Location: Holmes Beach , 34217
Do Not Show Listings
608 GLADSTONE LN, HOLMES BEACH, FL 34217
$1,735,000106 Days on yellowkey MLS ID: A4684704
REDUCED by $100,000 (5.4%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1692 Built: 1972Monthly Fee: $8 Tax: $17,697 (2024)Community: Key Royale 15Th AddSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$17,697
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Tucked within the exclusive waterfront community of Key Royale on Anna Maria Island, this beautifully renovated canal-front residence offers an exceptional blend of island charm, privacy, and effortless island living. Designed to embrace the Florida lifestyle, the home is centered around a spectacular pool courtyard, where almost every room opens to the expansive outdoor living space, creating a seamless connection between indoors and out. Bathed in natural light due to its desirable southern exposure, the home invites sun-filled days by the pool and tranquil evenings under the coastal sky. The thoughtfully designed split floor plan features a private primary suite with ensuite bath, along with two additional guest bedrooms and a well-appointed second bathroom, offering comfort and flexibility for family and visiting guests. The home offers a new roof and seawall was replaced in 2006, ensuring lasting quality and peace of mind for years to come. Ideally situated on a deep-water canal, the property provides a 10,000 lb boat lift and dock with water and electric. Direct access to Tampa Bay, the Gulf of Mexico, and the Intracoastal Waterway, make it a dream for boating enthusiasts and lovers of life on the water. Also, located just moments from Anna Maria Island’s world-renowned beaches, charming boutiques, and acclaimed dining, this residence captures the essence of luxury coastal living in one of the island’s most coveted neighborhoods. Don't miss this extraordinary opportunity to experience the elegance, serenity, and waterfront lifestyle that make Key Royale truly exceptional.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Becky Sirigotis (941-201-8000)
507 58TH ST, HOLMES BEACH, FL 34217
$1,299,000146 Days on yellowkey MLS ID: A4680272
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1661 Built: 1953 Tax: $3,698 (2024)Community: Holmes Beach 14Th UnitSingle Family
Taxes:$3,698
Elementary School: None
High School: None
Middle School: None
Remarks: Anna Maria Island canal front with easy access to open water. Located just a few blocks to the beach. This home sustained flooding during Hurricane Helene and was remediated (stripped interior) post the storms of 2024. Build your dream home on a beautiful, mangrove lined canal on a quiet street centrally located on the island OR reimagine the possibilities of this raw structural skeleton.
Listing is courtesy of: MIKE NORMAN REALTY INC. (941-778-6696)
Listing Agent: Marianne Norman-Ellis (941-685-3393)
401 28TH ST, HOLMES BEACH, FL 34217
$1,525,000137 Days on yellowkey MLS ID: A4681048
REDUCED by $155,000 (9.2%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1656 Built: 1965 Tax: $15,915 (2025)Community: Sunrise ParkSpa: YesSingle Family
Taxes:$15,915
Tax Year: 2025
Remarks: ~Best Waterfront Value on the Island~ Welcome to your turn-key island retreat, a meticulously reimagined 3-bedroom, 2-bathroom waterfront home where thoughtful renovation meets serious boating credentials. Every inch of this property has been brought back to better-than-new condition through a complete renovation that included a comprehensive storm damage remediation strategy, giving you confidence in both the craftsmanship and the long-term resilience of your investment. Boaters, take note: this property boasts the closest boat lift to the beach north of Cortez — just a short distance to the sand and surf, giving you the best of both worlds. A heavy-duty 13,000 lb private lift stands ready for your vessel. With a remarkable 200 feet of waterfront on the canal, you'll have room to spare for water toys, dockside lounging, and quick deep-water access to the Gulf. Whether you're chasing tarpon