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Big Pine Key Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Waterfront properties for sale in Big Pine Key are wonderful for Florida Keys real estate buyers who are looking for a relaxing enclave in one of the most beautiful spots in the Keys.  The key is known for its natural beauty, and purchasing a Big Pine Key waterfront home for sale is the perfect way to take advantage of this appeal.  This is the largest island in the Lower Florida Keys, with great neighborhoods including Punta Brisa, Long Beach Estates and more.  Though the key is large in land area, it is not as densely populated as other areas, creating a secluded, tranquil atmosphere.  Browse the Florida Keys MLS for all Big Pine Key waterfront home listings below.

Total Listings 42
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$500,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 654 SqFt Days Listed: 17
-4.76% ($25,000) 1 Price Change : Last Change 8 Days Ago
Half Duplex - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 37ft.Concrete

Nestled at the end of a peaceful dead-end street, this well maintained 2-bedroom, 1-bath home offers both privacy and serene water views. The property backs onto a picturesque canal that is fully maintained by the HOA, ensuring a low-maintenance outdoor lifestyle.Outside, enjoy the tranquil canal from your backyard, ideal for morning coffee or evening sunsets. Located in a family-friendly community, this home offers easy access to Bogie Channel, local amenities, parks, and the loveable Key Deer. This is a rare opportunity to own a piece of paradise and quiet waterfront living.

$647,000
Big Pine Key
Cahill Pines & Palms   - MM: 30.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 66
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

This 2-bedroom 2-bathroom 1056 SF home is in Big Pine Key. Has updated bathrooms, flooring and Stainless-steel appliances. Plenty of room to park all your vehicles, trailers, and RVs. The yard is partially fenced and perfect for your pets or kids. The home is also located on a plugged / swimming canal that is perfect for swimming, A large storage shed is located on this low maintenance property. The owner has recently added new gravel. Make this your own piece of paradise!

$675,000
Big Pine Key
Doctors Arm   - MM: 30.50
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 151
-2.88% ($20,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

Highly desirable Doctors Arm waterfront location! Great price point with excellent deep water access to both the Atlantic Ocean as well as the Gulf. Two bedroom with two full bath concrete home. Wonderful open concept, as well as a fully screened patio with built-in Bar and grill. 50ft dockage with Davits. Metal roof and new AC. Ready to move in condition.

$699,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 888 SqFt Days Listed: 232
-6.68% ($50,000) 2 Price Changes : Last Change 26 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits124ft.

*** MOTIVATED SELLER NEW METAL ROOF, NEW CENTRAL A/C ***Welcome to this waterfront paradise on Big Pine Key! Charming 2 bedroom, one-and-a half-bath, corner canal CBS home is a boaters dream, featuring two concrete docks, a generous 70 and an additional 54 complete with two davit sets for all your watercraft needs. A total of 270 of canal front, situated on a fenced 15,045 square foot lot. This fully furnished property offers the perfect blend of privacy and convenience. Kitchen credit offered. Close to shopping and dining yet a very private location. The nearby bridge has a clearance of 7 feet. Excellent boating to Bogie Channel. Lot can be subdivided. Owner financing considered with a large down payment. Big Pine Key where time truly moves slower.

$719,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,353 SqFt Days Listed: 344
-7.70% ($60,000) 3 Price Changes : Last Change 80 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

This 3BR spacious canal front home with quick open water access is nestled at the end of a quiet dead-end street. Amidst lush vegetation, this property offers the ultimate sanctuary for those seeking privacy and a connection to the Keys lifestyle. 50ft concrete seawall with 10,000lb boat lift. This home boasts an inviting shaded deck creating the perfect outdoor space for relaxation and entertainment. The homes interior layout boasts almost 1400sqft, including 3 spacious bedrooms, 2 bathrooms, and a bonus room that could be used as an office, workout area, or Florida room. 30AMP hook up.

$729,000
Big Pine Key
Cahill Pines & Palms   - MM: 30.00
3 Bed, 3 Baths, 1,474 SqFt Days Listed: 226
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davit Pads60ft.

