Windham County VT Homes for Sale

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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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  /2

  $80,000

  $10K PRICE DROP

  • Land
  • 1.97 Acres
  • $40,609 per Acre

  24 Summit Cir, West Brattleboro, VT 05301

  Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

  Claire Renaud Berkley & Veller Greenwood Country

  24 Summit Cir, West Brattleboro, VT 05301
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  /43

  $299,000

  • 3,942 Sq Ft

  2072 N Main St, Londonderry, VT 05148

  This is your chance to own in downtown Londonderry! You have the option of commercial, residential or BOTH. One unit is currently set up for residential use with living area and 3/4 bath on the first level and three bedrooms and full bath on the second floor. The second unit has been used for commercial use in the past with open space and 1/2 bath on the first floor with 3 rooms and 2 full baths

  Catherine Cairns Maple Leaf Real Estate

  2072 N Main St, Londonderry, VT 05148
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  /39

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 1,730 Sq Ft

  1D Townhouse Square Unit 8, Dover, VT 05356

  Ski-on and off from this beautifully updated Seasons townhome trailside on the Mount Snow ski resort. Ski home for lunch and then get back on the slopes for the afternoon, without ever having to take off your boots. This well appointed unit features a large open concept living space with vaulted ceiling, floor to ceiling stone chimney with wood burning fireplace, tremendous natural light from the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1D Townhouse Square Unit 8, Dover, VT 05356
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  /57

  $460,000

  $65K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  57 Oak Ln, Jamaica, VT 05343

  This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

  Mike England Michael England Real Estate

  57 Oak Ln, Jamaica, VT 05343
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  /24

  $20,000

  $5K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 754 Sq Ft

  250/252 Q4, 89 Grand Summit Way Unit 250/252, Dover, VT 05356

  Enjoy the ski-on, ski-off lifestyle, while also experiencing the luxuries of hotel amenities with this spacious valley facing quarter share unit at the beautiful Grand Summit Hotel, directly at the base of Mount Snow! This sleep 6 condo is comprised of a studio unit (unit 252) with a queen murphy bed, kitchenette, sitting area and a full bathroom. This unit adjoins a hotel unit (unit 250) with 2

  Prema Fitzpatrick Real Broker LLC

  250/252 Q4, 89 Grand Summit Way Unit 250/252, Dover, VT 05356
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  /43

  $2,000,000

  • 6 Beds
  • 4.5 Baths
  • 4,950 Sq Ft

  43 Upton Rd, Dover, VT 05356

  The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end

  Adam Palmiter Berkley & Veller Greenwood/Dover

  43 Upton Rd, Dover, VT 05356
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  /42

  $695,000

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

  54 Main St, Grafton, VT 05146

  This home IS quintessential Grafton Vermont! Built c. 1850 this stately 4 over 4 colonial served as the Parsonage for the Grafton Church as it is still referred to this day. Privately owned for nearly 30 years this handsome home is ready for new stewardship. Spacious and sturdy, this vintage gem offers plenty of space and has been updated for today’s lifestyle. The first floor offers open concept

  Jessica Landers Barrett and Valley Associates Inc.

  54 Main St, Grafton, VT 05146
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  /20

  $90,100

  • Land
  • 21,780 Sq Ft
  • $180,200 per Acre

  LOT 3 158/160 High Peak Way, Wilmington, VT 05363

  A opportunity to own this .50-acre double lot in the High Peak Development, offering a double lot for your Vermont getaway. Ideally situated adjacent to the Haystack Golf Course, this parcel provides the perfect mountain convenience. Just a short drive to Mount Snow**, The Hermitage Club, and all the year-round recreation the Deerfield Valley is known for, this property also offers direct access

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  LOT 3 158/160 High Peak Way, Wilmington, VT 05363
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  /32

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  15 Bears Den Rd, Dover, VT 05356

  A rare opportunity to enjoy the best of both worlds — the privacy of a single-family home with the convenience and access of condo-style living. This unique vacation home offers direct ski-home access in the sought-after Bears Crossing community on the slopes of Mount Snow. Ski back from the Carinthia trails and step out of your gear just across the street from your front door. Designed with both

