Windham County VT Homes for Sale

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  $20,000

  • Land
  • 1.3 Acres
  • $15,385 per Acre

  0 Smead Rd Unit 5097619, Wardsboro, VT 05360

  Affordable opportunities to own land in Southern Vermont are becoming increasingly hard to find. This 1.30+/- acre wooded parcel on Smead Road offers a gradual rise from the road, creating a private, natural setting to enjoy now or explore for the future. Conveniently located between Mount Snow and Stratton, the property is close to year-round recreation, including skiing, snowmobiling, hiking,

  Jacki Murano Southern Vermont Realty Group

  0 Smead Rd Unit 5097619, Wardsboro, VT 05360
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  /29

  $825,000

  • 4 Beds
  • 3.5 Baths
  • 1,993 Sq Ft

  18 High Point Dr Unit 501, Stratton, VT 05360

  Located just one mile from Stratton’s Base Lodge and Village, this 4-bedroom, 3-bath end-unit Styles Brook townhome offers the perfect combination of convenience, comfort, and year-round mountain living. Spanning three levels, Unit 501 enjoys the added privacy, extra windows, and abundant natural light that come with end-unit ownership. The main level is designed for gathering, featuring

  Cheyanne Pugliese

  18 High Point Dr Unit 501, Stratton, VT 05360
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  /31

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  28 Styles Branch Rd Unit 305, Stratton, VT 05360

  Experience the ease of Stratton Mountain living from this inviting three-bedroom Styles Brook condominium, ideally located just moments from the lifts. Hop on the convenient winter shuttle or enjoy a pleasant walk to the base area, with Stratton's Sports Center, fitness facilities, and year-round amenities just a short stroll away.Designed for both comfort and entertaining, the spacious main

  Carrie Mathews Winhall Real Estate

  28 Styles Branch Rd Unit 305, Stratton, VT 05360
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  /28

  $480,000

  • 5 Beds
  • 2 Baths
  • 2,194 Sq Ft

  3327 Route 30, Jamaica, VT 05343

  Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and

  Carrie Mathews Winhall Real Estate

  3327 Route 30, Jamaica, VT 05343
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  /40

  $1,500,000

  • 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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  /14

  $425,000

  $90K PRICE DROP

  • 3,364 Sq Ft

  28 Brook St, Brattleboro, VT 05301

  Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. The building consists of four spacious 2-bedroom, 1-bath apartments, providing a desirable and consistent unit mix. Pride of ownership is evident throughout, making this a turnkey addition to any portfolio. Beyond the existing income, the property offers exciting upside with attic

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  28 Brook St, Brattleboro, VT 05301
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  /12

  $422,000

  $43K PRICE DROP

  • 3,756 Sq Ft

  820 Western Ave, Brattleboro, VT 05301

  Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. The building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting pride of ownership and minimizing near-term

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  820 Western Ave, Brattleboro, VT 05301
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  /9

  $350,000

  $35K PRICE DROP

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

  1950 N Main St, Londonderry, VT 05148

  PRICE REDUCTION-- to Sell! 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

  Wilkie Bushby TPW Real Estate

  1950 N Main St, Londonderry, VT 05148
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  /27

  $140,000

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft

  2074 Vt Rt 30, Jamaica, VT 05343

  Some places stop time. River's Edge is one of them.Step off the front door and onto a 10×12 covered porch shaded by old hemlocks, facing directly over the West River away from the road, away from everything. The sound of moving water. The smell of the trees after rain. This porch is not an afterthought Brand new Lancaster Log Cabins "Sierra" Park Model. This 100% turn-key real log cabin

  Mike England Michael England Real Estate

  2074 Vt Rt 30, Jamaica, VT 05343
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  $495,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,115 Sq Ft

  367 Stratton Gate Rd, Jamaica, VT 05343

  Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

  

  Alison Cummings

  Cummings & Co

  367 Stratton Gate Rd, Jamaica, VT 05343
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  /43

  $495,000

  $40K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft

  176 Brophy Ln, Londonderry, VT 05148

  Discover this charming Vermont log cabin, situated on a quiet, secluded lot just 5 minutes from downtown Londonderry, and 15 minutes to downtown Manchester's restaurants and shopping. This home offers the perfect balance of peaceful mountain living and easy access to local amenities.The first level welcomes you into a large, open-concept living room, dining room, and kitchen area, perfect

  

