Windham County VT Homes for Sale

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  /60

  $1,350,000

  • 5 Beds
  • 3.5 Baths
  • 3,516 Sq Ft

  732 Under the Mountain Rd, South Londonderry, VT 05155

  Welcome to "Fairmount," a beautiful historic home with unrivaled panoramic views and an extraordinary blend of history, grace, and quintessential Vermont living on 42 acres. Originally built in 1810 and artfully reimagined in 1987, the 5BR farmhouse seamlessly merges historic charm with modern sensibility. Exposed beams, wide plank floors, and architectural character remain, while the thoughtful

  Claudia Harris Mary Mitchell Miller Real Estate

  732 Under the Mountain Rd, South Londonderry, VT 05155
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  /12

  $119,000

  • Land
  • 5 Acres
  • $23,800 per Acre

  0 Banning Rd, Putney, VT 05346

  Location is key, and locations like this don't come along often. Almost at the top of Putney Mountain is this 5+/- acres of mature hard and soft woods, including red oak, birch, beech, pine and hemlock, just waiting to host your full or part time dwelling. The existing driveway, which is shared with the seller, offers access to the length of the parcel. There's a State Wastewater Permit with a

  Bill Hickok Berkley & Veller Greenwood Country

  0 Banning Rd, Putney, VT 05346
• 

  

  

  /41

  $725,000

  • 3 Beds
  • 3.5 Baths
  • 4,219 Sq Ft

  5 N Main St, Wilmington, VT 05363

  Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool

  Morriah Adams BHG Masiello Brattleboro

  5 N Main St, Wilmington, VT 05363
• 

  

  

  /17

  $150,000

  • Land
  • 2.8 Acres
  • $53,571 per Acre

  37 Fred Houghton Rd, Putney, VT 05346

  Just in time! So special! This unusual offering was a beloved family complex for many years. The land is a delight of mixed hardwoods and evergreens, easy to walk and gently rolling for intrigue. Walk to "downtown" Putney for the small town energy, pop in the auto for a short drive to everything else...interstate access, NH, skiing...hospitals and services.....or tuck in at home for a

  Christine Lewis Brattleboro Area Realty

  37 Fred Houghton Rd, Putney, VT 05346
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  /22

  $539,000

  • Land
  • 2.88 Acres
  • $187,153 per Acre

  309 Vermont Route 100, Dover, VT 05356

  Prime Investment Opportunity – Near Mount Snow Ski Resort!An exceptional development opportunity awaits just half a mile from Mount Snow Ski Resort. This level lot with stunning mountain views is ideally situated close to all area recreation – skiing, snowboarding, hiking, biking, and more.Plans for 8 units / 24 bedroomsTown sewer availableMost permits secured – only waiting on

  Rich Caplan Deerfield Valley Real Estate

  309 Vermont Route 100, Dover, VT 05356
• 

  

  /13

  $79,000

  • Land
  • 3.69 Acres
  • $21,409 per Acre

  0 Honeycomb Hill, Marlboro, VT 05301

  On the privately maintained road of Honeycomb Hill sits this 3.69 acre lot. The wooded parcel has young tree growth and slopes gently. There are three areas that are fairly level and open and may be suitable building sites. Just 30 minutes to Mt. Snow, 25 minutes to Brattleboro and 15 minutes to Harriman Reservoir, this conveniently located parcel offers easy access to all of Southern Vermont's

  Laura D'Angelo Berkley & Veller Greenwood Country

  0 Honeycomb Hill, Marlboro, VT 05301
• 

  

  /19

  $194,000

  • Land
  • 20.09 Acres
  • $9,657 per Acre

  189 North St, Dover, VT 05356

  Discover the perfect Vermont retreat on this 20.09 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  189 North St, Dover, VT 05356
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  /10

  $88,000

  • Land
  • 10.05 Acres
  • $8,756 per Acre

  Lot 3 North St, Dover, VT 05431

  Discover the perfect Vermont retreat on this 10.15 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 3 North St, Dover, VT 05431
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  /38

  $520,000

  • 3 Beds
  • 3 Baths
  • 2,040 Sq Ft

  829 Pennel Hill Rd, Halifax, VT 05342

  Spacious cabin set on 16.4 acres with stream and pond. Open main living area features hardwood floors, vaulted ceilings with skylights, exposed beams, and an efficient wood stove. Updated kitchen includes stainless steel appliances and breakfast bar seating.Main level bedroom with shared en suite bathroom featuring claw foot tub and walk-in shower. Spiral staircase leads to primary suite with

  Megan Quinn Southern Vermont Realty Group

  829 Pennel Hill Rd, Halifax, VT 05342
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  /9

  $118,000

  • Land
  • 10.04 Acres
  • $11,753 per Acre

  Lot 2 North St, Dover, VT 05431

  Discover the perfect Vermont retreat on this 10.48 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 2 North St, Dover, VT 05431
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  /9

