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$6,950,000
2 Beds 3 Baths Gutierrez Sub SubDv. 34217 Zip Code
Back on the market!!!!! Welcome to 103 51st Street. One of the most amazing Gulf front properties in Holmes Beach. Although the address says 51st St, the property is found directly on the Gulf of Mexico. It is over 27,000 square feet with 80 feet of direct gulf front. On the street side there is over 151 feet of frontage on 5th Avenue. 5th Avenue is a unique street. It is not a high traffic street and dead ends at the driveway of your new home. The property is surrounded by lush tropical vegetation and shaded by large Australian Pines. They provide a welcome measure of privacy from prying eyes walking past on the beach. You can see out to the Gulf, but they cannot see into the property. Now we need to talk about the existing home. It was elevated enough to have been untouched by the hurricanes of 2024. The home is a traditional wood sided cottage on a block foundation. It is clad in the original cypress plank siding. All the exterior windows have been replaced with impact resistant glazing. The entire back of the home has large windows and sliding doors. You can watch the sunsets from the huge great room and kitchen, and sometimes even from the bed in the primary bedroom, found at the front of the home. The entire interior has been upgraded and redone. The kitchen and baths were covered in granite and stone. The home has 2 bedrooms and 2 and ½ baths. The entire home is open and inviting and you can enjoy it as it is and not change a thing. Or it could be the perfect place to enjoy your Gulf front property while you plan your forever home on Anna Maria Island. The size of the lot allows the construction of a home with well over 9000 square feet of air-conditioned space. Whatever you choose to do, your spectacular Gulf views will never go away.

103 51st Street, Holmes Beach

$1,095,000
3 Beds 2 Baths Bay Palms SubDv. 34217 Zip Code
~Discover your slice of paradise on Anna Maria. Lovingly named “The Beach House,” this charming 3-bedroom & 2-bathroom single level 1950s cottage is full of island charm. Offering the perfect blend of comfort, convenience, and character, the open layout creates a great space for entertaining family & friends or for enjoying quiet relaxation. Make it your own, thoughtfully updated with NEW neutral features; paint & trim, sleek tile flooring throughout, and beautifully bright baths & showers. The spacious primary bedroom has two large closets and a private en-suite bath. Step outside to the palm filled yard, perfect for unwinding. The back deck is great for morning coffee or afternoon cocktails, grilling, and dining. Rinse off after a day at the beach in the fully enclosed outdoor shower, *there is also plenty of property to add a future pool. This lovely home also has a durable metal roof and mature landscaping. LOCATION is everything...in the heart of Holmes Beach, just a block from a beloved beach access and only a short distance to great island shops & dining. Just pack your bags, “The Beach House” is offered turnkey furnished. Currently enjoyed for many years as a 2nd home, use as your primary residence, vacation getaway, and/or as a lucrative rental investment property. This coastal gem ensures you are never far from the sun, sand, and surf. THIS IS THE ONE, this wonderful BEACH HOUSE can now be yours!

206 75th Street, Holmes Beach

$599,000
2 Beds 2 Baths Seaside Gardens SubDv. 34217 Zip Code
Canal-Front Investment Opportunity! Contractors, investors, and renovators—don't miss this exceptional waterfront opportunity in Holmes Beach! This 2-bedroom, 2-bath canal-front half duplex is ready for its next chapter and offers tremendous upside in one of Anna Maria Island's most sought-after locations. Situated on a deep-water canal with direct access to open water and no bridges, this property is a boater's dream and is located just a few short blocks from the pristine Gulf beaches. Whether you're looking to renovate and resell, create a high-end vacation retreat, or build long-term equity, the location alone makes this property a standout investment. Following storm damage, the drywall has been removed approximately four feet from the floor, allowing the new owner to begin renovations without the expense of demolition. The property is ready to be rebuilt and customized to your vision. Both bedrooms have ensuite bathrooms with updated showers and walk in closets. The back bedroom has a nice canal view. Major improvements already completed include: Re-pipe entire unit (2020) Replacement windows and sliding doors (2020) Carrier 2-ton Coastal Series A/C system (2022) Shingle roof replaced (2012) Flat roof replaced (2024) Seawall cap replaced (2011) Waterfront properties with bridge-free boating access and this level of renovation potential are becoming increasingly difficult to find on Anna Maria Island. Bring your contractor, your imagination, and your plans to transform this diamond in the rough into an exceptional island property. Being sold As-Is. An outstanding opportunity for cash buyers, investors, builders, or anyone looking to create significant value in a prime Holmes Beach waterfront location.