at sunrise or cruising to a sandbar at sunset, you're already there. Step inside and discover an upgraded kitchen built for entertainers and home chefs alike, anchored by premium Thor appliances and an abundance of custom cabinetry that delivers both style and storage. The open layout flows seamlessly to your private outdoor oasis — a sparkling pool, relaxing spa, and convenient outdoor shower set the scene for everyday vacation living. A separate laundry room and attached garage add the everyday practicality that makes island life effortless. Tucked into a quiet pocket in the heart of the island, this home offers the rare combination of central location and peaceful surroundings. Best of all, there are no HOA fees — and dedicated parking accommodates your RV, boat trailer, or extra vehicles. Whether you're searching for the perfect second home to escape to season after season, or you're ready to make the leap to sunny Florida living full time, this property delivers on every front. Renovated, resilient, and ready to enjoy — this is coastal Florida living without the typical trade-offs.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Amy Ward (386-623-2525)
503 BAYVIEW DR, HOLMES BEACH, FL 34217
$899,000153 Days on yellowkey MLS ID: A4676121
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1960 Tax: $4,973 (2025)Community: Sunrise Park RepSingle Family
Taxes:$4,973
Remarks: Virtually Staged. Reduced, ACT FAST! Three-bedroom Anna Maria Island beach home, 300 steps to the island's world class beaches! This Holmes Beach retreat, located on Anna Maria Island, is ready and waiting for you! Discover this fully updated, bright and airy split plan, three-bedroom home spanning over 1,100 square feet, thoughtfully designed with open living space combining the kitchen and living room areas. Located on a quiet cul-de-sac, this home sits right in the Island’s sweet spot between the Cortez and Manatee Bridges, providing easy access on and off the island. You’re just a short walk or golf cart ride away from white sandy beaches, restaurants, shops, and a convenient free trolley stop. You will see all properties were not created equal as you step into your own tropical, completely private backyard oasis complete with screened in lanai, wet bar and highly sought after southern exposure. Bask in the sun, don't sit in the cold shadows with a subpar exposure. Enjoy a beautiful, heated saltwater pool equipped with sprayers, fountains, and a sun platform for ultimate relaxation. A multilevel waterfall pond adds to the tranquil atmosphere, featuring a charming bridge that leads you over the pond directly to the gorgeous pool area. The expansive 9,000-square-foot lot is enhanced by landscaping stones, providing ease of maintenance. The home features a metal roof and impact windows for peace of mind. It boasts 2025 appliances, including a washer and dryer, along with all-new cabinetry and quartz countertops in both the kitchen and master bath. Fresh paint and 5-inch base molding through-out complete the modern look and feel. This property is offered turnkey furnished and is rental ready for monthly stays. RV and boat parking allowed! There is nothing to do here but relax and enjoy your surroundings: take a dip in the pool, stroll to the beach, indulge in the varied dining options this island has to offer, from tiki bars to fine dining. Enjoy the manatees and dolphins playing in the canal across the street and parrots flying overhead! Immerse yourself in all the serenity and joys this beautiful island has to offer. Whether you’re seeking relaxation or adventure, this home provides the perfect base for enjoying Anna Maria Island’s unique charm and vibrant lifestyle. All NEW in 2025, Washer, Dryer, Refrigerator, Range, Dishwasher, Microwave, High Velocity Range Hood, Pool Heater, Pool Pump, Water Heater, Kitchen Cabinets and Quartz Countertops, Master Bath Cabinets and Quartz Countertop, Guest Bathroom with New Vanity and Top, All Furniture and Bedding. Impact Windows installed 2021 and 2022, Metal Roof installed 2018. Possible owner financing.
