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British Cayman–inspired architecture, fresh interiors, and a coveted Old Naples location come together at this beautifully remodeled residence. Just three blocks from the Gulf beaches and five blocks north of Fifth Avenue South, the home places shopping, dining, and days by the water within easy reach. The property remained free of water intrusion during both Hurricanes Ian and Milton. Set behind lush landscaping and a circular paver driveway, custom mahogany doors open to a spacious great room with views across the pool and tropical terrace. French oak flooring, a soft neutral palette, and carefully selected designer finishes bring warmth and continuity throughout the two-story layout, which includes four bedrooms, three full baths, and one half baths. The main-level primary suite features two walk-in closets and a beautifully appointed bath. A generous kitchen with premium appliances and a gas cooktop provides plenty of space to prepare meals and gather, while the outdoor kitchen makes alfresco entertaining equally inviting. Andersen impact windows and doors add to the home’s thoughtful appointments. Outside, the private heated pool and spa anchor a lush retreat with room for lounging, dining, and hosting friends. From quiet mornings on the terrace to beach afternoons and evenings on Fifth Avenue South, this home offers an effortless way to enjoy the Old Naples lifestyle.

4 Beds ⋅ 4 Baths ⋅ 226040276 MLS

British Cayman–inspired architecture, fresh interiors, and a coveted Old Naples location come together at this beautifully remodeled residence. Just three blocks from the Gulf beaches and five blocks north of Fifth Avenue South, the home places shopping, dining, and days by the water within easy reach. The property remained free of water intrusion during both Hurricanes Ian and Milton. Set behind lush landscaping and a circular paver driveway, custom mahogany doors open to a spacious great room with views across the pool and tropical terrace. French oak flooring, a soft neutral palette, and carefully selected designer finishes bring warmth and continuity throughout the two-story layout, which includes four bedrooms, three full baths, and one half baths. The main-level primary suite features two walk-in closets and a beautifully appointed bath. A generous kitchen with premium appliances and a gas cooktop provides plenty of space to prepare meals and gather, while the outdoor kitchen makes alfresco entertaining equally inviting. Andersen impact windows and doors add to the home’s thoughtful appointments. Outside, the private heated pool and spa anchor a lush retreat with room for lounging, dining, and hosting friends. From quiet mornings on the terrace to beach afternoons and evenings on Fifth Avenue South, this home offers an effortless way to enjoy the Old Naples lifestyle.

33 3rd Street S, Naples

$16,990,000

Quietly situated at the southernmost end of Gulf Shore Boulevard South, directly across from beach access, this exceptional Olde Naples estate is a true crown jewel, spanning more than one-half acre. Designed by John Cooney of Stofft Cooney Architects and meticulously refurbished throughout, the residence reflects uncompromising craftsmanship and timeless sophistication and can be acquired turnkey furnished for immediate occupancy. From the moment of arrival, the home makes a lasting impression. Flickering gas lanterns, a gracious front porch, and classic symmetrical architecture accented by exquisite millwork create an inviting sense of elegance. Inside, refined finishes abound, including mahogany front doors, rift-sawn white oak flooring, and a striking vaulted ceiling detail upon entry. The living room’s balanced symmetry and detailed millwork flow seamlessly into the gourmet kitchen and dining area, anchored by a 60" Wolf dual-fuel range featuring six burners, an infrared charbroiler, and an infrared griddle. Additional highlights include a Sub-Zero side-by-side refrigerator and freezer, integrated refrigerator drawer systems, and two Miele dishwashers—perfectly suited for both everyday living and entertaining. Thoughtfully curated spaces throughout the home include a bespoke media room with soundproofed walls and a Savant sound system, a handsome study with custom built-in display cabinetry overlooking the pool, a fully reimagined bar and library, and a dedicated fitness studio complete with a steam shower—each space designed for both function and refined living. The estate is comprised of five well-appointed bedrooms, four of which feature en-suite baths, offering refined accommodations for both residents and guests alike. The Master Suite and Bath offer a true private retreat, enveloping you in comfort from head to toe. A tranquil sitting area overlooks the spa and pool, providing a serene backdrop for rest and reflection. Crown moldings and elegant casings throughout enhance the sense of refined craftsmanship, creating a space that feels like a peaceful escape—while remaining unmistakably at home. Following a complete renovation inside and out, the outdoor living spaces are equally compelling. An expansive, oversized porch is designed for rest and relaxation, offering an exceptional poolside setting framed by a preserved Wild Oak tree—an enchanting natural centerpiece that enhances the estate’s sense of serenity and timeless charm. Additional elevated improvements include two side-mounted car lifts, whole-house generator, dual dehumidification systems, a steam shower within the fitness studio underscoring the home’s exceptional level of care, resilience, and thoughtful investment.

