$3,250,000 $1,012 per sq.ft. West Windsor VT Home »


Price Change! Reduced by $100,000 down 3% on June 28th 2026
5 Beds | 5 Baths |   Total Sq. Ft. 3212  |  Acres: 98
Wednesday Apr 15, 2026
Description: Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust, enrolled in Current Use. The main floor offers a new kitchen which boasts a beautiful 11' quartzite island & counters. Dining & Family Room with soapstone woodstove, Living Room with a new Rumford Fireplace with rod iron & glass doors for efficiency. A large Sunroom with slate floor, more than an entry it's a nice transitional space to enjoy, 3 BR/3 BA and a Sitting area on the 2nd floor with a tranquil view of the back fields. 2 additional BRs and a half bath on the 3rd floor. All new wiring, plumbing, new Bosch propane furnace supplies radiant heat, triple pane, Anderson low-E4 windows, sheetrock, DaVinci slate-like rubber roof & cherry floors. Fully insulated, extremely efficient. Custom built trim, wide baseboards, wainscoting & cabinets. 200+ year old pine boards from the house were used to craft bathroom vanities, 3rd floor stairs & beautiful doors. Outdoor amenities include in ground pool, gardens & lovely stone patio. A large-3600 sq ft former dairy barn with new wiring & FHA furnace & oil tank. Now used as a garage, workshop & abundant storage space offers ENDLESS possibilities! See MLS Property & Listing Details & 60 images.

$1,299,000 $297 per sq.ft. Weston VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 4372  |  Acres: 15.1
Monday May 11, 2026
Description: OPEN HOUSE Saturday 6/13 12 - 2 PM!! Set in the heart of Vermont's four season playground, this impeccably maintained 4 bedroom, 3 bath home with a private swimming pond offers the perfect balance of comfort, space and outdoor living. Thoughtfully built by the previous owners and meticulously maintained by the current owners, the property reflects care, pride, and attention to detail, with many thoughtful upgrades and improvements made. The location is hard to beat - just minutes to four premier ski areas: Okemo Mtn, Magic Mtn, Stratton Mtn, and Bromley Mtn. Conveniently located near shopping, dining, and amenities in Rutland, Weston, and Manchester, with nearby ponds and lakes adding to the endless year round recreation opportunities. Designed for gathering and relaxing, the home features a spacious open kitchen and dining area, inviting family room and living room, and a large mudroom ready for all your gear after a day of skiing, hiking, snowmobiling, or lake adventures. A first floor den with an attached bath offers wonderful flexibility and could easily serve as a first-floor bedroom for guests or those seeking single level living options. The spacious second floor includes four comfortable bedrooms, a dedicated office, and large laundry. The primary suite is a true retreat with a generous walk in closet, oversized bath, soaking tub w/ mountain views. A full basement with bulkhead access offers endless possibilities - ideal for storage, a workout area, workshop space, or future finished living space. Outside, mature perennial gardens surround the home, a covered front porch and sun drenched back deck with hot tub create the perfect setting to take in the mountain views and quiet surroundings. The stunning swimming pond completes this private Vermont oasis. Whether you're looking for a year-round residence or the ultimate Vermont getaway, this exceptional property offers the very best of Vermont living in every season. See MLS Property & Listing Details & 43 images.

$3,195,000 $635 per sq.ft. Weybridge VT Home »

