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$5,495,000
4 Beds ⋅ 5 Baths ⋅ 226026963 MLS
An exceptional opportunity to own a beautifully crafted residence in one of Naples' most coveted waterfront neighborhoods, Five Hundred Fifty Twenty-First Avenue South captures the essence of effortless luxury in the heart of Aqualane Shores. Ideally positioned adjacent to Port Royal and just moments from the Gulf's pristine beaches, Third Street South, and Fifth Avenue South, this remarkable home offers an unrivaled blend of elegance, comfort, and location. Encompassing approximately Four Thousand square feet of thoughtfully designed single-level living, the residence is filled with natural light and showcases soaring ceilings, solid Eight-foot core doors, and exquisite custom millwork that reflect impeccable craftsmanship throughout. Designed for both intimate living and sophisticated entertaining, the open floor plan flows seamlessly between gracious interior spaces and spectacular outdoor living. The contemporary primary suite is a private sanctuary featuring multiple walk-in closets and a spa-inspired bath with dual vanities, a soaking tub, and a separate walk-in shower. Two additional ensuite guest bedrooms, a versatile fourth bedroom currently serving as a den, and an elegant powder bath provide exceptional comfort and flexibility for family and guests alike. Beyond the interiors, a true resort-inspired retreat awaits. The expansive marble-tiled lanai surrounds a heated pool with a cascading waterfall spa, while the fully equipped outdoor kitchen creates the perfect backdrop for elegant alfresco dining and unforgettable evenings under the stars. Lush, professionally designed landscaping provides exceptional privacy and a serene tropical setting. Whether enjoying a morning walk along the sugar-white sands of the Gulf, dining at Naples' finest restaurants, or browsing the boutiques and galleries of nearby Third Street South and Fifth Avenue South, this extraordinary residence offers the quintessential Naples lifestyle. Beautifully finished and offered move-in ready, this is luxury living at its finest.

550 21ST Avenue S, Naples
$10,995,000
5 Beds ⋅ 7 Baths ⋅ 226011666 MLS
Perfectly positioned on over half an acre in the prestigious community of Aqualane Shores, this extraordinary estate embodies the essence of refined coastal luxury. This timelessly updated residence offers an unparalleled blend of sophistication, privacy, and effortless Naples living just four homes from Naples beach. Masterfully designed by the renowned Stofft Cooney Architects, the home is a showcase of exceptional craftsmanship and thoughtful design. From the moment you enter the grand foyer, you are welcomed by rich architectural details including high ceilings, and expansive living spaces designed to capture natural light and tranquil lake views throughout. Spanning five en-suite bedrooms plus a study, the residence offers an ideal balance of elegant entertaining and relaxed everyday comfort. The chef’s kitchen serves as the heart of the home, seamlessly connecting to a spacious family and club room, while a formal dining area create a timeless setting for gatherings both intimate and grand. The luxurious first-floor primary suite provides a serene retreat with a spa-inspired bath including an outdoor shower, while an additional guest suite on the main level ensures comfort and privacy for visitors. The home’s south-facing outdoor living experience is perfection. Designed for privacy, the expansive lanai features a fireplace, summer kitchen, and multiple lounging areas overlooking a tropical pool and spa with cascading waterfall features. Surrounded by lush landscaping and peaceful lakefront vistas, the setting feels like a private island sanctuary in the heart of Naples. Upstairs, three beautifully appointed guest suites each offer ensuite baths, while a stunning rooftop terrace provides the perfect vantage point to enjoy sunsets, Gulf breezes, and the serene beauty of the surrounding landscape. Located just one block from the beach and moments from the boutiques, fine dining, and vibrant charm of Third Street South, this remarkable residence captures the very best of the Naples luxury lifestyle. Where timeless architecture, tropical beauty, and an unrivaled location come together in perfect harmony.

