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$1,995,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
6 Bed, 6 Baths, 3,197 SqFt Days Listed: 262
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Discover the essence of island living in this expansive 3,197sf, 6-bedroom, 3-bathroom home, perfectly positioned on a generous 9,500sf corner lot in the heart of Key West. This spacious 2 story CBS home features a gourmet kitchen, tile floors, 2 laundry areas, sundeck & a new roof. The sprawling yard, enclosed by a privacy wall, offers plenty of room for boat and trailer storage, RV parking, and a safe play area for kids and pets. An in-ground concrete pool with water feature adds to the outdoor appeal, while a storage shed provides extra convenience. Offering a rare combination of convenience and space, this residence is ideally located minutes from schools & grocery stores, while also being near the new Happy Landings Marina and the Key West Yacht Club, making boating a breeze! With a flexible layout and ample space, this property is brimming with possibilities, ready to be tailored to your vision of the perfect island retreat.

$1,985,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 2,196 SqFt Days Listed: 2
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to 522 William Street - a rare renovation opportunity nestled in the heart of Old Town Key West. This classic Conch - style home sits on a prized street just steps from the Historic Seaport, world-class dining, and the islands vibrant energy. With its original Dade County pine, soaring ceilings, and vintage architectural details, this diamond in the rough is ready for transformation.Whether youre envisioning a stunning restoration, a tropical retreat, or a lucrative investment, the bones are here. The lot offers ample room for expansion, pool installation, or lush outdoor living. Renovators, developers, and visionaries - this is your blank canvas in one of the most desirable neighborhoods in Key West. Surrounded by luxury homes and consistent buyer demand, this is a prime opportunity to add significant value to the property. Historic charm. Endless possibilities. Premier location. Bring your imagination and create something truly special at 522 William Street.

$1,980,000
Key West
Key West Fwdn Subdivision   - MM: 4.00
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 41
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Stunning New Construction with High-End Finishes and Modern Design!Welcome to this exceptional, brand-new 3-bedroom, 3-bathroom home that seamlessly blends modern design with luxurious living. From the moment you enter, youll be captivated by the soaring vaulted ceilings and high ceilings throughout, creating an airy, open atmosphere. This home is designed with the highest attention to detail, featuring top-of-the-line finishes and stylish, contemporary touches.The heart of the home is the expansive living area and stunning kitchen, complete with sleek cabinetry, gorgeous quartz countertops, and premium stainless steel appliances--ideal for cooking and entertaining in style. The spacious layout flows effortlessly from room to room, offering a perfect balance of functionality and sophistication.Outside, the property is beautifully landscaped, offering a serene and inviting environment for outdoor living. The standing seam metal roof adds both durability and elegance, giving the home a sleek, modern look. Off-street parking with sliding metal gates ensures privacy and convenience, offering an added touch of security.This is a rare opportunity to own a new construction home with everything you could desire--modern design, high-end finishes, and a prime location. Dont miss out on this stunning property!

$1,975,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,128 SqFt Days Listed: 313
-17.54% ($420,000) 4 Price Changes : Last Change 9 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Median - Dockage: None

This charming two-story Old Town cottage in Key West is ideally located just a half block off of Duval Street. The interior was beautifully renovated throughout with new floors, updated kitchen and impact windows & doors. The first floor includes a master bedroom with French doors leading out to an in-ground swimming pool. Upstairs, a loft provides a spacious guest bedroom. Overlooking the large pool and guest cottage which features vaulted ceilings and tiled flooring. A spacious wood deck covered by a large tiki hut connects the main house and guest cottage, creating a seamless indoor-outdoor living experience.The private pool, surrounded by lush landscaping, offers a tranquil retreat characteristic of Key West living. Additional amenities include an outdoor shower and covered off-street parking.

$1,950,000
Key West
Old Town Unrecord   - MM: 1.00
2 Bed, 2 Baths, 1,312 SqFt Days Listed: 106
Single Family - Contingent - Waterfront No
Side of Island: Median - Dockage: None

Experience the epitome of Key West living in this exquisitely renovated 2-bedroom, single family home nestled within the exclusive gated community of Truman Annex. The first floor of this beautifully renovated Coastal designed home features a gourmet kitchen with top-of-the-line appliances, a spacious sun-filled Living Room and Dining Room made for hosting unforgettable gatherings. The private back patio offers outdoor entertaining space for dining, grilling, and soaking up the sun. Both elegantly appointed bedrooms are located on the second floor, each with their own dedicated bathroom. A truly unique feature of this home is the elevator, allowing for easy access and transport to the second floor. The prime location of this home makes it easy to take a quick Stroll to all that Key West has to offer - the nearby Truman Waterfront Park, first-class restaurants, art galleries, shopping, and the lively music scene. Additional benefits include one designated parking space, access to the community pool, a private outdoor shower, Impact Resistant Windows & Doors, and weekly transient rental license. Being offered turn-key, this home is ready to move right in and enjoy your slice of paradise!