Waterfront on Pond _Unnamed
5 Beds | 5 Baths |   Total Sq. Ft. 5687  |  Acres: 26.1
Thursday May 21, 2026
Description: The Drake House is a rare Vermont landmark, nearly two centuries in the making and thoughtfully carried forward by generations of careful stewards. Built in 1825 by Asaph Drake and his wife, this distinguished brick Federal home has long held an important place in the Middlebury area, with later connections to the Morgan Horse Farm, ownership by a Middlebury College president, and listing on the National Register of Historic Places. Most recently purchased in 2023, the 5,030-square-foot home has been meticulously modernized for contemporary living while preserving the character, craftsmanship, and soul that make it irreplaceable. Light-drenched interiors feature original pumpkin pine floors, historic brickwork, marble accents, reclaimed oak flooring, a restored archway, and elevated updates throughout, including a custom kitchen with coffered ceilings, walnut island, Fisher & Paykel dishwasher, and black enamel AGA propane range. Surrounded by approximately 650 acres of conserved land just five minutes from Middlebury village, the property feels deeply private while remaining closely connected to the landscape, with gardens, a pond, outdoor living spaces, and access to the MALT system's 18-mile trail network. Inside, gracious gathering spaces, a parlor with fireplace and beehive/pizza oven, a serene primary wing with office and cedar sauna, and a wine cellar create a home that is both historic and deeply livable. A post-and-beam barn/garage with guest apartment, additional barn, and second driveway complete this beautifully renewed Federal-era retreat, ready for its next chapter. See MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$1,150,000 $583 per sq.ft. Whitingham VT Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1972  |  Acres: 100
Friday May 22, 2026
Description: Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to the East. The property could easily accommodate a beautiful new build, or else could be rehabbed into a working dairy or gentleman's farm, with privacy and access rare to find. The main house presently features 4 bedrooms, 1 bath, a large kitchen and dining area, den, and walk in pantry. There is an attached two story barn for storage, which leads into the recently built oversized 3 car garage with 12 foot doors, ideal for equipment or classic car storage. From this you can go to the 38x144 large dairy barn with stalls, horse paddocks, and hayloft, or the tremendous oversized dairy barn with 90 stanchions between the two barns, and main room upstairs, which could be converted into amazing space for those with vision. These are the best maintained functioning farm barns I have seen in 20 years. Add to that a full equipment shed, dairy processing area, approx 40 acres of pasture and fields, sugar house, pond, a network of trails, 60 acres of mature woodlands, and an idyllic home site at the crest of the upper field, and you have everything you could possibly want in a true Vermont farm property, with enjoyment and expansion potential for years to come. Recent updates include a new roof on the house, generator, and a full clean out. Don't sleep on this one of a kind opportunity. Property is in Current Use. See MLS Property & Listing Details & 42 images.

$1,400,000 $572 per sq.ft. Wilmington VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 3844  |  Acres: 2.38
Sunday Jan 4, 2026
Description: This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf courses, and local amenities, this home suits a luxury second home, a strong investment property, or a comfortable year-round residence. The floor plan features a main level primary bedroom with an en suite bath and walk-in closet, plus what could be a second primary bedroom on the lower level with a full bath and direct walkout access to the covered patio. There are two more spacious bedrooms on the top level, each with its own full bathroom, and a bonus room for an office or extra sleeping space. Highlights include a two-story great room with a wood burning fireplace, a large covered porch, and an oversized attached two car garage. Buyers who commit early could personalize finishes within the builder's allowances or choose upgrades at their expense. See MLS Property & Listing Details & 16 images. Includes a Virtual Tour

$1,697,000 $701 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
4 Beds | 3 Baths |   Total Sq. Ft. 2420  |  Acres: 1.72
Tuesday Dec 23, 2025
Description: This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by the current owners, and features a lodge style quite unique in the area which offers warm charm and Vermont rustic styling perfect for a retreat. Inside you are treated to vaulted ceilings in the main living room with floor to ceiling stone fireplace. There are freshly painted walls and exposed woodwork throughout, a country kitchen with gas stove and basin vintage sink, great light from the many windows and updated lighting, a tremendous great room addition perfect for entertaining with wood stove for ambiance, two main floor suites including a large primary, an upstairs guest suite, a spacious sleeping loft, great storage and closet spaces, a den/tv room ideal as an office or overflow sleeping, and lake views from every bedroom. Outside you'll find a large stone patio with hot tub which leads down to the extensive perennial landscaping and path to the water. There is a boathouse at the lake for lake storage, a large dock, swim platform, and level lawn space for fun in the sun. The home has a detached garage great for off season boat storage or whatever you may need. Updated septic! See MLS Property & Listing Details & 32 images.

$1,975,000 $467 per sq.ft. Wilmington VT Home »