  Christopher Cummings

  Cummings & Co

  176 Brophy Ln, Londonderry, VT 05148
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  /54

  $1,249,000

  • 3 Beds
  • 3 Baths
  • 3,654 Sq Ft

  201 Chester Rd, Grafton, VT 05146

  Meticulously maintained and thoughtfully designed, this three-bedroom, three-bath home offers the perfect balance of comfort, functionality, and classic Vermont charm. Set on a picturesque parcel with stunning long-range views, the property is surrounded by mature trees, a small pond, established gardens, and simple, easy-to-maintain landscaping that enhances the natural beauty of the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  201 Chester Rd, Grafton, VT 05146
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  /17

  $365,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  120 Green Mountain Trail, Londonderry, VT 05148

  Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and family room Recent improvements include a brand-new roof (2026) and the added peace of mind of a fully operational

  Wilkie Bushby TPW Real Estate

  120 Green Mountain Trail, Londonderry, VT 05148
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  /33

  $339,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  8 Beech Tree Ln, Newfane, VT 05345

  This is just the cutest little cottage you ever did see! It is just the right size not too big, not too small. This charming country cottage would be a wonderful small footprint primary home or would make an ideal weekend getaway! The first floor living space is open with lovely wood floors and a wood stove perfect for those crisp country evenings, tastefully updated kitchen, dining area, and

  Rebecca Seymour Brattleboro Area Realty

  8 Beech Tree Ln, Newfane, VT 05345
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  /60

  $3,995,000

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

  816 Black Bear Rd, Jamaica, VT 05343

  Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an 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

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  816 Black Bear Rd, Jamaica, VT 05343
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  $995,000

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  136 Yeaw Rd, Dover, VT 05341

  A property that truly must be seen to be appreciated, this exceptional Southern Vermont home offers the perfect balance of privacy and convenience, just minutes from Mount Snow and the village of West Dover. Filled with natural light and hardwood floors, the home offers spaces designed for both comfortable everyday living and entertaining. The beautifully renovated primary suite features a

  Amy Carson Lowe's Real Estate, LLC

  136 Yeaw Rd, Dover, VT 05341
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  /11

  $585,000

  • Land
  • 36.69 Acres
  • $15,944 per Acre

  0 Pine Banks Rd Unit 5096685, Westminster, VT 05158

  Exceptional opportunity to own 36.69 acres of scenic Vermont countryside on desirable Pine Banks Road on the Westminster/Putney border. This beautiful parcel offers a rare combination of expansive open meadows, wooded privacy, and breathtaking long-range views across the Connecticut River Valley and surrounding Green Mountain foothills. The property's rolling landscape provides multiple potential

  Mickey Hipp BHG Masiello Brattleboro

  0 Pine Banks Rd Unit 5096685, Westminster, VT 05158
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  /26

  $1,100,000

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  48A Hammer Beam Loop Unit 48A, Dover, VT 05356

  Stunning post-and-beam townhome at the base of Mount Snow ski resort. Built in 2007 and completely renovated for turnkey enjoyment, this exceptional unit offers a style and scale rarely found this close to the mountain. Rustic natural woodwork runs throughout, a product of the exposed post-and-beam construction that gives the home its unmistakable character. The open-concept main living level

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48A Hammer Beam Loop Unit 48A, Dover, VT 05356
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  /34

  $460,000

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

  216 Ghastly Job Way, Wilmington, VT 05363

  Escape to the beauty of Vermont in this private mountain retreat, ideally situated at the end of a quiet country road. Set on a secluded parcel, this charming getaway boasts sweeping long-range views stretching across the Green Mountains and National Forest to Mount Snow, with easterly vistas toward neighboring Marlboro. Take in spectacular sunsets from the covered front porch or unwind

  Monique White Deerfield Valley Real Estate

  216 Ghastly Job Way, Wilmington, VT 05363
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  /48

  $1,100,000

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

  35 Theron Fisher Rd, Grafton, VT 05146

  Nestled along the Saxtons River, moments from historic Grafton, this beautifully restored Colonial farmhouse offers a rare blend of Vermont history, modern luxury, and exceptional curb appeal. Originally built circa 1820, the home has been meticulously reimagined and rebuilt with extraordinary attention to quality and architectural integrity. The renovation includes new plumbing, electrical,

  Gary Coger Four Seasons Sotheby's Int'l Realty

  35 Theron Fisher Rd, Grafton, VT 05146
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  /26

  $219,000

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,136 Sq Ft

  279 North St, East Dover, VT 05341

  Rustic Hunting Cabin on 1+/- Acres. Spring water supply and a holding tank for septic in place. Several sleeping areas including a loft. One full bathroom. Kitchen with stove, ,microwave, refrigerator, stove, pellet stove, wood stove, 2 mini splits, washer & dryer. Plan your weekend runaway now!

