Location: Holmes Beach
Do Not Show Listings
243 S HARBOR DR, HOLMES BEACH, FL 34217
$3,000,00043 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,421
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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.
Listing is courtesy of: LESLIE WELLS REALTY, INC. (941-776-5571)
Listing Agent: Leslie Wells (941-776-5571)
303 55TH ST, HOLMES BEACH, FL 34217
$4,495,00035 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
Tax Year: 2025
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
$1,095,000116 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 is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Barbara Sato (941-778-7200)
201 57TH ST, HOLMES BEACH, FL 34217
$1,695,000143 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
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
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
$1,395,000390 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)
2806 GULF DR, HOLMES BEACH, FL 34217
$1,095,00013 Days on yellowkey MLS ID: A4686689
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 1500 Built: 1995 Tax: $14,829 (2025)Community: IlexhurstSingle Family
Taxes:$14,829
Remarks: Effortless Island Living at this elevated 3BD/2BA home, where breezy interiors and sunlit spaces create the perfect island escape just steps from the sand. Located in a highly desirable weekly rental zone, this property offers exceptional flexibility and income potential. Inside, the living and dining area welcomes you with abundant natural light and easy access to the expansive front deck. The kitchen features generous counter space and a breakfast bar, making entertaining effortless, while the split bedroom layout provides comfort and privacy. Downstairs, an oversized garage delivers convenience with tandem space for up to four vehicles, along with plenty of room for beach gear, bikes, and additional storage. The low maintenance outdoor space lets you spend more time enjoying the coastal lifestyle, whether you're heading out for sunset walks or relaxing in the ocean breeze from the deck. With its unbeatable location, strong rental appeal, and inviting coastal feel, this property checks lots of the boxes. Bring your decorator touches and create your personal island vibe. Easy access on and off the island, close to shopping, dining, a trolley stop and the beach is right at your back door. What more or you waiting for? Make this your perfect little slice of island life!
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Darcie Duncan (941-779-0304)
6005 GULF DR #219, HOLMES BEACH, FL 34217
$739,90078 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)
213 71ST ST #A&B, HOLMES BEACH, FL 34217
$1,545,000107 Days on yellowkey MLS ID: A4675569
1 Days Off yellowkey (back on 4/5/2026)
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1716 Built: 1987 Tax: $14,295 (2024)Community: West Wind ShoresApartment
Taxes:$14,295
Remarks: Under contract-accepting backup offers. Turnkey Coastal Duplex | 5-Star Short Term Rental | Proven Rental Income | Short stroll to the Beach. Rarely does a property this well-positioned come to market. This elevated, fully furnished duplex in the heart of Holmes Beach is an established, high-performing short-term rental with a 5-star Airbnb rating and verified income history available upon request. Two private residences, each offering 2 bedrooms, 2 bathrooms, private entrances, and open-concept living with coastal finishes, create a truly flexible investment opportunity. Ideal for maximizing rental income, offsetting ownership costs by occupying one unit, or enjoying as a vacation home that performs. Just a two-minute walk to the beach, this property benefits from strong and consistent guest demand. Year-to-date rental performance reflects this demand, with approximately $50,000 in gross bookings through March 2026, demonstrating strong early-year performance and consistent booking momentum; detailed financials available upon request. Covered parking and generous storage beneath the elevated structure add convenience for both guests and owners. A conceptual rendering for a pool and outdoor lounge is attached, offering clear upside potential, subject to permitting and buyer verification. Proven income, 5-star reputation, premier location, and weekly rental zoning make this a compelling investment opportunity.
