Olde Naples Homes with Two Story Style

Welcome to Olde Naples, a charming and historic neighborhood nestled in the heart of Naples, Florida. Known for its picturesque streets, lush landscaping, and proximity to the Gulf of Mexico, Olde Naples offers a unique blend of luxury and coastal living.

If you're in search of a home with two stories, Olde Naples has a variety of options to suit your needs. From traditional colonial-style residences to modern interpretations of the two-story design, you'll find a range of architectural styles to choose from in this sought-after community.

Living in Olde Naples means enjoying easy access to pristine beaches, upscale dining and shopping, and a vibrant cultural scene. Whether you prefer to spend your days lounging on the sand, exploring local art galleries, or teeing off at nearby golf courses, this neighborhood has something for everyone.

With its tree-lined avenues, historic homes, and welcoming atmosphere, Olde Naples is the perfect place to put down roots and create lasting memories. Come discover the timeless beauty and relaxed pace of life that make this community a true gem on Florida's Gulf Coast.

Newest Olde Naples Homes with Two Story Style

$389,000

1 Beds ⋅ 1 Baths ⋅ 226026571 MLS ⋅ 960 On Seventh BLDG.

The absolute very best of the Naples beach lifestyle. Where to start, first of all you are literally down the street from the beach. A short 5 minute walk or 2 minute bike ride straight to one of the best beaches in the world and the Crown Jewel of Naples. As were talking about the proximity of the beach you also down the street from Naples very own 5Th ave and next to Cambier Park that sits on 12.84 acres that include the Norris Community Center, Five Lighted Shuffleboard Courts, One Bocce Courts, Lighted Basketball Court, Arthur L. Allen Tennis Center, Bandshell, Unique Children's Playground, Softball Field, Covered Pavilion and Lots of Open Green Space to Enjoy a Picnic. Cambier Park hosts a variety of ongoing entertainment and cultural activities at the downtown bandshell and the Norris Community Center. Signature seasonal art festivals, live musical performances, and weekend concerts are held in the park. Cambier park is right next to all of Naples finest dining, shopping, art gallery's, banking and cafes on 5Th Ave. There literally is no better location in the heart of Naples than this quaint beach condo. Now you know a little about the location let me tell you about the condo, the first thing you will notice is the building has a real 90210 vibe. A Mediterranean design with an open court yard featuring fountains and palm trees with a total of only 12 units. This building must be seen to appreciate just how calm the feeling is every time you enter, filled with nesting birds, Palm trees and the sound of the fountains make it the perfect place to come home to or the ultimate getaway location to unwind. This condo has not been lived in or used as a rental it was purchased for one specific reason, to create the perfect getaway, from it all. A home away from home. With that in mind the best way to create the dream beach getaway is to start from scratch and do it your way. So with that in mind no expense was spared and a complete gut job was done, well over $125,000.00 was spent on the renovations and an additional $20,000.00 on furnishings. Its all new, new ac, tile floors, bathroom, stainless appliances, washer and dryer, new kitchen with soft close draws, Quartz counter top and the list goes on. Basically everything from the lights to the floors and everything in-between is new. And it was used on random weekends for a quick getaway, this condo is showroom ready in new condition all anyone needs to bring is their tooth brush and you're good to go. You don't even need a car you can walk or bike everywhere it's all right outside your door. There are also additional storage units in the building to store your bikes or beach chairs. With the total amount of money spent close to $150,000.00 and the attention to detail and quality materials used not to mention the location, I think you will see why this truly is the perfect little beach getaway.

960 7th ST S Unit 105, Naples

$5,990,000

4 Beds ⋅ 3 Baths ⋅ 226025317 MLS

Step into a rare piece of Naples history with this exquisitely renovated coastal cottage, once owned by legendary interior designer Albert Hadley. As co-founder of the iconic Parish-Hadley firm, Hadley designed interiors for luminaries including Jackie Kennedy and Brooke Astor—an artistic legacy that continues to resonate throughout this remarkable property. Blending historic charm with modern luxury, the thoughtfully updated main residence offers three bedrooms and two baths, with inviting spaces designed for both relaxed living and elegant entertaining. The chef’s kitchen features custom cabinetry, marble countertops, and premium finishes, while a newly designed wet bar in the dining room—complete with a Sub-Zero wine refrigerator and double beverage drawers—creates the perfect setting for hosting guests. The first-floor bath has been beautifully reimagined with Kohler fixtures, and the second-floor bath offers the same level of refined sophistication. Designed to embrace Naples’ indoor-outdoor lifestyle, the screened porch serves as an extension of the living space, complete with a SunBrite outdoor television and custom furnishings. Overlooking the sun-drenched pool and patio, the space is framed by lush tropical landscaping and desirable southern exposure. A private guest cottage provides exceptional flexibility for family and visitors, featuring a bespoke kitchenette, built-in queen bed with storage, separate bunk room, and a fully remodeled bath. Recent upgrades include a new roof, updated HVAC system, tankless water heater, outdoor shower, complete dormer replacement, extensive subfloor and tile renovations, and a whole-house water filtration system. Timeless architectural details abound, including custom wool rugs, plantation shutters, crown molding, and French doors. A charming white picket fence, alley access, garage, and covered carport enhance both curb appeal and convenience. Ideally located just three blocks from Naples' pristine beaches and a short stroll from the renowned dining, shopping, and entertainment of Third Street South and Fifth Avenue South, this property offers an unparalleled Old Naples lifestyle. Whether enjoyed as a full-time residence or a luxury retreat accommodating 14+ guests, this is a truly rare opportunity to own a distinctive piece of Naples history.

