Windham County VT Homes for Sale

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  /42

  $1,150,000

  • 4 Beds
  • 1 Bath
  • 1,972 Sq Ft

  2245 Burrington Hill Rd, Whitingham, VT 05361

  Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to

  Michael Purcell Berkley & Veller Greenwood/Dover

  2245 Burrington Hill Rd, Whitingham, VT 05361
• 

  

  

  /19

  $479,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  162 Buttonwood Dr, Brattleboro, VT 05301

  It has all you wanted! Shiny wood floors to celebrate New England building, plenty of windows to capture every inch of light possible, granite tops on a multitude of cabinets, a step in shower but also a tub for long soaks or the little ones who visit....total one floor living, so rare locally, even no stairs to the direct entry garage. A service that plows, shovels and mows.....a playground for

  Christine Lewis Brattleboro Area Realty

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  

  /35

  $725,000

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft

  771 Stratton Mountain Access Rd Unit 472, Stratton, VT 05360

  Hang up your keys for the weekend and enjoy one of Stratton’s most convenient locations. Walk to the slopes and Stratton Village for skiing, dining, shopping, and year-round activities. This quiet, top-floor end unit at Long Trail House is filled with natural light and offers wide mountain views, including the front face of Stratton. The desirable two-bedroom, two-bath layout is an ideal choice

  Cheyanne Pugliese

  771 Stratton Mountain Access Rd Unit 472, Stratton, VT 05360
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  /41

  $339,000

  $11K PRICE DROP

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

  6795 Vt Route 100, Londonderry, VT 05148

  Motivated sellers! 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

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  6795 Vt Route 100, Londonderry, VT 05148
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  /36

  $489,000

  $10K PRICE DROP

  • Land
  • 41 Acres
  • $11,927 per Acre

  706 Vt Route 100, Stratton, VT 05360

  Exceptional New Offering! Rare 41± acres in Stratton with extraordinary 180 +/- long-range mountain views, improvements, base camp, driveway, clearings, trails, wildlife, and a substantial WOW factor. All for approx. $12,000/acre. A short drive in from paved Route 100, before the land rises further in elevation, sits the rustic 1-bed base camp overlooking open field and multiple ski

  Jacki Murano Southern Vermont Realty Group

  706 Vt Route 100, Stratton, VT 05360
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  /2

  $149,000

  $50K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 2,710 Sq Ft

  29 Stable Rd, Wilmington, VT 05363

  The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area, The Golf Course and The Hermitage Club close to the Coldbrook. Built as a post and beam home. Features 1 acre with ample parking. Building will need an extensive rehab. Not safe to go into the structure.

  Mark Yule BHG Masiello Brattleboro

  29 Stable Rd, Wilmington, VT 05363
• 

  

  /21

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,053 Sq Ft

  180 Debbie Higgins Ln, Wardsboro, VT 05355

  OPEN HOUSE SUNDAY SEPT 6 1-3PM.Charming, rustic mountain-theme home in excellent turnkey condition located in the peaceful, convenient Snow Mountain Farms in Wardsboro, offering the best of Vermont living. Surrounded by nature and just minutes from scenic hiking trails, outdoor recreation, and year-round adventure, this 3-bedroom, two-story chalet is the perfect mountain retreat. Features include

  Patrice Schneider Southern Vermont Realty Group

  180 Debbie Higgins Ln, Wardsboro, VT 05355
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  /37

  $600,000

  $130K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,635 Sq Ft

  341 Under the Mountain Rd, Londonderry, VT 05148

  Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

  Andy Reed Four Seasons Sotheby's Int'l Realty

  341 Under the Mountain Rd, Londonderry, VT 05148
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  /16

  $425,000

  • 2 Beds
  • 2.5 Baths
  • 1,257 Sq Ft

  190 Depot St, Jamaica, VT 05343

  Tucked into a quiet, sunny setting just steps from Jamaica State Park and the heart of Jamaica Village, this charming two-bedroom plus loft Cape offers the perfect blend of Vermont character, comfort, and convenience. Filled with natural light and warm wood accents, the home has an inviting feel from the moment you step inside. A spacious mudroom provides a practical entry for every season and

