Location: Holmes Beach
Do Not Show Listings
6005 GULF DR #219, HOLMES BEACH, FL 34217
$700,0004 Days on yellowkey MLS ID: A4689996
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1011 Built: 1980 Tax: $7,704 (2025)Community: Playa EncantadaSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,704
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Enjoy coastal living at Playa Encantada on Anna Maria Island, where short-term rentals are permitted! This beautifully maintained second-floor condo features 2 bedrooms and 2 bathrooms and comes fully furnished, making it truly move-in ready. Located in one of the island’s most sought-after beachfront communities, residents enjoy a wide range of amenities including private beach access, a heated swimming pool, spa, tennis and pickleball courts, shuffleboard, elevator access, covered parking, and convenient beach entry just across the street. The unit offers desirable southern exposure with views overlooking the tennis courts. Inside, you’ll find a beautifully remodeled kitchen with elegant quartz countertops, stainless steel appliances, including a spacious double oven and an open-concept layout ideal for entertaining. The primary suite features a generous walk-in closet and a beautifully updated bathroom with a walk-in shower. Crown molding and tile flooring throughout add a refined touch. Additional highlights include an in-unit washer and dryer, a tankless water heater, stainless appliances installed in 2023 and an A/C system installed in 2021. Step out onto the large covered lanai to enjoy Florida’s lush scenery and stunning skies. A private owner’s storage room along with a dedicated parking spot is also included on the ground level. With a two-week minimum rental policy, this property offers excellent potential as an income-producing investment or a relaxing second home. Experience the best of the Florida lifestyle, including convenient private beach access with limited public entry nearby for added privacy. The condo is ideally located near a trolley stop, offering free and easy transportation to nearby restaurants and shops. Call for your private showing today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Hannah Hillyard (941-744-7358)
454 63RD ST, HOLMES BEACH, FL 34217
$899,99952 Days on yellowkey MLS ID: A4684367
REDUCED by $17,001 (1.9%) on 04/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1375 Built: 1962Monthly Fee: $150 Tax: $10,360 (2024)Community: Seaside GardensVilla
Taxes:$10,360
Elementary School: Anna Maria Elementary
High School: Manatee High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Welcome to Villa Mar! A luxury vacation rental directly on Watsons Bayou with open water views. This completely renovated 2BD/2BA corner villa is the largest floor plan in Seaside Gardens and features updated kitchen with waterfall counter, brand new appliances, luxury baths, oversized wood plank tile throughout, impact windows and doors, great storage, newer AC, new roof, and 7 inch PVC baseboards for peace of mind. This lot has an extra wide 2 car carport with built in storage cabinets and shed. A large screened patio is perfect for outdoor entertaining after a long day on the boat. A 27 foot boat dock with electric/water, fish cleaning station and 10,000 lb boat lift complete the package. Great location with tennis, shuffleboard, pickle ball and the dog park just steps away. Active weekly rental business! No HOA and no condo fees. Seaside Gardens is a historic civic association maintaining the communal spaces and a low monthly fee of only $150 includes sewer and water. This is the perfect island getaway!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Stephanie Leitao, Llc (941-773-2677)
26 SEASIDE CT, HOLMES BEACH, FL 34217
$699,00095 Days on yellowkey MLS ID: A4678364
REDUCED by $11,000 (1.5%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 978 Built: 1964Monthly Fee: $150 Tax: $9,513 (2024)Community: Seaside Gardens RepTownhouse
Taxes:$9,513
Remarks: THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING OUR PREFERRED LENDER! Tranquil waterfront canal townhome on Anna Maria Island in Holmes Beach! Welcome to this beautifully and completely updated TURNKEY FURNISHED 2-bedroom, 2-bath townhome tucked away on a quiet cul-de-sac. Designed with an open floor plan, the home features tile floors throughout, a stylish plank ceiling, and a light-filled living area where charming jalousie windows frame serene canal views. The kitchen is thoughtfully upgraded with stainless steel appliances, a micro hood, custom tile backsplash, and elegant gold accents, making it both functional and eye-catching. Both bedrooms offer private en-suite baths with dual sinks and glass-enclosed showers, while the primary suite enjoys peaceful water views. A dedicated laundry room provides additional storage, and low association fees add to the home’s appeal. Outdoors, a large open lanai and deck create the perfect setting for entertaining. Newer dock with ladder access for a 24" boat, fishing from your back yard or simply relaxing, with easy access to launch your kayak and explore the Anna Maria waterways or Palma Sola Bay. Ideally located on highly sought after Anna Maria Island and close to the Holmes Beach boat ramp, shopping, dining, tennis and basketball courts, baseball fields, dog park, and playground, this canal-front retreat offers the best of coastal living.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Brandi Furlan (941-894-9888)
34 SEASIDE CT, HOLMES BEACH, FL 34217
$699,900115 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!