160 16th Avenue S, Naples
$16,500,000
5 Beds ⋅ 7 Baths ⋅ 226013767 MLS
“Taking Old Naples charm to a new level,” this extraordinary residence is a masterful tribute to the previous owner, this beautifully reimagined renovation came to light where no detail was overlooked and nothing was left untouched. Thoughtfully presented by Limitless Development, C&E Builders, and with interiors by Knot & Tide Interiors this home is a true showcase of craftsmanship, design, and elevated coastal luxury. From the moment you enter, rich hardwood flooring, custom architectural accents, dramatic ceilings, and a stunning fireplace create a warm yet sophisticated ambiance. The heart of the home is a spectacular chef’s gourmet kitchen designed for both everyday living and elegant entertaining, featuring dual islands, top-of-the-line appliances, bespoke cabinetry, and a fully appointed butler’s pantry that functions as a secondary prep kitchen. The resort-inspired primary retreat offers a private sanctuary with spa-like finishes and refined detailing. Two more full bedrooms and baths on the first floor round out the seamless first floor, while a spacious loft and two beautifully appointed upstairs guest bedrooms provide comfort and privacy for family and visitors alike. Designed to embrace the Naples indoor-outdoor lifestyle, the home offers multiple porches and inviting outdoor sitting areas, perfect for morning coffee, sunset gatherings, or quiet relaxation surrounded by lush surroundings. Ideally located in prestigious Aqualane Shores, just moments from the world-class Third Street South and Naples Beach, this exceptional property offers the rare combination of historic inspiration, modern luxury, and an unbeatable location. Completing the transformation, the entire property has been meticulously renovated with no expense spared, including a brand-new resort-style pool and spa and an expansive outdoor living environment designed for true luxury entertaining. This spectacular outdoor setting creates a private resort experience, perfectly complementing the home’s extensive renovation and reinforcing its status as a one-of-a-kind Naples showcase. A true statement residence that honors Naples’ heritage while delivering a completely reimagined luxury living experience.

266 15TH Avenue S, Naples
$8,900,000
5 Beds ⋅ 6 Baths ⋅ 226017409 MLS
Nestled in prestigious Aqualane Shores, this exceptional waterfront residence offers refined coastal elegance paired with effortless Gulf access—all while remaining high and dry, with no history of water intrusion into the house. Designed by the renowned architectural firm MHK, the home blends timeless coastal sophistication with relaxed West Indies influences, creating an inviting and luxurious retreat. Boasting five spacious bedrooms, four full bathrooms, two half baths, and office; the home offers an ideal layout for both everyday living and entertaining. Inside, you'll find exquisite white pine and French oak flooring complemented by elegant marble accents, along with custom cabinetry that adds both style and functionality. The chef’s kitchen is truly a showpiece—featuring premium gas Miele appliances, a double oven, and a wine room—perfect for hosting and culinary enthusiasts. Seamlessly transition to outdoor living where a heated pool and spa, fully equipped outdoor kitchen, expansive patio, and serene sunroom provide the perfect setting to relax and entertain while enjoying tranquil water views. Boating enthusiasts will appreciate the state-of-the-art dock, complete with a 20,000-pound boat lift, offering direct canal access to the Gulf of Mexico for the ultimate Southwest Florida lifestyle. This is waterfront luxury living at its finest—where design, comfort, and location come together in perfect harmony.

628 21st Avenue S, Naples
$16,995,000
6 Beds ⋅ 8 Baths ⋅ 226011285 MLS
NOW COMPLETE & MOVE-IN READY!!! A collaboration between the area’s most respected luxury teams—Toscana Homes, Stofft Cooney Architects, and W Design—this new construction estate blends impeccable craftsmanship with striking, timeless design in one of Naples’ most coveted locations. The home offers 6 bedrooms, including two full primary suites—great for multigenerational living or long-term guests. Five suites sit upstairs, each with its own bath, arranged around a large upper-level living room that functions as a private retreat separate from the main floor. The kitchen features custom Soho cabinetry, Wolf/Sub-Zero appliances, and a fully equipped butler’s pantry. A first-floor club room with a wine feature wall opens directly to the outdoor living areas, giving the main level an easy indoor/outdoor flow. The southern exposure pool area gets sun all day and includes a generous covered lanai for dining and lounging. The corner lot allows for an unusually large landscaped side yard—rare for Aqualane Shores and works well for kids, pets, or added recreation space. Additional details include a 3-stop elevator, 3 car garage with a dedicated golf-cart entrance, full-house generator, and an 11-FOOT ELEVATION. Set in the most walkable part of Aqualane Shores, the home puts the beach, 3rd Street’s shops and restaurants, and direct Gulf access all within easy reach. A thoughtful, well-executed home from an award-winning team, built for both everyday living and effortless entertaining.

