Remarks: This beautifully updated 2BD/2BA coastal retreat offers the perfect blend of comfort, style, and location in the highly desirable Cayman Cay community on Holmes Beach. Ideally situated mid-island and just steps to the soft powdery sands of the Gulf, this TOP FLOOR residence is TURNKEY FURNISHED and truly MOVE-IN-READY. Inside, you’ll find a bright, open layout with a relaxed beach-inspired feel and thoughtful upgrades throughout. A MAJOR RENOVATION opened up the kitchen and main living area, creating a more spacious and modern flow with NO CARPET throughout the unit. The well-appointed kitchen features upgraded cabinetry, modern countertops, tile backsplash and stainless steel appliances, making it perfect for both everyday living and entertaining. The main living space features custom wood accent wall detailing, adding a stylish coastal touch, and providing both durability and easy maintenance. Both bathrooms have been tastefully updated, and recent improvements include a NEW HURRICANE IMPACT-RATED Turtle Glass sliding door and a REFRESHED LANAI. Step out onto the screened lanai and enjoy peaceful surroundings with PARTIAL GULF VIEWS along with views of the pool and tropical landscaping, creating the perfect space to relax and unwind. Additional features include a private owner’s storage room and a designated covered carport space for Unit #207. Cayman Cay offers a well-maintained community setting with a heated pool, shuffleboard courts, and BBQ grilling area, perfect for relaxing after a day at the beach or enjoying time with family and friends. The location is truly unbeatable, just minutes from local restaurants, shopping, Publix, CVS, and everything that makes Anna Maria Island so special. For added convenience, the island trolley is nearby, making it effortless to explore the surrounding area. Enjoy convenient access on and off the island, along with a short drive to Sarasota Bradenton International Airport. Whether you're seeking a full-time residence, a relaxing vacation retreat, or an investment property, this condo delivers the perfect blend of location, modern updates, and easy island living. UNPACK, UNWIND, and START LIVING the island life from day one—while offering excellent INCOME POTENTIAL when you’re away.

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Michelle Wasson (941-726-5166)

Remarks: Welcome to an inviting ground-level canal-front condo tucked into the highly sought-after WestBay Point and Moorings community on beautiful Anna Maria Island. This bright and airy 2-bedroom, 2-bath residence welcomes you with a private front courtyard—an ideal spot for morning coffee or a quiet read—then leads into a versatile enclosed lanai offering endless possibilities for a home office, sunroom, or additional entertaining space. Inside, the updated kitchen features KraftMaid cabinets, and new countertops, convenient pull-out drawers and a wet bar that make hosting effortless. The expansive dining and living room combination brings in natural light from multiple sliders and flows seamlessly to the enclosed back lanai, where peaceful canal views and glimpses of the community tennis courts set a serene backdrop. The primary suite is a tranquil retreat with lanai access, an updated ensuite bathroom and generous walk-in closet with abundant storage. The beautifully updated second bath serves the guest bedroom, which also enjoys direct access to the front lanai, plus its own walk-in closet. This ground-floor unit is especially attractive for its accessibility and, importantly, it did not flood. Beyond the home, WestBay Point and Moorings deliver resort-style amenities: a heated community pool and spa, well-maintained tennis courts, and a kayak launch for easy access to the canal and surrounding waterways. Nestled in the heart of Holmes Beach, the community offers a rare combination of convenience and privacy—close to shops, dining and the island’s renowned beaches, yet tucked away for peaceful, everyday living. This thoughtfully updated condo is a must-see for anyone seeking island living with comfort, storage and outdoor lifestyle conveniences. Short walk to restaurants, shops, and Island trolly stop.

Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)

Listing Agent: Martha Robel (941-773-4594)

Remarks: First-floor corner unit with amazing bay views in the waterfront community of Westbay Cove on Anna Maria Island. This 2 bedroom, 2 bathroom condo offers a bright, functional layout with abundant natural light and peaceful views of the bay. The kitchen features custom cabinetry, tile backsplash, and newer appliances, and opens to the main living area and enclosed Florida room. The Florida room adds additional living space and is the perfect place to enjoy morning coffee while taking in the bay breezes and sunrise skies. The primary suite includes a walk-in closet, private sliding-door access to the Florida room, and an updated en suite bath with a quartz vanity and tile flooring. The guest bedroom is generously sized with dual closets and an ensuite bathroom featuring quartz countertops and a custom tiled shower. The guest bedroom also has private access to the screened front lanai. Additional features include hurricane-rated windows (sliders are not hurricane-rated), updated flooring, and a new stackable washer and dryer in the screened front lanai. The unit is being sold turnkey furnished, making it move-in ready for seasonal use, full-time living, or investment. Westbay Cove is a well-maintained bayfront community on Anna Maria Island offering two pools and beautifully landscaped waterfront grounds. Located just minutes from Anna Maria Island beaches, restaurants, and shopping.

Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)

Listing Agent: April Green (941-773-1680)

Remarks: Under contract-accepting backup offers. Turnkey, income-producing boutique beach condo just steps to the sand. Fully furnished and rental ready, this unit has an established revenue history compliant with Holmes Beach's 7-day minimum rental policy, making it the perfect blend of personal use and strong short-term rental potential. Completely renovated with updated electrical, plumbing, modern finishes, and impact-resistant windows, doors, and sliders. The building also remained completely dry during recent storms- an increasingly important factor on the island. Unbeatable location with a 1-minute stroll to the beach, grocery, restaurants, and the town center. Community features include a heated pool with new outdoor furniture, additional storage for bikes and beach chairs, plus pet friendly flexibility. Assigned covered parking, a large private storage closet, and an association benefit that is all inclusive of your utilities, insurance, reserve fund, and building maintenance add even more convenience and value, making this the true path to living on island time.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Justin Vitalo (904-347-8102)

Remarks: *All new stainless-steel appliances have been since installed* Welcome to Island living at its finest! This fully furnished beautiful 2-bed, 2-bath second-floor condo at Westbay Point & Moorings offers a rare combination of stunning water views and peace of mind. Perched on the highest point of Anna Maria Island, this home has been protected from any past flooding - a unique advantage that sets it apart. Step inside and you’ll find tasteful updates throughout, complemented by a new roof, AC unit, and hurricane grade windows for worry-free ownership. The light-filled living spaces flow seamlessly to a breathtaking view where you’ll enjoy morning coffee, watch dolphins play, and take in vibrant sunrises over the bay. Life here is about more than a home - it’s about the Florida dream lifestyle. Launch your vessel from the community dock, lounge at the heated pool, or stroll and bike to local shops, restaurants, and Anna Maria’s world-famous beaches. Whether you’re seeking a personal retreat or a smart investment property, this condo delivers. With flexible rental opportunities in one of Florida’s most desirable beach destinations, you can enjoy the island lifestyle while benefiting from strong vacation rental demand. Don’t miss your chance to own a piece of paradise on Anna Maria Island!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Justin Vitalo (904-347-8102)