420 63rd Street, Holmes Beach

$775,000
3 Beds 2 Baths Holmes Beach SubDv. 34217 Zip Code
Investor Alert! Prime Anna Maria Island Opportunity in a Weekly Rental Zone! Welcome to 202 Peacock Lane, Unit. A beautifully updated elevated 3-bedroom, 2-bath coastal retreat offering the flexibility to enjoy as a private vacation home, seasonal residence, or income-producing investment. Recent improvements include a newer roof, newer A/C, newer water heater, select hurricane-impact windows, and beautiful bamboo flooring, Updated kitchen and baths creating a move-in-ready property with modern coastal appeal. The home can be purchased furnished or unfurnished, allowing buyers to move right in or begin generating rental income immediately. The spacious, open floor plan is designed for relaxed island living and entertaining. As an elevated home, it offers additional storage and parking underneath while providing peace of mind for coastal living. The backyard also offers room for a future pool (buyers to verify), providing the opportunity to create an even more desirable vacation property and increase rental appeal. Situated in a highly desirable weekly rental zone, this property is an outstanding opportunity for investors seeking strong short-term rental potential or buyers looking for their own private island getaway. Best of all, you're just a short walk to the sugar-sand beaches of Anna Maria Island, along with popular restaurants, boutique shopping, parks, the marina, and many of the area's favorite attractions. Leave the car behind and enjoy the convenience of walking or biking to everything island living has to offer. Whether you're searching for a high-performing vacation rental, seasonal residence, second home, or full-time beach retreat, 202 Peacock Lane, Unit A offers the perfect combination of location, lifestyle, and investment potential in one of Anna Maria Island's most sought-after beach communities. Bonus Opportunity: Looking for additional flexibility or a larger investment? The adjoining property, 202 Peacock Lane, Unit B, is also available for purchase (MLS #A4696880). Purchase one or both to create an outstanding investment portfolio, accommodate extended family, or maximize your vacation rental income potential on beautiful Anna Maria Island. This addition is very appealing to investors because it highlights the rare opportunity to purchase both sides of the duplex while also attracting buyers looking for a family compound or expanded rental income.

202 Peacock Lane Unit A, Holmes Beach

$389,000
1 Beds 1 Baths Palms Condominium The SubDv. 34217 Zip Code
*Vintage income producing elevated corner unit on Anna Maria Island. Vacation rentals approved* Discover the perfect blend of beach lifestyle and investment potential ideally located just a short stroll from the sugar-sand beaches of Anna Maria Island. Whether you're searching for a personal island escape, an income-producing vacation rental, or the flexibility to enjoy both, this property checks all the boxes with 7-day minimum rentals permitted. One of the standout features is the rare private covered garage, offering plenty of space for your vehicles, golf carts, bikes, beach gear, and additional storage, an amenity that's increasingly hard to find on the island. The association fee includes water, sewer, trash, exterior insurance, exterior maintenance, and reserves, making ownership simple and predictable with electricity as the only separate utility. Leave the car behind and enjoy one of the Island's most walkable locations, with the beach, restaurants, shopping, grocery store, and local bars just moments away. Clean, well maintained, and ready to enjoy from day one, this is an outstanding opportunity to own a piece of Anna Maria Island at an attractive price point with the income flexibility today's buyers are looking for.

315 58th Street Unit D, Holmes Beach

$888,000
3 Beds 2 Baths Holmes Beach SubDv. 34217 Zip Code
Exceptional Island Investment Opportunity Just One Block to the Beach! Welcome to 202 Peacock Lane, Unit A, a beautifully remodeled half-duplex perfectly positioned for vacation rental investors, second-home buyers, and those seeking the ultimate Anna Maria Island lifestyle. This spacious three-bedroom, two-bath residence with an impressive three-car garage configuration offers the ideal combination of prime island location, investment potential, and coastal living. Located just a few steps from the sugar-sand beaches of Anna Maria Island, this property is an outstanding opportunity for those seeking a vacation home, short-term rental investment, income-producing property, or full-time beach residence. Completely renovated from top to bottom, this turnkey property features a new roof, new HVAC system, new water heater, new flooring, new walls, and a stunning designer kitchen WITH DEKTON countertops (porcelain), showcasing stainless steel appliances, abundant custom cabinetry, and upgraded countertops. New patio, pavers and driveway, and sidewalk The home also boasts two beautifully updated bathrooms featuring custom vanities and stylish finishes. Nearly everything in this property is new or newer, offering peace of mind and low-maintenance ownership. The spacious layout comfortably accommodates families and groups, making it highly desirable as a high-demand vacation rental property. The expansive garage area includes a two-car tandem garage plus a separate 3 car ove sized garage, lockout garage, providing exceptional space for vehicles, golf carts, beach gear, bicycles, owner's storage, and more. Plus, driveway parking for possible 4 more cars. The versatile space beneath the home (2 car tandem garage space) offers endless possibilities, including a game room, entertainment area, additional living space, or covered parking. Outside, the private fenced backyard offers room to create your own tropical oasis with potential space for a pool (buyer to verify). Location is everything, and this property delivers! Leave the car and golf cart behind you're just steps away from world famous Gulf beaches, waterfront dining, boutique shopping, local attractions, and island entertainment. Everything needed for the perfect island vacation experience is within walking distance, making this property exceptionally attractive to both guests and owners. Sold furnished with a few exclusions. Rental or move in ready! Whether you're expanding your real estate portfolio, searching for a beach investment property, looking for a turnkey vacation rental, or dreaming of owning your own piece of paradise on Anna Maria Island, this exceptional property checks every box. Rarely do island properties this close to the beach offer extensive updates, exceptional walkability, flexible living space, and outstanding rental potential. See list of exclusions - Sold mostly furnished. Bonus Opportunity: Looking for additional flexibility or a larger investment? The adjoining property, 202 Peacock Lane, Unit B, is also available for purchase (MLS #A4696880). Purchase one or both to create an outstanding investment portfolio, accommodate extended family, or maximize your vacation rental income potential on beautiful Anna Maria Island.

