Location: Holmes Beach
Do Not Show Listings
504 58TH ST, HOLMES BEACH, FL 34217
$1,450,00041 Days on yellowkey MLS ID: A4685187
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1540 Built: 1962 Tax: $10,386 (2025)Community: Holmes Beach Fourteenth UnitSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,386
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Recently renovated 3 bedroom, 2 bath canal front home on a beautiful, deep water, natural-lined mangrove canal with a boat dock. This meticulously cared for home is located on a very quiet street in Holmes Beach. A shady, private paver lined courtyard sits canal side and is a serene spot to escape. PGT Hurricane rated windows & doors installed Oct. 2021, new metal roof installed 2025, new A/C, ductwork & insulation 2025 and all new appliances 2025. Centrally located on the island just steps from Holmes Beach City Park & Public Event Venue, with pickleball courts, a dog park and The Island Library. Walking distance to great dining options & local shopping boutiques. Hop on your golf cart to enjoy the pristine beach & Gulf located just minutes from your door! One car garage and ample driveway parking. This great home is truly "island living" at its best.
Listing is courtesy of: MIKE NORMAN REALTY INC. (941-778-6696)
Listing Agent: Marianne Norman-Ellis (941-685-3393)
511 BAYVIEW DR, HOLMES BEACH, FL 34217
$5,290,000105 Days on yellowkey MLS ID: A4675904
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3353 Built: 2020 Tax: $24,007 (2024)Community: Sunrise ParkSpa: YesSingle Family
Taxes:$24,007
Tax Year: 2024
Remarks: Experience the ultimate island paradise in this practically NEW CONSTRUCTION LUXURY WATERFRONT HOME, thoughtfully designed with solid concrete block construction and cutting-edge design and technology. Spanning over 3,300+ square feet, this stunning residence offers 4 bedrooms and 5 full bathrooms, blending elegance, durability, and effortless coastal living. Perfectly positioned just a few short blocks from the Gulf of America, the home also boasts PANORAMIC Intracoastal waterfront views, creating a rare and breathtaking dual-water lifestyle. The half-elevated design provides peace of mind while enhancing views and architectural appeal. Indoors, no detail has been overlooked. Highlights include a butler’s pantry, an upstairs coffee bar just outside the primary suite, and expansive open-concept living spaces ideal for both everyday comfort and entertaining. The luxurious primary retreat offers a serene escape with spa-inspired finishes and seamless indoor-outdoor flow. Step outside to your private waterfront oasis featuring an infinity pool, hot tub, and a fully equipped outdoor kitchen, all designed to maximize sunset views and coastal breezes. Whether hosting guests or enjoying a quiet evening under the stars, this outdoor space is truly exceptional. With waterfront living, modern luxury, and a premier island location, this home offers everything you could ask for—and more. A rare opportunity to own a refined coastal sanctuary that perfectly balances style, comfort, and location. Schedule your private showing today!
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Shannon O'Brien Kerney (941-737-5153)
105 49TH ST, HOLMES BEACH, FL 34217
$3,750,00048 Days on yellowkey MLS ID: A4683981
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2999 Built: 1940 Tax: $41,424 (2024)Community: JonesSingle Family
Taxes:$41,424
Elementary School: None
High School: None
Middle School: None
Remarks: Beachfront Bliss – Gulf Views from Every Angle! Just one house from the beach, this 4-bedroom, 4-bath coastal stunner delivers postcard-perfect Gulf views straight from the kitchen sink—yes, you’ll actually smile while scrubbing plates! Natural light throughout, high ceilings, 2 sided fireplace, wet bar in the living room, open living area that flows into a chef’s kitchen. Stainless steel appliances, gas stove, double ovens and more! The coastal chic blue countertops and tile throughout for easy beach sand clean up! Step outside to your wrap around balcony to dine and enjoy the gulf breeze. Backyard features your private heated pool that includes a sun shelf. All the bedrooms are spacious and have their own privacy. The primary suite is upstairs with even better views of the Gulf to wake up to. Enjoy your private balcony AND a spiral staircase leading up to the roof top deck, ideal to watch sunsets and dolphins jump in the water. Master bathroom has a huge walk-in shower, soak in tub, dual sinks and a large walk-in closet that includes a safe. The location is central to the island, close to everything and very convenient. 30 day minimum rental period. One house away from the Gulf, this may be the island’s best-kept secret!