15 SEASIDE CT, HOLMES BEACH, FL 34217
$599,000411 Days on yellowkey MLS ID: A4642333
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 978 Built: 1963Monthly Fee: $150 Tax: $7,635 (2024)Community: Seaside Gardens RepSingle Family
Taxes:$7,635
Remarks: Waterfront opportunity awaits on Anna Maria Island! Discover the potential to craft your ideal coastal retreat in the evolving Seaside Gardens community of Holmes Beach. With direct, no-bridge access to the Gulf, this property is perfectly suited for boating enthusiasts, offering generous dock space and a 2020 seawall backed by a transferable 60-year warranty. Located just a short half-mile from the island’s renowned sugar-sand beaches, you can enjoy sun-filled days and peaceful mornings watching the sunrise over the water. Nearby, you’ll find the best of island living—local restaurants, lively gathering spots, coffee shops, and a marina—all just minutes away. Outdoor amenities, including tennis, pickleball, and basketball courts, along with a convenient boat launch, are right around the corner. Whether you envision building a custom waterfront home overlooking Watson’s Bayou or enhancing the existing structure to unlock its full value, the possibilities here are wide open. With strong short-term rental appeal in a highly desirable location, this is a rare chance to secure your place in paradise.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Shandra Holbrook (502-905-8528)
23 SEASIDE CT, HOLMES BEACH, FL 34217
$599,000512 Days on yellowkey MLS ID: A4629905
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 978 Built: 1963Monthly Fee: $150 Tax: $9,252 (2023)Community: Seaside Gardens RepSingle Family
Taxes:$9,252
Tax Year: 2023
Remarks: HUGE PRICE REDUCTION – now under $600K! NEW ROOF! Investor alert! Opportunities like this on Anna Maria Island are rare, especially at this price point. Here’s your chance to bring your dream home to life in picturesque Holmes Beach within the transforming Seaside Gardens community. This is your blank canvas to create the ultimate waterfront retreat and boater’s paradise, with no bridges to the Gulf and generous dock potential allowing for quick and easy access to open water. The location is unbeatable, just 0.5 miles to the sugar-white sand beaches and even closer to the vibrant heart of Holmes Beach, where you’ll find charming restaurants, lively taverns, coffee shops, a marina, and more. You can even see the nearby boat launch from the property. For those who enjoy staying active, tennis, pickleball, and basketball courts are all just steps away. Wake up to peaceful views of Watson’s Bayou and design your ideal 2-bedroom island escape. Whether you envision a private coastal getaway or a high-performing short-term rental, the possibilities are exceptional. Don’t miss this opportunity—the island lifestyle has never been more attainable.
