Olde Naples Homes with Multi-Story Home Style

Olde Naples Homes with Multi-Story Home Style

Welcome to Olde Naples, a charming neighborhood nestled in the heart of Naples, Florida. This historic district is located in Collier County and is renowned for its picturesque streets lined with beautiful homes. If you're looking for a home with a multi-story design, Olde Naples has plenty to offer.

With its true multi-story home style, Olde Naples boasts a variety of properties that provide ample space for families and individuals alike. Whether you're looking for a cozy two-story cottage or a grand three-story estate, you'll find the perfect fit in this idyllic neighborhood.

Living in Olde Naples means enjoying the best of both worlds - the tranquility of a residential community and the convenience of being just a stone's throw away from the vibrant city center. Residents can explore upscale boutiques, gourmet restaurants, art galleries, and pristine beaches, all within easy reach.

Don't miss the opportunity to experience the timeless beauty and elegance of Olde Naples. Discover your dream home in this enchanting neighborhood and embrace the luxurious coastal lifestyle that awaits you.

Newest Olde Naples Homes with Multi-Story Home Style

$13,500,000
5 Beds ⋅ 6.5 Baths ⋅ 226029919 MLS
Everyone Stops to Take a Picture. There are homes you walk past—and then there are homes that make you stop. Just one house from the beach in the heart of downtown Naples, this exceptional residence has become one of those unmistakable properties that catches the eye of nearly everyone who passes. People stop, admire it, and more often than not, take a picture. Inspired by the owners’ travels throughout the Mediterranean, the architecture is romantic, distinctive and beautifully detailed. At first glance, stately wrought-iron gates crowned with a pineapple finial welcome you to the property. Beyond them, twin limestone staircases gracefully sweep from either side toward the grand front entrance, creating an unforgettable sense of arrival. Look closer and the details become even more captivating: Juliet-style wrought-iron flower boxes, graceful fanlight transoms, open-air terraces, limestone accents and architectural elements reminiscent of a European villa. Then the grand front door opens to a dramatic foyer soaring 24 feet above—revealing that the magnificence of the exterior is only the beginning. It is a first impression you simply don’t forget. No wonder everyone stops to take a picture.

40 5th AVE S, Naples
$1,274,900
2 Beds ⋅ 2.5 Baths ⋅ 226026573 MLS ⋅ Franciscan BLDG.
High elevation, first-floor location, direct western exposure from your private balcony to enjoy Naples' spectacular sunsets, 2 bedrooms plus a den, in-unit washer and dryer, covered carport parking with private storage, a community pool, and an unbeatable Olde Naples location—this residence truly checks all the boxes. Whether you're looking to enjoy it as-is or update it to your own style, this is an incredible opportunity to own in one of Naples' most desirable neighborhoods. Located in The Franciscan, an intimate community of just 13 residences, this inviting townhome features a private screened lanai overlooking lush tropical landscaping and the community pool. The updated kitchen offers granite countertops, a tumbled travertine backsplash, and double ovens, while the home also features 2.5 tastefully updated bathrooms. The spacious primary suite opens to a private west-facing balcony, providing the perfect place to relax while taking in breathtaking sunset views, and the full-size in-unit washer and dryer with utility sink add everyday convenience. Additional highlights include impact-resistant windows and sliders, solid concrete construction between residences for added privacy, covered carport parking equipped with an electric vehicle charging outlet, a private storage locker, and tandem parking for an additional vehicle directly behind the carport. Recent improvements include a new roof in 2019, new parking pavers in 2020, and a freshly painted exterior completed in October 2022. With its prime location, you're just a short stroll to Historic Third Street South, world-renowned Fifth Avenue South, the sugar-white sands of the Gulf, the Naples City Dock, Cambier Park, and Crayton Cove, where you'll enjoy exceptional dining, boutique shopping, art galleries, cafés, entertainment, and the very best of the Naples lifestyle. Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this property offers the location, lifestyle, convenience, and value that buyers are looking for. One or more photos have been virtually staged, AI-generated, or rendered.

1050 6th ST S Unit 1050, Naples
$1,299,000
2 Beds ⋅ 2.5 Baths ⋅ 226021808 MLS ⋅ Naples Marina Villas BLDG.
Rare opportunity to own a fully renovated, luxurious townhome in the heart of downtown Naples at an incredible value. Ideally located in the exclusive Naples Marina Villas, this residence offers a truly walkable lifestyle just steps from the Naples Boat Club, Tin City, Fifth Avenue South, Cambier Park, waterfront dining, boutique shopping, art galleries, marinas, and everything that makes downtown Naples one of the most desirable destinations in Florida. Opportunities to enjoy this level of convenience, lifestyle, and proximity to Naples' most coveted attractions at this price point are exceptionally rare. This spacious residence features two oversized primary suites, a spacious first floor den that can be used as a dedicated workspace/office or third bedroom, floor-to-ceiling impact glass, and four private balconies, perfect for enjoying Naples' year-round sunshine. A fully renovated up and upgraded kitchen features ample soft-close cabinetry, matching GE appliances and quartz counters with a waterfall edge. A private attached two-car garage is a highly sought-after and uncommon feature in Olde Naples, along with additional private and guest parking, which provides convenience rarely found in downtown living. The pet-friendly property also includes plenty of outdoor yard space, a new washer and dryer on the first floor, new HVAC and water heater as well as a newer roof on the building. Nestled within a quiet boutique community of only six residences, this impeccably maintained home offers the perfect combination of privacy and walkability. For investors, the property boasts a strong rental history and exceptional income-producing potential, allowing for both seasonal and long-term leasing opportunities. Memberships to the marina across the street for boat slip and pool access add even more lifestyle value. Whether you're seeking a full-time residence, the perfect seasonal retreat, or an investment property with strong income history, this downtown Naples gem delivers unmatched value, location, and flexibility.

