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

Total Listings 265
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$1,399,000
Big Pine Key
Pine Channel Estates   - MM: 29.50
2 Bed, 2 Baths, 1,024 SqFt Days Listed: 47
-1.82% ($26,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits75ft.Concrete

Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads directly to the water, offering easy access for boating and water activities. Whether youre a seasoned boater or a weekend enthusiast, this canal-front location provides fantastic opportunities for adventure right at your doorstep.The property offers plenty of storage space, ensuring room for all your gear and toys. Theres even space to add a pool for those sunny Florida days. A garage adds to the convenience, making this home both functional and full of potential.Dont miss the chance to own this piece of paradise, where comfort, coastal living, and a vibrant island lifestyle meet.

$1,399,999
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,360 SqFt Days Listed: 33
-3.38% ($49,001) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift50ft

Welcome to Keys Life Getaway! Located in the desirable Tavernier neighborhood of Plantation Key Colony, this fully furnished 3 bedroom, 3 bathroom concrete canal home is awaiting your arrival. Watch the manatees play and the tarpon roll right off your dock. Situated on a deep water canal, youll enjoy quick access to Florida Bay or the ocean via Tavernier Creek and convenient boat fuel at the end of your canal. Inside, the home features a great floorplan for entertaining, tile floors throughout, a well appointed kitchen with plenty of storage, stainless steel appliances and a separate wine fridge. The exterior features low maintenance landscaping, a 15,000lb boat lift, jet ski davit and a storage shed. The neighborhood features a wonderful bayfront homeowners park where you can launch your boat or relax and watch the sunset! The boat ramp was recently renovated and features a new concrete ramp and dock. Optional membership to the homeowners park is $200/year. The home is conveniently located near Coral Shores High School, Plantation Key Elementary School, shopping, grocery, bars & restaurants. This home will make a great full-time residence, or 2nd home with the ability to generate vacation rental income.

$1,425,000
Key Largo
Cross Key Waterways   - MM: 103.00
5 Bed, 5 Baths, 2,027 SqFt Days Listed: 50
-8.06% ($125,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Amazing Three-Story Waterfront Haven in Cross Key Waterways, KEY LARGO! Embrace the allure of coastal living in this impressive 5-bedroom, 4-bathroom Key Largo retreat. This waterfront charm provides abundant living space for you and your loved ones with large open balconies off each floor. This property have a 40-foot dock, and a 15,000-pound lift that effortlessly hoists your vessel. The loft space awaits--a canvas of possibilities for a home office, entertainment area, or even a tranquil retreat with captivating views. This property can be rented for a mininum of 28 days. Only one hour away from Miami. Call today.

$1,439,000
Sugarloaf Key
Gulf Shores   - MM: 19.50
4 Bed, 4 Baths, 2,464 SqFt Days Listed: 281
-12.73% ($210,000) 7 Price Changes : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp25ft.Concre

Price Drop!! Extremely Motivated Sellers!! Your Sugarloaf Key Sanctuary!! Brand new tile flooring installed throughout the entire home (Nov 2024). Three separate walk-in closets. A Must See to appreciate the size of home and lot!! This spacious 6,376 gross sq ft, 4 bedroom, 3 full bath, 12 stilted, canal-front home was custom built in 2017 by Palm Harbor Homes. The home features a 1,256 sq ft wrap-around porch with entertainment space overlooking the canal along with large entertainment areas. The home is in a quiet, desirable neighborhood with a private boat ramp and seawall on a free flowing canal with access to the Gulf and the Atlantic Ocean. It is on a double lot (2 150x100 lots) consisting of 30,000 sq ft with an oversized fenced backyard with mature landscaping to include mango, avocado and the largest neem tree in the Florida Keys. Plenty of room for a pool! The interior of the home features an open floor plan with oversized bedrooms and baths totaling over 2,464 sq ft of finished living space. The large kitchen highlights stainless steel appliances and an abundance of cabinets and counter space and the master bedroom features a large walk- in closet and a retreat with views overlooking the canal. This newly built home features tall concrete pilings, hardie-board siding, metal roof and impact windows with massive amounts of storage space both upstairs and down. Plenty of room for parking your vehicles, RV, boat, airplane and guests!