202 Peacock Lane Unit B, Holmes Beach

$695,000
2 Beds 2 Baths Holmes Beach SubDv. 34217 Zip Code
Welcome to your dream coastal getaway! As captured in the stunning aerial view, this charming two-bedroom, two-bathroom half duplex boasts a prime location less than two blocks from the white sands of Anna Maria and local shops. The property is purposefully elevated for peace of mind, providing the added benefit of ample ground-level storage and covered parking underneath. Zoned for weekly rentals, this home offers incredible flexibility as a versatile island retreat or a highly desirable vacation destination. Inside, the bright and airy kitchen is beautifully appointed with crisp white cabinetry, gleaming countertops, a breakfast bar with vibrant seating, and modern stainless steel appliances, including a premium gas range for effortless cooking. The coastal aesthetic continues into the restful bedrooms, highlighting a spacious setup complete with low-maintenance tile flooring and large windows that invite plenty of natural light. Whether you are looking for a personal slice of paradise or a flexible property in an unbeatable location, this beachside gem is ready to welcome you home.

3303 6th Avenue Unit B, Holmes Beach

$1,995,000
Holmes Beach SubDv. 34217 Zip Code
Exceptional Corner Lot — Steps to the Beach in Holmes Beach Rare opportunity to build your dream island retreat on this combined double lot, totaling approximately 10,000 sqft on a desirable corner parcel in the heart of Holmes Beach. Just steps from the sugar-white sands and sparkling Gulf waters — and zoned for weekly rentals — this property offers endless possibilities to create a custom coastal residence with ample room for a private pool, outdoor entertaining space, and lush tropical landscaping. Set in a central island location near local restaurants, boutique shopping, and island attractions, it blends the charm of relaxed beach living with outstanding investment potential. Whether envisioned as a luxury primary residence, a vacation getaway, or an income-producing rental, this is a unique chance to secure a spacious piece of paradise in one of Anna Maria Island's most coveted locations.

121 48th Street, Holmes Beach

$699,000
2 Beds 2 Baths 34217 Zip Code
Short Sale. Live a life you don't need a vacation from in this beautifully updated, turnkey-furnished beach villa just STEPS from the sugar-sand beaches of the Gulf. Located on the desirable west side of Holmes Beach, this charming 2-bedroom, 1.5-bath townhouse offers approximately 1,050 sq ft of coastal living with no major roads to cross on your way to the beach. Recently renovated, this home features a stunning new kitchen completed in 2025 with custom cabinetry, granite countertops, and state-of-the-art stainless-steel appliances. Fresh interior paint, new tile flooring throughout, and hardwood stairs create a clean, modern feel with no carpeting to maintain. Additional updates include a NEW ROOF IN 2024 & an A/C SYSTEM INSTALLED IN 2020. Enjoy your morning coffee in the inviting front seating area or unwind in the private fenced courtyard, perfect for grilling, entertaining, or relaxing after a day at the beach. With no condo fees, excellent rental potential, and a prime location just moments from shopping, dining, and everything that makes Holmes Beach exceptional, this property presents an exceptional opportunity as a vacation getaway, investment property, or year-round residence. *** SELLER offering $10,000 credit towards closing costs on an agreed upon contract.