6 Beds ⋅ 8 Baths ⋅ 226034183 MLS

Quietly situated at the southernmost end of Gulf Shore Boulevard South, directly across from beach access, this exceptional Olde Naples estate is a true crown jewel, spanning more than one-half acre. Designed by John Cooney of Stofft Cooney Architects and meticulously refurbished throughout, the residence reflects uncompromising craftsmanship and timeless sophistication and can be acquired turnkey furnished for immediate occupancy. From the moment of arrival, the home makes a lasting impression. Flickering gas lanterns, a gracious front porch, and classic symmetrical architecture accented by exquisite millwork create an inviting sense of elegance. Inside, refined finishes abound, including mahogany front doors, rift-sawn white oak flooring, and a striking vaulted ceiling detail upon entry. The living room’s balanced symmetry and detailed millwork flow seamlessly into the gourmet kitchen and dining area, anchored by a 60" Wolf dual-fuel range featuring six burners, an infrared charbroiler, and an infrared griddle. Additional highlights include a Sub-Zero side-by-side refrigerator and freezer, integrated refrigerator drawer systems, and two Miele dishwashers—perfectly suited for both everyday living and entertaining. Thoughtfully curated spaces throughout the home include a bespoke media room with soundproofed walls and a Savant sound system, a handsome study with custom built-in display cabinetry overlooking the pool, a fully reimagined bar and library, and a dedicated fitness studio complete with a steam shower—each space designed for both function and refined living. The estate is comprised of five well-appointed bedrooms, four of which feature en-suite baths, offering refined accommodations for both residents and guests alike. The Master Suite and Bath offer a true private retreat, enveloping you in comfort from head to toe. A tranquil sitting area overlooks the spa and pool, providing a serene backdrop for rest and reflection. Crown moldings and elegant casings throughout enhance the sense of refined craftsmanship, creating a space that feels like a peaceful escape—while remaining unmistakably at home. Following a complete renovation inside and out, the outdoor living spaces are equally compelling. An expansive, oversized porch is designed for rest and relaxation, offering an exceptional poolside setting framed by a preserved Wild Oak tree—an enchanting natural centerpiece that enhances the estate’s sense of serenity and timeless charm. Additional elevated improvements include two side-mounted car lifts, whole-house generator, dual dehumidification systems, a steam shower within the fitness studio underscoring the home’s exceptional level of care, resilience, and thoughtful investment.

1963 Gulf Shore Boulevard S, Naples

$5,950,000

A beach bungalow in the heart of Old Naples, this charming three-bedroom, two-bath residence sits on an expansive 150-by-100-foot corner lot just three blocks from the Gulf. Surrounded by mature trees and lush landscaping, the property offers a wonderful sense of privacy while capturing the relaxed, timeless character of coastal Naples. The home is filled with natural light and offers inviting indoor-outdoor living, providing an opportunity to enjoy the property as it is, thoughtfully reimagine the existing residence or take advantage of the generous homesite to create a new custom home. Ideally at the corner of Third Street North and Fourth Avenue North, 444 Third Street North places the beach, Fifth Avenue South and Third Street South all within easy reach.

