Windham County VT Homes for Sale

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  /16

  $259,900

  • Land
  • 29.2 Acres
  • $8,901 per Acre

  1270 Melendy Hill Rd, Guilford, VT 05301

  A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is

  Christine Lewis Brattleboro Area Realty

  1270 Melendy Hill Rd, Guilford, VT 05301
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  /24

  $28,000

  • 1 Bed
  • 2 Baths
  • 709 Sq Ft

  243/245 qtr 2, Grand Summit Way Unit 243/245, Dover, VT 05356

  TRAILSIDE! A great and affordable opportunity to own the best location to be on the Mount Snow ski trails. Unit 243 boast a queen size Murphy bed, kitchenette and full bath. This unit sleeps 2 and has amazing views of the mountain. Unit 245 has 2 queen beds a full bath, a mini fridge and a private deck overlooking the ski trails. This lockout combination allows you to use the studio and the

  Sheila Joyce-Albano Skihome Realty

  243/245 qtr 2, Grand Summit Way Unit 243/245, Dover, VT 05356
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  /12

  $275,000

  • Land
  • 18.93 Acres
  • $14,527 per Acre

  0 Forest Heights Rd, West Dover, VT 05356

  Are you ready to turn your dream home into a reality? This expansive parcel of land, located just 2 miles from the slopes of Mount Snow, is waiting for your vision. The property offers an ideal combination of privacy and seclusion and with some clearing, you can unveil extraordinary views of the Mount Snow ski slopes, creating the perfect backdrop for your dream home. The property boasts

  Michelle O'Neil Deerfield Valley Real Estate

  0 Forest Heights Rd, West Dover, VT 05356
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  /60

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363

  New Listing in Section C! Quiet corner of the Resort features this Classic Chalet with a mudroom entry, bedroom with slider to the deck, a full bath, open concept kitchen with wood cabinets and breakfast bar, dining area with a bay window, living area with vaulted ceiling, wood burning fireplace and slider to the deck. Upstairs has a full bath with skylight and two bedrooms, one with a skylight

  Sigrid Pickering Chimney Hill Realty

  96 E Brook Crossing Unit CHC209.000, Wilmington, VT 05363
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  /17

  $625,000

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft

  9 Cooper Hill Rd, Dover, VT 05341

  Welcome to your own private sanctuary, tucked away on six stunning acres of unspoiled natural beauty. This inviting 4-bedroom, 2-bathroom home offers the perfect balance of rustic charm and modern comfort, creating an ideal retreat for those seeking peace, privacy, and outdoor adventure.Surrounded by lush woods and open space, the property features a serene private pond, the soothing sounds

  Carrie Mathews Winhall Real Estate

  9 Cooper Hill Rd, Dover, VT 05341
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  /25

  $27,999

  • 2 Beds
  • 2 Baths
  • 745 Sq Ft

  304/306, Qtr 3 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation year-round sound nice? This valley-side lockout unit on the top floor features an open-concept kitchen, dining, and living area with a Murphy bed, as well as a full bath. The adjoining room features two queen beds and an additional full bathroom. The lockout-style unit offers the option of using both sides or using one and renting the other

  Patricia Fitzpatrick Skihome Realty

  304/306, Qtr 3 Grand Summit Way, Dover, VT 05356
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  /40

  $1,695,000

  • 7 Beds
  • 7.5 Baths
  • 8,364 Sq Ft

  251 Pratt Bridge Rd, Jamaica, VT 05343

  Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

  TG Glazer Winhall Real Estate

  251 Pratt Bridge Rd, Jamaica, VT 05343
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  /49

  $625,000

  • 2 Beds
  • 2 Baths
  • 2,144 Sq Ft

  956 Old Cheney Rd, West Townshend, VT 05359

  Experience Vermont living in this beautifully restored 1790 farmhouse, set on 44 acres, gardens, ponds, and stone walls. Just a short drive from Magic Mountain, Grafton Trails, Jamaica State Park, and the iconic Hamilton Falls, this property combines historic character with modern comforts in the heart of southern Vermont.Step inside and discover rich craftsmanship throughout: handmade doors,

  Kim Meeker Southern Vermont Realty Group

  956 Old Cheney Rd, West Townshend, VT 05359
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  /47

  $995,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Welcome to a rare and breathtaking slice of Vermont. This expansive 216-acre farm offers a beautiful mix of open pastures, mature woodlands, fruit trees, berry bushes, and a small section of scenic wetlands – a true haven for nature lovers and outdoor enthusiasts seeking peace and space in every direction. Set along a quiet dirt road near the Massachusetts border, with the added convenience of