6400 FLOTILLA DR #56, HOLMES BEACH, FL 34217
$575,000119 Days on yellowkey MLS ID: A4675576
0 Days Off yellowkey (back on 4/17/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 985 Built: 1977 Tax: $8,780 (2024)Community: Westbay Point & MoorCondo
Taxes:$8,780
Remarks: Under contract-accepting backup offers. In the sought-after Westbay Point and Moorings community, this 1,377-square-foot second-floor End unit residence offers an exceptional opportunity to complete a coastal retreat with your custom finishes. This two-bedroom, two-bath condominium is in vanilla shell/box condition, with new sheetrock installed, and major structural and mechanical upgrades completed. Features include a new roof with a tie-down system, new firewall, new air duct system, updated insulation, new electric and plumbing infrastructure, new air handler and new roof-mounted air compressor. All windows have been replaced with hurricane impact-rated glass, including those in the guest bedroom and side elevations. Additional upgrades include a new hurricane-rated front entry door, porch screening system, and laundry room door. Enjoy panoramic water views and an unobstructed view of the Skyway Bridge from this top-floor unit. The residence presents an ideal blank canvas for designing a personalized interior while benefiting from high-cost improvements.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: David Liberatore Pllc (941-900-9995)
8301 MARINA DR #8, HOLMES BEACH, FL 34217
$110,00064 Days on yellowkey MLS ID: A4681411
Bed: Bath: 0.0 Tax: $630 (2024)Community: Boat SlipsDock-Rackominium
Taxes:$630
Remarks: Under contract-accepting backup offers. Rare opportunity to own a premium boat slip with a 7,500-pound boat lift in the highly sought-after boating community of Holmes Beach on beautiful Anna Maria Island. Whether you’re an avid angler, sunset cruiser, or weekend sandbar explorer, this is your chance to secure effortless access to some of Florida’s most spectacular waters. Perfectly positioned for convenience and adventure, this slip allows you to lower your boat and be cruising within minutes. Enjoy direct access to the Intracoastal Waterway, where calm, protected waters make for easy navigation whether you’re heading north toward Tampa Bay or south toward Sarasota. From there, it’s a quick and scenic ride out to the Gulf of Mexico — famous for its turquoise waters, world-class fishing, dolphin sightings, and breathtaking sunsets. Imagine spontaneous afternoons on the water — cruising to waterfront restaurants for lunch, anchoring at nearby sandbars, or casting a line for snook, redfish, grouper, and tarpon. Early morning fishing trips and sunset cocktail cruises become part of your everyday lifestyle. No trailering. No boat ramps. No waiting. Simply arrive, lower your 7,500-lb lift, and go. Anna Maria Island is celebrated for its relaxed coastal charm, old Florida character, and strong boating culture. Holmes Beach offers a central island location with easy access to marinas, waterfront dining, boutique shopping, and pristine white-sand beaches. From exploring Egmont Key to docking at nearby island favorites, the possibilities are endless. Boat slips with lifts of this capacity are exceptionally rare on Anna Maria Island, especially in such a prime location. Limited inventory, high demand, and the island’s protected footprint make opportunities like this few and far between. Whether you’re securing a long-term investment or elevating your boating lifestyle, this slip represents both convenience and exclusivity. If you’ve been waiting for the perfect place to keep your boat ready at a moment’s notice in one of Florida’s most desirable waterfront communities, this is it. Embrace the Anna Maria Island boating lifestyle — effortless days on the water, unforgettable sunsets, and the freedom to explore the Intracoastal and Gulf whenever the mood strikes.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
605 N POINT DR, HOLMES BEACH, FL 34217
$3,395,00055 Days on yellowkey MLS ID: A4683720
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3214 Built: 2012Monthly Fee: $167 Tax: $22,644 (2024)Community: North Point Harbour Unit OneSpa: NoSingle Family
Taxes:$22,644
Remarks: Nestled at one of the highest elevations on Anna Maria Island, this exceptional coastal retreat is located in the highly sought-after North Point Harbour community of Holmes Beach. Built in 2012 with hurricane-rated windows and doors, the home offers both refined elegance and peace of mind, perfectly blending luxury with the relaxed sophistication of island living. A cheerful front porch welcomes you inside, setting the tone for the warmth and charm found throughout. Soaring ceilings and gleaming marble floors create a light, airy ambiance, while coastal architectural details — including multiple porches and charming balconettes — add character and dimension to the design. The beautifully appointed living room is flooded with natural sunlight through two sets of French doors that frame tranquil canal views stretching toward Bimini Bay. These doors open to capture sunny mornings and breathtaking evening sunsets, seamlessly blending indoor and outdoor living. The open floor plan flows effortlessly into the dining and kitchen areas, creating an ideal setting for intimate family meals or hosting guests with ease. The spacious first-floor primary suite serves as a peaceful sanctuary, complete with a lovely ensuite bath and a private deck — perfect for quiet evenings under the coastal sky. Two additional bedrooms are also located on the first floor, including a second ensuite bedroom and a third bedroom with its own bath, offering comfort and privacy for family and visitors alike. Even everyday tasks feel elevated in the expansive and beautifully designed laundry and utility room, conveniently located off the kitchen and garage — a space so thoughtfully appointed it hardly feels like a utility area. The entire second floor is dedicated to a spectacular private suite. This luxurious retreat features two charming balconettes, a large walk-in closet, a spa-like ensuite bath with dual sinks, and a separate office or sitting room — an ideal haven for guests or multi-generational living. Outdoors, boating enthusiasts will appreciate the impressive 20,000-pound boat lift and expansive wraparound dock situated on a short, deep-water canal. With direct access through Bimini Bay to Tampa Bay, the Gulf of Mexico, and the Intracoastal Waterway, this property offers effortless navigation to some of Florida’s most beautiful waters. Life in North Point Harbour is as enriching as it is relaxing. Spend mornings at the nearby Key Royale Golf Club for an early tee time, afternoons joining friends at the community pool or enjoying a friendly match on the tennis courts or padel, and evenings cruising from your private dock into Bimini Bay as the sun melts into the horizon. Here, everyday flows seamlessly from recreation to relaxation, creating a true island lifestyle defined by beauty, convenience, and connection to the water. This extraordinary North Point Harbour residence embodies the very best of elevated coastal living — where thoughtful design, superior craftsmanship, and an unparalleled waterfront location come together to create a truly remarkable island home.