356 11th AVE S, Naples

$22,995,000

6 Beds ⋅ 6.5 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 AVE S, Naples

$4,995,000

3 Beds ⋅ 3.5 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 ST S, Naples

$6,495,000

5 Beds ⋅ 4.5 Baths ⋅ 226020603 MLS

Ideally situated in the heart of downtown Naples, this completely remastered single-family residence embodies the essence of refined Florida living. Thoughtfully designed with elevated finishes throughout, the home welcomes you through a dramatic two-story foyer highlighted by soaring ceilings, architectural millwork, and a striking staircase that sets the tone for the interiors beyond. The flowing floor plan is both spacious and inviting, centered around a beautifully appointed kitchen featuring an oversized island and seamless connection to the dining and living areas — ideal for both everyday living and effortless entertaining. Pocketing impact glass doors open to the covered lanai with a summer kitchen, extending the living space outdoors to a generous lawn perfectly suited for gatherings, pets, and family enjoyment. The first-floor primary suite offers a private retreat, accompanied by a dedicated office, while guests are comfortably accommodated with their own upstairs living area and three ensuite bedrooms. Just moments from the charm of Olde Naples, residents can spend evenings strolling to renowned dining, shopping, and the nearby beaches, enjoying the convenience of downtown living right outside their door.

950 8th ST S, Naples

$625,000

1 Beds ⋅ 1 Baths ⋅ 2026017700 MLS ⋅ Kensington Gardens BLDG.

Location, location, location in the heart of Olde Naples! Welcome to Kensington Gardens, a charming vacation rental community just one block from world-famous Fifth Avenue South and only a short stroll to the white sandy beaches of the Gulf of Mexico. This beautifully updated 1-bedroom, 1-bath condominium offers the perfect Naples retreat with a bright coastal feel, tasteful furnishings, ceramic tile throughout, and in-residence laundry for added convenience. Situated in one of Naples’ most walkable and desirable downtown locations, guests can enjoy easy access to upscale dining, boutique shopping, art galleries, live entertainment, cafés, and local favorites throughout Fifth Avenue South and nearby Third Street South. Kensington Gardens offers classic Olde Naples charm with a relaxed atmosphere, making it ideal as a seasonal getaway, investment property, or personal vacation escape. Owner has a recent inspection report available. Property is being sold AS IS, and reasonable offers will be considered.

480 5th ST S Unit 202, Naples

$5,195,000

4 Beds ⋅ 4.5 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 AVE S, Naples

$494,000

1 Beds ⋅ 1 Baths ⋅ 226019237 MLS ⋅ Garden Court BLDG.

Steps from the beach and all of Naples’ finest dining! This beautiful, turnkey furnished condo offers an unbeatable location - 2.5 blocks to prestigious Fifth Avenue and the beach, and 4 blocks to the charming boutiques and restaurants on Third Street South! This unit is filled with natural light and set within an intimate boutique community. Unit had NO WATER DAMAGE during any of the last hurricanes/storms. It also features new impact-resistant windows, a newer A/C and water heater, an updated kitchen and bath, and easy-to-maintain tile flooring throughout. Tastefully furnished and decorated in a coastal contemporary theme, complete with a sleeper sofa ideal for additional guests or family. Enjoy your private southern-facing patio which overlooks a peaceful garden courtyard. The community offers common laundry, extra storage, bike racks, and recent updates include new exterior paint, gutters, soffits, pavers, irrigation, and landscaping.

275 8th AVE S Unit 275, Naples

$27,900,000

6 Beds ⋅ 5.5 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

$8,350,000

5 Beds ⋅ 5.5 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 ST S, Naples

$1,295,000

2 Beds ⋅ 2 Baths ⋅ 226017659 MLS ⋅ Manor Apts BLDG.

Ideally located just steps from the Gulf of Mexico, this condominium building sits in the coveted X-500 Flood Zone and has never experienced storm water intrusion. Set in a high-and-dry location within walking distance of upscale boutiques and world-class restaurants, this artfully redesigned residence epitomizes the Old Naples lifestyle. Meticulously transformed from its original mid-century design, the home now features a clean-lined, contemporary aesthetic. Highlights include impact-rated windows and doors, polished porcelain flooring throughout, floating bathroom vanities, 1¾” solid core interior doors, and two fully outfitted walk-in closets. Thoughtful, unexpected touches include a double glass-door entry to the primary suite, a striking 60-inch white glass fireplace, and a chef’s kitchen with custom cabinetry, mitered quartz countertops, and full Calacatta Extra marble slab backsplashes featuring dramatic, organic veining. Top-tier appliances complete the kitchen: a Liebherr refrigerator, 23-bottle under-counter wine cooler, Bosch induction range, microwave drawer, and Bosch washer, dryer, and dishwasher. A seamless transition from the main living area leads to the screened outdoor lanai, perched above the property’s stone waterfall and private landscaped courtyard—perfect for year-round enjoyment. Truly a contemporary masterpiece for the most discerning buyer

231 3rd AVE S Unit 231, Naples

$6,495,000

4 Beds ⋅ 5.5 Baths ⋅ 226017050 MLS

Discover an exquisite retreat in the heart of Olde Naples, just 2.5 blocks from 3rd Street South, featuring some of Naples’ most desirable shopping and dining experiences. Enjoy the sugar-white sands of the Gulf just moments away. This impeccably designed residence embodies refined coastal elegance, offering four lavish bedroom suites—each with a private ensuite bath and spacious walk-in closet—alongside a private study, stylish powder room and dedicated pool bath. Every detail has been thoughtfully curated, from the oversized four-car garage to the seamless indoor-outdoor living experience. An expansive covered lanai, complete with a fully appointed outdoor kitchen, frames the sparkling pool and creates a captivating setting for sunset dinners and sophisticated entertaining. A rare blend of luxury, comfort, and prime location—this is Naples living at its finest.

545 13th AVE S, 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.