Windham County VT 3-Story Homes for Sale

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  /58

  $720,000

  • 4 Beds
  • 3 Baths
  • 4,379 Sq Ft

  587 Vermont 121, Grafton, VT 05146

  The Woolley House, located at 587 Route 121 East and built around 1818, is a rare and remarkably preserved 2.5 story brick residence in the Federal style. This home, originally constructed for early woolen mill owner John Woolley, features a side-hall layout, blind-arch entryway, and fanlight transom.Original details are beautifully preserved throughout, including four elegant Regency

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /44

  $530,900

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  37B Kingswood Rd, Dover, VT 05356

  Refined mountain luxury meets effortless four-season living in this impeccable Kingswood townhome, offering direct snowmobile trail access and private shuttle service to Mount Snow. Ideally positioned on the level portion of the development, this exceptional four-bedroom residence enjoys convenient trail access and a more expansive, usable, level rear yard—a rare and highly sought-after offering

  Michelle O'Neil Deerfield Valley Real Estate

  37B Kingswood Rd, Dover, VT 05356
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  /31

  $399,000

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

  459 Silver Ln, Wardsboro, VT 05355

  Come and visit your potential get away in the much sought after development of Snow Mountain Farms in Wardsboro, VT. This community offers an indoor swimming pool, tennis courts and an exercise facility for an extremely modest fee. A three-bedroom, one bonus room home has the perfect balance of Vermont charm and comfort for you and your guests. With recently installed floors and all new

  Peggy O'neill Cummings & Co

  459 Silver Ln, Wardsboro, VT 05355
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  /36

  $1,590,000

  • 5 Beds
  • 4.5 Baths
  • 4,325 Sq Ft

  19 Boulder Ridge Dr Unit 19 B, Dover, VT 05356

  Once in a while, a property comes along that truly leaves you speechless — and this is one of those rare moments. This 5-bedroom, 4.5-bath Boulder Ridge townhome has been meticulously renovated with precision and style at every turn. This is not the Boulder Ridge you've known before, and it's being offered completely turn-key.This immaculate unit sits in an ideal location with unobstructed

  Adam Palmiter Berkley & Veller Greenwood/Dover

  19 Boulder Ridge Dr Unit 19 B, Dover, VT 05356
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  /40

  $4,087,000

  • 6 Beds
  • 7 Baths
  • 7,090 Sq Ft

  22 Stags Leap Ln, Wilmington, VT 05363

  Spectacular custom home at the base of the Hermitage Club in the Stags Leap community, adjacent to the ski trails at the base of Haystack mountain. This is a rare lot overlooking the trails, with direct ski-on/off and lift access, mountain views, and sunsets beyond, unimpeded by any other homes. Featuring 6 bedrooms, 5 and two half baths, with luxurious high ceiling great room with exposed

  Adam Palmiter Berkley & Veller Greenwood/Dover

  22 Stags Leap Ln, Wilmington, VT 05363
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  /26

  $899,000

  • 3 Beds
  • 3.5 Baths
  • 1,730 Sq Ft

  1C Townhouse Square Unit 7, Dover, VT 05356

  Experience true ski-in/ski-out living at Mount Snow in the highly desirable Seasons on Mount Snow community - on Tin Lizzy, and just seconds to the lift. This spacious 3-bedroom, 3.5-bath townhouse offers a thoughtful and functional layout, including two private en suite bedrooms for added comfort and flexibility. Two separate living areas provide ample space for entertaining and relaxing, while

  Stephanie Sugden Real Broker LLC

  1C Townhouse Square Unit 7, Dover, VT 05356
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  /21

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,778 Sq Ft

  28 Summit Meadows Cir, Dover, VT 05356

  Lovely updated contemporary chalet nestled at the base of the Dover Hills in the village of Dover, just a short drive from the Mount Snow ski resort. This convenient location affords the privacy of a home, but much easier access, and proximity to amenities, dining, shopping, and more. At the end of a loop, this home sits on a private and quiet parcel with a nice buffer of trees, level lawn, stone

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Summit Meadows Cir, Dover, VT 05356
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  /33

  $349,000

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  29 Pikes Falls Rd, Jamaica, VT 05343

  Experience the timeless appeal of this beautifully preserved 1800s Greek Revival residence in the center of Jamaica Village. Offering more than 2,500 square feet of living space, the home pairs classic architectural detail with thoughtful modern updates for effortless year-round living.Ideally situated just 15 minutes from Stratton Mountain and 25 minutes to Mount Snow, the location balances

