Winhall, VT Homes

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  $1,100,000 Under Contract

  • 5 Beds
  • 4 Baths
  • 4,788 Sq Ft

  6 Chad Cir, Winhall, VT 05340

  Tucked away at the end of a private cul-de-sac and just minutes from Stratton's slopes, this beautifully designed mountain home offers the perfect blend of comfort and luxury. The open-concept floor plan features a chef’s kitchen with granite countertops, a 6-burner professional gas stove, double ovens, a farm sink, and a wet bar with ice maker—ideal for entertaining. Wide pine floors and a

  Carrie Mathews Winhall Real Estate

  6 Chad Cir, Winhall, VT 05340
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  /35

  $339,000 Sold Oct 20, 2025

  • 1,120 Sq Ft
  • $303/SF
  • 37 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  33 Aspen Ln, Bondville, VT 05340

  Minutes from Stratton Mountain, this cozy chalet offers the perfect mountain escape with timeless character and room to make it your own. Featuring a classic chalet style floor to ceiling stone fireplace and wood interior, this home exudes vintage alpine charm. There are three bedrooms, two baths and an open concept living space, providing plenty of room for gatherings or weekend getaways.

  Alison Cummings Cummings & Co

  33 Aspen Ln, Bondville, VT 05340
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  /40

  Est $568,774 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  10 Deer St, Bondville, VT 05340

  10 Deer St, Bondville, VT 05340
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  /31

  $949,000 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 2,658 Sq Ft

  73 Cranberry Hill Rd, Winhall, VT 05340

  Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

  Carrie Mathews Winhall Real Estate

  73 Cranberry Hill Rd, Winhall, VT 05340
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  /44

  $2,200,000 Sold Oct 14, 2025

  • 7,625 Sq Ft
  • $289/SF
  • 190 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 2000

  19 Old Town Rd, Bondville, VT 05340

  Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

  Christiane Carroccio TPW Real Estate

  19 Old Town Rd, Bondville, VT 05340
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  /29

  Est $676,631 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,179 Sq Ft

  32 Beaver St, Bondville, VT 05340

  32 Beaver St, Bondville, VT 05340
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  /32

  $450,000

  • 5 Beds
  • 3 Baths
  • 2,303 Sq Ft

  44 Lake Rd, Bondville, VT 05340

  Nestled in the woods on a generous private lot, 44 Lake Road is a contemporary Vermont retreat offering peaceful seclusion with big-sky views of Stratton Mountain. Designed to blend with its natural surroundings, this home features warm wood accents, soaring ceilings, and walls of glass that bring the outdoors in. The open main living area is ideal for après-ski gatherings, with a spacious great

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  44 Lake Rd, Bondville, VT 05340
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  /24

  $1,025,000 Sold Oct 10, 2025

  • 2,160 Sq Ft
  • $475/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1988

  10 Middle Ridge Rd, Winhall, VT 05155

  Fox Chapel luxury townhome at Stratton. This four bedroom, four bathroom home is offered with the ability to skip the wait list at the Stratton Mountain Club. Renovated bathrooms and air conditioning make this the year round place to be. Prime location next to the ‘Chapel of the Snows’ and the Commons, walk to the Stratton village for ski access, dining, shopping, and resort amenities. Watch the

  Christiane Carroccio TPW Real Estate

  10 Middle Ridge Rd, Winhall, VT 05155
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  /40

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,016 Sq Ft

  12 Quarter Mile Rd, Winhall, VT 05360

  12 Quarter Mile Rd, Winhall, VT 05360
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  /46

  $660,000

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft

  9 Pond View Rd Unit 9, Winhall, VT 05340

  Exceptional Renovation and Prime Intervale Location on the Pond . Beautiful upscale kitchen that opens to a wonderful great room with wood burning fireplace, cathedral ceiling, a spacious dining area and new deck with steps to the outdoors and pond. Tasteful details of this highly desirable floor plan with three bedrooms/3 baths that includes two bedrooms ensuite and a loft. The loft features

  Kim Morgan-Wohler Wohler Realty Group

  9 Pond View Rd Unit 9, Winhall, VT 05340
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  /27

  $440,000 Sold Oct 03, 2025

  • 1,400 Sq Ft
  • $314/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  6 Moose Maple Rd, Winhall, VT 05340

