpa: NoCondo
Taxes:$3,272
Remarks: Gulf View Town Houses Condominium is one of a few select small association properties nestled just south of Manatee Public Beach. Just far enough away for a quiet beach day and just close enough to be an attractive location for vacation renters. A convenient grocery store and shopping district are just 1/8 mile east of this Holmes Beach condominium, making errands a breeze. The Association has been diligent and timely with their maintenance and repairs of the building and common elements, which are in tip top shape. Beach access is a short 150-yard walk west, offering the public beach restaurant and tiki bar just a short stroll north. This is one of the premier weekly rental locations in Holmes Beach and Anna Maria Island as a whole. Unit #1 has two designated parking spaces, a small first floor storage shed, and is one of just four units in this intimate single building condominium complex with heated pool on a spacious corner lot. West facing, with tons of light, this spacious two story 2 bed 2.5 bath condominium is the ultimate in hassle free island living for both owners and renters. On the first floor you will find tile floors throughout an open floor plan with an all-wood cabinet galley kitchen with induction cook top/range and hood, nice breakfast nook, and large living room with ½ bath. The kitchen also features full matching stainless GE Profile line appliances in great shape. A 5x12 ft balcony just off the living room is perfect for sunset viewing and windows and doors are hurricane rated and have been replaced in the past few years. Upstairs find the Primary en-suite bedroom with private west facing balcony and full tile bath with whirlpool tub and separate shower. The guest bedroom is also roomy with private full tile shower bathroom. The laundry room with washer and dryer are also found on the second floor. Definitely schedule a showing to take a closer look! Thanks *A FEW PHOTOS ARE VIRTUALLY STAGED*
Listing is courtesy of: ANNA MARIA ISLAND REAL ESTATE CORPORATION (941-504-7821)
Listing Agent: Bill Romberger (941-504-7821)
659 KEY ROYALE DR, HOLMES BEACH, FL 34217
$7,350,000237 Days on yellowkey MLS ID: A4665652
REDUCED by $300,000 (3.9%) on 04/27/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4984 Built: 1972 Tax: $31,373 (2024)Community: Key Royale 12Th AddSpa: YesSingle Family
Taxes:$31,373
Remarks: Pre-Construction. To be built. Looking to build BRAND NEW CONSTRUCTION with FULL BAY VIEWS in the fabulous Key Royale boating and golfing community? This 15,000 sq. ft lot has been fully cleared and is ready to go! The first photo is a proposed design by noted Sarasota designer Brian Phipps including building plans and pricing by local Sarasota builder. You can also bring your own plans and builder. Option to buy the vacant lot separately for $4,200,000. Plan specs: 5B/5.5B/+DEN with 4984 sq.ft and total of 11,321 sq.ft. and will include a 3 car garage, roof top deck, designer pool and spa and will feature high end builder upgrades for the most discerning buyers. Enjoy unobstructed views of the Tampa Bay and Sunshine Skyway. Build your island dream home, or create a sensational waterfront investment property. Plans and elevations are available for your review. Floor plan, square footage, etc. have been calculated based on current design by local builder and can be shared on request.
Listing Agent: Cindy Quinn, Pa (941-780-8000)
727 KEY ROYALE DR, HOLMES BEACH, FL 34217
$3,800,000456 Days on yellowkey MLS ID: TB8348338
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3640 Built: 1988Monthly Fee: $150 Tax: $45,927 (2024)Community: North Point Harbour Unit ThreeSingle Family
Taxes:$45,927
Remarks: Experience an unparalleled coastal retreat in the exclusive North Point Harbor enclave of Holmes Beach, situated on the highly coveted northern end of Anna Maria Island. This meticulously maintained, 3,640 sq. ft. custom-built estate is a waterfront masterpiece, offering direct, deep-water access to the Gulf of Mexico and Tampa Bay from the prestigious, quiet shores of Key Royale. The residence features a thoughtful and expansive layout consisting of 5 bedrooms plus a versatile bonus room and 6 bathrooms (4 full, 2 half), perfectly blending grand-scale functionality with sophisticated artisan craftsmanship. Built with a focus on both aesthetic elegance and structural longevity, the home boasts a durable metal roof, refined vinyl wood and tile flooring throughout the open-concept living spaces, and two massive balconies specifically designed to capture breathtaking, panoramic water views from nearly every room. Seller financing available, subject to terms. For the maritime enthusiast, the property’s private dock and dedicated boat slip provide the ultimate convenience: effortless, no-bridge navigation for a yacht or sportfish, allowing for easy access to the open waters of the Gulf or the fishing grounds of Egmont Key. Beyond the residence, the lifestyle is defined by the unique character of Anna Maria Island (AMI). Known for its "Old Florida" charm, AMI strictly limits high-rise development, ensuring unobstructed views and sunset vistas. This golf-cart-friendly community allows for a seamless transition from the front door to the pristine white sands of the Gulf beaches or the boutique shops and world-class dining found along Pine Avenue and Gulf Drive. The Key Royale area is revered for its serenity, offering a private golf club and a tranquil atmosphere tucked away from main thoroughfares. North Point Harbor further elevates this experience with meticulously maintained grounds and private tennis courts for residents. Strategically positioned, the property is a short boat ride or drive from the cultural hubs of Sarasota and St. Petersburg, providing a quiet escape from the hustle and bustle of mainland life. This home offers the security of an impeccable history with no flood damage, standing as a move-in-ready property maintained to the highest technical standards. Whether hosting a gathering in the chef-inspired kitchen, enjoying a quiet evening on the screened lanai overlooking the pool, or launching a vessel for a sunset cruise, this property offers a lifestyle of coastal elegance and resort-style luxury. It is a standout choice for any buyer who values infrastructure as much as aesthetics. From the durable building envelope to the artisan-finished interiors, every detail of this Key Royale estate has been curated to provide a high-quality home in a sought-after island destination. Embrace the island life where the only daily deadline is the sunset, and the backyard is a gateway to the finest waterways in the world.