BACK ON THE MARKET, seller financing fell through. 3 bedrooms, 2 bath home on a 75-ft-wide plugged canal. Updated kitchen with stainless steel appliances and tons of cabinet space plus a separate dining area. Cathedral ceilings in the spacious family room with an adjacent sunroom. Master bedroom has cathedral ceilings, solid oak floors and custom built-ins. The huge en suite bath is a spa-like oasis featuring a separate shower and tub for soaking. Two additional bedrooms and a second full bathroom. Fully enclosed two car garage which also provides an abondance of additional storage with built-in shelving. Spacious fully fenced backyard, second-floor rear deck which overlooks the canal.

$734,900
Big Pine Key
Port Pine Heights   - MM: 29.00
3 Bed, 3 Baths, 1,443 SqFt Days Listed: 165
-13.44% ($114,100) 6 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Motivated Seller! Enhance your lifestyle with this serene 3-bedroom, 2-bath canal-front oasis nestled in the tranquil Port Pine Heights subdivision of Big Pine Key. Revel in the quietude of your private retreat, with unobstructed views of the majestic Great White Heron Refuge. This home is a sanctuary amid the natural splendor of the Key Deer Refuge, truly a haven for those who cherish the great outdoors.Your personal concrete dock beckons, promising swift access to the Gulf and Atlantics most coveted fishing locales and idyllic back country sandbars, just a stones throw from your doorstep. Venture out on the water from the convenience of your backyard, or simply relax and soak in the panoramic vistas from your expansive covered decks--a prime spot for entertaining or quiet reflection.Inside, discover a spacious, sunlight-filled living room that flows effortlessly into a well-appointed kitchen and dining area. The vast bedrooms offer comfort and a peaceful nights rest for family and guests alike, the primary bedroom has its own exterior entrance and would make a great mother-in-law suite. Delight in the vibrant local art murals that infuse a touch of Key West charm throughout your abode.Function meets form with a generous storage workshop perfect for the avid fisherman or hobbyist, complete with a resilient metal roof and impact windows for peace of mind. This lovingly maintained property is more than just a home--its a lifestyle, waiting to be embraced by those looking to create lasting memories in the Florida Keys. Easy to show!

$765,000
Big Pine Key
Doctors Arm   - MM: 30.50
2 Bed, 2 Baths, 1,034 SqFt Days Listed: 217
-9.89% ($84,000) 3 Price Changes : Last Change 79 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

2.25% Assumable VA loan. Welcome to this enchanting 2-bedroom, 1.5-bathroom property nestled in the tranquil neighborhood of Doctors Arm. With a serene ambiance and wildlife views, this home offers the perfect blend of comfort and relaxation.Situated along a picturesque boating canal, residents can enjoy seamless access to the pristine waters, ideal for boating enthusiasts and nature lovers alike. Adding to the allure, the county-owned land across the canal ensures privacy and a sense of exclusivity.Step inside to discover a newly renovated kitchen adorned with sleek stainless-steel appliances, complemented by new bamboo wood flooring that exudes modern elegance. The interior has been freshly painted, creating a bright and inviting atmosphere throughout. Vaulted wood ceilings add a touch of rustic charm, enhancing the overall character of the home.The property features new trex decking and steps, as well as freshly upgraded porch flooring, perfect for outdoor entertaining or simply unwinding amidst the serene surroundings. Additionally, a screened-in porch provides a cozy retreat where you can enjoy the gentle breeze keeping you safe from insects.Equipped with a solar panel system, this home offers eco-friendly living and significant savings on energy bills. Ample storage space downstairs ensures organizational convenience, while the surrounding wooded lots provide a sense of seclusion and tranquility.With easy access to Bogie Channel, this residence promises a lifestyle of convenience and leisure, making it an idyllic retreat for those seeking a peaceful waterfront haven. Dont miss the opportunity to make this captivating property your own!

$770,000
Big Pine Key
Cahill Pines & Palms   - MM: 30.00
2 Bed, 2 Baths, 960 SqFt Days Listed: 152
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Lots of Room To Roam! Own your own compound with this triple lot home. Centrally located between Marathon and Key West for easy access to shopping and dining. This home has so many possibilities to add a pool, gardens, a Tiki bar or anything that you can imagine. Plenty of room to park all of your vehicles, trailers, and RVs. The yard is fenced in with a grass lawn perfect for your pets or kids. The home is also located on a plugged / swimming canal that is perfect for swimming, kayaking or paddle boarding. There is a concrete seawall complete with an outside bar / grill area that is perfect for entertaining. The home offers an open living concept complete with vaulted ceilings and wrap around deck areas. The property also has a cistern that is currently used for irrigation. This home has it all! Priced to sell. Make this your own piece of paradise!