  Located in the desirable Moose Maple section of Birch Hill, this well-maintained 3-bedroom, 2-bath Co-Op offers some of the best direct views of Stratton Mountain, along with the convenience of a community shuttle and close proximity to the newly rebuilt seasonal pool. Freshly painted and thoughtfully updated, the condo features flexible living spaces including a lower-level bedroom with a custom

  Andy Reed Four Seasons Sotheby's Int'l Realty

  6 Moose Maple Rd, Winhall, VT 05340
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  /31

  Est $550,668 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft

  22 Little Brook Rd, Winhall, VT 05340

  22 Little Brook Rd, Winhall, VT 05340
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  /21

  $485,000

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft

  19 Deer Run Rd, Winhall, VT 05340

  Immerse Yourself in Vermont Charm: Contemporary Home in Strattonwald!Live the Stratton dream in this stunning 3-bedroom, 2-bathroom contemporary home nestled within the Strattonwald community at Stratton Resort, VT. This impeccably designed home offers the perfect blend of modern comfort and rustic charm, ideal for your next Vermont getaway. Unwind and reconnect with a spacious living area

  Robin Apps Four Seasons Sotheby's Int'l Realty

  19 Deer Run Rd, Winhall, VT 05340
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  /32

  $560,000 Sold Sep 26, 2025

  • 1,400 Sq Ft
  • $400/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  35 Glendon Hills Rd, Bondville, VT 05340

  Discover your dream home in Glendon Hills! A truly rare opportunity, this property is the first to become available in this coveted neighborhood in over a decade. Imagine owning a private 1-acre sanctuary with your own picturesque, thriving pond. Inside, experience the joy of cooking in a well-appointed chef's kitchen and the comfort of an open-concept design centered around a charming stacked

  Robin Apps Four Seasons Sotheby's Int'l Realty

  35 Glendon Hills Rd, Bondville, VT 05340
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  /40

  Est $855,432 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,872 Sq Ft

  34 Raspberry Hill Rd, Winhall, VT 05340

  34 Raspberry Hill Rd, Winhall, VT 05340
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  /12

  $95,000

  • Land
  • 1 Acre
  • $95,000 per Acre

  41 Moose Hollow Rd, Winhall, VT 05340

  Build your dream home on this ready-to-go 1-acre lot in the Green Mountains. Located on a private gravel road in Winhall, this mostly cleared parcel offers a gentle slope, power at the road, a nearby stream, and a state-issued 4-bedroom septic permit already in place. The setting provides a peaceful, natural feel while keeping you close to the best of Southern Vermont. Bromley Mountain is about

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  41 Moose Hollow Rd, Winhall, VT 05340
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  /39

  $2,250,000 Sold Sep 25, 2025

  • 6,471 Sq Ft
  • $348/SF
  • 88 Days On Market

  • 8 Beds
  • 8.5 Baths
  • Built 2009

  69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155

  This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit.The main level of the home features a Gourmet Kitchen, grand

  Sara Buckley Josiah Allen Real Estate, Inc.

  69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155
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  /26

  Est $219,599 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 595 Sq Ft

  28 Stratton Rd W Unit 28, Winhall, VT 05340

  28 Stratton Rd W Unit 28, Winhall, VT 05340
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  /27

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  8 Winhall Woods Rd, Winhall, VT 05340

  Discover this quintessential Vermont ski chalet, perfectly set on a quiet dead-end road with views of Bromley Mountain from the property. Warm and inviting, the home is filled with natural wood throughout, creating the classic mountain-home atmosphere buyers love. Offering both charm and convenience, the location is ideal—just 2.5 miles to Bromley Mountain, 10 miles to Stratton, and only 8 miles

  Carrie Mathews Winhall Real Estate

  8 Winhall Woods Rd, Winhall, VT 05340
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  /3

  $26,000 Sold Sep 19, 2025

  • Land
  • 1.1 Acres
  • $23,636 per Acre

  • 656 Days On Market

  0 Deepwoods Rd Unit 4976604, Winhall, VT 05340

  Discover the perfect spot for your next adventure with this prime piece of land in Winhall. Imagine placing a charming tiny home on this property and owning your own slice of Vermont paradise. The land comes with preliminary septic design information, making it easier for you to start your new chapter. Enjoy the best of all worlds: live amidst the breathtaking mountains in a cozy, manageable