Listing Agent: Becky Sirigotis (941-201-8000)
512 77TH ST, HOLMES BEACH, FL 34217
$2,499,000319 Days on yellowkey MLS ID: A4653661
2 Days Off yellowkey (back on 4/17/2026)
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 AmdSpa: YesSingle Family
Taxes:$10,320
Remarks: Under contract-accepting backup offers. ~~~~~~~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)
207 PEACOCK LN, HOLMES BEACH, FL 34217
$1,600,000249 Days on yellowkey MLS ID: A4662159
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1713 Built: 1973 Tax: $22,269 (2024)Community: Aufra RepSingle Family
Taxes:$22,269
Remarks: This completely updated Anna Maria Island 3 bedroom 2.5 Bathroom pool home is situated on a cul-de-sac, and features hurricane-rated windows, metal roof, concrete block construction and garage. Property is in a Weekly rental zone with a successful rental history, making this BEAUTIFUL BEACH HOME a perfect investment property, or family get away. Just 3 short blocks to the white sandy beaches of the GULF OF MEXICO and walkable to restaurants, establishments offering live music and charming shops making driving optional once you arrive! The kitchen and great room features an entire wall of sliding doors opening to the sunny south-facing outdoor living space and heated pool. The Master Retreat also opens to the pool area and features a master bath with walk-in shower, dual sink vanity and walk-in closet. A second Master suite and an additional 3rd bedroom with custom built in bunks make this gorgeous home spacious and functional for your family to comfortably relax both indoors and out. New Kitchen, new appliances, new bathroom vanities, new light fixtures, new pool equipment… and situated on an oversized lot, with an oasis backyard surrounded by tropical landscaping, paver decking, and a heated pool. Home is being sold TURN KEY FURNISHED with decorator finishes! This one won't last!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Lindsey Haymond (913-963-7457)
215 65TH ST, HOLMES BEACH, FL 34217
$1,529,000340 Days on yellowkey MLS ID: A4652336
Bed: 3 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 2184 Built: 2006 Tax: $11,797 (2025)Community: BeachwalkersSpa: YesSingle Family
Taxes:$11,797
Remarks: SHORT TERM RENTALS One block from the beach! Welcome to Sand Palace on Anna Maria Island! This elevated 3 bedroom, 2.5-bath coastal home offers the perfect blend of relaxation and as a successful rental investment just one block from the sugary sands of the Gulf. Designed for indoor-outdoor living, this tropical oasis features brand new siding, a private, fenced backyard with a heated pool and spa, creating the ultimate sanctuary for family getaways. Inside, the home has been freshly painted and exudes comfort with turnkey furnishings, wood floors, high ceilings, and granite countertops. The gourmet kitchen is equipped with solid wood cabinetry, stainless steel appliances, and a generous island with breakfast bar, ideal for entertaining. Enjoy added luxury with a private elevator, central vacuum, two A/C units, metal roof, and an oversized four-car garage offering ample storage. Expand your living space with two spacious 28' x 11' covered porches, one off the main living area and another off the primary suite. This property is zoned for weekly short-term rentals, making it an exceptional income-producing property. Whether you're seeking a smart short term rental investment, a second home, or a forever island retreat, this home checks all the boxes. Located just steps from the beach and close to shopping, dining, and island attractions, this is coastal living at its finest. Call for your private showing today.