$1,450,000
Big Pine Key
Tropical Bay   - MM: 30.50
3 Bed, 3 Baths, 2,068 SqFt Days Listed: 112
-3.27% ($49,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

Enjoy absolutely stunning open water views and spectacular sunrises every morning from this gorgeous open waterfront property in Tropical Bay Estates. This spacious 3-bedroom, 2-bath home was completely remodeled in 2020 with beautiful finishes throughout. Enjoy a chefs kitchen, with top of the line appliances, and an abundance of cabinets and counter space, ideal for entertaining. Flooded with natural light, this gorgeous layout was designed to capture breathtaking views of the open water from every angle in the main living area, a tranquil backdrop, perfect for any occasion. Enjoy peace of mind with all new plumbing and all new updated electrical throughout. The concrete block construction with impact windows, metal roof, and foamed roof deck insulation, make this home an absolute fortress. Situated on Bogie Channel with excellent boating access to both the Atlantic and Gulf where you can enjoy world class fishing and diving in only a short run. You are also just around the bend by boat or car, from Bahia Honda State Park voted one of the best beaches in the U.S by Trip Advisor.

$1,475,000
Key Haven
Key Haven 3rd Add   - MM: 5.00
2 Bed, 2 Baths, 941 SqFt Days Listed: 58
-3.28% ($50,000) 1 Price Change : Last Change 29 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.Concrete

This fully upgraded 2 bedroom 1 bathroom canal front home offers open water views and deep water access. Completely renovated, plumbing, electrical, impact doors and windows, custom cabinetry in kitchen and bath, porcelain countertops and backsplash, built in closets and electric water heater. A brand-new 60 x 8 concrete seawall adds durability and value. Enjoy coastal living and island life just minutes from Key West!

$1,475,000
Big Pine Key
Hollerich Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,315 SqFt Days Listed: 26
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

***BACK UP OFFERS WELCOME!!** Views abound in this new Topsider home, surrounded by water on three sides with 110 ft. of east-facing frontage overlooking Bogie Channel providing easy access to the back country and ocean. The property has 134 ft. of frontage along the 40 ft. wide canal on south side. One step inside the 1592 sq. ft. living area and theres no denying the views! With cathedral ceilings and abundant windows throughout, its light and bright inside. The great room opens to the east-facing deck from which to watch the sunrises or moonrises and feel the tropical breezes. Offering 3 bedrooms and 2 baths, the split-bedroom floor plan has an elevator that opens opposite the kitchen island; the well planned kitchen features wood cabinets and stunning granite counters. Located close the community park for easy access to amenities for all ages including tennis courts, bocce, playground, skate park, the community center, picnic pavilions, and much more. Impact-resistant windows and doors, metal roof, Hardie-board siding. The Certificate of Occupancy was issued on 3/7/2025, replacing an older home that was previously onsite. Note: the concrete dock/seawall is in disrepair and will convey As-Is.

$1,490,000
Key Largo
Key Largo Trailer Village   - MM: 101.50
3 Bed, 3 Baths, 1,500 SqFt Days Listed: 68
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift45ft.

Experience the ultimate Florida Keys lifestyle in this beautifully maintained waterfront home situated in Key Largo, offering sunset views over the Florida Bay. This solid concrete home features a metal roof, impact windows and doors, and a spacious open-concept living area with 3 bedrooms and 2 bathrooms, this home is designed for comfort and coastal elegance.Step outside to a low maintenance yard and enjoy 45 of deep-water concrete dockage, complete with a 10,000lb boat lift. Additional features include a spacious storage/workshop, covered parking, newer Rudd central a/c, premium tinting on all the windows and a fully fenced yard.Enjoy direct Florida Bay access with nearby Atlantic Ocean access for world-class offshore fishing. As part of the HOA, youll have access to two private boat ramp parks--one featuring a sandy beach and swimming area. Whether youre fishing, boating, or dining at nearby waterfront restaurants, this home is a perfect island retreat.This is an opportunity to embrace the Florida Keys lifestyle--boating, fishing, and sunsets right from your backyard!

$1,499,000
Key Largo
Twin Lakes   - MM: 103.00
4 Bed, 4 Baths, 1,646 SqFt Days Listed: 136
-6.25% ($100,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Paradise found in this waterfront concrete home with an excellent Key Largo location! Located just a few homes in from the open bay, and very close to the Adams Cut Waterway, allowing fast ocean and bay access. Upstairs is a wide open concept floor plan, sit up bar, kitchen with pantry, vaulted tongue and groove ceilings, tiled floors, 3 bedrooms and 2 bathrooms, and an expansive screen porch. Downstairs is a large covered entertainment area with barbeque, commercial ice machine, bar and seating area, a full garage and a 1 bedroom 1 bath apartment with separate entry. The large dock has 75 feet on the water, a new 17,000 pound boat lift, a hot tub spa, and room for a generous sized pool. The deep water canal is 60 feet wide. Adams drive is being renewed and repaved to raise the street and work is well under way! Completion should be early in the year. 1 hour to Miami International airport and yet a tropical world away!