  Melissa Nebelski Skihome Realty

  6036 Jacksonville Stage Rd, Guilford, VT 05301
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  /22

  $56,800

  • 3 Beds
  • 3 Baths
  • 1,323 Sq Ft

  157/265/267qtr3 Grand Summit Way Unit 157/265/267, Dover, VT 05356

  TRAILSIDE. Imagine the opportunity of owning a unit at the Grand Summit that can be used as studios that sleep 4, a 1 bedroom sleep 8 or even host 12 guests. Unit 157 sleeps 4 and has a sleep sofa and a Murphy bed, full kitchenette and a full bath. 157 connects via a flight of stairs to unit 267, another studio with a sleep sofa, Murphy bed, kitchenette and full bath, sleeps 4. Unit 265 has 2

  Sheila Joyce-Albano Skihome Realty

  157/265/267qtr3 Grand Summit Way Unit 157/265/267, Dover, VT 05356
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  /35

  $369,000

  • 5 Beds
  • 3 Baths
  • 3,364 Sq Ft

  21 Main St, Saxtons River, VT 05154

  Welcome to history, this 1830's colonial home has so much charm and character to offer! This home is situated in the quaint village of Saxtons River just feet from the Local market store as well as the admired and prestigious Vermont Academy School. With plenty of space to host whether it be in the large grand feeling living room with the original woodwork and fireplaces or the spacious back yard

  Thaddeus Abare Barrett and Valley Associates Inc.

  21 Main St, Saxtons River, VT 05154
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  /34

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,033 Sq Ft

  64 Gleason Farm Ln, Jamaica, VT 05343

  Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner,

  Carrie Mathews Winhall Real Estate

  64 Gleason Farm Ln, Jamaica, VT 05343
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  /35

  $924,900

  • 4 Beds
  • 3.5 Baths
  • 2,272 Sq Ft

  12 Encore Place, Dover, VT 05356

  Mountain Modern Living with unmatched ski views of Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of Carinthia. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the alpine landscape.

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  12 Encore Place, Dover, VT 05356
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  /55

  $640,000

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft

  15 Haymaker Ln Unit 6B, Wilmington, VT 05363

  A Wonderfully well built and maintained spacious Townhome in Desired Powderhorn Condo Association! Nestled in the heart of Vermont’s breathtaking Green Mountains, this beautifully maintained 3-bedroom, 2.5-bathroom condo is your dream getaway. Located just moments from mountain biking, skiing, snowmobiling including VAST trails. Two minutes from 2 world class golf courses and the stunning

  Steve Goldfarb Deerfield Valley Real Estate

  15 Haymaker Ln Unit 6B, Wilmington, VT 05363
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  /5

  $185,000

  • Land
  • 0.84 Acre
  • $220,238 per Acre

  1 Pinnacle View Ln, Dover, VT 05356

  If it's close proximity you want to skiing Mt. Snow then this is your place to build your dream home. Just off a paved road in a small 5 lot subdivision. Underground utilities and sewer hookup available. Convenient to lakes, golf and restaurants, a diamond in the rough. Winter views of Mt. Snow (says owner)

  Regina Perrotto Skihome Realty

  1 Pinnacle View Ln, Dover, VT 05356
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  /21

  $389,000

  • 3 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  5E Polar Bear N, Dover, VT 05356

  Two-bedroom, one sleeping space loft, three-bath townhome in Bears Crossing, located minutes from Mount Snow. This unit includes access to a private Ski Home trail from the slopes and a seasonal shuttle to the mountain. The layout features a ground-level mudroom with bench seating and storage, two bedrooms—including a main-level bedroom with an en suite bath—and an additional full bath. The upper

  Erica Reynolds Southern Vermont Realty Group

  5E Polar Bear N, Dover, VT 05356
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  /43

  $379,000

  • 6 Beds
  • 2 Baths
  • 1,920 Sq Ft

  247 Vt Route 100 N, Wilmington, VT 05363

  Conveniently located on Route 100 between Wilmington Village and Mount Snow. Two separate 3 bedroom, totally renovated, units. This would be a wonderful multi-generational home, two family purchase, use one unit - rent one unit. Wheeler Farm view of pasture and mountain ranges. Exterior garden shed. Plenty of parking, an amazing view and waiting for you!