Listing is courtesy of: REALTY MARK ASSOCIATES (561-245-5400)
Listing Agent: Raymond Nesci (941-468-1608)
311 63RD ST, HOLMES BEACH, FL 34217
$1,699,000132 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 in 1 Side / Rent the other with Strong repeat weekly Income Potential. Just a short 8 min. healthy walk to the beaches and downtown Homes Beach. This fully remolded 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 total privacy each side. Designed for both easy living and high-performance rentals. This property is offered Turnkey Furnished with upgraded furniture and appliances 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. Parking for 4 vehicles makes this a unique property to avoid looking for parking on the Island and has a free trolley stand just across the street. 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! Looking for acceptable contract to close prior September 30, 2026
Listing is courtesy of: IVP OF FLORIDA INC (941-778-1000)
Listing Agent: Mel Neely, Pa (941-809-5565)
6808 PALM DR #B, HOLMES BEACH, FL 34217
$749,000285 Days on yellowkey MLS ID: A4664678
REDUCED by $10,000 (1.3%) on 06/17/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 925 Built: 1985 Tax: $10,397 (2024)Community: Clark Spring Lake EstatesSpa: NoHalf Duplex
Taxes:$10,397
Remarks: Welcome to Palm View Lakehouse in Holmes Beach. This fully renovated 2-bedroom, 2-bath ELEVATED half duplex was updated in 2022 and allows for weekly rentals, offering excellent investment potential with nearly $50,000 in year-to-date bookings and almost to $60,000 in bookings in 2024, plus several bookings already secured for next year. The home features luxury vinyl plank flooring throughout, granite countertops, stainless steel appliances, and IMPACT windows and doors, with both bathrooms updated with new tile and vanities. Outside, enjoy a PRIVATE heated saltwater pool, along with a DOCK added in 2023 where you can fish, kayak or paddleboard. Other recent improvements include a AC in 2021 and new garage door in 2025. Close in proximity to the Gulf beaches, dining, and shopping, this property blends island living with convenience and comfort.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jessica Batten (941-962-3380)
6300 FLOTILLA DR #81, HOLMES BEACH, FL 34217
$430,000175 Days on yellowkey MLS ID: A4676409
REDUCED by $20,000 (4.4%) on 06/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1151 Built: 1973Monthly Fee: $833 Tax: $5,786 (2024)Community: Shell PointCondo
Taxes:$5,786
Remarks: Virtually Staged. Welcome to Shell Point, a lovely waterfront community in the heart of Holmes Beach. If extra space is what you need this unit has it with the back lanai that is all remodeled part of the air conditioned space. This lovely updated condo is conveniently located near the Holmes Beach Boat ramp, tennis courts, basketball courts , dog park, and all within a short stroll to shopping, fabulous dining and of course the beautiful beaches of Anna Maria Island. This lovely 2 bedroom 2 bath unit has been wonderfully updated with beautiful wood grain tile floors, all new appliances, trim, doors, kitchen cabinets, bathroom cabinets, lights, and ceiling fans. It also boasts new window treatments, and hurricane windows and doors as well. This little "gem" of an island retreat, has extra interior space (extra square feet) with the bonus area that is located off of the living room. This air conditioned interior space has beautiful natural light just pouring in all morning and offers a back door to access the community pool and courtyard which has walking paths. A perfect space that can be used as an office space, reading space, entertainment space , or just a nice gathering space to rest and sip on your morning coffee. This unit is all brand new and just waiting for you to start making it your new island retreat.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Michelle Laade (941-737-9662)
308 60TH ST #A, HOLMES BEACH, FL 34217
$994,00029 Days on yellowkey MLS ID: A4694707
REDUCED by $5,000 (0.5%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1216 Built: 1980 Tax: $10,306 (2025)Community: Holmes Beach 15Th UnitSpa: NoHalf Duplex
Taxes:$10,306
Remarks: This home is a renovated 2-bedroom, 2-bathroom with a private den. The home has an open concept with the kitchen, dining area and living room. The primary suite has an en-suite bathroom. It has a private backyard and a heated and chilled pool. There is an upper deck and a lower covered outdoor living and dining area. It is in a weekly rental zone and has good history and 5-star reviews. This lovely property is convenient to the beach and in a very quiet Holmes Beach residential neighborhood. It has one shared wall with the unit next door that was double insulated during renovation to reduce noise. It's just a short walk to the many shops and restaurants of downtown Holmes Beach, as well as the Island’s only dog park. There is a storage room that includes a ping pong table, a beach cart, beach toys and lots of beach equipment and a propane grill and outdoor propane fire pit ready to enjoy.
