Location: Holmes Beach
Keyword(s): Manatee High
Keyword(s) High School: Manatee High
Do Not Show Listings
5608 GULF DR #104, HOLMES BEACH, FL 34217
$799,000129 Days on yellowkey MLS ID: A4679030
REDUCED by $10,500 (1.3%) on 05/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1236 Built: 1981Monthly Fee: $1,150 Tax: $7,710 (2024)Community: Sun Plaza WestSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,710
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: ITS TIME TO Wake up to the sound of waves and endless Gulf views in this beautifully situated two-bedroom, two-bath condo directly on the Gulf of Mexico. Step outside and onto the coveted, sugar-soft sandy beaches that make this area so sought after—perfect for morning walks, sunset strolls, and carefree beach days. Inside, the condo features a newly renovated kitchen that’s both stylish and functional, ideal for entertaining or preparing meals after a day at the beach. The thoughtfully designed layout offers comfortable living spaces and bedrooms with excellent privacy, plus the convenience of an in-unit laundry facility for effortless everyday living. Additional highlights include downstairs storage, perfect for beach chairs and gear, along with underground parking for added peace of mind. Located just minutes from shopping, restaurants, and local dining favorites, this condo perfectly balances relaxed beachfront living with easy access to all the best the area has to offer. Whether you’re seeking a full-time residence, a vacation escape, or an investment opportunity, this Gulf-front condo delivers the coastal lifestyle everyone dreams of. Come live your Anna Maria Life.
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)
Listing Agent: Billi Gartman (941-545-8877)
117 81ST ST, HOLMES BEACH, FL 34217
$2,950,00092 Days on yellowkey MLS ID: A4684654
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2040 Built: 1974 Tax: $20,908 (2024)Community: Holmes Beach Dev 1St UnitSpa: YesSingle Family
Taxes:$20,908
Remarks: Welcome to 117 81st Street in Holmes Beach, a custom-designed coastal retreat steps to the beach that has been completely renovated inside and out, offering the perfect blend of modern luxury and effortless island living. This beautifully updated 4-bedroom, 3.5-bath home is being sold turnkey furnished, making it move-in ready or immediately available as a high-performing rental investment. The first-floor open layout is designed for both entertaining and everyday comfort, featuring a spacious living area that flows seamlessly into the gourmet kitchen and dining space. The kitchen is a true centerpiece of the home, showcasing a large island with custom concrete countertops, distinctive range accents, and ample space for gathering. Adjacent to the kitchen, the dining room features a built-in bar with open shelving, creating the perfect setting for hosting guests or enjoying relaxed island evenings. A conveniently located half bath is also situated on the main living level. All four bedrooms are located on the upper level, offering privacy and a well-designed layout for families and guests. The spacious primary suite serves as a relaxing retreat and features a beautifully designed bathroom with an oversized walk-in shower. A fun and functional bunk room with its own en suite bathroom provides the perfect space for kids or visiting guests, while two additional bedrooms share a Jack-and-Jill bathroom, creating a comfortable and efficient layout for larger groups. Step outside to your private backyard oasis featuring a brand-new heated pool and spa, a covered patio with warm wood ceilings, outdoor grill area, multiple lounge spaces, and two inviting fire pits—perfect for entertaining or unwinding after a day at the beach. Additional upgrades include a brand-new metal roof, along with extensive renovations throughout the home that make this property feel completely refreshed and modern. Located just steps from the white sand beaches of Anna Maria Island, the home is also conveniently close to the island’s best restaurants, shops, and local attractions. Whether you’re looking for a high-revenue producing short-term rental, a primary residence, or a private Florida retreat, this exceptional property offers incredible versatility in one of the island’s most desirable locations.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Matthew Huffman (941-567-9365)
221 85TH ST, HOLMES BEACH, FL 34217
$985,00026 Days on yellowkey MLS ID: A4693773
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1229 Built: 1977 Tax: $12,828 (2025)Community: Holmes Beach 33Rd UnitSingle Family
Taxes:$12,828
Tax Year: 2025