Listing Agent: Jason Sato (941-778-7200)
403 75TH ST, HOLMES BEACH, FL 34217
$2,485,000350 Days on yellowkey MLS ID: A4650766
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1655 Built: 1955 Tax: $17,404 (2024)Community: Bay Palms Add Fourth UnitSpa: YesSingle Family
Taxes:$17,404
Remarks: Charming Coastal Cottage in Holmes Beach. Welcome to this newly and meticulously remodeled coastal retreat, ideally located in the heart of Holmes Beach. This one-of-a-kind, artsy beach cottage blends timeless charm with modern elegance and smart technology. Step through the inviting rain glass double doors into a spacious open-concept living, dining, and kitchen area, where a dramatic lighted cupola and vaulted ceilings create a stunning first impression. A custom shell stone fireplace with a wood mantle adds warmth to the cozy seating area—perfect for relaxing or entertaining. The chef’s kitchen is a true showstopper, featuring an oversized, lighted quartz island with seating, beadboard cabinetry, and a custom wave-patterned glass backsplash. High-end appliances include an ILVE Majestic 4-burner gas stove with griddle, GE Café refrigerator, wine fridge, and porcelain farm sink—all designed with entertaining in mind.Craftsmanship continues throughout with custom millwork, shiplap accents, paneled walls, and solid-core doors. Oversized sliding glass doors open to reveal a tropical backyard oasis, complete with a free-form heated pool and spa, paver patio with artificial turf. The lush, mature landscaping with up lighting show off the tall palm trees, perfect for a evening cocktail party under the stars. The southern-facing yard is perfect for dining, lounging, and soaking up the sun. Each of the three bedrooms and 2.5 baths showcases custom chrome period fixtures, retro-inspired sinks, and designer details. Tech-savvy buyers will love the smart home features, including Lutron lighting controls, LED lighting, Sonos sound system, security cameras, and plantation shutters. The property includes a 250-gallon buried propane tank serving the on-demand water heater, gas grill, pool heater, and stove. It’s also generator-ready with existing plumbing and wiring in place. There is city dockage close by for boating enthusiast's This extraordinary home offers a rare blend of beachy charm and luxurious amenities—an absolute must-see!
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)
Listing Agent: Gregg Bayer (941-799-9096)
408 71ST ST, HOLMES BEACH, FL 34217
$1,799,000183 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 is courtesy of: BEACH HOUSE REAL ESTATE LLC (941-216-3793)
Listing Agent: Don Purvis (901-240-2180)
130 50TH ST, HOLMES BEACH, FL 34217
$2,799,00051 Days on yellowkey MLS ID: A4683830
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 Agent: Lisa Tucker (863-206-2938)
620 NORTH POINT DR, HOLMES BEACH, FL 34217
$2,200,000163 Days on yellowkey MLS ID: A4670040
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2570 Built: 1993Monthly Fee: $150 Tax: $16,646 (2025)Community: North Point Harbour Unit TwoSingle Family
Taxes:$16,646
Remarks: Hidden gem on North Point Drive in one of the most exclusive communities on Anna Maria Island. This beautifully remodeled 3 Bed, 3.5 Bath two story home is nestled on a quiet cul-de-sac, offering privacy and tranquility just steps away from the stunning waterfront. The bright and airy layout features vaulted ceiling in the living room and loft area, creating an inviting atmosphere for relaxation and entertainment. The gourmet kitchen, the heart of the home, boasts custom tile and solid wood cabinetry, marble backsplash, a six-burner gas range and an expansive island, perfect for culinary enthusiasts. Each bedroom is an ensuite with walk-in closets, offering privacy and comfort. The primary suite, located on the main level, features a luxurious walk-in shower, built -in medicine cabinets, laundry bin cabinetry, and a double sink vanity. There is a dedicated A/C system for each floor. Step outside to enjoy a large patio that leads to your private dock with a new 12,000 pound boat lift, making it easy to access the beautiful waters of Tampa Bay. Additional outdoor amenities include a kayak lift, fish cleaning station, outdoor shower and kayak storage rack. The property is surrounded by lush, tropical landscaping, enhancing its curb appeal and creating a serene environment. Additionally, a secure gated area for your pets ensures a safe space to play. Community amenities include access to a pool and tennis/racquetball courts, perfect for an active lifestyle. With an elevation of more than 8 feet above base flood elevation, your home is safe and secure, potentially qualifying for favorable flood insurance rates. Don't miss this rare opportunity to own a piece of paradise on Anna Maria Island! Schedule your private showing today.
