Location: Holmes Beach
Do Not Show Listings
506 69TH ST, HOLMES BEACH, FL 34217
$1,095,000732 Days on yellowkey MLS ID: A4613878
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1470 Built: 1968 Tax: $8,674 (2023)Community: Bay Palms AddSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,674
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: This beautifully updated 2 bedroom, 2 bath pool home offers comfort, flexibility, and exceptional value in the heart of Holmes Beach, featuring a spacious bonus room that can easily function as a third bedroom, office, game room, bunk room, or creative space tailored to your needs. Now offered at a newly improved price, this property presents an exciting opportunity to own a versatile island retreat just minutes from the beach. Wrapped in mature tropical landscaping, the private backyard oasis is designed for both relaxation and entertaining, complete with a heated pool, outdoor shower, firepit area, and multiple shaded lounging spaces perfect for unwinding after a day in the sun. Inside, the open concept layout enhances the flow between living and dining areas, with pocket sliders that open fully to the spacious rear porch, creating seamless indoor and outdoor living. The fully remodeled kitchen is a true highlight, showcasing crisp white cabinetry, sleek countertops, stainless steel appliances, and a generous island ideal for gathering. The primary suite offers a peaceful escape with a well appointed ensuite bath featuring a walk in shower, double vanity, and accessible design. Additional features include a one car garage with a freshly coated floor. Located just a short golf cart ride from the beach, shopping, and dining, this move in ready home delivers easygoing island living with the flexibility today’s buyers are looking for.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Darcie Duncan (941-779-0304)
5701 CARISSA ST, HOLMES BEACH, FL 34217
$3,295,00070 Days on yellowkey MLS ID: A4688232
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3124 Built: 1968 Tax: $17,433 (2025)Community: Holmes Gulf To Bay DevSingle Family
Taxes:$17,433
Tax Year: 2025
Remarks: Tucked away in a quiet area of the island in a lush, tropical setting just moments from the beach, this beautiful 5BD/4BA residence captures the essence of coastal living with effortless style and thoughtful functionality, offering an exceptional opportunity in a desirable weekly rental zone. Framed by swaying palms and vibrant landscaping, the home welcomes you into a light-filled interior where a spacious living room with soaring ceilings, elegant plantation shutters, and a cozy gas fireplace creates an inviting space to gather and unwind. The open flow continues into a well appointed kitchen equipped with everything the family chef could want including a dining nook, but that family chef will love the scullery area with an additional stove and dishwasher for all the family gatherings. The scullery opens to the exterior where the outdoor grill and pizza oven are right at your finger tips. Two ensuite bedrooms, including a serene primary suite, offer comfort and privacy, while the remaining spacious bedrooms provide generous accommodations for the whole family. Step outside to a private pool area designed for soaking up the Florida sunshine, featuring a pool chiller for year-round comfort and surrounded by ample space for lounging and entertaining, along with two convenient outdoor showers. Practical features abound with natural gas service, a whole house generator, a durable metal roof, impact windows and more. There is also an exterior storage shed for all the beach toys, and abundant parking including two circular driveways on this corner lot. Located in the heart of Holmes Beach this location can’t be beat with a short walk to local shops, eateries and most importantly the sugar white sand and turquoise gulf waters.
101 66TH ST #6, HOLMES BEACH, FL 34217
$775,000121 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
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
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
$499,999124 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)
201 54TH ST, HOLMES BEACH, FL 34217
$2,100,000100 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)
510 69TH ST, HOLMES BEACH, FL 34217
$990,000142 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)
659 KEY ROYALE DR, HOLMES BEACH, FL 34217
$7,350,000265 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 is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Cindy Quinn, Pa (941-780-8000)
445 63RD ST, HOLMES BEACH, FL 34217
$579,00071 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 Agent: Mary Anne Muniz (651-470-7020)
130 50TH ST, HOLMES BEACH, FL 34217
$2,699,000114 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)
3018 GULF DR, HOLMES BEACH, FL 34217
$1,500,000400 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
$1,250,000400 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
$2,400,00083 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
$3,300,000143 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.
