Olde Naples Homes with Upper Level Primary Interior

Olde Naples Homes with Upper Level Primary Interior

Welcome to Olde Naples, a picturesque gem nestled in the heart of Naples, Florida, within the beautiful Collier County. This charming community is renowned for its stunning architecture, lush landscapes, and a vibrant atmosphere that perfectly captures the essence of coastal living.

Olde Naples is characterized by its quaint, tree-lined streets, where you’ll find a delightful mix of historic homes and modern residences, each exuding its unique charm. Among these, the homes with upper-level primary interiors stand out, offering an exquisite blend of luxury and comfort. These thoughtfully designed residences feature spacious layouts that maximize natural light and provide breathtaking views of the surrounding area. Imagine waking up to the gentle sound of waves and enjoying your morning coffee from a private balcony, all while soaking in the serene ambiance of this coastal paradise.

Beyond the beautiful homes, Olde Naples boasts a rich array of amenities, including upscale boutiques, gourmet dining, and pristine beaches just a stone’s throw away. The community’s commitment to preserving its historic charm while embracing modern conveniences makes it a highly sought-after destination for both residents and visitors alike.

Whether you’re looking for a tranquil retreat or a vibrant lifestyle, Olde Naples offers the perfect balance. Discover the allure of homes with upper-level primary interiors, where luxury meets coastal charm, and experience the best of what Naples has to offer. Come and explore this enchanting community, where your dream home awaits!

Newest Olde Naples Homes with Upper Level Primary Interior

6 Beds ⋅ 7 Baths ⋅ 226024712 MLS

This Gulf-front masterpiece offers an unparalleled blend of location, luxury, Gulf views, and resort-style living. Completely rebuilt in 2024 by Kukk Architecture and The Lykos Group with the exception of one exterior wall to utilized the grandfathered setbacks and maximize an oversized building envelope. The home has experienced no water intrusion in living areas during recent weather events. The residence combines historic charm with sophisticated elegance. Originally built in 1886, the home underwent an extensive three-year renovation and reconstruction. Now practically new, the residence preserves its heritage, grandfathered footprint, and distinctive character while offering modern luxury throughout. The 6,100-square-foot, fully air-conditioned living space maximizes its premier beachfront setting. The well-designed layout offers five spacious bedrooms, five full and two half baths, a private study, and a flexible sixth bedroom. Sweeping Gulf views provide a stunning backdrop. The gourmet kitchen boasts dual Cristallo quartzite islands, top-tier appliances, custom cabinetry, and a service kitchen. Additional features include a private gated entry, two fireplaces, elevator, whole-house generator, automated screens/shutters, water filtration, and ultra-efficient air conditioning. Perfectly positioned on the Gulf, just moments from the dining and boutique shopping of Third Street South and Fifth Avenue South. A rare opportunity in the heart of Old Naples.

55 13th Avenue S, Naples

3 Beds ⋅ 4 Baths ⋅ 226022088 MLS

On a desired, tree-lined street in the heart of Old Naples, this exceptional residence offers refined coastal luxury just moments from the pristine Gulf beaches and the acclaimed dining, shopping and entertainment of Fifth Avenue South. Situated within The Gables on Sixth Street, an exclusive enclave of only seven residences designed by Harrell & Associates, the home combines privacy, sophistication and an unrivaled location. A gated rear entrance leads to an air-conditioned three-car garage complete with a vehicle lift and custom built-in storage. Spanning more than 4,300 square feet of beautifully designed living space, the light-filled interior showcases rich hardwood and stone flooring, elegant architectural details and a seamless open-concept floor plan. The redesigned chef’s kitchen serves as the heart of the home, featuring premium appliances, custom cabinetry, an oversized island ideal for entertaining and a climate-controlled wine room with capacity for more than 450 bottles. Designed to embrace the Naples lifestyle, expansive walls of glass connect the great room to a stunning outdoor living area. The covered lanai, highlighted by striking glass floor panels suspended above the pool and spa, creates a dramatic architectural focal point. A fully equipped summer kitchen, gas fireplace and retractable screens provide the perfect setting for year-round entertaining and relaxation. The second floor offers three generously sized en-suite guest bedrooms, while the luxurious primary suite serves as a private retreat complete with a serene balcony and spa-inspired bath featuring exceptional finishes and thoughtful design. Blending timeless elegance, modern comfort and an extraordinary convenient location, this residence represents a rare opportunity to enjoy a luxurious coastal lifestyle and the best of Old Naples living.