Listing is courtesy of: ENGEL & VOLKERS TAMPA DOWNTOWN (813-863-1986)
Listing Agent: Razin Mcfarland (813-484-0519)
454 63RD ST, HOLMES BEACH, FL 34217
$899,99982 Days on yellowkey MLS ID: A4684367
REDUCED by $17,001 (1.9%) on 04/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1375 Built: 1962Monthly Fee: $150 Tax: $10,360 (2024)Community: Seaside GardensVilla
Taxes:$10,360
Remarks: Welcome to Villa Mar! A luxury vacation rental directly on Watsons Bayou with open water views. This completely renovated 2BD/2BA corner villa is the largest floor plan in Seaside Gardens and features updated kitchen with waterfall counter, brand new appliances, luxury baths, oversized wood plank tile throughout, impact windows and doors, great storage, newer AC, new roof, and 7 inch PVC baseboards for peace of mind. This lot has an extra wide 2 car carport with built in storage cabinets and shed. A large screened patio is perfect for outdoor entertaining after a long day on the boat. A 27 foot boat dock with electric/water, fish cleaning station and 10,000 lb boat lift complete the package. Great location with tennis, shuffleboard, pickle ball and the dog park just steps away. Active weekly rental business! No HOA and no condo fees. Seaside Gardens is a historic civic association maintaining the communal spaces and a low monthly fee of only $150 includes sewer and water. This is the perfect island getaway!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Stephanie Leitao, Llc (941-773-2677)
6606 HOLMES BLVD #3, HOLMES BEACH, FL 34217
$869,000465 Days on yellowkey MLS ID: A4639824
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 910 Built: 1971 Tax: $8,412 (2024)Community: The Blue LagoonCondo
Taxes:$8,412
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 Agent: Jennifer Chatt (941-465-0045)
445 63RD ST, HOLMES BEACH, FL 34217
$579,00043 Days on yellowkey MLS ID: A4688793
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1065 Built: 1962Monthly Fee: $150 Tax: $4,207 (2025)Community: Seaside Gardens RepSingle Family
Taxes:$4,207
Remarks: This is what Anna Maria Island living is all about. Located in the desirable Seaside Gardens community, this renovated 2-bedroom, 2-bath home offers spacious rooms, updated interiors, and a relaxed, airy feel. Inside, you’ll find new stainless steel appliances, quartz countertops in both the kitchen and bathrooms and waterproof luxury vinyl plank flooring throughout. A newer roof and windows add to the list of thoughtful updates. The generously sized bedrooms provide plenty of room to unwind, while the renovated bathrooms offer a clean, modern finish. A dedicated laundry room with washer, dryer, and ample storage adds everyday convenience. Step outside to a fully fenced backyard—perfect for entertaining friends and family along with a private driveway for on-site parking. Being offered furnished, this home is ready to enjoy as your personal island retreat or as an income-producing rental. Spend your days boating, playing pickleball, or relaxing on the beach, soaking in the turquoise waters and sugar-sand shoreline Anna Maria Island is known for. With community amenities and the Intracoastal Waterway just steps away, it’s easy to enjoy the laid-back island lifestyle. Golf carts and pets are welcome, and the trolley stop near the neighborhood entrance makes exploring the island simple and convenient. A comfortable, well-located home in a sought-after community—this is island living made easy.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Mary Anne Muniz (651-470-7020)
5200 GULF DR #302, HOLMES BEACH, FL 34217
$749,000130 Days on yellowkey MLS ID: A4677566
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 832 Built: 1970Monthly Fee: $1,297 Tax: $4,263 (2024)Community: Martinique Apts SouthSpa: NoCondo
Taxes:$4,263
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 Agent: Adele Holland (941-587-6328)
130 50TH ST, HOLMES BEACH, FL 34217
$2,699,00086 Days on yellowkey MLS ID: A4683830
REDUCED by $100,000 (3.6%) on 04/23/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2947 Built: 2010 Tax: $37,816 (2024)Community: The Villas On 50Th StreetSingle Family
Taxes:$37,816
Remarks: Own the sunset and step into a lifestyle buyers dream about—and renters actively seek out. Just moments from the Gulf, this stunning 6-bedroom, 4.5-bath coastal retreat delivers the perfect blend of luxury, comfort, and exceptional income potential. Designed to host and impress, the home lives like a private resort. Outside, guests are drawn to the resort-style pool with a sun shelf, a relaxing hot tub, and a tranquil waterfall feature. The outdoor bar and expansive patio create an effortless entertaining space, while the rooftop deck offers unforgettable Gulf-view sunsets that elevate every stay. Inside, the bright, open-concept design is made for connection, comfortably accommodating large groups, families, or vacation guests. High-end finishes meet relaxed coastal style, creating a space that feels both upscale and welcoming—exactly what today’s buyers and renters are looking for. Whether you're building a strong vacation rental portfolio or securing your own coastal escape, this property stands out as a high-demand, memory-making destination with proven appeal.