$1,950,000
Key West
Moffats Subdivision   - MM: 2.00
3 Bed, 3 Baths, 1,644 SqFt Days Listed: 33
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This one-of-a-kind Conch house effortlessly blends island charm with modern sophistication. Featuring three spacious bedrooms and four luxurious bathrooms, the home boasts stunning wall-to-wall Dade County pine that adds character and warmth throughout. The open floor plan is ideal for both entertaining and everyday living, seamlessly connecting the living area to a chef-inspired kitchen.The kitchen is a culinary dream, with sleek quartz countertops, top-of-the-line stainless steel appliances, and ample space for creating gourmet meals. Just beyond the kitchen, step into a private outdoor oasis. Surrounded by lush, mature landscaping and beautiful brick pathways, the serene courtyard leads to an oversized heated pool - perfect for a relaxing dip or enjoying the tranquil surroundings.Located just steps from Key Wests vibrant dining, art galleries, and historic landmarks, this home offers the best of both seclusion and convenience. A truly special retreat that invites you to experience island living at its finest.

$1,950,000
Key West
Kamien Plat #1   - MM: 2.00
3 Bed, 3 Baths, 2,017 SqFt Days Listed: 115
-15.22% ($350,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Effortless style, prime location, and outdoor living at its best. Welcome to your dream coastal beach cottage, tucked away in a quiet midtown neighborhood. This completely updated one-level home offers the perfect combination of privacy, convenience, and island charm. Just minutes from the beach and walkable or bikeable to Key Wests best restaurants and cafes, 1619 Rose Street is perfectly situated to embrace the ultimate island lifestyle.Step into a thoughtfully designed home with an open floor plan that flows seamlessly from the living area to the dining room, kitchen, and out to the expansive lanai. The master suite is a true retreat, with sliding glass doors opening directly to the pool area, a walk-through shower, and a custom-fitted walk-in closet.The centerpiece of this home is the lushly landscaped backyard oasis. Surrounded by tropical greenery, it features a heated pool, multiple outdoor living spaces, and a serene ambiance perfect for relaxing or entertaining. Completing this outdoor paradise is a detached one-bedroom, one-bath guest cottage with its own private deck overlooking the heated and chilled pool--ideal for visitors or a private home office.Modern design, thoughtful details, and the very best of Key West living await you in this stunning island retreat. Being sold furnished excluding artwork.

$1,925,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 204
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Experience the charm of Old Town living at 923 Eaton St, a beautifully updated historic home featuring three bedrooms and two full bathrooms, ideally situated just steps from the Historic Seaport and a short stroll to Duval Street. Offered turn-key, this property combines classic Key West architecture with modern enhancements, making it perfect for enjoying the local lifestyle.Inside, youll find Dade County Pine walls, hardwood floors, and renovated kitchen and bathrooms. The second floor boasts two inviting bedrooms, while the first floor offers a charming bunk room. Step outside to discover a spacious 10x20 ft heated saltwater pool and a private tropical backyard oasis, perfect for outdoor relaxation. Additional features include a newer metal roof, an impact-rated sliding glass door leading to the rear deck, and efficient ductless AC units.This charming home is fully furnished and ready for you to move right in or to generate a reliable income as an investment property, allowing you to enjoy all that Key West living has to offer!

$1,900,000
Key West
Key West Investment Co Subdiv   - MM: 1.00
3 Bed, 3 Baths, 2,157 SqFt Days Listed: 5
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This historic property was originally a single family home and could be converted back to same. Currently configured as 3 apartments in the main building, youll find treasured Dade County Pine and hardwood floors throughout. Hansen & Bringle cabinetry, central A/C down. Upstairs configuration is 2 studio apartments, both with outdoor space and these could be additional bedrooms with en-suite baths. There is a separate building with a rare and highly desirable garage with a studio apartment above. In addition, there is a small heated pool. This is a great mid-town location and with the possibility of an owner having an historic single family home with a separate structure for a family member, caretaker or income.