Listing is courtesy of: AMI REAL ESTATE INC (941-447-9663)
Listing Agent: Debbie Hynds (941-447-9658)
205 HAVERKOS CT, HOLMES BEACH, FL 34217
$1,525,00048 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)
101 66TH ST #6, HOLMES BEACH, FL 34217
$775,00057 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 InnCondo
Taxes:$8,795
Remarks: Back on the Market - Truly a remarkable property, designed in the style of a charming New England Coastal Inn, this intimate 12-unit, three-story beachfront retreat blends timeless character with modern convenience. An elegant staircase and elevator provide access to Unit #6, ideally positioned on the second floor. This spacious 2-bedroom, 2.5-bath residence features beautiful original wood flooring and crown molding throughout. There are not one—but two—private balconies offering pool views, sweeping Gulf vistas, and unforgettable Sunset skies. One balcony extends from the living room, while the second is accessed from the primary suite, creating the perfect setting for morning coffee or evening relaxation. Enjoy a good book or a glass of wine while listening to the Gulf waves breaking across the sand. Inside, you’ll find built-in closets, an in-unit washer and dryer, and a layout designed for comfort and functionality. The Mainsail Inn operates as a condo-hotel, allowing owners up to 120 days of personal use a year while the professional on-site management team actively rents the unit the remainder of the time. With its prime location directly on the sugar-sand beaches of Anna Maria Island, occupancy levels are typically strong—making this not just a beachfront getaway, but a smart income-producing asset. Even better, ownership means enjoying four months each year in your own beachfront retreat without paying nightly rental rates—while rental revenue often offsets the operating expenses. Offered turnkey, this unit includes everything—furnishings, décor, beach equipment, kayaks, paddleboards, and more. Simply bring your swimsuit and start enjoying beachfront living at its finest. This is the kind of property that checks every box: lifestyle, location, and long-term value.
Listing is courtesy of: WAGNER REALTY (941-383-5577)
Listing Agent: Ed Taaffe (636-346-6165)
34 SEASIDE CT, HOLMES BEACH, FL 34217
$699,900109 Days on yellowkey MLS ID: A4675697
REDUCED by $100,090 (12.5%) on 03/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1278 Built: 1965 Tax: $8,392 (2024)Community: Seaside Gardens RepVilla
Taxes:$8,392
Remarks: Discover the perfect canvas to create your waterfront dream home! This solidly built concrete block corner residence has been mediated and is ready for your finishing touches. One a quiet cul-de-sac with no thru traffic and boasting big water dockage, this property is a boater's paradise—ideal for accommodating larger vessels or multiple watercraft. Water features combine an 8K lb lift, 42 ft seawall, 22x15ft dock, and a small wet slip. Imagine stepping out your back door to direct access to the Intracoastal Waterway, Tampa Bay, and the Gulf of Mexico for fishing, cruising, or simply enjoying sunset views from the water. The hard work has been done, and now it’s your turn to unleash your creativity and tailor this home to your vision. This 2BD/2BA villa features an open floor plan with central kitchen, spacious living area, 2 master suites, interior laundry room and more. This property features a grandfathered-in awning and carport offering plenty of additional outdoor space. Whether you're dreaming of a sleek modern retreat or a cozy coastal escape, the possibilities are endless. Seaside Gardens is a historic community of villas at a great value and one of the most peaceful areas on Anna Maria. This civic association allows you to own a slice of paradise without the restrictions and fees of an HOA. Many community amenities are just around the corner offering a boat ramp, tennis, pickleball, basketball, dog park and more. For savvy investors this property will make a great weekly vacation rental. Homes with this combination of solid construction, prime dockage, and potential don’t come along often!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Stephanie Leitao, Llc (941-773-2677)
449 63RD ST, HOLMES BEACH, FL 34217
$739,990158 Days on yellowkey MLS ID: A4671397
REDUCED by $47,010 (6.0%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 958 Built: 1963Monthly Fee: $150 Tax: $6,621 (2024)Community: Seaside Gardens RepVilla
Taxes:$6,621
Remarks: Welcome to Heliconia House. This adorable 2BD/2BA turnkey vacation villa is the perfect island getaway with a heated swimming pool. From top to bottom no detail was spared! Open floor plan with well appointed kitchen, spacious living area, ensuite master bedroom, large interior laundry room and more. The outdoor space features a covered patio that flows to the heated pool all surrounded by lush landscape creating total privacy. Great community amenities just around the corner offering a boat ramp, tennis, pickleball, basketball, dog park and more. Seaside Gardens is a Civic Association and a fantastic value opportunity to own a single family lot on Anna Maria Island without an HOA or Condo Association. This low $150/ month fee includes common area amenities and sewer/water with no fussy HOA to impress. This active vacation rental offering a turnkey investment. Don't miss out on this perfect little slice of island life!