  Janet Boyd Boyd Real Estate

  247 Vt Route 100 N, Wilmington, VT 05363
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  /6

  $54,500

  • Land
  • 2.4 Acres
  • $22,708 per Acre

  0 Route 30 Unit 5048856, Jamaica, VT 05343

  Tucked along a quiet, town-maintained road in Jamaica, Vermont, this beautifully wooded parcel places you right in the heart of southern Vermont’s legendary ski country. Stratton, Magic, and Bromley Mountains are each only minutes away, giving you three distinct downhill experiences—plus miles of lift-served mountain-bike trails—at your fingertips. Yet winter fun is just the beginning: the West

  Joe Castaluccio Winhall Real Estate

  0 Route 30 Unit 5048856, Jamaica, VT 05343
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  /31

  $947,000

  • 5 Beds
  • 3 Baths
  • 3,015 Sq Ft

  100 Mowing Way, Wilmington, VT 05363

  Impeccably maintained golf course home nestled in the Vermont mountains just 5 miles from lakes, ski resorts, and scenic trails. Perfect for entertaining or quiet enjoyment, this elegant property combines luxury and comfort in a stunning natural setting. The soaring great room features beamed ceilings, radiant heated hickory floors, and a gas fireplace flanked by built ins. A chefs dream kitchen

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  100 Mowing Way, Wilmington, VT 05363
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  /30

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  340 Melendy Hill Rd, Londonderry, VT 05155

  340 Melendy Hill Road, South Londonderry, VT40 Acres | 3 Beds | 2 Baths | Expansive Barn | Mountain ViewsTucked away in the hills of South Londonderry, this charming three-bedroom, two-bath cabin offers the perfect balance of privacy, natural beauty, and quintessential Vermont living. Sited on 40 peaceful acres with sweeping mountain views, the property feels like a private

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  340 Melendy Hill Rd, Londonderry, VT 05155
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  /39

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  156 Mountain View Rd, Wilmington, VT 05363

  This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring bamboo hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  156 Mountain View Rd, Wilmington, VT 05363
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  /39

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft

  256 Potter Rd, Wardsboro, VT 05355

  Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  256 Potter Rd, Wardsboro, VT 05355
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  /31

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,372 Sq Ft

  285 Chimney Hill Rd, Wilmington, VT 05363

  Contemporary retreat in the heart of Chimney Hill. Set on a double lot along a paved road offering the perfect balance of comfort, style and year round convenience. Located just minutes from Wilmington village, Lake Whitingham, Mount Snow and scenic trail that leads to the summit of Haystack Peak in the Green mountain National Forest. The bright, open concept interior is filled with natural

  Monique White Deerfield Valley Real Estate

  285 Chimney Hill Rd, Wilmington, VT 05363
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  /13

  $165,000

  • Land
  • 1.2 Acres
  • $137,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  A Rare Vermont Gem:This 1.2-acre parcel offers what few can—a front-row seat to one of Southern Vermont’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this property is the equivalent of what would be Vermont’s oceanfront real estate.A wooded path leads directly from the land to the pristine falls, which are preserved by the

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  /34

  $125,000

  • Land
  • 1.31 Acres
  • $95,420 per Acre

  118 Chimney Hill Rd, Wilmington, VT 05363

  Brand new Quad Lot right on Chimney Hill Road! Former lots M118 & M119 have had two additional parcels added on each end to form a 1.31-Acre Lot suitable for a three-bedroom single family home. Build your dream home and live the all-season resort lifestyle. Chimney Hill Owners Association is located on 1,200 acres adjacent to the Green Mt. National Forest, with 550 acres owned in common by the

  Sigrid Pickering Chimney Hill Realty

  118 Chimney Hill Rd, Wilmington, VT 05363
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  /21

  $450,000

  • 4 Beds
  • 3.5 Baths
  • 1,800 Sq Ft

  16 Tenth Unit 40, Wilmington, VT 05363

  Beautiful 4 bedroom, 3.5 bath townhouse just off the Hermitage Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club Ski Area and Mount Snow. The deck overlooks the 10th green and is beyond typical driving distance, so you can enjoy the sun while watching play. This unit has been updated including new carpet, new high efficiency wood stove in

  Adam Palmiter Berkley & Veller Greenwood/Dover

  16 Tenth Unit 40, Wilmington, VT 05363
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  /34

  $699,000

  • 3 Beds
  • 4 Baths
  • 3,796 Sq Ft

  233 Poverty Row, Whitingham, VT 05361

  What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, beautiful

  Adam Palmiter Berkley & Veller Greenwood/Dover

  233 Poverty Row, Whitingham, VT 05361
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  /40

  $809,000

  • 3 Beds
  • 3 Baths
  • 3,606 Sq Ft

  46 Scattered Timber Rd, Wilmington, VT 05363

  Escape to the Green Mountains with this custom-built Moose Head Cedar Log Cabin, beautifully sited on a private wooded lot in the sought-after Chimney Hill community. Enjoy ridgeline views, peaceful surroundings, and the fresh Vermont air. Inside, the offers timeless craftsmanship and open-concept living, featuring soaring post and beam construction with vaulted ceilings, floor-to-ceiling windows

