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A rare waterfront offering in Oyster Bay, 1420 Jewel Box Avenue captures the best of Naples living. With 160 feet of water frontage across two sides of the property, two private docks, two boat lifts, and bridge-free access to Naples Bay and Gordon Pass, this is an exceptional setting for those who want to spend their days on the water. Southern exposure brings natural light into the home and sets the stage for sweeping water views, sunrises, and sunsets. Inside, updated interiors and open living spaces offer an inviting setting for entertaining or a quiet retreat after a day on the boat. Meticulously maintained, the home is equally suited to year-round living, a seasonal escape, or the opportunity to create a new waterfront residence. Just minutes from downtown Naples, acclaimed dining, shopping, and the Gulf beaches, this distinctive property pairs a coveted boating location with remarkable possibilities.

3 Beds ⋅ 3 Baths ⋅ 226034349 MLS

A rare waterfront offering in Oyster Bay, 1420 Jewel Box Avenue captures the best of Naples living. With 160 feet of water frontage across two sides of the property, two private docks, two boat lifts, and bridge-free access to Naples Bay and Gordon Pass, this is an exceptional setting for those who want to spend their days on the water. Southern exposure brings natural light into the home and sets the stage for sweeping water views, sunrises, and sunsets. Inside, updated interiors and open living spaces offer an inviting setting for entertaining or a quiet retreat after a day on the boat. Meticulously maintained, the home is equally suited to year-round living, a seasonal escape, or the opportunity to create a new waterfront residence. Just minutes from downtown Naples, acclaimed dining, shopping, and the Gulf beaches, this distinctive property pairs a coveted boating location with remarkable possibilities.

1420 Jewel Box Avenue, Naples

$7,995,000

Experience the ultimate in Naples living with this new contemporary water view home, minutes from Fifth Avenue South, with a deeded boat slip, oversized four-car garage and generous storage. Offered fully furnished with a curated art package and a golf cart included — arrive with a suitcase. Completed in 2026 and never lived in, this three-story residence offers approximately 4,400 square feet of elevated living area — five bedrooms, five full baths, a powder room, and a private elevator serving every floor. The primary suite sits on the main living floor, with three guest suites and a loft club room above: a home that lives easily for two, with room for a few guests or a full house. A dramatic three-story glass entry opens to an open-concept living floor with soaring ceilings, contemporary custom built-ins, and walls of glass framing expansive western views over the water and stunning sunsets. The chef’s eat-in kitchen is replete with an oversized island, custom cabinetry, walk-in pantry, and high-end appliances including a professional gas range, plus a wet bar built for entertaining. An east–west sightline carries that light through the house to the outdoor living room, where a built-in kitchen, fireplace and relaxed seating overlook the elevated heated pool and spa. Mature tropical landscaping and privacy screening make it entirely private, and the elevated terrace stays usable year-round. The primary suite is a quiet sanctuary with a spa-inspired bath and dual walk-in closets with custom built-ins. The fifth bedroom is presently appointed as a private office, an elegant work-from-home retreat that reverts to a guest suite whenever needed. Upstairs, three spacious guest suites surround a loft-style club room with wet bar, ideal for morning coffee or an evening cocktail. The lower level adds approximately 1,600 square feet of finished, fully conditioned storage with direct interior access, alongside a climate-controlled four-car garage. A reinforced perimeter wall surrounds the property, with an integrated flood panel system and backup power for genuine peace of mind. The deeded boat slip sits just out the front door, with a private lift, a City-maintained seawall and no-bridge access to Naples Bay and the Gulf. No canal turns, no clearance math, no bridge waits. An ideal lifestyle location close to Fifth Avenue South and Third Street South, renowned worldwide for fine dining, galleries and shopping. The Bayshore Arts District, the Naples Pickleball Center and the Gulf beaches are all close at hand, with Naples and Fort Myers airports an easy drive. New, elevated, west-facing, downtown-adjacent, and boat-ready on day one.

5 Beds ⋅ 6 Baths ⋅ 226032953 MLS

Experience the ultimate in Naples living with this new contemporary water view home, minutes from Fifth Avenue South, with a deeded boat slip, oversized four-car garage and generous storage. Offered fully furnished with a curated art package and a golf cart included — arrive with a suitcase. Completed in 2026 and never lived in, this three-story residence offers approximately 4,400 square feet of elevated living area — five bedrooms, five full baths, a powder room, and a private elevator serving every floor. The primary suite sits on the main living floor, with three guest suites and a loft club room above: a home that lives easily for two, with room for a few guests or a full house. A dramatic three-story glass entry opens to an open-concept living floor with soaring ceilings, contemporary custom built-ins, and walls of glass framing expansive western views over the water and stunning sunsets. The chef’s eat-in kitchen is replete with an oversized island, custom cabinetry, walk-in pantry, and high-end appliances including a professional gas range, plus a wet bar built for entertaining. An east–west sightline carries that light through the house to the outdoor living room, where a built-in kitchen, fireplace and relaxed seating overlook the elevated heated pool and spa. Mature tropical landscaping and privacy screening make it entirely private, and the elevated terrace stays usable year-round. The primary suite is a quiet sanctuary with a spa-inspired bath and dual walk-in closets with custom built-ins. The fifth bedroom is presently appointed as a private office, an elegant work-from-home retreat that reverts to a guest suite whenever needed. Upstairs, three spacious guest suites surround a loft-style club room with wet bar, ideal for morning coffee or an evening cocktail. The lower level adds approximately 1,600 square feet of finished, fully conditioned storage with direct interior access, alongside a climate-controlled four-car garage. A reinforced perimeter wall surrounds the property, with an integrated flood panel system and backup power for genuine peace of mind. The deeded boat slip sits just out the front door, with a private lift, a City-maintained seawall and no-bridge access to Naples Bay and the Gulf. No canal turns, no clearance math, no bridge waits. An ideal lifestyle location close to Fifth Avenue South and Third Street South, renowned worldwide for fine dining, galleries and shopping. The Bayshore Arts District, the Naples Pickleball Center and the Gulf beaches are all close at hand, with Naples and Fort Myers airports an easy drive. New, elevated, west-facing, downtown-adjacent, and boat-ready on day one.

