Oyster Bay Real Estate, Homes, Condos for Sale in Naples, FL

One or more photo(s) has been virtually staged, AI generated or rendered. Exceptional waterfront opportunity at 1630 Chesapeake Avenue in desirable Oyster Bay, near Royal Harbor. Enjoy southern exposure on a wide, deep-water canal with direct Gulf access and no bridges. The private boat dock accommodates vessels up to about 40 feet, making it ideal for boating enthusiasts. The existing four-bedroom, three-bath home features a new roof, impact windows, and a large pool in a private waterfront setting. The home sustained flooding, and the interior has not been restored, offering an opportunity to renovate to your vision or explore building a new waterfront residence. Just minutes from downtown Naples, Fifth Avenue South’s shopping and dining, and the Gulf beaches, this property combines an outstanding location with exceptional potential.

1630 Chesapeake AVE, Naples

Courtesy of Compass Florida LLC. 239-564-3819

$3,095,000

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 AVE, Naples

Courtesy of Premiere Plus Realty Company.

$7,995,000

5 Beds ⋅ 5.5 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 ST, Naples

Courtesy of John R Wood Properties.

$2,900,000

3 Beds ⋅ 2 Baths ⋅ 226030870 MLS

MUST-SEE FULLY REMODELED WATERFRONT HOME — DESIGNED TO THE MAX! TWO BOAT SLIPS with lifts! Prepare to be impressed by this extraordinary, fully remodeled home where luxury, sophistication, and the ultimate Naples lifestyle come together. Every detail has been thoughtfully designed and beautifully executed, creating a truly exceptional residence that is partially furnished and move-in ready. The stunning chef’s kitchen is the heart of the home, featuring high-end appliances, designer fixtures, custom finishes, and an impressive 14-foot island that provides the perfect gathering space for family and guests. The open, sophisticated design seamlessly connects the kitchen to the main living areas, creating a spectacular setting for both everyday living and entertaining. Step outside to the expansive marble front patio, where breathtaking views of the bay create an unforgettable backdrop. With two boat slips, this property offers an incredible opportunity for boating enthusiasts to enjoy the waterfront lifestyle right from home. The large backyard patio is an entertainer’s dream, complemented by a heated saltwater pool perfect for relaxing, dining, and hosting guests. Whether enjoying a quiet afternoon by the pool or entertaining friends and family, this outdoor space is designed to make the most of the beautiful Naples lifestyle. Additional upgrades include a new roof and new custom wrought-iron doors, adding timeless elegance and peace of mind. No detail was overlooked in this exceptional renovation. Ideally located in the heart of Naples, this remarkable property puts you close to the best the area has to offer while providing the luxury, waterfront setting, and boating lifestyle you've been searching for. This is more than a home — it’s a Naples lifestyle. Truly a must-see!

1095 Sandpiper ST, Naples

Courtesy of Premiere Plus Realty Company.

Selling Office: Premiere Plus Realty Company.

$3,899,000

3 Beds ⋅ 3.5 Baths ⋅ 226013587 MLS

No bridges between your dock and the Gulf. This Oyster Bay home sits on a canal more than 120 feet wide with direct access to Naples Bay and Gordon Pass, and a private Ipe dock with boat lift, water and power. The rear faces south over a screened, heated pool and overflow spa and a covered outdoor dining area. Inside, 3,062 square feet on one level offer 3 bedrooms plus a den and 3.5 baths in a split plan: the primary suite and one guest bedroom open to the pool, while the second guest bedroom and the den each have their own covered sitting area. The lighthouse-inspired design brings vaulted ceilings, custom millwork, painted detailing and natural light throughout. For the boat owner, the 24 by 24 garage has a 12-foot ceiling with height for car lifts, its own mini-split air conditioning and an oversized closet for tackle and gear. Concrete block construction with vinyl siding, a metal roof, and electric and manual storm shutters, with central air conditioning replaced in 2019 and the water heater in 2025. Built in 2002 and kept in its original finishes, it gives the next owner a sound waterfront home to update to their own taste. Minutes to Tin City, the Bayfront and Fifth Avenue South. Floor plan and 3D tour attached.

1510 Chesapeake AVE, Naples

Courtesy of Compass Florida LLC. 239-505-5254

$1,499,000

3 Beds ⋅ 2 Baths ⋅ 226013181 MLS ⋅ Oyster Bay BLDG.

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 AVE Unit 1390, Naples

Courtesy of Coldwell Banker Realty.

$915,000

2 Beds ⋅ 2 Baths ⋅ 226012455 MLS

New Metal Roof! No HOA fees! Private location 1 mile to downtown! Tucked away on a private street in the Royal Harbor area. Boat slips available for lease nearby! Beautiful Old Florida multi-level home with double garage, bonus ground-floor guest/mother-in-law suite with spacious open area, private bath and screened lanai. Spacious and sunny great room design with island kitchen, screened lanai and open deck. The top-quality finishes, open layout and exceptional location near upscale shopping dining and the white sandy Gulf beaches make this home the perfect opportunity to live the Naples lifestyle.