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Mike Polachek (941-524-0241)
26 SEASIDE CT, HOLMES BEACH, FL 34217
$699,000153 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)
207 PEACOCK LN, HOLMES BEACH, FL 34217
$1,600,000307 Days on yellowkey MLS ID: A4662159
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1713 Built: 1973 Tax: $22,269 (2024)Community: Aufra RepSingle Family
Taxes:$22,269
Remarks: This completely updated Anna Maria Island 3 bedroom 2.5 Bathroom pool home is situated on a cul-de-sac, and features hurricane-rated windows, metal roof, concrete block construction and garage. Property is in a Weekly rental zone with a successful rental history, making this BEAUTIFUL BEACH HOME a perfect investment property, or family get away. Just 3 short blocks to the white sandy beaches of the GULF OF MEXICO and walkable to restaurants, establishments offering live music and charming shops making driving optional once you arrive! The kitchen and great room features an entire wall of sliding doors opening to the sunny south-facing outdoor living space and heated pool. The Master Retreat also opens to the pool area and features a master bath with walk-in shower, dual sink vanity and walk-in closet. A second Master suite and an additional 3rd bedroom with custom built in bunks make this gorgeous home spacious and functional for your family to comfortably relax both indoors and out. New Kitchen, new appliances, new bathroom vanities, new light fixtures, new pool equipment… and situated on an oversized lot, with an oasis backyard surrounded by tropical landscaping, paver decking, and a heated pool. Home is being sold TURN KEY FURNISHED with decorator finishes! This one won't last!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Lindsey Haymond (913-963-7457)
5807 DE PALMAS AVE, HOLMES BEACH, FL 34217
$1,225,000120 Days on yellowkey MLS ID: A4682858
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1140 Built: 1969 Tax: $12,096 (2024)Community: Neptunes GardensSingle Family
Taxes:$12,096
Remarks: This charming ground-level 3-bedroom, 2-bathroom home with a private pool offers an exceptional investment opportunity in a prime location just minutes from the pristine sandy beaches of Anna Maria Island. Currently heavily booked as a vacation rental, it delivers strong occupancy and consistent cash flow in one of the most desirable short-term rental markets along the Gulf Coast. The inviting private pool area boosts appeal for vacationers, helping drive higher rental rates and year-round demand—especially with Anna Maria Island's proven high-season performance and solid average occupancy trends. Enjoy effortless access to Anna Maria Island's world-famous beaches, turquoise Gulf waters, and the laid-back charm of nearby Bradenton Beach, Holmes Beach, and Anna Maria—all just a short drive away. You're also conveniently close to an array of shopping options, diverse restaurants, cafes, and everyday amenities on the mainland and island, making this spot ideal for guests seeking both relaxation and convenience. Whether you're seeking a vacation rental asset or a smart coastal investment, this storm-tested gem—with its established bookings and unbeatable proximity to the beach—represents serious potential in a sought-after market.
Listing Agent: James Wilson (727-331-4353)
408 71ST ST, HOLMES BEACH, FL 34217
$1,799,000246 Days on yellowkey MLS ID: A4668595
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2037 Built: 1966 Tax: $16,372 (2024)Community: Bay Palms AddSpa: NoSingle Family
Taxes:$16,372
Remarks: Welcome to paradise at Coco Cay! This beautiful 4 bedroom 4 bathroom home has been completely remodeled top to bottom. Brand new hurricane impact windows and doors, a new roof, kitchen, appliances, bathrooms, flooring, paint, furnishings, and even a new pool! This island oasis is move-in ready and only a few blocks from the world-famous beaches of Anna Maria Island. You will notice coastal décor as soon as you step into this island gem. The home provides a spacious open living area with teal accents, stainless-steel appliances, quartz countertops, and a game room conveniently adjacent to the kitchen with a pool table and dartboard. Outside you'll enjoy a screened in porch accessible from the living room, a seating area complete with a firepit, and a huge covered lanai for cooking and dining poolside. Weekly rentals are allowed. Make an appointment for your private showing and see what makes Coco Cay an excellent full-time home or investment property.