$775,000
Big Pine Key
Tropical Bay   - MM: 30.50
1 Bed, 1 Baths, 1,008 SqFt Days Listed: 148
-6.06% ($50,000) 2 Price Changes : Last Change 23 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 one bedroom one bath cottage offers a tranquil escape on a double lot with its fenced in yard, 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. Easy, to make the house a 2 bedroom home. 188 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.

$779,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,039 SqFt Days Listed: 282
-2.50% ($20,000) 1 Price Change : Last Change 49 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Pleasant 3 bedroom waterfront home located in Eden Pines Colony. Such a lovely family neighborhood where you can experience the natural beauty and wildlife. This home truly shows well and has gone through recent upgrades such as new flooring, bathroom vanities, new kitchen appliances, and hot water heater. For storm protection and lower insurance rates, house is outfitted with impact windows/doors and has a metal roof (2018). Main living area and kitchen is open concept, which is great for entertainment/family gatherings. Off main the living area you have french doors that lead to your private deck where you can relax and enjoy the island breeze. Exterior of property offers dockage to accommodate a boat and the downstairs unit is a bonus space for workshop and storage. Within minutes away is a neighborhood boat ramp, dog park, grocery store, and restaurants. Do not miss your chance to get this delightful property, located in a relaxed yet festive neighborhood!

$799,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 2
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

**Open House Saturday 11:00am-2:00pm**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!

$815,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 960 SqFt Days Listed: 208
-5.12% ($44,000) 2 Price Changes : Last Change 5 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Slip60ft

Truly a spectacular property in Eden Pines Colony. Move-in ready home on a double lot, with excellent boat dockage. This property is fully fenced and well manicured with mature landscaping. Great space for pets to roam and has plenty of room for a future pool. Make this your own tropical sanctuary! Interior of home is bright and inviting. Open concept living with vaulted ceilings, and shows extremely well. The kitchen boast a large island and has plenty of cabinet space for storage. No need to struggle to find room for flatware, dishes, and food. Additional upgrades include soft close cabinets, farm sink, and gorgeous quartz countertops. Both bathrooms are updated and off main living are two sets of sliders to access your screened in back porch. This is your spot for easy indoor outdoor living. Picture your morning coffee or evening dinners here. Porch set up includes a bluetooth speaker system where you jam to your favorite tunes while taking in the island breeze. What a great home for the family or to host gatherings. Boat dockage includes a 60ft concrete seawall with davits. Plus! A boat cut-in where you can dock an additional vessel. And after your long boat days you can rinse off in your private outdoor shower. On the ground level is an enclosure where you can make a workshop or use for storage space. Other features include tankless water heater, plantation shutters, and composite stairs. Within minutes is neighborhood boat ramp, local grocery, shopping, dog park, walking trails, and food/beverage. So much to offer with this one!

$869,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,152 SqFt Days Listed: 183
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Two Car Garage, Impact Windows, Low Insurances. Welcome to paradise in the serene Eden Pines neighborhood of Big Pine Key, FL. Presenting 29207 Cypress Dr, a charming waterfront retreat offering the epitome of Florida Keys living.This home boasts 3 bedrooms and 2 bathrooms, providing ample space for comfortable living. The open floor plan seamlessly connects the living, dining, and kitchen areas, ideal for both relaxing evenings and entertaining guests.Venture outside to your own private oasis, where a spacious screened in deck overlooks the tranquil canal. Spend your days lounging or fishing off the seawall or exploring the nearby mangroves by kayak. With direct access to the Ocean or the Golf this property is a boaters dream come true.Conveniently located just minutes from shops, restaurants, and attractions, yet nestled in a quiet and peaceful neighborhood, this home truly offers the best of both worlds.Dont miss out on the chance to own a slice of paradise in the Florida Keys. Schedule your private tour today.

