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Florida Keys Homes on the Bay / Gulf Side of the Island For Sale

Total Listings 376
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$725,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
2 Bed, 2 Baths, 1,196 SqFt Days Listed: 25
-3.20% ($24,000) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

New Listing! Key West home on 50x100 lot in Midtown East. This home offers 2 bedrooms, 1 full bath with room to expand. Living room with hardwood floors opens the kitchen and flows to the spacious family room. Family room offers built-ins, storage, and doors to the private backyard. Primary bedroom is spacious and features a large closet. Workshop/shed for extra storage space. Central AC. Hardwood and ceramic tile floors. Room for a pool and gardens.

$725,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 884 SqFt Days Listed: 148
-12.11% ($99,900) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: BasinConcrete

DIRECT ACCESS to the beautiful FLORIDA KEYS - Eden Pines in Big Pine Key. This delightful waterfront home with New hardy plank siding features two bedrooms and one bath upstairs with an open concept layout. Theres also a bonus room that offers flexible options, like working from home or pursuing hobbies, while enjoying many comforts! Priced below appraisal.Some highlights include gracious water views, tropical landscaping, serene lighting, and a canal with ocean access. concrete seawall, and a personal boat basin for safety and security. Youll also find impact windows with a 145 mph wind load capacity. This sweet bungalow features a remodeled- redesigned specialty chefs kitchen with a gas stove, quartz counters, farm sink and sensational, tropical views.This captivating retreat home can sleep six.. Did someone say...Perfect Airbnb!Perfect Keys Home or investment Vacation Rental. Location-Location! On the water! Buyer to verify

$725,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 365
-12.12% ($100,000) 4 Price Changes : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits188ft.

Welcome to our cozy retreat nestled on Big Pine Key. This charming two bedroom one bath cottage offers a tranquil escape on a DOUBLE LOT fenced, providing privacy and security. Enjoy the picturesque waterfront views from your own back yard. Florida room with large impact windows to capture the water views. Impact windows through out. Approximately 273 feet of concrete seawall with davits, Small garage for extra storage. Property is also 100 % handicap accessible. This home is your gateway to laidback island living. Make offer!!

$735,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 219
-8.01% ($64,000) 2 Price Changes : Last Change 55 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Freshly remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast sleek quartz countertops and newly installed cabinets and backsplash. Both bathrooms have been upgraded. Gorgeous high end tiling in shower and floor, accompanied by new vanities. Throughout the house is luxury plank vinyl flooring and crown molding to make this home shine even more. Off main living area is an expansive back deck for relaxation. Local grocery store, dog park, and food/beverage only minutes away! Like what you see? Call today!

$749,900
Big Pine Key
Sea View   - MM: 28.00
2 Bed, 2 Baths, 864 SqFt Days Listed: 79
-13.21% ($114,100) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Ultimate Privacy in Big Pine KeyStep into an extraordinary sanctuary of seclusion, where tropical elegance meets unmatched exclusivity. 1 of only 2 homes in the entire Seaview subdivision of Big Pine Key.3231 Pompano Drive is a beautifully renovated island retreat set on a 10,000 sq. ft. lot, surrounded by untouched nature and abundant wildlife. No additional homes can ever be built, ensuring that this private paradise remains forever preserved.Inside, the open-concept living space is designed to impress, flowing seamlessly into a stunning kitchen featuring shiplap tile accents, new cabinetry, quartz countertops, stainless steel appliances, and a propane stove. Vaulted wood-beamed ceilings, mini-split A/C units, AT&T Fiber, tankless hot water and brand-new vinyl plank flooring add to the homes tropical charm. Sunlight pours in through expansive windows, showcasing breathtaking views of the pristine nature preserve.Designed for indoor-outdoor living, this home offers a screened upper porch, ideal for peaceful mornings surrounded by nature. The spacious screened enclosure downstairs provides a private retreat, while the swim spa is perfect for unwinding under the stars.With ample parking for an RV with hookkups, boat, trailers, and more, this home is an outdoor lovers dream. A nearby boat ramp ensures quick access to world-class fishing, kayaking, and boating.Come see this secluded oasis-paradise awaits.

