Olde Naples

Infused with nature at every step, creating an atmosphere reminiscent of romantic European villages.

Welcome to Olde Naples

Feel the weight of the world fall away in this serenely upscale historic jewel where chic commercial offerings and diverse architecture await.
Graced with tree-lined streets and ethereal architecture steeped in nostalgia, the picturesque neighborhood is known as Olde Naples has long been a paragon of elegance. From the salt-scented breezes carried in from the beach to the tropical foliage lining boutique shops, Olde Naples is infused with nature at every step, creating an atmosphere reminiscent of romantic European villages. 
It’s in Olde Naples that visitors will encounter the historic Naples Pier, as well as some of the city’s oldest historic homes, which date back to the late 19th-century. Inviting and upbeat, Olde Naples is well-regarded among all and melds its prosperous vitality with an irresistible warmth. Many come to Olde Naples for its fine shopping and dining, which is spread across idyllic commercial corridors steeped in history. 
The residential real estate of Olde Naples is as diverse as it is beautiful, consisting of historic beach cottages and sweeping mansion estates, single-family homes, and gorgeous Mediterranean villas. Though potential homeowners typically look to Olde Naples for its staggering grandeur, the neighborhood also contains plenty of smaller single-family beauties just as opulent as the larger estates.

What to Love

  • Rich history and flush with captivating architecture
  • Breathtaking scenery year-round and awe-inspiring sunsets
  • Laid-back coastal vibes in a refined setting

Local Lifestyle

As an upscale neighborhood for the wealthy, Olde Naples is replete with high-end shopping, award-winning cuisine, and pristinely maintained amenities. Strict beachfront zoning keeps the waterfront limited to single-family homes, adding to the small-town, coastal charm. Residents will find there’s never a dull moment and are able to explore a wide range of engaging activities year-round.

Dining, Entertainment, & Shopping

The commercial districts of 5th Avenue South and Third Street South epitomize Olde Naples’ seamless marriage between historic grace and contemporary trends. Here, visitors can encounter everything from upscale fashion boutiques and art galleries to health and wellness shops and artisan creations tucked away in picturesque alcoves among the courtyards and swaying palms. Additionally, the Third Street Farmers Market stands as one of the community’s favorite activities, and locals love browsing the fresh florals, decadent homemade foods, crafts, and organic produce available. 
Perfectly in tune with the colorful historic cottages and beach homes, both 5th Avenue South and Third Street South are overflowing with award-winning eateries certain to impress any culinary connoisseur. Campiello Ristorante & Bar has won multiple accolades for their delicious Italian cuisine, which comes served in a romantic little historic venue with wrought-iron balconies draped in verdant ivy. 
Regarded as one of the best new restaurants in all of South Florida, D'Amico's Continental is a steakhouse taking its inspiration from the glamor of Paris that’s well known for its creative cocktails. The Inn on Fifth is one of Naples’ premier 4-star hotels and houses not one, but two top-tier restaurants.
Ocean Prime is the top fine dining destination for business meetings and special affairs, while Truluck’s is best known for their nightly live piano bar. Both restaurants specialize in succulent steak and seafood dishes, which go well with the undeniably sophisticated atmosphere.

Things to Do

The genteel and artistic spirit of the Olde Naples community is thriving, evidenced in the array of cultural institutions and special celebrations. Each year, the Taste of Collier Tour enchants visitors with a heavenly assortment of the city’s finest dishes from its best restaurants, along with engaging live entertainment and an ice sculpting competition. The annual Naples Downtown Art Show is a two-day event showcasing the works of creators from across the country across a variety of different mediums.
Fifth Avenue South comes to life with rare, exotic, and vintage muscle cars during the annual Cars on 5th Concours, the city’s largest one–day event. Tickets come in a range of options, including VIP passes complete with drinks, catering, and access to the most exotic cars of the show. Those looking to get in tune with nature will want to venture to the Naples Botanical Garden, which has cultivated the natural splendor of Florida’s tropical flora into a dreamy 170-acre paradise. Others might decide to spend the evening enjoying a performance by The Naples Players at Sugden Community Theater, the city’s favorite place for low-key plays and musical theater.


Olde Naples is home to a number of excellent schools. Top educational opportunities include:
  • Community School of Naples, PK & K-12, highly rated private school ranked #23 in the state
  • Seacrest Country Day School, PK & K-12, highly rated private school among the best in the state
  • First Baptist Academy, PK & K-12, highly rated private Baptist school among the top in Collier County
  • Mason Classical Academy, K-12, highly rated public school among the top in Collier County
  • Lake Park Elementary School, PK & K-5, highly rated public school ranked #3 in Collier County
  • Gulf View Middle School, 6-8, highly rated public school ranked #2 in Collier County
  • Naples High School, 9-12, highly rated public high school ranked #3 in Collier County
  • Saint Ann Catholic School, PK & K-8, highly rated private Catholic elementary school

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Work With Charles

Charles specializes in luxury residential properties throughout Naples’ most exclusive and sought after communities. Multi-million dollar producer and multiple award winner. Whether you are looking for a new home or thinking about selling your current home, call me today.

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