120 52nd Street, Holmes Beach

$1,150,000
3 Beds 2 Baths Holmes Beach SubDv. 34217 Zip Code
Price improvement! Welcome to this modern, yet warm and cozy, 3-bedroom, 2-bathroom home on the north end of Holmes Beach on Anna Maria Island. From the moment you arrive, the estate makes a striking first impression with its notable presence and contemporary landscaping. Updated throughout in 2026, this move-in-ready residence offers almost 1,400 square feet of stylish, single-level living designed for comfort and convenience. The bright and inviting interior features a modern kitchen with updated cabinetry and countertops, Café appliances, new interior shutters throughout, and thoughtful finishes that create a chic coastal feel. Central air conditioning and electric heat provide year-round comfort, making this home ideal as a primary residence, vacation getaway, or investment property. Situated on a generous 0.21-acre lot, the property offers a large backyard with sliding glass door access, providing plenty of space to entertain, relax, or create your dream outdoor setting. There's ample room for a pool and ADU, or additional outdoor living areas. Located on a quiet and friendly, low-traffic street, this home offers a peaceful setting with wonderful neighbors and a true sense of community. Enjoy the tranquility of island living while being just minutes from everything the north end of Anna Maria Island offers. Location truly is everything. You'll love the convenient access to sugar-sand beaches, an 8 minute walk to a public beach, island shopping, local cafes, restaurants, parks, and outdoor recreation. The golf-cart-friendly neighborhood makes it easy to explore and enjoy the island lifestyle. As an added bonus, all furnishings are included with the sale, making this a turnkey opportunity. Don't miss your chance to own an elegant home in one of Anna Maria Island's most desirable locations.

214 85th Street, Holmes Beach

$985,000
2 Beds 2 Baths Holmes Beach SubDv. 34217 Zip Code
Discover the best of island living in beautiful Holmes Beach! Nestled on a quiet street in a peaceful neighborhood, you’ll love the combination of boating access and close proximity to the beach this home has to offer. Elevated with impact windows, this 2-bedroom, 2-bathroom home is turnkey furnished and includes a deeded, unimproved boat slip at the end of 85th Street, perfect for boating enthusiasts and those seeking the ultimate coastal lifestyle. New roof installed in August 2025. The downstairs area has been professionally remediated and renovated, while the upstairs living area remained untouched by hurricanes in 2024. Situated on an expansive 9,000sqft lot, there is ample space to add a pool and create your own private oasis. Whether you’re seeking a primary residence or a tropical getaway, this property is ideal for enjoying Anna Maria Island living. Book your showing today!

221 85th Street, Holmes Beach

$1,449,000
4 Beds 4 Baths Edgemere Sub SubDv. 34217 Zip Code
**ACTIVE Short Term Rental** Financials and Insurance information available upon request. Bookings for 2026 and 2027 in place with strong reviews. 2025 Income $146K with 63% Occupancy (Owners used the Property extensively) still producing $104K NET INCOME.COASTAL INVESTMENT OPPORTUNITY! Elevated duplex. Weekly rentals. One block to the beach. Rare deeded boat slip. Turnkey, Fully Furnished, and Income-Producing from DAY ONE! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach on beautiful Anna Maria Island. This Property offers the ideal blend of personal retreat and exceptional income-producing opportunity, along with private residential beach access to the Gulf of Mexico just one block away. With established rental history, and exceptional guest reviews providing immediate confidence for investors, this turnkey property is ready to generate rental income from day one while offering the flexibility of a personal island getaway whenever the mood strikes. Located just one street from the Anna Maria city limits, where weekly short-term rentals are permitted, it maximizes income potential in one of the island's most desirable locations. Each thoughtfully updated 2-bedroom, 2-bath unit is beautifully furnished with coastal-inspired décor, newer appliances and comfortable mattresses that guests consistently rave about. Simply arrive, unpack, and start enjoying everything island life has to offer. Buy with added peace of mind knowing a pre-listing inspection has already been completed. Highlights include a durable metal roof, well-maintained A/C systems, hurricane impact windows and sliding glass doors (approximately four years old), plus an elevated design with flood barriers for added confidence. Outside, the island lifestyle takes center stage. Private balconies with Adirondack chairs invite morning coffee, sunset breezes and front-row seats to the laid-back rhythm of Holmes Beach. The fully fenced yard, installed just six months ago, creates a welcoming outdoor gathering space, while the side yard grill is perfect for relaxing after a day at the beach. Rinse off in the outdoor shower, store your gear in the owner's storage room and enjoy the convenience of separate laundry and utility rooms with washers and dryers, along with golf cart plug-ins for each unit. The island lifestyle comes fully equipped. Two kayaks, a paddleboard and bicycles are included, making it easy for owners and guests alike to experience the very best of Anna Maria Island. For boating enthusiasts, the story gets even better! A rare deeded boat slip conveys with the property, offering immediate access for launching the included kayaks while presenting the opportunity to create a future dock. It's an uncommon bonus that adds both lifestyle appeal and long-term value. Whether you choose to live in one residence while generating income from the other or maximize your investment by leasing both, this exceptional property offers flexibility, strong rental potential and a collection of amenities rarely found together in a single investment opportunity on Anna Maria Island. Follow your nose to the salt air. Chase another spectacular Gulf sunset. Own your slice of paradise with built-in income potential. No shoes required!