$750,000
Big Pine Key
Koehns Subdivision   - MM: 30.50
3 Bed, 3 Baths, 1,482 SqFt Days Listed: 143
-5.66% ($45,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Fenced 27,500 sq. ft. lot with big double gates, perfect for local contractors!! This spacious 3 bedroom 2 bath pool home is nestled on .63 acres of fenced tropical landscape offering unparalleled privacy and tranquility. Surrounded by wildlife preserve, this is a nature-lovers dream home located in the Florida Keys Wildlife Refuge. This fabulous keys property has so much to offer with almost 1500 square feet of living space including a huge master suite with an updated bath with soaking tub and a massive walk in closet. The super cute galley style kitchen and large adjacent dining area make it easy to prepare gourmet meals and entertain guests. The living area has a working fireplace for ambiance on those few cool weeks we see in the winter. Step outside to enjoy the peace and quiet of your expansive fenced in back yard which is perfect for families with pets. In addition to the in ground pool, you are afforded a tremendous space for outdoor entertaining, landscaping, storing all of your work equipment, toys, trailers, and RVs. There are many walking and biking trails in the neighborhood where you can see our local wildlife first hand in their natural environment. You can find Key Deer, Great Blue Heron, Egrets, White Ibises, Roseate Spoonbills, Ospreys, and Eagles, as well as the occasional siting of Flamingoes, just to name a few. The community boat ramp is at the end of the street for your convenience. VA Assumable Loan at 4.125% to qualified VA Buyers only.

$750,000
Marathon
N Marathon Shores   - MM: 51.50
3 Bed, 3 Baths, 1,668 SqFt Days Listed: 331
-9.09% ($75,000) 5 Price Changes : Last Change 64 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to your dream home on Gulfstream Blvd in the heart of Marathon, Florida Keys! This stunning single-family residence offers the perfect blend of luxury, comfort, and convenience. Located close to a variety of amenities including top-rated restaurants, grocery stores, Sombrero Beach and the Harbor Dr. boat ramp, this home is ideal for those seeking the quintessential Florida Keys lifestyle. Step inside to discover an open floor plan that seamlessly connects the living, dining, and kitchen areas. The gourmet kitchen is a chefs delight, featuring a propane Viking range, stove, and hood, a Sub-Zero refrigerator, and a wet bar sink with a garbage disposal. Mexican tile and terrazzo flooring add a touch of elegance and durability throughout the home. This beautiful residence boasts 3 spacious bedrooms and 2 modern bathrooms, plus a bonus Florida Room that can be used as an office, playroom, or additional living space. The newer washer/dryer, A/C, and dishwasher ensure you have the latest in home conveniences. Outside, enjoy the privacy of a fenced-in backyard, perfect for relaxing or entertaining, complete with a storage shed for all your outdoor gear. The pavered driveway, impact windows and doors, and metal roof provide both security and peace of mind. Large yard provides the possibility of putting a pool in your backyard! Dont miss this opportunity to own a piece of paradise. Schedule a showing today and experience the luxury and convenience this home has to offer.Envision entertaining friends in your spacious, open living area or whipping up gourmet meals in your dream kitchen. Relax in your private, fenced backyard - the perfect spot for those lazy Sunday afternoons or starlit evening gatherings. Picture yourself strolling to nearby Sombrero Beach, savoring exquisite meals at local hotspots, or setting sail from the nearby boat ramp. Your new home is your personal oasis, where indoor and outdoor living blend seamlessly.

$750,000
Marathon
Grassy Key   - MM: 58.90
3 Bed, 3 Baths, 1,548 SqFt Days Listed: 58
-6.13% ($49,000) 1 Price Change : Last Change 15 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to your private oasis on Grassy Key, where your closest neighbors are the dolphins! Just steps away, youll find the S.S. Wreck & Galley Grill, Grassy Key Marina, a bait shop, and a grocery store--everything you need for the perfect island lifestyle. This 3-bedroom, 2-bathroom stilted home is the epitome of privacy, relaxation, and Florida Keys living. Designed for comfort and durability, this elevated home features impact windows and doors, a metal roof, and Hardie board siding, all updated in 2018. Inside, 1,548 sq. ft. of thoughtfully designed space awaits, with brand-new Lifeproof flooring throughout and an abundance of natural light. The kitchen is fully equipped with stainless steel appliances and a brand-new refrigerator, while the primary suite offers a spa-like retreat with a jacuzzi tub and double vanity. A versatile bonus room provides space for an office, play area, or creative nook. But the true magic happens outdoors! Step into a tropical escape featuring a custom heated & chilled concrete pool, six-person jacuzzi, and an expansive outdoor kitchen and bar--perfect for entertaining under the swaying palms. The MistAway mosquito control system ensures uninterrupted enjoyment of your private backyard oasis. Situated on an oversized, fully fenced lot, theres ample space for parking boats, trailers, and all your island toys. Beneath the home, additional storage provides a perfect place to stow gear for fishing, diving, or boating adventures. Enjoy unparalleled tranquility with the Dolphin Research Center bordering the property, guaranteeing no neighbors on two sides!