Listing Agent: Don Purvis (901-240-2180)
402 71ST ST, HOLMES BEACH, FL 34217
$1,395,000454 Days on yellowkey MLS ID: A4645179
5 Days Off yellowkey (back on 4/6/2026)
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2183 Built: 1965 Tax: $14,131 (2024)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$14,131
Remarks: Under contract-accepting backup offers. INCENTIVE****** Seller to replace roof prior to closing!!!! Welcome to Your Dream Vacation Getaway Surrounded by world-class beaches, fantastic restaurants, and charming shops, this TURN-KEY FURNISHED 4-bedroom, 3-bathroom pool home is perfectly situated in the heart of Anna Maria Island. It is just 3 blocks from the beach! A proven income property with exceptional reviews and bookings in place, this home offers both a serene retreat and a smart investment. Nestled on a spacious corner lot with lush native landscaping and swaying palms, the home features wide covered porches that overlook an outdoor oasis. Step into your private paradise with a sparkling lagoon-style pool and spa. Surrounded by tropical greenery, the built-in spa with water jets, thatched umbrella, and natural stone-tiled deck create a resort-like ambiance. A fun Tiki bar, outdoor shower, and ample lounge space add to the perfect setting for entertaining or relaxing after a day at the beach. Outdoor living continues with a covered porch and shaded dining area, ideal for morning coffee or evening cocktails. Inside, the home boasts a completely remodeled, open-concept living area and a large eat-in kitchen, perfect for gathering with family and friends. The split floor plan includes four private bedrooms and two spacious bathrooms on the main floor. Upstairs, a generous loft offers a third bathroom, a fifth bonus bedroom with a queen bed, and a cozy reading nook. An attached 1-car garage provides convenient storage for all your beach gear and golf cart. Don’t miss your chance to own this tropical retreat. Book your private showing today!
Listing Agent: Dee Munn (407-346-4422)
6005 GULF DR #219, HOLMES BEACH, FL 34217
$739,900142 Days on yellowkey MLS ID: A4679762
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1011 Built: 1980 Tax: $7,704 (2025)Community: Playa EncantadaCondo
Taxes:$7,704
Remarks: New Price Adjustment! Enjoy Coastal Living on Anna Maria Island ! This 2 bedroom, 2 bath, 2nd floor, turnkey furnished condo is located in one of the best & most sought after complexes on the Island. Heated swimming pool, spa, pickleball/tennis courts, shuffleboard court, building elevator & beach are just a few of the condo amenities. The condo overlooks the tennis courts with updated stylish kitchen, quartz countertop, stainless appliances & an open/airy floor plan. Large lanai, crown molding throughout & all tile floors accent this gorgeous condo. Washer & dryer are located inside the unit, plus there is an owner's storage room on the ground level. Kitchen appliances & A/C system new in 2021. Just walk across the street to enjoy the white sandy beach & blue green waters of the Gulf of Mexico. Enjoy living the Florida lifestyle!
Listing is courtesy of: ISLAND REAL ESTATE-ANNA MARIA (941-778-6066)
Listing Agent: Thomas Nelson (941-448-4465)
205 HAVERKOS CT, HOLMES BEACH, FL 34217
$1,525,000112 Days on yellowkey MLS ID: A4683517
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1599 Built: 1975 Tax: $12,097 (2024)Community: Haverkos CourtSingle Family
Taxes:$12,097
Remarks: Welcome to your slice of paradise on beautiful Anna Maria Island! This 3-bedroom, 2-bath island retreat is ideally located just 2.5 blocks from the sugar-sand beaches of the Gulf of Mexico, offering the ultimate coastal lifestyle in one of Florida’s most sought-after destinations. Designed for relaxation and entertaining, the home features an amazing ground-level pool with spa — your own private tropical oasis perfect for soaking up the Florida sunshine or unwinding after a day at the beach. The spacious layout comfortably accommodates family and guests, making every stay feel like a vacation. Enjoy being within walking distance to all that Anna Maria has to offer — charming local shops, great dining, grocery options, and more. Leave the car behind and embrace the true island lifestyle. In addition to being a wonderful personal getaway or primary residence, this property is a great rental home with strong appeal to vacationers seeking location, comfort, and exceptional outdoor living. Its proximity to the beach, walkability, and desirable pool/spa amenities make it highly attractive for short-term rental opportunities. Whether you're looking for an island escape, investment property, or both — this home delivers the very best of Anna Maria Island. 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)
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