8106 Gulf Drive, Holmes Beach

$1,449,000
4 Beds 4 Baths Holmes Beach SubDv. 34217 Zip Code
COASTAL INVESTMENT OPPORTUNITY! Elevated duplex. Weekly rentals. One block to the beach. Rare deeded boat slip. Turnkey, Fully Furnished, and Income-Producing from DAY ONE! Welcome to island living at its finest at 8106 Gulf Drive, Units A & B, in Holmes Beach on beautiful Anna Maria Island. This Property offers the ideal blend of personal retreat and exceptional income-producing opportunity, along with private residential beach access to the Gulf of Mexico just one block away. With established rental history, and exceptional guest reviews providing immediate confidence for investors, this turnkey property is ready to generate rental income from day one while offering the flexibility of a personal island getaway whenever the mood strikes. Located just one street from the Anna Maria city limits, where weekly short-term rentals are permitted, it maximizes income potential in one of the island's most desirable locations. Each thoughtfully updated 2-bedroom, 2-bath unit is beautifully furnished with coastal-inspired décor, newer appliances and comfortable mattresses that guests consistently rave about. Simply arrive, unpack, and start enjoying everything island life has to offer. Buy with added peace of mind knowing a pre-listing inspection has already been completed. Highlights include a durable metal roof, well-maintained A/C systems, hurricane impact windows and sliding glass doors (approximately four years old), plus an elevated design with flood barriers for added confidence. Outside, the island lifestyle takes center stage. Private balconies with Adirondack chairs invite morning coffee, sunset breezes and front-row seats to the laid-back rhythm of Holmes Beach. The fully fenced yard, installed just six months ago, creates a welcoming outdoor gathering space, while the side yard grill is perfect for relaxing after a day at the beach. Rinse off in the outdoor shower, store your gear in the owner's storage room and enjoy the convenience of separate laundry and utility rooms with washers and dryers, along with golf cart plug-ins for each unit. And...The island lifestyle comes fully equipped! Two kayaks, a paddleboard and bicycles are included, making it easy for owners and guests alike to experience the very best of Anna Maria Island. For boating enthusiasts, the story gets even better! A rare deeded boat slip conveys with the property, offering immediate access for launching the included kayaks while presenting the opportunity to create a future dock. It's an uncommon bonus that adds both lifestyle appeal and long-term value. Whether you choose to live in one residence while generating income from the other or maximize your investment by leasing both, this exceptional property offers flexibility, strong rental potential and a collection of amenities rarely found together in a single investment opportunity on Anna Maria Island. Follow your nose to the salt air. Chase another spectacular Gulf sunset. Own your slice of paradise with built-in income potential. No shoes required!

8106 Gulf Drive Unit A&B, Holmes Beach

$879,000
2 Beds 3 Baths Holmes Beach SubDv. 34217 Zip Code
Experience the ultimate Florida beach lifestyle in this elevated 2-bedroom, 2-bathroom coastal retreat situated just steps from the pristine white sands of the Gulf. This home exudes classic island charm with modern peace of mind, featuring full impact-rated windows and doors along with durable Hardie siding designed for long-lasting beauty and protection. The exterior is anchored by a sprawling paver driveway and professional tropical landscaping, leading to a versatile covered under-house area perfect for shaded relaxation or gear storage after a day on the water. The property also boasts ample garage space that offers incredible flexibility, with plenty of room that could easily be converted into a game room or additional lounge area. Inside, the open-concept living space is bathed in natural light and anchored by rich wood flooring that flows throughout the main areas. The chef-inspired kitchen is well-appointed with warm wood cabinetry, granite countertops, and a suite of stainless steel appliances, all centered around a large breakfast bar that overlooks the dining and living zones. Offered fully furnished for the buyer’s convenience, this home is truly move-in ready and designed for immediate enjoyment. Step through elegant French doors to the expansive covered porch, an ideal setting for al fresco dining and morning coffee in the coastal breeze. Whether you are looking for a primary residence or a seasonal getaway, this turnkey coastal gem offers the rare opportunity to live life just minutes from the water’s edge.

