Windham County VT Homes for Sale

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  /37

  $595,000

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  171 Green Meadow, Brattleboro, VT 05301

  Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living

  Thomas Dahlin Berkley & Veller Greenwood Country

  171 Green Meadow, Brattleboro, VT 05301
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  /58

  $729,000

  $11K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 2,789 Sq Ft

  49 View Point Rd, Putney, VT 05346

  Nestled on 5.54 acres at the end of a quiet, privately maintained road, 49 View Point Road offers the Vermont setting buyers dream of: mountain views, open lawn, wooded privacy, and a warm, light-filled Contemporary Cape just minutes from Putney Village and I-91. This spacious 5-bedroom, 3.5-bath home features 2,789 finished square feet with natural woodwork, hardwood floors, exposed beams,

  Grayson VanHendrick Flex Realty

  49 View Point Rd, Putney, VT 05346
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  /60

  $1,160,000

  • 5 Beds
  • 4 Baths
  • 3,664 Sq Ft

  82 N Brookwood Rd, Stratton, VT 05360

  Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast,

  Kim Morgan-Wohler Wohler Realty Group

  82 N Brookwood Rd, Stratton, VT 05360
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  /23

  $142,000

  $12K PRICE INCREASE

  • Land
  • 2.19 Acres
  • $64,840 per Acre

  192 Pingree Park Ln, Londonderry, VT 05148

  2.17 acres with 199' of riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont's most sought-after

  

  Alison Cummings

  Cummings & Co

  (802) 471-3006

  192 Pingree Park Ln, Londonderry, VT 05148
• 

  

  

  /23

  $127,000

  • Land
  • 2.07 Acres
  • $61,353 per Acre

  191 Pingree Park Ln, Londonderry, VT 05148

  2.07 acres with 140' riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont's most sought-after mountain

  

  Alison Cummings

  Cummings & Co

  (802) 213-7597

  191 Pingree Park Ln, Londonderry, VT 05148
• 

  

  /51

  $799,000

  • 4 Beds
  • 5 Baths
  • 3,992 Sq Ft

  1035 Vermont 121, Windham, VT 05359

  Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A

  Jamie Wylie Stratton Real Estate

  1035 Vermont 121, Windham, VT 05359
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  /26

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  1F Dover Green Loop Unit F, Dover, VT 05356

  Beautifully maintained 2-bedroom plus loft, 2-bath condo in desirable Dover Green. The first floor features a convenient mudroom for all your gear, a primary suite, an additional guest bedroom, a full bath, and laundry area. Upstairs, you’ll find an inviting open-concept living space with vaulted ceilings, a cozy wood-burning fireplace with brick hearth, a spacious eat-in kitchen, and a versatile

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1F Dover Green Loop Unit F, Dover, VT 05356
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  /17

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  550 S Main St, Brattleboro, VT 05301

  Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways,

  Christine Lewis Brattleboro Area Realty

  550 S Main St, Brattleboro, VT 05301
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  /24

  $535,000

  $15K PRICE DROP

  • 4,116 Sq Ft

  33 Oak St, Brattleboro, VT 05301

  This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the

  Kate Barry EXP Realty

  33 Oak St, Brattleboro, VT 05301
• 

  

  /60

  $560,000

  • 3 Beds
  • 3 Baths
  • 2,397 Sq Ft

  14 High Top Rd Unit B124, Wilmington, VT 05363

  Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are

  Sigrid Pickering Chimney Hill Realty

  14 High Top Rd Unit B124, Wilmington, VT 05363
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  /21

  $999,000

  • 2 Beds
  • 1 Bath
  • 8,141 Sq Ft

  225 Missing Link Rd, Bellows Falls, VT 05101

  CONNECTICUT RIVER HOME WITH 500' RIVER FRONTAGE. THE HOME OFFERS A COMMANDING VIEW. THE 2ND FLOOR 2BR LIVING QUARTERS HAS 2241 SQ. FT. LIVING SPACE WITH ATTACHED PARTIAL FINISHED 1600 SQ. FT. THE OPEN SPACE CONCEPT IS IDEAL FOR ENTERTAINING. THIS PROPERTY WILL ALSO COME WITH 12 BOAT DOCKS W/ LAUNCHING AREA TO USE OR LEASE. THE LOWER LEVEL 4300 SQ. FT. WAS THE SHOWROOM, OFFICE AND WORKSHOP FOR THE