1085 SANDPIPER Street, Naples

$3,899,000

No bridges between the dock and the Gulf. This Oyster Bay home sits on a canal 121 to 150 feet wide with direct access to Naples Bay and Gordon Pass. Private Ipe dock with boat lift, water and power at the dock. Southern rear exposure over the screened, heated pool and spa and a covered outdoor dining area. Concrete block construction with vinyl siding, metal roof, electric and manual shutters. 3,062 square feet on one level: 3 bedrooms plus a den, 3.5 baths. Original 2002 build, not remodeled, with a new water heater and central air conditioning replaced in 2019. Lighthouse-inspired architecture, vaulted ceilings, custom millwork, decorative painted details and good natural light. Split-bedroom plan: the primary suite and one guest bedroom open to the pool; the second guest bedroom and the den each have a covered outdoor sitting area. The den works as a home office. Attached two-car garage, 24 by 24 with a 12-foot ceiling, its own mini-split air conditioning and an oversized closet for tackle and boating gear. Circular paver driveway. Lot 80 by 140. Close to Tin City, Bayfront and Fifth Avenue South. Floor plan and 3D tour attached.

3 Beds ⋅ 4 Baths ⋅ 226013587 MLS

No bridges between the dock and the Gulf. This Oyster Bay home sits on a canal 121 to 150 feet wide with direct access to Naples Bay and Gordon Pass. Private Ipe dock with boat lift, water and power at the dock. Southern rear exposure over the screened, heated pool and spa and a covered outdoor dining area. Concrete block construction with vinyl siding, metal roof, electric and manual shutters. 3,062 square feet on one level: 3 bedrooms plus a den, 3.5 baths. Original 2002 build, not remodeled, with a new water heater and central air conditioning replaced in 2019. Lighthouse-inspired architecture, vaulted ceilings, custom millwork, decorative painted details and good natural light. Split-bedroom plan: the primary suite and one guest bedroom open to the pool; the second guest bedroom and the den each have a covered outdoor sitting area. The den works as a home office. Attached two-car garage, 24 by 24 with a 12-foot ceiling, its own mini-split air conditioning and an oversized closet for tackle and boating gear. Circular paver driveway. Lot 80 by 140. Close to Tin City, Bayfront and Fifth Avenue South. Floor plan and 3D tour attached.

1510 Chesapeake Avenue, Naples

1390 Chesapeake Avenue Unit 1390, Naples

$1,499,000

Completely renovated 3 bedroom, 2 bath, TURNKEY furnished BY ARHAUS, waterfront condo on Naples Bay with Direct Gulf access & 26 ft Boat Slip, NEW ROOF JULY 2026. The interior has been COMPLETELY RENOVATED and NEVER LIVED-IN with luxury finishes and elegant Arhaus furnishings throughout creating a stylish and functional living space including impact windows and doors. Second floor end unit with additional windows flood the home with natural light and stunning bay views. Outdoor living is elevated with a lanai overlooking the water perfect for enjoying spectacular sunsets from this tranquil setting. This boutique community consists of only 6 residences with low Condo Fees, offering a private exclusive atmosphere minutes to 5th Avenue, 3rd Street, the city's world class shopping, dining, arts and white sandy beaches.

3 Beds ⋅ 2 Baths ⋅ 226013181 MLS

Completely renovated 3 bedroom, 2 bath, TURNKEY furnished BY ARHAUS, waterfront condo on Naples Bay with Direct Gulf access & 26 ft Boat Slip, NEW ROOF JULY 2026. The interior has been COMPLETELY RENOVATED and NEVER LIVED-IN with luxury finishes and elegant Arhaus furnishings throughout creating a stylish and functional living space including impact windows and doors. Second floor end unit with additional windows flood the home with natural light and stunning bay views. Outdoor living is elevated with a lanai overlooking the water perfect for enjoying spectacular sunsets from this tranquil setting. This boutique community consists of only 6 residences with low Condo Fees, offering a private exclusive atmosphere minutes to 5th Avenue, 3rd Street, the city's world class shopping, dining, arts and white sandy beaches.

1390 Chesapeake Avenue Unit 1390, Naples

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