3 Beds ⋅ 3 Baths ⋅ 226034533 MLS

A beach bungalow in the heart of Old Naples, this charming three-bedroom, two-bath residence sits on an expansive 150-by-100-foot corner lot just three blocks from the Gulf. Surrounded by mature trees and lush landscaping, the property offers a wonderful sense of privacy while capturing the relaxed, timeless character of coastal Naples. The home is filled with natural light and offers inviting indoor-outdoor living, providing an opportunity to enjoy the property as it is, thoughtfully reimagine the existing residence or take advantage of the generous homesite to create a new custom home. Ideally at the corner of Third Street North and Fourth Avenue North, 444 Third Street North places the beach, Fifth Avenue South and Third Street South all within easy reach.

444 3rd Street N, Naples

$1,999,000

Stunning designer furnished by Cocoon Gallery, 2 bedroom, 2.5 bath unit in the highly desirable The Mark on 8th in Olde Naples. Located on the third floor (with elevator access), unit 309 enjoys enhanced privacy with abundant natural light. Approximately 500 sq. ft. of outdoor living space spread across three furnished terraces. Recently completed in 2025 with the best-in-class finishes including a 4-burner Wolf gas stove, Wolf microwave, Miele dishwasher and Sub-Zero refrigerator/freezer. Great room living/dining area with volume ceilings create a spacious atmosphere ideal for entertaining with a convenient half bath. Each bedroom is ensuite with a walk in closet. Assigned garage space and storage under building plus plenty of guest parking. Residents of The Mark enjoy access to luxury amenities including heated pool and spa, an expansive sun deck, outdoor grilling station and fire pit, pool baths and an outdoor shower, community clubhouse, sauna and fitness center. The Mark is pet friendly with a 2 pet limit. Located steps from boutiques, restaurants and galleries of 5th Avenue and a short stroll to the beach.

2 Beds ⋅ 3 Baths ⋅ 226032535 MLS

Stunning designer furnished by Cocoon Gallery, 2 bedroom, 2.5 bath unit in the highly desirable The Mark on 8th in Olde Naples. Located on the third floor (with elevator access), unit 309 enjoys enhanced privacy with abundant natural light. Approximately 500 sq. ft. of outdoor living space spread across three furnished terraces. Recently completed in 2025 with the best-in-class finishes including a 4-burner Wolf gas stove, Wolf microwave, Miele dishwasher and Sub-Zero refrigerator/freezer. Great room living/dining area with volume ceilings create a spacious atmosphere ideal for entertaining with a convenient half bath. Each bedroom is ensuite with a walk in closet. Assigned garage space and storage under building plus plenty of guest parking. Residents of The Mark enjoy access to luxury amenities including heated pool and spa, an expansive sun deck, outdoor grilling station and fire pit, pool baths and an outdoor shower, community clubhouse, sauna and fitness center. The Mark is pet friendly with a 2 pet limit. Located steps from boutiques, restaurants and galleries of 5th Avenue and a short stroll to the beach.

201 8th St S #309, Naples

$6,495,000

Completely reimagined and finished in 2025, this beautifully renovated Old Naples residence lives like a new home. Offering just under 3,000 square feet, the property includes four bedrooms and 5.5 baths designed for effortless luxury living. An open layout connects the living, dining and kitchen areas, creating an inviting flow for everyday living and entertaining. The chef's kitchen features a Wolf six-burner gas range, Sub-Zero refrigerator, and Sub-Zero wine cooler with additional refrigerator and ice drawer. Cristallo quartzite countertops, a marble-clad island and custom Crystal cabinetry combine elegance with function. The primary suite offers vaulted ceilings, a sitting area and views of the pool. Its spa-style bath includes a Kohler soaking tub, rain and body-spray shower, and custom California Closets with integrated lighting. Outside, a new saltwater pool with spa creates a resort-like setting. A full outdoor kitchen with grill, refrigerator, sink and TV makes entertaining easy. Near Third Street South dining, shopping and Naples white sand beach.

