316

Homes for Sale near Monroe County School District Virtual Instruction Program

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  • /23

    $599,000

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    816 South St Unit 4, Key West, FL 33040

    Life feels a little slower in the Casa Marina neighborhood. Mornings begin with a walk to Higgs Beach, afternoons are spent by the pool, and evenings often end just down the street at Salute! on the Beach or Louie's Backyard. Tucked within the peaceful Southpark Condominium community, 816 South Street, Unit 4 places you in the heart of one of Key West's most desirable locations while offering the

    Ted Stewart Truman & Co. (KW)

    816 South St Unit 4, Key West, FL 33040
  • /56

    $1,125,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    12A 12th Ave, Key West, FL 33040

    Set on 4,800 square feet with 40 feet of direct canal frontage, this three-bedroom, two-bath home was thoughtfully designed for the way people actually live in the Keys. It features ample outdoor space, multiple seating areas, and the kind of privacy that's harder to find than square footage.Ocean views from the kitchen and true indoor/ outdoor living. The master suite includes a lockout

    Krystal Thomas eXp Realty LLC Southernmost Branch

    12A 12th Ave, Key West, FL 33040
  • /40

    $625,000

    • 1 Bed
    • 1 Bath
    • 961 Sq Ft

    1901 S Roosevelt Blvd Unit 407, Key West, FL 33040

    Positioned directly across South Roosevelt Boulevard from Smathers Beach, it blends high-end modern finishes with expansive views of Key West's tranquil salt ponds. Interior highlights and upgrades include Carrara marble surfaces installed in both the kitchen and bathroom a wet bar, tiled floors flowing seamlessly throughout all living spaces, impact-resistant glass windows and doors for ultimate

    Everett Watkins Keller Williams Key West Compass Realty

    1901 S Roosevelt Blvd Unit 407, Key West, FL 33040
  • /43

    $3,500,000

    • 5 Beds
    • 4.5 Baths
    • 2,575 Sq Ft

    416 Fleming St, Key West, FL 33040

    First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless

    Robin Nilsson Keller Williams Key West Compass Realty

    416 Fleming St, Key West, FL 33040
  • /24

    $925,000

    $175K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,239 Sq Ft

    2004 Patterson Ave, Key West, FL 33040

    Well-maintained duplex offering flexible living and strong income potential in a desirable Key West location. The property features a charming 3-bedroom, 2-bath main home plus a separate 1-bedroom, 1-bath studio cottage—ideal for extended family, guests, or rental income. Both units are thoughtfully laid out with comfortable living spaces and plenty of natural light. Currently fully leased and

    Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

    2004 Patterson Ave, Key West, FL 33040
  • /40

    $2,525,000

    • 4 Beds
    • 3 Baths
    • 2,051 Sq Ft

    1427 Washington St, Key West, FL 33040

    Set on a quiet, tree-lined block in one of Key West's most sought-after residential pockets, this thoughtfully reimagined 4BD/3BA residence offers just over 2,000 square feet of refined island living -- the result of a multi-year renovation where no detail was overlooked. The first floor opens to a flexible bedroom or private office alongside a full bath, newly converted and finished to the same

    The Spottswood Team Truman & Co. (KW)

    1427 Washington St, Key West, FL 33040
  • /76

    $475,000

    $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 803 Sq Ft

    3930 S Roosevelt Blvd Unit N108, Key West, FL 33040

    NEW PRICE.....Welcome to this beautifully updated condo at 3930 S. Roosevelt Blvd. #N108, offering the perfect blend of comfort, convenience, and island living. Overlooking the sparkling community pool, this inviting residence features a tastefully remodeled kitchen with modern finishes, newer flooring throughout, and a bright, open living space designed for easy living and

    Barbara Crespo Keller Williams Key West Compass Realty

    3930 S Roosevelt Blvd Unit N108, Key West, FL 33040
  • /56

    $2,549,000

    • 3 Beds
    • 4 Baths
    • 2,469 Sq Ft

    2924 Riviera Dr, Key West, FL 33040

    **Seller Financing Considered** 2924 Riviera Dr is a Must See! Meticulously renovated house on the Riviera Canal. Features 3 bedrooms, 2 full baths & 2 half baths, plus separate pool / canal side cottage. Open & airy living room & kitchen gives you spectacular views of backyard, pool and canal. You can even see the pool and canal from the front door. Owner / Seller is a carpenter. House was

    Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

    2924 Riviera Dr, Key West, FL 33040
  • /7

    $269,900

    $29K PRICE DROP
    • Land
    • 0 Sq Ft

    1801 N Roosevelt Blvd, Key West, FL 33040

    Very well maintained 2017 Trident 45' Houseboat being conveyed with a leasehold slip at City's Garrison Bight Marina , in the middle of Key West ! One of the few seaworthy vessels in the Marina . Low slip fee of $ 908 per month includes free pump out , 2 parking passes , 2 very clean laundry and shower facilities , patrolled security

    Randy Moss Coldwell Banker Schmitt RE Co

    1801 N Roosevelt Blvd, Key West, FL 33040
  • /53

    $4,750,000

    • 7 Beds
    • 5 Baths
    • 3,118 Sq Ft

    901 Eisenhower Dr, Key West, FL 33040

    A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating

    Sarah Dolson Keller Williams Key West Compass Realty

    901 Eisenhower Dr, Key West, FL 33040
  • /22

    $250,000

    5555 College Rd Unit 8, Key West, FL 33040

    Lowes cost liveaboard slip for 45' x 15' boat in Key West. Live in Paradise for only $250,000 and circa $602/month (HOA fee/property taxes) + utilities.Well-protected 120 slip marina on leeward side of the island, with state of the art Bellingham floating concrete docks.Deeded dockominium (you own bay bottom rights). Easy access to Gulf of Mexico, Atlantic Ocean and The Caribbean.Has

    Jerry Hughes Beach Club Brokers (KW)

    5555 College Rd Unit 8, Key West, FL 33040
  • /59

    $2,165,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,569 Sq Ft

    3513 Sunrise Dr, Key West, FL 33040

    Wake up in Key West and own your own piece of the island!Come enjoy a second-home outdoor living lifestyle on almost 1/4 acre private fenced-in landscaped tropical grounds corner lot with heated salt water pool, large porch and deck entertainment area and outdoor kitchen and BBQ area.The first floor is set to entertaining with French Saltillo (terracotta) floors throughout, a gourmet

    Jerry Hughes Beach Club Brokers (KW)

    3513 Sunrise Dr, Key West, FL 33040
  • /44

    $1,875,000

    • 4 Beds
    • 3 Baths
    • 2,423 Sq Ft

    1516 17th Terrace, Key West, FL 33040

    Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a

    Bascom Grooms Bascom Grooms Real Estate (KW)

    1516 17th Terrace, Key West, FL 33040
  • /9

    $20,000

    $5K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    3675 S Roosevelt Blvd Unit week 42, Key West, FL 33040

    Selling weeks 42 and 43. High Tourist season. Fantasy Fest and Halloween. 2 Bedroom Villa, Ocean view sunrise view, Princess balcony

    Jenny Murphy Keller Williams Key West Compass Realty

    3675 S Roosevelt Blvd Unit week 42, Key West, FL 33040
  • /2

    $339,000

    • 2 Beds
    • 2 Baths
    • 784 Sq Ft

    5031 5th Ave, Key West, FL 33040

    A BOATER’S DREAM & KAYAKER’S PARADISE—JUST MINUTES FROM KEY WEST!Experience the ultimate Florida Keys lifestyle in the beautiful Sunset Harbor Waterfront Community, where it’s more than just a home—it’s a lifestyle! Boaters will love the convenience of community boat slips with Cow Key Channel just a 2-minute ride away, providing quick access to both the Atlantic Ocean and Gulf. Kayakers can

    Benton Langley Langley Knight Gardner Islamorada

    5031 5th Ave, Key West, FL 33040
  • /32

    $939,000

    • 4 Beds
    • 3 Baths
    • 1,580 Sq Ft

    1524 5th St, Key West, FL 33040

    Welcome to your dream home in Midtown Key West! This 4-bedroom, 3-bathroom currently being used as a 3/2 with a mother-in-law suite. This property has endless possibilities property boasts a fenced yard, perfect for privacy and outdoor enjoyment. With a durable metal roof and tile floors throughout, this home combines comfort and style. Don't miss the opportunity to own a piece of paradise.!

    Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

    1524 5th St, Key West, FL 33040
  • /61

    $2,200,000

    • 5 Beds
    • 4 Baths
    • 2,096 Sq Ft

    1320 6th St, Key West, FL 33040

    Two Parcels Included!!! Welcome to 1320 6th Street, a fantastic investment opportunity in a prime midtown Key West location. This property features three private units, each offering great rental income potential. Your chance to make money and have a home in paradise. Newly remodeled kitchen in the rental home.Enjoy the large inviting pool and well-maintained grounds, all just minutes from

    Sarah Dolson Coldwell Banker Schmitt Real Estate Co. (KW)

    1320 6th St, Key West, FL 33040
  • /15

    $599,000

    5950 Peninsular Ave Unit 674, Key West, FL 33040

    Great opportunity to own a 60' x 20' deep-water boat slip in the highly sought-after Oceans Edge Resort & Marina on Stock Island. This premier marina offers approximately 8' controlled depth with easy access to both the Atlantic Ocean and the Gulf of Mexico. Owners enjoy access to the resort's exceptional amenities, including six swimming pools, a fitness center, open parking, a fuel dock, dog

    Keys Team Bryant and Kat Expert Realty LLC (HQ)

    5950 Peninsular Ave Unit 674, Key West, FL 33040
  • /45

    $2,249,000

    $51K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 1,724 Sq Ft

    1109 Stump Ln, Key West, FL 33040

    On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces.The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that

    Terri Spottswood Truman & Co. (KW)

    1109 Stump Ln, Key West, FL 33040
  • /50

    $3,300,000

    • 4 Beds
    • 3.5 Baths
    • 2,573 Sq Ft

    214 Eanes Ln, Key West, FL 33040

    Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X flood zone, this property offers added peace of mind and potential savings on insurance--an increasingly valuable feature in today's market.This unique property is configured as two separate units, featuring a main two-story

    Jaime Caballero Century 21 Prestige Realty Group (KW)

    214 Eanes Ln, Key West, FL 33040
  • /6

    $900,000

    • Land
    • 7,405 Sq Ft
    • $5,294,118 per Acre

    5304 3rd Ave, Stock Island, FL 33040

    Zoned Mixed Use Vacant Land on Stock Island. One of the few undeveloped parcels left. This land was purchased as a Tier I protected land and owners worked with County to get Tier changed to Tier III develop-able. Property has been cleared, filled, and compacted with Riprap installed. U.S. Army Corps of Engineers (USACE) inspection on file with county for property. Owners are currently working on

    Paul LaRochelle Century 21 Circle - Key West

    5304 3rd Ave, Stock Island, FL 33040
  • /38

    $949,000

    $171K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,606 Sq Ft

    6460 Sunshine St, Key West, FL 33040

    Spacious 4-Bedroom, 3-Bath Home on Expansive Lot with Fruit Trees! Welcome to this beautifully maintained 4-bedroom, 3-bathroom home nestled on a generous 9,375 sq ft fully fenced lot. Perfect for families and entertainers alike, this property offers the ideal blend of space, comfort, and outdoor living. Inside, you'll find a thoughtfully designed layout with ample natural light, spacious

    Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

    6460 Sunshine St, Key West, FL 33040
  • /37

    $1,799,000

    • 3 Beds
    • 2.5 Baths
    • 1,456 Sq Ft

    2101 Harris Ave, Key West, FL 33040

    There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it!Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property

    The Spottswood Team Truman & Co. (KW)

    2101 Harris Ave, Key West, FL 33040
  • /19

    $750,000

    • 2 Beds
    • 2 Baths
    • 862 Sq Ft

    1004 Watson St Unit 2, Key West, FL 33040

    Positioned in the coveted X flood zone, this 2-bedroom, 2-bathroom townhome perfectly blends Old Town charm with modern convenience. As one of only two units in an exclusive boutique setting, it provides exceptional privacy just steps from local wellness hubs, neighborhood cafes, and historic sites. The efficient galley kitchen is outfitted with granite countertops and stainless-steel appliances,