603 EMERALD LN, HOLMES BEACH, FL 34217
$4,340,000338 Days on yellowkey MLS ID: A4652348
Bed: 5 Bath: 5.5 Gar: 5 Liv Area Sq Ft: 3700 Built: 2024 Tax: $21,278 (2023)Community: Key Royale 11Th AddSpa: YesSingle Family
Taxes:$21,278
Tax Year: 2023
Remarks: Stunning turnkey new construction on Anna Maria Island, located on a serene and rare double channel lot in the Key Royale neighborhood. This spacious residence features 5 bedrooms, 2 on the main level and 3 upstairs, all with en suite and walk-in closets offering ample space for family and guests. The main floor’s primary suite includes a large bathroom with steam shower and beautiful marble tile flooring. Enjoy 2 living spaces, one on the main level and another with a large balcony overlooking the canal on the second floor. The elevator provides easy access to both levels. Convenient laundry with 4 washers and 4 dryers, 2 upstairs and 2 on the main level. Upgraded finishes throughout with wide plank engineered walnut flooring, marble tile in the bathrooms, quartz countertops, 8' high extra thick upgraded doors, and upgraded trim package. The modern kitchen boasts brand new high-end Sub-Zero and Wolf paneled appliances and upgraded cabinetry. Step outside to enjoy covered seating and dining areas, a large saltwater pool and spa with breathtaking canal views, and 2 new composite wood docks with new seawall on this home's rare corner channel access, ideal for water enthusiasts. The property also features garage spaces to accommodate 4 vehicles, and new mature landscaping. The home's interiors are thoughtfully designed with hand-curated, beach inspired furnishings which are included in the sale.
227 S HARBOR DR, HOLMES BEACH, FL 34217
$3,650,00037 Days on yellowkey MLS ID: A4684262
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3274 Built: 2023 Tax: $45,830 (2024)Community: Sportsmans Harbor RevSingle Family
Taxes:$45,830
Remarks: Experience elevated coastal living in this brand-new, designer-finished 4BR/4.5BA luxury home located just a 5-minute walk to the pristine beaches of Anna Maria Island. Thoughtfully crafted with high-end finishes and a bright, open-concept layout, this residence blends modern elegance with relaxed island charm. Currently utilized as a successful short term vacation rental with proven rental revenue. 4 spacious ensuite bedrooms, including three king suites with walk-in showers Gorgeous open living area with abundant natural light and upscale coastal décor Chef’s kitchen featuring modern cabinetry, stone counters, and stainless appliances Private heated pool with in-ground spa, surrounded by lush tropical landscaping Expansive rooftop deck offering panoramic views and unforgettable sunsets Fully furnished with professionally curated interiors Designed for relaxation and entertaining, the outdoor oasis includes a sparkling pool, spa, covered lounging areas, multiple decks including a rooftop deck ideal for sunrise coffee or sunset cocktails. The fenced yard provides privacy while maintaining a breezy, coastal feel. Situated in the heart of Holmes Beach, this home offers walkable access to sugar-sand beaches, local dining, boutiques, and the island’s free trolley. Enjoy the perfect blend of tranquility and convenience in one of Florida’s most desirable beach communities. This unique property can be utilized as primary residence, second home, or high-performing vacation rental investment property. This property delivers luxury, comfort, and strong rental appeal in a premier island location.
Listing is courtesy of: LESLIE WELLS REALTY, INC. (941-776-5571)
Listing Agent: Leslie Wells (941-776-5571)
414 79TH ST, HOLMES BEACH, FL 34217
$1,495,00094 Days on yellowkey MLS ID: A4677980
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1621 Built: 1968 Tax: $16,313 (2025)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$16,313
Remarks: Welcome to your own piece of paradise on Anna Maria Island! This is a BRAND NEW remodel including new metal roof, all new plumbing and electrical, pool/spa and turf and much more! This charming coastal home offers the perfect blend of comfort and island living. Nestled off a quiet street, this property is just a short stroll from the stunning Gulf of Mexico beaches. Featuring 3 bedrooms and 3 bathrooms, its spacious enough for family and guests. One bathroom having access right off the pool for easy access. The open concept living and dining area create an inviting space for relaxation and entertainment. The updated kitchen has modern appliances, quartz countertops and plenty of cabinet and storage space with a large island. Enjoy the Florida sunshine in your private backyard oasis, complete with new turf and a putting green, heated pool/spa and lush landscaping. Your garage provides ample storage space for your beach toys and outdoor gear. Holmes Beach is known for its serene atmosphere and friendly community. This is your chance to own a piece of paradise on Anna Maria Island. Whether you're looking for a permanent residence or a vacation retreat, weekly rentals allowed. Property owners in Holmes Beach can lease a boat slip from the city for $600/year! Schedule your private showing today.