$765,000
Marathon
Grassy Key   - MM: 58.90
3 Bed, 3 Baths, 1,008 SqFt Days Listed: 139
-3.95% ($31,500) 1 Price Change : Last Change 88 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Enjoy complete privacy in this gated property on Grassy Key at the end of Cocoanut Ave. A true escape with manicured outdoor living areas, heated pool, large storage, screened porch, tropical landscaping, ample parking and RV hook-up parking. The elevated home offers 3 spacious bedrooms, 2 bathrooms, an open floor plan living area and screened porch overlooking the pool. The home is in excellent condition ready for you to move right in and start living your best Keys life. Call today for more information and schedule a private tour.

$775,000
Big Pine Key
Ross Haven   - MM: 31.00
2 Bed, 2 Baths, 912 SqFt Days Listed: 47
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: DavitsConcrete

Welcome to your slice of paradise in the beautiful Florida Keys! This 2-bedroom, 2-bathroom canal-front home is perfectly situated in Big Pine Key, offering direct access to the renowned Bogie Channel and some of the best boating in the area. Enjoy nice views of the open water.Enjoy 50 feet of concrete seawall, complete with boat davits, making it easy to launch and dock your vessel. The screened porch provides the perfect spot to relax and take in the partial open water views, while gentle sea breezes flow through. A cargo lift makes transporting supplies effortless, and additional storage ensures plenty of room for all your gear.Surrounded by the natural beauty of Key Deer Refuge and just minutes from Bahia Honda State Park, this home offers a serene yet adventure-filled lifestyle. Whether youre fishing, diving, or simply soaking up the laid-back Keys atmosphere, this is the ideal waterfront retreat.Dont miss this rare opportunity--schedule your private showing today!

$780,000
Plantation Key
Lake Harbor   - MM: 89.50
4 Bed, 4 Baths, 1,540 SqFt Days Listed: 72
-9.30% ($80,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Discover your slice of paradise in Tavernier! This delightful 3-bedroom, 2-bathroom home features a bonus room and a fenced-in outdoor space shaded by beautiful, mature trees. Enjoy brand-new flooring and impact-resistant windows throughout. The open and spacious kitchen creates an ideal setting for entertaining. Youll also benefit from year-round shade provided by the large trees surrounding the property. Plus, youll have access to the Plantation Key Colony Boat Ramp, making it easy to launch your boat. Whether youre looking for a full-time home or a vacation retreat, this property offers the ultimate Florida living experience. Dont miss out on the opportunity to own a piece of paradise--call today!This single-family home was originally in the process of being converted into a commercial property within the Village of Islamorada. Due to the extended timeline for completion and the anticipated duration, the seller has decided to list the property. With the proper guidance and approval from the Village of Islamorada, this property can easily be transformed into a commercial space. It is located in the Highway Commercial (HC) zoning district.seller is a licensed real estate agent

$780,000
Big Pine Key
Big Pine Key Inc   - MM: 31.00
2 Bed, 2 Baths, 1,447 SqFt Days Listed: 59
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

CHARMING HOME NESTLED IN THE TREES ... if you love nature and a bit of privacy, this 14,000 sq. ft. property is not to missed. The conveniences and amenities that Big Pine Key offers are easily accessible by foot, bicycle and car. Look in any direction and all you see are trees! Custom-built, the home has wonderful porch spaces on two levels ... its light and bright inside with abundant windows and French doors, and a soaring cathedral ceiling in the living room and primary suite / loft walkways in the upper level. The kitchen features custom mahogany and African mahogany counters, as well as a stunning wood ceiling. On the main level youll find one bedroom and bath, and the upper level has the primary bedroom with ensuite bath and loft areas for an extra guest, office and quiet reading. New roof in 2018; recent central AC. There are trees in every direction that one looks; the east and west facing porches on both levels are prime for bird watching. If you enjoy walking or biking, its a 10-minute walk to the post office, and a short walk or bike ride to Winn Dixie Plaza, drug stores, banks, and the Pine Channel Nature Park. On the ground level youll find covered parking, 500 sq. ft. of storage, and a great storage shed tucked away in the back of the property. Cleared to the south, the double lot measures 100 x 140. Come see why the current owner has loved this home and property for over 30 years!

