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4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key
$585,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Completely renovated two-bedroom and two-bathroom walkout (no stairs to take) on Longboat Key! Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully reimagined and rebuilt from the studs, this stunning residence showcases high-end craftsmanship and designer finishes throughout. Every detail has been thoughtfully upgraded, including brand-new electrical systems, plumbing, drywall, insulation, kitchen, bathrooms, fixtures, and finishes—providing the peace of mind and comfort of essentially new construction within an established waterfront community. The bright, open-concept floor plan is flooded with natural light and designed for effortless indoor-outdoor living. The beautifully appointed chef's kitchen flows seamlessly into the living and dining areas, creating an inviting space ideal for entertaining, seasonal gatherings, or everyday enjoyment. A dedicated 220-volt outlet offers convenient electric vehicle charging, adding modern functionality and future-ready convenience. One of the villa's most desirable features is its easy ground-level access with no stairs, making everyday living simple and accessible. Pet lovers will appreciate Windward Bay's generous pet-friendly policy allowing up to two pets, a rare and highly desirable amenity on Longboat Key. Step outside to your private patio retreat surrounded by lush tropical landscaping and mature greenery. Enjoy peaceful mornings with coffee, spectacular sunset skies, and relaxing evenings gathered around the fire pit just moments from beach access. The Gulf of Mexico is only steps away, offering endless opportunities for shelling, beach walks, swimming, paddleboarding, and breathtaking sunsets. Residents of Windward Bay enjoy an unmatched collection of resort-style amenities set across nearly 27 acres of beautifully maintained waterfront property, including: Three beach access points to the powdery sand beaches of Longboat Key. Nearly one-half mile of scenic waterfront walking paths and nature trails. Two heated swimming pools. Six tennis and pickleball courts. Fitness center, sauna, clubhouse, library, and social gathering spaces. Two private marinas with boat slips and jet ski slips (for rent and subject to availability). Private fishing pier with panoramic bay views. Kayak storage and launch areas. Outdoor grilling stations, fire pits, and waterfront gathering areas. Lush park-like grounds with mature tropical landscaping. Whether you're searching for a primary residence, seasonal retreat, second home, snowbird escape, waterfront villa, beach getaway, or investment opportunity, this move-in-ready residence offers an unparalleled combination of location, lifestyle, and value. Ideally located minutes to St. Armands Circle, Sarasota's vibrant arts and dining scene, championship golf courses, boating destinations, waterfront restaurants, and world-renowned Gulf Coast beaches, this exceptional property delivers the very best of Longboat Key living. Experience the ultimate in island living where luxury, comfort, boating, beach access, and resort-style amenities come together in one extraordinary coastal retreat.

4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key

872 North Shore Drive, Anna Maria
$1,650,000
4 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
BEAUTIFUL WATER VIEWS. This four-bedroom, two-bath stilt home with a two-car garage offers magnificent, expansive views of Tampa Bay from every level. Designed to capture the beauty of its surroundings, the home features impact-rated windows and sliding glass doors throughout, complemented by stylish plantation shutters. Tile floors flow throughout both living levels and bedrooms. The first level boasts a spacious living and dining room combination alongside an open kitchen complete with granite countertops, stainless steel appliances, wood cabinetry, and an island cooktop—perfect for entertaining. This level also includes a guest bedroom and a full bathroom with a walk-in shower. On the second level, the primary suite offers a large walk-in closet and an en suite bath with a walk-in shower. Two additional bedrooms are located down the hall, along with a convenient inside laundry closet housing the washer and dryer. Both guest bedrooms enjoy stunning blue water views of Tampa Bay. The true money shot awaits on the third-level rooftop deck, where panoramic views stretch all the way around Anna Maria —the perfect setting for sunrise coffee or sunset gatherings. The spacious backyard provides ample room for a pool, and with some updating, this property could truly shine and reach its full potential.

872 North Shore Drive, Anna Maria

111 9th Street N, Bradenton Beach
$1,065,000
2 Beds ⋅ 2 Baths ⋅ Mira Mar Sub SubDv. ⋅ 34217 Zip Code
Experience the peak of coastal living in this fully turnkey, elevated residence, where the rhythm of the Gulf of Mexico meets refined island design. Offered completely furnished and move-in ready, this two-bedroom, two-bathroom home allows for an immediate transition into the Bradenton Beach shoreline experience. The interior is bathed in natural light, highlighting an open-concept layout with a designer kitchen featuring granite countertops, a custom tile backsplash, and stainless steel appliances. Both bathrooms have been elegantly updated with modern stone finishes and contemporary fixtures. Outside, a sprawling wrap-around deck offers an expansive venue for sunset views and open-air relaxation. The ground level provides significant versatility with a large, covered area for secure parking and storage, alongside a private, fenced retreat featuring a personal spa. With rare commercial zoning, this property offers exceptional potential as a primary residence, a seasonal escape, or a high-performance investment. From the meticulously curated decor to the updated systems, every detail is in place for the next owner to simply arrive and enjoy.