32 6th Street S, Naples

4 Beds ⋅ 5 Baths ⋅ 226014208 MLS

Accented with the color of morning-lit palms, this 2016 West Indies style home by Jeff Harrell and Associates offers a modern touch to the classic Naples charm. Located in the heart of Olde Naples, you’re on the doorstep of everything the city has to offer. Walking distance to 5th Avenue South and 3rd Street offers an endless variety of dining and shopping experiences. Boater? Naples Bay is a short walk away with the Naples Marina just across the street. Looking for the Beach? just head west. Find your spot in the sand with over 40 public beach access points to choose from. The home features 4 bedrooms, 4.5 baths and a 2 car garage. The open floor plan features beautiful hardwood flooring in each room, soaring ceilings, and floor-to-ceiling windows offering endless natural light. Perched at the Western end of Jumby Bay, this home stands out with unmatched privacy and extra space. It is the only residence in the development whose pool does not back up to another home, delivering a truly secluded outdoor area. In addition, 912 sits on a larger .19-acre lot compared to the .14-acre lots of central homes, creating a generous yard beside the pool. The chef’s kitchen is equipped with premium appliances including a Viking oven and cooktop, Miele refrigerator, Miele dishwasher, Miele convection microwave, and Uline wine cooler. A huge center island serves as the heart of the home, perfect for food preparation, casual dining, or buffet service. The lushly landscaped lanai is accessible from the great room and kitchen through multiple French doors, offering a covered and screened seating and dining area with cabana bath, plus a gas grill in the open space. Just beyond lies the sun-drenched 32-foot pool, spacious spa, and pergola-covered seating. This is the perfect spot for relaxing or entertaining day or night. Off the pool, you’ll find a private first-floor guest bedroom. On the second floor, The oversized master suite boasts dual walk-in closets designed for maximum functionality, a floating tub, and a large separate shower. Down the hall you’ll find a guest room with an en-suite bathroom and balcony. Above the garage and accessible from the main residence or a private alleyway entrance sits a versatile bonus space that can serve as a guest casita, office, or fitness center complete with a private bath. The HOA fee includes landscaping and pool maintenance, with weekly cleanings. On-street improvements also provide additional parking right on 9th Ave. Schedule your private showing today and make 912 9th Ave S. your new address in paradise!

912 9th Avenue S, Naples

6 Beds ⋅ 6 Baths ⋅ 226018147 MLS

Experience the pinnacle of beachfront luxury from this extraordinary Naples coastal estate, where timeless Bermuda-inspired architecture meets effortless modern elegance. Perfectly positioned along 108 feet of pristine Gulf frontage, this six-bedroom residence offers an unparalleled opportunity to own a private sanctuary directly on the sugar-white sands of Naples. Evoking the refined charm of Alys Beach, the home’s striking white stucco exterior, parapet walls, and lush manicured landscaping create a serene and sophisticated coastal presence. Ideally located just steps from the new Four Seasons Naples Beach Club and moments from the boutiques and dining of downtown Olde Naples, the property offers a rare combination of privacy, prestige, and walkable convenience. Inside, expansive living spaces are bathed in natural light through walls of French doors that frame breathtaking panoramic views stretching from sand to sea. Thoughtfully designed for both grand entertaining and relaxed coastal living, the residence offers a seamless flow between formal and casual gathering spaces. A dramatic double living room and elegant dining area, complete with a custom beverage station and bar, create an unforgettable setting for hosting family and guests. The chef’s kitchen opens effortlessly to a warm and inviting family room and features a large center island, stone countertops, premium appliances, and a fully appointed butler’s pantry with wine refrigeration. Two luxurious primary suites—one on the main level and another upstairs with a private balcony overlooking the Gulf—provide tranquil retreats designed for ultimate comfort and privacy. A dedicated office on the main floor further enhances the home’s functionality for today’s lifestyle. Every detail throughout the residence reflects exceptional craftsmanship, timeless design, and understated sophistication. From the refined architectural elements to the seamless indoor-outdoor connection, this remarkable property embodies Naples beachfront living at its absolute finest.