Remarks: One or more photo(s) has been virtually staged. NEW ROOF! Welcome to this freshly remodeled, elevated 2-bedroom, 2-bathroom end-unit condo with a flex room at Island Village in Holmes Beach. Perfectly located just one block from the pristine sands of Anna Maria Island. This bright and airy condo has been thoughtfully updated, featuring a clean, modern aesthetic. It includes two dedicated parking spaces under building and includes a storage room. The interior has been freshly painted and new tile floors installed in the kitchen and flex room. One of the standout upgrades is the enclosed flex room, now fully under air with the recent extension of the A/C system. This versatile bonus room serves as a wonderful flex space, featuring a large closet and offering endless possibilities for use. Use it as a bright and inviting sunroom filled with natural light, a comfortable home office that inspires productivity, or a cozy retreat that effortlessly adapts to your lifestyle needs. This sun-filled retreat is enhanced with sliding glass doors and Phifer weave sunscreen shades, offering views of the lush, park-like surroundings. The kitchen is designed with both style and functionality in mind, featuring durable Corian countertops, a breakfast bar, a Whirlpool full-size stainless-steel refrigerator and freezer, and custom Kitchen Craftmade Cabinetry. The primary bedroom includes sliding glass doors that open to the air-conditioned flex room, a large walk-in closet, and an en-suite bathroom with a walk-in shower. The second bedroom offers another ensuite bath, making it ideal for guests or family members. A dedicated laundry room with a full-size washer and dryer adds everyday convenience. Recent updates include a NEW ROOF in 2025, an upgraded electric meter in 2024, and refreshed exterior paint completed in 2021. The condo also includes an osmosis water filtration system. This condo is part of Island Village, a well-maintained, maintenance-free community where the HOA covers cable TV, internet, water, sewer, trash, insurance, and upkeep of the grounds, exterior, community pools, and tennis courts. Residents enjoy access to two heated pools and two tennis/pickleball courts, offering ample recreational opportunities year-round, and owners are permitted to rent their condo up to three times yearly, with a minimum rental period of one month. Located only two blocks to direct beach access, this condo is ideally positioned within easy access to over 20 public beach access points, 12 parks, popular restaurants, and local shops. Don’t miss this rare opportunity to own a beautifully updated condo in one of Anna Maria Island’s most desirable communities. Schedule your tour today and experience the relaxed, tropical lifestyle of Island Village. Be sure and check out the 3D walkthrough and floor plan for this lovely condo in Island Village.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)

Listing Agent: Hannah Hillyard (941-744-7358)

Remarks: Under contract-accepting backup offers. In the sought-after Westbay Point and Moorings community, this 1,377-square-foot second-floor End unit residence offers an exceptional opportunity to complete a coastal retreat with your custom finishes. This two-bedroom, two-bath condominium is in vanilla shell/box condition, with new sheetrock installed, and major structural and mechanical upgrades completed. Features include a new roof with a tie-down system, new firewall, new air duct system, updated insulation, new electric and plumbing infrastructure, new air handler and new roof-mounted air compressor. All windows have been replaced with hurricane impact-rated glass, including those in the guest bedroom and side elevations. Additional upgrades include a new hurricane-rated front entry door, porch screening system, and laundry room door. Enjoy panoramic water views and an unobstructed view of the Skyway Bridge from this top-floor unit. The residence presents an ideal blank canvas for designing a personalized interior while benefiting from high-cost improvements.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: David Liberatore Pllc (941-900-9995)

Remarks: Under contract-accepting backup offers. There is so much value in the elevation of this property as it got no water in the hurricane and these three buildings are more elevated than most of the entire island. RENOVATED AND TURNKEY. Prepare to be enthralled by the mesmerizing beauty of the sparkling waters of Anna Maria Sound, teaming with playful dolphins, graceful manatees, and the colorful spectacle of Florida's native birds. Witness spectacular sunrises as you wake up to the beautiful rays filling your space every morning. Then there is the magnificent moon while casting its illuminating reflection upon Anna Maria Sound, all from this incredible place. This building sits on one of the highest points on the island and did not flood during previous storms. This makes it an Excellent investment. Sit on the Lanai and watch the yachts as they await the Manatee Bridge to lift so they can go under. This beautifully remodeled condo on the water is one of the few dog friendly communities. If all this wasn't enough the space you walk into is being sold Turnkey and looks as if a professional designer made all the decisions down to the smallest things. Now its all your ready to go just pack a suitcase and no need to do anything. Are you a bird watcher? If so you will love the birds you view all day as they fly close to you coming to and fro from nearby Robinson Preserve. One of the nicest things about this place is you don't get stuck during season in all the traffic on the island and its easy to get off to the main land without the long wait that the owners on the north end or south end have. Community has a kayak launch and pickleball as well as tennis and a large heated pool with views of the water. Community HOA fees are much lower than most due to the lack of damage as compared to other places on the island.

Listing is courtesy of: COASTAL KEY REALTY LLC (941-993-9380)

Listing Agent: Amy Jones (941-993-9380)