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
2905 AVENUE C, HOLMES BEACH, FL 34217
$1,095,00062 Days on yellowkey MLS ID: A4690829
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1556 Built: 1978 Tax: $14,703 (2025)Community: IlexhurstSingle Family
Taxes:$14,703
Remarks: Welcome to your slice of Old Florida charm in the heart of Holmes Beach on Anna Maria Island. Just a 2-minute walk to the beach, this turnkey furnished home captures the easygoing coastal lifestyle that makes Holmes Beach so special. With its laid-back island feel, tropical setting and inviting spaces, this property is ideal as a primary residence, second home or income-producing property. Inspired by the character Holmes Beach is known for; cozy beach-town living, tropical surroundings and a relaxed pace - this home perfectly fits right in. Beautifully maintained and ready to enjoy, the home offers a flexible layout with a non-conforming 4th bedroom, an oversized garage with rec-room area, a screened-in Florida room and a covered patio perfect for enjoying the coastal breeze. The outdoor shower, lush landscaping and welcoming outdoor spaces add to the relaxed island appeal. With recent updates to include the roof replaced in 2018, hurricane impact windows in 2020, bathrooms updated in 2019, water heater replaced in 2022, as well as fresh interior paint, wainscoting and epoxy garage flooring completed in 2025 this home is ready for your next worry-free chapter on Anna Maria Island. The seller has also completed a pre-listing 4-point inspection with clean results, offering added peace of mind. Conveniently located near the beach, island dining and local shops, this is a wonderful opportunity to own a lovingly cared-for home in one of the most charming communities on Anna Maria Island. Note: Pool Rendering and estimate in attachments for informational purposes only.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Valerie Padur (315-489-7872)
215 81ST ST, HOLMES BEACH, FL 34217
$1,500,00068 Days on yellowkey MLS ID: A4690200
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2020 Built: 2002 Tax: $9,235 (2025)Community: Beachwalk Twnhms Ph 2Spa: YesSingle Family
Taxes:$9,235
Remarks: Newly updated with fresh paint throughout, brand new stainless steel appliances, quartz countertops on kitchen and bathrooms and so much more!! Nestled near the north end of Anna Maria Island, 215 81st Street is a three-bedroom, two and a half bath home boasting over 2,000 square feet of living space—an Airbnb gem zoned for weekly rentals. Just two blocks from some of the island’s most pristine beaches, this property offers a true tropical paradise out back. The fully fenced oasis features a gorgeous pool with a built-in hot tub, while the expansive paver-lined lounge area creates a true island escape. The elevated design includes a two-car garage and a game room—currently set up with a ping pong table, connect 4, and Tic Tac Toe but offering ample space to add additional attractions for guests. The second floor invites you into a bright, open living, dining, and kitchen area featuring a brand new LG stainless steel appliance package and gorgeous quartz countertops. This floor also features a half bath, complemented by a massive, screened-in balcony deck (freshly screened in less then a year ago) overlooking the pool oasis below—perfect for soaking in the tropical ambiance. You will also find a dedicated interior laundry room with full size washer and dryer on this floor as well. On the third floor, you’ll find three spacious bedrooms and two full baths, with the primary suite offering not only luxury but also absolutely gorgeous views from every angle—a panoramic reminder of the beauty that surrounds you on Anna Maria Island. This home is packed with recent updates: a 2022 roof, 2019 AC, and a brand-new water heater. The exterior shines with hardie board siding installed less than a year ago and fresh paint. Beyond the home, you’re a stone’s throw from Pine Avenue’s charm and all that Anna Maria offers—laid-back vibes, local eateries, and coastal culture. Fully furnished and turnkey, this is both a thriving investment and an island escape waiting for you.