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  0 Deepwoods Rd Unit 4976604, Winhall, VT 05340
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  /35

  Est $443,184 Not Listed For Sale

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

  383 Winhall Hollow Rd, Bondville, VT 05340

  383 Winhall Hollow Rd, Bondville, VT 05340
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  /4

  $400,000

  • Land
  • 8.01 Acres
  • $49,938 per Acre

  248 French Hollow Rd, Winhall, VT 05340

  Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

  Kim Morgan-Wohler Wohler Realty Group

  248 French Hollow Rd, Winhall, VT 05340
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  /22

  $445,000 Sold Sep 16, 2025

  • 1,590 Sq Ft
  • $280/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  163 Vt Route 30, Winhall, VT 05340

  Charming Restored Post & Beam Home with Commercial Zoning Near Stratton. Discover the perfect blend of rustic charm and modern functionality in this beautifully restored post and beam home ideally situated at the corner of Vermont Route 30 and scenic Kendall Farm Road. Featuring three bedrooms and two full baths, the home offers soaring vaulted ceilings, exposed beams, and an abundance of natural

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  163 Vt Route 30, Winhall, VT 05340
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  /15

  Est $521,198 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,416 Sq Ft

  6 Old Snow Valley Rd, Winhall, VT 05340

  6 Old Snow Valley Rd, Winhall, VT 05340
• 

  

  /25

  $385,000

  • Land
  • 41.1 Acres
  • $9,367 per Acre

  00 Ross Rd, Winhall, VT 05340

  Welcome to 41.1 acres of quintessential Vermont beauty, ideally located between downtown Manchester (11 minutes), Bromley Mountain (6 minutes), and Stratton Mountain (15 mins). This property offers the best of both worlds—easy access to town, ski mountains, and year-round recreation, yet a peaceful and private setting surrounded by nature. The land features a meandering stream, a mix of mature

  David Shehadi Josiah Allen Real Estate, Inc.

  00 Ross Rd, Winhall, VT 05340
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  /47

  $822,500 Sold Sep 12, 2025

  • 2,598 Sq Ft
  • $317/SF
  • 18 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1983

  C1 Meadow Ridge Rd, Winhall, VT 05340

  WELCOME TO YOUR FAMILY'S PERFECT MOUNTAIN RETREAT..WELCOME TO PIPER RIDGE!! This spacious 4 bedroom/4 bath condo is designed for comfort, convenience and offers an exceptional blend of mountain charm and modern amenities! Enjoy two open concept living areas with cozy wood burning fireplaces, fully equipped kitchen, private balcony showcasing winter mountain views...Perfect for entertaining...With

  Sunny Breen Josiah Allen Real Estate, Inc.

  C1 Meadow Ridge Rd, Winhall, VT 05340
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  /20

  Est $473,649 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,212 Sq Ft

  109 Sylvan Ridge Rd, Winhall, VT 05340

  109 Sylvan Ridge Rd, Winhall, VT 05340
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  /30

  $735,000

  • 3 Beds
  • 3 Baths
  • 2,317 Sq Ft

  32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

  This gorgeous Stratton area townhome is designed for comfort and style, featuring three spacious bedrooms, three baths plus an open loft. Being a Highgate model, it offers a second family room with ample space for relaxation and entertainment, making it perfect for holiday gatherings. The interior of this special home has been freshly painted in October '25 and stunning wide-board pine floors

  Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
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  /10

  $385,000 Sold Sep 10, 2025

  • Land
  • 24.54 Acres
  • $15,689 per Acre

  • 28 Days On Market

  0 River Rd, Winhall, VT 05340

  24+ Acres in Winhall, VT — Private 1+ Acre Pond, River Frontage & Minutes from Stratton | Welcome to a rare opportunity in the heart of Vermont’s Green Mountains — a stunning 24+ acre parcel in Winhall offering a unique combination of convenience, privacy, natural beauty, and year-round adventure, just minutes from Stratton Resort. With a state-issued wastewater permit in place, the land is