$1,799,900
Key West
Gg Watson Subdivision   - MM: 1.00
3 Bed, 3 Baths, 1,572 SqFt Days Listed: 91
-7.65% ($149,100) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Essentially a Brand-New Home at an Unbeatable Price Per Square Foot!Nestled in the coveted X flood zone, this historic Key West gem has been completely reimagined from the inside out. With all-new plumbing, electrical, roof, and impact-resistant windows, this property offers the charm of the past with the peace of mind of modern construction.Step beyond the charming Caribbean gate and into a private oasis designed for relaxation. Inside, a modern organic aesthetic blends effortlessly with coastal elegance. The original Dade County pine exposed beam ceiling adds warmth and character, while a natural palette of recycled glass lighting, oak floors, Calacatta marble baths, and European quartz countertops creates a serene, upscale ambiance.Perfect for intimate gatherings, the spacious kitchen bar overlooks a heated and chilled Zen pool with a tranquil waterfall feature. The entertainment space transitions seamlessly to an expansive patio framed by lush greenery, including a mature Ruby Red mango tree--a true tropical retreat.Designed for comfort and privacy, the oversized first-floor primary suite is a luxurious escape with a spa-like bath. Upstairs, two guest bedrooms feature ensuite baths, while a main-floor half bath adds convenience. The home also offers ample storage and dedicated office space for two desktops.With a monthly rental license, this property is an ideal investment or vacation retreat, positioned just moments from Key Wests top attractions. Parking is available right out front.Schedule your private showing today to fully appreciate the exceptional details and craftsmanship that make this home truly one of a kind.

$1,799,000
Key West
Key West Realty Cos Subdivisi   - MM: 3.00
4 Bed, 4 Baths, 1,912 SqFt Days Listed: 9
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Spacious Mid-town Retreat with Mother in Law Cottage.Welcome to your beautifully, renovated midtown Oasis, designed with comfort, convenience and versatility in mind. Enviable one level living offers an excellent layout for a growing family r multigenerational living. 4BD/3.5 BA with the flexible floor plan and stunning updates throughout. At the heart of the home, the newly renovated kitchen is thoughtfully designed with everyday functionality. A large central Island invites gatherings and conversations surrounded by custom cabinetry, gleaming granite countertops and a high end appliance package. Rays of sunshine filter through multiple windows create a bright and welcoming space perfect for those casual mornings and lively evenings.Enjoy multiple outdoor gathering areas perfect for the weekend BBQ and large family gatherings.Bask in all day sunshine and savor the warm tropical breezes and cool off in the crystal clear pool.Generous lot provides lots of room for Multiple vehicles as well as off street parking for your Golf Cart.Tucked away in the rear of the property is a fully equipped Mother In Law apartment, featuring a kitchenette, living room and full bath.An additional Studio is also located adjacent to the pool and would be an ideal home office, studio or wellness space.Located just minutes from the shops, dining and schools, this home offers a peaceful setting in a residential neighborhood.Whether you are seeking to spread out, need space for a growing family or a smart investment, this home will not disappoint.

$1,799,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,392 SqFt Days Listed: 112
-5.27% ($100,000) 1 Price Change : Last Change 67 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to this captivating historic Conch home, where the essence of Key West island luxury comes alive. This charming residence boasts a classic front porch that beckons you to sit back and enjoy the tropical breeze, making it an ideal space for leisurely mornings or cozy evenings. Upon entering, you are greeted by a sun-drenched interior adorned with Dade County pine hardwood flooring and high ceilings that create an inviting and spacious atmosphere, perfect for both relaxation and entertaining.The heart of this home lies in its kitchen, a culinary haven equipped with stainless steel appliances, 6 burner Viking stove top, pantry space, and a comfortable seating area. The open design allows for seamless flow from the kitchen to the back patio, making it effortless to host gatherings or enjoy quiet family meals by the pool. Step outside to discover a relaxing pool area, complete with an air-conditioned poolside guest cabana. This versatile space features a wet bar and a cozy seating area that easily transforms into a pull-out sofa bed, ideal for hosting friends and family or enjoying a peaceful afternoon by the pool. Ascend to the second floor to find a striking stained glass window that adds a touch of elegance to your arrival. Here, youll discover a generous master suite, boasting cathedral ceilings and an abundance of closet space, creating a serene retreat. Additionally, a bonus room is currently set up as a home office, providing flexibility for your lifestyle needs. A delightful guest bedroom completes this level, featuring access to a private rooftop terrace that overlooks the inviting pool, perfect for unwinding at sunset or enjoying morning coffee in solitude. This historic Conch home is not just a residence; it is a lifestyle, offering a harmonious blend of modern conveniences and timeless charm. With its ideal location, you are just moments away from all that Key West has to offer--vibrant nightlife, exquisite dining, and stunning beaches.