Listing Agent: Johnny Hopper, Pa (941-524-1706)
6500 FLOTILLA DR #212, HOLMES BEACH, FL 34217
$499,00053 Days on yellowkey MLS ID: A4691983
REDUCED by $50,000 (9.1%) on 06/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1258 Built: 1979Monthly Fee: $713 Tax: $3,531 (2025)Community: Westbay Point & Moorings IiCondo
Taxes:$3,531
Remarks: Welcome to an inviting ground-level canal-front condo tucked into the highly sought-after WestBay Point and Moorings community on beautiful Anna Maria Island. This bright and airy 2-bedroom, 2-bath residence welcomes you with a private front courtyard—an ideal spot for morning coffee or a quiet read—then leads into a versatile enclosed lanai offering endless possibilities for a home office, sunroom, or additional entertaining space. Inside, the updated kitchen features KraftMaid cabinets, and new countertops, convenient pull-out drawers and a wet bar that make hosting effortless. The expansive dining and living room combination brings in natural light from multiple sliders and flows seamlessly to the enclosed back lanai, where peaceful canal views and glimpses of the community tennis courts set a serene backdrop. The primary suite is a tranquil retreat with lanai access, an updated ensuite bathroom and generous walk-in closet with abundant storage. The beautifully updated second bath serves the guest bedroom, which also enjoys direct access to the front lanai, plus its own walk-in closet. This ground-floor unit is especially attractive for its accessibility and, importantly, it did not flood. Beyond the home, WestBay Point and Moorings deliver resort-style amenities: a heated community pool and spa, well-maintained tennis courts, and a kayak launch for easy access to the canal and surrounding waterways. Nestled in the heart of Holmes Beach, the community offers a rare combination of convenience and privacy—close to shops, dining and the island’s renowned beaches, yet tucked away for peaceful, everyday living. This thoughtfully updated condo is a must-see for anyone seeking island living with comfort, storage and outdoor lifestyle conveniences. Short walk to restaurants, shops, and Island trolly stop.
Listing Agent: Martha Robel (941-773-4594)
101 73RD ST #1, HOLMES BEACH, FL 34217
$675,000228 Days on yellowkey MLS ID: A4669608
1 Days Off yellowkey (back on 6/15/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1980 Tax: $3,402 (2025)Community: Princess Martha AptsCondo
Taxes:$3,402
Remarks: Under contract-accepting backup offers. Virtually Staged. This is your golden moment! Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated one-bedroom, one-bath unit is a first-floor corner unit that has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf. This is a rare opportunity as unique buildings like this are few and far between. It could be the ideal place to call home or as a daily rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof and air-conditioning unit were installed in 2025. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Shellie Young, Pa (941-713-5458)
101 73RD ST #2, HOLMES BEACH, FL 34217
$700,000228 Days on yellowkey MLS ID: A4669721
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 810 Built: 1980 Tax: $3,478 (2025)Community: Princess Martha AptsCondo
Taxes:$3,478
Remarks: Under contract-accepting backup offers. Virtually Staged. This is your golden moment! Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated two-bedroom, two-bath unit has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf of Mexico. This is a rare opportunity as unique buildings like these are few and far between. It could be the ideal place to call home use as a daily rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof was installed in 2025, and the air-conditioning unit in 2022. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.