995 9th AVE S Unit 4, Naples
$10,495,000
3 Beds ⋅ 3.5 Baths ⋅ 226007847 MLS ⋅ Residences At 5th & 5th BLDG.
A truly one-of-a-kind Villa at the prestigious Residences at 5th on 5th, this exceptional villa offers approximately 5,000 square feet under air and 7,400 square feet total, perfectly positioned on iconic 5th Avenue South. Rare 5 car parking and private rooftop deck! The residence features three bedrooms plus a den, easily convertible to a fourth bedroom, and four and a half baths, delivering the scale and privacy of a single-family home with the ease of condominium living. Rich wood flooring, French doors, and private balconies create an elegant and inviting atmosphere. The chef’s kitchen is outfitted with premium appliances, a gas range, custom cabinetry, and an expansive island ideal for entertaining. A private elevator leads to the primary suite, a serene retreat with its own balcony and spa-inspired bath. Designed for extraordinary living, the home includes a rare underground entertaining room with a bar and a theater, as well as a private rooftop oasis with outdoor kitchen, jacuzzi, and sweeping sunset views. Five private parking spaces, including an attached two-car garage, add exceptional convenience. Just moments from world-class dining, nightlife, and only five blocks from the beach, this residence represents luxury living at its finest.

490 5th ST S Unit 101, Naples
$2,295,000
4 Beds ⋅ 3 Baths ⋅ 226015938 MLS ⋅ Spellbinder Villas BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. Ideally a few blocks from 3rd Street South, this updated residence offers a desirable walk-to-everything lifestyle with easy access to Naples beaches, dining and shopping. Completely renovated and move-in ready, this popular open-concept floor plan features a crisp white kitchen with stainless steel appliances, breakfast bar and a spacious center island with built-in beverage center. The primary suite includes a large walk-in shower, towel warming drawers, sleek wood vanity with storage and a generous walk-in closet. Additional upgrades include white oak flooring throughout the upper floors and hurricane impact windows and doors. Walls of sliding glass open to a private outdoor living area with pool, automated screens, built-in grill and a custom-coated aluminum awning, creating a seamless indoor-outdoor flow ideal for entertaining. The one-car garage is thoughtfully designed with pebble-coated floors, slat wall organization system, custom storage cabinetry and a new impact-rated door with lift and integrated camera. A precision-fit garage flood panel provides added protection, and a convenient outdoor foot wash is ideal after a day at the beach.

1070 5th ST S, Naples
$6,950,000
4 Beds ⋅ 4.5 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 DR, Naples
$2,295,000
3 Beds ⋅ 3 Baths ⋅ 226006477 MLS ⋅ Bella Vita BLDG.
Nestled in the heart of Olde Naples, 1008 7th St S #B-1 is a masterpiece of modern luxury and effortless elegance. This stunning residence is designed for those who crave both sophistication and comfort in one of Florida's most coveted locations. Step inside and be greeted by an open, light-filled interior, where sleek tile floors and striking quartz countertops take center stage. The chef's kitchen is a dream come true, complete with a wine cooler for entertaining and electric blinds that adjust at the touch of a button. Trey ceilings and recessed can lighting add a touch of architectural drama, while impact hurricane windows and doors provide both style and peace of mind. The master suite is your private oasis, featuring plush carpeting, a spa-like en-suite bathroom with a separate soaking tub and walk-in shower, and access to one of four inviting balconies. Imagine sipping your morning coffee or toasting a sunset from these serene outdoor retreats. An elevator whisks you effortlessly between levels, while a two-car garage with epoxy flooring ensures your vehicles are housed in style. Outside, the first-floor screened-in lanai opens directly to the community's amenities, making it easy to enjoy resort-style living at its finest. Flooded with natural light from an abundance of windows, this home is a perfect blend of luxury and livability. Don’t miss your chance to call this rare gem in Naples home!