$1,795,000
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 1,622 SqFt Days Listed: 64
-5.28% ($100,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Nestled on a picturesque street in the heart of Old Town, this enchanting 2BD/3BA Historic residence offers the perfect blend of Old World charm and modern convenience. Currently operating as a successful monthly vacation rental, this exceptional home offers the perfect blend of personal retreat and prime investment opportunity. Situated in one of the most coveted areas of the historic seaport, this residence is rich in character, featuring timeless Dade County Pine walls throughout. The spacious and inviting layout is ideal for entertaining, with multiple living areas designed for gathering with family and friends. The well-appointed kitchen features granite countertops, stainless steel appliances, and stylish cabinetry, offering both functionality and a touch of modern convenience. One of the highlights of the home is the expansive primary suite featuring ample space, abundant natural light, and an en-suite bathroom. Step outside to a charming covered patio just off the dining room, with additional side space perfect for storing bikes, kayaks, or beach essentials. Designed for effortless living, the low-maintenance outdoor space ensures more time to enjoy the island lifestyle. Unwind on the delightful front porch, where you can relax in a rocking chair and savor the coastal breeze, or retreat to the upstairs balcony to greet the day with a breathtaking sunrise. This home is a rare opportunity to own a piece of Key West history while enjoying the comforts of modern living.

$1,795,000
Key West
Old Town Unlisted   - MM: 1.00
2 Bed, 2 Baths, 1,055 SqFt Days Listed: 3
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Charming Old Town Key West Retreat on Solaris Hill.Experience island living in this beautifully maintained 2-bedroom, 2-bath home atop historic Solaris Hill--the highest point in Key West. With 1,055 square feet of light-filled living space, this home blends classic Key West character with modern updates. Enjoy an open layout, high ceilings, and a bright kitchen perfect for entertaining. Step outside to your private backyard oasis, complete with a sparkling pool and lush tropical landscaping--ideal for relaxing or hosting friends.Located just steps from Duval Street, galleries, and dining, this home offers the ultimate Old Town lifestyle--perfect as a full-time residence, vacation getaway, or investment.Great Vacation Rental History.

$1,790,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 1,680 SqFt Days Listed: 126
-8.21% ($160,000) 1 Price Change : Last Change 93 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to 613 Olivia Street, a charming single-family home nestled in the heart of Old Town, Key West. Built in 1933, and located in the X Flood Zone, this historic residence offers 1,680 square feet of living space on two floors and on a 3,240 square foot lot. This property has been owner occupied for over 30 years. First time on the market in generations. Here is your chance to have that location, location, location home in Historic Old Town Key West.With a white picket fence and spacious front porch framed by stately palm trees, this home features four (4) bedrooms and one and a half (1.5) bathrooms. Its classic architecture, which includes custom crown moulding and Dade County Pine walls, reflects the rich heritage of Key West.Enter the home into the light-filled living room, which connects to the spacious kitchen with vaulted ceilings and wall-to-wall sliders leading to the private and fenced-in backyard. Two bedrooms on the ground floor and two on the second floor. There is also an unused cistern pool in the backyard, with a concrete pad that once was a second structure. The creative possibilities for this home are endless, just steps away from the vibrant culture, dining, and entertainment that Old Town Key West is renowned for. Embrace the potential of this historic gem and envision the possibilities that await at 613 Olivia Street.

$1,750,000
Key West
Old Town Unrecord   - MM: 1.00
3 Bed, 3 Baths, 1,690 SqFt Days Listed: 42
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This Conch House is filled with Key West Charm that all starts with the covered front porch perfect for relaxing. Entertain with ease in todays kitchen with its marble countertops, stainless steel appliances, and farmers sink. The open dining and living room continue to flow through French Doors to the outdoor living area with a private wraparound porch, sun deck, and heated dipping pool. A bedroom and full bathroom are on the main level offering one story living. Two large bright and airy bedrooms with vaulted ceilings and a bath are upstairs. Bahama hurricane shutters, metal roof, storage inside and outside, off-street parking.

