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Oyster Bay Real Estate Sold55+ Active Adult

Oyster Bay contains (25) subdivisions

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Oyster Bay, 1460 Jewel Box Ave, Naples, Florida 34102, image 1
Sold - Dec 12, 2025
$3,800,000 $500K
  • 3 Beds
  • 31/2 Baths
  • 3,192 SqFt
  • $1,190/SqFt
House sold in Oyster Bay
1460 Jewel Box Ave, Naples, FL 34102
Waterfront luxury on jewel box avenue located in oyster bay. The only street in naples that is dual waterfront lots! Waterfront access on both front and back sides of the property, with two 65 foot private docks , this property is a boater’s dream, providing easy access to the gulf. Welcome to your private slice of paradise in the heart of naples. Under 5 minutes from the 5th avenue, shopping and dining, and 7 minutes to the beach. This beautiful custom waterfront residence on sought-after jewel box avenue offers the ultimate florida lifestyle with exceptional indoor-outdoor living. Custom built to the highest standards by bcbe . The one of a kind architecture and landscaping provide a truly custom home. Designed for both relaxation and entertaining, the home features a sparkling pool, spa, and a front outdoor courtyard that sets the tone for resort-style living. The split bedrooms all en-suite , allow for maximum privacy. Enjoy evenings by the fully equipped outdoor kitchen while taking in tranquil water views. Inside you have a walk-in climate controlled wine cellar, wolf/subzero and miele appliances, a drop down 109" screen and hd projector, and so much more. Inside, you’ll find spacious living areas filled with natural light and elegant finishes that complement the home’s open design. The thoughtful layout balances privacy and flow, making it perfect for everyday living as well as hosting family and friends. From morning coffee by the water to sunset cruises just steps from your back door, this home captures the very best of naples living.
Oyster Bay, 1340 Jewel Box Ave, Naples, Florida 34102, image 1
Sold - Sep 17, 2025
$11,450,000 $2M
  • 4 Beds
  • 51/2 Baths
  • 5,619 SqFt
  • $2,038/SqFt
House sold in Oyster Bay
1340 Jewel Box Ave, Naples, FL 34102
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.
Club At Blue Point At Oyster Bay, 1495 Blue Point Ave #C, Naples, Florida 34102, image 1
Pending
$724,900
  • 2 Beds
  • 21/2 Baths
  • 1,529 SqFt
  • $474/SqFt
Condo for sale in Club At Blue Point At Oyster Bay
1495 Blue Point Ave #C, Naples, FL 34102
Gorgeous waterfront condo just a bike ride from downtown naples, white sandy beaches and naples fine dining and shopping. Located in royal harbor a fabulous waterfront and boating community, this awesome condo features a tropical outdoor space with firepit and walkway leading to your brand new boat lift that can accommodate up to a 28 foot boat allowing for easy access to the gulf of mexico. Open floor plan with beautifully remodeled kitchen including granite countertops, wood cabinets, circular breakfast bar with window seating & tile throughout. This two story townhouse includes a master suite located upstairs and a private balcony. Also offering a guest en-suite bedroom, a first floor office/den, and a one car air-conditioned attached garage surrounded by lush landscaping giving you complete privacy and making it your own tropical retreat. Relax on either your brick-layered patio with firepit or enclosed screened-in lanai. This tropical oasis is truly a must see! Condo allows 12 monthly leases per year !! As of 2/15/2024 this is by far the lowest price per sq ft in royal harbor/ oyster bay !!!
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Royal Port At Oyster Bay, 1145 Cherrystone Ct #C, Naples, Florida 34102, image 1
Pending
$539,000
  • 2 Beds
  • 2 Baths
  • 982 SqFt
  • $549/SqFt
Condo for sale in Royal Port At Oyster Bay
1145 Cherrystone Ct #C, Naples, FL 34102
Now accepting back up offers!! Waterfront location with direct gulf access! Comes with your own boat dock updated 2 bedroom, 2 bathroom, with 2 parking spaces second floor, corner unit condo with private screened balcony is located in oyster bay. Other features include open bright kitchen design with beautiful granite countertops, built-in wine cooler, large master bedroom en suite with walk-in closet and laundry room. No flood damage in building. The lanai overlooks a protected canal and the included boat-dock. Minutes to the naples sugary white sandy beaches and the heart of downtown!
Oyster Bay, 1490 Jewel Box Ave, Naples, Florida 34102, image 1
Pending
$6,499,000
  • 4 Beds
  • 31/2 Baths
  • 3,996 SqFt
  • $1,626/SqFt
House for sale in Oyster Bay
1490 Jewel Box Ave, Naples, FL 34102
Exquisite four-bedroom plus den home located in desirable oyster bay on jewelbox ave. One of the only streets offering water on both sides of the street. Upon entering this open floor plan, you'll be greeted by soaring ceilings, and an abundance of windows offering natural light. The second floor features multiple balconies with beautiful water views. This property has undergone a complete transformation, featuring new floors, baseboards, drywall, and a new resort-style pool/spa with new pebble-tech and tile, top-of-the-line equipment and heater. The home includes a chef's dream kitchen equipped with a wolf/subzero appliance package. The outdoor space boasts multiple entertaining areas, including a newly updated fire pit. Boasting three boat docks, including two boat lifts and a jet ski lift, all with new motors by garland & garland, this property is a boater's and fisherman's paradise, complete with a newer seawall. With direct bridge access to the gulf of mexico, this centrally located property is just minutes away from downtown naples, providing the perfect blend of luxury and convenience.
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Subdivision Amenities

Bike Storage
Car Wash Area
Common Laundry
Community Boat Dock
Community Boat Slip
Community Gulf Boat Access
Fish Cleaning Station
Fishing Pier
Guest Room
Internet Access
Pool
See Remarks
Sidewalk
Storage
Streetlight
Tennis Court(s)
Underground Utility
Barbecue
Bike Storage
Clubhouse
Common Laundry
Community Boat Dock
Internet Access
None
Pool
Storage

Scores

Walk Score®

Car-Dependent. Most errands require a car.

33

100

Transit Score®

No data.

N/A

Bike Score®

Somewhat Bikeable. Minimal bike infrastructure.

41

100

Sound Score®

Bearable noise.

79

100

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