  Carrie Mathews Winhall Real Estate

  190 Depot St, Jamaica, VT 05343
• 

  

  /20

  $449,000

  • 3 Beds
  • 3 Baths
  • 1,726 Sq Ft

  4A Suntec Loop Unit 4A, Dover, VT 05356

  Beautiful woodsy Suntec townhome just down from the base of the Mount Snow ski resort. This spacious 3 bedroom plus loft townhome sits about a mile south of Mount Snow, with the development having direct access to snowmobile trails, and easy access to the nearby village of Wilmington and lakes. The unit has a large open concept floor plan with living room with wood burning fireplace and brick

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4A Suntec Loop Unit 4A, Dover, VT 05356
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  /56

  $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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  /28

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  49 West Rd, Wilmington, VT 05363

  Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  49 West Rd, Wilmington, VT 05363
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  /26

  $895,000

  • 4 Beds
  • 3.5 Baths
  • 3,669 Sq Ft

  350 W Hill Rd, Putney, VT 05346

  "Little Orchard" is nestled in a tranquil, storybook setting in Putney; this expansive country estate blends rustic character with sophisticated modern luxury to offer the best in southern Vermont living. The heart of the home is the breathtaking chef's kitchen, bathed in natural light through striking two-story windows and soaring cathedral ceilings. Fully equipped with top-of-the-line

  Thomas Dahlin Berkley & Veller Greenwood Country

  350 W Hill Rd, Putney, VT 05346
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  /45

  $70,000

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft

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

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Grand Summit ownership offers the best ski-in/out mountain location available. This mountain-side unit is a two-bedroom that sleeps ten people. Large primary bedroom with a king bed and queen sleeper sofa. The second bedroom has two sets of twin bunk beds. The living room area with a gas fireplace also has a queen sleeper

  Kelly Agrillo Southern Vermont Realty Group

  315 Qtr.2 ,89 Grand Summit Way, Dover, VT 05356
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  /42

  $340,000

  $10K PRICE DROP

  • 2,745 Sq Ft

  120 Western Ave, Brattleboro, VT 05301

  Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  120 Western Ave, Brattleboro, VT 05301
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  /27

  $169,900

  • 3 Beds
  • 2 Baths
  • 2,246 Sq Ft

  1102 Route 100, Wardsboro, VT 05355

  A great, affordable starter! Mostly open concept with L/D/FM and kitchen all flowing one to the other with lots of windows for light and air, bringing the outside in. There is also a bedroom and full bath on the first floor for aging in place. Attached is a huge shed for a workshop. The big surprise and great treat is the lot across the street that borders the Wardsboro Brook and could be a

  Christine Lewis Brattleboro Area Realty

  1102 Route 100, Wardsboro, VT 05355
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  /20

  $409,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  13 Mill Rd, West Dover, VT 05356

  Three-bedroom, two-bath home on just under a half-acre in Sugar Mill Village offering a functional layout, views of Mount Snow's trails and summit, and a location that puts the area's year-round recreation close at hand. The main level features an open kitchen with breakfast bar, full dining with slider to deck, and living area centered around a wood-burning fireplace, creating a comfortable

  Jacki Murano Southern Vermont Realty Group

  13 Mill Rd, West Dover, VT 05356
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  /39

  $2,900,000

  • 34,419 Sq Ft

  14 Westminster St, Town of Rockingham, VT 05154

  For developers or investors seeking property with stable income and growth potential, the Warner Center campus presents an excellent opportunity. This surveyed 140-acre property comprises 24 residential rental units and 3 commercial spaces within six extensively renovated brick buildings – over 34,000sf altogether. The buildings are situated in a spacious, sunlit field, conveniently located