5608 HOLMES BLVD, HOLMES BEACH, FL 34217
$1,050,000387 Days on yellowkey MLS ID: A4645925
1 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 2011 Tax: $14,104 (2024)Community: Barefoot BungalowsSingle Family
Taxes:$14,104
Remarks: Under contract-accepting backup offers. GREAT VACATION rental history with many repeat guests!!!!This charming 3 bedroom 2 bath pool home at the beach could be all yours. Nestled in the heart of Holmes Beach, where you can take a short stroll down Holmes Boulevard to city center where you will find adorable shops and restaurants where you can sit, sip, and dine and enjoy a real small town coastal experience. This lovely bungalow style home features a beautiful private pool with swim up table and a shallow sun deck , all brand new furniture, appliances, AC with an upgrade purification Air scrubber component by Aerus, kitchen counters and base cabinets and pool equipment. This home is very well received by its long standing repeat guests and decorated so adorable with its subtle soft coastal chic colors it is sure to please everyones need for the beach. It is very active and successful vacation rental with ample space for your family fun filled vacations, and when you are not using it yourself you can earn income to help offset the costs. Schedule your private showing. FYI this is a typical island "land condo" with NO HOA, each owner takes care of their own home, they do share the same landscaper by choice.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Michelle Laade (941-737-9662)
114 78TH ST, HOLMES BEACH, FL 34217
$999,9009 Days on yellowkey MLS ID: A4688098
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1556 Built: 1947 Tax: $2,575 (2025)Community: Holmes Beach Dev 3Rd UnitSingle Family
Taxes:$2,575
Remarks: Prime Holmes Beach opportunity just steps to the beautiful beaches of Anna Maria Island. Located on a quiet street in one of Holmes Beaches most desirable areas, this property is all about location, flexibility, and future upside. The existing structure has been impacted by Hurricane Helene and is ready for its next chapter. For investors, builders, or end users looking to capitalize on a high-demand island market, this is a chance to secure a well-positioned parcel with strong long-term potential. Holmes Beach continues to see consistent demand driven by its walkability to the beach, access to dining and shopping, and its appeal as both a second-home and income-producing market. Whether your strategy is to renovate, reposition, or build new, the fundamentals here support the investment. Short distance to the Gulf, close to everything on the island, and situated in an area where quality properties continue to command attention—this is a strategic play in a market where opportunities like this are increasingly limited.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Jeff Jordan (941-224-7657)
243 S HARBOR DR, HOLMES BEACH, FL 34217
$3,000,00044 Days on yellowkey MLS ID: A4684027
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2016 Built: 2024 Tax: $8,421 (2024)Community: Sportsmans Harbor RevSpa: YesSingle Family
Taxes:$8,421
Remarks: This almost brand-new, (2024) fully furnished 4-bedroom, 4.5-bath luxury residence delivers the perfect blend of island relaxation and modern sophistication. Built to the highest standards and unaffected by recent hurricanes, it offers peace of mind along with exceptional design. A charming front entry welcomes you into a bright, open great-room floor plan that seamlessly connects the living area, dining space, and chef’s kitchen. The kitchen features a large entertaining island, premium finishes, and generous seating—ideal for hosting family and friends. The primary suite is a serene retreat with a spa-style ensuite bath, creating a private sanctuary for unwinding after a day in the sun. Two more king bedrooms all with en-suite bathrooms allow privacy for guests. Everyone will love the bunk room also with en-suite bathroom. Step outside to expansive outdoor spaces surrounded by lush tropical landscaping. Enjoy the Florida sunshine by the heated pool and infinity edge spa, relax with a drink in hand, or gather for evening conversations under the stars. The turfed backyard provides a lush area for pets and additional seating areas. The home also features rooftop deck with sweeping intercoastal water views, perfect for taking in unforgettable sunsets. Multiple balconies around the allows you to enjoy the incredible island weather. A spacious 2-car garage provides room for vehicles, a golf cart, and additional storage. Every detail has been thoughtfully designed for comfort, convenience, and effortless island living. Situated in one of Anna Maria Island’s most desirable areas, this home places you moments from everything that makes island life special. Take advantage of the private community boat ramp and quick access to the beautiful waters of Tampa Bay and the Gulf. Currently utilized as a short-term vacation rental with great rental revenue and many 5-star reviews, this home provides a fantastic investment opportunity.