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Bears Den Rd, Dover, VT 05356
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  /2

  $195,000

  • Land
  • 4.86 Acres
  • $40,123 per Acre

  1036 Dalewood Rd, Jamaica, VT 05343

  This is a town tax sale property. There is a 30-day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residents object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5% of the town's registered voters, the Select Board cannot just sell the

  Carrie Mathews Winhall Real Estate

  1036 Dalewood Rd, Jamaica, VT 05343
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  /28

  $325,000

  $25K PRICE INCREASE

  • 5 Beds
  • 3 Baths
  • 2,209 Sq Ft

  16 Washington St, Brattleboro, VT 05301

  Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
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  /43

  $625,000

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

  15 Bills Rd, West Wardsboro, VT 05360

  This spacious four-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it’s perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  15 Bills Rd, West Wardsboro, VT 05360
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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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  /4

  $55,000

  • Land
  • 1.05 Acres
  • $52,381 per Acre

  31 Woodsman Rd, West Dover, VT 05356

  Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. The Woodsman development features large private home sites affording great privacy with thick tree buffers, public sewer hookups, easy access of a paved road nearby and tremendous site potential. This lot has been priced to sell!

  Adam Palmiter Berkley & Veller Greenwood/Dover

  31 Woodsman Rd, West Dover, VT 05356
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  /59

  $675,000

  $25K PRICE DROP

  • 6,144 Sq Ft

  2170 N Main St, Londonderry, VT 05148

  For more than 20 years, this mixed-use property has been consistently operated and maintained by the same owner—an indicator of stability, reliability, and proven performance. The building features three distinct income channels: a fully equipped small-town diner with loyal local traffic, a well-established general market serving the community’s daily needs, and two rental apartments above that

  Jessica Ackley

  2170 N Main St, Londonderry, VT 05148
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  /4

  $499,000

  $41K PRICE DROP

  • 6,000 Sq Ft

  16 School St, Brattleboro, VT 05301

  Attention Investors & 1031 Exchange Buyers! A premier, turn-key investment opportunity is now available in the high-demand Brattleboro rental market. Offered at $540,000, this massive, stately 6-unit multifamily building delivers immediate, fully stabilized cash flow from day one. With a robust gross monthly income of $7,675 and an outstanding gross annual income of $92,100, this property is a

  Kate Barry EXP Realty

  16 School St, Brattleboro, VT 05301
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  /25

  $389,900

  • 5 Beds
  • 2 Baths
  • 2,168 Sq Ft

  88 Happy Haven Rd, Wilmington, VT 05363

  Sweet Country Retreat Near Mount Snow & The Hermitage ClubTucked away on a quiet private road in the heart of Wilmington, this charming country home offers the perfect blend of privacy, comfort, and four-season Vermont living. Just minutes from Mount Snow and the exclusive Hermitage Club, this spacious property is an ideal mountain getaway, full-time residence, or investment opportunity.

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  88 Happy Haven Rd, Wilmington, VT 05363
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  /2

  $150,000

  • Land
  • 2.05 Acres
  • $73,171 per Acre

  00 Fort Dummer Heights, Brattleboro, VT 05301

  Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

  Christine Lewis Brattleboro Area Realty

  00 Fort Dummer Heights, Brattleboro, VT 05301
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  /26

  $32,000

  • 1 Bed
  • 2 Baths
  • 791 Sq Ft

  249/251 Qtr 3 Grand Summit Way Unit 249/251 Qtr 3, Dover, VT 05356

  Trailside, best ski in/out mountain location. A really comfortable unit sleep 8. Unit 251 includes a kitchenette, comfortable living room setting, a sleep sofa a Murphy bed and full bath. Unit 249 boasts 2 queen size beds a full bathroom, and a deck with views of the mountain to enjoy skiers on the slope and fireworks. Just imagine entertaining family and friends! Benefits of ownership include

  Sheila Joyce-Albano Skihome Realty

  249/251 Qtr 3 Grand Summit Way Unit 249/251 Qtr 3, Dover, VT 05356
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  /60

  $565,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  3148 Route 11, Londonderry, VT 05148