111 9th Street N, Bradenton Beach

1246 Riverscape Street, Bradenton
$599,900
3 Beds ⋅ 2 Baths ⋅ Tidewater Preserve SubDv. ⋅ 34208 Zip Code
Virtually Staged. Huge Price Reduction! Welcome home to this Coastal Carriage Home nestled within the 24-hour guard-gated community of Tidewater Preserve. This lovely two-story end-unit condo offers 2,332 square feet of thoughtfully designed living space, featuring concrete block construction, impact-resistant windows and doors, and a private elevator for effortless access. This bright and spacious residence includes 3 bedrooms, 2 full baths, a versatile den/office, abundant storage, and a 2-car garage. The open layout is perfect for both everyday living and entertaining, with natural light pouring in from multiple windows and the overside sliding glass doors. Enjoy calming breezes and breathtaking views of the Manatee River from your screened balcony. Boating enthusiasts will appreciate the community marina with boat slips available for lease (first-come, first-served), offering quick access to the Manatee River, Tampa Bay, the Gulf of America and the gorgeous white sand beaches on the gulf coast. Whether traveling by boat or car, this location is ideal for enjoying waterfront dining, shopping and easy access to University Town Center and downtown Bradenton. Tidewater Preserve delivers a true resort-style lifestyle with three pools (including a lap pool with beach entry), tennis courts, fitness center, dog park, playground, kayak launch, scenic riverfront walking trails, and two clubhouses available for private events. A full calendar of social activities enhances the vibrant waterfront community atmosphere. Experience luxury coastal living at its finest.

1246 Riverscape Street, Bradenton

578 - 580 Companion Way, Longboat Key
$900,000
4 Beds ⋅ 3 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value.. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.

578 - 580 Companion Way, Longboat Key

578 Companion Way, Longboat Key
$900,000
4 Beds ⋅ 3 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.

578 Companion Way, Longboat Key

2925 Terra Ceia Bay Boulevard Unit 2703, Palmetto
$599,000
3 Beds ⋅ 2 Baths ⋅ Bay Club Homes Condominium SubDv. ⋅ 34221 Zip Code
PRICE IMPROVEMENT! Experience Florida waterfront living in this beautifully maintained 2-bedroom PLUS DEN residence featuring PANORAMIC WATER VIEWS of Terra Ceia Bay, the Sunshine Skyway Bridge, and the St. Petersburg skyline. Furnishings may also be available under a separate personal property agreement, providing an opportunity for an easy transition to the Florida lifestyle. Designed for comfortable coastal living, this move-in-ready condominium offers an open-concept layout, desirable split-bedroom floor plan, soaring ceilings, and abundant natural light. Step outside onto the expansive PRIVATE BALCONY to enjoy morning coffee, bay breezes, and spectacular sunsets over the water. Inside, thoughtful finishes and a spacious layout create an inviting setting for both everyday living and entertaining. The versatile den offers additional space for a home office, media room, or guest accommodations. The primary suite features direct terrace access, while the open living and dining areas take full advantage of the impressive water views. Located within a GATED GOLF COURSE COMMUNITY, residents enjoy a RESORT-STYLE POOL, SPA, FIREPIT, scenic 500-foot FISHING PIER, and NATURE TRAIL through native Florida surroundings. Optional club membership provides access to additional amenities including an 18-hole executive golf course, tennis courts, fitness center, dining, and tiki bar. Golf opportunities are available without mandatory club membership. Enjoy convenient access to downtown Bradenton, historic Palmetto, area shopping and dining, Emerson Point Preserve, and the surrounding Gulf Coast. The nearby water ferry provides another way to experience the area's coastal destinations and beaches. With convenient access to Sarasota, St. Petersburg, Tampa, SRQ, and TPA, this residence is well suited for full-time or seasonal living. LIVE WHERE OTHERS VACATION! Wake up to expansive water views, enjoy memorable Florida sunsets, and lock and leave with ease. With its PRICE IMPROVEMENT and the opportunity to acquire furnishings separately, this is Florida WATERFRONT LIVING done right.

2925 Terra Ceia Bay Boulevard Unit 2703, Palmetto

529 77th Street, Holmes Beach
$4,995,000
5 Beds ⋅ 5 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
There's a different side of Anna Maria Island-one where island living, privacy, and life on the water all come together. Welcome to 529 77th Street in Holmes Beach-an extraordinary British West Indies inspired waterfront residence with more than 5,000 square feet, designed for gathering, entertaining, and enjoying life on the water.  Inside you will find two luxurious primary suites, beautiful custom millwork, an elevator, media room, and a chef's kitchen with an oversized island and butler's pantry-all surrounded by expansive living spaces and multiple terraces.  Outside is where the home truly shines.  Imagine mornings overlooking Bimini Bay, afternoons by the saltwater pool and spa, and evenings entertaining family and friends from your covered lanai and outdoor kitchen.  And when the water is calling, your boat is waiting right outside.  A 70 foot dock and a 13,000 pound boat lift put you just moments from the Intracoastal. This is more than a waterfront home.  It's a place to put down roots, make memories and experience Anna Maria Island as home. Call now to schedule your private showing of this amazing island property.

529 77th Street, Holmes Beach

4835 Gulf Of Mexico Drive Unit 106, Longboat Key
$675,000
2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code
Waterfront Living on Longboat Key – Direct Gulf Access Experience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact windows, sliding glass doors, and a hurricane front door—providing peace of mind and modern comfort. Enjoy seamless indoor-outdoor living with easy walk-out access, perfect for morning beach strolls, sunset views, or simply embracing the relaxed Gulf Coast lifestyle. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property offers exceptional value in a highly sought-after location. Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condominium holds many family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted. Unit is move-in ready to be enjoyed! Both bathrooms contain generous walk-in closets, with a washer/dryer installed in the guest closet. Come witness Resort Style amenities of two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan, first floor, master en-suite unit awaits your TLC. Kitchen includes side-by-side beverage refrigerators. R&R IS THE PACE, LBK IS THE PLACE!!!!!