Waterfront on Lake Harriman Reservoir
5 Beds | 5 Baths |   Total Sq. Ft. 5063  |  Acres: 10.08
Wednesday Jun 10, 2026
Description: Breathtaking Lake and Vermont Forever Wild views from this 10 acre parcel overlooking Lake Whitingham, with deeded lake access. The premiere Old Mill Lane development is host to some of Wilmington's finest homes thanks to large private parcels, extended driveways, exclusive shared lake access and beach area with kayak rack, swimming cove, and easy access to the Village of Wilmington and nearby ski areas of Mount Snow and the Hermitage Club. This 2005 home sits on 10+ acres with tremendous exposure and a serene lake setting. This was a custom architect designed build which is being offered by the original owners. The home features a large open living space with high ceilings and custom mill work throughout, gorgeous wood floors and extensive wide wood moldings, a spacious area which leads to the large screened porch, chefs kitchen with breakfast bar and stainless appliances, all with breathtaking lake and sunset views. There is a main floor guest suite with gorgeous bath and walkin closet, a warm office with built ins which could serve as overflow sleeping, half guest bath, dual main floor entries, and main floor laundry. Up the custom silo staircase is the primary suite with second wood burning fireplace, walk in closet, upscale bath with soaking tub overlooking the view, and private sun deck. There are three more upstairs bedrooms and a large full bath with separate commode. The finished lower level has a large family room space, 4th full bath, and three massive bonus rooms which are insulated and ready to be finished if you want the extra space as bedroom, theater, game room, or gym. This is all complemented by the two car garage, covered front porch, wraparound covered rear porch to entertain while overlooking the scenic vista, extensive landscaping, perennial gardens, stone work, and exposed ledge, extremely private location, and extensive recent updates. This home is ready for immediate enjoyment and turn key use, affording downtime, not upkeep. See MLS Property & Listing Details & 43 images.

New Listing! Wilmington VT Home for sale $$1,998,000 $476 per sq.ft.

$1,998,000 $476 per sq.ft. Wilmington VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 4200  |  Acres: 20
Wednesday Jul 1, 2026
Description: Private Vermont Sanctuary with Spectacular Mountain Views. Tucked away on a quiet dead-end road, yet just minutes to Hermitage Club, Mount Snow and downtown Wilmington. Every room offers a view. Direct snowmobile access and walking trails! Set on 20 private acres in the heart of Vermont's Green Mountains, the property features panoramic views of Haystack, Mount Snow, and the spine of the southern Green Mountains. With over 4,200 square feet of thoughtfully designed living space, the interior boasts clean lines, a Primary suite with walk-in closet and spa-like bath. Floating staircase, a large foyer, and a screened-in porch for enjoying warm evenings. Vaulted ceilings, radiant heat throughout, and walls of windows frame the stunning mountain and valley vistas. Open-concept kitchen and dining area with granite countertops, custom cherry cabinets and flooring, large center island, and a massive stone fireplace. Direct access to multi-level decks. Spacious living room with exposed beams and a cozy sitting area with a Projection System and a Custom high-end audiophile Sound system. Oversized heated 3-car garage. Enjoy outdoor living at its best with beautifully maintained flower gardens, open fields, a mature mixed forest, a patio, a hot tub, an outdoor shower, and creek frontage. See MLS Property & Listing Details & 60 images.

New Listing! Wilmington VT Home for sale $$2,100,000 $493 per sq.ft.

$2,100,000 $493 per sq.ft. Wilmington VT Home »

7 Beds | 4 Baths |   Total Sq. Ft. 4256  |  Acres: 0.55
Wednesday Jun 17, 2026
Description: Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and meticulous maintenance, this home is turn key for immediate enjoyment, with features including an open concept design, large great room with vaulting ceilings and exposed beams, a stone hearth with wood burning fireplace, upscale country kitchen with stainless appliances and granite counters, a secondary wet bar area, sizeable dining table for all your guests, wood floors throughout, a main floor primary suite with walk-in closets and large tiled bath, dual rustic bunk rooms, a lower level guest suite, 7 spacious bedrooms in total, a large family room for great separate entertaining space, movies, and games, as well as an adjacent tv area, and a tremendous mudroom with built in cubbies for all your gear after a day on the trails. There is also a large covered front porch to keep the snow at bay with wood storage, massive hot tub, fenced in dog area, generator, tremendous parking, and nice lawn space without being much to maintain. With proximity like this and creature comforts from home, this makes for a great ski home, as well as a welcome respite from the metropolitan bustle year round. See MLS Property & Listing Details & 33 images.