  Janet Boyd Boyd Real Estate

  279 North St, East Dover, VT 05341
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  $929,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,831 Sq Ft

  60 Whites Hill Rd, Dover, VT 05356

  Most people remember the porch first. A 330 sq ft screened sanctuary, floor-to-ceiling panel screens, no handrails, no visual interruption, spring-fed pond with new dock, 20-acre hay field, and the Green Mountain ridgeline beyond. This property must be experienced in person. No photo does it justice.1,831 square feet is simply where this property starts. Not included in that number: a fully

  Monica Sumner BHG Masiello Brattleboro

  60 Whites Hill Rd, Dover, VT 05356
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  /36

  $529,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,936 Sq Ft

  202 Twin Brook Cir, Londonderry, VT 05148

  Tucked away at the end of a long private driveway on a quiet cul-de-sac, this impeccable 4-bedroom chalet offers the perfect blend of privacy, adventure, and year-round Vermont living in the sought-after Powder Mill community. Set on 1.54 wooded acres, the property is surrounded by nature with access to maintained hiking and snowmobile trails, including connections to the VAST trail network and

  Carrie Mathews Winhall Real Estate

  202 Twin Brook Cir, Londonderry, VT 05148
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  /31

  $425,000

  $25K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,952 Sq Ft

  53 Sugar House Rd, West Dover, VT 05356

  Just minutes from Mount Snow, this contemporary chalet offers approximately 3,000 square feet of finished living space and easy access to Southern Vermont's year-round recreation.A cathedral ceiling, floor-to-ceiling windows, abundant natural light, hardwood floors, and a wood-burning fireplace create a warm and inviting atmosphere. The flexible floor plan offers ample space for

  Melissa Nebelski Real Broker LLC

  53 Sugar House Rd, West Dover, VT 05356
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  /35

  $549,000

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  7 Lightning Ledge Way, Wilmington, VT 05363

  Located in the Chimney Hill community, this four-bedroom, two-bath home offers the perfect Southern Vermont retreat for every season. The open-concept living, kitchen, and dining area creates a welcoming space for gathering with family and friends after a day of skiing, boating, hiking, or exploring the area. Warm wood accents and comfortable living spaces create a relaxed Vermont atmosphere that

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  7 Lightning Ledge Way, Wilmington, VT 05363
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  /50

  $1,200,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft

  364 Houghtonville Rd, Grafton, VT 05146

  At the beginning of a dirt road just outside the historic village of Grafton VT you will find an exceptional country estate that combines timeless New England charm with modern comfort, privacy, and equestrian amenities. Thoughtfully designed to replicate a classic colonial home and extensively updated by its current owners, this meticulously maintained property offers an extraordinary lifestyle

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  364 Houghtonville Rd, Grafton, VT 05146
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  $399,000

  $60K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  60 E Brook Crossing, Wilmington, VT 05363

  Tucked among mature trees in the desirable lower section of Chimney Hill, this charming home offers comfort, character, and easy living. A gently sloping gravel driveway and attached converted garage provide year-round convenience, while beautifully established perennial gardens and a gently sloping yard create an inviting outdoor setting rarely found in the area. Inside, the home exudes warmth

  Erica Reynolds Southern Vermont Realty Group

  60 E Brook Crossing, Wilmington, VT 05363
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  $915,000

  $34K PRICE DROP

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

  56 Shattarack Rd Unit D6, Stratton, VT 05360

  Experience ultimate year-round luxury in this tastefully renovated townhome at Slopeside, featuring convenient trail access. Perfectly blending comfort and convenience, this inviting mountain retreat features an updated kitchen and baths, a cozy wood-burning fireplace, and mini-splits for efficient summer cooling. The spacious layout offers three bedrooms plus a private loft complete with its own

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  56 Shattarack Rd Unit D6, Stratton, VT 05360
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  /33

  $339,000

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

  57 Timber Ln, Wardsboro, VT 05360

  Conveniently located between Mount Snow and Stratton Resort you'll find this three-bedroom, two-bathroom home surrounded by lush perennial gardens that thrive in the sun of the one-acre lot's southern exposure within the desirable Snow Mountain Farms community of Wardsboro, Vermont. The main level features an inviting open-concept layout that seamlessly connects the galley kitchen with eat-in

  Kim Meeker Southern Vermont Realty Group

  57 Timber Ln, Wardsboro, VT 05360
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  /46

  $485,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  4027 Route 100 Hwy, Wardsboro, VT 05360

  Welcome to Your Vermont Retreat on scenic Route 100 in Wardsboro. Beautifully maintained and thoughtfully designed, this turnkey 3-bedroom, 2-bath home is ready to enjoy from day one whether as your full time residence, vacation getaway, or a highly successful short-term rental that guests absolutely love. Walking in through the covered entry you’ll find soaring cathedral ceilings in the living