  Acreage with so much potential! Looking for a piece of Vermont to call your own? Look no further then this beautiful home looking for new owners to love and enjoy it like the current owners have. Perfectly situated in Londonderry, Vermont near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done updates to the home and property but have left spots for the new owners to still put

  Erin Kendall EXP Realty

  3148 Route 11, Londonderry, VT 05148
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  /5

  $380,000

  • 6 Beds
  • 4 Baths
  • 3,264 Sq Ft

  25 Cottage St, Brattleboro, VT 05301

  Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

  Christine Lewis Brattleboro Area Realty

  25 Cottage St, Brattleboro, VT 05301
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  /26

  $75,000

  • Land
  • 1 Acre
  • $75,000 per Acre

  170 Maple Dr, Wardsboro, VT 05355

  Are you looking for a beautiful, build-ready lot in Southern Vermont? This one-acre parcel at 170 Maple Drive in the Snow Mountain Farms community offers the perfect opportunity to start your Vermont dream home. The property already has a state-issued 4-bedroom wastewater permit in place, making it ready for your 2026 build. Located on a town-maintained road with a quiet cul-de-sac setting, this

  Chris Lowe Lowe's Real Estate, LLC

  170 Maple Dr, Wardsboro, VT 05355
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  /36

  $650,000

  • 3 Beds
  • 3.5 Baths
  • 2,678 Sq Ft

  177 Alwin Ln, Jamaica, VT 05343

  Nestled in a peaceful and private mountain setting, this beautifully maintained home offers a seamless blend of comfort, functionality, and timeless Vermont charm. Thoughtfully updated and designed for easy living.The main level features a spacious primary suite with custom built-in cabinetry, a convenient mudroom, and an updated kitchen highlighted by Vermont Verde marble countertops and

  Helen Nault

  177 Alwin Ln, Jamaica, VT 05343
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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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  /41

  $825,000

  $50K PRICE DROP

  • 7 Beds
  • 6.5 Baths
  • 1,152 Sq Ft

  136 Vermont Route 100, Dover, VT 05356

  Residential Property with Income Potential Near Mount Snow Discover a rare opportunity to own a versatile residential property with multiple income streams, located just minutes from the village of West Dover and the Mount Snow Resort area. Whether used as a primary residence, second home, or investment property, this offering provides exceptional flexibility. The main residence features a

  Cyd Scott Cohn & Company

  136 Vermont Route 100, Dover, VT 05356
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  /15

  $475,000

  $55K PRICE DROP

  • Land
  • 30 Acres
  • $15,833 per Acre

  00 W Hill Rd S, Jamaica, VT 05343

  Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

  Jacki Murano Southern Vermont Realty Group

  00 W Hill Rd S, Jamaica, VT 05343
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  /26

  $599,000

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

  10 Grouse Ln Unit 10A, Dover, VT 05356

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

  Adam Palmiter Berkley & Veller Greenwood/Dover

  10 Grouse Ln Unit 10A, Dover, VT 05356
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  /30

  $137,000

  $2K PRICE DROP

  • Land
  • 20.1 Acres
  • $6,816 per Acre

  251 Phillips Hill Rd, West Halifax, VT 05358

  Discover 20.10 acres of land in Halifax, Vermont, just a short drive to Greenfield, MA, and from skiing at Mount Snow and The Hermitage Club. This property consists of two separately deeded building lots, offering flexibility for two homes or a single retreat. Enjoy seasonal mountain views, peaceful surroundings, and direct access from a quiet country road. In the warmer months, take advantage of

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  251 Phillips Hill Rd, West Halifax, VT 05358
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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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  /13

  $195,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,591 Sq Ft

  3 Gove St, Bellows Falls, VT 05101

  This property has been used for family only for many years. Three years ago the first floor was was converted to short term housing primarily for traveling medical professionals which has been very successful, never vacant. Second floor is a two level apartment and has been owner occupied. It consists of living room, office, dining room, full bath and kitchen on the first level and 2 spacious