    Brenda Donnelly Brenda Donnelly Real Estate LLC

    1004 Watson St Unit 2, Key West, FL 33040
  • /40

    $5,400,000

    • 6 Beds
    • 6.5 Baths
    • 2,993 Sq Ft

    613 Margaret St, Key West, FL 33040

    Step back into timeless Key West soul, where leaf-stamped garden paths, sun-dappled outdoor showers, and the gentle trickle of private pool waterfalls create an unforgettable Old Town sanctuary. Hidden behind a classic wooden gate just moments from the Historic Seaport and Duval Street, this compound offers two private, fully equipped homes on a lush 7,796-sq. ft lot, providing the ultimate

    Brenda Donnelly Brenda Donnelly Real Estate LLC

    613 Margaret St, Key West, FL 33040
  • /7

    $615,600

    $55K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,274 Sq Ft

    5030 5th Ave Unit 61, Key West, FL 33040

    This lovely townhome is located within the Islander Village HOA, a Local's Only Workforce Community. The home is elevated and above a garage for 2 cars. It has 9' ceilings on the first floor, a kitchen, 1⁄2 bath, living room and a lovely front and back porch. Upstairs is a large primary bedroom with 3 closets, two additional bedrooms and 2 full bathrooms. Additionally, the home has a metal roof

    Deborah Batty Location 3 Real Estate of KW Inc (KW)

    5030 5th Ave Unit 61, Key West, FL 33040
  • /50

    $3,400,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,691 Sq Ft

    141 Simonton St, Key West, FL 33040

    Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the

    Brenda Donnelly Brenda Donnelly Real Estate LLC

    141 Simonton St, Key West, FL 33040
  • /23

    $750,000

    $89K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 712 Sq Ft

    508 Louisa St Unit 3, Key West, FL 33040

    TRANSIENT LICENCE RECEIVERSHIP ZONE!Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience.Nestled in the heart of Key West, this condo boasts proximity to

    Paul Brooks Compass Florida, LLC

    508 Louisa St Unit 3, Key West, FL 33040
  • /37

    $2,250,000

    • 3 Beds
    • 3.5 Baths
    • 1,470 Sq Ft

    1300 Seminary St, Key West, FL 33040

    If you are seeking a private tropical backyard oasis look no further. This charming 2 story home is situated on a corner parcel in a quiet and peaceful mid town neighborhood. Behind the white picket fence, you will be welcomed to a great room with dramatic ceiling heights, wrapped with sliding glass doorwalls that open to over 500 square feet of covered porches. This home has been very well

    Wendy Zintsmaster Truman & Co. (KW)

    1300 Seminary St, Key West, FL 33040
  • /37

    $1,875,000

    $300K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,760 Sq Ft

    1115 Fleming St, Key West, FL 33040

    This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated--so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. There's not another lot like it in Old Town. The

    Derek Epperly, PA Keys Atlantic Realty

    1115 Fleming St, Key West, FL 33040
  • /9

    $675,000

    • 3 Beds
    • 3 Baths
    • 1,358 Sq Ft

    3314 Northside Dr Unit 13 & 13A, Key West, FL 33040

    Two well kept condo units at Solana Village in Key West's New Town neighborhood represents a solid investment opportunity. Conveniently situated near local schools, government offices, retail centers, a movie theater, and marinas, the property offers both lifestyle and income potential.The second-floor unit (13) is a 2-bedroom, 2-bathroom with all-tile flooring and a private balcony currently

    Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

    3314 Northside Dr Unit 13 & 13A, Key West, FL 33040
  • /11

    $999,000

    • Land
    • 6,534 Sq Ft
    • $6,660,000 per Acre

    2330 Staples Ave, Key West, FL 33040

    Discover a rare investment opportunity in the heart of Key West. This spacious corner duplex lot at 2330 Staples St and 1428 6th St offers incredible potential with two separate addresses and alley access for three convenient side entrances. The large lot features a charming, spacious cottage complete with a full kitchen, a bedroom with ample closet space, a stylish bathroom, and an attached

