Location: Holmes Beach , 34217
Do Not Show Listings
234 85TH ST, HOLMES BEACH, FL 34217
$1,774,999371 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,241
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
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
$700,000160 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
Tax Year: 2025
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
$685,00089 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
$4,500,00034 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
Elementary School: None
High School: None
Middle School: None
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.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Dee Munn (407-346-4422)
6250 HOLMES BLVD #56, HOLMES BEACH, FL 34217
$849,90052 Days on yellowkey MLS ID: A4681823
REDUCED by $15,100 (1.7%) on 03/31/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1536 Built: 1992Monthly Fee: $855 Tax: $10,907 (2024)Community: North Beach Village IiiCondo
Taxes:$10,907
Remarks: BEACHY KEEN… Just steps from the pristine shores of Anna Maria Island, this exceptional townhome is ideal as a weekend escape, a seasonal retreat from Old Man Winter, or a smart investment while retirement plans are still taking shape. Whether you’re tired of renting, dreaming of a coastal getaway, or looking to diversify with Florida real estate, this property checks all the boxes. Inside, you’ll find an updated kitchen designed to delight the family chef, featuring newer stainless-steel appliances, rich granite countertops, and classic shaker cabinetry. Stunning Brazilian rosewood flooring flows throughout the open, inviting floor plan, complemented by a dedicated dining area perfect for relaxed gatherings. A conveniently located first-floor powder room offers added convenience for guests. The expansive lanai off the living area is ideal for outdoor entertaining and provides easy access to the community pool. Upstairs, two spacious ensuite bedrooms each feature a private bath and their own balcony—perfect for morning coffee or unwinding at the end of the day. A two-car garage offers ample space for vehicles and other island essentials. Located less than 500 yards from the Gulf, your new home away from home invites daily beach walks, refreshing coastal breezes, and spectacular sunsets. Enjoy the island’s charming shops, restaurants, and community amenities including tennis, pickleball, and a baseball field. Come for the weekend, stay for the season, or plan for the future—either way, you’ll be glad you made this move.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Richard Capps (941-920-7500)
101 73RD ST #3, HOLMES BEACH, FL 34217
$725,000160 Days on yellowkey MLS ID: A4669729
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1980 Tax: $3,151 (2025)Community: Princess Martha AptsCondo
Taxes:$3,151
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 or to use as a weekly rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof and air-conditioning unit were installed in 2025. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.
213 84TH ST, HOLMES BEACH, FL 34217
$2,250,00062 Days on yellowkey MLS ID: TB8475905
1 Days Off yellowkey (back on 4/2/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2193 Built: 1986 Tax: $23,426 (2025)Community: Holmes Beach 34Th UnitSingle Family
Taxes:$23,426
Remarks: Under contract-accepting backup offers. Positioned on a naturally elevated homesite for enhanced drainage and reduced flood exposure, this custom-built Anna Maria Island retreat delivers the perfect blend of luxury, flexibility, and proven investment potential. Offered turnkey furnished, the residence features 4 bedrooms, 3 full baths, and a layout designed for effortless full-time living or high-performing vacation use. The light-filled main living level showcases soaring cathedral ceilings, an open-concept great room, and retractable glass doors that create seamless indoor-outdoor living to the expansive deck. The chef’s kitchen is built to impress with double ovens, commercial-size refrigerator, custom cabinetry, soapstone countertops, large island seating, and a brand-new ZLINE gas cooktop, all enhanced by suspended track lighting. Recent improvements include fresh interior and exterior paint, fresh sod and landscaping, an upgraded irrigation system, and a new pool heater and pump — delivering true move-in-ready peace of mind. The private primary suite offers a balcony retreat, walk-in closet, soaking tub, and walk-in shower. Two additional upstairs guest rooms share a spacious bath, while the fourth bedroom on the lower level provides direct pool access and an additional full bath — ideal for guests or multi-generational living. Outdoor living steals the show with a heated pool and spa, waterfall feature, gas firepit, built-in seating, and lush tropical landscaping for maximum privacy and year-round enjoyment. Zoned R1 with 30-night minimum rentals and a strong established rental history, this property offers exceptional flexibility for personal use, seasonal escapes, or income production. Located moments from the Gulf beaches, dining, and shopping of Anna Maria Island, this elevated, furnished coastal home is the total package.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)
Listing Agent: Jerry Gemmecke (317-445-2434)
101 73RD ST #1, HOLMES BEACH, FL 34217
$675,000160 Days on yellowkey MLS ID: A4669608
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1980 Tax: $3,402 (2025)Community: Princess Martha AptsCondo
Taxes:$3,402
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 one-bedroom, one-bath unit is a first-floor corner unit that has magnificent views with shells and sand at your back patio that lead you to the private path, which opens to the breathtaking sands of the Gulf. This is a rare opportunity as unique buildings like this are few and far between. It could be the ideal place to call home or as a daily rental. The condominium association fee includes exterior maintenance, cable, water, sewer and trash. One pet allowed with no weight limit. The roof and air-conditioning unit were installed in 2025. Make your appointment today to be one of the premier owners of this boutique beachfront condominium.