  Oona Madden Berkley & Veller Greenwood Country

  3 Gove St, Bellows Falls, VT 05101
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  /43

  $110,000

  $15K PRICE DROP

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

  1940 Vermont 30, Jamaica, VT 05343

  YES this is a FULL time Residence ... Charming two-bedroom, two-bathroom mobile home situated along the scenic West River. The property includes two small storage buildings, a fruit tree screened enclosure, and a carport. Inside, there is ample space for comfort with two living rooms, one of which opens to a deck with picturesque views of the river. Located just 30 minutes from Stratton, Mount

  Mike England Michael England Real Estate

  1940 Vermont 30, Jamaica, VT 05343
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  /60

  $2,895,000

  • 6 Beds
  • 4 Baths
  • 3,946 Sq Ft

  2060 Townshend Rd, Grafton, VT 05146

  A rare opportunity to own one of Southern Vermont's most remarkable private estates, Riverledge Farm encompasses more than 300 acres in the historic village of Grafton. Nestled in the Green Mountains, this exceptional property combines natural beauty, recreation, and a large homestead. A winding approach framed by mature maple trees and classic stone walls leads to the elegant white farmhouse,

  Erin McCormick KW Vermont

  2060 Townshend Rd, Grafton, VT 05146
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  /2

  $45,000

  • Land
  • 10,890 Sq Ft
  • $180,000 per Acre

  45 Mowing Way, Wilmington, VT 05363

  Level building lot with public sewer and water at the street. Across from the Haystack Golf Course for easy year round enjoyment. Direct snowmobile access from the lot. A short drive to the public boat launch at Lake Whitingham or Mount Snow ski resort.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Mowing Way, Wilmington, VT 05363
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  /24

  $140,000

  • Land
  • 1.4 Acres
  • $100,000 per Acre

  0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363

  Build your dream mountain retreat on this exceptional 1.4-acre double lot (Lots 494 & 495) in the highly desirable Chimney Hill community. Gently sloping and situated at approximately 2,400 feet in elevation, this unique parcel offers outstanding privacy with seasonal winter valley views while directly abutting Green Mountain National Forest and HOA common land, helping preserve the peaceful

  Grayson VanHendrick Flex Realty

  0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363
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  /36

  $389,000

  • 7 Beds
  • 5 Baths
  • 3,460 Sq Ft

  733 Vermont 121, Westminster, VT 05101

  This 5-unit multi-family property presents a strong investment opportunity with steady, long-term tenants and consistent on-time rental history. Meticulously cared for over the years, the property features updated systems, public water, a double lot, and ample parking for tenants and guests alike. Current rents are below today’s market rates, offering clear opportunity for future income growth

  Morriah Adams BHG Masiello Brattleboro

  733 Vermont 121, Westminster, VT 05101
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  /47

  $1,140,000

  $60K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,193 Sq Ft

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont hidden treasure at 70 Hunter Lane, set within the private Highland Forest community in the Cole Pond community . Just five minutes to Stratton Mountain Resort, this exceptional property offers the perfect balance of privacy, convenience, and year-round recreation. This 4,200 square foot home features four bedrooms and three Bathrooms. The generous living spaces

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
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  /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
• 

  

  /23

  $78,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  4 Reservoir Rd, Brattleboro, VT 05301

  In a very private area of the Park. Right out your door is the walking path to Pleasant Valley Reservoir! This 2 bedroom home has an updated bathroom. There's a concrete grilling/patio pad, lovely flower beds line the front yard and the front and back entryway are covered.

  Victoria Woods Brattleboro Area Realty

  4 Reservoir Rd, Brattleboro, VT 05301
• 

  

  /23

  $470,000

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft

  6D White Oaks Loop Unit 7, Dover, VT 05356

  OPEN HOUSE ~ Memorial Day Weekend ~ Sunday May 24th ~ 12:00-2:00pm ~ Welcome to this spacious end-unit Timber Creek condominium, ideally located directly across from Mount Snow. This highly desirable community offers the perfect blend of mountain convenience and resort-style amenities, making it an exceptional year-round getaway. The main level features a welcoming mudroom entry with built-in

  Monique White Deerfield Valley Real Estate

  6D White Oaks Loop Unit 7, Dover, VT 05356

Showing Results 161 - 200, Page 5 of 11