23 6TH AVE N, Naples

5 Beds ⋅ 6 Baths ⋅ 226017504 MLS

Perfectly positioned on a coveted corner of 2nd Street South and 7th Avenue South, this exceptional Olde Naples estate captures the essence of timeless coastal elegance paired with elevated modern design. Enveloped beneath a canopy of majestic oak trees and oriented for prized southern exposure, the residence is bathed in natural light, creating a luminous and inviting ambiance throughout. Masterfully designed by MHK Architecture, this five-bedroom plus den home is a refined interpretation of the classic Florida cottage, thoughtfully reimagined with sophisticated architectural detail and contemporary flair. Interiors are curated with an uncompromising eye—where bespoke finishes, clean lines, and warm textures come together to create a seamless balance of comfort and luxury. Indoor outdoor living is perfectly matched with a private lush landscaped backyard featuring a gas outdoor kitchen, fireplace & heated pool & spa. Just two blocks from the sugar-white sands of the Gulf and moments from the world-class boutiques and dining of Fifth Avenue South, the home offers an unparalleled walkable lifestyle in one of Naples’ most prestigious enclaves. This is a rare opportunity to own a signature property in the heart of Olde Naples—where iconic charm, thoughtful design, and modern sophistication converge in effortless harmony.

685 2nd Street S, Naples

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

4 Beds ⋅ 5 Baths ⋅ 226011149 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. One of the few Old Naples residences offering both immediate Gulf access and a 5+ car garage, this timeless Italian-inspired home presents a rare combination of coastal proximity, scale, and functionality. Ideally positioned just steps from the pristine Gulf beaches—directly across the street—and adjacent to the highly anticipated Four Seasons Resort Naples and its reimagined oceanfront golf campus, the property benefits from one of the most compelling locations in Naples, blending lifestyle with long-term value. Encompassing over 6,800 square feet of interior living space, the residence showcases elegant architectural details, warm finishes, and expansive gathering areas designed for both everyday comfort and grand-scale entertaining. The impressive living room offers a refined yet inviting setting, complete with a billiard table and seamless flow into the main living areas. A standout feature is the presence of two private guest suites, each with its own kitchen—providing exceptional flexibility for extended family, guests, or staff while maintaining privacy and independence. Built with exceptional strength and durability, the home is equipped with a private elevator, full-house diesel generator, rainwater recycling system, and automatic irrigation, delivering a level of infrastructure and peace of mind rarely found in this location. Car enthusiasts and collectors will immediately appreciate the significance of the 5+ car garage spanning over 2,000 square feet—a truly rare offering in Old Naples. This expansive space accommodates a substantial vehicle collection while also allowing for a workshop, storage, or additional lifestyle uses seldom available this close to the Gulf. The expansive rooftop terrace serves as the home’s signature outdoor retreat, offering Gulf views, refreshing coastal breezes, and an ideal setting for sunset entertaining above it all. A rare and compelling opportunity to own a substantial Old Naples residence that uniquely combines Gulf proximity, exceptional infrastructure, and immediate adjacency to the transformative Four Seasons beachfront development—positioning this home not only as a lifestyle purchase, but as a strategic long-term investment.

200 S Golf Drive, Naples

6 Beds ⋅ 6 Baths ⋅ 226001239 MLS

An extraordinary Old Naples beachfront estate, this rare offering encompasses approximately .67 acres with an impressive 169 feet of pristine Gulf frontage, delivering an unparalleled combination of privacy, scale, and a prime location just blocks from the world-class boutiques, galleries, and dining of Fifth Avenue South and Third Street South. Designed by acclaimed architect Richard Morris, the art deco–inspired residence was masterfully conceived to frame sweeping Gulf views and sunsets, showcase fine art and create a seamless indoor–outdoor living experience that feels grand and intimate. A dramatic arrival unfolds into a soaring 22-foot foyer, where a sweeping staircase and private elevator lead to an elevated art gallery, immediately establishing the home’s architectural presence and refined elegance. The light-filled great room serves as the heart of the residence, flowing effortlessly into the dining area, expansive lanai and a sophisticated lounge highlighted by custom millwork and a wet bar, ideal for entertaining against a backdrop of endless blue horizons. A sculptural spiral staircase ascends to a private observation deck, offering breathtaking panoramic views of the Gulf and unforgettable sunsets. The generous kitchen suite is designed for effortless hosting, featuring an open-concept layout with indoor and outdoor dining counters, a walk-in pantry and high-end stainless-steel appliances. The primary suite is a secluded beachfront retreat with direct access to a Gulf-front balcony, pool and lanai, complemented by a spa-inspired bath with a glass-enclosed walk-in shower and mesmerizing water views. Just a short distance away, a private bedroom or den offers flexibility as a refined home office or serene sanctuary. The east wing of the home hosts four spacious en-suite bedrooms and a dedicated laundry, while the northeast bedroom, bathed in exceptional natural light with abundant storage, lends itself beautifully as an artist’s studio or creative space. Outdoors, an elevated screened courtyard and lushly landscaped gardens create a tranquil oasis for year-round enjoyment, while the expansive covered lanai, complete with a kitchenette and dining area, invites relaxed coastal entertaining. Built with exterior block construction, a first-floor elevation exceeding 19 feet above NGVD and electric storm shutters, the home offers exceptional peace of mind along with enduring quality. Professional landscaping, architectural lighting, and iconic outdoor sculptures complete this remarkable setting. Beyond its immediate beauty, the property also presents an extraordinary future opportunity, with the potential to create a 10,000–15,000 square-foot custom beachfront estate, making this a once-in-a-generation offering that blends luxury, lifestyle and limitless possibility in one of Naples desired beachfront locations.