Remarks: Discover the best of island living in beautiful Holmes Beach! Nestled on a quiet street in a peaceful neighborhood, you’ll love the combination of boating access and close proximity to the beach this home has to offer. Elevated with impact windows, this 2-bedroom, 2-bathroom home is turnkey furnished and includes a deeded, unimproved boat slip at the end of 85th Street, perfect for boating enthusiasts and those seeking the ultimate coastal lifestyle. New roof installed in August 2025. The downstairs area has been professionally remediated and renovated, while the upstairs living area remained untouched by hurricanes in 2024. Situated on an expansive 9,000sqft lot, there is ample space to add a pool and create your own private oasis. Whether you’re seeking a primary residence or a tropical getaway, this property is ideal for enjoying Anna Maria Island living. Book your showing today!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Victoria Bouziane (941-737-9275)
711 MANATEE AVE, HOLMES BEACH, FL 34217
$589,90029 Days on yellowkey MLS ID: A4692722
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1479 Built: 1977 Tax: $6,011 (2025)Community: Westbay Cove SouthCondo
Taxes:$6,011
Remarks: Located at one of the HIGHEST ELEVATIONS on Anna Maria Island, this property did not experience water damage from past hurricanes. Turnkey furnished and move-in ready, this beautifully maintained 2BR/2BA condo offers peaceful water views, gorgeous sunrises, and the laid-back island lifestyle so many come to Anna Maria Island for. The updated kitchen with stainless steel appliances opens to the spacious great room and Florida room, creating an open and inviting space for relaxing or entertaining. The Florida room features a pull-out sofa and walls of windows overlooking the water, pool, and tropical landscaping. Both bedrooms are spacious with en suite bathrooms, including a large guest suite with a walk-in closet. The primary bedroom also enjoys water views and an adjoining flex space perfect for a home office or reading nook. Enjoy resort-style amenities including a saltwater pool overlooking the bay, tennis and pickleball courts, kayak and paddleboard storage, and a waterfront dock with direct access to Anna Maria Sound and Tampa Bay. Easy on and off the island, with Publix right around the corner, and just two blocks from Manatee Public Beach and close to the Kingfish Boat Ramp. Come see why this waterfront condo is the perfect place to enjoy the Anna Maria Island lifestyle.
Listing is courtesy of: SAUTER BY THE WATER (941-233-9180)
Listing Agent: Jim Sauter (941-999-8901)
204 29TH ST, HOLMES BEACH, FL 34217
$675,00029 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
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!
212 72ND, HOLMES BEACH, FL 34217
$2,985,000398 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)
3604 GULF DR #A and B, HOLMES BEACH, FL 34217
$1,399,000138 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
$939,00090 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)
102 68TH ST #102, HOLMES BEACH, FL 34217
$759,000169 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 Agent: Shannon O'Brien Kerney (941-737-5153)
101 66TH ST #6, HOLMES BEACH, FL 34217
$775,000113 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
$499,999116 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)
504 59TH ST, HOLMES BEACH, FL 34217
$1,695,000147 Days on yellowkey MLS ID: A4677906
REDUCED by $100,000 (5.6%) on 04/23/2026
Bed: 3 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 3126 Built: 2006 Tax: $8,402 (2025)Community: Holmes Beach 16Th UnitSingle Family
Taxes:$8,402
Remarks: Live the island lifestyle in this custom-built, ELEVATED canal home located in a quiet, no-HOA neighborhood just minutes from the heart of Holmes Beach. Built in 2006, this well-constructed residence offers peace of mind, privacy, and easy access to everything Anna Maria Island is known for—beaches, local dining, boutique shopping, and waterfront parks. The home features an open, multi-level layout designed for comfortable island living, with three spacious bedrooms, multiple balconies and porches, and CANAL and OPEN-WATER views from several levels. The primary bedroom is privately located on the first living level, offering convenience and separation from the additional bedrooms above. Boating enthusiasts will appreciate the private dock with deep-water access and NO BRIDGE RESTRICTIONS, allowing quick access to open water. Additional features include an ELEVATOR, METAL ROOF, four-car garage, ample storage, and room to add a pool for enhanced outdoor living. As one of the few elevated homes in the area, this property offers notable structural integrity and the opportunity to enjoy Anna Maria Island living with confidence.