303 58TH ST, HOLMES BEACH, FL 34217
$2,449,999125 Days on yellowkey MLS ID: A4674192
REDUCED by $50,001 (2.0%) on 04/02/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2524 Built: 2006 Tax: $26,409 (2024)Community: Casa Bella Of Anna Maria IslandSingle Family
Taxes:$26,409
Remarks: AMAZING LOCATION • COMPLETELY UPDATED • BRAND NEW POOL • BRAND NEW ROOF • TURN-KEY FURNISHED Casa Bella is a spacious and beautifully updated 4-bedroom, 3-bath home offering more than 2,500 sq ft in the heart of Holmes Beach. Located just steps from shopping and dining and only a 5-MINUTE WALK TO BEACH, this property is situated in one of Anna Maria Island’s most desirable WEEKLY RENTAL ZONES, making it an excellent investment opportunity or a ready-to-enjoy personal beach retreat. This home has undergone extensive recent updates, including new wood flooring throughout, a brand-new spool (pool with spa jets), and a brand-new roof. Casa Bella is offered turn-key furnished, featuring a thoughtfully curated collection of artwork and unique furnishings. The coastal-style interior includes a large great room, fully stocked updated kitchen with custom cabinetry, stainless steel appliances, stone countertops, and a spacious dining area. The home comfortably accommodates up to 10 guests, with three bedrooms featuring king beds and a fourth bedroom designed with two twin-over-twin bunk sets—ideal for families or renters. Additional features include A LOWER LEVEL RECREATION ROOM with a ping-pong table, three updated bathrooms with spa-style finishes, 2 owner closets and three screened porch areas, perfect for enjoying morning coffee or evening breezes. Situated on a LARGE CORNER LOT with lush tropical landscaping, the outdoor area offers a private FENCED backyard oasis with ample space for dining, entertaining, and relaxing by the pool. Turn the key and start enjoying the ideal Holmes Beach lifestyle—whether as a personal coastal retreat or a strong VACATION RENTAL PERFORMER, Casa Bella offers flexibility, comfort, and an exceptional location.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Marlen Ryan (941-799-1046)
600 MANATEE AVE #116, HOLMES BEACH, FL 34217
$539,00026 Days on yellowkey MLS ID: A4683381
REDUCED by $10,000 (1.8%) on 04/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1179 Built: 1977 Tax: $2,241 (2025)Community: Westbay Cove ICondo
Taxes:$2,241
Remarks: OWNER VERY MOTIVATED !! West Bay Cove in Holmes Beach! This fully updated condo is being offered turnkey furnished, making it an ideal vacation getaway, income-producing rental, or full-time home in paradise.PICKLE BALL ! The bright corner layout offers open, inviting living spaces and a peaceful setting overlooking the pool, creating the perfect spot to unwind after a day at the beach. Thoughtful updates throughout give the home a fresh, coastal feel that’s ready to enjoy from day one. Westbay Cove is a beautifully maintained waterfront community on the Intracoastal Waterway with stunning Tampa Bay views, lush tropical landscaping, two heated pools, and tennis court. Just a couple of blocks to the beach and close to the trolley line, pier, local dining, and shopping—with convenient on and off island access. Don’t miss your chance to own a slice of Anna Maria Island.Walk to Publix, Shopping, Dining and the Gulf!