2811 Gulf Drive, Holmes Beach

$1,074,000
3 Beds 2 Baths Ilexhurst SubDv. 34217 Zip Code
Competitively Priced to sell, come see this beautifully maintained home for yourself! Welcome to your slice of Old Florida charm in the heart of Holmes Beach on Anna Maria Island. Just a 2-minute walk to the beach, this turnkey furnished home captures the easygoing coastal lifestyle that makes Holmes Beach so special. With its laid-back island feel, tropical setting and inviting spaces, this property is ideal as a primary residence, second home or income-producing property. Inspired by the character Holmes Beach is known for; cozy beach-town living, tropical surroundings and a relaxed pace - this home perfectly fits right in. Beautifully maintained and ready to enjoy, the home offers a flexible layout with a non-conforming 4th bedroom, an oversized garage with rec-room area, a screened-in Florida room and a covered patio perfect for enjoying the coastal breeze. The outdoor shower, lush landscaping and welcoming outdoor spaces add to the relaxed island appeal. With recent updates to include the roof replaced in 2018, hurricane impact windows in 2020, bathrooms updated in 2019, water heater replaced in 2022, as well as fresh interior paint, wainscoting and epoxy garage flooring completed in 2025 this home is ready for your next worry-free chapter on Anna Maria Island. The seller has also completed a pre-listing 4-point inspection with clean results, offering added peace of mind. Conveniently located near the beach, island dining and local shops, this is a wonderful opportunity to own a lovingly cared-for home in one of the most charming communities on Anna Maria Island. Note: Pool Rendering and estimate in attachments for informational purposes only. This property qualifies for a lender credit when using preferred lender. Inquire for details.

2905 Avenue C, Holmes Beach

$569,000
2 Beds 2 Baths Seaside Gardens SubDv. 34217 Zip Code
New tile flooring installed June 2026. This is what Anna Maria Island living is all about. Located in the desirable Seaside Gardens community, this renovated 2-bedroom, 2-bath home offers spacious rooms, updated interiors, and a relaxed, airy feel. Inside, you’ll find new stainless steel appliances, quartz countertops in both the kitchen and bathrooms and ceramic tile flooring throughout. A newer roof and windows add to the list of thoughtful updates. The generously sized bedrooms provide plenty of room to unwind, while the renovated bathrooms offer a clean, modern finish. A dedicated laundry room with washer, dryer, and ample storage adds everyday convenience. Step outside to a fully fenced backyard—perfect for entertaining friends and family along with a private driveway for on-site parking. Being offered semi-furnished, this home is ready to enjoy as your personal island retreat or as an income-producing rental. Spend your days boating, playing pickleball, or relaxing on the beach, soaking in the turquoise waters and sugar-sand shoreline Anna Maria Island is known for. With community amenities and the Intracoastal Waterway just steps away, it’s easy to enjoy the laid-back island lifestyle. Golf carts and pets are welcome, and the trolley stop near the neighborhood entrance makes exploring the island simple and convenient. A comfortable, well-located home in a sought-after community—this is island living made easy.

445 63rd Street, Holmes Beach

$995,000
Sunrise Park SubDv. 34217 Zip Code
Tucked away on a serene cul-de-sac and surrounded by stunning million-dollar homes, this rare .34-acre buildable lot on Anna Maria Island is your blank canvas for creating the ultimate Florida dream retreat. Imagine a private driveway leading to a generous 2,000 sq/ft buildable footprint, where you can design a two-story home complete with a multi-car garage and pool. Nestled amidst lush woods and mangroves, this property offers the perfect balance of privacy and natural beauty. Dream big—picture adding a widow’s walk to take in breathtaking views of the Intracoastal Waterway’s sunrise and the Gulf of Mexico’s unforgettable sunsets. Just steps away at the end of the street, you’ll find access to one of Florida’s finest white-sand beaches, along with endless opportunities for boutique shopping and upscale dining. State, federal, and city compliance permits were previously obtained, and an approved survey is on hand, making the building process easier than ever. While the Army Corps permit has recently expired, it’s ready for the new owner to reinstate the permits and bring their vision to life. Opportunities like this are incredibly rare on Anna Maria Island—don’t let this chance to design your perfect coastal haven slip away!

28th Street, Holmes Beach

$999,999
4 Beds 3 Baths Holmes Beach SubDv. 34217 Zip Code
Discover this 4 bedroom, 3 bathroom versatile home, perfectly positioned on Anna Maria Island for effortless coastal living. Located on a spacious 0.23-acre lot (approximately 9,988 sq ft), this property offers many possibilities!! If desired, this home can easily be changed back to a duplex with some modifications making it a 3 bedroom, 2 bathroom unit on one side and a cozy mother in law suite that is 1 bedroom, 1 bathroom unit on the other. Whether you're seeking a multi-generational home, a vacation retreat with rental potential, or an income-generating investment, this setup provides flexibility and charm in one of Florida's most desirable beach communities. Ideal for families or entertaining, featuring ample room for comfortable island-style living. Step outside to a backyard with plenty of space to add your dream pool, creating a private oasis for relaxation under the Florida sun. Or keep the awesome Koi pond and zen feels of the backyard. With its prime location, you're just a short stroll from pristine white-sand beaches and gorgeous sunsets. Walking distance to Holmes Beach restaurants and shops. Schedule a showing today!