Listing Agent: Jessica Batten (941-962-3380)
201 54TH ST, HOLMES BEACH, FL 34217
$2,100,00092 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
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)
659 KEY ROYALE DR, HOLMES BEACH, FL 34217
$7,350,000257 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)
234 85TH ST, HOLMES BEACH, FL 34217
$1,774,999426 Days on yellowkey MLS ID: A4648191
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1715 Built: 1989 Tax: $11,241 (2024)Community: Holmes Beach Thirty-Third UnitSpa: NoSingle Family
Taxes:$11,241
Remarks: Tucked away on a quiet, picturesque street in the heart of Holmes Beach, this ELEVATED WATERFRONT retreat offers a rare private coastal sanctuary. Perfectly positioned on a sprawling 225-foot waterfront SAILBOAT-DEPTH CANAL with NO FIXED BRIDGES and DIRECT ACCESS to Bimini Bay, the Intracoastal Waterway, and the shimmering GULF OF MEXICO. Wrapped in lush, tropical landscaping and framed by a natural mangrove shoreline, a 40+ ft TimberTech COMPOSITE DOCK stretches gracefully into the water; ready to welcome your large boat or sailboat. What sets this home apart is not just its breathtaking setting, but the peace of mind it offers. ELEVATED and STORM-TESTED, this home proudly boasts ZERO HURRICANE DAMAGE - a true rarity on the island. Built with an impressive LIST OF UPGRADES for ultimate resilience: breakaway garage walls REINFORCED with CONCRETE SUPPORTS, a 2023 standing seam ALUMINUM ROOF with underlayment that is MIAMI-DADE STANDARDS, HURRICANE-IMPACT windows and doors with UV protection, and hidden vent soffits and fascia. Step inside and feel the relaxed elegance of this coastal gem. SUNLIGHT floods through every room, dancing off the stunning plank-style porcelain tile floors and creating a warm, inviting atmosphere. The OPEN CONCEPT great room flows seamlessly into a beautifully updated kitchen where your inner chef can run wild. Outfitted with rich maple cabinetry, sparkling Quartz countertops, and top-tier stainless steel appliances. The oversized walk-in pantry is perfect for keeping all your culinary essentials tucked away. The home's bathrooms echo the same attention to detail, featuring gorgeous tilework, granite countertops, upgraded Toto commodes, and brand-new copper piping and plumbing (2025). Every corner has been meticulously cared but it’s the outdoor living that truly sets this property apart. Your private backyard oasis was designed for both relaxation and unforgettable entertaining. Expansive WRAP-AROUND DECKING, crafted from premium materials and beautifully maintained, offers plenty of space to gather with family and friends. The FENCED IN DECKING also is perfect for pets to roam safely, while the CUSTOM KAYAK LAUNCH invites spontaneous paddles through the tranquil canal waters. Dreaming of a pool? APPROVED PLANS are ready and waiting to transform this outdoor space into your personal tropical paradise. Down at the dock, life slows down. Watch dolphins play, drop a line, or simply sip a cool drink as the sun melts into the Gulf horizon. The wide canal offers ample space for larger vessels - a true rarity on the island. Additional features include a spacious 3-CAR GARAGE with TWO LARGE STORAGE areas perfect for paddleboards, fishing gear, or even a golf cart. Conveniently, a 50-amp outlet has been installed for a RV, boat lift or even a hot tub. Ample guest parking is a major plus when it comes to this property and could even accommodate a RV, boat with trailer or whatever your heart desires! Plus a proactive termite protection system. Best of all? This serene retreat is just a short stroll to the sugar-sand beaches of Anna Maria Island, charming local shops, and island-favorite restaurants - all easily accessible via the free island trolley. Whether you’re searching for a full-time coastal residence, a seasonal getaway, or a savvy investment (zoned R-1 with 30-day minimum rentals), this home checks every box. Come experience the magic of Holmes Beach waterfront living where every day feels like a vacation.
