Windham County VT Homes for Sale

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  /24

  $255,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  121 Happy Haven Rd, Wilmington, VT 05363

  This home offers endless potential to become your ideal retreat. Tucked away on 1.3 acres at the end of a quiet dead-end road, it provides privacy while still being conveniently close to downtown Wilmington and year-round recreation—whether you enjoy skiing, golfing, hiking, biking, or boating. The main level features an open-concept layout with a cozy living room with a wood-burning fireplace, a

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  121 Happy Haven Rd, Wilmington, VT 05363
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  /47

  $899,000

  • 2 Beds
  • 4 Baths
  • 4,210 Sq Ft

  13 Kimball Hill, Putney, VT 05346

  Bring Your Business Home. This beautifully restored former 1859 Masons Hall has been carefully transformed into a gracious home. Soaring ceilings, period correct 6ft 6/6 windows and original architectural detail attest to the early Italianate Period and the heyday of the ever-so-quaint village of Putney. The current owner has transformed the 1,880sf first floor into a Pilates studio, kitchen and

  Dan Normandeau Berkley & Veller Greenwood Country

  13 Kimball Hill, Putney, VT 05346
• 

  

  

  /28

  $466,000

  • 6 Beds
  • 3.5 Baths
  • 2,766 Sq Ft

  624 Boyd Hill Rd, Wilmington, VT 05363

  Spacious 6-Bedroom Ski & Lake Home in Vermont – Perfect for All Seasons Escape to the beauty of Vermont in this stunning 6-bedroom, 4-bathroom retreat—perfectly situated for year-round adventure between the slopes and the lake. While you’re gathering with loved ones, this warm and welcoming home offers space, style, and all the comforts you need to relax and reconnect. Inside, enjoy a chef’s

  Jason Saphire www.HomeZu.com

  624 Boyd Hill Rd, Wilmington, VT 05363
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  /55

  $929,000

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

  45D Dover Spring Ln, Dummerston, VT 05356

  Enjoy the perfect blend of comfort, convenience, and scenic beauty in this exceptional townhome located in the highly desirable Greenspring community. The private setting offers a spacious backyard, mountain views and a nearby pond. This home offers the peace and tranquility of country living while remaining just minutes from skiing and outdoor recreation.Boasting an expansive 3,200

  Melissa Ellis Southern Vermont Realty Group

  45D Dover Spring Ln, Dummerston, VT 05356
• 

  

  

  /16

  $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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  /32

  $25,000

  • Land
  • 0.3 Acre
  • $83,333 per Acre

  139 Big Bend Loop, Wilmington, VT 05363

  One of a handful of single lots remaining on the Hill! Septic design needs updating, Power is at the street. The lot is buffered by common land on both sides, and there is a drop off at the back. Access is best at the left end of the property, where a gentle slope takes you to this level plateau. View with clearing and in non-leaf seasons. Build your dream home and enjoy all the amenities

  Sigrid Pickering Chimney Hill Realty

  139 Big Bend Loop, Wilmington, VT 05363
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  /28

  $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

  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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  /20

  $350,000

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  3730 Route 100, Wardsboro, VT 05355

  Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.Sellers have given permission to encourage all offers. Property was originally listed for $450,000 but the sellers have reduced the price to $350,000. The tax

  Ginny Read Read Realty LTD

  3730 Route 100, Wardsboro, VT 05355
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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 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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  /58

  $515,000

  • 4 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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  /30

  $18,000

  • 1 Bath
  • 407 Sq Ft

  217 Qtr. 3,89 Grand Summit Way, Dover, VT 05356

  Slope side ski in/out with ski trail views and full hotel amenities! Gain that mountain resort life style at a truly affordable price. Use it, Rent it, Trade it! With 13 weeks of vacation a year round, benefits of Grand Summit ownership including the best ski in/out mountain location available-this is an opportunity to seriously upgrade your vacations. Use of the Grand Summit amenities all year

  Jacki Murano Southern Vermont Realty Group

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

  

  /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
• 

  

  /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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  /19

  $769,000

  • 4 Beds
  • 4 Baths
  • 1,575 Sq Ft

  4L Trailside Village Way Unit H34, Dover, VT 05356

  Welcome to H34 Trailside Village Way, a rare opportunity to own a stunning 4-bedroom, 4-bath slopeside condo in the coveted Seasons on Mount Snow community. This impeccably maintained, never-rented home offers true ski-in/ski-out access—step out your door and onto the trail for unbeatable convenience all winter long.Inside, the open-concept living space is bathed in natural light,