1225 Sandpiper ST, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$3,580,000

4 Beds ⋅ 3 Baths ⋅ 225084283 MLS

Discover an exquisite waterfront sanctuary at 1506 Jewel Box Avenue, perfectly positioned on one of Royal Harbor’s widest canals. This exceptional property offers an impressive 130 feet of total water frontage with two private docks and bridge-free access to Naples Bay and the Gulf waters—ideal for avid boaters seeking seamless adventures on the water. Completely transformed into a sophisticated modern masterpiece, this 2,777-square-foot residence has never flooded and sits at 10.25 feet elevation. Its design thoughtfully blends organic materials with cutting-edge smart technology, and every detail has been meticulously curated for beauty, functionality, and enduring value. The open living spaces feature soft hardwood floors, recessed LED lighting, upgraded interior doors, designer fixtures, and striking architectural ceiling beams. A desirable split floor plan centers around an expansive, panoramic screened lanai with a resort-style pool, promoting effortless transitions between formal and casual living, indoor elegance, and outdoor relaxation. The gourmet kitchen is a chef’s dream, equipped with premium brushed black Samsung appliances, natural stone countertops, soft-close wood cabinetry, a generous breakfast bar, convenient recessed charging station, and subtle under-cabinet toe-kick lighting. The luxurious primary suite serves as a private waterfront retreat, complete with serene canal views, dual walk-in closets, and a spa-inspired bathroom featuring a freestanding soaking tub, separate rain shower, dual vanities with backlit LED mirrors, and a state of the art smart toilet. On the opposite wing, two additional bright and spacious bedrooms offer ample closet space for ultimate privacy. A versatile fourth bedroom with double French doors doubles perfectly as a home office, den, or meditation room. The multifunctional laundry room elevates everyday convenience with custom cabinetry, a utility sink, built-in drying racks, and direct access to the climate-controlled two-car garage. Outdoor living is equally impressive, designed for year-round enjoyment. The pool area boasts a sun shelf, integrated spa, elevated swing seating, custom dynamic lighting, and built-in fountains. A third full bathroom is conveniently tucked under the covered lounge with a built-in gas fireplace. Landscape lighting creates magical ambiance throughout the entry garden, rear deck, and docks. What truly distinguishes this home is its unparalleled boating lifestyle. The rear features an expansive Trex deck with outdoor shower, sun lounge area, swim platform and a 65-foot dock. Across the street, an additional 65-foot dock includes a 30,000-pound boat lift and protective canopy, plus four bonus parking spaces. All this awaits on a peaceful, quiet street in the prestigious Royal Harbor neighborhood—minutes from downtown Naples’ world-class dining, shopping on 5th Avenue South, and pristine Gulf beaches. Experience refined coastal living at its finest!

1506 Jewel Box AVE, Naples

Courtesy of Compass Florida LLC.

Selling Office: Douglas Elliman Florida,LLC.

$11,450,000

4 Beds ⋅ 5.5 Baths ⋅ 225055013 MLS

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.

1340 Jewel Box AVE, Naples

Courtesy of VIP Realty Group, Inc..

Selling Office: Premier Sotheby's Int'l Realty.

$715,000

2 Beds ⋅ 2 Baths ⋅ 225045545 MLS ⋅ Oyster Bay BLDG.

El Nido is a small enclave of four condominiums in the Royal Harbor area with direct Gulf access from your deeded boat dock. Just minutes from downtown Naples and the Gulf beaches. Spacious 2+den with volume & tray ceilings. Tile flooring throughout with Plantation Shutters on the windows. Both bedrooms have large walk-in closets, with the primary ensuite having both a soaking tub and separate shower. This community has a large pool and hot tub surrounded by brick pavers, and a sun deck that leads out to your boat dock. Building updates include a new roof in 2022, pool and pool deck in 2023, and the exterior painted in 2024.

1485 Chesapeake AVE, Naples

Courtesy of John R Wood Properties.

Selling Office: William Raveis Real Estate.

$925,000

3 Beds ⋅ 2 Baths ⋅ 224096356 MLS ⋅ Oyster Bay BLDG.

You will love this perfectly updated and situated residence for boating with your own deeded 20' dock! Lovingly updated end-unit boosts a fresh, current feeling for comfort and entertaining. Light and bright with windows and sliders to access what feels like your own private pool and spa. Unique quaint 4 residence building with an almost new roof. Seller has done a wonderful renovation of the kitchen and baths (see the professional floor plan with the updated configuration), along with light wood-look tile floors throughout. Fully furnished with exclusions. Direct Gulf or Inland waterway access through Naples Bay. No bridges! Boat to the beach, restaurants, or go fishing. Building updates include new roof 2022, pool and pool deck 2023, building exterior paint 2024.