$1,499,000
Marathon
Venice   - MM: 52.00
3 Bed, 3 Baths, 1,652 SqFt Days Listed: 43
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.Concre

Located in the heart of the Florida Keys, this 3-Bedroom, 2-Bathroom, 1,652 sq ft Pool home is perfectly located on a wide boating canal with direct gulf access. Enter into the Foyer where a floating staircase leads you to the bright and airy Great Room enhanced with wood floors and glass impact doors looking out to the water. The charming Kitchen features soaring wood ceilings, glass cabinetry, stainless appliances and breakfast bar that opens to the Living and Dining Areas. The main floor also hosts a full Bath and Bedroom boasting wood-beamed ceilings, wood floors and views of the water. Take the short set of stairs to the next level where you will find a 2nd Bedroom with cathedral wood ceilings and ensuite Bath. Another short set of stairs leads you to the 3rd Story which hosts a cozy loft-style Bedroom also with wood floors and soaring wood ceilings. Entertaining is a must on your waterfront lanai boasting a large heated and chilled Pool offering lots of decking and adjacent outdoor shower. The full length 60 concrete dock is enhanced with a 13,000 lb boat lift and easy Gulf Access. Storm ready with brand new impact doors and windows plus a metal roof. New ac, decking and paint. Offered Turnkey and rental ready! Garage plus lots of downstairs storage completes this tropical home.

$1,499,000
Key Largo
Pirates Cove   - MM: 98.50
3 Bed, 3 Baths, 1,106 SqFt Days Listed: 135
-7.75% ($126,000) 2 Price Changes : Last Change 30 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp100ft.Concr

Just what you have been looking for! Ground level home with amazing bay views on a spacious double lot. Double Lot Canal Front Home in Pirates Cove. Possible owner financing. Enjoy over 100 feet of dockage and stunning Florida Bay views from this beautifully updated ground-level concrete home. S3 bed 2 bath, tastefully updated inside and out. Tons of parking for Big Boats, RVs & Boat Trailers. Call today.

$1,499,000
Marathon
Woodburns Subdivision   - MM: 49.50
1 Bed, 1 Baths, 784 SqFt Days Listed: 57
-6.25% ($100,000) 1 Price Change : Last Change 14 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Waterfront Retreat with Expansive Garage, Workshop & Open Water ViewsNestled in a private, tropical setting, this stilted concrete home offers breathtaking open water views, stunning sunsets, and ultimate seclusion.Car enthusiasts and hobbyists will love the massive 3-bay garage, built in 2015, featuring 1,211 sq ft, two hydraulic car lifts, a loft, and a commercial-grade stainless steel workshop sink. This fully insulated man cave/workshop is ideal for anyone in need of a high-functioning at-home workspace or serious storage. Spray foam insulation and an on-demand hot water heater complete the setup.Room for a dock - buyer to verify. The waterfront setting offers the potential to add a dock, making it even more ideal for boating enthusiasts. Buyer to confirm and manage permitting. Fully fenced and gated for privacy, with a bonus lower-level space for guest overflow or flexible use. A rare blend of functionality and Florida Keys charm.

$1,500,000
Big Pine Key
Whispering Pines   - MM: 30.50
4 Bed, 4 Baths, 2,166 SqFt Days Listed: 68
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits60ft.Concrete

NEARLY 1/2 ACRE OF CANAL-FRONT TROPICAL PARADISE! Completely furnished, this 2,166 sf., 4-bedroom, 2.5-bath, CBS pool home is nestled on an impressive,19,762 sq. ft. double lot thats fenced and landscaped to provide maximum privacy in the yard. Boaters will appreciate 133 ft. of frontage along the 50 ft. wide canal and 25 ft. across the end of the canal; approximately 60 ft. of concrete seawall with boat davits and fish cleaning station. An inviting pool, big outdoor shower, grilling area and screened porch enhance this Keys treasure thats designed for entertaining as well as family-living. One step inside and youll instantly feel at home; the 2-story floor plan offers quiet space for everyone. Its even wired for a generator if the need arises. The desirable location provides quick boat access to Bogie Channel, its within easy walking distance of the waterfront Big Pine Community Park where youll find amenities for all ages including adult bocce, tennis, playground, community center and much more. Its also conveniently close to Overseas Highway, shopping, restaurants, banks, gas and more. Meander through the park-like setting of this truly amazing property and discover the mature vegetation, bananas, flowering shrubs, elk-horn ferns, orchids and more. Welcome to the Lower Keys!