  Don Chabot Town and Country Realty

  225 Missing Link Rd, Bellows Falls, VT 05101
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  /27

  $530,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  1160 Fowler Rd, Whitingham, VT 05361

  Nestled in the scenic beauty of Whitingham, Vermont, this inviting 3-bedroom, 2-bath home offers the perfect blend of comfort, craftsmanship, and year-round enjoyment. Step inside to discover a bright, open living space highlighted by stunning vaulted ceilings that create an airy, welcoming feel.The home features a finished basement complete with a spacious game room—ideal for entertaining,

  Kristen Breeden Southern Vermont Realty Group

  1160 Fowler Rd, Whitingham, VT 05361
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  /45

  $449,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  3669 US Route 5, Westminster, VT 05158

  Tucked away in plain sight, this beautifully maintained three-bedroom, two-bath ranch offers the perfect blend of privacy, comfort, and convenience on a 1.1 acre lot in Westminster, Vermont. Step inside through a welcoming mudroom with ample closet space, leading into a thoughtfully updated kitchen featuring an island sink and new countertops—perfect for both everyday living and entertaining. The

  Julie Lowe Lowe's Real Estate, LLC

  3669 US Route 5, Westminster, VT 05158
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  /49

  $374,900

  • 3 Beds
  • 2 Baths
  • 1,074 Sq Ft

  59 Zeller Camp Rd, Grafton, VT 05146

  In a market this tight, a turnkey three-bedroom chalet retreat with this level of recent reinvestment, this much wooded privacy, and a brookside parcel near historic Grafton village does not come up often, and almost never fully furnished and ready to step into on day one.Inside, a bright open layout flows under vaulted ceilings, anchored by a fireplace hearth, a flowing kitchen-living-dining

  Nick Sicard EXP Realty

  59 Zeller Camp Rd, Grafton, VT 05146
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  /7

  $75,000

  • Land
  • 20.8 Acres
  • $3,606 per Acre

  0 Hunter Brook Rd, Marlboro, VT 05344

  *Please do not go onto the neighbors driveways.* Deep into Marlboro, on a seasonal rd, set up camp and fall asleep to the white noise of the brook. The campsite is flat, right off the road and then the land slopes upward. At the back there is a shared pond site.Hunter Brook Rd is not maintained in the wintertime, from the Marlboro side; you'll need to snowmobile, ski or walk in.

  Victoria Woods Brattleboro Area Realty

  0 Hunter Brook Rd, Marlboro, VT 05344
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  /10

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,139 Sq Ft

  108 Morningside Commons, Brattleboro, VT 05301

  Take a deep breath...enjoy your free time...sit back and wait for the walks to be clear, the lawn mowed and the flowers to bloom...without lifting a finger! Take a dip in the clear waters of the fenced, private pool or have a game of friendly tennis or pickleball! No clean up there either! The best of the best! Top floor, end unit 2nd floor deck for looking down at the world, and windows

  Christine Lewis Brattleboro Area Realty

  108 Morningside Commons, Brattleboro, VT 05301
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  /31

  $259,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  51 Golding Rd, Windham, VT 05359

  Tucked away on a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in a clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the

  

  Alison Cummings

  Cummings & Co

  (802) 802-9554

  51 Golding Rd, Windham, VT 05359
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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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  /56

  $409,500

  $20K PRICE DROP

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

  24 School St, Bellows Falls, VT 05101

  Wonderful Victorian with sunlit rooms and many original features include some curved glass windows and stained glass panes in the turreted living room, a tiled fireplace with ornate brass insert, wood floors, curved staircase and beautful molding. The property has been well cared for and has a charming updated kitchen that is warm and inviting with an island, granite countertops, wood floor and a