  $430,000

  • 7 Beds
  • 4 Baths
  • 3,551 Sq Ft

  1950 N Main St, Londonderry, VT 05148

  It is possible to live rent- or mortgage-free — and here’s your opportunity.This fully rented, three-unit multi-family property is already generating income. Live in one unit and let the other two cover your expenses, or bring your own vision to life in this premier location. Zoned for both commercial and residential use, the possibilities are extensive. Imagine a riverfront restaurant with

  Wilkie Bushby TPW Real Estate

  1950 N Main St, Londonderry, VT 05148
• 

  

  /23

  $1,150,000

  • 6,442 Sq Ft

  69-71 Elliot St, Brattleboro, VT 05301

  Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

  Erica Reynolds Southern Vermont Realty Group

  69-71 Elliot St, Brattleboro, VT 05301
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  /20

  $479,000

  • 5 Beds
  • 4 Baths
  • 3,064 Sq Ft

  176 High St, Brattleboro, VT 05301

  Unique opportunity to live very comfortably in the more than 1400 sq ft 1st floor apartment with private laundry, private covered porch and your own deck. The apartment has 2 plus bedrooms and 2 full bathrooms, eat in kitchen, dining room and living room. invest in your own home and have revenue from 2 apartments to help with costs. Apartment #2, on the 2nd floor, is a 1-2 bedroom unit which has

  Susan Bellville Bellville Realty

  176 High St, Brattleboro, VT 05301
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  /11

  $75,000

  • Land
  • 1.8 Acres
  • $41,667 per Acre

  L40 Boardman Loop, Wardsboro, VT 05360

  Nestled in the desirable Snow Mountain Farms West community, this 1.8-acre wooded lot offers the perfect setting to build your Vermont dream home or getaway. Gently sloping and bordered by the serene Wardsboro Brook (outside the FEMA flood zone), the property combines natural beauty with practical readiness. A state-issued wastewater permit for a 3 bedroom single family home and an individual

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  L40 Boardman Loop, Wardsboro, VT 05360
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  /28

  $195,000

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft

  274/76Qtr.1-4 Grand Summit Way, Dover, VT 05356

  FULL ownership of this sleep 10 condo comprises of two units. Unit 276 has a private bedroom with a queen bed, queen sleeper sofa and queen murphy bed in the living area. Kitchenet and a full bath with an extra large covered balcony. Adjoining room 274 has 2 king beds and a full bath. Units are located on the base area side of the hotel. Wake up to the Grand Summit Express and the Bluebird lifts

  Kelly Agrillo Southern Vermont Realty Group

  274/76Qtr.1-4 Grand Summit Way, Dover, VT 05356
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  /29

  $199,000

  • 2 Beds
  • 1 Bath
  • 844 Sq Ft

  8577 Vermont 30 Unit H, Jamaica, VT 05343

  Welcome to The Willows. Where convenience, comfort, and value come together in this well-appointed Condo featuring 2 bedrooms, 1 full bathroom with washer and dryer and updated appliances. Set privately back from Route 30, this thoughtfully maintained unit offers peaceful surroundings just two minutes from Stratton Access Road and within easy reach of Jamaica State Park and the West River. Ideal

  Tara van de Velde Four Seasons Sotheby's Int'l Realty

  8577 Vermont 30 Unit H, Jamaica, VT 05343
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  /7

  $499,000

  • Land
  • 2 Acres
  • $249,500 per Acre

  70 Overlook Dr, Dover, VT 05356

  Stunning 2 acre building parcel at the prestigious Peaks at Mt Snow directly across from the ski resort. This lot affords tremendous privacy and exposure, but with amazing access and amenities including direct on call shuttle service from your door to the mountain, indoor pool, gym, clubhouse, and game courts. Paved road access, sewer, and water, means total peace of mind. Build your dream home

  Adam Palmiter Berkley & Veller Greenwood/Dover

  70 Overlook Dr, Dover, VT 05356
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  /14

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360

  The absolute best location in one of Stratton's most desirable communities!This four bedroom, three and one half bath townhome is located directly on the ski trail. Immaculate interior. Bright sunny interior with eastern and southern exposure. One car garage, family room, back patio with new hot tub. Private pool and hot tubs located a short walk away. Shuttle service to Stratton base area

  John Sikes Stratton Real Estate

  63 Sunbowl Ridge Rd Unit 63A, Stratton, VT 05360
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  /27

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft

  16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356

  Rare Rare Rare! There are only 2 townhomes of this style at the desirable Snowtree development, and this particular 3 bedroom, 3 bath has been completely renovated. Walk out your private entry to the base area at Mount Snow via the convenient stream crossing bridge to access the magic carpet and tubing area, ideal for the ski season, but also any summer festivals. If someone doesn't ski they can