$1,540,000
Key Largo
Key Largo Trailer Village   - MM: 101.50
3 Bed, 3 Baths, 1,296 SqFt Days Listed: 9
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift45ft.

Walk onto this almost new property. Oversized outdoor kitchen at this great location with all the entertaining furniture you need to enjoy the afternoon breeze at this private setting with family and friends. Beautiful granite counter tops on the first floor for your outdoor fun creating new memories. Twenty-thousand-pound boat lift for your large yacht. All new interior ductwork recently done. Walk upstirs into this immaculate and inviting family home with a beautiful open kitchen appealing to all chefs at this gourmet kitchen with Quartz counter tops, leading to the open living area and patio. Fully furnished with large bedrooms and well-appointed accessories for your pleasure. Blue Marble counter tops in the bathrooms for your pleasure.

$1,540,000
Big Coppitt
Similar Sound Subdivision   - MM: 10.00
3 Bed, 3 Baths, 2,069 SqFt Days Listed: 103
-2.53% ($40,000) 1 Price Change : Last Change 33 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Discover the perfect waterfront retreat in Big Coppitt Key, just minutes from Key West! This spacious 3-bedroom, 2-bathroom home offers over 2,000 sq. ft. of living space on an 8,400 sq. ft. lot surrounded by a masonry wall. Also having direct canal access makes this ideal for boaters. The thoughtfully designed split floor plan provides privacy for the primary suite, while the open living area is filled with natural light. Enjoy a sparkling in-ground pool for ultimate outdoor relaxation. Located in a great neighborhood, this home is ready for island living at its best.

$1,550,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 2,137 SqFt Days Listed: 6
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat SlipConcrete

Open Water CBS Home with Breathtaking Views!This 3-bedroom, 2.5-bath CBS home offers stunning open water views of Pine Channel and unbeatable boating access to both the Atlantic Ocean and the Gulf. Situated on a spacious 10,564 sq ft lot, the property features a concrete seawall with a cut-in boat slip, perfect for water enthusiasts.The home boasts an excellent floor plan and includes a garage with an electric door. A metal roof (installed in 2018) and newer AC system (2019) add peace of mind. While the home appears to be ground level, the elevated lot sits several feet above dock level, offering both views and protection.Ready for your personal touch--bring your creativity and make this waterfront retreat your own!

$1,590,000
Plantation Key
Plantation Key Colony   - MM: 90.00
2 Bed, 2 Baths, 1,205 SqFt Days Listed: 48
-3.64% ($60,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp

Nestled on a quiet street in the heart of Plantation Key, this one-of-a-kind canal-front home offers a picturesque retreat. As you pass through the electric gate, youll be greeted by lush foliage, vibrant blue skies, and breathtaking sunsets.This turn-key property has been thoughtfully renovated, allowing you to start enjoying your Keys lifestyle immediately. The upstairs features an inviting open-concept living area with a modern kitchen, highlighted by tongue-and-groove wood ceilings, a gas range, and a fresh renovation complete with new backsplash, cabinets, and appliances. Youll also find two bedrooms, one bathroom, and an oversized porch that provides stunning canal views.The downstairs area boasts a fully equipped 1-bedroom, 1-bathroom apartment, ideal for guests or rental income, along with a convenient garage. Enjoy outdoor meals on the covered porch or relax by the pool in the shade. For sun-seekers, the pool deck offers ample space for lounging.The private pool area is a true retreat, featuring a hammock and hot tub nestled among lush landscaping--perfect for afternoon naps or stargazing. Additional updates include a new roof, interior remodel, and AC in 2019, a new gas tank and line for the kitchen range in 2022, and a new 12 x 24 pool in 2022. The property also includes a 10,000 lb boat lift and a boat ramp that can double as storage for your flats boat.Quick trip to the Atlantic Ocean through nearby Tavernier Creek where you can enjoy world class fishing and diving, as well as the Gulf of Mexico out your back door to enjoy backcountry fishing, kayaking and paddle boarding. Enjoy cruising to several local restaurants by boat. Conveniently located to restaurants, groceries stories, fantastic schools, and hospital. Your tropical paradise awaits--come experience it today! ***BUYER TO VERIFY ALL INFORMATION.***