4835 Gulf Of Mexico Drive Unit 106, Longboat Key

531 Sutton Place, Longboat Key
$529,000
2 Beds ⋅ 2 Baths ⋅ Sutton Place Condo SubDv. ⋅ 34228 Zip Code
Your easy island escape awaits in the beach-to-bay community of Sutton Place on Longboat Key. Spend your days at the deeded Gulf beach, lounging by one of two heated pools, kayaking on the bay, or heading out on the water—all within the community. This two-bedroom townhome is ideal for seasonal or year round living, offering impact windows and doors, steel roof trusses, and a private oversized garage for bikes, beach chairs, and island gear. The renovated kitchen features quartz countertops and Bosch appliances, and both bedrooms include walk-in closets and fully tiled baths. Unwind on two enclosed balconies overlooking a tranquil pond, then lock up and travel with confidence. Centrally located mid-island, Sutton Place offers the perfect blend of resort-style amenities in a beautiful setting.

531 Sutton Place, Longboat Key

610 Riviera Dunes Way Unit 406, Palmetto
$440,000
2 Beds ⋅ 2 Baths ⋅ Riviera Dunes Marina Condo SubDv. ⋅ 34221 Zip Code
SPECTACULAR WATERFRONT PARADISE with AMAZING VIEWS of RIVIERA DUNES MARINA & MANATEE RIVER COMPETIVELY PRICED TO SELL! This charming partially furnished two-bedroom, two-bath open layout with 9’ ceilings offers a total of 1,948 square feet with a spacious private balcony and den/office. The primary suite is a retreat overlooking the marina with views of the Manatee River that offers a generous walk-in closet, dual vanities and a luxurious soaking tub with separate shower. The kitchen features stainless steel appliances, granite countertops, and a charming eat-in nook. Additional highlights include a new roof (2025), 24-hour guard-gated entrance, indoor laundry room with extra storage, 9-foot floor-to-ceiling hurricane-impact sliders, and covered parking with ample guest parking. For boating, waterman, and fishing enthusiasts, this location is nothing short of extraordinary. Enjoy immediate access to Tampa Bay, the Intracoastal Waterway, Anna Maria Island and the shimmering Gulf via the Manatee River with the city of Bradenton on the south shore. Boat slips are often available for rent or purchase exclusively for owners, making this a marina-side paradise. Truly some of the best waterfront views and boat access values in the Tampa Bay area. Inside, the home blends charming coastal comfort with privacy. The community is pet-friendly, maintenance-free, and designed for resort-style living for primary and seasonal occupancy. Enjoy a temperature-controlled (heat and chill) waterside pool, hot tub, clubhouse, fitness center, covered pavilion with two gas grills, tennis and pickleball courts, and walking paths all set against the backdrop of the marina’s sparkling waters. When it’s time to unwind or entertain, stroll next door to the Dockside Grill for live music, or explore the vibrant events at the new Bradenton Area Convention Center and new Marriott Hotel Resort & Spa. You’re also minutes from the world-famous Anna Maria Island beaches, upscale shopping and dining at University Town Center, the Manatee Performing Arts Center, the new Herrig Center for the Arts, Riverwalk, Bradenton Museum and Planetarium, and Emerson Point Preserve. With effortless access to Interstate 75, Interstate 275, Sarasota, Tampa, St. Petersburg and three international airports, this location is as convenient as it is luxurious. This is the Florida lifestyle at its finest - refined, relaxed, and ready for you. This charming coastal residence just may be Florida Gulf Coast’s best kept secret and your new home.

610 Riviera Dunes Way Unit 406, Palmetto

206 Church Avenue, Bradenton Beach
$2,790,000
5 Beds ⋅ 6 Baths ⋅ Manatee Pond Subdivision SubDv. ⋅ 34217 Zip Code
LUXURY COASTAL RETREAT with 360° WATER VIEWS just steps from Bradenton Beach!!! Just two blocks from the sugar sand shores and perfectly centered between the beach and the bay, this spectacular three-story coastal retreat offers breathtaking 360° views of both the Gulf of Mexico and Sarasota Bay. Whether you are searching for a year-round residence, seasonal escape, or high performing investment property, this one-of-a-kind home truly has it all. With 5 bedrooms, 5.5 bathrooms, and multiple indoor and outdoor living spaces, the home is designed for both luxury and comfort. The first level welcomes you with a bright sitting area featuring sliding glass doors overlooking the HEATED pool and spa, along with a separate BONUS room perfect for a home gym, owner’s storage, or beach gear room. On the second floor, you’ll find four spacious bedrooms, each with its own ENSUITE bathroom and walk-in tiled shower, plus an open loft area currently set up with extra beds that can easily become a kids’ play area, game room, or lounge space. The third floor serves as the main living area, showcasing incredible full 360° water views, an open-concept kitchen with a large island and seating, granite countertops, stainless steel appliances, and peek-through windows flanking the stove, a separate dining area for formal or casual entertaining, and a living room surrounded by STUNNING water views. Also on this level is a PRIVATE bedroom suite with balcony access and another ensuite bathroom with dual sinks, and a walk-in tiled shower, PLUS a cozy sitting area leading to a balcony overlooking the pool and a spiral staircase to the ROOFTOP DECK creating your personal PARADISE for sunset watching and stargazing over the Gulf and bay. The outdoor living space offers a beautifully tiled heated pool and spa, a large covered lanai with wood plank ceilings, pavered flooring, a fully FENCED yard, and low-maintenance TURF grass for privacy. The pool features a NEW ELECTRIC HEATER and NEW POOL PUMP, the exterior has been freshly painted, and all appliances are lightly used and in excellent condition. Located just minutes from historic Bridge Street, this home is close to colorful shops, local restaurants, vibrant nightlife, live music, a fishing pier, mini golf, and more, with Bridge Street connecting the Sarasota Bay side to the Gulf of Mexico side of the island. This is the perfect place to unwind after a long day at the beach with endless activities nearby, and it truly doesn’t get better than this...LUXURY, LOCATION, LIFESTYLE, and VIEWS all in one unforgettable coastal property.

