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Oyster Bay Naples Florida Homes for Sale

Naples Florida Real Estate

Oyster Bay Naples Real Estate

Homes For Sale1$4.4M
Condos For Sale21$410K - $4M
Sold ( Past 6 Months )6$379K - $13M
Last updated at 6:57am 12/05/2025

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$4,400,000
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Oyster Bay NEW

1550 Chesapeake Ave, Naples, FL 34102

Homes - 2,555 ft² / 3,443 ft² - 3 Car Garage

4 Bed / 4 Baths / Pool

Built 1991
Oyster Bay Naples Homes for Sale: Experience waterfront living in this stunning four-bedroom ranch-style residence offering direct, deep-water Gulf access and exceptional privacy. Positioned with desirable southern exposure, the home captures tranquil views of lush mangroves and picturesque boat docks, creating a serene Naples backdrop. A highlight of the property is the expansive 1,000-square-foot private dock, ideal for boating enthusiasts, sunset lounging or hosting unforgettable gatherings by the water. Inside, the home features a gourmet kitchen designed to impress, complete with a 9-foot island, premium finishes, and seamless flow for everyday living or entertaining. The elegant dining room includes an integrated built-in bar, offering a sophisticated space for hosting friends and family. Additional features include a three-car garage, spacious bedrooms, and an inviting single-level layout that embodies comfort and coastal ease. Just minutes from 5th Avenue’s renowned shops and fine dining, this home offers the ideal blend of luxury, convenience and waterfront charm. A must-see for those seeking exceptional Naples living.



$12,995,000
Sold Price:
$11,450,000
Sold Date:
09/17/2025
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Oyster Bay

1340 Jewel Box Ave, Naples, FL 34102

Homes - 5,619 ft² / 7,793 ft² - 3 Car Garage - 4 Carport

4+Den / 5 Baths / 1 Half / Pool / Spa

Built 2018
Oyster Bay Naples Homes: Offering spectacular waterfront living at it's finest is this crowning jewel of Jewel Box Avenue. Residing at the point of Chesapeake canal and Naples Bay stands this 4 bedroom en-suite estate with panoramic west facing water views from nearly every room. Owners will enjoy the first floor primary en-suite with 2 large walk in closets, huge primary bath with separate shower and soaking tub. Steps from the primary bed is a cozy outdoor sitting area with electric (remote controlled) retractable screens and shutters to enjoy the amazing sunsets over the bay. Guest will enjoy the second floor privacy with elevator access. Each en-suite has its own wrap around balcony access with spacious lounge areas and west facing water views. Additionally the second floor offers multiple en-suite wet bars, sitting area and media room that could easily be used as a 5th bedroom. Perhaps the star of the show is the nearly 8000 sq-ft of outdoor living space with waterfront infinity edge pool, 2 spas, outdoor kitchen, pool bath and multiple docks and boat lifts. Boaters will appreciate this section of Naples Bay is a no wake zone and the home resides well away from the channel marked area thus offering peace and quiet calm waters. Additionally the boat lifts have been strategically installed on the north canal side of the property offering further protection. The area has recently undergone extensive dredging and this property can dock larger vessels with a 24,000 lbs boat lift and 13,000 lbs jet ski/kayak platform lift. The list of upgrades to this home are extensive with a recent 7 figure renovation and refurnishing which WAS NOT a result of flooding or any storm damage. If you are looking for a well built turnkey waterfront property that lives like a high end resort 1340 Jewel Box should be considered.




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Need professional assistance selling your property at Oyster Bay Naples? Find out how an Area Specialist can help to generate more property exposure in order to get the most money for your investment in the least amount of time.Contact Us.
*Just Listed: new properties that came on the market within the last 30 days.
*Decrease/Increase: listing values that are being recorded within the last 30 days.
*Foreclosures/Short Sale: Please note, all properties are subject to bank approval. Buyers must be pre-approved or show proof of funds before submitting an offer.

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