  Jessica Bentz Four Seasons Sotheby's Int'l Realty

  4L Trailside Village Way Unit H34, Dover, VT 05356
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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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  /12

  $50,000

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

  355 Bemis Hill Rd, Putney, VT 05346

  Sweet 3.6 acre lot ready for your imagination! Envision building your dream home bordered by picturesque stone walls and the soothing melody of a babbling brook. The land gently slopes up from the road to a level building site accessed from a rough driveway, you'll need to clear fallen trees, that has remnants of an old cabin. This is a lovely, quiet spot just half a mile off paved Westminster

  Rebecca Seymour Brattleboro Area Realty

  355 Bemis Hill Rd, Putney, VT 05346
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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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

  $450,000

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

  343 Haystack Rd, Wilmington, VT 05363

  This spacious home is located near Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers Four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone

  Jessica Citera Cummings & Co

  343 Haystack Rd, Wilmington, VT 05363
• 

  

  /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
• 

  

  /48

  $799,000

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

  42 Airport Rd, Shaftsbury, VT 05262

  Welcome to this exquisite post and beam timber frame home, nestled in a prime location just moments from the Mount Snow Ski Resort and Mount Snow Golf Course. This remarkable 4-bedroom, 4-bathroom home blends rustic charm with modern luxury, offering an unparalleled mountain retreat perfect for both relaxation and adventure. As you step inside, you’ll be greeted by soaring ceilings and

  Mike Masters Four Seasons Sotheby's Int'l Realty

  42 Airport Rd, Shaftsbury, VT 05262
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  /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
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  /26

  $699,000

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

  10 Grouse Ln Unit 10A, Dover, VT 05356

  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 adjacent woods, and nearby

  Adam Palmiter Berkley & Veller Greenwood/Dover

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

  

  /46

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,960 Sq Ft

  16 Springhill Rd, Dover, VT 05356

  Experience modern luxury in this stunning contemporary home, less than 10 minutes from Mount Snow and just 15 minutes from The Hermitage Club. This thoughtfully designed retreat offers both sophistication and comfort, with high-end finishes and exceptional craftsmanship throughout. You will be captivated by the soaring freestanding stone fireplace, which serves as the heart of the home, complete

  Patrice Schneider Southern Vermont Realty Group

  16 Springhill Rd, Dover, VT 05356
• 

  

  /51

  $879,900

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  7 Yodeling Ln, West Dover, VT 05356

  Charming Log Home with Modern Comfort and Prime Location. This warm and inviting log home offers the perfect blend of rustic charm and modern style. Nestled on a level lot with ample parking, it features a large covered front porch and a spacious rear deck, ideal for enjoying the beautiful outdoors. Step inside to the main level, where you'll find a welcoming living room anchored by a stunning

  Rich Caplan Deerfield Valley Real Estate

  7 Yodeling Ln, West Dover, VT 05356
• 

  

  /60

  $4,495,500

  • 4 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  816 Black Bear Rd, Jamaica, VT 05343

  Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mount Snow ski resorts, it is the ultimate

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  816 Black Bear Rd, Jamaica, VT 05343
• 

  

  /5

  $35,000

  • Land
  • 1.2 Acres
  • $29,167 per Acre

  44 Antler Loop, Dover, VT 05356

  Come and join the nice quiet community of Dover Manor. This lot has road frontage on two sides of the property. There is a small wetland area on the Antler Loop side of the property, about 1/4 of the property. Private roads and close to elementary school, skiing and shopping. Elevation is at about 2000'.Town sewer is available.

  Regina Perrotto Skihome Realty

  44 Antler Loop, Dover, VT 05356
• 

  

  /13

  $50,000

  • Land
  • 2 Acres
  • $25,000 per Acre

  667 Hinkley Brook Rd, Grafton, VT 05146

  Nestled along the picturesque Hinkley Brook Road, this 2-acre parcel offers a rare opportunity to build your dream retreat in the charming and historic town of Grafton, Vermont. Just a short walk from the village center, you’ll enjoy the perfect blend of privacy and convenience, surrounded by the beauty of nature and classic New England charm. This peaceful lot boasts a gently wooded landscape

  Jamie Watson BHG Masiello Keene

  667 Hinkley Brook Rd, Grafton, VT 05146

Showing Results 321 - 360, Page 9 of 11