  Monique White Deerfield Valley Real Estate

  46 Scattered Timber Rd, Wilmington, VT 05363
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  /36

  $1,690,000

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

  36 A or B Boulder Ridge Dr, Dover, VT 05356

  Brand new luxury townhome with breathtaking Mount Snow & Hermitage Club views. Introducing a newly built, well thought out townhome spanning over 4,300 square feet, perfectly positioned just minutes from Mount Snow and The Hermitage Club. This exquisite residence combines modern mountain living with upscale comfort, offering five spacious bedrooms and five beautifully appointed bathrooms. Step

  John Redd Skihome Realty

  36 A or B Boulder Ridge Dr, Dover, VT 05356
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  /34

  $249,900

  • 2 Beds
  • 1.5 Baths
  • 1,059 Sq Ft

  394 Haystack Rd Unit 2, Wilmington, VT 05363

  Enjoy four-season living in this inviting 2-bedroom, 1.5-bath townhome just a short walk to Haystack Golf Course. Set in a peaceful location with direct Valley Trail and snowmobile access, this well-cared-for home is part of a small HOA with low fees. The main level offers a spacious open layout featuring a cozy wood stove on a slate hearth—perfect for watching the fire roar after a day on the

  Chad Lackey Deerfield Valley Real Estate

  394 Haystack Rd Unit 2, Wilmington, VT 05363
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  /38

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,862 Sq Ft

  161 Depot Rd, Williamsville, VT 05362

  Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive219-acre setting, showcasing a harmonious blend of nature and architecture. This

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  161 Depot Rd, Williamsville, VT 05362
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  /39

  $925,000

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

  9D Dover Springs Ln, Dover, VT 05356

  Stunning updated Greenspring unit, just across the street from the Mount Snow ski resort with stunning direct views of the ski trails. This 4 bedroom, 4 bath unit features extensive upgrades, new furnishings, and immaculate condition, to ensure turn key enjoyment. Features include an open concept great room with vaulted ceiling and wood burning two sided fireplace, sunny exposure and sunset/ski

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9D Dover Springs Ln, Dover, VT 05356
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  /2

  $175,000

  • Land
  • 8.52 Acres
  • $20,540 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
• 

  /2

  $125,000

  • Land
  • 14.91 Acres
  • $8,384 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
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  /28

  $1,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,476 Sq Ft

  3B Freestyle Cir, Dover, VT 05356

  Trailside luxury at the base of the Mount Snow ski resort just off the Snowdance ski trail. This spectacular 2016 unit is just about as close and turn key as you can find. Amazing convenience to the mountain thanks to direct ski trail access, affording the ability to stop by to warm up or get a bite, yet with easterly views and a size usually only found in off mountain properties. The large

  Adam Palmiter Berkley & Veller Greenwood/Dover

  3B Freestyle Cir, Dover, VT 05356
• 

  /2

  $225,000

  • Land
  • 9.45 Acres
  • $23,810 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
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  /46

  $940,000

  • 3 Beds
  • 4.5 Baths
  • 3,318 Sq Ft

  42 Sugar House Rd, West Dover, VT 05356

  Tucked into the serene hills of Dover, Vermont, this custom crafted mountain home offers the ideal blend of rustic charm and modern comfort just minutes from Mount Snow and The Hermitage Club. Set on a private lot with winter views of both ski mountains, this 3-bedroom(+bonus bedroom), 4.5-bath home features an open-concept layout with soaring cathedral ceilings, exposed beams, and a stunning

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  42 Sugar House Rd, West Dover, VT 05356
• 

  

  /11

  $250,000

  • Land
  • 18 Acres
  • $13,889 per Acre

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

  Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

  Christine Lewis Brattleboro Area Realty

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
• 

  

  /6

  $795,000

  • 3 Beds
  • 2 Baths
  • 1,267 Sq Ft

  635 Vermont Route 100, Wardsboro, VT 05355

  Great short term or long term rental for investment or use by a large family. Rent one and enjoy the other. Located 1.6 miles north of Mt. Snow with direct access to VAST from this property. This home was renovated in 2014 including a new roof, windows and doors. Current owners replaced hot tub 2 years ago and a tankless water heater 3 years ago. THIS PROPERTY IS ALSO BEING SOLD WITH LISTING

  Ginny Read Read Realty LTD

  635 Vermont Route 100, Wardsboro, VT 05355
• 

  

  /8

  $795,000

  • 4 Beds
  • 3 Baths
  • 2,142 Sq Ft

  633 Route 100, West Wardsboro, VT 05360

  Great short or long term rental for investment or use by a large family. Rent one and enjoy the other. Located 1.6 miles north of Mount Snow and with direct access to VAST from this property. This home was renovated in 2014 including new ro0f, windows & doors. Current owners replaced the hot tub 1 year ago and the tankless water heater 3 years ago. Being sold furnished and ready for family,

  Ginny Read Read Realty LTD

  633 Route 100, West Wardsboro, VT 05360

Showing Results 241 - 280, Page 7 of 11