Windham County VT Homes for Sale

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  /17

  $35,000

  • Land
  • 2.5 Acres
  • $14,000 per Acre

  123 U S 5, Westminster, VT 05158

  This 2.5 acre lot offers a level parcel of land ready for your plans. The wooded lot is composed of immature growth, easing the task of clearing a dwelling/structure site while maintaining trees for privacy. The eastern, road-side section of the parcel can be opened to a lovely view over the NH horizon. Soil testing available and possible septic areas sited. See photos and listing documents.

  Laura D'Angelo Berkley & Veller Greenwood Country

  123 U S 5, Westminster, VT 05158
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  /60

  $319,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  3185 Higley Hill Rd, West Marlboro, VT 05363

  Vermont A-Frame Retreat in Marlboro! Escape to this charming 2-bedroom, 2-bath A-frame set on 2.18 wooded acres in scenic Marlboro, Vermont. With a stream, deck, and peaceful natural setting, this property offers the perfect blend of privacy and character. Inside, you’ll find 1,164 square feet of furnished living space featuring natural light, a wood fireplace, first-floor laundry, and a

  Flex Realty Group Flex Realty

  3185 Higley Hill Rd, West Marlboro, VT 05363
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  /21

  $179,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  40 Brookside Dr Unit 8, Brattleboro, VT 05301

  Don't wait to come view this newly remodeled, low maintenance, affordable and desirable ground floor end unit. Inviting circular flow, the spacious living room has a brand new slider with a view of the rear yard and the Whetstone brook. Plus, you have a brand new kitchen and appliances. The large bedroom with double closet has direct access to the newly renovated bath. This condo is located in a

  Angela Sherman Brattleboro Area Realty

  40 Brookside Dr Unit 8, Brattleboro, VT 05301
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  /27

  $379,000

  • 4 Beds
  • 3 Baths
  • 1,720 Sq Ft

  292 Tallwood Cir, Londonderry, VT 05148

  Welcome to this charming chalet in the Sherwood Forest neighborhood of Londonderry! Come inside to a bright, open great room featuring living and dining areas, large windows, a cozy wood stove, and a breakfast bar that connects seamlessly to the kitchen. This inviting home is the perfect Vermont getaway for you or your guests. Just off the great room, the classic country kitchen offers an ideal

  The Malley Group KW Vermont

  292 Tallwood Cir, Londonderry, VT 05148
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  /48

  $350,000

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  106 Main St Unit 5, Putney, VT 05346

  Bright, airy, and full of personality, this charming two-bedroom, one-bathroom condo in the Village of Putney offers comfort, style, and convenience. Ideally located just minutes from I-91 and close to Putney’s vibrant downtown shops, cafés, and everyday amenities, this condo offers easy access to village life. Inside, natural light fills the thoughtfully designed space, highlighting dreamy

  Rebecca Hiam Southern Vermont Realty Group

  106 Main St Unit 5, Putney, VT 05346
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  /38

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  527 Route 121, Bellows Falls, VT 05101

  Move-in ready gutted and renovated home on 1.5 acres. New roof and new propane baseboard furnace and hot water system. New appliances. Insulated two-car garage. Beautiful mountain views.

  David White OwnerEntry.com

  527 Route 121, Bellows Falls, VT 05101
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  /32

  $229,000

  • 1 Bath
  • 475 Sq Ft

  11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356

  Discover effortless mountain living in this beautifully updated studio condominium that is walking distance to the slopes and in the desirable Snow Tree community. Perfect for weekend getaways, seasonal escapes, or as a high performing rental investment. This home boasts an extremely strong rental history supported by a documented 3 year history of over $25,000 annually and is being offered fully

  Melissa Ellis Southern Vermont Realty Group

  11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356
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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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  /43

  $1,300,000

  • 3 Beds
  • 4 Baths
  • 2,944 Sq Ft

  156 W Lake Rd, Wilmington, VT 05363

  A rare opportunity to own a beautifully maintained, one-family-owned home on Lake Raponda. Lovingly cared for through the years. This special waterfront property offers the perfect blend of comfort, warmth, and classic Vermont charm. Spend your days boating, kayaking, swimming, or simply relaxing by the shore, and unwind in the quiet beauty that makes Lake Raponda so special. Step inside to an