525 68TH ST, HOLMES BEACH, FL 34217
$6,150,000165 Days on yellowkey MLS ID: A4671356
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3574 Built: 2025 Tax: $11,692 (2024)Community: Bay Palms AddSpa: YesSingle Family
Taxes:$11,692
Remarks: Just Completed Coastal Southern Retreat on the Grand Canal! Welcome to 525 68th Street, an elegant newly completed Southern-style residence perfectly positioned along the coveted Grand Canal in Holmes Beach. This 4-bedroom, 4.5-bath masterpiece offers timeless charm blended with modern coastal luxury. Each spacious en suite bedroom exudes comfort and style, while a private study provides the perfect quiet escape. The open-concept chef’s kitchen is designed for entertaining, featuring premium appliances, custom cabinetry, and designer finishes. An elevator connects all levels, leading to expansive porches and a stunning rooftop deck with panoramic views of Tampa Bay and the Gulf of Mexico—ideal for sunset gatherings or morning coffee. Step outside to your private oasis—lush tropical landscaping surrounds a heated pool and spa, creating a serene setting for relaxation or waterfront entertaining. With some of the best boating water on Anna Maria Island and quick access to the Intracoastal and Gulf, this property is a boater’s dream. Beautifully designer-furnished and move-in ready, this home invites you to enjoy island living at its finest—just moments from the charming shops, restaurants, and sugar-sand beaches of Holmes Beach. Spend your holidays in pure coastal elegance!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Charles Buky (941-228-6086)
517 42ND ST, HOLMES BEACH, FL 34217
$1,225,000120 Days on yellowkey MLS ID: A4674830
1 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1590 Built: 2000 Tax: $24,543 (2024)Community: 42Nd Street Coastal CottagesSingle Family
Taxes:$24,543
Remarks: Under contract-accepting backup offers. Discover Sunday Funday, an inviting coastal escape set in the desirable Holmes Beach area of Anna Maria Island. This three-bedroom, three-bath residence blends relaxed island living with refined Mediterranean influences, offering privacy, comfort, and thoughtful design throughout. The outdoor living space is a true highlight. Lush tropical landscaping surrounds the backyard, creating a private oasis ideal for entertaining or unwinding. The heated pool features a cascading stone waterfall and a built-in swim-up table, while the expansive covered lanai invites year-round enjoyment. Accented by a pergola, the space includes a refrigerator, granite serving counter, and dining area—perfect for embracing the island’s indoor-outdoor lifestyle. On the ground level, you’ll find two single-car garages, generous parking, and a covered poolside lounge area. A welcoming foyer leads upstairs to the main living level, where an open, airy layout connects the living, dining, and kitchen spaces. Coastal-inspired finishes include new flooring, crown molding, raised-panel doors, crisp white trim, and a soothing neutral palette. The kitchen has been tastefully updated with white cabinetry, granite countertops, stainless steel appliances, and ample workspace for hosting and everyday living. Two generously sized primary suites each feature walk-in closets and renovated en-suite bathrooms, providing flexibility for guests or extended stays. An additional bedroom, full bathroom, laundry area, and walk-in pantry complete the level. Offered fully furnished, Sunday Funday is a successful vacation rental and truly move-in ready. Located just a short walk from Anna Maria Island’s renowned beaches—complete with public amenities, concessions, and live music—as well as nearby dining and shopping, this property offers convenient access on and off the island. Whether you’re seeking a full-time residence, a second home, or a proven income-producing investment, Sunday Funday is ready to deliver the best of island living. This is a typical island "land condo" with NO HOA Dues, each owner takes care of their own home.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Mary Anne Muniz (651-470-7020)
4307 GULF DR #109, HOLMES BEACH, FL 34217
$469,000122 Days on yellowkey MLS ID: A4675685
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1027 Built: 1974Monthly Fee: $1,242 Tax: $2,866 (2025)Community: Cayman Cay VillasCondo
Taxes:$2,866
Remarks: Steps from the Gulf and newly approved WEEKLY rental policy! Experience the best of Anna Maria Island in this charming, ground-level 2-bedroom, 2-bathroom condo located in a premier Holmes Beach community. This residence perfectly balances modern upgrades with the relaxed, "Old Florida" charm that makes this island world-famous. THE INTERIOR: The heart of this home is the newly remodeled kitchen, featuring crisp quartz countertops, contemporary cabinetry, high-end hardware, and a deep farm sink. Sold fully turnkey, the transition to your new beach life is seamless. OUTDOOR LIVING & PRIVACY: Relax and enjoy your morning coffee on your covered, screened-in lanai which overlooks the sparkling community pool or step out for effortless access to the heated swimming pool for a midday dip! For ultimate seclusion, the primary suite features a rare, private open-air patio. Complete with a private outdoor shower, it is a serene sanctuary perfect for sunbathing or getting lost in a good book COMMUNITY & LOCATION: Located directly across the street from the sugary sands of the Gulf of Mexico, this complex offers a true resort feel with a heated pool, BBQ grilling area, and shuffleboard courts. Whether you’re looking for a permanent residence, a seasonal getaway, or an investment, the flexible rental policy - WEEKLY RENTALS ALLOWED - offers great potential. HIGHLITES: • Prime Location: Easy walk to shopping, dining, and island entertainment, with quick access off-island. • Pet-Friendly: Owners are welcome to bring their pets! • Maintenance-Free: Ground-level entry with no stairs to navigate. ADDITIONAL OFFERINGS: covered parking, LG storage closet, small enclosed area off of BD #2 for office space or additional storage. Don't miss this opportunity to own a piece of paradise where the beach is your backyard and every day feels like a vacation!