309 57th Street, Holmes Beach

$559,000
2 Beds 2 Baths Seaside Gardens SubDv. 34217 Zip Code
Discover coastal living at its finest in this inviting half-duplex located in the heart of Holmes Beach, the central gem of Anna Maria Island. Just a short stroll to the sand Gulf beaches, this 2-bedroom, 2-bath home offers the perfect blend of relaxation, convenience, and Old Florida charm. Step inside to an open, light-filled layout ideal for year-round living or lucrative vacation rentals. The spacious living area flows seamlessly into a well-appointed kitchen. Both bedrooms provide ample space and comfort. Modern updates (think fresh finishes, stainless appliances, and coastal decor touches) combine with practical amenities like in-unit laundry, carport and outdoor space for enjoying those famous Florida sunsets. Holmes Beach delivers the quintessential island lifestyle: walk or bike to shops, restaurants, and the free island trolley for easy exploration of Anna Maria and Bradenton Beach. With strong rental demand on this sought-after barrier island, this property presents excellent income potential alongside personal use—whether as a primary residence, second home, or investment. Don't miss your chance to own a piece of paradise in one of Florida's most desirable coastal communities. Schedule a showing today and experience Holmes Beach living firsthand!

428 62nd Street, Holmes Beach

$450,000
34217 Zip Code
Rare office space available in well established commercial building in the heart of Holmes Beach on Anna Maria Island. The office area resides in a commercial condominium equipped with elevator, a public restroom for men and women on the second and third floors. Unit for sale is on the second floor. Sign space available and one parking spot under the building. Plenty of exterior parking with both a street and back door entrance. Building provides diverse occupants of financial planning, medical offices, and construction. Current layout of the 988 square feet is a break room with galley kitchen with updated kitchen cabinets. Furthermore, there are three (3) areas equipped with desk counters accommodating several office spaces as well as one room that contains shelving for miscellaneous storage. Interior is decorated coastal with ship lap walls and large doors with glass. Perfect for a small-medium professional office. Space is directly off the main commercial thoroughfare running North and South on Anna Maria Island. This is the hub of Anna Maria Island with Publix, CVS, Walgreens as well as the largest shopping area on Anna Maria Island all an orange throw across the street. This is a perfect location to service residents and visitors of Anna Maria Island. Owner financing will be considered, act now!

3909 E Bay Drive Unit 115, Holmes Beach

$1,150,000
3 Beds 2 Baths Holmes Beach SubDv. 34217 Zip Code
BEST PRICED CANAL FRONT HOME ON A.M.I. Recently renovated 3 bedroom, 2 bath canal front home on a beautiful, deep water, natural-lined mangrove canal with a boat dock. This meticulously cared for home is located on a very quiet street in Holmes Beach. A shady, private paver lined courtyard sits canal side and is a serene spot to escape. PGT Hurricane rated windows & doors installed Oct. 2021, new metal roof installed 2025, new A/C, ductwork & insulation 2025 and all new appliances 2025. Centrally located on the island just steps from Holmes Beach City Park & Public Event Venue, with pickleball courts, a dog park and The Island Library. Walking distance to great dining options & local shopping boutiques. Hop on your golf cart to enjoy the pristine beach & Gulf located just minutes from your door! One car garage and ample driveway parking. This great home is truly "island living" at its best.

504 58th Street, Holmes Beach

$775,000
2 Beds 3 Baths Anna Maria Island Club SubDv. 34217 Zip Code
Experience the perfect blend of luxury beachfront living and strong investment potential with this rare Gulf-front condo-hotel residence on Anna Maria Island, designed in the timeless style of a charming New England coastal inn. This intimate 12-unit boutique community offers direct access to the sandy beaches of the Gulf of Mexico and delivers one of the most desirable beachfront locations in Florida. Unit #6 is ideally positioned on the second floor and accessed by both an elegant staircase and elevator, offering convenience along with privacy and elevation for enhanced views. This spacious 2-bedroom, 2.5-bath beachfront condo features beautiful original hardwood flooring, crown molding, and a bright open layout designed for coastal comfort. A rare highlight of the residence is its two private balconies, one extending from the living room and the other from the primary suite, providing panoramic Gulf views, pool views, and unforgettable sunset skies—perfect for morning coffee, evening relaxation, or listening to waves rolling onto the shore. The interior is thoughtfully appointed with built-in closets, in-unit washer and dryer, and a fully turnkey package that includes furnishings, décor, beach equipment, kayaks, and paddleboards, allowing for immediate enjoyment without additional setup. As part of a professionally managed condo-hotel investment property, owners benefit from up to 120 days of personal use a year while the on-site management team handles rentals the remainder of the time. With its prime beachfront location on Anna Maria Island, the property consistently achieves strong occupancy rates, making it an attractive income-producing vacation rental investment. Even better, ownership allows you to enjoy months of personal beachfront living annually while rental income helps offset operating costs, creating both lifestyle value and financial efficiency. Offered fully turnkey, this residence checks every box for buyers seeking a luxury beachfront condo on Anna Maria Island, a Gulf-front vacation rental investment property, or a low-maintenance coastal retreat in Florida. Simply bring your swimsuit and start enjoying beachfront living at its finest—where lifestyle, location, and long-term value all come together in one exceptional opportunity.