8106 GULF DR, HOLMES BEACH, FL 34217
$1,449,00046 Days on yellowkey MLS ID: TB8506585
REDUCED by $101,000 (6.5%) on 06/05/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1600 Built: 1980 Tax: $22,689 (2025)Community: EdgemereApartment
Taxes:$22,689
Remarks: Virtually Staged. COASTAL INVESTMENT OPPORTUNITY! TURNKEY ELEVATED DUPLEX JUST ONE BLOCK FROM THE GULF INCLUDING A DEEDED BOAT SLIP! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach! The perfect blend of personal retreat and income producing opportunity positioned just one block from the Gulf with your own private residential beach access. Each unit features 2 bedroom/2 bathroom and has been thoughtfully updated with coastal-inspired style, featuring newer appliances, updated furnishings and comfortable mattresses your guests will rave about, and they already do, with excellent reviews in place. Enjoy peace of mind knowing this home had a prelisting inspection, noting a solid metal roof & A/C system as well as hurricane-impact windows and sliding doors (just 4 years old). Step outside and soak in the island lifestyle. Both units offer private balconies with Adirondack chairs, perfect for morning coffee or sunset breezes. The fully fenced yard (just 6 months old) provides space to add a pool, while the grill in the side yard invites gatherings for relaxed coastal evenings. After a day at the beach, rinse off in the outdoor shower and store your gear in the owner’s storage room. Each unit is equipped with its own laundry/utility room complete with washer and dryer plus golf cart plug-ins for added convenience. The property also includes 2 kayaks, a paddleboard, and bikes, making it easy to enjoy everything the island has to offer. For water lovers, the bonus doesn’t stop there! This property includes a DEEDED BOAT SLIP nearby, giving you quick access to the water anytime you please! "The Launch Pad" is perfect for kayaks, which are included with the property. Bring your imagination for a future dock/boat slip. Built for durability and security, the home is elevated and equipped with flood systems and was regularly maintained for pest and rodent control for added confidence. Located just one street from the Anna Maria City limits, this property allows for weekly rentals, maximizing income potential. Whether you choose to live in one unit and rent the other or lease both for strong returns, this duplex offers flexibility and exceptional value in a prime coastal location. Ideal as a personal getaway, full-time residence or high-performing investment! Follow your nose to the salt air and chase the gorgeous sunset. This is your chance to own a slice of paradise with built-in income potential. No shoes required!
Listing is courtesy of: FLORIDA EXECUTIVE REALTY (813-972-3430)
Listing Agent: Danielle Redner (813-967-0175)
8106 GULF DR #A&B, HOLMES BEACH, FL 34217
$1,449,00056 Days on yellowkey MLS ID: TB8500298
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 1600 Built: 1980 Tax: $22,689 (2025)Community: EdgemereSingle Family
4307 GULF DR #207, HOLMES BEACH, FL 34217
$529,00053 Days on yellowkey MLS ID: A4691396
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1027 Built: 1974Monthly Fee: $1,242 Tax: $6,599 (2025)Community: Cayman CaySpa: NoCondo
Taxes:$6,599
Remarks: This beautifully updated 2BD/2BA coastal retreat offers the perfect blend of comfort, style, and location in the highly desirable Cayman Cay community on Holmes Beach. Ideally situated mid-island and just steps to the soft powdery sands of the Gulf, this TOP FLOOR residence is TURNKEY FURNISHED and truly MOVE-IN-READY. Inside, you’ll find a bright, open layout with a relaxed beach-inspired feel, HURRICANE IMPACT-RATED Windows and thoughtful upgrades throughout. A MAJOR RENOVATION opened up the kitchen and main living area, creating a more spacious and modern flow with NO CARPET throughout the unit. The well-appointed kitchen features upgraded cabinetry, modern countertops, tile backsplash and stainless steel appliances, making it perfect for both everyday living and entertaining. The main living space features custom wood accent wall detailing, adding a stylish coastal touch, and providing both durability and easy maintenance. Both bathrooms have been tastefully updated, and recent improvements include a NEW HURRICANE IMPACT-RATED TURTLE GLASS sliding door and a REFRESHED LANAI. Step out onto the screened lanai and enjoy peaceful surroundings with PARTIAL GULF VIEWS along with views of the pool and tropical landscaping, creating the perfect space to relax and unwind. Additional features include a private owner’s storage room and a designated covered carport space for Unit #207. Cayman Cay offers a well-maintained community setting with a heated pool, shuffleboard courts, and BBQ grilling area, perfect for relaxing after a day at the