  Jackie Atwood Jacklyn Atwood Real Estate

  24 School St, Bellows Falls, VT 05101
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  /60

  $525,000

  • 2 Beds
  • 2.5 Baths
  • 3,074 Sq Ft

  4 Newfane Cir Unit 4B, Dover, VT 05356

  LOCATION LOCATION LOCATION!!! Directly across the street from Mt. Show ski resort with shuttle service to and from the mountain. Avoid parking fees and be chauffeured back and forth. Located in the prestigious Greenspring Community, with year round activities. Ski at Mt. Snow, Vermont's closest mountain to NYC, golf in the summer (located with 6 miles of 2 beautiful golf courses, Mt. Snow Golf

  Jason Saphire www.HomeZu.com

  4 Newfane Cir Unit 4B, Dover, VT 05356
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  /26

  $395,000

  • 3,240 Sq Ft

  458 Williams St, Brattleboro, VT 05301

  458 Williams Street, formerly the WKVT headquarters, presents an opportunity for buyers exploring potential residential or mixed-use conversion in a convenient Brattleboro location. The 3,240 SF building is currently configured for office use across two levels, with more than 10 individual rooms, multiple bathrooms, and an existing kitchenette. This layout may lend itself to reconfiguration

  Neil Goldberg Brattleboro Area Realty

  458 Williams St, Brattleboro, VT 05301
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  /44

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,580 Sq Ft

  1229 Sheldon Hill Rd, Wardsboro, VT 05355

  Nestled among the trees in the sought-after Snow Mountain Farms community, this beautifully maintained four-bedroom home is just 7.6 miles to Mount Snow and 13 miles to Stratton Mountain Resort.The welcoming front porch leads to a spacious wrap around deck, creating an ideal setting for entertaining or simply enjoying the peaceful natural surroundings. The main living area features pine

  Jessica Citera Cummings & Co

  1229 Sheldon Hill Rd, Wardsboro, VT 05355
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  /20

  $50,000

  • 2 Beds
  • 1 Bath
  • 530 Sq Ft

  8 Dorf Auf Radar Rd, Wilmington, VT 05363

  Delightful, affordable! Be right in the heart of ski country with access to hiking, boating, fishing and biking! This tidy 2 bedroom home has a 10x16 storage shed for your gear! Big enough for a weekend of fun but small enough to keep the costs reasonable. This is better than renting, and always available when you are! This is an exciting find! The property can only be a vacation/second home only.

  Christine Lewis Brattleboro Area Realty

  8 Dorf Auf Radar Rd, Wilmington, VT 05363
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  /48

  $394,000

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  9F Brumms Way Unit 9F, Dover, VT 05356

  Beautiful end unit on edge of Bear’s Crossing Condo and Home Community with a stream and the forest as your neighbor. Close to the Ski Home trail. This mixed community is 2 minutes to Mount Snow Ski Resort and to mixed use trails for snowmobiling, xcountry skiing and mountain biking. There is also a shuttle running regularly to the resort and beyond! This unit is “turn key” with 2 bedrooms and a

  Steve Goldfarb Deerfield Valley Real Estate

  9F Brumms Way Unit 9F, Dover, VT 05356
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  /60

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,408 Sq Ft

  75 Westminster Rd, Putney, VT 05346

  This charming historic Colonial just moments from Putney Village, blends timeless character with thoughtful updates. This 4-bedroom, 3-bath home features a spacious, open kitchen highlighted by an antique brick hearth, perfect for gathering and entertaining. The flexible floor plan includes a first-floor bedroom with an ensuite full bath and its own separate entrance, offering excellent potential