  Carrie Mathews Winhall Real Estate

  29 Pikes Falls Rd, Jamaica, VT 05343
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  /43

  $799,000

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

  39D Dover Springs Ln, Dover, VT 05356

  Located in the highly sought-after Greensprings community at Mount Snow, this spacious 4 bedroom, 4 bath townhouse offers the perfect blend of comfort, convenience, and year-round recreation.The bright, open-concept main living area features vaulted ceilings, abundant natural light, and a cozy fireplace ideal for gathering after a day on the slopes. Large windows and sliding doors invite the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  39D Dover Springs Ln, Dover, VT 05356
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  /39

  $1,750,000

  • 7 Beds
  • 5 Baths
  • 4,649 Sq Ft

  4669 Vermont Route 100, Londonderry, VT 05148

  Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with

  Story Jenks LandVest, Inc/Woodstock

  4669 Vermont Route 100, Londonderry, VT 05148
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  /60

  $749,000

  • 4 Beds
  • 4 Baths
  • 2,964 Sq Ft

  16 Rock Split Way, Wilmington, VT 05363

  Turnkey mountain retreat with style, space, and serious four-season fun—welcome to Chimney Hill living at its best. This beautifully crafted 4 bedroom home offers 4 full tiled baths and approximately 3,000 sq ft of warm, inviting living space on 3 levels designed for gathering, relaxing, and making memories. The open concept main level delivers instant wow factor with soaring cathedral ceilings,

  Chad Lackey Deerfield Valley Real Estate

  16 Rock Split Way, Wilmington, VT 05363
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  /18

  $309,000

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  61C Country Club Rd, Dover, VT 05356

  Arrive, exhale, and settle into a condo that lives like a true getaway. This light-filled, spacious residence pairs a large open kitchen and dining area with a comfortable living room featuring a wood stove for cozy winter nights after a long day on the slopes! Inside, you will find 3 bedrooms, 3 bathrooms, and 1,440 sq ft designed for relaxed hosting and easy retreat. The open-concept main level

  Patricia Fitzpatrick Skihome Realty

  61C Country Club Rd, Dover, VT 05356
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  /26

  $625,000

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft

  68 Ellis Brook Rd, Dover, VT 05341

  Gorgeous updated chalet on a private 2-acre parcel with mountain views and easy access to Mount Snow. Nestled in the desirable Dover Hills, this charming country retreat offers privacy befitting a year-round getaway, yet is just a short drive to the Mount Snow ski resort. Ample parking off a paved road, generous lawn space for play or pets, a garden shed, and excellent sun exposure complete the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 Ellis Brook Rd, Dover, VT 05341
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  /36

  $799,000

  • 4 Beds
  • 4 Baths
  • 3,691 Sq Ft

  42 Airport Rd, Shaftsbury, VT 05262

  Set just minutes from world class skiing at Mount Snow, this inviting timber frame home offers comfort, convenience, and year-round adventure right outside your door. Located just off the Mount Snow Golf course and with direct access to VAST snowmobile trails, this property is perfectly positioned for ski weekends, snowmobiling adventures, summer hiking, and everything in between. Inside, you’ll

  Mike Masters Four Seasons Sotheby's Int'l Realty

  42 Airport Rd, Shaftsbury, VT 05262
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  /29

  $569,000

  • 4 Beds
  • 3 Baths
  • 2,050 Sq Ft

  39B Kingswood Rd, Dover, VT 05356

  An impeccably maintained, beautifully furnished, and recently painted Kingswood townhome is conveniently located just minutes from Mount Snow and the Hermitage Club. This townhome features four bedrooms; an open-concept living area on the main level; a kitchen with a large island, granite countertops, and a vaulted ceiling; a wood-burning fireplace; and sliding doors leading to a private deck

  Patricia Fitzpatrick Skihome Realty

  39B Kingswood Rd, Dover, VT 05356
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  /31

  $539,000

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  72A Kingswood Rd, Dover, VT 05356

  Meticulously updated and maintained Kingswood townhome with direct snowmobile trail access and shuttle service to Mount Snow. This uniquely private four-bedroom unit is ideally positioned on the lower side of the development, offering greater separation between units, easy trail access, and a more usable private rear yard. The home features an open-concept living space with vaulted ceilings, a

  Adam Palmiter Berkley & Veller Greenwood/Dover

  72A Kingswood Rd, Dover, VT 05356
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  /60

  $8,200,000

  • 6 Beds
  • 10 Baths
  • 10,763 Sq Ft

  557 Trager Rd, Jamaica, VT 05343

  Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in

  Kim Morgan-Wohler Wohler Realty Group

  557 Trager Rd, Jamaica, VT 05343
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  /38

  $1,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,965 Sq Ft

  26 Springhill Rd, Dover, VT 05301

  This spectacular Post & Beam home is located just off the 13th hole of the Mount Snow Golf Course just minutes from the Mount Snow ski area. Nestled in a quiet community, with tremendous curb appeal, enjoy year round enjoyment thanks to the adjacent course, for obvious summer fun, but also snowshoeing and hiking in the winter. The interior of the home is about as good as it gets when looking for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  26 Springhill Rd, Dover, VT 05301
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  /27