Listing is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Lisa Tucker (863-206-2938)
6400 FLOTILLA DR #15, HOLMES BEACH, FL 34217
$629,000198 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)
4003 5TH AVE, HOLMES BEACH, FL 34217
$1,495,000203 Days on yellowkey MLS ID: A4669926
REDUCED by $3,000 (0.2%) on 04/02/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2200 Built: 2003 Tax: $22,346 (2024)Community: CasanasSingle Family
Taxes:$22,346
Remarks: Mediterranean-inspired coastal luxury just one block from the Gulf—this fully furnished, elevated single-family villa, “Island Oasis,” offers no HOA, complete privacy, and proven storm resilience with no damage to upper living areas. Solid construction, turnkey condition, and major system updates provide immediate peace of mind, especially with income projections between 153-193k annually, for those interested in renting. This exceptional Anna Maria Island retreat comfortably accommodates 8+ guests, featuring two king suites, a third bedroom suite with two queen beds, and additional sleeping space in the great room—ideal for personal use, multigenerational living, or income-producing potential. Recent upgrades include new roof (2024), refrigerator (2024), dishwasher (2025), washer/dryer (2024), AC units (2020 & 2017), and water heaters (2025 & 2019), along with a resurfaced pool with new coping, pavers, heater, and pump. Inside, the home showcases light-filled interiors, soaring ceilings, crown molding, and natural wood accents, blending refined coastal design with relaxed island comfort. The open-concept kitchen features wood cabinetry, tile backsplash, an eat-at island, and newer stainless appliances, flowing seamlessly into the main living and dining areas. Glass sliders open to a front piazza and private pool courtyard, creating effortless indoor-outdoor living. The primary suite offers a private balcony and a spa-style bath complete with a clawfoot soaking tub and walk-in shower, delivering a true owner’s retreat. Above it all, a rooftop terrace captures 360° sunrise and sunset views, with peek-a-boo Gulf and Bay views, setting the stage for unforgettable evenings in the delightful island breeze. Step outside and experience the Florida lifestyle—sun-drenched pool days, shaded terraces, and lush tropical landscaping create a private oasis just moments from the beach. A short walk leads you to the soft white sands of the Gulf, while nearby favorites like Skinny’s, Manatee Beach, Pine Avenue, boutique shopping, waterfront dining, and the free island trolley make island living effortless. Elevated, meticulously maintained, and offered fully furnished, this is a rare opportunity to own a resilient, income-capable coastal home in one of Florida’s most sought-after destinations. Anna Maria Island living at its finest—sun, sand, and effortless coastal luxury await.
Listing Agent: Jo-Lee Mansfield (843-303-7463)
401 77TH ST, HOLMES BEACH, FL 34217
$3,995,000216 Days on yellowkey MLS ID: A4667829
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3200 Built: 2024 Tax: $8,047 (2024)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$8,047
Remarks: THIS IS THE ONE! Welcome to Annabella by the Sea. Impeccably built to the highest standards in 2024 by Eason Builders Group. This luxury home is a coastal dream, situated in the heart of Anna Maria Island, featuring 4 stunning bedrooms, 4.5 baths, over 3200 sq ft of refined living space, and multiple covered outdoor spaces, combining elegant comfort with the best of island living. Located in an ideal location, walkable to the sugary beaches of the Gulf, close to dining, shopping, and local attractions. No expense spared on this contemporary gorgeous home with designer finishes throughout, a gourmet kitchen with oversized island, top of the line appliances, huge walk-in pantry, and custom cabinetry. The open concept is perfect for entertaining with a spacious living and dining room that seamlessly connects to a large balcony with more seating. Custom light fixtures, spacious bedrooms with private ensuites, a game room by the pool area and a family room on the second floor ensures there is room to unwind and relax! Last, but not least, the oasis back yard with covered lounge areas, a luxurious pool and spa, lush landscaping and multiple balconies is the perfect spot to hang out after a day at the beach. Or take your party to your roof top deck for sunset and panoramic views. This gorgeous home is spacious in every sense and comes completely furnished with luxury details, curated so all you need to do is bring your clothes. A great rental history, making it the perfect family retreat or an outstanding investment property. Call today to schedule your private showing. Own where your heart already lives!
Listing Agent: Dee Munn (407-346-4422)
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