206 Church Avenue, Bradenton Beach

5608 Gulf Drive Unit 104, Holmes Beach
$785,000
2 Beds ⋅ 2 Baths ⋅ Sun Plaza West SubDv. ⋅ 34217 Zip Code
ITS TIME TO Wake up to the sound of waves and endless Gulf views in this beautifully situated two-bedroom, two-bath condo directly on the Gulf of Mexico. Step outside and onto the coveted, sugar-soft sandy beaches that make this area so sought after—perfect for morning walks, sunset strolls, and carefree beach days. Inside, the condo features a newly renovated kitchen that’s both stylish and functional, ideal for entertaining or preparing meals after a day at the beach. The thoughtfully designed layout offers comfortable living spaces and bedrooms with excellent privacy, plus the convenience of an in-unit laundry facility for effortless everyday living. Additional highlights include downstairs storage, perfect for beach chairs and gear, along with underground parking for added peace of mind. Located just minutes from shopping, restaurants, and local dining favorites, this condo perfectly balances relaxed beachfront living with easy access to all the best the area has to offer. Whether you’re seeking a full-time residence, a vacation escape, or an investment opportunity, this Gulf-front condo delivers the coastal lifestyle everyone dreams of. Come live your Anna Maria Life.

5608 Gulf Drive Unit 104, Holmes Beach

4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key
$649,900
3 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
THE BAY! THE GULF! THE BEST OF BOTH! Imagine a place where every day begins with the peaceful beauty of Longboat Key's sparkling bay and ends beneath the breathtaking colors of a Gulf Coast sunset. Perfectly positioned between both shores, this beautifully updated 3-bedroom, 2-bath end-unit villa offers the rare opportunity to experience the very best of island living from one exceptional location. Nestled within the highly sought-after waterfront community of Windward Bay, this 1,504-square-foot residence welcomes you with a sense of light, warmth, and effortless coastal elegance. As an end unit, the villa enjoys additional windows, enhanced privacy, and an abundance of natural sunlight throughout the day. Luxury vinyl plank flooring flows seamlessly through the living spaces, while custom plantation shutters add timeless character and refinement. The thoughtfully renovated kitchen blends style and functionality with granite countertops, beautiful soft-close cabinetry, and an inviting layout designed for everyday living and easy entertaining. The spacious great room opens effortlessly to a private outdoor patio, creating the perfect setting for morning coffee, afternoon relaxation, or dining beneath the coastal breeze. Life here is refreshingly simple. Ground-level living means no stairs, no elevators, and convenient parking just steps from your front door. Whether you're arriving home from the beach or carrying in groceries, everything about this villa is designed for easy, maintenance-free living. Equally impressive are the community improvements already in place. In 2020, the exterior was upgraded with hurricane-impact windows, hurricane-impact sliding glass doors, and a new roof, providing valuable peace of mind for years to come. Windward Bay has long been one of Longboat Key's most treasured communities, and it's easy to understand why. Set across 26 beautifully landscaped waterfront acres, residents enjoy three beach access points, a scenic half-mile nature trail, two heated swimming pools, fitness center, sauna, clubhouse, tennis and pickleball courts, kayak launches, covered parking, storage areas, and boat docks available by waitlist. Dolphins, manatees, tropical birds, and other native wildlife are frequent visitors, making every walk through the community feel like a nature retreat. Pet-friendly and financially strong, Windward Bay has completed both its Milestone Inspection and Capital Reserve Study. Monthly fees were reduced in 2025 and increased by only $13 for 2026, reflecting responsible community management and long-term stability. From this ideal location, you're just minutes from St. Armands Circle, Downtown Sarasota, Bridge Street, championship golf, waterfront dining, boutique shopping, and the exceptional arts and cultural attractions that make Florida's Gulf Coast so desirable. More than a beautiful villa, this is a lifestyle defined by sunshine, serenity, and connection to the water. A place where morning bay views, evening Gulf sunsets, and the ease of resort-style living become part of your everyday experience. THE BEST OF LONGBOAT KEY ISN'T ON THE BAY OR THE GULF... IT'S BETWEEN THEM. Welcome Home to Villa 8 at Windward Bay.