$1,590,000
Marathon
Venice   - MM: 52.00
4 Bed, 4 Baths, 1,744 SqFt Days Listed: 165
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Welcome to Your Dream Waterfront Retreat!Discover this charming 4-bedroom, 3-bathroom single-family home, perfectly situated on a canal front in one of Marathons most desirable neighborhoods. This spacious 1,744 sq. ft. residence features a thoughtful layout designed for both family living and vacation rental potential. Currently used as an vacation rental. Enjoy the serene canal views from your patio, and take advantage of 60 feet of dockage, making it easy to access the open waters of the Middle Keys. The home boasts all impact-resistant windows, ensuring safety and peace of mind. With a ground-level design, this property is ideal for easy living.Inside, youll find built-in cabinets and ample storage, complemented by a well-equipped kitchen featuring essential appliances like a dishwasher, microwave, range, refrigerator, and washer/dryer. The tile flooring throughout adds a touch of elegance while being easy to maintain.Located just behind the airport, this home offers convenient access to local amenities, a new bike path, and a community boat ramp, enhancing your lifestyle in the Keys. Pets are welcome, making this a perfect family residence or vacation rental opportunity.Schedule your personal/virtual walk-through today to experience the spacious floor plan and updates that make this home a true treasure. Your next adventure in the Middle Keys awaits!

$1,598,000
Marathon
Venice   - MM: 52.00
3 Bed, 3 Baths, 1,546 SqFt Days Listed: 300
-6.00% ($102,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.Cut/Na

Discover your own piece of paradise with this luxurious 3 bedroom, 2 bath waterfront home in Marathon! Completely renovated and turn-key ready, this property is currently a successful weekly vacation rental with bookings in place into 2025, making it an ideal investment opportunity.Step inside to find modern coastal furnishings, an open-concept layout, and a new kitchen with custom cabinets, granite counters, and stainless-steel appliances. The home features impact windows and doors, ample storage, and parking for cars and boat trailers. Outside, the custom-tiled backyard boasts a pool, Tiki Hut lounge, and an outdoor stainless-steel kitchen equipped with a gas grill, griddle, oven, sink, and cooler. Enjoy the landscaped surroundings and relax in the temperature-controlled pool and custom paver patio after a day on the water. Boaters will appreciate the 60ft dockage, deep water canal, quick access to both the Gulf and the Ocean, and a convenient boat lift. The property also includes a covered fish cleaning station with power, water, and light, as well as an ice maker and freezer for storing your catch.Located in a family-friendly neighborhood in the heart of Marathon, this home not only offers high-end coastal features and turn-key condition but also serves as an excellent second home or permanent residence. Owner/Agent. Dont miss out on this opportunity--schedule your showing today!

$1,599,000
Marathon
Venice   - MM: 52.00
3 Bed, 3 Baths, 1,572 SqFt Days Listed: 93
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Welcome to 2944 Dolphin Drive, a charming 3-bedroom, 2-bathroom CBS stilted home in the heart of Marathon. This property offers breathtaking open water views and a flow-through canal, making it a boaters paradise. The synthetic dock is equipped with a swim ladder, water access, and a fish cleaning station. With a double-car covered carport, a spacious pea rock yard, and plenty of parking, theres also ample room to add a pool or further customize your outdoor space.Enjoy the tranquil surroundings from the balcony, the perfect spot to relax and take in the serene canal views. Inside, the eat-in kitchen is a chefs delight, featuring stainless steel appliances, a 5-burner hooded gas stove, a kitchen island, and stylish dark wood cabinets. The large master suite includes an ensuite bathroom with dual sinks and a walk-in tiled shower with a bench, offering both comfort and elegance.Generously sized bedrooms, a convenient pantry, and additional storage under the house ensure plenty of space for all your needs. Impact windows provide peace of mind, while the open layout and functional design make this home ideal for Keys living. Whether youre enjoying the balcony, entertaining on the waterfront deck, or taking advantage of the easy water access, this property offers everything you need to live your dream lifestyle in the Florida Keys. Dont miss this incredible 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 04-22-2025.
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