  Jillian Wimmelman Deerfield Valley Real Estate

  156 W Lake Rd, Wilmington, VT 05363
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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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  /32

  $549,000

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  13 Yodeling Ln, Dover, VT 05356

  Tremendous opportunity to own an updated A-frame chalet at the base of Mount Snow ski resort and the Carinthia Freestyle Terrain Park. This lovely Vermont home sits nestled on a quiet loop just south of the mountain, with direct walking and hiking trail access.The open floor plan features an updated kitchen with stainless appliances, copper counters, and a vent hood, along with a living room

  Adam Palmiter Berkley & Veller Greenwood/Dover

  13 Yodeling Ln, Dover, VT 05356
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  /49

  $699,900

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  300 Route 121 E, Grafton, VT 05146

  Nestled in a postcard-perfect setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Set on over two park-like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle.Inside, you’ll find a spacious eat-in kitchen with abundant counter space and

  Gary Coger Four Seasons Sotheby's Int'l Realty

  300 Route 121 E, Grafton, VT 05146
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  /31

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  28E Crosstown Rd, Dover, VT 05356

  This beautifully decorated, turnkey three-level end-unit townhome offers the perfect year-round mountain retreat. Ideally located just minutes from Mount Snow Ski Resort and only half a mile from the Mount Snow Golf Course and the scenic Valley Trail, you’ll enjoy easy access to outdoor recreation in every season.The open-concept main living area is designed for comfort and entertaining,

  Patricia Fitzpatrick Skihome Realty

  28E Crosstown Rd, Dover, VT 05356
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  /37

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,070 Sq Ft

  239 Valley View Rd, Dover, VT 05356

  This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  239 Valley View Rd, Dover, VT 05356
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  /58

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,772 Sq Ft

  7 Grassy Brook Rd, Brookline, VT 05345

  Incredible Opportunity! This fully renovated, move-in ready retreat is perfectly situated on the picturesque West River. Enjoy your own private beach and waterfront lifestyle at its finest. Whether you’re seeking a peaceful getaway, a year-round residence, or an investment property with proven short-term rental history, this home checks every box. Inside, the property has been thoughtfully

  Flex Realty Group Flex Realty

  7 Grassy Brook Rd, Brookline, VT 05345
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  /26

  $395,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  135 Country Hill, Brattleboro, VT 05301

  Built in 2004 in this much-loved neighborhood, on a desirable one-way cul-de-sac, beautifully maintained, sits this 3-bedroom, 3-bath home. The first floor has a beautiful, large, eat-in kitchen, dining room, 1/2 bath, and access to a very spacious and inviting 16x16 deck ideal for family gatherings or entertaining, and a real sense of privacy. On the second floor, there is a primary bedroom with

  Neil Goldberg Brattleboro Area Realty

  135 Country Hill, Brattleboro, VT 05301
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  /32

  $479,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1 Brookside Village Way Unit M22, Dover, VT 05356

  Amazing trailside, completely renovated end unit opportunity at Mount Snow. This is a beautiful and bright 2 bedroom, 2 bath unit, located adjacent to the ski-on/ski-off trail for absolutely the easiest access you can enjoy. Each unit has a ground floor ski locker to stow your gear, and then you are only a half flight up to make for easy access after a day of skiing. Enjoy the spacious living

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1 Brookside Village Way Unit M22, Dover, VT 05356
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  /34

  $95,000

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

  169 Sun and Ski Rd, Wilmington, VT 05363

  Dreaming of building a home in Vermont but not sure where to start? With several significant steps in the preparation process already done, this one-acre lot is truly ready for your vision. A three-bedroom septic design by a Vermont engineer has been completed, with permits filed and approved by the state of Vermont. Plus, the land has already been partially cleared for a driveway and building