30 3rd Avenue S, Naples

5 Beds ⋅ 8 Baths ⋅ 226002046 MLS

A landmark, custom built, Old Naples estate just four homes from the Gulf. Elevated and recently renovated, this exceptional residence offers over 7,500 square feet of refined AC-living with timeless architecture and exquisite craftsmanship. Features include a grand two-story foyer, coffered ceilings, rich millwork, library, formal dining, and expansive living spaces filled with natural light. The chef’s kitchen boasts Wolf and Sub-Zero appliances, dual islands, marble prep areas, butler’s pantry, and wine cellar. The luxurious master suite offers a sitting area, dual walk-in closets, spa bath, and private balcony. Outdoor living includes a heated, salt system pool and spa, outdoor kitchen, fireplace, lush landscaping, and shaded entertaining areas. Rare, air-conditioned garage for 10+ vehicles, impact windows and doors, private elevator, and generator. High and dry, moments to beaches, dining, and shopping—this is Old Naples luxury at its finest.

140 3rd Avenue S, Naples

3 Beds ⋅ 5 Baths ⋅ 225072058 MLS

In the heart of Olde Naples, this 2020-built courtyard residence blends timeless coastal architecture with refined, resort-style living just moments from 3rd Street South and Naples’ pristine beaches. Shell-stone travertine floors introduce light-filled living and dining spaces designed for effortless entertaining. The chef’s kitchen is appointed with Sub-Zero refrigeration, Lacanche gas cooking, custom cabinetry, and a thoughtfully designed wet bar. A family room opens seamlessly to the private courtyard, creating true indoor-outdoor living. Upstairs, the serene primary suite offers volume ceilings, tailored millwork, and a spa-inspired bath, joined by two en-suite guest suites and a flexible den/office. A private elevator services both levels. The walled courtyard becomes a secluded retreat with heated plunge pool and spa, outdoor kitchen with built-in grill, surround sound, and lush vertical greenery for privacy. Impact-rated windows and doors, smart-home automation, natural gas, metal roof, and a generous two-car garage with storage complete this thoughtfully engineered residence. Beautifully scaled and impeccably maintained, 909 10th Avenue South offers the rare combination of walkability, architectural integrity, and lock-and-leave ease in Olde Naples.

909 10th Avenue S, Naples

3 Beds ⋅ 3 Baths ⋅ 225022012 MLS

Offering spectacular southern exposure with direct water views over Naples Bay, this private residence features soaring 10-foot ceilings, a private elevator, elegant wood floors, French doors, and custom plantation shutters on numerous windows. The open floor plan seamlessly integrates the living, dining, and kitchen areas, extending to a spacious terrace with breathtaking water views. The wonderful eat-in kitchen is designed for both functionality and charm. The expansive master suite includes a separate tub and shower, custom walk-in closets, and a generous terrace perfect for soaking in the southern sun while watching boats set sail. Designed for exceptional outdoor entertaining, the property boasts multiple spaces, including a rooftop spa, built-in grill, and uninterrupted water views. A unique dual entry—one of which offers convenient street-level access—ensures ease for guests coming and going. Completing this remarkable property is a secure two-car garage located under the building.

1001 10th Avenue S Unit 211, Naples

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