4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key

395 Aruba Circle Unit 303, Bradenton
$695,000
3 Beds ⋅ 3 Baths ⋅ Marina Walk On One Particular Harbour 2 SubDv. ⋅ 34209 Zip Code
Virtually Staged. PRICE IMRPOVEMENT and new, reduced condo fees! Welcome home to Harbour Isle, where refined coastal living meets effortless luxury. This rare end-unit condominium offers complete privacy, with no adjacent buildings and unobstructed, tranquil lake and Preserve views. Never rented and meticulously maintained by the original owner, this home is being sold partially furnished and feels like new while boasting over $40,000 in premium builder upgrades. The custom Oceana floorplan features dual primary suites with a split design, providing privacy for hosts and guests alike. The open layout offers ample space for entertaining or utilizing as a short- or long-term rental. The spacious kitchen features stainless steel appliances, solid wood cabinets, stone countertops, and thoughtful designer touches. Owner enhancements include upgraded LED lighting throughout and Smart features, including network cameras with no subscription required. Hurricane-rated triple sliding glass doors seamlessly open the living area to the lanai, creating the perfect space for entertaining family and friends in comfort, complete with new no-see-um tight specialized screening. Convenience and security are built in, with covered under-building parking, a private storage unit, and 24-hour virtual guarded gate. Designed for those who value exclusivity and ease, the private, resort-style community is anchored by the spectacular 23,000-square-foot Beach Club overlooking Anna Maria Sound. The waterfront Sky Bar, on-site dining, resort style pool and spa, private beach, and kayak launch create your own coastal retreat, steps from home. Residents enjoy four beautifully designed pools, state-of-the-art fitness center and sauna, fire pits, grilling areas, hammock park, lakeside swings, and miles of scenic walking and biking trails. Surrounded by nature, Harbour Isle sits steps from Neal Preserve and minutes from Robinson Preserve for kayaking, trails, and birdwatching. Just beyond the gates, enjoy the Margaritaville-inspired Compass Hotel, Floridays Tiki Restaurant, Compass Bar & Chill, and marina access at Pier 77, offering wet and dry storage, Gulf access, and Freedom Boat Club. Located 1-2 miles from the pristine beaches, local shops, and dining of Anna Maria Island, Harbour Isle offers a rare blend of privacy, convenience, and resort-level amenities. This is more than a home, it is a lifestyle investment in exclusive coastal living, ideal for full-time residents, seasonal owners, or investors seeking income-producing potential. Schedule your private tour today.

395 Aruba Circle Unit 303, Bradenton

4420 Exeter Drive Unit 303, Longboat Key
$499,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Seller to install a new stackable washer/dryer prior to closing. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.

4420 Exeter Drive Unit 303, Longboat Key

506 58th Street, Holmes Beach
$3,300,000
4 Beds ⋅ 6 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
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. Complementing the home's HURRICANE-IMPACT WINDOWS, professionally INSTALLED FLOOD PANELS provide an additional safeguard, reflecting the thoughtful attention to both luxury and long-term resilience found throughout the property. 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.

506 58th Street, Holmes Beach

6006 Gulf Drive Unit 214, Holmes Beach
$749,900
2 Beds ⋅ 2 Baths ⋅ Playa Encantada Condominium SubDv. ⋅ 34217 Zip Code
Set within the beachfront enclave of Playa Encantada, this beautifully maintained two-bedroom, two-bath residence offers an effortless coastal lifestyle just steps from the sand and the island trolley — placing the area's finest shops, restaurants, and attractions within easy reach. Inside, an open and light-filled layout creates an inviting sense of space. The kitchen is appointed with granite countertops, stainless steel appliances, and generous cabinetry, while the living and dining areas flow seamlessly onto a private balcony overlooking the heated pool — an ideal setting to take in the Gulf breezes and glimpses of the water beyond. Both bedrooms are generously sized, with the primary suite featuring a private en-suite bath. Residents enjoy a thoughtful collection of resort-style amenities, including a heated pool, tennis courts, shuffleboard, and private beach access. A flexible two-week minimum rental policy further enhances its appeal, offering an exceptional opportunity as a seasonal retreat or income-producing investment.

6006 Gulf Drive Unit 214, Holmes Beach

6811 Georgia Avenue, Bradenton
$849,900
4 Beds ⋅ 3 Baths ⋅ Bayshore Gardens SubDv. ⋅ 34207 Zip Code
INCREDIBLE, NEW PRICE!!! This tropical adventure home is the one you've been waiting for, where everyday living is a waterfront vacation!! This fully updated 2,400 sq ft, 4 bedroom/3 full bath home, is nestled on a deep, sailboat water canal with direct access to Sarasota Bay and the Gulf of America (no bridges) - a boater’s paradise with wide, unobstructed access to sandbars, deep-water fishing, water sports, waterfront restaurants, beaches and more - all within minutes!! Enjoy 70 FEET of water frontage on this canal (with extra-wide width)! In 2020, a NEW DOCK, NEW 16,000 lb. BOAT LIFT!! NEW SEAWALL (2015), and a fish cleaning station was completed!! You'll experience peace of mind here with a NEW ROOF!! NEW A/C (1 unit), 2-A/Cs. for zoned efficiency, impact-resistant windows, 2-Newer hot water heaters, newer appliances throughout! There is WHOLE-HOME GAS ENERGY for huge savings (also has full electric for flexible options). This home was never affected by Hurricanes nor storm surges! Entering the home, you'll be greeted with with an OPEN FLOOR PLAN, NEW TILE THROUGHOUT, NEW large, CUSTOM KITCHEN with REAL WOOD CABINETS and generous, STONE COUNTERTOPS and bar seating! The dining/flex space is currently enjoyed as a game room with a pool table perfectly situated for family and friends to have fun. There are TWO generously-sized PRIMARY bedrooms (en suites) with updated bathrooms offering many flexible options for guests or mother-in-law suite possibilities. There is a spacious, indoor laundry room. Don't miss all the hall closets that were smartly added during 2003 renovations. Step into the heartbeat of this exceptional home - the EXPANSIVE, UNDER ROOF/SCREENED LANAI! This sanctuary offers year-round enjoyment of endless sunsets overlooking the canal and is embraced by the tropical retreat of the upgraded grounds and rich, tropical landscaping. Whether your entertaining large gatherings with Al fresco dining or taking a rest after boating/fishing with family, this large space is set-up for it all with brand new tile flooring, large outdoor kitchen/bar, gas stove cooking (perfect for your fish), refrigerator, deep freezers (perfect for your fresh catch of grouper), and a commercial ice maker! There is ample space for a future pool. Bring your RV - there is dedicated parking on the side of home with vinyl gate/fencing. You'll appreciate additional parking spaces which includes a carport, extended and circular driveway. The yards have well-irrigation throughout (more savings). There are NO HOA/NO DEED RESTRICTIONS - (NO FEES), but residents of Bayshore Gardens enjoy an amenity-rich community with an Olympic-sized pool (only $10/year key fob access), pickleball, tennis, basketball courts, playgrounds, a wood shop, private marina, and boat launch. This home is located in a coveted location with convenient access to award-winning beaches, Anna Maria Island, Siesta Key, SRQ Airport, IMG Academy, Downtown Sarasota dining and shopping. Homes like this at this price point, with direct Gulf access and waterfront/canal living, do not last long, so schedule your private showing today and let your ultimate, Florida waterfront lifestyle begin! Be it a full-time home, vacation retreat, or an income-producing rental (short term rental IS allowed), you'll quickly see the unrivaled value this home has to provides for waterfront living in Bradenton/Sarasota! Pool table, 2 deep freezers, commercial ice maker, remain! Furnishings are negotiable!