401 28TH ST, HOLMES BEACH, FL 34217
$1,980,00068 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)
7000 GULF DR #115, HOLMES BEACH, FL 34217
$1,395,00078 Days on yellowkey MLS ID: A4679118
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1259 Built: 1978Monthly Fee: $1,150 Tax: $11,730 (2024)Community: Tiffany PlaceCondo
Taxes:$11,730
Remarks: Imagine waking up to views of sugar sand beaches and the turquoise waters of the Gulf. Imagine no longer as you can enjoy this beachfront lifestyle from this 2 bedroom, 2 bath condo in the Beachfront Condominium complex, Tiffany Place. From the moment you enter the unit you will realize its many upgrades: the polished porcelain tile in the foyer and kitchen, the engineered hardwood flooring throughout the remainder of the unit, the plantation shutters, new kitchen cabinets, Jenn Aire Range, stainless steel appliances, remodeled bathrooms and custom cabinets in the primary bedroom. In 2022 a new air conditioner and electric panel were installed and a new hot water heater in 2025. In 2023, all the windows were replaced with Hurricane Impact proof windows, which prevented any damage from the two 2024 hurricanes and provided a discount in insurance and lowered AC costs significantly. As the condo is in the north wing of the complex, you can enjoy the morning sun while drinking your coffee on the balcony and comfortable shade for your afternoon tea or cocktails. The unit has 2 additional storage closets. Tiffany Place is close to the free Island Trolley which can take you to the many unique shops and restaurants on the island and the Library. Or stay put and just enjoy the beachfront living from your new home. .
Listing is courtesy of: A PARADISE INC REALTOR (941-778-4800)
Listing Agent: Helen Ross (941-524-8214)
213 83RD ST #EAST Villa/Unit A, HOLMES BEACH, FL 34217
$1,270,00095 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)
6300 FLOTILLA DR #81, HOLMES BEACH, FL 34217
$465,000106 Days on yellowkey MLS ID: A4676409
REDUCED by $10,000 (2.1%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1151 Built: 1973Monthly Fee: $833 Tax: $5,786 (2024)Community: Shell PointCondo
Taxes:$5,786
Remarks: One or more photo(s) has been virtually staged. Welcome to Shell Point, a lovely waterfront community in the heart of Holmes Beach. If extra space is what you need this unit has it with the back lanai that is all remodeled part of the air conditioned space. This lovely updated condo is conveniently located near the Holmes Beach Boat ramp, tennis courts, basketball courts , dog park, and all within a short stroll to shopping, fabulous dining and of course the beautiful beaches of Anna Maria Island. This lovely 2 bedroom 2 bath unit has been wonderfully updated with beautiful wood grain tile floors, all new appliances, trim, doors, kitchen cabinets, bathroom cabinets, lights, and ceiling fans. It also boasts new window treatments, and hurricane windows and doors as well. This little "gem" of an island retreat, has extra interior space (extra square feet) with the bonus area that is located off of the living room. This air conditioned interior space has beautiful natural light just pouring in all morning and offers a back door to access the community pool and courtyard which has walking paths. A perfect space that can be used as an office space, reading space, entertainment space , or just a nice gathering space to rest and sip on your morning coffee. This unit is all brand new and just waiting for you to start making it your new island retreat. Washer Dryer hookup can be reinstalled per Lapensee Plumbing.