Listing Agent: Lindsey Strickland (941-737-3491)
441 63RD ST, HOLMES BEACH, FL 34217
$575,00022 Days on yellowkey MLS ID: TB8491520
1 Days Off yellowkey (back on 4/16/2026)
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)
6808 PALM DR #B, HOLMES BEACH, FL 34217
$764,000222 Days on yellowkey MLS ID: A4664678
REDUCED by $5,000 (0.7%) on 04/15/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 925 Built: 1985 Tax: $10,397 (2024)Community: Clark Spring Lake EstatesSpa: NoHalf Duplex
Taxes:$10,397
Remarks: Welcome to Palm View Lakehouse in Holmes Beach. This fully renovated 2-bedroom, 2-bath ELEVATED half duplex was updated in 2022 and allows for weekly rentals, offering excellent investment potential with nearly $50,000 in year-to-date bookings and almost to $60,000 in bookings in 2024, plus several bookings already secured for next year. The home features luxury vinyl plank flooring throughout, granite countertops, stainless steel appliances, and IMPACT windows and doors, with both bathrooms updated with new tile and vanities. Outside, enjoy a PRIVATE heated saltwater pool, along with a DOCK added in 2023 where you can fish, kayak or paddleboard. Other recent improvements include a AC in 2021 and new garage door in 2025. Close in proximity to the Gulf beaches, dining, and shopping, this property blends island living with convenience and comfort.
Listing is courtesy of: SATO REAL ESTATE INC. (941-778-7200)
Listing Agent: Jessica Batten (941-962-3380)
311 59TH ST #A, HOLMES BEACH, FL 34217
$1,380,00069 Days on yellowkey MLS ID: A4682143
REDUCED by $15,000 (1.1%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1518 Built: 2027 Tax: $1 (2025)Community: Holmes Beach 15Th UnitSingle Family
Taxes:$1
Remarks: Pre-Construction. To be built. 45% down, 10% at drywall, the rest not due until Certificate of Occupancy, and a $10000 closing cost credit for the first buyer to move forward. A big splash for Green Street Builders into the Holmes Beach market. They bring 35+ years of experience, and refreshing coastal elegance at a more affordable price point. Not everyone has $10 million for a beach home, we think you'll like these offerings. This plan has 4 defined sleeping areas per side (including an open air loft), high-functionality, and open concept design with cathedral-like ceilings. Quartz waterfall counters, modern sleek cabinets, lots of glass. Same stuff everyone likes in new construction, just more obtainable. We step outside to the deck overlooking the pool area. Under-roof, a massive, shaded entertaining space. Room for Ping Pong, dining, other games, a great TV set up, lounging, or however you see it. It's a lush, tropical, vacation themed setting for you to enjoy... or for your guests to come back to year after year. See all bedrooms and living areas in attached floor plan.