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,306 Sq Ft

  32 Old Town Rd, Dover, VT 05356

  Lovely mountain and sunset views from this absolutely immaculate home just south of the Mount Snow ski resort. Enjoy total privacy yet easy access to skiing, direct access to snowmobile trails, and nearby access to the villages of Wilmington and Dover for shopping and dining. The property consists of a level 2 acres with swimming pond, lawn space for summer fun, stone patio, storage shed, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  32 Old Town Rd, Dover, VT 05356
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  /48

  $294,000

  • 5 Beds
  • 3 Baths
  • 2,360 Sq Ft

  5 Reynolds Dr, Brattleboro, VT 05301

  Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers a rare "move-in ready" opportunity for both savvy investors and owner-occupants. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. With new toilets and stainless/modern

  Kate Barry EXP Realty

  5 Reynolds Dr, Brattleboro, VT 05301
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  /31

  $459,000

  • 1 Bed
  • 2.5 Baths
  • 2,076 Sq Ft

  33 W Main St, Wilmington, VT 05363

  Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or

  Adam Palmiter Berkley & Veller Greenwood/Dover

  33 W Main St, Wilmington, VT 05363
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  /41

  $529,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  19B Kingswood Rd, Dover, VT 05356

  Beautiful 3-bedroom, 3 bath Kingswood townhouse ideally located between Mount Snow and Hermitage Club. This Kingswood townhouse offers the perfect mountain getaway. Enjoy the well-appointed kitchen with a center island, a bright dining area, and a living area with a vaulted ceiling and a stunning 3 sided wood-burning fireplace, creating a warm, inviting atmosphere. Step outside onto a private

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  19B Kingswood Rd, Dover, VT 05356
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  /23

  $679,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  14A Grouse Ln Unit 14A, Dover, VT 05356

  Gorgeous Post and Beam style townhome overlooking spectacular views of the Hermitage Club ski trails and sunsets over the ridgeline. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, easy nearby access to the Mount Snow ski resort, hiking and biking trails in the summer, and nearby convenience to the area's numerous lakes, dining and shopping.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14A Grouse Ln Unit 14A, Dover, VT 05356
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  /37

  $749,000

  • 3 Beds
  • 3.5 Baths
  • 2,842 Sq Ft

  43C Dover Springs Ln, Dover, VT 05356

  This Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A meticulously maintained 3 bedroom, 3.5 bath unit with lots of bonus space, some recent updates and unique features. These include an open concept great room with vaulted ceilings, sunny natural light and sunset/ski trail views, wood burning double sided fireplace,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  43C Dover Springs Ln, Dover, VT 05356
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  /37

  $939,000

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft

  25 Boulder Ridge Dr Unit B, Dover, VT 05356

  This magnificent 4-bedroom, 4-bathroom townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design, offering a living experience par excellence. This townhouse was finished in 2021 and has the “new construction” feel. The living room, graced with hardwood flooring, a gas fireplace,

  John Redd Skihome Realty

  25 Boulder Ridge Dr Unit B, Dover, VT 05356
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  /27

  $949,000

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft

  15 Boulder Ridge Dr, Dover, VT 05356

  Spectacular ski trail and half pipe views from this beautiful 2008 4 bedroom townhome across from the Mount Snow ski resort with easy shuttle access. This immaculate unit and is truly ready for turn key enjoyment. Inside you are treated to a vaulted great room with floor to ceiling stone fireplace, tremendous natural light, south facing exposure, and direct ski area views with sunsets beyond, an

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Boulder Ridge Dr, Dover, VT 05356
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  /41

  $899,000

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

  9 Windham Way, Dover, VT 05356

  This upgraded new style Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A well updated 4+ bedroom, 4 bath unit with lots of bonus space, many recent updates and unique features. These include an open concept great room with vaulted ceiling, sunny exposure and sunset/ski trail views, wood burning fireplace unique against

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9 Windham Way, Dover, VT 05356
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  /17

  $449,000

  • 3 Beds
  • 3 Baths
  • 1,726 Sq Ft

  4A Suntec Loop Unit 4A, Dover, VT 05356

  Beautiful woodsy Suntec townhome just down from the base of the Mount Snow ski resort. This spacious 3 bedroom plus loft townhome sits about a mile south of Mount Snow, with direct access to snowmobile trails, and easy access to the nearby village of Wilmington and lakes. The unit has a large open concept floor plan with living room with wood burning fireplace and brick hearth, rustic wood