408 16th Avenue S, Naples
$9,900,000
5 Beds ⋅ 6 Baths ⋅ 225078983 MLS
Back on market, buyer did not perform. The perfect location in Old Naples, just one block from the beach and two blocks from the fine dining and boutiques of Third Street South. This exceptional all-concrete custom home crafted by Grand Bay Development embodies the best of Naples' luxury living. Built to a 15 foot elevation for peace of mind. Featuring 5 bedrooms, 2 dens, plus a flex room off of the pool area and 5 & 1/2 bathrooms. Every detail reflects a commitment to world-class design and craftsmanship, from the curated global finishes to the tropical connection between indoor and outdoor living. The gourmet kitchen adorned with Cristallo Quartzite serves as the heart of the home, with beautiful hardwoods that are increasingly rare, and surrounded by spectacular greenery that creates a sense of privacy and retreat. A custom quartz and agate wet bar opens to the elegant great room, where walls of glass frame western facing terraces. The primary suite offers an elevated sense of serenity with a private balcony with partial gulf views. A rooftop terrace provides panoramic views of the coastline, breathtaking sunsets, and the Naples skyline. The southwest-facing lanai features a vanishing-edge saltwater pool, expansive covered entertaining areas protected by screens and shutters, and meticulously designed tropical landscaping. Combining architectural integrity, global inspiration, and an unmatched location, this residence defines a warm and inviting luxury along the Naples coast.

1441 Gulf Shore Boulevard S, Naples
$89,995,000
225075672 MLS
A once-in-a-generation opportunity in the heart of Aqualane Shores. Encompassing nearly 4 acres across 7 contiguous lots, this extraordinary waterfront assemblage offers an unmatched 858 feet of continuous water frontage along a deepwater canal and Naples Bay. A true rarity in Naples, it combines panoramic bay views, direct Gulf access with no bridges, and three grandfathered-in boathouses - making it both a boater’s paradise and a developer’s dream. The site is nearly cleared and ready for transformation, presenting the perfect canvas for a world-class private compound or multiple luxury estates. Situated just moments from the beach and Naples’ iconic Third Street South, this is among the largest and most significant land offerings ever presented in Aqualane Shores. A legacy property of rare scale and potential.

820 Jamaica Lane, Naples
$8,900,000
4 Beds ⋅ 5 Baths ⋅ 224085873 MLS
Experience the best of both worlds in this coastal home in Aqualane Shores, where unrestricted gulf-access boating meets the quiet luxury of Third Street South's shops and dining. The expansive 100-foot of dockage space provides ample space for an oversized vessel or multiple water toys. Just steps from the Naples Yacht Club, this residence offers the ideal balance of relaxation and adventure. Get a workout in the lap pool, or retreat to the private top-floor primary suite with a balcony overlooking Naples Bay. The spacious central living room features floor-to-ceiling sliders, creating an open, airy ambiance. The garage is equipped with built-in car lifts and an electric charging station, ideal for the modern car enthusiast. A fun and casual home that puts the best of Naples right at your doorstep.

636 14th Avenue S, Naples
$4,950,000
223078778 MLS
Amidst some of Naples' most exquisite and elegant waterfront homes sits a rare opportunity that offers a home site to design and build your dream home. This property is located on tranquil and dolphin-friendly Kite’s Cove, in highly sought after Aqualane Shores, and has a no bridge access to the Gulf. Southern exposure with approximately 80 feet on the water and a fantastic private, grandfathered in, cut-out dock with two boat lifts. Only a few short blocks to beach access and Third Street South's restaurants and chic shops.

688 21st Avenue S, Naples
$12,400,000
5 Beds ⋅ 7 Baths ⋅ 223012032 MLS
Featuring preferred southern exposure and comfortably situated in the quaint waterfront neighborhood of Aqualane shores is this new construction home at 508 16th Avenue South. Thoughtfully designed by MHK Architects this home features 5 bedrooms and 7 baths, with 5,593 square feet of thoughtfully designed open living space. The outdoor living and massive southern exposure outdoor deck, provide year around sun exuding the Florida luxury living lifestyle! Recently completed in early 2026 this home also features a 48 kilowatt full house generator to power all your needs. Fiber optic and natural gas provide the modern day livability discerning buyers expect. It is a very brief stroll to the dining, shopping and lifestyle hub of third street south, as well the sugar sand of our Naples beaches! Do not miss this fantastic opportunity to own new construction, waterfront southern exposure in Old Naples! This is a boaters dream with direct gulf and backwater access!

508 16th Avenue S, Naples