101 66th Street Unit 6, Holmes Beach

$625,000
2 Beds 2 Baths Holmes Beach SubDv. 34217 Zip Code
**NO HOA** Find me another turnkey island property like this one that is zoned for short term rentals without an HOA... Elevated and fully updated coastal retreat on beautiful Anna Maria Island with NO HOA! Built for peace of mind with a newer metal roof, newer deck, HVAC system with brand new UV light and air scrubber, impact windows and doors with a lifetime warranty. The property has been meticulously maintained with a transferrable termite warranty, updated landscaping, outdoor shower, and covered parking for up to five vehicles. Offered fully furnished and ready for you to enjoy the option of flexible income potential with the ability to short term rent while owning a slice of island life near the Gulf beaches, dining, and laid-back charm of Holmes Beach.

4909 Gulf Drive Unit 6B, Holmes Beach

$990,000
2 Beds 2 Baths Bay Palms SubDv. 34217 Zip Code
This stunning completely renovated 2-bedroom, 2-bathroom home offers 1,500 square feet of bright, open-concept living space designed for effortless island lifestyle. Step inside to find a seamless flow between the gourmet kitchen, dining area, and spacious living room—perfect for relaxing with friends, family gatherings, or simply soaking in the Florida sunshine that pours through large windows. The thoughtful renovation shines through with contemporary finishes, high-quality fixtures, and a fresh, inviting palette that feels brand new yet timeless. Both bedrooms provide comfortable retreats, while the well-appointed bathrooms add a touch of luxury. Situated on a prime lot in desirable Holmes Beach, you'll enjoy generous outdoor space—ideal for morning coffee, evening barbecues, or creating your own tropical oasis. Just moments from the sands of Manatee Public Beach and the calm Gulf waters, this home puts you in the center of Anna Maria Island's relaxed charm: pristine beaches, boutique shops, waterfront dining, and easy access to everything the island offers.

510 69th Street, Holmes Beach

$698,000
2 Beds 2 Baths Seaside Gardens SubDv. 34217 Zip Code
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.

26 Seaside Court, Holmes Beach

$5,250,000
Key Royale SubDv. 34217 Zip Code
Experience exceptional waterfront living in this brand new canal front residence offering 5 bedrooms, 5½ baths, plus a den. Thoughtfully designed with custom wood trim, rich wood flooring, and elegant stone countertops throughout, this home blends refined craftsmanship with modern luxury.Enjoy 100 feet of canal frontage with direct canal access, perfect for boating and water enthusiasts. A private elevator services all levels. There is also a breathtaking rooftop deck with panoramic water and sunset views—ideal for entertaining or unwinding.The outdoor living spaces rival a private resort, featuring custom tropical landscaping, a designer pool and spa, and seamless indoor-outdoor flow. A spacious 5-car garage offers abundant room for vehicles, storage, and recreational gear.

607 Baronet Lane, Holmes Beach

$697,500
Sportsmans Harbor SubDv. 34217 Zip Code
One or more photo(s) has been virtually staged. PRICE REDUCED FOR QUICK SALE! PRIME OPPORTUNITY to build a custom coastal home on this 7,500 sq ft cleared corner lot in the heart of Holmes Beach on Anna Maria Island! Ideally located just a short 6-minute walk to the Gulf’s white sand beaches, this property offers the perfect balance of lifestyle and long-term value. With a maximum building height of 35 feet, a future home could capture beautiful water views of both the Gulf of Mexico and the Intracoastal Waterway, creating a true elevated island living experience. Positioned near local dining, shops, access to a community boat ramp for effortless days on the water. The location supports both everyday enjoyment and strong visitor appeal. Zoned for weekly rentals, the property provides flexibility for personal use, seasonal enjoyment, and income generation. Opportunities with this level of flexibility on Anna Maria Island are very limited. Any renderings or home concepts shown are for illustrative purposes only and are not included in the sale. Buyers should conduct their own due diligence regarding design, permitting, and construction. For investors: The combination of weekly rental zoning, walkable beach access, and potential water views creates a compelling opportunity to develop a high-demand vacation rental in a supply-constrained market. For second-home buyers: Design a private coastal retreat tailored to your lifestyle, with the added benefit of generating income when not in use—allowing your beach home to work for you while you’re away.

237 S Harbor Drive, Holmes Beach