Listing Agent: Jason Skowronski (941-812-6090)
201 N HARBOR DR, HOLMES BEACH, FL 34217
$4,950,000179 Days on yellowkey MLS ID: A4669504
Bed: 5 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 3928 Built: 1985 Tax: $18,164 (2025)Community: Sportsmans Harbor RevSpa: NoSingle Family
Taxes:$18,164
Remarks: Discover an unparalleled living experience in this architecturally stunning island residence, meticulously renovated in 2022 by Richard Haas of Haas Modern Architecture & Design with bespoke floating stairs seamlessly blending cutting-edge design with luxurious amenities, all set against the backdrop of serene harbor views and near pristine beaches. Modern comprehensive renovation infrastructure: Taken down to the blocks then completed with new electrical and plumbing systems, a robust beam and poured cement, Level 5 finish walls and a high-grade GAF underlayment roof, ensuring durability and peace of mind. This unique location is one of only two homes offering boatable water access and beach views, with the pristine shoreline just two blocks away. Direct harbor access includes a new 2024-installed dock with a Golden boat lift supporting up to 16,000 pounds and 35-foot boats. The 2022 harbor dredging is ideal for maritime adventures. The kitchen boasts sleek quartz countertops, a JennAir six-burner gas stove, top-tier JennAir appliances, and elegant ceiling-reaching cabinets with a walk-in pantry ideal for culinary enthusiasts. Integrated remote-controlled blinds, custom Lyteworks ceiling fans, stunning tile throughout the home and an elevator ensure convenience and comfort at every turn. Plenty of space to add a custom pool, generator-ready setup, 250-gallon buried gas tank, two 21 SEER air-conditioning units for the upper floors and a split air-conditioning unit for the ground level, saltwater softener and two instant water heaters. Luxurious baths to indulge in spa-like settings featuring rain showers, quartz finishes, all Toto toilets, and in the primary bath a smart Toto washlet plus toilet in a private water closet, boasting dual sinks, multiple showerheads and an expansive walk-in custom-built closet. The views are memorable as you wake up, spend your day and go to rest. This property stands as a unique sanctuary, combining design, premium amenities and an enviable location for the discerning homeowner. With a certification of completion date of 2022 meeting the new codes of 2021, beneficial for insurance, this residence is more than just a home, it’s a testament to refined living, offering a harmonious blend of luxury, innovation, an extraordinary island sanctuary designed for those who demand the best.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Shellie Young, Pa (941-713-5458)
2915 AVENUE C, HOLMES BEACH, FL 34217
$1,124,500165 Days on yellowkey MLS ID: A4668577
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1040 Built: 1979 Tax: $12,026 (2024)Community: IlexhurstSpa: YesSingle Family
Taxes:$12,026
Remarks: PRIME LOCATION | BRAND NEW RENOVATIONS | ELEVATED-LUXURY-LIVING | ELEVATOR | FENCED SALTWATER POOL | MOVE-IN READY | Located on a peaceful street and embraced by the natural beauty of a mangrove preserve, this elevated coastal residence delivers privacy, modern luxury, and a coveted Holmes Beach lifestyle. Thoughtfully renovated over seven months between 2023 and 2024 with the owners investing $275,000 in premium renovations and high-end additions, the home blends timeless design with state-of-the-art upgrades—creating a tranquil retreat just moments from award-winning Gulf beaches, local dining, and island conveniences. Inside, sunlit living spaces showcase elegant finishes and open-concept design. The kitchen is a modern showpiece, featuring sleek granite countertops, white shaker cabinetry, under-cabinet lighting, and a reverse osmosis water system. Two spacious bedrooms and two spa-inspired bathrooms offer comfort and style, complemented by plantation shutters, smooth ceilings, and a whole-home water filtration system. No detail has been overlooked—from new electrical wiring and panel with underground service to a NEW GARAGE DOOR AND OPENER (2025) and a fully accessible 750-LB CAPACITY ELEVATOR for effortless living. Outdoors, a private fenced backyard oasis invites relaxation with a BRAND NEW ELEVATED SALTWATER POOL (2025) surrounded by lush tropical landscaping enhanced with $20,000 in new plantings, including orange trees and lavender bushes. The serene mangrove backdrop ensures rare tranquility, natural beauty, and panoramic views from your bedroom. The lower level includes a TWO-CAR TANDEM GARAGE and an additional 480 SQUARE FOOT BONUS ROOM with durable polyaspartic-coated flooring. Currently serving as a spacious room for entertainment this can easily be turned into a gym or extra office space—plus an outdoor shower and additional storage. Zoned for MONTHLY VACATION RENTALS and already having a strong rental history, this property offers both investment appeal and a luxurious personal retreat. Located minutes from the Manatee Bridge, Bridge Street, and the North End of Anna Maria Island, this Holmes Beach jewel captures the essence of refined coastal island living. Don’t miss your slice of paradise — schedule your private tour today!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Dean Hinterstoisser (941-726-0314)
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