$789,000
Big Coppitt
Gulfrest Park #2   - MM: 10.00
2 Bed, 2 Baths, 1,166 SqFt Days Listed: 164
-4.36% ($36,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 150ft.

Discover your ideal Keys retreat in this delightful 2 bedroom, 2 bathroom home, perfectly situated just a short 15-minute drive from Key West. Step inside to experience an inviting open floor plan accentuated by vaulted ceilings and a generously sized kitchen, ideal for both relaxing and entertaining.The master bedroom offers a private ensuite bathroom and opens onto a covered porch overlooking the serene canal. Outside, a fenced yard ensures privacy, making it a haven for pets and peace of mind.Enhancing this propertys allure are its coveted amenities: a covered back porch for al fresco dining, a sturdy concrete dock for your boat, a convenient workshop space, and seamless boating access to both the Gulf and Atlantic waters. Whether youre seeking a tranquil escape or an active waterfront lifestyle, this home embodies the essence of Keys living. Dont miss the opportunity to make it yours - schedule your showing today and let the beauty of the Keys captivate you.

$789,000
Ramrod Key
Ramrod Shores   - MM: 27.00
3 Bed, 3 Baths, 1,488 SqFt Days Listed: 9
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Welcome to your slice of paradise in Ramrod Key! This newer built (2018) beautifully maintained single-family home offers 1,488 square feet of comfortable living space, perfectly situated on a spacious 6,000 square foot lot. Featuring 3 bedrooms and 2 bathrooms, this property is ideal for full-time residents, vacationers, or investors seeking a rental opportunity in the Florida Keys.Enjoy the tropical lifestyle with ample outdoor space, including designated RV and boat storage--perfect for all your island adventures. Whether youre relaxing on the porch, heading out on the water, or entertaining guests, this home is designed for easy, breezy coastal living.Dont miss your chance to own a piece of the Keys. Schedule your private showing today!

$789,000
Key Largo
Key Largo Park   - MM: 101.00
3 Bed, 3 Baths, 1,632 SqFt Days Listed: 241
-1.25% ($10,000) 1 Price Change : Last Change 101 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Modern-Well Built home -3 stories high -Solid construction - top of the line finishes appliances - And layout for spacious and privacy - Impact windows Granite counter top -for informal dining - Porcelain tiles, stainless appliances. Metal roof -CBS construction -Roof Gables-Hip -impact windows impact doors -Furniture negotiable -Step up to 2nd level - with 3 bedrooms 2 1/2 baths - combined living room and dining room - Ground level offers a large screen porch - good side patio with trees and folia. Room on left side for a boat - trailer or large trucks.Solid CBS Construction: Durable and built to last with a stylish metal roof.Impact Windows & Doors: Enhanced safety and energy efficiency throughout.Spacious Layout- Great for a large familyBuyers beware To be sure, the Club is open only to members who properly apply, and fulfill the requisite membership requirements, as opposed to a club or feature that is automatically open to any member of the subject association or subdivision Ask for detail.

$792,500
Ramrod Key
Ramrod Shores   - MM: 27.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 61
-4.80% ($40,000) 2 Price Changes : Last Change 22 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 16ft.Cut/Natural

Experience the tranquility of the Florida Keys in this meticulously maintained home, completed in 2019 and ready for your immediate enjoyment. This stunning property showcases thoughtful upgrades totaling over $50,000 by the current owner, designed to elevate your comfort and convenience. The interior offers a seamless blend of modern living and coastal charm, while the impressive NEW 299 sq. ft. storage area--equipped with impact-rated windows and a slider--presents breathtaking views of the swimming canal. This versatile space is perfect for all your storage needs or as a workshop-its a must see! Situated just a short distance from the vibrant locales of Marathon and Key West, youll enjoy the best of both worlds. Outdoor enthusiasts will appreciate the added 30-amp RV hookup and yard space for a 30-foot boat, with a public boat ramp located just a few miles away. Dont miss the opportunity to make this move-in ready gem your new home!