beach or enjoying time with family and friends. The location is truly unbeatable, just minutes from local restaurants, shopping, Publix, CVS, and everything that makes Anna Maria Island so special. For added convenience, the island trolley is nearby, making it effortless to explore the surrounding area. Enjoy convenient access on and off the island, along with a short drive to Sarasota Bradenton International Airport. Whether you're seeking a full-time residence, a relaxing vacation retreat, or an investment property, this condo delivers the perfect blend of location, modern updates, and easy island living. UNPACK, UNWIND, and START LIVING the island life from day one—while offering excellent INCOME POTENTIAL when you’re away.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Michelle Wasson (941-726-5166)
214 85TH ST, HOLMES BEACH, FL 34217
$1,199,99934 Days on yellowkey MLS ID: TB8510500
REDUCED by $50,001 (4.0%) on 06/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1398 Built: 1958 Tax: $11,839 (2024)Community: Holmes Beach 33Rd UnitSingle Family
Taxes:$11,839
Remarks: Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the heart of Holmes Beach on Anna Maria Island. Updated throughout in 2026, this move-in-ready residence offers approximately 1,398 square feet of stylish, single-level living designed for comfort and convenience. The bright and inviting interior features a modern kitchen with updated cabinetry and countertops, new shutters throughout, and thoughtful finishes that create a fresh coastal feel. Central air conditioning and electric heat provide year-round comfort, making this home ideal as a primary residence, vacation getaway, or investment property. Situated on a generous 0.21-acre lot, the property offers a large backyard with sliding glass door access, providing plenty of space to entertain, relax, or create your dream outdoor oasis. There's ample room for a pool, ADU, or additional outdoor living areas. Located on a quiet, low-traffic street, this home offers a peaceful setting with wonderful neighbors and a true sense of community. Enjoy the tranquility of island living while being just minutes from everything the north end of Anna Maria Island. Location truly is everything. You'll love the convenient access to sugar-sand beaches, an 8 minute walk to a public beach, island shopping, local cafes, restaurants, parks, and outdoor recreation. The golf-cart-friendly neighborhood makes it easy to explore and enjoy the island lifestyle. As an added bonus, all furnishings are included with the sale, making this a turnkey opportunity. Don't miss your chance to own a beautifully updated home in one of Anna Maria Island's most desirable locations.
Listing is courtesy of: INVESTCOR REALTY LLC (813-761-4250)
Listing Agent: Dylan Casarez (951-470-7551)
5325 MARINA DRIVE #423, HOLMES BEACH, FL 34217
$450,000455 Days on yellowkey MLS ID: A4645975
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1023 Built: 2017Monthly Fee: $2,918 Tax: $8,273 (2025)Community: Waterline Villas & MarinaCondo
Taxes:$8,273
Remarks: BEST PRICED UNIT FOR SALE at the Waterline Villas & Marina Residences. The Autograph Collection Residences are a sophisticated and stylish boutique hotel with 37 fully TURN-KEY furnished condos with a premier waterfront location on Anna Maria Island. 45’, BOAT SLIPS ARE free to use for owners while in residence!!! Built in 2017 all units feature 2 bedrooms, 2 full baths, a gourmet kitchen, separate living area and its own washer & dryer. Unit #423 is located in the southernmost "ISLAND" building detached from the main hotel that allows for more privacy. Owners have access to a boat slip while they are in residence. Nightly rentals can be easily handled by the on-site property management company Mainsail Lodging & Development, an award winning hospitality organization headquartered in Tampa. Enjoy the laid-back, Old Florida feel of Anna Maria Island. Park your car on-site and take the free trolley to explore everything the island has to offer. Waterline amenities include a graceful lobby with front desk, on-site management to assist with guest needs, heated resort-style pool with sun deck overlooking 50-slip marina that accommodates boats up to 45’, boat slips available (free for owners while in residence), on site fabulous "Chateau Anna Maria" restaurant and bar, charter boats for fishing and Eco tours, bicycles, paddle board, and kayaks free for owners, 24 hour fitness center, elegant ballroom for weddings, corporate gatherings, gift shop, complimentary Wi-Fi, Housekeeping and Concierge services. Zoning allows owners to stay in their units up to 120 days per calendar year and the dates do not have to be consecutive. Experience the dream of owning property on Anna Maria Island without the worry associated with management and maintenance!