$2,195,000 $623 per sq.ft. Wilmington VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3524  |  Acres: 0.5
Wednesday May 20, 2026
Description: A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake -- with a private dock -- just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats tend to head for the public-access Harriman Reservoir on the southern end of Wilmington, Raponda remains a predominantly owner-enjoyed lake. The result is noticeably less boat noise and wake, making it equally wonderful for kayaking, paddleboarding, and peaceful summer mornings on the water. The property sits on a generous, nicely sized parcel with sweeping level lawn space, a private yard with fire pit, ample parking, kayak racks, and a private dock -- which transforms into an ice skating destination come winter. Inside the fully remodeled and expanded vintage four-bedroom, four-bath lake house, an open-concept floor plan invites you in with warm wood floors throughout, a living room anchored by a wood-burning stove set in a stone hearth, and a well-appointed kitchen with stainless appliances and island. A relaxing entertainment area with full bath flows into the heated sunroom addition, with expansive windows framing the lake views and opening onto a wraparound deck. A generous mudroom entry handles gear for every season with ease. Upstairs, the primary suite offers wonderful natural light and a luxurious bath, alongside three spacious guest bedrooms, two additional full baths, custom built-in storage, and a lovely office space. The practical upgrades here are just as impressive: efficient mini-split heating and air conditioning, an attached garage for gear storage, an updated septic system, and a private driveway with ample parking. All of it recently completed, the home is completely turnkey -- so all you'll have to worry about is downtime, not upkeep. See MLS Property & Listing Details & 39 images.

$2,799,000 $846 per sq.ft. Wilmington VT Home »


Price Change! Reduced by $1,701,000 down 61% on July 14th 2026
Waterfront on River North Branch Deerfield River
6 Beds | 3 Baths |   Total Sq. Ft. 3309  |  Acres: 260
Thursday Sep 28, 2023
Description: Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and whimsical and yes it gets even better--this is waterfront property that offers substantial frontage on the North Branch of the Deerfield River, a haven for fly fishing & serenity. For the farmer in you, two livestock barns provide ample space for your animals or envision more--the potential to be certified organic or transform these barns into charming event spaces or the farm into a Bed and Breakfast to blend Vermont's rural allure with modern comfort. This property is an opportunity waiting to be realized. With 5 identified potential new home sites, you may consider creating a family compound or explore development possibilities. Additionally, there's a sugar house and sugar lot, operated with modern efficiency for maple syrup production. Historic Wilmington, is only a stone's throw away and Mount Snow and the prestigious Hermitage Club are just a few miles North. Rarely does an opportunity like this arise. While currently part of Vermont's Current Use program, removal is an option upon sale, making your vision even more attainable. Unlock the limitless posibilities at Wheeler Farm! See MLS Property & Listing Details & 41 images.

New Listing! Wilmington VT Home for sale $$3,495,000 $520 per sq.ft.

$3,495,000 $520 per sq.ft. Wilmington VT Home »

9 Beds | 11 Baths |   Total Sq. Ft. 6726  |  Acres: 16.79
Tuesday Jun 16, 2026
Description: Green Meadows Farm is a rare Southern Vermont estate where timeless character, modern comfort, and exceptional recreational amenities come together across more than 16 picturesque acres. Just minutes from Lake Raponda, downtown Wilmington, Mount Snow, and The Hermitage Club, this remarkable property offers sweeping mountain views, stunning sunsets, and the space to create lasting memories for generations. At the heart of the property is a beautifully maintained six-bedroom farmhouse that blends classic New England charm with thoughtful, energy-efficient upgrades. Warm wood floors, inviting gathering spaces, updated kitchens and baths, and period details throughout create a home that is both elegant and welcoming. A post and beam three-season room with a hot tub provides the perfect place to unwind while taking in the surrounding landscape. The property also includes a separate three-bedroom guest cottage, ideal for extended family, guests, caretakers, or rental opportunities. For entertaining on a grand scale, the impressive party barn features an expansive gathering space with kitchen facilities, an indoor basketball court, and room for everything from family celebrations to recreation and hobbies. The lower level, once the dairy barn, offers abundant storage for vehicles, recreational equipment, tools, and toys. Equestrian enthusiasts will appreciate the horse stables, fenced pasture areas, and open grounds, while outdoor lovers will enjoy the property's proximity to Lake Raponda, skiing, hiking, snowmobiling, and year-round recreation. Multiple outbuildings and flexible spaces create endless possibilities for agricultural use, workshops, or a private family compound. Whether envisioned as an equestrian estate, multigenerational retreat or four-season Vermont getaway, Green Meadows Farm presents an extraordinary opportunity to own one of the Deerfield Valley's most distinctive properties. See MLS Property & Listing Details & 59 images. Includes a Virtual Tour

New Listing! Wilmington VT Home for sale $$6,898,000 $1,725 per sq.ft.