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Mike Polachek (941-524-0241)
3018 GULF DR, HOLMES BEACH, FL 34217
$1,500,000392 Days on yellowkey MLS ID: A4651692
Bed: 5 Bath: 0.0 Liv Area Sq Ft: 2320 Built: 1920 Tax: $14,695 (2024)Community: IlexhurstSpa: NoApartment
Taxes:$14,695
Remarks: This property is best suited for buyers seeking short-term rental income, a multi-unit investment, or a flexible owner-occupant strategy in a prime Holmes Beach location on Anna Maria Island. This income-producing triplex is located just steps from the Gulf beaches with no busy streets to cross and offers three separate rental units, including a 3-bedroom, 1-bath residence upstairs, plus a 2-bedroom, 1-bath unit and a studio apartment on the main level, allowing for multiple income streams, full-time investment use, or a live-in-one, rent-the-others approach. Currently operating as an active short-term rental, the property benefits from strong year-round demand driven by its proximity to the beach, dining, and entertainment near Bridge Street, as well as convenient access off the island via the Manatee Avenue Causeway. The central location also provides easy reach to IMG Academy, University Town Center, Lakewood Ranch, Downtown Sarasota, and both Sarasota-Bradenton International Airport and Tampa International Airport, making it attractive for owners, guests, and investors alike. Whether held as a turnkey short-term rental, positioned for a 1031 exchange, or used as a coastal residence with income, this Holmes Beach triplex offers a rare combination of location, flexibility, and proven rental performance.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Brooke Doucett, Llc (941-586-3522)
208 PEACOCK LN, HOLMES BEACH, FL 34217
$1,250,000392 Days on yellowkey MLS ID: A4651677
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1738 Built: 1976 Tax: $10,455 (2024)Community: Aufra RepApartment
Taxes:$10,455
Remarks: This property is best suited for buyers seeking short-term rental income, a flexible second home, or a long-term investment in a desirable Holmes Beach location on Anna Maria Island. This well-maintained duplex is ideally located near the island’s renowned Gulf beaches, dining, and shopping, with each side offering 2 bedrooms and 2 bathrooms designed for comfortable island living. Currently operating as an active short-term rental, the property provides immediate income potential while allowing personal use as desired, making it attractive to investors and vacation-home buyers alike. Both sides feature spacious private backyards with room to enhance outdoor living and the potential to add a pool (subject to city approval), offering additional upside in both enjoyment and rental performance. With its proven rental history, flexible use options, and sought-after island setting, this duplex presents a compelling opportunity to own income-producing property on Anna Maria Island.
4118 5TH AVE, HOLMES BEACH, FL 34217
$2,400,00075 Days on yellowkey MLS ID: A4687756
REDUCED by $95,000 (3.8%) on 04/22/2026
Bed: 6 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2786 Built: 2009 Tax: $12,482 (2025)Community: Villas On Fifth AveSpa: YesSingle Family
Taxes:$12,482
Remarks: Welcome to your dream coastal retreat on Anna Maria Island—where luxury, location, and income potential come together seamlessly. This stunning 6-bedroom, 4-bathroom elevated home is a rare find—a property of this size and scale can no longer be built in Holmes Beach. Perfectly positioned just steps from the public beach and turquoise waters of the Gulf, as well as nearby restaurants, shopping, and local attractions, this Mediterranean-style home delivers the ultimate island lifestyle. Thoughtfully designed for both comfort and high-performing investment, it boasts an exceptional rental history to match. Inside, you’ll find a spacious, thoughtfully designed layout ideal for hosting large groups and families. The home features an open floor plan, high ceilings, spacious bedrooms, a 4-person elevator, and multiple balconies, including private outdoor spaces off both primary suites and an additional balcony off the kitchen—perfect for morning coffee, sunset cocktails, or simply enjoying the coastal breeze. The heart of the home opens into a bright, airy living space, complemented by lower level bonus game room that adds an extra layer of entertainment and flexibility. An elevator provides seamless access to all three levels, while ample storage throughout ensures everyday comfort and convenience. Step outside to your own private paradise—a true backyard oasis featuring a sparkling pool, relaxing jacuzzi, a covered dining area, and a spacious conversation lounge—offering the perfect setting to unwind and entertain after a day at the beach. Major recent upgrades (2025), totaling over $100,000, include a new terracotta tile roof, a new pool pump and heater, updated soffits and fascia, and refreshed and reenforced rear decking—providing peace of mind and long-term value. Additional highlights include: Parking for up to 6 vehicles—a rare island luxury Proven rental income with 10 years of consistent, stellar reviews Strong rental projections exceeding $150,000 annually Whether you're searching for a high-performing investment property, a second home, or a full-time coastal escape, this Anna Maria Island gem checks every box.