4 Beds ⋅ 6 Baths ⋅ 226011370 MLS

Completely reimagined and finished in 2025, this beautifully renovated Old Naples residence lives like a new home. Offering just under 3,000 square feet, the property includes four bedrooms and 5.5 baths designed for effortless luxury living. An open layout connects the living, dining and kitchen areas, creating an inviting flow for everyday living and entertaining. The chef's kitchen features a Wolf six-burner gas range, Sub-Zero refrigerator, and Sub-Zero wine cooler with additional refrigerator and ice drawer. Cristallo quartzite countertops, a marble-clad island and custom Crystal cabinetry combine elegance with function. The primary suite offers vaulted ceilings, a sitting area and views of the pool. Its spa-style bath includes a Kohler soaking tub, rain and body-spray shower, and custom California Closets with integrated lighting. Outside, a new saltwater pool with spa creates a resort-like setting. A full outdoor kitchen with grill, refrigerator, sink and TV makes entertaining easy. Near Third Street South dining, shopping and Naples white sand beach.

1355 4th Street S, Naples

$9,995,000

A masterfully crafted collaboration between Jeffrey Fisher Home, renowned architect JMDG, and the highly respected Waterside Builders; this newly completed Olde Naples residence blends elevated design with luxurious livability—just four blocks to the beach and two blocks from the charm of 3rd Street South. Every element of the home reflects attention to detail and timeless sophistication: European white oak floors, custom cabinetry and millwork, floor-to-ceiling glass, and intricate stained oak architectural ceilings. The open-concept floor plan flows through a sunlit study, elegant dining space, and stunning backlit bar into a designer kitchen outfitted with Miele, Wolf, and Sub-Zero appliances, plus a walk in pantry and first-floor laundry. The first-floor primary suite is a true retreat with immediate access to the pool and outdoor living areas. Framed by impact sliders, the living room opens to multiple covered spaces and a plunge / dipping pool and spa. A full summer kitchen and expansive outdoor deck make entertaining effortless. Upstairs offers exceptional flexibility and privacy with three en-suite bedrooms, a large bonus room, a second laundry, and a VIP guest suite. Control4 home automation, generator, natural gas, and electric roll-down screens and shutters provide ultimate comfort, security, and convenience. Positioned in one of the most sought-after pockets of Olde Naples, this bespoke property is a rare opportunity to own a truly exceptional new-construction home—steps from the Gulf, fine dining, and world-class shopping.

4 Beds ⋅ 7 Baths ⋅ 225056392 MLS

A masterfully crafted collaboration between Jeffrey Fisher Home, renowned architect JMDG, and the highly respected Waterside Builders; this newly completed Olde Naples residence blends elevated design with luxurious livability—just four blocks to the beach and two blocks from the charm of 3rd Street South. Every element of the home reflects attention to detail and timeless sophistication: European white oak floors, custom cabinetry and millwork, floor-to-ceiling glass, and intricate stained oak architectural ceilings. The open-concept floor plan flows through a sunlit study, elegant dining space, and stunning backlit bar into a designer kitchen outfitted with Miele, Wolf, and Sub-Zero appliances, plus a walk in pantry and first-floor laundry. The first-floor primary suite is a true retreat with immediate access to the pool and outdoor living areas. Framed by impact sliders, the living room opens to multiple covered spaces and a plunge / dipping pool and spa. A full summer kitchen and expansive outdoor deck make entertaining effortless. Upstairs offers exceptional flexibility and privacy with three en-suite bedrooms, a large bonus room, a second laundry, and a VIP guest suite. Control4 home automation, generator, natural gas, and electric roll-down screens and shutters provide ultimate comfort, security, and convenience. Positioned in one of the most sought-after pockets of Olde Naples, this bespoke property is a rare opportunity to own a truly exceptional new-construction home—steps from the Gulf, fine dining, and world-class shopping.

581 14th Avenue S, Naples

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