Listing is courtesy of: BOYD REALTY (941-750-8844)
Listing Agent: Brenda Boyd May (941-730-8589)
624 DUNDEE LN, HOLMES BEACH, FL 34217
$2,295,000203 Days on yellowkey MLS ID: A4665745
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1799 Built: 1967 Tax: $21,626 (2024)Community: Key Royale 9Th AddSingle Family
Taxes:$21,626
Remarks: Welcome to Southern Exposure! One of the best things about coming to sunny Florida from the cold North is a home with Southern Exposure so you can bask in the sun by this amazing pool all day long! Tranquil, private waterfront sanctuary — 624 Dundee on Key Royale is an impeccably renovated residence offering modern-luxe living by the water. This refined 3-bedroom, 2-bath pool home blends effortless flow with elevated finishes throughout. Meticulous landscaping and elegant paved walkways welcome you, while thoughtful attention to detail is evident in every room. Outdoors, a perfectly scaled heated pool and generous sun terraces are complemented by covered lounge space for sophisticated alfresco living and dining. A fully equipped dock with a 10,000 lb lift invites effortless access to open water, fishing, kayaking, or paddleboarding amid abundant coastal wildlife. Entertain beautifully: a sleek, brand-new kitchen with island opens to the dining area and elongated living room, creating seamless indoor-outdoor flow. The primary suite sits poolside with a private ensuite—ideal for morning swims or coffee on the lanai with sunshine all day! Two additional bedrooms share a well-appointed bath and can easily convert to a chic home office or guest quarters. Perfectly positioned on the island, this home captures the quintessential Anna Maria lifestyle—relaxation, sunlit days, and waterfront adventures—ready to be enjoyed as an exquisite primary residence or a sophisticated addition to your investment portfolio.
Listing is courtesy of: ANNA MARIA LIFE REAL ESTATE (941-567-6253)
Listing Agent: Billi Gartman (941-545-8877)
441 63RD ST, HOLMES BEACH, FL 34217
$575,00017 Days on yellowkey MLS ID: TB8491520
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 890 Built: 1962 Tax: $3,875 (2025)Community: Sea Side GardensTownhouse
Taxes:$3,875
Elementary School: Manatee Elementary School-MN
Remarks: Live the island lifestyle just steps from the beach! This beautifully renovated 2-bedroom, 2-bath townhouse in Holmes Beach offers the perfect blend of charm, comfort, and investment potential. Well located within walking distance to the sugar-sand beaches of Anna Maria Island, local restaurants, shops, and island conveniences. Featuring no HOA, this move-in-ready property is ideal as a primary residence, vacation home, or short-term rental opportunity such as Airbnb or VRBO. Inside, the home has been fully updated with stylish quartz countertops, stainless steel appliances, elegant gold hardware, and light-colored luxury vinyl plank flooring throughout. Additional highlights include a screened-in porch, a private yard space, and a brand-new electric water heater. Whether you're looking for a turnkey coastal retreat or an income-producing island property, this one checks all the boxes.