$6,898,000 $1,725 per sq.ft. Wilmington VT Home »

3 Beds | 6 Baths |   Total Sq. Ft. 4000  |  Acres: 11.2
Tuesday Jul 7, 2026
Description: A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At the heart of the home is a chef's kitchen complete with marble countertops, an oversized center island, walk-in pantry, dual Sub-Zero wine refrigerators, a built-in pizza oven, and a impressive suite of Wolf and Sub-Zero appliances. Designed for year-round enjoyment, the grounds are simply unmatched. Bluestone patios surround the home and lead to a sunken hot tub, cold plunge, a massive BBQ, pergola, children's playscape, and a spectacular post-and-beam open-air pavilion. Gather around the oversized fire pit while enjoying panoramic western sunsets over Haystack Mountain. Private tennis and pickleball courts, complete with a beautifully appointed cabana featuring a half bath, wet bar, and folding glass walls that open directly to the courts. A custom-built carriage house offers four oversized garage bays below for vehicles and seasonal recreational equipment. Above, guests will appreciate a beautifully finished two-bedroom apartment featuring an open-concept kitchen and living area, a gas fireplace, and a full bath--ideal as guest accommodations, an in-law suite, or caretaker's quarters. The professionally landscaped grounds include a paved driveway, beautiful perennial plantings, rolling open field, and stunning views of Haystack Peak. Located just minutes from The Hermitage Club, Mount Snow, golf, skiing, dining, shopping, and all of Southern Vermont's year-round recreational amenities. This is more than a home--it's a legacy estate offering an unparalleled lifestyle where luxury, recreation, and Vermont's natural beauty come together in perfect harmony. See MLS Property & Listing Details & 60 images.

New Listing! Windsor VT Home for sale $$1,399,000 $350 per sq.ft.

$1,399,000 $350 per sq.ft. Windsor VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 4000  |  Acres: 4.96
Tuesday Jun 16, 2026
Description: "The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two porches: one open air and one screened-in, with views into the New Hampshire hillsides. Inside, the house is open and bright with a wonderful flow throughout. The large living room features a wood-burning fireplace and plenty of windows streaming in lots of natural light. The formal dining room, with built-in cabinets and a second wood burning fireplace, connects to the kitchen which is open to the family room. A beautiful spindle staircase with oversized steps leads you upstairs to the four bedrooms, including the primary with an ensuite bath and an attached office. The main guest/children's bedroom features a magnificent turret style sunroom taking in views of the Connecticut River, and a second set of stairs leads back down to the mudroom. The full basement offers plenty of storage and all the utilities. The large 2 story garage offers room for 4 vehicles and plenty of storage on the 2nd floor. This unique property presents a rare opportunity to own a special homestead in the Windsor area, just minutes from downtown shopping and restaurants. See MLS Property & Listing Details & 50 images. Includes a Virtual Tour

$1,100,000 $342 per sq.ft. Winhall VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 4453  |  Acres: 1
Thursday May 21, 2026
Description: Tucked into Stratton Mountain Resort's sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering, relaxing, and enjoying all four seasons in Vermont. Recent exterior improvements have significantly enhanced the home's appearance and overall exterior presentation. Extensive work included reconstruction and upgrading of major exterior sections, along with new windows, roofing, trim, upgraded siding, exterior refinishing, and fresh paint. Complemented by a standing seam metal roof and updated exterior detailing, the home now offers a refreshed mountain exterior with a warm and inviting presence. Inside, the layout is exceptionally functional and inviting. The main level features an open kitchen, dining area, and vaulted living room with fireplace, along with a sunroom, screened porch, stone patio, and private primary suite. A mudroom with half bath off the attached two-car garage adds convenience for ski season and everyday living. Upstairs offers three additional bedrooms, a full bath with double vanity, and an airy loft overlook. The finished walkout lower level is built for entertaining and flexible living, featuring a spacious family room with wood stove and sliders, custom bar area, guest bedroom and bath, additional half bath, laundry, utility areas, and wide hallways throughout. Located just minutes from the slopes, golf course, village, and shuttle access, this is a rare opportunity to own a substantial Stratton mountain home with significant exterior improvements already completed, while still offering the chance to bring your own vision and style to the interior spaces. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour

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