  Rebecca Hiam Southern Vermont Realty Group

  75 Westminster Rd, Putney, VT 05346
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  /5

  $400,000

  • Land
  • 5.28 Acres
  • $75,758 per Acre

  0 Pond Rd, Town of Rockingham, VT 05346

  Looking for the dream land of your own, in town but outside of it? Look no further! With 5 acres of gently sloped woods there's plenty of space to site multiple building lots if you so wish, and with it abutting Minard's Pond nature area and just minutes from the village, there's plenty to do. Bring your dreams and plans, this might just be for you! Sale is subject to final survey & subdivision

  Courtney Doubleday EXP Realty

  0 Pond Rd, Town of Rockingham, VT 05346
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  /37

  $950,000

  • Land
  • 20.7 Acres
  • $45,894 per Acre

  0 Crotty Dr, Town of Rockingham, VT 05101

  Investors, developers and builders take notice! This large, gently sloped parcel is one the last & largest undeveloped lots of land that fall within the Bellows Falls Village District. Just minutes from downtown and abutting Minard's Pond nature area, this property sits high on the hill with spectacular views available. With dozens of potential building locations and access to town water and

  Courtney Doubleday EXP Realty

  0 Crotty Dr, Town of Rockingham, VT 05101
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  /28

  $52,000

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

  274/76Qtr. 2 Grand Summit Way, Dover, VT 05356

  Wake up to the Grand Summit Express and the Bluebird lifts right outside your room. Sleep 10 condo comprises two units. Unit 276 has a private bedroom with a queen bed, a queen sleeper sofa, and a queen Murphy bed in the living area, a kitchenette, and a full bath with an extra-large covered balcony. The adjoining room, 274, has 2 king beds and a full bath. Units are located on the base area side

  Kelly Agrillo Southern Vermont Realty Group

  274/76Qtr. 2 Grand Summit Way, Dover, VT 05356
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  /28

  $52,000

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

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

  Wake up to the Grand Summit Express and the Bluebird lifts right outside your room. 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

  Kelly Agrillo Southern Vermont Realty Group

  274/76Qtr. 1 Grand Summit Way, Dover, VT 05356
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  /12

  $125,000

  • Land
  • 2 Acres
  • $62,500 per Acre

  70 Deer Hill Dr, Whitingham, VT 05361

  This beautiful 2-acre parcel offers a gently sloping, mostly level landscape with partial clearing already completed—making it an ideal setting for your future home or getaway. The property is well-prepared for development, featuring a drilled well, available septic plans, and an installed electric pedestal for easy utility access. Conveniently located just 15 miles from Mount Snow, this lot

  Kelly Agrillo Southern Vermont Realty Group

  70 Deer Hill Dr, Whitingham, VT 05361
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  /26

  $529,000

  • 1 Bed
  • 1 Bath
  • 820 Sq Ft

  12 Ober Tal Dr Unit C-22, Stratton, VT 05360

  Experience Stratton Mountain living in this well-appointed 1-bedroom, 1-bath condo in the desirable Ober Tal community. Set just off the ski trail with convenient access nearby, this unit offers the benefits of trailside living with a touch more privacy. Inside, the condo has been thoughtfully updated with warm wood and stone accents that create a classic mountain feel, centered around a cozy

  Trent Stephens Wohler Realty Group

  12 Ober Tal Dr Unit C-22, Stratton, VT 05360
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  /37

  $399,000

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  44 Howes Loop, Wilmington, VT 05363

  Thoughtfully maintained 4-bedroom, 2-bath Chimney Hill chalet offering a warm, inviting feel with natural wood finishes, open-concept design, woodstove and features that capture the essence of Vermont living. The main living areas are bright, comfortable and welcoming, with easy flow to a deck overlooking surrounding mountain ridgelines—an ideal setting for both quiet mornings and relaxed

  Jacki Murano Southern Vermont Realty Group

  44 Howes Loop, Wilmington, VT 05363
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  /40

  $675,000

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  47 Oak Hill Dr, Dummerston, VT 05301