1008 7th ST S Unit B1, Naples
$355,000
1 Beds ⋅ 1 Baths ⋅ 226003580 MLS ⋅ Park Terrace BLDG.
Park Terrace Club – Olde Naples Gem: Exceptional Location! Welcome to Park Terrace Club, one of Olde Naples’ most desirable condominium communities, showcasing classic Florida living just moments from pristine Gulf beaches, world-class dining, boutique shops, and cultural attractions. This inviting 1-bed, 1-bath condo lives large with a well-designed 712 square feet of living space — ideal for seasonal escapes or full-time Southwest Florida living. Highlight Features: • Prime Olde Naples Location: Ideally situated just minutes from the sugar-sand beaches of the Gulf of Mexico, historic 5th Avenue South, and vibrant 3rd Street South shops and restaurants. Enjoy effortless walkability to shopping, dining, theaters, parks, and community amenities. • Spacious & Functional Layout: Comfortable floor plan optimized for the Florida lifestyle, featuring bright living spaces, a generous bedroom suite, and thoughtfully planned interiors. • Kitchen features a black SMEG 50’s-style refrigerator (2025), offering a stylish blend of vintage charm and modern appeal. • Equipped with a Kinetico water filtration system (2025) in the kitchen for enhanced water quality. • Recently installed dishwasher (2025). • Impact Sliding Door & Bedroom Window: Impact-rated sliding glass door and primary bedroom window provide peace of mind, energy efficiency, and storm protection. • Second-Floor, Top-Floor Residence: Elevated positioning offers pleasant views and coastal breezes from the balcony — an ideal spot for morning coffee or evening relaxation. • Modern Systems: Building mechanicals and major systems are well maintained, including an AC system replaced approximately six years ago for year-round comfort. Community Features: • Low-Rise, Quiet Building: Boutique condominium community emphasizing privacy and relaxed coastal living. • Heated Community Pool: Inviting pool and sun deck perfect for socializing, relaxing, or unwinding after a beach day. • Elevator Access & Common Laundry Facilities (2nd Floor): Added convenience for everyday living. • Reserved Parking & Storage (3rd Floor): Assigned parking space plus a private storage locker. Lifestyle & Walkability: Live where others vacation. Stroll to the Naples Public Library, Cambier Park and tennis courts, Baker Park, the Gordon River Greenway, gourmet markets such as Wynn’s, and nearby top-tier healthcare. Approximately one block from Naples Community Hospital and just steps from the vibrant energy of downtown Olde Naples.

72 7th ST S Unit 206, Naples
$3,500,000
3 Beds ⋅ 3 Baths ⋅ 226003779 MLS
This elegant and expansive detached villa offers a rare lifestyle opportunity in the heart of Naples, just steps from the shops and restaurants of Third Street South. Built by Hemmer Construction, the residence features 3 bedrooms, 3 full baths, and two gas fireplaces as well as private elevator and 3 car garage! Additional bonus is the ability to generate income as a weekly rental! The open-plan living area is ideal for entertaining, with French doors opening to a spacious lanai. The gourmet kitchen is equipped with gas cooking, Sub-Zero and Miele appliances, and high-end finishes throughout. Flooring includes a mix of tile, hardwood, and carpet, complemented by impact-resistant doors and windows. The private primary suite occupies the third level and includes a spa-like bath with walk-in rain shower, soaking tub, Caesarstone vanity tops, and a generous walk-in closet. Juliet balconies enhance both the guest suite and main living areas, while the primary bedroom offers access to a lanai and an upper rooftop deck via a spiral staircase. Additional features include an elevator, front-door camera security system with alarm, and a private 3-car air-conditioned garage currently configured as a 2-car space with storage, pre-wired for a vehicle lift. Excellent rental potential.

340 12th AVE S Unit 6, Naples
$4,950,000
6 Beds ⋅ 4.5 Baths ⋅ 225064774 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Price significantly reduced and now priced to sell. Offering nearly 6,000 square feet of luxurious living space, this exceptional Olde Naples residence features 6 bedrooms, 4.5 bathrooms, a private den, library, and an impressive third-floor bonus room ideal for entertaining, a media room, game room, or private retreat. Designed for both everyday living and grand-scale entertaining, the gourmet kitchen is a chef's dream, appointed with Sub-Zero and Wolf appliances, dual dishwashers, and an oversized walk in pantry. A dramatic two story foyer, illuminated by an imported chandelier, welcomes you inside and leads to an elegant second floor mezzanine, complemented by a grand staircase and solid mahogany doors throughout. The private backyard oasis features a heated saltwater pool with a tranquil water feature, surrounded by lush tropical landscaping and mature trees for exceptional privacy. From the expansive third floor terrace, enjoy spectacular bird's eye views while watching the City of Naples Fourth of July fireworks, an unforgettable experience from the comfort of your own home. Perfectly positioned in the heart of Olde Naples, this fully remodeled residence is just a short walk to world-class beaches, renowned dining, boutique shopping, and boating. Additional highlights include garage ceiling height designed to accommodate a future vehicle lift, plus multiple flexible living spaces including an exercise room, family room, media room, and bonus room to suit a variety of lifestyles. This is an exceptional opportunity to own one of Olde Naples' largest and most versatile homes at an outstanding value. Combining remarkable size, luxury finishes, and an unbeatable location, this move-in-ready residence is priced to attract immediate interest. Don't miss this rare opportunity, A must see!

1160 8th ST S, Naples
$2,390,000
3 Beds ⋅ 3 Baths ⋅ 225022012 MLS ⋅ Olde Naples BLDG.
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 AVE S Unit 211, Naples
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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.