  Kim Meeker Southern Vermont Realty Group

  169 Sun and Ski Rd, Wilmington, VT 05363
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  /9

  $198,000

  • Land
  • 0.73 Acre
  • $271,233 per Acre

  5 Pinnacle View Rd, Dover, VT 05356

  With views of Mount Snow, this exceptional 0.73-acre parcel is the perfect setting for your dream mountain retreat. Located in the resort district, short-term rentals are permitted, making this a prime investment opportunity or an ideal family legacy home for generations to enjoy. Just off Route 100, a one-minute drive to the lifts at Mount Snow,an Epic Pass mountain, offering world-class skiing

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  5 Pinnacle View Rd, Dover, VT 05356
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  /60

  $489,000 Open House 4/11

  • 4 Beds
  • 3.5 Baths
  • 2,312 Sq Ft

  23 Wilsons Woods Rd, Brattleboro, VT 05301

  Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro’s vibrant restaurants, local shops, the hospital, and a thriving

  Kate Barry EXP Realty

  23 Wilsons Woods Rd, Brattleboro, VT 05301
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  /43

  $799,000

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

  1 Lower Highlands Rd, West Dover, VT 05356

  Custom-built 4-bedroom, 2.5-bath home ideally located less than a mile from Mount Snow. The main level welcomes you with an inviting foyer off the covered front porch and offers a well-designed layout featuring a spacious living room, formal dining room, comfortable family room, versatile den, and a well-appointed kitchen. Additional conveniences include a half bath, dedicated laundry area, and a

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1 Lower Highlands Rd, West Dover, VT 05356
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  /29

  $699,995

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

  152 Main St, Grafton, VT 05146

  Newly renovated home located in the heart of Grafton Village! This home features 4 spacious bedrooms, and 2 full baths. Large primary bedroom suite located on the first floor of the home with working fireplace and private bathroom. Brand new kitchen with all new cabinetry, quartz countertops and stainless steel appliances. Original hardwood floors, moldings and original doors. All brand new

  Derek Greene Derek Greene

  152 Main St, Grafton, VT 05146
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  /35

  $350,000

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft

  6795 Vt Route 100, Londonderry, VT 05148

  Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses –whether you’re looking to

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  6795 Vt Route 100, Londonderry, VT 05148
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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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  /20

  $400,000

  • 3 Beds
  • 2 Baths
  • 1,599 Sq Ft

  175 Sak Rd, Vernon, VT 05354

  This is it!!!! One level living with a bonus room and bath in the lower level for a bit of get away family room living. Perfect for downsizing or just beginning. Professional builder has taken this home to a brand new level, adding a living room with vaulted ceilings, wall of windows and a slider to a lovely back deck. The lot is level and sunny enough for a garden, and crosses the Sak Brook with

  Christine Lewis Brattleboro Area Realty

  175 Sak Rd, Vernon, VT 05354
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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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  /26

  $500,000

  • Land
  • 71 Acres
  • $7,042 per Acre

  00 Turkey Mountain Rd, Jamaica, VT 05343

  Escape to your own private 71-acre Vermont retreat, offering exceptional privacy and possibility plus access to nearby ski mountain villages. Tucked at the end of a town-maintained dead-end road and bordered on two sides by over 1,000 acres of conservation land, this property promises unmatched peace and lasting protection. Only 20 minutes to either Mt. Snow or Stratton, with over 3,300 feet of

  Jessica Landers Barrett and Valley Associates Inc.

  00 Turkey Mountain Rd, Jamaica, VT 05343
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  /32

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  15 Bears Den Rd, Dover, VT 05356

  A rare opportunity to enjoy the best of both worlds — the privacy of a single-family home with the convenience and access of condo-style living. This unique vacation home offers direct ski-home access in the sought-after Bears Crossing community on the slopes of Mount Snow. Ski back from the Carinthia trails and step out of your gear just across the street from your front door. Designed with both

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Bears Den Rd, Dover, VT 05356
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  /34

  $269,000

  • 1 Bed
  • 1 Bath
  • 2,000 Sq Ft

  116 Birge St Unit 3, Brattleboro, VT 05301

  Huge price reduction! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings,

  Liz LaVorgna Brattleboro Area Realty

  116 Birge St Unit 3, Brattleboro, VT 05301
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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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  /32