  Steve Goldfarb Deerfield Valley Real Estate

  4027 Route 100 Hwy, Wardsboro, VT 05360
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  $4,500,000

  • 5 Beds
  • 5.5 Baths
  • 5,700 Sq Ft

  24 Sawmill Rd, Stratton, VT 05360

  Experience the ultimate Stratton Mountain lifestyle from this exceptional ski home, perfectly positioned in one of the resort's most coveted locations. Offering the rare advantage of deeded access to Stratton's impeccably groomed ski trail, this extraordinary property places world-class skiing just steps from your front door—an amenity few homes can claim and even fewer can match.Designed for

  Carrie Mathews Winhall Real Estate

  24 Sawmill Rd, Stratton, VT 05360
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  /44

  $1,475,000

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft

  691 Black Bear Rd, Jamaica, VT 05343

  A long winding driveway through a mountain of foliage leads you to this extraordinary mountain-modern retreat, perched high above nearly 200 acres of protected Vermont wilderness. Thoughtfully crafted by Big Pine Builders LLC, this striking off-grid solar home seamlessly blends contemporary design with Vermont’s rugged natural beauty, allowing you to live on the sun’s rhythm while enjoying

  Carrie Mathews Winhall Real Estate

  691 Black Bear Rd, Jamaica, VT 05343
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  /43

  $1,392,000

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

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations.Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where a brick fireplace

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148
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  /18

  $535,000

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  12 Ober Tal Dr Unit C14, Stratton, VT 05360

  Opportunity awaits in this trailside condominium at Stratton Mountain Resort. Ideally positioned for convenient access to the Tamarack Chairlift and Stratton Village, this residence offers the mountain lifestyle buyers seek with direct access to skiing, dining, shopping, and year-round resort amenities. Inside, a wood-burning fireplace anchors the living area, creating an inviting space to gather

  Timothy Mich Doddridge Stratton Real Estate

  12 Ober Tal Dr Unit C14, Stratton, VT 05360
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  /23

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 Mill Rd, West Dover, VT 05356

  When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 3 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large vaulted living room and wood burning fireplace on brick hearth,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  7 Mill Rd, West Dover, VT 05356
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  $2,100,000

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

  121 Fannie Hill Rd, Wilmington, VT 05363

  Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  121 Fannie Hill Rd, Wilmington, VT 05363
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  /30

  $649,000

  • 5 Beds
  • 3 Baths
  • 2,830 Sq Ft

  36 Bears Den Rd, West Dover, VT 05356

  Lovely ski home home in an ideal location, offering the privacy of a single-family residence with the convenience of a groomed ski-home trail and direct shuttle service just steps from your front door.Nestled on a well-positioned lot in the desirable Bears Crossing community, the home backs directly to the ski-home trail with a bridge to cross right to your deck on your way home and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  36 Bears Den Rd, West Dover, VT 05356
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  /42

  $959,900

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

  598 Hubbard Hill Rd, Halifax, VT 05342

  Set on 65± acres, this four-bedroom, three-bath home offers the privacy, views, and outdoor lifestyle that so many buyers seek in Southern Vermont. Perched to capture sweeping mountain views and spectacular sunsets, the home welcomes you with a covered front porch where you can relax and take in the ever-changing landscape.Inside, the spacious floor plan is designed for comfortable year-round

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  598 Hubbard Hill Rd, Halifax, VT 05342
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  /31

  $1,050,000

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

  1C Ego Aly, Dover, VT 05356

  Breathtaking, direct Mount Snow views from this spectacular Outlook Townhome, perched just above the base area at Mount Snow Ski Resort. With rustic natural wood finishes, soaring vaulted spaces, and sweeping slopeside exposure, this five-bedroom, four-bath townhome strikes a rare balance of warmth and luxury. A timber-framed covered porch wraps around to the rear, opening up to west and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1C Ego Aly, Dover, VT 05356
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  /60

  $3,100,000

  $395K PRICE DROP

  • 9 Beds
  • 11 Baths
  • 6,726 Sq Ft

  238 Stowe Hill Rd, Wilmington, VT 05363

  Green Meadows Farm is a rare Southern Vermont estate where timeless character, modern comfort, and exceptional recreational amenities come together across more than 16 picturesque acres. Just minutes from Lake Raponda, downtown Wilmington, Mount Snow, and The Hermitage Club, this remarkable property offers sweeping mountain views, stunning sunsets, and the space to create lasting memories for

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  238 Stowe Hill Rd, Wilmington, VT 05363

Showing Results 161 - 200, Page 5 of 12