$1,750,000
Key West
Old Town Unlisted   - MM: 1.00
3 Bed, 3 Baths, 1,440 SqFt Days Listed: 128
-2.72% ($49,000) 1 Price Change : Last Change 71 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Welcome to 205 Virginia Street, a meticulously crafted single-family home nestled in the heart of Old Town Key West. Built in 2019, this residence seamlessly blends the historic charm of the area with modern construction standards. As you step inside, youll be greeted by an open and inviting living space adorned with wood floors and bathed in natural light. The gourmet kitchen boasts quartz countertops and a high-end stainless steel appliance package, catering to both culinary enthusiasts and those who appreciate quality craftsmanship. The home offers three bedrooms and two and a half bathrooms. The large primary suite possesses an enormous covered deck and beautiful ensuite. The second bedroom features a private balcony and custom-built shelving, providing ample storage and display options. The third bedroom may also be configured as a formal dining room, perfect for entertaining guests. Venture outside to discover your private island oasis. The heated pool, complemented by a soothing waterfall, invites relaxation year round. Surrounded by lush tropical landscaping, brick walkways, a classic picket fence, and coveted parking spot, the outdoor space is designed for both tranquility and entertainment. Covered porches on both levels, front and back, offer serene spots to enjoy the balmy Key West evenings. Constructed with durability in mind, the home is built to withstand 180 mph hurricane winds and features impact windows and doors with concrete siding, providing peace of mind and low insurance rates. Location is paramount, and 205 Virginia Street does not disappoint. Situated just a few blocks from the vibrant Duval Street, youre within walking distance to an array of restaurants, entertainment venues, and the rich cultural experiences that Key West offers. Despite its proximity to the lively downtown, the property is tucked away in a peaceful neighborhood, offering the best of both worlds. Experience the perfect charm and modern luxury at 205 Virginia Street.

$1,750,000
Key West
Old Town Unrecord   - MM: 1.00
2 Bed, 2 Baths, 759 SqFt Days Listed: 131
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Discover your dream surfers cottage on a tropical island! Built in 1918, this charming home still showcases elements of its historic architecture, blending timeless character with a unique coastal vibe. Located at 1020 Fleming Street in the Historic Seaport area of Old Town Key West, youll be just a short walk from amazing restaurants, great bars, and some of the best fishing and diving charters in the world.This rare gem has not been available on the market for nearly two decades and appears on the Key West map of 1848--dont miss the opportunity to make it yours. Start living your dream today. Call now!

$1,749,000
Key West
Monroe Investement Co Subdivi   - MM: 2.00
3 Bed, 3 Baths, 1,785 SqFt Days Listed: 28
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Visualize yourself at this peaceful tropical residence, situated on a sprawling corner lot, enveloped by lush mature foliage. As you approach the front door, youll be greeted with a variety of native and exotic plants including a glorious frangipani tree at your front door. Step through the doors of the single level home to discover three bedrooms and two bathrooms, a large kitchen, open-concept living spaces, and a large den that can easily be converted into a fourth bedroom, or home office. The home features a ceramic microbead roof overlay for energy efficiency, central air, and hurricane shutters. The expansive backyard contains an off-street parking space suitable for an RV, as well as ample space for a pool along with an abundance of mature landscaping. Ideally located just minutes from the beaches, vibrant entertainment district, and all the iconic attractions Key West has to offer, this corner-lot property combines convenience with potential. With generous parking and a prime location, its perfect whether youre looking to elevate the existing home or reimagine the space entirely. Versatile, full of character, and brimming with opportunity--this is a rare find in the heart of Key West.

$1,749,000
Key West
Gwynn Subdivision   - MM: 1.00
3 Bed, 3 Baths, 1,897 SqFt Days Listed: 134
-12.51% ($250,000) 2 Price Changes : Last Change 45 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Step into Key West history with a modern twist at the Kali Zoi House, a meticulously maintained gem nestled in lush tropical surroundings in Old Town Key West. Originally built in the early 1900s & updated in 1988, this fully furnished home offers nearly 1,900sqft of spacious living. Located near everything (Duval Street, beaches, etc.), this home combines historic charm with unbeatable convenience.Experience the charm of Old Town with the inviting covered front porch, an ideal spot to enjoy your morning coffee. The first floor features 3 bedrooms & 2 bathrooms. Two of the bedrooms include ensuite bathrooms, with one also offering a second entrance for guest access. The primary suite has a private exit to the backyard. Upstairs, youll find an expansive living room, dining area, & a stunning open kitchen with beautiful striped Mahogany cabinets. A third full bath completes the layout. Enjoy the island breezes from the newly redone wraparound balcony, tucked up in the treetops, offering a tranquil retreat. Unwind in the private backyard, ideal for entertaining or relaxing in the (heated or chilled) cocktail pool. The yard is fully fenced. Additional features youll love: X-Flood Zone, New Roof (2022), New Hot Water Heater, Recently Upgraded Upstairs Porches & Deck, Fully Furnished (Indoor & Outdoor): Move-In or Vacation Rental Ready!Currently part of a successful vacation rental program with a wonderful reputation, Kali Zoi House is perfect as a family getaway or a promising investment opportunity.

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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