Olde Naples
Olde Naples is where historic charm meets modern luxury. This iconic neighborhood continues to captivate with its tree-lined streets, Mediterranean-inspired homes, and walkable lifestyle. Just steps from the Gulf’s pristine beaches and the vibrant 5th Avenue, residents enjoy easy access to world-class dining, boutique shopping, and art galleries.
Olde Naples is more than a location—it’s a community. With a focus on preservation and sustainability, this area offers a blend of rich history, culture, and contemporary conveniences. Whether you’re looking for a luxury estate or a cozy retreat, Olde Naples is one of the most sought-after places to live in Southwest Florida.
An elegant and historic community filled with rich culture and stunning architecture.
Situated in the heart of the city, Olde Naples is a charming neighborhood that perfectly blends historic charm with modern sophistication. Known for its walkable streets, elegant mansions, and historic beach cottages, this community offers a lifestyle that combines tradition with luxury.
What to Love
- Charming single-family homes
- Family-friendly atmosphere
- Unmatched beach access
- Endless dining and shopping options
Local Lifestyle
Residents of Olde Naples enjoy a relaxed yet upscale lifestyle. With homes priced between $2 million and $5 million, the community is home to some of Florida’s wealthiest individuals. The tranquil setting is ideal for early morning tennis matches or leisurely walks along the tree-lined streets.
Dining, Entertainment & Shopping
The culinary scene in Olde Naples is just as rich as its history. Jane’s Garden Café is the go-to spot for breakfast and lunch, offering dishes like the crab and shrimp scrambler and challah French toast.
For dinner, Sails Restaurant is a favorite, known for its lobster ravioli and Wagyu tenderloin.
The Dock at Crayton Cove offers upscale dining with breathtaking waterfront views.
Shopping on Fifth Avenue South is a must, featuring boutiques, national retailers, and fine dining all in one picturesque location.
Things to Do
There’s always something to explore in Olde Naples. Whether it’s attending the annual Paradise Coast Wine & Food Experience or enjoying a quiet day at Cambier Park, the community offers a variety of events and activities.
Schools
Families in Olde Naples value quality education, with highly-rated schools such as:
- Gulfview Middle School (6-8)
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Listing Courtesy of:
Gulf Coast International Prop
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Listing Courtesy of:
William Raveis Real Estate
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Listing Courtesy of:
William Raveis Real Estate
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Listing Courtesy of:
William Raveis Real Estate
(48)
Listing Courtesy of:
Gulf Coast International Prop
(40)
Listing Courtesy of:
Gulf Coast International Prop
Virtual Tour
(37)
Listing Courtesy of:
Premier Sotheby's Int'l Realty
(47)
Listing Courtesy of:
John R Wood Properties
(4)
Listing Courtesy of:
London Bay Realty Inc.
Virtual Tour
(50)
Listing Courtesy of:
Gulf Coast International Prop
Virtual Tour
(44)
Listing Courtesy of:
Gulf Coast International Prop
Virtual Tour
(50)
Listing Courtesy of:
William Raveis Real Estate
Listing No. 226009175
Listing Courtesy of:
Gulf Coast International Prop
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1857 Galleon DR NAPLES, FL 34102
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$59,995,000
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Beds 6 Baths 7 | 3 Sqft 13,004 Property Type House
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(14)
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Listing No. 226005171
Listing Courtesy of:
William Raveis Real Estate
Listing No. 226008320
Listing Courtesy of:
William Raveis Real Estate
Listing No. 226003751
Listing Courtesy of:
William Raveis Real Estate
Listing No. 226019200
Listing Courtesy of:
Gulf Coast International Prop
Listing No. 225002679
Listing Courtesy of:
Gulf Coast International Prop
Listing No. 226003650
Listing Courtesy of:
Premier Sotheby's Int'l Realty
Listing No. 226016944
Listing Courtesy of:
John R Wood Properties
Listing No. 226003576
Listing Courtesy of:
London Bay Realty Inc.
Listing No. 226010821
Listing Courtesy of:
Gulf Coast International Prop
Listing No. 226016469
Listing Courtesy of:
Gulf Coast International Prop
Listing No. 226015887
Listing Courtesy of:
William Raveis Real Estate
(12)
$271,000,000
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22,800 Sqft 22,800 Sqft
226009175 Listing No. 226009175
House Property Type: House
(12)
Listing Courtesy of: Gulf Coast International Prop
(14)
$59,995,000
6 6 Beds
7 | 3 7 | 3 Baths
13,004 Sqft 13,004 Sqft
226005171 Listing No. 226005171
House Property Type: House
(14)
Listing Courtesy of: William Raveis Real Estate
(25)
$41,500,000
6 6 Beds
7 | 2 7 | 2 Baths
9,227 Sqft 9,227 Sqft
226008320 Listing No. 226008320
House Property Type: House
(25)
Listing Courtesy of: William Raveis Real Estate
(50)
$39,995,000
6 6 Beds
6 | 2 6 | 2 Baths
9,074 Sqft 9,074 Sqft
226003751 Listing No. 226003751
House Property Type: House
(50)
Listing Courtesy of: William Raveis Real Estate
(48)
$39,750,000
5 5 Beds
6 | 1 6 | 1 Baths
8,544 Sqft 8,544 Sqft
226019200 Listing No. 226019200
House Property Type: House
(48)
Listing Courtesy of: Gulf Coast International Prop
(40)
$39,000,000
5 5 Beds
4 | 2 4 | 2 Baths
5,277 Sqft 5,277 Sqft
225002679 Listing No. 225002679
House Property Type: House
(40)
Listing Courtesy of: Gulf Coast International Prop
VIRTUAL TOUR
(37)
$38,500,000
6 6 Beds
7 | 1 7 | 1 Baths
11,346 Sqft 11,346 Sqft
226003650 Listing No. 226003650
House Property Type: House
VIRTUAL TOUR
(37)
Listing Courtesy of: Premier Sotheby's Int'l Realty
(47)
$36,500,000
5 5 Beds
5 | 2 5 | 2 Baths
6,883 Sqft 6,883 Sqft
226016944 Listing No. 226016944
House Property Type: House
(47)
Listing Courtesy of: John R Wood Properties
(4)
$36,000,000
5 5 Beds
5 | 4 5 | 4 Baths
9,059 Sqft 9,059 Sqft
226003576 Listing No. 226003576
House Property Type: House
(4)
Listing Courtesy of: London Bay Realty Inc.
VIRTUAL TOUR
(50)
$33,500,000
5 5 Beds
5 | 3 5 | 3 Baths
14,000 Sqft 14,000 Sqft
226010821 Listing No. 226010821
House Property Type: House
VIRTUAL TOUR
(50)
Listing Courtesy of: Gulf Coast International Prop
VIRTUAL TOUR
(44)
$32,500,000
6 6 Beds
6 | 2 6 | 2 Baths
6,085 Sqft 6,085 Sqft
226016469 Listing No. 226016469
House Property Type: House
VIRTUAL TOUR
(44)
Listing Courtesy of: Gulf Coast International Prop
VIRTUAL TOUR
(50)
$31,900,000
5 5 Beds
6 | 1 6 | 1 Baths
8,753 Sqft 8,753 Sqft
226015887 Listing No. 226015887
House Property Type: House
VIRTUAL TOUR
(50)
Listing Courtesy of: William Raveis Real Estate
The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations. Copyright 2026 Southwest Florida MLS organizations. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.