  Tucked away on a private road, this impeccably maintained 3-bedroom, 2-bathroom home sits on a serene 6-acre lot, offering the perfect blend of privacy and comfort. Set well back from the road, the property provides a peaceful retreat surrounded by nature. Inside, you’ll find a bright and inviting open-concept layout designed for both everyday living and entertaining. The spacious living and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  47 Oak Hill Dr, Dummerston, VT 05301
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  /47

  $789,000

  • 4 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  15 Sawmill Village Way, Dover, VT 05356

  OPEN HOUSE SAT 5/23 10AM-NOON If you are looking for a quality-built, well-maintained home with modern updates near Mt. Snow, this Village at Sawmill Farms home checks all the boxes! Located just up the hill from the businesses and services of West Dover, near the Mt. Snow golf course, recreational trails, and 2.5 miles from the ski resort, this home is situated perfectly to enjoy the area's best

  

  Beth Vickers

  Vermont Real Estate Company

  (802) 341-9969

  15 Sawmill Village Way, Dover, VT 05356
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  /49

  $380,000

  • 3 Beds
  • 3 Baths
  • 2,307 Sq Ft

  30 Back St, Newfane, VT 05345

  This 1790 historic cape is waiting to reclaim a splendor and idyllic beauty of decades past. Your efforts for its needed “Place-lift” will be well rewarded. Structurally and mechanically sound, the home is fully modernized ready for its next phase of upgrade, remodeling and energized vision, all to be executed at your own pace over time. The first floor has been reconstructed with an open concept

  Randi Ziter Brattleboro Area Realty

  30 Back St, Newfane, VT 05345
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  /38

  $495,000

  • 4 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  137 Stratton Arlington Rd, West Wardsboro, VT 05360

  Classic Vermont Home with stunning hilltop views, minutes from Mount Snow and Stratton. Set on a peaceful New England hilltop, this traditional-style home offers beautiful local and long-range views. Its highly desirable location is just 6 miles from both Mount Snow and Stratton ski resorts, and 6 miles to Grout Pond, providing VAST snowmobile trail access and summer activities.Filled with

  Donald Koelsch Deerfield Valley Real Estate

  137 Stratton Arlington Rd, West Wardsboro, VT 05360
• 

  

  /3

  $125,000

  • Land
  • 1.77 Acres
  • $70,621 per Acre

  997 Stratton Arlington Rd, Stratton, VT 05360

  STRATTON & MOUNT SNOW - Build your dream ski home on this newly subdivided lot with 103' of road frontage and 1.77 private acres located only 10 minutes from both Stratton Mountain Ski Resort and Mount Snow Ski Resort. All the hard work has been done! Survey, septic design, site plan, state of VT wastewater and well approval, and driveway permit have all been approved and filed with the town.

  Derek Greene Derek Greene

  997 Stratton Arlington Rd, Stratton, VT 05360
• 

  

  /47

  $855,000

  • 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
• 

  /2

  $89,900

  • 4 Beds
  • 2 Baths
  • 1,902 Sq Ft

  206 Smith Rd, Jamaica, VT 05343

  Looking for a project? Featuring a drilled well, existing septic, electric, and driveway, you have a good start for a new build, renovation or a combination of the two. The cabin has been added onto many times, making room for a growing family. The land is mostly level, with some nice plantings and the house sits back a little distance from the neighbors. The well is being shared, electric is run

  Christine Lewis Brattleboro Area Realty

  206 Smith Rd, Jamaica, VT 05343
• 

  

  /30

  $374,000

  $25K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  1511 E Dover Rd, Wardsboro, VT 05355

  Tucked along a scenic stretch of East Dover Road, this charming Wardsboro property captures the essence of Vermont country living with the added bonus of easy access to some of Southern Vermont’s most sought-after destinations. Just a short drive to Mount Snow and Stratton Mountain Resort, this location is ideal for year-round recreation—from skiing and snowboarding in the winter to hiking,

  Mike Masters Four Seasons Sotheby's Int'l Realty

  1511 E Dover Rd, Wardsboro, VT 05355

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