  Heidi Bernier Berkley & Veller Greenwood Country

  14 Westminster St, Town of Rockingham, VT 05154
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  /39

  $289,000

  Open Sun 11AM - 1PM

  • 2 Beds
  • 1 Bath
  • 1,104 Sq Ft

  30 Pleasant St, Grafton, VT 05146

  Coming Soon! Showings begin at the Open House on Sunday, September 20, 2026, from 11:00 AM–1:00 PM. Sweet home in a prime Grafton Village location! Quaintly tucked just one block off Main Street, this property offers easy access to all that the village has to offer. Set on a level quarter-acre lot bordering the Grafton garden, the setting is both beautiful and easy to maintain. A detached one-car

  Jessica Landers Barrett and Valley Associates Inc.

  30 Pleasant St, Grafton, VT 05146
• 

  

  /57

  $825,000

  $25K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

  Mike England Michael England Real Estate

  4880 Pikes Falls Rd, Jamaica, VT 05343
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  /23

  $445,000

  $54K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,548 Sq Ft

  28 Lightning Ledge Way, Wilmington, VT 05363

  Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Lightning Ledge Way, Wilmington, VT 05363
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  /33

  $459,000

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  5K Sportscenter Village Way Unit A24, Dover, VT 05356

  This ski season, spoil yourself with this 2 bedroom, 2 bath unit at Seasons, one of the few trailside communities in the valley, putting the best of Mount Snow right at your doorstep! Conveniently located between the Sundance base area of Mount Snow and the Carinthia slopes, just gear up and within a 5 minute walk you'll be on the Sundance Lift. Scoot home for lunch on the ski home trail right to

  Prema Fitzpatrick Real Broker LLC

  5K Sportscenter Village Way Unit A24, Dover, VT 05356
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  /33

  $18,000

  $2K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 589 Sq Ft

  102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356

  Trailside! Use it, Rent it, Trade it! 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 1-of-a-kind, end-unit, slopeside 1-bedroom, 1 full bath unit has sleeping space for 4, and looks out over the Sundance Base Lodge and the Sundance Express, the new 6-person chairlift. Open-concept kitchen/dining room, and a

  Donna Brown Skihome Realty

  102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356
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  /2

  $350,000

  $20K PRICE DROP

  • 3,002 Sq Ft

  10 Birge St, Brattleboro, VT 05301

  Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

  Christine Lewis Brattleboro Area Realty

  10 Birge St, Brattleboro, VT 05301
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  /30

  $599,000

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  48 Upper Highlands, Dover, VT 05356

  Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning fireplace, natural woodwork and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48 Upper Highlands, Dover, VT 05356
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  /52

  $699,000

  • Land
  • 38 Acres
  • $18,395 per Acre

  1100 Houghtonville Rd, Grafton, VT 05146

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  1100 Houghtonville Rd, Grafton, VT 05146
• 

  

  /13

  $149,000

  • Land
  • 15.94 Acres
  • $9,348 per Acre

  40 E Putney Brook Rd, Putney, VT 05346

  15.94 +/- surveyed acres in Putney with an Vt state approved septic permit for a 5 bedroom home. Surrounded by tall pines, there is a building site tucked in from the road which was a former homestead with a mobile home. A driveway is roughed in and the building area is elevated from the wetland/flood zone area. The boundary runs close to the banks of the East Putney Brook, known for its habitat

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  40 E Putney Brook Rd, Putney, VT 05346
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  /9

  $250,000

  $230K PRICE DROP

  • Land
  • 7.8 Acres
  • $32,051 per Acre

  16 Overlook Dr, Dover, VT 05356

  A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 7.8 acres of land with a home site featuring full panoramic mountain and woodland views to the north and east, including mountain views to undeveloped national forest land. This property is the largest and most private lot in The Peaks community, providing a

  Patricia Fitzpatrick Skihome Realty

  16 Overlook Dr, Dover, VT 05356
• 

  