Listing is courtesy of: BLACK PHOENIX REAL ESTATE LLC (813-777-3840)
Listing Agent: Leah Thompson (585-794-7197)
512 77TH ST, HOLMES BEACH, FL 34217
$2,499,000314 Days on yellowkey MLS ID: A4653661
REDUCED by $300,000 (10.7%) on 04/01/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2796 Built: 2003 Tax: $10,320 (2025)Community: Holmes Beach 31St Unit AmdSingle Family
Taxes:$10,320
Remarks: ~~~~~~~PRICE DROP~~~~~~~NOW is the time to buy this house. Make Anna Maria Island your own with a rare opportunity to own a truly iconic private island residence in Holmes Beach. Designed by celebrated architect Emily-Anne Smith, this distinctive home is recognized for its signature pink exterior, architectural integrity, and enduring coastal character. Set along a deep-water canal with direct access through Bimini Bay to Tampa Bay, the property offers seamless access to Florida waters for boating, sailing, and fishing. The setting feels intentionally residential and private, ideal for those seeking a refined second home or a full-time island residence designed for personal enjoyment rather than rental use. Offering nearly 2,800 square feet of interior living space and an additional 1,000 square feet under roof, the home provides generous proportions and thoughtful separation of spaces. A spacious screened porch overlooks protected mangroves, creating a naturally private backdrop and a peaceful connection to the island environment. Inside, soaring cathedral ceilings, custom millwork, and a classic Craftsman-style fireplace highlight the quality and intention behind the original design. The chef’s kitchen is outfitted with a 6-burner WOLF range, SUB-ZERO refrigerator, BOSCH dishwasher, granite countertops, and a vegetable sink, offering a well-appointed foundation for both everyday living and entertaining. The upper level features a versatile loft that includes a bedroom with ensuite bath, a recreation or lounge area, and a charming hidden treehouse retreat, adding character and flexibility to the home’s layout. The floor plan, construction quality, and architectural details provide an exceptional opportunity for a new owner to thoughtfully tailor the space to their own taste while preserving its timeless coastal appeal. With its architectural pedigree, deep-water boating access, and quiet residential setting, this home invites a new owner to build upon its legacy and create a personalized island retreat that will endure for years to come. Schedule your private showing and experience the setting, serenity, and potential that make this a truly special Florida retreat.
Listing Agent: Kathy Harman (941-900-9828)
3018 GULF DR, HOLMES BEACH, FL 34217
$1,500,000337 Days on yellowkey MLS ID: A4651692
Bed: 5 Bath: 0.0 Liv Area Sq Ft: 2320 Built: 1920 Tax: $14,695 (2024)Community: IlexhurstApartment
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 Agent: Brooke Doucett, Llc (941-586-3522)
208 PEACOCK LN, HOLMES BEACH, FL 34217
$1,250,000337 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.
212 72ND, HOLMES BEACH, FL 34217
$2,985,000343 Days on yellowkey MLS ID: A4651200
Bed: 4 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 2272 Built: 2019 Tax: $23,423 (2023)Community: 7173900; West Wind Shores; Lot 16; Block 21; Pb 7/Single Family
Taxes:$23,423
Tax Year: 2023
Remarks: Newly renovated - Stunning 4-bedroom, 6.5-bath is perfect for beach lovers just a block from the Gulf of Mexico beaches. This island home features a backyard with a private pool and tiki bar, hot tub, BBQ area, covered patio with a foosball table, and a rooftop deck with water views. The main living space, includes a kitchen with a beautiful backsplash and quartz countertops, solid wood cabinets, island seating, couches, and a bright dining room with access to a covered deck overlooking the pool. The third floor hosts the primary bedroom, a private balcony with rooftop deck access, and an ensuite bathroom with a double vanity and a large shower. Outdoor amenities also include a pool, spa, This home is just a quick walk to the beach, and guests can easily take the trolley to Pine Ave for local delicacies, fish at the historic AMI city pier, or kayak in the bay waters.
Listing is courtesy of: ANNA MARIA ISLAND BEACHES RE (941-567-5234)
Listing Agent: Gregg Bayer (941-799-9096)
6250 HOLMES BLVD #47, HOLMES BEACH, FL 34217
$875,00048 Days on yellowkey MLS ID: A4683438
0 Days Off yellowkey (back on 3/28/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1536 Built: 1992 Tax: $4,604 (2025)Community: North Beach Village IiiTownhouse
Taxes:$4,604
Remarks: Under contract-accepting backup offers. Right in the heart of Holmes Beach, this 3-bed, 2.5-bath condo/townhouse is the perfect mix of vacation vibes and smart investment. Just a quick stroll to the sugar-sand beach, with the free trolley stop practically next door. You're steps from great shops, restaurants, and that classic laid-back island feel. Inside it's bright and open with a calm coastal look. Neutral floors and paint. Handy 10x14 bonus room downstairs for an office, gym, or games, plus oversized owner storage so you can lock away your stuff if renting. Owners have poured love into it lately: new 2025 roof, hurricane-rated garage door (garage freshly painted, smooth ceiling, new blinds), new furniture in the living areas, new oven, ~2-year-old dishwasher, fresh curtains/blinds/rod setups, and an enlarged screened porch with new furniture. Outside you've got two big balconies, a private ground deck, four new Adirondack chairs + tables, a grill, plus extras like 2 new bikes, beach chairs, wagon, sun tent, and a pickleball set—ready for island adventures. Fully furnished and turnkey, weekly rentals allowed year-round.