6811 Georgia Avenue, Bradenton

6489 Gulfside Road, Longboat Key
$13,995,000
4 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Ready to live directly on the Gulf? This Seaward Homes Curated Collection residence at 6489 Gulfside is move-in ready, with direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects and staged by Clive Daniel Homes, the home pairs cutting-edge, hurricane enhanced construction with exceptional quality and attention to detail throughout. Set on a coveted 90' Gulf/beach-front lot, the property offers soft sand, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a major beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the island. Gulfside Road is also one of the rare Gulf-side streets set back from the main highway, so the setting feels private and quiet, worlds away from the activity of Gulf of Mexico Drive, just minutes from Whitney Plaza and North Longboat Village, and moments from fine dining at Shore and Mar Vista. The main house is elevated over 15', with 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 square feet of air-conditioned living space, including a grade-level, air-conditioned multipurpose room ready for a home gym, a wellness studio, or whatever fits your lifestyle. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces, one on the main floor and one on the second, are ideal for enjoying the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes take the home to the next level, with large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, premium Longboard™ aluminum architectural details, and a fine light-sand stucco exterior. A resort-like pool and spa are surrounded by lush tropical landscaping, and the four-car garage leaves room to add car lifts. Longboat Key is an 11-mile barrier island just minutes from St. Armands Circle and downtown Sarasota, with Sarasota Bradenton International Airport about 25 minutes away. This is a rare chance to own this level of coastal luxury directly on the Gulf, don't wait!

6489 Gulfside Road, Longboat Key

5231 Gulf Of Mexico Drive Unit 104, Longboat Key
$499,000
1 Beds ⋅ 1 Baths ⋅ Covert Condominium SubDv. ⋅ 34228 Zip Code
Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

5231 Gulf Of Mexico Drive Unit 104, Longboat Key

50 N Shore Drive, Anna Maria
$4,490,000
4 Beds ⋅ 5 Baths ⋅ Bimini Bay Estates SubDv. ⋅ 34216 Zip Code
An exceptional opportunity to experience true island living where waterfront boating and beach access come together—just minutes apart—on Anna Maria Island. This beautifully designed 4-bedroom, 4.5-bath turnkey furnished coastal residence offers a rare blend of luxury, comfort, and lifestyle, ideally situated on a tranquil canal while remaining only moments from the island’s world-famous white-sand beaches. Homes offering private boating access this close to the beach are increasingly difficult to find on Anna Maria Island. From this property, enjoy the freedom of launching your boat from your own backyard, paddleboarding at sunrise, or cruising to open water—then return home and head to the beach cart in minutes. It is this seamless balance of water, sand, and island convenience that truly sets this home apart. Built in 2020 and thoughtfully designed for modern coastal living, the home features a bright, open floor plan filled with natural light and enhanced by coastal-inspired finishes and refined details throughout. The gourmet kitchen serves as the heart of the home, equipped with top-of-the-line stainless steel appliances, quartz countertops, a wine refrigerator, and generous prep and storage space—perfect for entertaining after a day on the water or hosting family and friends. Each of the four bedrooms includes a private en-suite bath, offering comfort and privacy for owners and guests alike. An elevator provides easy access to all levels, adding convenience for everyday living. Outdoor living is where this home truly shines. The private backyard retreat features a heated pool and spa with sun exposure, an expansive pool deck, lush tropical landscaping, and multiple outdoor living and dining areas designed for relaxing, entertaining, and enjoying the island breeze. Whether you’re gathering for sunset cocktails, enjoying a quiet evening under the stars, or unwinding after a beach day, this space feels like a personal resort. For boating enthusiasts, the property offers a private 16’ dock and an oversized boat slip measuring approximately 12’ x 35’, providing direct access to Tampa Bay and the Gulf. This setup is ideal for daily cruising, fishing excursions, paddleboarding, or simply enjoying the peaceful waterfront setting. Situated on an unusually large lot for Anna Maria Island with over 12,000 sq ft , the home also provides ample parking, a spacious driveway, garage, and dedicated golf cart storage—features that add meaningful convenience for both owners and guests in this sought-after location. Located in the heart of Anna Maria Island, this property places you just minutes from pristine beaches, Pine Avenue’s charming boutiques and dining, Bean Point’s legendary sunsets, local art galleries, and the island’s laid-back, walkable, golf-cart-friendly lifestyle. Known for its relaxed pace, vibrant community, and old-Florida charm, Anna Maria Island continues to be one of Florida’s most beloved coastal destinations. Whether you are searching for a full-time residence, a luxury second home, or a proven income-producing vacation rental with forward bookings already in place, this exceptional property offers unmatched versatility and long-term value. Combining waterfront access, beach proximity, turnkey luxury, and an unbeatable island location, this home represents a rare chance to own one of Anna Maria Island’s most desirable lifestyle properties.