303 55TH ST, HOLMES BEACH, FL 34217
$4,495,00036 Days on yellowkey MLS ID: A4685639
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3356 Built: 2026 Tax: $9,277 (2025)Community: Holmes Beach 11Th UnitSpa: YesSingle Family
Taxes:$9,277
Remarks: Brand new construction completed in 2026, luxury home in the heart of Holmes Beach on beautiful Anna Maria Island, just two blocks from the white-sand Gulf beaches. This fully professionally furnished 4-bedroom, 4.5-bath coastal retreat offers the perfect blend of modern design and island living. The open-concept floor plan features a spacious living area with high ceilings and abundant natural light, flowing seamlessly into a chef’s kitchen equipped with premium Thermador appliances, custom cabinetry, a large center island, and a convenient under-counter ice maker—perfect for entertaining family and guests. Each bedroom includes its own en-suite bath, providing privacy and comfort, while the additional half bath is ideal for visitors. Equipped with an elevator going from the ground floor to the beautiful rooftop deck. Professionally designed and sold turnkey furnished, this home is ready for immediate enjoyment or use as a luxury vacation rental. Owner will be listing it as a brand new short-term rental as well. Step outside to your private resort-style backyard oasis featuring a heated pool and spa, covered lounge area, and a custom putting green surrounded by tropical landscaping and turf along with a beautiful custom deck. Multiple outdoor entertaining spaces create the perfect setting for relaxing after a day at the beach. Located only a short stroll—approximately two blocks—from the Gulf of Mexico, this exceptional property offers easy access to pristine beaches, dining, and shopping while maintaining the privacy of a quiet island neighborhood. Whether you’re seeking a full-time residence, second home, or high-end investment property, this brand new Holmes Beach home delivers luxury, location, and the ultimate Anna Maria Island lifestyle.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sean Sabbia (813-748-8701)
220 82ND ST, HOLMES BEACH, FL 34217
$1,095,000117 Days on yellowkey MLS ID: A4675931
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1972 Built: 2001 Tax: $7,624 (2024)Community: SeagroveSingle Family
Taxes:$7,624
Remarks: This charming 3 bedroom, 2 bathroom home offers a perfect blend of island living and modern comfort. With spacious outdoor living and multiple screened in balconies its perfect for relaxation and perfect Florida weather. The layout is designed for seamless indoor-outdoor living, ideal for entertaining or relaxing with family. The kitchen is equipped with contemporary stainless steel appliances, ample counter space, and storage, making it perfect for culinary enthusiasts. Each bedroom offers comfortable living with generous closet space. Enhance the feeling of openness and light throughout the home. Mature foliage provides privacy and a tropical feel as well as low maintenance. Huge garage for vehicles, including room for island-favorite golf carts. Only a short stroll from the Gulf of Mexico beaches to enjoy beach walks and nightly sunsets. This is an excellent opportunity for those looking to invest in a slice of paradise with the potential for both personal enjoyment and rental income, permitted for weekly rentals. Whether you're seeking a permanent residence, a vacation home, or an investment property, this home combines comfort with the quintessential Florida lifestyle. See attached list of upgrades.