Listing Agent: Michelle Laade (941-737-9662)
234 85TH ST, HOLMES BEACH, FL 34217
$1,774,999370 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 UnitSingle 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)
101 73RD ST #2, HOLMES BEACH, FL 34217
$700,000159 Days on yellowkey MLS ID: A4669721
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 810 Built: 1980 Tax: $3,478 (2025)Community: Princess Martha AptsCondo
Taxes:$3,478
Remarks: One or more photo(s) has been virtually staged. This is your golden moment! Units 1, 2, 3 are all listed for sale and zoned for nightly rentals. Beachfront boutique building is comprised of only six units. This renovated two-bedroom, two-bath unit has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf of Mexico. This is a rare opportunity as unique buildings like these are few and far between. It could be the ideal place to call home use as a daily rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof was installed in 2025, and the air-conditioning unit in 2022. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Shellie Young, Pa (941-713-5458)
6500 FLOTILLA DR #126, HOLMES BEACH, FL 34217
$685,00088 Days on yellowkey MLS ID: A4678773
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1185 Built: 1978 Tax: $9,027 (2024)Community: Westbay Point & Moorings IiCondo
Taxes:$9,027
Remarks: Beautifully renovated FURNISHED SECOND FLOOR bayfront condominium offering expansive, unobstructed views of Anna Maria Sound in the highly desirable Westbay Point & Moorings community. Positioned to capture sweeping water vistas, this residence delivers the quintessential Florida waterfront lifestyle with sunrise and sunset views, gentle bay breezes, and panoramic scenery visible from nearly every room. The interior has been thoughtfully updated with wood-look tile flooring, two remodeled bathrooms and a guest bath featuring glass-enclosed shower doors. The bright, coastal-inspired kitchen showcases white cabinetry, quartz countertops, and stainless steel KitchenAid appliances, creating an open, airy space ideal for entertaining. Roof and air conditioning system were replaced in 2025 adding comfort and peace of mind. In 2020, the screened lanai was enclosed with HURRICANE IMPACT RATED WINDOWS, enhancing year-round living while maintaining stunning waterfront views. French doors lead directly to the primary suite, where tranquil bay views set the tone for relaxation. The elevated second floor vantage point that truly sets this home apart. Outdoors Westbay Point & Moorings offers resort-style amenities, including tennis and pickleball courts, a heated waterfront pool, a second pool with spa. The community is situated on a private peninsula with lush, park-like tropical landscaping and enjoys one of the highest elevations on Anna Maria Island, a notable advantage for coastal living. The Association is fully reserved, professionally managed with a long-term on-site manager, and the property includes established rental history, with multiple rentals already in place for 2026. The Holmes Beach dog park, skate park, basketball, tennis and pickleball, public boat launch, playground and community activities are just around the corner. The public library, many restaurants, art galleries and shops are very convenient to this location. The world famous sandy beaches of Anna Maria Island are a short drive, bike ride or stroll away. A rare opportunity to own a bayfront residence on Anna Maria Island combining luxury updates, resort amenities, and enduring rental appeal.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Linda Moore (941-737-3581)
531 72ND ST, HOLMES BEACH, FL 34217
$4,500,00033 Days on yellowkey MLS ID: A4685680
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3500 Built: 1959 Tax: $11,428 (2025)Community: Bay Palms Add 8Th UnSingle Family
Taxes:$11,428
Remarks: Spectacular bay views define this recently renovated 4-bedroom, 4-bath waterfront home in Holmes Beach, set on a large bayfront lot with exceptional waterfrontage and sweeping open water vistas. Positioned at the end of a quiet bayside street, the property captures some of the most expansive bay views on Anna Maria Island. Renovated within the past year, the home blends updated finishes with distinctive architectural details and inviting gathering spaces. The main living area features a wood burning fireplace, while large windows and sliding glass doors frame the bay and fill the home with natural light. A tongue-and-groove wood ceiling adds warmth and coastal character throughout the primary living space. The updated kitchen includes built-in appliances, custom cabinetry, and generous prep space, opening to the dining and living areas for easy entertaining. A standout feature is the second-floor great room, an expansive and versatile retreat offering elevated water views and abundant natural light. The space includes 4 day beds, a full bath, and an adjacent artist space, creating flexible accommodations for guests or creative pursuits. Outdoor living takes full advantage of the setting with a private pool and expansive waterfront patio areas overlooking the bay, providing ideal spaces for lounging, dining, and enjoying coastal breezes and stunning sunsets. Located just moments from the beaches, shops, and restaurants of Anna Maria Island, this property offers recent renovations, generous living spaces, and exceptional bayfront views in one of Holmes Beach's most desirable waterfront settings.
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