  /11

  $360,000

  $225K PRICE DROP

  • Land
  • 36.69 Acres
  • $9,812 per Acre

  0 Pine Banks Rd Unit 5096685, Westminster, VT 05158

  HUGE PRICE IMPROVEMENT--$200,000 REDUCTION!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

  Mickey Hipp BHG Masiello Brattleboro

  0 Pine Banks Rd Unit 5096685, Westminster, VT 05158
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  /44

  $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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  /24

  $270,000

  $40K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft

  461 South Rd, Brattleboro, VT 05301

  This sweet 2 bedroom, 2 bathroom home has been recently rejuvenated with a new heating system, new flooring, new kitchen cabinets and counter tops, and fresh paint inside and out, and a new septic system! There's been quite a bit done to this lovely home that's a short distance to the Marlboro town office and post office and a few minutes' ride down to Brattleboro. There's good lawn space on the

  Susan Bellville Bellville Realty

  461 South Rd, 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
• 

  

  /40

  $825,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Imagine 216 acres of rolling fields, serene woodlands, and a glowing sugarbush tucked along a quiet country dirt road near the Massachusetts border in Halifax, just a short drive to Brattleboro and Wilmington. Held by the same family for generations, this timeless Southern Vermont property includes a farmhouse, barns, and several outbuildings ,many ready for restoration, reimagining, or

  Melissa Nebelski Real Broker LLC

  6036 Jacksonville Stage Rd, Guilford, VT 05301
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  /55

  $750,000

  $99K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 3,877 Sq Ft

  2435 Stage Rd, Guilford, VT 05301

  Only a fortunate few have the privilege of calling Green River Village home - a quintessential Vermont hamlet distinguished by its historic covered bridge, the 1811 timber crib dam, and the iconic wood-spired church proudly perched on the hillside above. Sited next to the bridge, the Green River Bridge House, originally a blacksmith shop, enjoys 300 feet of frontage along the Green River. Built

  John Mcpherson Berkley & Veller Greenwood Country

  2435 Stage Rd, Guilford, VT 05301
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  /23

  $270,000

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft

  41 Organ St, Brattleboro, VT 05301

  A Home Filled With Possibilities! For the first time in 43 years, this charming and comfortable Organ Street home is ready to welcome its next owner. Offering a spacious, open-concept layout and the possibility of first-floor living, this home is both functional and full of potential. The main level features a generous kitchen that flows naturally into the spacious living and dining area,

  Desiree Stango Berkley & Veller Greenwood Country

  41 Organ St, Brattleboro, VT 05301
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  /18

  $299,000

  • Land
  • 1.06 Acres
  • $282,075 per Acre

  12 Someday Rd, Dover, VT 05356

  Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  12 Someday Rd, Dover, VT 05356
• 

  

  /54

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 3,916 Sq Ft

  30 Fieldstone Way, Londonderry, VT 05155

  Set in the peaceful Vermont countryside of Londonderry, this contemporary home offers the perfect blend of spacious living, natural beauty, and convenient access to some of Southern Vermont’s ski areas. Situated on 1.58 acres between Magic Mountain, Bromley, and Stratton, the property is ideally positioned for year-round recreation and relaxation.Built in 2004, the 4,094-square-foot home

  David Shehadi Josiah Allen Real Estate, Inc.

  30 Fieldstone Way, Londonderry, VT 05155
• 

  

  /46

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,707 Sq Ft

  16 A Snowtree Ln, Dover, VT 05356

  This exceptional townhouse in the sought-after SnowTree development offers a unique opportunity for homeownership in a community with a reliable HOA management company. Spread across three meticulously updated levels, the townhouse welcomes you with a spacious, sun-filled living room featuring a wood-burning fireplace and large windows that offer winter mountain views and allow natural light to

  Sheila Joyce-Albano Skihome Realty

  16 A Snowtree Ln, Dover, VT 05356
• 

  

  /51

  $899,800

  $49K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
• 

  

  /21

  $179,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  40 Brookside Dr Unit 2, 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 2, Brattleboro, VT 05301

Showing Results 81 - 120, Page 3 of 13