1483 Chesapeake AVE, Naples

Courtesy of John R Wood Properties.

Selling Office: Palm Paradise Realty Group.

$4,500,000

4 Beds ⋅ 4 Baths ⋅ 224040132 MLS

This home is located on Jewel Box Avenue, a highly sought after quiet cul-de-sac street in Oyster Bay. Jewel Box Avenue has canals, water access, on the front as well as the back of the house. Includes a 12,000 Lb boat lift on the back dock and two (2) boat lifts (7,000 Lb and 27,000 Lb) plus a jet ski lift on the front dock across the street. Currently two (2) of the lifts are leased, adding to any rental income potential. Enjoy endless sunsets and fourth of July fireworks with southern views of Naples Bay from the second floor with corner pocket sliders leading out to the balcony. The two (2) corner pocket sliders on the first floor lead out to the infinity pool, waterfall spa and covered patio grill area with a gas grill and electric smoker. This home boasts four (4) bedrooms, four (4) full baths, monitored alarm system, tile throughout, bamboo floors in the den, hardwood floors on stairway and second floor, quartz countertops, stainless steel appliances, tin ceiling over dining area, coffered ceilings in living / family room and three (3) newer HVAC systems plus a split unit. Home is a stone's throw to the open waters of Naples Bay and minutes to world class beaches, shopping and dining. Due to elevation there were no issues with recent storms.

1400 Jewel Box AVE, Naples

Courtesy of Premiere Plus Realty Company.

Selling Office: Premiere Plus Realty Company.

$10,675,000

4 Beds ⋅ 5.5 Baths ⋅ 224020793 MLS

Enjoy endless, unobstructed West facing, year-round sunsets from one of Naples most unique and special waterfront properties. Over 350 feet of direct Gulf of Mexico water access from your private peninsula setting. An exceptionally designed floor plan ensures spectacular water views from nearly every room/bedroom. Encompassing 5,619 sq ft under air, 4 en-suite bedrooms (2 w. morning kitchens and ALL with direct balcony/lanai access), 5th bed/den, 6 Bathrooms, plus an incredible amount of places to sit, gather, relax and entertain the entire family & friends. Built to the highest code/standards in 2018, the home is now better than new, with a long list of upgrades and enhancements to the already superior built, all concrete residence. Professional interior design and offered turn-key furnished (valued at $600K+)! Beautiful white oak wood and marble flooring throughout, Chef’s kitchen boasting Sub-Zero and Wolf appliances, built-in bar, wine refrigerator and an abundance of storage complete the warm, timeless decor and inviting space. There’s even a water view from your private elevator; or utilize the gorgeous staircase lined with glass railing and a stunning motorized chandelier (cleaning is a breeze). Convenient 1st floor primary suite has an impressive layout, large walk-in closets, dual sinks, bidet, and private lanai sitting area. Open the interior doors & enjoy bay views from the soaking tub. Outside you will discover a wealth of options for entertainment and leisure, epitomizing the luxurious Naples lifestyle. Bask in the sun-drenched stunning infinity edge pool with large spa or enjoy the separate bay front hot tub off the main living. Massive 2nd story balcony area is ideal to watch the colorful sky change from day to night. Architecturally designed landscaping areas have been curated to create a special ambiance of privacy and tranquility. Pool equipment has been automated and upgraded. Wall garden, water feature and custom California redwood tree door compliment the space. Multiple docks have been upgraded, including the enormous 900’ West facing fishing/relaxing pier and the 1,200' sq ft North side pier boasting 24,000 lbs boat lift & 13,000 lbs 4 jet-ski and kayak lift/platform! Inside and out of this estate home is an entertainer’s dream. Enjoy 270-degree views from the open outdoor summer kitchen (attached full pool bath); control the ambiance and comfort level with the press of a button, adjusting the Lutron lighting, electric roll down hurricane shutters and bug screens, security cameras, 7 Sonos zones. New HVAC systems installed in 2023 (7 zones including all garages are conditioned). Split 3 car garages, one w. a car lift, tons of built-in storage. Beautiful laundry area w. washer & 2 gas dyers. Short 1.6 mile walk/drive to the heart of Olde Naples & 5th Ave! Enjoy the sugary white sand beach and endless shopping and dining venues. Don’t miss this opportunity to own a nearly 1/2 acre direct Bayfront gem w. over 350' of frontage.

1340 Jewel Box AVE, Naples

Courtesy of Premiere Plus Realty Company.

Selling Office: VIP Realty Group, Inc..

$6,000,000

4 Beds ⋅ 3.5 Baths ⋅ 224009068 MLS

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.