    Graciela Lozano KeysLifestyle Real Estate (KW)

    2330 Staples Ave, Key West, FL 33040
  • /42

    $1,395,000

    • 2 Beds
    • 4 Baths
    • 1,092 Sq Ft

    709 Olivia St, Key West, FL 33040

    NEW LISTING IN OLD TOWN WITH OFF STREET PARKING! This Old Town investment property comes fully furnished so you can move right in or start renting immediately. It is a legal DUPLEX with two units, each having one bedroom and one and a half bathrooms. Located on a fenced corner lot in Old Town, it's just blocks from Duval Street, making it very convenient for dining, shopping, nightlife and

    Bascom Grooms Bascom Grooms Real Estate (KW)

    709 Olivia St, Key West, FL 33040
  • /22

    $935,000

    $63K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 420 Sq Ft

    817 Terry Ln, Key West, FL 33040

    One Bedroom / One bathroom PLUS super cool Sleeping Loft! THIS is it! Step into a piece of Old Town Key West history.Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive.Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key

    Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

    817 Terry Ln, Key West, FL 33040
  • /13

    $1,899,000

    • 7 Beds
    • 6 Baths
    • 2,790 Sq Ft

    909 Grinnell St, Key West, FL 33040

    Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! That's less than $272K per unit! Renovations in progress. Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime location, just 1/2 block from cemetery and 1/2 block off Truman Ave. Currently configured as 6

    Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

    909 Grinnell St, Key West, FL 33040
  • /48

    $3,600,000

    • 4 Beds
    • 4 Baths
    • 2,691 Sq Ft

    119 Simonton St, Key West, FL 33040

    Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and spanning a generous 2,691 square feet, this residence seamlessly blends sophisticated contemporary design with the timeless allure of Key West. The interior features new white oak flooring that leads you through an open-concept

    Brenda Donnelly Brenda Donnelly Real Estate LLC

    119 Simonton St, Key West, FL 33040
  • /2

    $2,500

    5950 Peninsular Ave Unit 640, Key West, FL 33040

    Prestigious boat slip for rent at Ocean's Edge Marina, suitable for boats up to 50FT located on the North pier with ample water access boasting a 6ft control depth. Features include a nearby fuel station and access to the hotel pool for tenants. Ideal for water enthusiasts seeking a premium marina experience. Daily, monthly or long term rentals available. Air bnb's or houseboats are not allowed.

    Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

    5950 Peninsular Ave Unit 640, Key West, FL 33040
  • /55

    $1,245,000

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    243 Golf Club Dr, Key West, FL 33040

    MOTIVATED SELLER! Turn Key Golf Club home overlooking the 17th hole in the Sanctuary. This home is located on one of the largest lots in the development and is approved by the HOA to build your dream pool (buyer to verify). The home features a rare private oversized carport for two vehicles and a detached storage unit. The Key West Golf Club community features two gorgeous pools surrounded by

    Jessica Prescott Coastal Collection Real Estate Inc.

    243 Golf Club Dr, Key West, FL 33040
  • /23

    $675,000

    $174K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,342 Sq Ft

    1425 Eliza St, Key West, FL 33040

    3 bedroom single-family home offering the opportunity to add a second bathroom within the existing roofline. Relax on the covered front porch and enjoy the Key West lifestyle. The private backyard provides space for a pool or outdoor entertaining. A great chance to renovate and make this home your own.

    Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

    1425 Eliza St, Key West, FL 33040
  • /16

    $700,000

    • 3 Beds
    • 2 Baths
    • 1,214 Sq Ft

    3314 Northside Dr Unit 42, Key West, FL 33040

    Rarely available 3-bedroom residence in Solana Village, ideally situated in Key West's New Town neighborhood. This top-floor unit offers an excellent investment opportunity with a tenant already in place, along with off-street parking, community pool access, and a spacious balcony for enjoying the island lifestyle.The thoughtfully designed layout features a charming spiral staircase leading

    The Spottswood Team Truman & Co. (KW)

    3314 Northside Dr Unit 42, Key West, FL 33040

Showing Results 201 - 240, Page 6 of 8

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