50 N Shore Drive, Anna Maria

2206 Avenue A, Bradenton Beach
$3,495,000
7 Beds ⋅ 8 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code
2206 Avenue A, Bradenton Beach, FL 34217 Luxury Investment Meets Coastal Perfection A premier 7-bedroom, 7.5-bath luxury retreat just a 5-minute walk from Bradenton Beach. This 2022-built coastal haven combines elegant design, proven rental performance, and exceptional guest appeal—making it an ideal rental investment on coveted Anna Maria Island. Designed for large groups and multi-family stays, this property offers an unbeatable combination of scale, amenities, and location—features that drive consistent high occupancy and premium nightly rates. Investment Highlights: Prime location — 5-minute walk to Bradenton Beach and close to Pine Avenue shops & dining High-income layout — 7 bedrooms / 7.5 bathrooms (sleeps large groups comfortably) Premium amenities — rooftop deck with panoramic Gulf & Bay views, private heated pool & spa, BBQ area, and outdoor lounge Turnkey luxury — sold fully furnished and professionally designed with coastal chic interiors Proven rental appeal — ideal for reunions, retreats, and vacation groups seeking a luxury experience Strong ROI potential — similar homes on Anna Maria Island generate six-figure annual rental revenue Inside, guests are greeted by an airy open-concept living space filled with natural light, a fully equipped chef’s kitchen with quartz counters and stainless appliances, and seamless indoor–outdoor flow through sliding glass doors. Every bedroom includes a private ensuite, ensuring comfort and privacy for guests. From sunrise coffee on the balcony to sunset cocktails on the rooftop deck, Beachly Beloved offers an unforgettable guest experience—one that translates to repeat bookings and sustained income for savvy investors. Your opportunity: A rare, income-producing coastal asset in one of Florida’s strongest luxury rental markets.

2206 Avenue A, Bradenton Beach

2175 Avenue A, Bradenton Beach
$8,400,000
10 Beds ⋅ 12 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code
Welcome to 2175 Avenue A, Bradenton Beach, Florida A Luxury Island Estate Designed for Generational Memories & Investment Returns Step into the pinnacle of coastal elegance with this magnificent 10-bedroom, 12-bath luxury estate, nestled just steps from Bradenton Beach on coveted Anna Maria Island. Built in 2022, this turnkey coastal compound offers the perfect blend of refined relaxation and high-end amenities, making it ideal for luxury vacation rentals, multi-family getaways, or premium short-term rental investment. With sleeping space for 23 guests, new designer furnishings, and resort-style features, this stunning property checks every box for the discerning investor seeking both lifestyle and ROI. An established rental estate with a return clientele and a healthy ROI for any seasoned investor, this is a proven performer in one of Florida’s most desirable coastal markets. Investor Highlights: 3-minute walk to Bradenton Beach – Prime proximity to one of Florida’s most beloved beaches 10 spacious bedrooms | 12 modern bathrooms Sleeps up to 23 guests – Ideal for large family reunions or group rentals 8 king suites, 2 twin beds, and a full/full bunk – All with ensuite bathrooms Heated private pool & spa + outdoor bar, grill, and patio dining Rooftop deck with panoramic Gulf & Bay views – Ideal for sunsets and evening gatherings Game-ready backyard with putting green, ping pong, and foosball Steps to Bridge Street, dining, shopping, and marina – all walkable or bikeable Property Features: Every detail in this estate has been thoughtfully curated for upscale beach living: Bright, multi-level layout with expansive balconies and water views Open-concept great room, oversized TV, and seating for groups Gourmet kitchen with quartz island, premium appliances, and plenty of space for entertaining 11 spa-inspired bathrooms with sleek finishes, walk-in showers, and designer details Private suites throughout ensure comfort and privacy for every guest Outdoor Living at Its Finest: The tropical backyard is a private oasis: Heated pool with spillover spa Outdoor dining, grill, and lounge area Custom putting green and games for all ages Rooftop deck with 360° views of Gulf waters and the island skyline Why Investors Love 2175 Avenue A: High rental income potential in a top-tier vacation rental market Established rental estate with proven performance and return clientele New construction = minimal maintenance Ideal for 1031 exchange buyers, portfolio diversification, or luxury Airbnb investor Located in one of Florida’s strongest coastal markets, with year-round demand Zoned and designed for maximum occupancy and revenue optimization 2175 Avenue A isn't just a home—it's a rare investment opportunity on Anna Maria Island, combining luxurious design, unbeatable location, and outstanding rental appeal. Whether you're looking to expand your luxury rental portfolio, secure a premium vacation home with income potential, or enter Florida’s elite coastal market, this estate delivers on all fronts.