504 68TH ST, HOLMES BEACH, FL 34217
$2,200,00072 Days on yellowkey MLS ID: A4679043
1 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1700 Built: 1961 Tax: $11,700 (2024)Community: Bay Palms AddSingle Family
Taxes:$11,700
Remarks: Under contract-accepting backup offers. Welcome to your private coastal retreat, where luxury, functionality, and waterfront living come together seamlessly. This beautifully remodeled 3 BD, 3 BA residence is being sold furnished, showcasing high-end finishes throughout and exceptional indoor-outdoor living. The highly sought after ground level living is even more attractive with the security of a JMI Flood Prevention system that was professionally installed in 2025. Each door opening and garage are protected. Step inside to the open-concept living/dining and kitchen area. Your attention is immediately drawn to the stunning 4" live edge slab island that is perfect for entertaining. Just as beautiful is the wood cabinetry, sleek quartz counters, gas range, designated wet bar with wine fridge and ice maker. As you step from inside to outside, the living space flows effortlessly into multiple outdoor living areas. Enjoy sunset views from your large private dock, perfect for fishing or just relaxing while watching dolphins and manatees pass by. Boating/kayak enthusiasts will appreciate the 10,000-lb boat lift and private kayak/SUP launch. Enlarged dock also includes electricity and fresh water access. The outdoor space is a true island oasis featuring a saltwater pool and spa, lush/mature tropical landscaping, that is also illuminated with professionally installed lighting in both front and back. A large cabana with a fully built-in outdoor kitchen, ideal for entertaining, completes the outdoor living space. Recent upgrades include a brand new A/C system and tankless hot water heater. A 250 gallon buried propane tank services the pool heater, outdoor grill, hot water heater and 5 burner stove. Other upgrades include a new metal roof and all new impact rated windows and slider doors. All original cast iron plumbing has been replaced along with new electrical underground wiring and panel. Perfect as a primary residence, vacation retreat, or investment property, this home delivers the ultimate in luxury canal-front living on Anna Maria Island.
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
504 59TH ST, HOLMES BEACH, FL 34217
$1,795,00092 Days on yellowkey MLS ID: A4677906
Bed: 3 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 3126 Built: 2006 Tax: $8,402 (2025)Community: Holmes Beach 16Th UnitSingle Family
Taxes:$8,402
Remarks: Live the island lifestyle in this custom-built, ELEVATED canal home located in a quiet, no-HOA neighborhood just minutes from the heart of Holmes Beach. Built in 2006, this well-constructed residence offers peace of mind, privacy, and easy access to everything Anna Maria Island is known for—beaches, local dining, boutique shopping, and waterfront parks. The home features an open, multi-level layout designed for comfortable island living, with three spacious bedrooms, multiple balconies and porches, and CANAL and OPEN-WATER views from several levels. The primary bedroom is privately located on the first living level, offering convenience and separation from the additional bedrooms above. Boating enthusiasts will appreciate the private dock with deep-water access and NO BRIDGE RESTRICTIONS, allowing quick access to open water. Additional features include an ELEVATOR, METAL ROOF, four-car garage, ample storage, and room to add a pool for enhanced outdoor living. As one of the few elevated homes in the area, this property offers notable structural integrity and the opportunity to enjoy Anna Maria Island living with confidence.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jessica Batten (941-962-3380)
506 58TH ST, HOLMES BEACH, FL 34217
$3,400,00080 Days on yellowkey MLS ID: A4679359
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3319 Built: 1963 Tax: $24,569 (2024)Community: Holmes Beach 14Th UnitSingle 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.
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