  Cheyanne Pugliese

  0 River Rd, Winhall, VT 05340
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  /39

  Est $1,139,026 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,814 Sq Ft

  19 Maple Hill Rd, Winhall, VT 05340

  19 Maple Hill Rd, Winhall, VT 05340
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  /39

  $599,000

  • 5 Beds
  • 3.5 Baths
  • 2,468 Sq Ft

  17 Signal Hill Rd, Winhall, VT 05340

  17 Signal Hill Road offers Vermont charm in a secluded mountain setting. With over 2,400 square feet of living space, this five-bedroom, three-and-a-half-bath home has been thoughtfully maintained and move-in ready. The main level features a spacious living room with a dramatic fieldstone fireplace, vaulted ceilings, and skylights that fill the home with natural light. A loft overlooking

  Christiane Carroccio TPW Real Estate

  17 Signal Hill Rd, Winhall, VT 05340
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  /59

  $1,082,500 Sold Aug 29, 2025

  • 4,054 Sq Ft
  • $267/SF
  • 45 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2005

  4 Garden Loop Rd, Winhall, VT 05340

  Your Stratton Mountain retreat awaits! This beautiful turnkey mountain home just off the Stratton Mountain Road is the perfect location for family gatherings, ski trips, hiking and more. This three-bedroom, three-bath home on three levels includes a breathtaking great room with a stone fireplace and vaulted ceilings. Dining room and additional breakfast area next to the kitchen. A large open

  Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

  4 Garden Loop Rd, Winhall, VT 05340
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  /40

  Est $809,758 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,196 Sq Ft

  40 Loop Rd, Winhall, VT 05340

  40 Loop Rd, Winhall, VT 05340
• 

  

  /22

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340

  Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

  Robin Apps Four Seasons Sotheby's Int'l Realty

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340
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  /51

  $1,300,000 Sold Aug 25, 2025

  • 4,541 Sq Ft
  • $286/SF
  • 7 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2004

  33 Jamie Ln, Bondville, VT 05340

  Exceptional Log Home tucked away in the beautiful Green Mountains of Vermont. Welcome to 33 Jamie Lane a 12 acre sanctuary minutes to Stratton Mountain Resort. This extraordinary property offers true privacy surrounded by woods and nature. Features three finished levels of dramatic living space with floor to ceiling windows , soaring stone fireplace, and cherry floors. Open concept kitchen/dining

  Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

  33 Jamie Ln, Bondville, VT 05340
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  /40

  Est $610,400 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,024 Sq Ft

  381 Winhall Hollow Rd, Bondville, VT 05340

  381 Winhall Hollow Rd, Bondville, VT 05340
• 

  

  /59

  $2,800,000

  • 3 Beds
  • 3.5 Baths
  • 3,938 Sq Ft

  23 Valley View Rd, Winhall, VT 05340

  Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

  Kim Morgan-Wohler Wohler Realty Group

  23 Valley View Rd, Winhall, VT 05340
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  /26

  $795,000 Sold Aug 21, 2025

  • 1,624 Sq Ft
  • $490/SF
  • 0 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1970

  5 Founders Hill Rd, Winhall, VT 05360

  Nestled just minutes from Stratton Mountain, this adorable 3-bedroom chalet is your perfect year-round getaway or cozy full-time retreat. With its classic alpine charm and thoughtful modern updates, it offers the best of both worlds.Step inside to find welcoming interior, with large windows upstairs that fill the home with natural light throughout the day. The open living space invites

  Jamie Wylie Stratton Real Estate

  5 Founders Hill Rd, Winhall, VT 05360
• 

  

  /31

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,817 Sq Ft

  22 Mountain View Rd, Winhall, VT 05360

  22 Mountain View Rd, Winhall, VT 05360
• 

  

  /28

  $1,700,000

  • 4 Beds
  • 3.5 Baths
  • 2,363 Sq Ft

  43 Middle Ridge Rd Unit 415, Winhall, VT 05155

  Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

  Edwin Kevil Stratton Real Estate

  43 Middle Ridge Rd Unit 415, Winhall, VT 05155

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