  Adam Palmiter Berkley & Veller Greenwood/Dover

  16A Snow Tree Ln Unit Cedars 1, Dover, VT 05356
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  /12

  $675,000

  • Land
  • 45 Acres
  • $15,000 per Acre

  000 Under the Mountain Rd, South Londonderry, VT 05155

  Travel down a quiet, tree-lined country road past historic homes, horse farms, and a large nature preserve to discover this magnificent property with views of Stratton and Bromley mountains in the distance. A large open field graced with wild flowers, apple trees and classic Vermont rock walls provides an ideal level home site, protected on three sides by extensive mature woods. The parcel has

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  000 Under the Mountain Rd, South Londonderry, VT 05155
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  /13

  $249,000

  • Land
  • 0.71 Acre
  • $350,704 per Acre

  24 Lower Highlands Rd, Dover, VT 05356

  Exceptional development opportunity just two minutes from the Mount Snow base area. This 0.71-acre parcel is fully approved for a four-unit residence with occupancy for 16. State wastewater and town construction permits are secured, and full architectural and structural engineering plans will convey.All approvals are valid for the next two years, allowing for immediate construction. With

  Jacki Murano Southern Vermont Realty Group

  24 Lower Highlands Rd, Dover, VT 05356
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  /12

  $995,000

  • 3 Beds
  • 3 Baths
  • 1,501 Sq Ft

  759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

  Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium at Hearthstone Lodge offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

  John Sikes Stratton Real Estate

  759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
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  /59

  $495,000

  • 3 Beds
  • 2 Baths
  • 3,090 Sq Ft

  301 Maple St, Brattleboro, VT 05301

  Sweet! It is starting to get chilly, we remember the oversized salt water pool fun and the summer heat on tanned skin, coming again in the spring. The flowers and shrubs will sing again next season, but for now, we get to love the hardscape that comes to life catching flakes and creating breathtaking sculptures that glitter and change as we watch. It is the season for snuggling in, all toasty and

  Christine Lewis Brattleboro Area Realty

  301 Maple St, Brattleboro, VT 05301
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  /40

  $125,000

  • Land
  • 1.58 Acres
  • $79,114 per Acre

  408 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sacon Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

  Sigrid Pickering Chimney Hill Realty

  408 Fox Mountain Rd, Wilmington, VT 05363
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  /35

  $125,000

  • Land
  • 1.52 Acres
  • $82,237 per Acre

  406 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

  Sigrid Pickering Chimney Hill Realty

  406 Fox Mountain Rd, Wilmington, VT 05363
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  /33

  $85,000

  • Land
  • 1.04 Acres
  • $81,731 per Acre

  402 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

  Sigrid Pickering Chimney Hill Realty

  402 Fox Mountain Rd, Wilmington, VT 05363
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  /36

  $210,000

  • Land
  • 30.1 Acres
  • $6,977 per Acre

  184 Schoolhouse Rd, Jamaica, VT 05343

  Jamaica, Vermont's hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

  Curtis Trousdale

  184 Schoolhouse Rd, Jamaica, VT 05343
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  /15

  $69,000

  • Land
  • 3.58 Acres
  • $19,274 per Acre

  Lot 4 Ghastly Job Way, Wilmington, VT 05363

  3.58 acres east of Wilmington village. This property is ready to build on, site work has commenced; tree clearing and partial driveway installed, fully engineered, survey, and Sate of Vermont Wastewater Permit for the construction of a three bedroom home. This parcel offers a great location, close to Lake Raponda for swimming, near Molly Stark State Park for hiking and minutes to Lake Whitingham

  Monique White Deerfield Valley Real Estate

  Lot 4 Ghastly Job Way, Wilmington, VT 05363
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  /47

  $999,000

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

  151 Holland Rd, Dover, VT 05341

  An outdoor enthusiast’s dream retreat! This breathtaking 92.6-acre Vermont sanctuary is a paradise for nature lovers, equestrians, and adventurers alike. The property features rambling stone walls, lush gardens, cherry trees, blueberry bushes, rolling pastures, woodlands, babbling brooks, a serene pond, and miles of scenic trails. The charming, open-concept, four-bedroom Cape includes a

  Patrice Schneider Southern Vermont Realty Group

  151 Holland Rd, Dover, VT 05341
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  /32

  $28,500

  • 1 Bed
  • 1 Bath
  • 671 Sq Ft

  302 Qtr.2, 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Top floor one bedroom sleep 6 Valley side end unit. Kitchen, living room with a queen murphy bed and queen sleeper sofa and a king bed in the private bedroom with one full bath. Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round