1490 JEWEL BOX AVE, Naples

Courtesy of William Raveis Real Estate.

Selling Office: John R Wood Properties.

$550,000

2 Beds ⋅ 2 Baths ⋅ 224011485 MLS ⋅ Oyster Bay BLDG.

ACCEPTING BACKUP OFFERS!... FANTASTIC DOWNTOWN LOCATION... LOCATED DIRECTLY ON A NAPLES BAY CANAL WITH DEEDED USE OF BOAT SLIP (25' BOAT) AND NEWLY RENOVATED COMPOSITE DOCK...PADDLEBOARD, KAYAK, OR FISH OFF YOUR OWN DOCK...ONLY MINUTES OUT TO THE GULF WITH NO BRIDGE... WALK OR BIKE TO 5TH AVE, BAYFRONT, TIN CITY... NEW COMPLETELY RENOVATED 2/2... NEW KITCHEN WITH QUARTZ COUNTERS, ALL NEW APPLIANCES, TILED BATHROOMS/SHOWERS, NEW IMPACT WINDOWS AND SLIDER, NEW WOOD LAMINATE FLOORING THROUGHOUT, NEW AC.. WALK TO THE GORGEOUS NAPLES BAY RESORT ON PRIVATE PATH FROM THE PARK WHERE THERE ARE SEVERAL DINING OPTIONS INCLUDING COFFEE SHOP, FINE DINING, BOAT RENTALS AND MARINA... LOCATION, LOCATION, LOCATION... CALL TODAY TO VIEW THIS IDEAL CANAL FRONT CONDO.

1575 Curlew AVE Unit 2-4, Naples

Courtesy of Amerivest Realty.

Selling Office: EXP Realty LLC.

$3,000,000

3 Beds ⋅ 3 Baths ⋅ 224006657 MLS ⋅ Oyster Bay BLDG.

This exquisite home offers breathtaking unparalleled panoramic views of stunning Naples Bay from every window. The expansive water views throughout the home invite you to unwind and savor the beauty that surrounds you from every room. With three bedrooms each with their own private bath, and an open floor plan that effortlessly connects the interior space with the stunning outdoor scenery. The home has been completely renovated top to bottom featuring an open marble staircase, built ins and upgrades too numerous to mention. An outdoor deck designed to maximize the stunning water views extends gracefully from the side of the home. Home is deeded with it's own private boat dock. Nestled in an enclave of 8 exclusive townhomes with a centerpiece of just renovated pool and new Tiki Hut combined with the exquisite architecture of these townhomes provides a seamless blend of coastal luxury. A must see. Call for a private appointment.

1303 Chesapeake AVE Unit 2-A, Naples

Courtesy of Douglas Elliman Florida, LLC.

Selling Office: Douglas Elliman Florida, LLC.

$1,715,000

3 Beds ⋅ 2 Baths ⋅ 223061734 MLS

Completely remodeled in 2017 Boathouse on the bay, this contemporary home boasts breathtaking sunset views in Oyster Bay down the canal. Walk to 5th Avenue or access your boat slip across the street (available for separate purchase). Newly built docks in 2017 have no annual costs. South Slip for $200,000 (accommodates up to 29 ft boat, 12,000 pounds), North Slip for $300,000 (up to 34 ft, 18,000-pound lift). This lucrative Airbnb property earned nearly 200k in annual income. Step inside, and you'll be greeted by vaulted living room ceilings, skylights, impact sliders that open all the way to an inviting open pool, heated for year-round enjoyment. The lush tropical landscaping surrounding the property includes a mature coconut trees, mango trees, and fragrant flowers, adding a touch of natural beauty. Consider the possibilities to enhance the spectacular Bay sunset views by exploring vertical expansion by adding a second story (please refer to supplements), or be inspired by the ongoing construction at 1075 & 1085 Sandpiper to build a stunning 3-story property, exceeding 5000 sq ft. Boater's dream, exceptional opportunity!

1095 Sandpiper ST, Naples

Courtesy of Naples Investment Realty.

Selling Office: Florida Luxury Realty.

$1,115,000

222048130 MLS

Price Reduced !! Multi Family or Single Family buildable Lot in Royal Harbor has direct Gulf access and is seconds to Naples Bay via boat. It is also walking distance to Old Naples, Naples Bay Resort and downtown shops, restaurants, entertainment and beaches. This buildable lot offers a newer seawall and can accommodate a single family home or up to FOUR Luxury Condominiums. Perfect for someone who wants the boating lifestyle in city of Naples for fraction of cost. Zoned Single Family Or Multi Family Build Four Luxury Condos. Only Multi Family lot currently available in Oyster Bay. No HOA Fees !! 106 Feet of Seawall !!!

1493 Blue Point AVE, Naples

Courtesy of Coldwell Banker Realty.

Selling Office: Coldwell Banker Realty.

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