$795,000
Plantation Key
High Point   - MM: 89.00
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 22
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Basin

Islamorada Home - Move-In Ready!2 bed, 2 bath home on a spacious corner lot, fully fenced with an electric gate. Enjoy an amazing homeowners park featuring sunset views, a private beach area, and a boat ramp. Additional storage space downstairs, with washer and dryer conveniently located upstairs. Relax in your own sauna or on the beautiful porch overlooking the trees. Swinging gates allow easy access for a large boat or RV. Great location on Plantation Key near Founders Park. Call today!

$799,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,305 SqFt Days Listed: 127
-5.44% ($46,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Other Dockage

LARGE CORNER LOT LOCATION ON QUIET INTERSECTION. Perfectly located for a family seeking room to roam under numerous native mature trees and a few palms in the heart of Plantation Key in popular X flood zone. This concrete 3-bedroom, 2-bath ranch-style home features vaulted tongue-and-groove ceilings & transom windows for added sunlight in the main living area, complemented by two sets of French doors leading to a spacious concrete patio. The patio, surrounded by a charming wood picket fence, creates an ideal space for kids, pets, and outdoor entertaining. The side yard offers ample room for a future pool or a play area under the shade of mature trees. The front entry showcases Chicago-style brick-paved double driveways, adding both charm and functionality. The immediate area around the home is fenced and includes a detached work/storage shed and a 2nd secluded patio area. A private neighborhood homeowners park is located nearby, providing access to Florida Bay via a convenient boat ramp.

$799,000
Big Pine Key
Palm Villa   - MM: 30.50
3 Bed, 3 Baths, 1,193 SqFt Days Listed: 141
-5.89% ($50,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Discover your dream home on Big Pine Key at this expansive 37,500 sq. ft., property totaling 6 lots that combines privacy, nature, and convenience. Nestled in a serene setting with tropical landscaping and thoughtful features, this home offers a massive yard that goes from street to street and is surrounded by a 6 stockade fence allowing lots of safety and room for kids and pets to play and roam. The 3 Bedroom 2 Bath home offers an open floor plan highlighted with soaring ceilings and garden views from all rooms with no neighbors in sight. The kitchen is a culinary delight with a central island with peninsula seating, wood cabinetry and abundant counter space. Whether youre preparing a gourmet meal or a quick snack this kitchen is equipped for it all. A convenient pantry and a laundry closet add to the functionality, ensuring everything has its place. Enjoy morning coffee or evening cocktails on either the front or back porch while watching key deer roam. The homes split floor plan provides privacy and comfort. The primary suite is a private retreat with a walk-in closet and a en suite bathroom. Additional bedrooms feature engineered hardwood floors and offer plenty of space for family or guests. The propertys outdoor spaces are nothing short of extraordinary. Two tranquil ponds on either side of the lot enhance the peaceful ambiance and can be filled using the private well. Native trees and lush landscaping create a vibrant and serene environment. A stone walkway leads to a spacious 20x20 shed allowing for plenty of room for all of your toys. A garden shed tucked at the back of the lot provides additional storage, while a downstairs covered lanai offers an ideal spot for entertaining, barbecuing, or unwinding in the shade. This property is as practical as it is beautiful, with a covered carport, trailer storage, room for pool and RV and plenty of parking for guests. Whether you need space for recreational vehicles or everyday use, this home has you covered

$799,000
Ramrod Key
Ramrod Shores Marina   - MM: 27.00
3 Bed, 3 Baths, 1,320 SqFt Days Listed: 42
-7.31% ($63,000) 1 Price Change : Last Change 27 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to your dream home in the heart of the Florida Keys! This beautifully designed 3-bedroom, 2-bathroom BUNKER residence on Ramrod Key showcases exceptional craftsmanship and high-end finishes throughout. Well built home..with Impact windows & doors, poured concrete floors, CBS construction with metal roof also wired for a generator.Step inside to find gorgeous porcelain floors and a thoughtfully designed interior..blending elegance with coastal charm. The spacious open-concept layout offers plenty of natural light, perfect for entertaining or simply relaxing in the private surroundings.Enjoy the island breeze from your inviting porch, ideal for morning coffee or sunset cocktails. Additional features include ample storage space, making it easy to keep all your Keys lifestyle essentials organized. Located just minutes from world-class fishing, boating, and breathtaking beaches, this home is your gateway to everything the Florida Keys has to offer.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 05-09-2025.
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