2175 Avenue A, Bradenton Beach

801 N Shore Drive, Anna Maria
$8,250,000
4 Beds ⋅ 4 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
Rising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless Gulf-front residence that blends enduring craftsmanship with inspired artistry. The main living level unfolds into a grand living and dining area, where a full wall of sliders frame endless Gulf views and spectacular sunsets. The expansive balcony is an entertainer’s dream, featuring a fully equipped Lynx outdoor kitchen and a beautifully carved fireplace—an inviting setting for al fresco dining or evenings by the fire. Inside, the chef’s kitchen is outfitted with Sub-Zero, Viking, and Miele appliances, seamlessly combining performance and elegance. A refined library retreat, complete with a fireplace and exquisitely carved bookcases, offers a quiet haven for reading or reflection. The third floor is devoted to luxurious private living. The palatial primary ensuite is a serene sanctuary with spa-like amenities and opens to its own Gulf-facing balcony. Here, a soaking tub, rain shower, and an additional fireplace create an indulgent, resort-style experience. Also on this level are a gracious guest suite, a whimsical children’s ensuite bedroom, and a conveniently located laundry room. The first floor welcomes you with a dramatic foyer featuring soaring ceilings and an elevator. Just beyond lies the imaginative Captain’s Quarters, a fantastical space designed to replicate the galley of a pirate’s lair—both playful and unforgettable. An expansive office follows, showcasing granite countertops and intricately carved walls with integrated drawers and shelving, offering both beauty and function. Outdoors, the home transforms into a private oasis. The grotto-style pool provides shaded comfort and is adorned with multiple water features, while a surrounding fireplace and dining area create an intimate setting for gathering. Beyond the pool, a sun-drenched private patio invites leisurely afternoons of relaxation and sunbathing. Built to stand the test of time, The Golden Dolphin is constructed with concrete and rebar throughout and engineered with advanced drainage systems designed to reroute floodwaters. This exceptional residence has sustained no damage from past hurricanes, offering peace of mind alongside its unparalleled beauty. A rare offering on Anna Maria Island, The Golden Dolphin is a masterful expression of luxury, resilience, and coastal elegance—where art, architecture, and the Gulf converge in perfect harmony.

801 N Shore Drive, Anna Maria

5612 Guava Street, Holmes Beach
$3,495,000
4 Beds ⋅ 6 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code
Striking modern luxury meets investment potential at The Black Pearl, a four-bedroom, five-and-a-half-bath residence located just a short walk from the beaches of Holmes Beach, downtown shopping and dining, and the island trolley. This architecturally distinctive black-and-white home features a private black-bottom infinity-edge pool, resort-style outdoor living, and a rooftop deck with panoramic Gulf views. Designed for both lifestyle and performance, the home offers a bright open-concept interior, gourmet kitchen with island seating, and four king bedroom suites—each with a private ensuite bath—plus a bonus den with additional sleeping flexibility. Outdoor amenities include a full outdoor kitchen, multiple lounge and dining areas, outdoor shower, and ample on-site parking. Currently part of the Exclusive Vacations luxury rental program, the property offers immediate access to a professionally managed, high-end short-term rental platform focused on premium positioning, elevated guest experience, and revenue optimization. A rare opportunity to own a visually iconic, walkable luxury home with proven short-term rental appeal on Anna Maria Island.

5612 Guava Street, Holmes Beach

2201 Avenue C, Bradenton Beach
$3,100,000
6 Beds ⋅ 6 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code
Gorgeous, turnkey, multi-generational, six bedroom coastal retreat just steps from the beach in the heart of Bradenton Beach on Anna Maria Island. Designed for relaxed island living and memorable gatherings, this beautifully furnished 3,103-square-foot home combines generous accommodations, resort-style outdoor living and panoramic water views. The home's reverse-floor-plan design places the main living area on the upper level, creating an inviting open-concept space for living, dining and entertaining while capturing beautiful beach and Gulf views. Step onto the beachside deck or continue up the spiral staircase to the rooftop sundeck, where panoramic views extend across the beach and bay, an exceptional setting for morning coffee, afternoon sunsets and evening cocktails. The home offers six bedrooms, four full bathrooms and two half bathrooms, providing exceptional flexibility for families, extended stays and large groups. The primary suite features beach views and a spacious ensuite bath, while additional bedrooms provide comfortable accommodations for guests. Outside, the private fenced yard creates a true resort-like retreat. A private pool and spa are surrounded by lush tropical landscaping, with a covered dining area, outdoor bar and grilling area designed for long afternoons and evenings together. A garage provides valuable space for beach equipment, storage and games. Tastefully furnished and offered turnkey, 2201 Avenue C is ideally suited for a buyer seeking a private Anna Maria Island residence, a second home or a property with established vacation-rental appeal. The property has also been marketed as a vacation rental, and its 6 bedroom configuration, pool, rooftop deck, beach proximity and large-group accommodations create a compelling combination of lifestyle and investment potential. Located just steps from the Gulf and close to the restaurants, shops, waterfront experiences and laid-back atmosphere that make Anna Maria Island so desirable, 2201 Avenue C isn't simply a place to own...it is a place to live the island lifestyle!

2201 Avenue C, Bradenton Beach

5270 Gulf Of Mexico Drive Unit 508, Longboat Key
$754,900
3 Beds ⋅ 3 Baths ⋅ The Banyan Bay Club SubDv. ⋅ 34228 Zip Code
Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence with a NEW AC (Aug 2026) truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

5270 Gulf Of Mexico Drive Unit 508, Longboat Key

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