$899,000
Big Pine Key
Port Pine Heights   - MM: 29.00
3 Bed, 3 Baths, 1,224 SqFt Days Listed: 38
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 12ft.

Tranquil Canal-Front Home in Big Pine Key, FLEscape to your own piece of paradise with this stunning 3-bedroom, 3-bathroom home, perfectly positioned on a peaceful canal in Big Pine Key. This residence offers a rare combination of serene living and modern comfort, surrounded by the natural beauty of the Florida Keys.Spacious Living Area: The open-concept living space is bright and airy, featuring high ceilings and large windows that frame beautiful canal views. Kitchen offers stainless steel appliances, granite countertops, and plenty of cabinet space.The master suite is a private retreat with an en-suite bathroom and direct access to the balcony. Two additional bedrooms provide comfort and privacy for family or guests. Step outside to your expansive deck, explore tranquil nature paths that wind through the property, or launch your boat from your private 12 ft dock with large patio.This home is an ideal sanctuary for nature lovers.Port Pine Heights Park: Just a short stroll away, enjoy the serene Port Pine Heights Park, a perfect spot to unwind and take in the tranquil sunsets.Nestled in a quiet neighborhood, this home is close to local amenities, parks, and some of the best fishing spots in the Florida Keys, while still offering the peace and tranquility you desire.Dont miss the chance to own this canal-front gem in a prime location!

$949,000
Big Pine Key
Whispering Pines   - MM: 30.50
3 Bed, 3 Baths, 1,200 SqFt Days Listed: 31
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits75ft.

Escape to paradise in this cozy 3-bedroom, 1-bathroom newly updated with a brand-new metal roof and a modern kitchen. Located in a tranquil setting in the Florida Keys, this home offers a blend of comfort and style with stunning water views. Perfect for families, couples, or small groups looking for a unique and relaxing getaway.**Features:**- **Open Living Area:** Spacious living room with large windows that fill the space with natural light and offer breathtaking ocean views.Brand-New Kitchen:** Recently renovated with sleek cabinetry, stainless steel appliances, and granite countertops - ideal for home cooking and entertaining.Comfortable Bedrooms:** Three well-appointed bedrooms.75-Foot Dock:** Direct access to the ocean for boating, fishing, or simply enjoying the sunset from your private dock.Enjoy the large deck, perfect for grilling, lounging, or dining under the stars.Prime Location: Close to local attractions, dining, and shops. Explore nearby Key West, Bahia Honda State Park, and the best the Keys have to offer.

$985,000
Big Pine Key
Port Pine Heights   - MM: 29.00
3 Bed, 3 Baths, 1,353 SqFt Days Listed: 50
-10.45% ($115,000) 1 Price Change : Last Change 23 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift70ft.Concre

Immaculately-maintained Port Pine Heights retreat, boasting no-bridge Open Water Access and spacious floor plan! Nestled within a peaceful, established neighborhood, this gorgeous 3-bed, 2-bath slice of paradise offers a bright and welcoming main living space, ideal for entertaining. The great room provides loads of natural light and a large kitchen, equipped for all culinary pursuits with sleek stainless-steel appliances, abundant wood cabinetry and prep space, and generous pantry. Impact sliding glass doors lead out to a screened-in, covered veranda, surrounded by nature. Two guest bedrooms come outfitted with large closets, while the primary suite offers sizable dual closets, en suite bathroom, and patio access. Additional interior features include a convenient laundry closet, with central vacuum, sky lights, impact doors/windows throughout, and High Efficiency Whole Home Air Cleaner. Enjoy easy and frequent boating from the convenience of your own back yard; this anglers paradise features a full-length, 70 concrete seawall with 10K boat lift, 1K lift, floating dock, step down, fillet station, water, solar lights, and swim ladder. Rinse off after a day on the water in the outdoor shower, and grill up your fresh catch in the shade of the massive covered patio, which comes equipped with sliding screens for enjoying the prevailing sea breezes, while keeping insects at bay! Keep tools and equipment dry and secure in a convenient downstairs storage space. Additional features include RV hookup and 200-amp service for the home. The property also utilizes a catchment system which collects rain water for a variety of conveniences. The lushly landscaped lot is beautifully manicured, partially fenced, and incredibly serene and private. Plenty of parking with generous carport, and additional open parking for vehicles or trailer storage, this spectacular Big Pine Key sanctuary is supplied with every convenience in mind!