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4A Suntec Loop Unit 4A, Dover, VT 05356
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  /21

  $489,000

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  12 Lilla Ln, Wilmington, VT 05363

  Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

  Adam Palmiter Berkley & Veller Greenwood/Dover

  12 Lilla Ln, Wilmington, VT 05363
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  /33

  $2,100,000

  • 7 Beds
  • 4 Baths
  • 4,256 Sq Ft

  121 Fannie Hill Dr, Wilmington, VT 05363

  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

  Adam Palmiter Berkley & Veller Greenwood/Dover

  121 Fannie Hill Dr, Wilmington, VT 05363
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  /54

  $3,750,000

  • 6 Beds
  • 6.5 Baths
  • 5,660 Sq Ft

  168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360

  Experience true mountain luxury in this stunning six bedroom six bathroom slope side single family home, perfectly positioned for effortless access to world-class skiing and snowboarding at the Stratton Mountain Resort. Designed with comfort and style in mind, this residence combines refined alpine architecture with modern amenities including a gym, steam shower, pool table that doubles as table

  Timothy Mich Doddridge Stratton Real Estate

  168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360
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  /54

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 4,040 Sq Ft

  17 Boulder Ridge Dr Unit A, Dover, VT 05356

  This magnificent 5-bedroom, 4.5-bath townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design. The living room, graced with hardwood (hickory) flooring, a gas fireplace, large windows, a slider to the deck with an amazing view of Mount Snow, and a vaulted ceiling, creates an ambiance

  John Redd Skihome Realty

  17 Boulder Ridge Dr Unit A, Dover, VT 05356
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  $1,470,000

  • 5 Beds
  • 4.5 Baths
  • 5,160 Sq Ft

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Perched on scenic Cobble Ridge, this custom five-bedroom, four-and-a-half-bath retreat embodies balance, light, and renewal in the heart of Southern Vermont. Set on seven private, fenced acres framed by stone walls and dual gated entries, the property enjoys southwest exposure with soft, filtered ridgeline views that evolve beautifully through the seasons. Inside, a brick fireplace anchors the

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148
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  /24

  $849,000

  • 4 Beds
  • 2 Baths
  • 1,638 Sq Ft

  12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360

  Unmatched Comfort and Convenience at Stratton's Ober Tal – Walk to Lift Discover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Just a short walk to the Tamarack ski lift, you’ll enjoy unbeatable access to the slopes and all the amenities in Stratton Village. Close enough to swing back for a quick lunch, this condo lets you make the most of your

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360
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  /51

  $949,000

  • 4 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  33 Carinthia Rd, Dover, VT 05356

  LOCATION, LOCATION, LOCATION!! 3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces, and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood-burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral

  Jacki Murano Southern Vermont Realty Group

  33 Carinthia Rd, Dover, VT 05356
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  /3

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  2173 Vermont 8a, Whitingham, VT 05361

  4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

  Mark Yule BHG Masiello Brattleboro

  2173 Vermont 8a, Whitingham, VT 05361
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  /32

  $675,000

  • 3 Beds
  • 3 Baths
  • 2,216 Sq Ft

  12 Three Streams Way, Wilmington, VT 05363

  Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

  Tamara Purcell Berkley & Veller Greenwood Country

  12 Three Streams Way, Wilmington, VT 05363
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  /32

  $559,000

  • 3 Beds
  • 3 Baths
  • 2,080 Sq Ft

  9 Greer Ct, Wilmington, VT 05363

  Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9 Greer Ct, Wilmington, VT 05363
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  /29

  $1,249,000

  • 4 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  3F Slalom Dr, Dover, VT 05356

  Just steps from the Mount Snow ski trail, this impeccably maintained 3,500 square foot luxury townhome is located in TrailsEdge, Mount Snow's exclusive ski-on/off community. Never again fight the traffic or pay for parking in the main base area when you can ski to and from your front door! As an end unit, this four-bedroom, 5-bath furnished townhome is a testament to luxury, with radiant heat

  Patricia Fitzpatrick Skihome Realty

  3F Slalom Dr, Dover, VT 05356
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  /26

  $740,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  8 Grouse Ln, Dover, VT 05356

  Escape to 8A Grouse Lane at Mount Snow, where timeless post-and-beam character meets modern comfort in a setting designed for all four seasons. This beautifully reimagined end-unit townhome was thoughtfully redesigned to create an open, inviting living space, complete with a striking gas-burning fireplace—the perfect spot to gather after a day on the mountain. Wake up to ridge-line views, sip

  Wilkie Bushby TPW Real Estate

  8 Grouse Ln, Dover, VT 05356

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