Listing Agent: Adrienne Carter (310-428-0200)
506 58TH ST, HOLMES BEACH, FL 34217
$3,300,000135 Days on yellowkey MLS ID: A4679359
REDUCED by $100,000 (2.9%) on 04/19/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3319 Built: 1963 Tax: $24,569 (2024)Community: Holmes Beach 14Th UnitSpa: YesSingle Family
Taxes:$24,569
Remarks: Nestled along a serene canal and embraced by a curtain of mature tropical palms, this custom-remodeled residence unfolds as a private coastal estate—an intimate sanctuary where luxury, tranquility, and effortless island living exist in perfect harmony. Masterfully re-imagined by Eason Builder Group, the home was completely gutted and rebuilt just four years ago, and last year the entire first level was once again fully renovated, resulting in a residence that feels both newly crafted and timelessly refined. From the moment you arrive, a sense of seclusion and calm sets in. As you walk up to the home, an old-growth Gumbo Limbo greets you. Sunlight filters through new hurricane-impact windows, illuminating interiors designed to feel open yet intimate, grand yet soothing. The main living space becomes a natural gathering place, anchored by a custom-built-in entertainment center and a coffee station. An elegant touch that invites slow mornings, refined evenings, and effortless entertaining. Sonos surround sound flows throughout the home, creating an ambient soundtrack for daily life, while a fully integrated security and camera system offers peace of mind and quiet confidence. The kitchen stands as a statement of both beauty and performance, where quartz countertops, solid-wood glass-front cabinetry, a sculptural range hood, designer pendant lighting, and stainless-steel Bosch appliances come together in a space crafted for culinary artistry and connection. It opens seamlessly to the dining area, where a wood-burning travertine stone fireplace adds warmth and architectural presence, setting the stage for candlelit dinners and lingering conversations. Two luxurious primary suites, one on each level offers the rare indulgence of privacy and flexibility. Each is finished with shiplap walls, porcelain tile, recessed lighting, and abundant natural light. The upper-level retreat opens to a private balcony overlooking the pool and tropical grounds, a serene perch for sunrise reflections and evening breezes. Its spa-inspired ensuite features a quartz walk-in shower, while the first-floor primary bath is appointed with a solid-wood double vanity, continuing the home’s narrative of tailored craftsmanship and understated elegance. Completing the residence are two additional bedrooms with a shared bath and an upstairs bonus room ideal for recreation, fitness, or creative pursuits. Beyond the interiors, the estate reveals its most captivating chapter. The backyard unfolds as a secluded resort, where a glistening pool and spa are framed by layered, well-established tropical landscaping that has matured into a living wall of privacy. Covered and open-air lounges invite both sun-drenched afternoons and starlit evenings, while a turf-lined grilling and gathering area provides an elevated setting for alfresco dining. Just beyond the palms, the canal stretches quietly behind the property, creating the illusion that the waterway is an extension of your own grounds and inviting a lifestyle of boating, paddleboarding, and sunset cruises from your private dock. When you venture beyond this sanctuary, the unmistakable charm of Holmes Beach awaits. This is more than a home—it is a refined island retreat, custom crafted for those who seek privacy, comfort, and tranquility, with the rare privilege of a secluded waterfront setting and immediate access to one of Florida’s most cherished beach communities.
26 SEASIDE CT, HOLMES BEACH, FL 34217
$699,000145 Days on yellowkey MLS ID: A4678364
REDUCED by $11,000 (1.5%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 978 Built: 1964Monthly Fee: $150 Tax: $9,513 (2024)Community: Seaside Gardens RepTownhouse
Taxes:$9,513
Remarks: THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING OUR PREFERRED LENDER! Tranquil waterfront canal townhome on Anna Maria Island in Holmes Beach! Welcome to this beautifully and completely updated TURNKEY FURNISHED 2-bedroom, 2-bath townhome tucked away on a quiet cul-de-sac. Designed with an open floor plan, the home features tile floors throughout, a stylish plank ceiling, and a light-filled living area where charming jalousie windows frame serene canal views. The kitchen is thoughtfully upgraded with stainless steel appliances, a micro hood, custom tile backsplash, and elegant gold accents, making it both functional and eye-catching. Both bedrooms offer private en-suite baths with dual sinks and glass-enclosed showers, while the primary suite enjoys peaceful water views. A dedicated laundry room provides additional storage, and low association fees add to the home’s appeal. Outdoors, a large open lanai and deck create the perfect setting for entertaining. Newer dock with ladder access for a 24" boat, fishing from your back yard or simply relaxing, with easy access to launch your kayak and explore the Anna Maria waterways or Palma Sola Bay. Ideally located on highly sought after Anna Maria Island and close to the Holmes Beach boat ramp, shopping, dining, tennis and basketball courts, baseball fields, dog park, and playground, this canal-front retreat offers the best of coastal living.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Brandi Furlan (941-894-9888)
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