  $239,000

  • 2 Beds
  • 1.5 Baths
  • 1,160 Sq Ft

  11 Hassey Bend Unit 9, Wilmington, VT 05363

  Ready to move in Mountain Ponds end unit Townhouse with 2 bedroom plus loft and 1 1/2 bathsMain level boasts an open concept living/dining and renovated kitchen area. Relax on the back deck off dining area. Gas stove in the living room. Attached ski locker/wood bin with 2 entrances. Spacious mudroom. Direct access to VAST snowmobile trail and adjacent to Haystack Golf Course. Lake Whitingham is

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  11 Hassey Bend Unit 9, Wilmington, VT 05363
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  /27

  $380,000

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  34 Main St, Wardsboro, VT 05355

  Lovely late 1800s farmhouse conveniently located in the village of Wardsboro, Vermont, just a short drive to both Mount Snow and Stratton ski resorts. Meticulously maintained, the home sits on a well-positioned parcel with ample parking, private lawn space, and direct snowmobile trail access, plus easy walking access to the nearby convenience store for everyday necessities. Inside, the home

  Adam Palmiter Berkley & Veller Greenwood/Dover

  34 Main St, Wardsboro, VT 05355
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  /13

  $120,000

  • Land
  • 4.68 Acres
  • $25,641 per Acre

  8559 Vt Route 30, Jamaica, VT 05343

  Double the Lots, Half the Drama.Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend who always "forgets" their

  TG Glazer Winhall Real Estate

  8559 Vt Route 30, Jamaica, VT 05343
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  /37

  $36,500

  • 2 Beds
  • 2 Baths
  • 878 Sq Ft

  313 Qtr.1, 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Mountainside two bedroom sleep 6 unit with a covered balcony. Kitchen, living room and queen sleeper sofa as well as a king bed in private bedroom on the first floor. Full bath with double sink vanity on the first floor. Lofted bedroom also has a king bed and a 3/4 bath . Benefits of Grand Summit ownership include the best

  Kelly Agrillo Southern Vermont Realty Group

  313 Qtr.1, 89 Grand Summit Way, Dover, VT 05356
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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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  /36

  $39,900

  • 2 Beds
  • 3 Baths
  • 1,008 Sq Ft

  320 322 Qtr1 89 Grand Summit Way Unit 320 322, Dover, VT 05356

  Quarter share (deeded interval 1) ownership at the Grand Summit at the base of Mount Snow, offering 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. Experience the mountain resort lifestyle affordably!! This 2-bedroom, 3-bath unit is located on the third floor and on the valley side of the hotel and sleeps eight with 1008 sq ft. Unit 322

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  320 322 Qtr1 89 Grand Summit Way Unit 320 322, 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
• 

  

  /27

  $33,900

  • 1 Bed
  • 2 Baths
  • 771 Sq Ft

  235/237, QTR 2 89 Grand Summit Way, Dover, VT 05356

  Own Where You Play! One-of-a-kind sleep eight quartershare, featuring a gas fireplace, updated decor and furnishings, plus gorgeous mountain views, this is a rare find in the Grand Summit Resort Hotel! This comfortable condo has two full baths and a lockout feature, with an adjoining door within the unit, so you can use it, rent it, or trade it for a timeshare vacation simultaneously! Overlooking

  Patricia Fitzpatrick Skihome Realty

  235/237, QTR 2 89 Grand Summit Way, Dover, VT 05356
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  /31

  $37,500

  • 2 Beds
  • 2 Baths
  • 914 Sq Ft

  311 Qtr 3 Grand Summit Way, Dover, VT 05356

  Beautiful mountain view from this two-level, two-bedroom loft quartershare in the Grand Summit Resort Hotel! This trailside condo can be used, rented, or traded for stays at other vacation destinations! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property for 1 week every 28 days, on a rotating basis. This mountain-side unit features an open-concept kitchen/dining

  Patricia Fitzpatrick Skihome Realty

  311 Qtr 3 Grand Summit Way, Dover, VT 05356

Showing Results 41 - 80, Page 2 of 9