Listing Agent: Barbara Sato (941-778-7200)
201 57TH ST, HOLMES BEACH, FL 34217
$1,695,000144 Days on yellowkey MLS ID: A4673048
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2703 Built: 2007 Tax: $6,648 (2024)Community: Carissa VillasSingle Family
Taxes:$6,648
Remarks: Price Improvement! Welcome to Flip Flop Inn, a wonderful BEACH HOUSE escape tucked away on a quiet street on beautiful Anna Maria Island. This expansive three-level elevated pool home has been thoughtfully updated and offers the perfect blend of comfort, style, and coastal charm. Enter into a spacious foyer with immediate access to the outdoor pool area, garage, and the elevator that conveniently serves all floors. The main living level features an open-concept design with ten-foot ceilings, a chef’s kitchen with new stainless appliances, the dining area, and an expansive living room ideal for gathering with family & guests. The balcony overlooking the pool provides a peaceful spot to enjoy the island breeze & cocktails. This floor also includes a well-appointed guest bedroom, full bath and a bunk room. The top level is dedicated entirely to the private primary retreat. This serene space offers an office nook, an extra-large bedroom with its own balcony perfect for morning coffee, two spacious closets, and a great ensuite bath complete with a soaking tub, dual vanities, a large walk-in shower, and a separate water closet. A convenient laundry room and additional closets are also found on this floor. Outdoor living at Flip Flop Inn is truly exceptional. After a day at the beach, rinse off in the new outdoor shower before enjoying the heated pool and surrounding lounge area. The covered patio space features a full bathroom, a granite countertop bar with a sink and mini refrigerator, a dining area with a grill, and a TV, making it ideal for entertaining or relaxing in the shade. This home is completely turnkey furnished in new modest coastal décor & fresh paint, making it effortless to settle in or begin renting immediately. Recent updates include a new metal roof, two new HVAC systems, hot water tank, recent elevator service, and a new pool pump and heater, providing peace of mind and low-maintenance ownership. Located mid-island in Holmes Beach and situated within a weekly rental zone. Currently in a rental program, with future 2026 bookings conveying, making this home a fantastic investment opportunity. *AND+++ check out the price per-square foot....it is the MOST AFFORDABLE spacious 3/3 home on the market! Flip Flop Inn is only a block from the pristine beaches of Anna Maria Island and within walking or biking distance to great dining and charming shops. Just pack your bags and "flip-flops"... your island BEACH HOUSE awaits. *** COMING SOON...MAY 2026 NEW beautiful lux POOLSCAPE!
Listing Agent: Sabrina Ullmann (203-300-8181)
402 71ST ST, HOLMES BEACH, FL 34217
$1,395,000391 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Dee Munn (407-346-4422)
205 HAVERKOS CT, HOLMES BEACH, FL 34217
$1,525,00049 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)
401 28TH ST, HOLMES BEACH, FL 34217
$1,980,00069 Days on yellowkey MLS ID: A4681048
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1656 Built: 1965 Tax: $15,915 (2025)Community: Sunrise ParkSingle Family
Taxes:$15,915
Remarks: Wake up to coastal living in this beautifully remodeled 3-bedroom, 2-bath canal-front home designed for relaxed island life. Spend your mornings paddle boarding or kayaking from your backyard, afternoons boating with easy access to the Intracoastal, Tampa Bay, and Gulf of America, and evenings unwinding in your private pool and spa. The stylish kitchen features high-end Thor appliances, perfect for entertaining after a day on the water. New flooring throughout, a spacious garage, and dedicated parking for a boat trailer or RV add everyday convenience. Lush tropical landscaping surrounds the property, and the beach is just a quick, easy walk away, bringing the best of waterfront and beachside living together in one exceptional home.
Listing Agent: Amy Ward (386-623-2525)
213 83RD ST #EAST Villa/Unit A, HOLMES BEACH, FL 34217
$1,270,00096 Days on yellowkey MLS ID: A4677598
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1304 Built: 1974 Tax: $12,118 (2025)Community: Holmes Beach 31St Unit AmdSingle Family
Taxes:$12,118
Remarks: Steps to the Beach: A Deluxe Retreat with Massive Rental Power! Why choose between a vacation home and a smart investment? This stunning, fully remodeled villa offers the best of both worlds. Nestled just a short stroll from the sand, this 2-bedroom, 2-bathroom sanctuary w/ private garage is a masterpiece of coastal design. But the beauty is more than skin deep—this property is a proven earner, generating over $69K in rental income since June 2025 alone. The backyard is a private resort, featuring a heated pool with spa features and a one-of-a-kind custom bar with a cascading waterfall—the perfect 'money shot' for your rental listing. Inside, enjoy 1,300+ sq ft of luxury, sold turnkey furnished for immediate enjoyment or continued rental success. With impact-rated everything and a modernized effective age, this villa is as 'set-and-forget' as it gets. Whether you are looking for a personal paradise or a turnkey business with a $100k+ annual potential, your search ends here.
Listing Agent: Lindsey Strickland (941-737-3491)
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