  Kelly Agrillo Southern Vermont Realty Group

  302 Qtr.2, 89 Grand Summit Way, Dover, VT 05356
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  /23

  $135,000

  • Land
  • 5.1 Acres
  • $26,471 per Acre

  1192 Haven Hill Rd, South Londonderry, VT 05155

  This 5+ acre building lot is ready for planning and designing your 5 bedroom dream-home, WW-2-3657 on a quiet country road, and Land Use Permit 2W0032-3. Just minutes to Gale Meadows and Stratton Mountain Resort, there are plenty of summer and winter outdoor adventures to embark on from hiking, kayaking, and fishing in the summer to skiing and snowshoeing in the winter. Only 25-minutes from

  Mike England Michael England Real Estate

  1192 Haven Hill Rd, South Londonderry, VT 05155
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  /20

  $995,000

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

  56 Shattarack Rd Unit D6, Stratton, VT 05360

  Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

  Kim Morgan-Wohler Wohler Realty Group

  56 Shattarack Rd Unit D6, Stratton, VT 05360
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  /30

  $1,250,000

  • Land
  • 108 Acres
  • $11,574 per Acre

  585 Pleasant Valley Rd, Jamaica, VT 05343

  108 Acres of Pristine Land For Sale – 2 Miles to Stratton Sun Bowl with Panoramic ViewsA rare opportunity to own ~108 acres of stunning land with sweeping views of Stratton’s Sun Bowl and Mount Snow. Just 2 miles to the Sun Bowl base and 15 minutes to Mount Snow, this Jamaica, VT property (on the Stratton line) offers unmatched privacy, no zoning restrictions, and incredible

  Britt Wohler

  585 Pleasant Valley Rd, Jamaica, VT 05343
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  /35

  $39,000

  • 2 Beds
  • 2 Baths
  • 914 Sq Ft

  311 Qtr.2, 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 with a queen sleeper sofa. The lofted bedroom and private bedroom both have king beds. Full bath with double sink vanity on the first floor and a 3/4 bath on the second floor. Benefits of Grand Summit ownership include the best ski in/out

  Kelly Agrillo Southern Vermont Realty Group

  311 Qtr.2, 89 Grand Summit Way, Dover, VT 05356
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  /32

  $380,000

  • 7 Beds
  • 5 Baths
  • 3,518 Sq Ft

  343 Haystack Rd, Wilmington, VT 05363

  A perfect home for those looking to renovate and add value. A home with an apartment is located near outdoor recreation spots like Mount Snow and Haystack Country Club ~ mountain riding, state park hiking across from driveway and snowmobile right from your yard. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers four bedrooms, four baths;

  Jessica Citera Cummings & Co

  343 Haystack Rd, Wilmington, VT 05363
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  /28

  $499,000

  • 5 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  47 Ives Rd, Wilmington, VT 05363

  Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

  Adam Palmiter Berkley & Veller Greenwood/Dover

  47 Ives Rd, Wilmington, VT 05363
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  /26

  $89,499 New Construction

  • 2 Beds
  • 1 Bath
  • 746 Sq Ft

  204 Shady Pines, Westminster, VT 05158

  Welcome to 204 Shady Pines, Westminster VT 05158, where modern comfort meets affordability in Shady Pines MHP! This brand-new Polo model manufactured home offers 2 bedrooms, 1 bathroom, and 746 sq. ft. (14 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  204 Shady Pines, Westminster, VT 05158
• 

  

  /38

  $38,000

  • 2 Beds
  • 2 Baths
  • 878 Sq Ft

  309 Qtr.3, 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

  Kelly Agrillo Southern Vermont Realty Group

  309 Qtr.3, 89 Grand Summit Way, Dover, VT 05356
• 

  

  /26

  $650,000

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

  10 Grouse Ln Unit 10A, Dover, VT 05356

  Owners open to offers! Stunning Post and Beam style townhome overlooking spectacular views of Mount Snow and Haystack ski trails with the sunsets in the west beyond. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, hiking and biking trails in the summer, as well as easy access to the Mount Snow golf course which is directly through the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  10 Grouse Ln Unit 10A, Dover, VT 05356
• 

  

  /24

  $92,999 New Construction

  • 2 Beds
  • 2 Baths
  • 790 Sq Ft

  201 Shady Pines, Westminster, VT 05158

  Welcome to 201 Shady Pines, Westminster VT 05158, where modern comfort meets affordability in Shady Pines MHP! This brand-new Cortes model manufactured home offers 2 bedrooms, 2 bathrooms, and 790 sq. ft. (14 x 60 ft.) of thoughtfully designed living space.Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  201 Shady Pines, Westminster, VT 05158

Showing Results 281 - 320, Page 8 of 10