$985,000
Big Pine Key
Doctors Arm   - MM: 30.50
3 Bed, 3 Baths, 1,572 SqFt Days Listed: 113
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits60ft.

ENJOY GREAT BOATING and the peaceful nature that Big Pine Key offers in this desirable section of Doctors Arm. The 40 ft. wide, flow-through canal provides excellent access to Bogie Channel, the Atlantic and back country. Youll find so much character in this 3BD/2.5BA,1572 sq. ft. home with the multiple porches and levels - one step inside and youll be greeted by the soaring ceiling, an inviting window seat and the wood-burning fireplace surrounded by a natural cedar wall. The master bedroom with ensuite bath and private porch are located on the main living level, and upstairs youll find 2 more bedrooms, a full bath, and access to the L-shaped upper story deck from which to enjoy panoramic views and stargazing. The ground level has two separate storage rooms for your toys, fishing gear, dive equipment and more. 6,000 sq. ft. lot has a fully-fenced back yard, 60 ft. wood dock with davits and a terrific, covered fish-cleaning station. Features include metal roof (2009), impact-resistant skylights, impact-resistant fixed windows, accordion shutters; some exterior walls are Hardie-board, and some are cedar. If youve been searching for a home thats unlike the rest, in an area where one can enjoy nature, this is it!

$999,000
Big Pine Key
Whispering Pines   - MM: 30.50
3 Bed, 3 Baths, 2,448 SqFt Days Listed: 134
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip75ft.Cut/Na

Prime Boating Access and Dockage comes with a slice of paradise. Delightful Old Florida Keys cottage perfect for boating enthusiasts and gardeners. Nestled in a serene area characterized by spacious half-acre homesites, this property offers both tranquility and potential. Property Highlights include*Prime Boating Access: Enjoy a covered cut-in boat slip, making this an ideal spot for boating and water adventures.*Spacious Lot: Set on a generous 1/2 acre lot, providing ample space for adding a pool or further landscaping.*Outdoor Living: A wide screened-in porch offers the perfect setting for alfresco dining and enjoying the serene surroundings.* Privacy and Security: The property is fenced and thoughtfully landscaped to ensure privacy and keep the charming Key Deer at bay.Potential for Personalization: With a little TLC, this cottage can be transformed into your perfect Keys hideaway.Recent Upgrades include the newer roof adding to the propertys appeal and longevity.Escape to a quiet oasis where you can relax, entertain, and enjoy the natural beauty of the Florida Keys. With its great potential and idyllic setting, this cottage is ready to become your dream retreat. Dont miss this unique opportunity to create your own private paradise 20 miles from Key West or Marathon.

$1,035,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,456 SqFt Days Listed: 16
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

Situated on a lushly landscaped double lot on a canal, this two-story stilt home has ample space for all your extras including parking for your trailer and RV, and room for a pool. 60-foot concrete seawall with davits plus additional 60 feet of seawall lets you get out to the reef or the backcountry with ease. Upgrades to this 3-bedroom/2-bath home include brand-new metal roof (completed 9/24); Hardie Board siding; beautiful engineered hardwood flooring throughout; and mosaic tile marble floors and marble walls in both full baths. Mahogany French doors in living area and bedroom, mahogany trim around windows, and a mahogany staircase on first story add warmth and character to this spacious 1,456-square-foot home. Walk-in closet and soaker tub in primary suite. Gorgeous glass-door kitchen cabinets, Shaws Original farm sink, and premium quality granite make the kitchen an exquisite room, with all stainless steel appliances. A screened patio off the living room is surrounded by lush tropical landscaping and provides a view below where you can often see Key Deer. Downstairs enclosure and garage offer plenty of extra room, and just outside them theres yet another place to grill, relax and watch the wildlife including manatees in the canal seasonally. Whole-house shutters. One lot of the double-lot is fenced. Restrictive covenant-no additional residences may be built on property. Shown by appointment.

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 10-04-2024.
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