Listing Agent: Cindy Quinn, Pa (941-780-8000)
532 70TH ST, HOLMES BEACH, FL 34217
$4,200,00019 Days on yellowkey MLS ID: A4693681
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4350 Built: 1963 Tax: $21,257 (2025)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$21,257
Remarks: Introducing one of Anna Maria Island’s most captivating bayfront residences, perfectly positioned along the pristine waters of Bimini Bay with sweeping panoramic views stretching across the open water and beyond. Encompassing more than 4,300 square feet of beautifully designed living space, this stunning estate embodies the essence of luxury island living. From the moment you arrive, the home’s elevated coastal architecture, lush tropical landscaping, and commanding presence create an unforgettable first impression. At the heart of the residence, a recent renovation transformed the main living areas into a sophisticated gathering space designed for relaxed family living and effortless entertaining. The chef’s kitchen serves as the centerpiece of the home, showcasing custom cabinetry, premium appliances, designer finishes, an eye-catching backsplash, and an oversized island where family and friends naturally gather. Thoughtfully designed for both beauty and functionality, the kitchen flows seamlessly into expansive living and dining spaces where walls of glass frame breathtaking bay views and fill the home with natural light. The open-concept design creates a seamless connection between indoor and outdoor living, allowing the beauty of the bay to become part of everyday life. Every space was designed to embrace the home’s spectacular setting. Five spacious bedrooms and five beautifully appointed bathrooms provide luxurious accommodations for family and guests. The waterfront primary suite features a private balcony and breathtaking sunrise views across the bay. Additional guest suites and custom bunk accommodations offer comfort, privacy, and refined coastal style throughout. Step outside and discover a private bayfront retreat unlike anything else on the island. The resort-style pool and spa overlook sparkling open water, creating a dramatic backdrop for relaxation and entertaining. Multiple terraces and balconies provide front-row seats to sunrises, passing boats, and the ever-changing colors of the bay. A private putting green adds another layer of enjoyment, while mature tropical landscaping enhances privacy throughout. For boating enthusiasts, the location is simply unrivaled. With no bridges and direct access to Tampa Bay and the Gulf of Mexico, the property offers effortless navigation for everything from offshore fishing adventures to sunset cruises and days exploring nearby sandbars and waterfront destinations. The private dock and 16,000-pound lift place endless adventures just steps from your back door. Yet perhaps the home’s greatest luxury is its setting. Positioned on one of Anna Maria Island’s most coveted stretches of shoreline, this residence offers the rare combination of expansive open-water vistas, direct boating access, modern coastal elegance, and the relaxed sophistication that defines island life. Beyond the property itself lies the timeless charm of Anna Maria Island. Leave the car behind and embrace a lifestyle where bicycles, golf carts, and sunset strolls are part of daily life. Explore sugar-sand beaches, browse the boutiques and galleries of Pine Avenue, and enjoy waterfront dining moments from home. Blending Old Florida charm with coastal sophistication, Anna Maria remains one of Florida’s most sought-after island destinations. This is more than a home. It is a private waterfront resort, an entertainer’s dream, and a rare opportunity to experience the very best of Anna Maria Island living.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
212 72ND, HOLMES BEACH, FL 34217
$2,985,000411 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)
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