Windham County VT Homes for Sale

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  /39

  $925,000

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

  9D Dover Springs Ln, Dover, VT 05356

  Stunning updated Greenspring unit, just across the street from the Mount Snow ski resort with stunning direct views of the ski trails. This 4 bedroom, 4 bath unit features extensive upgrades, new furnishings, and immaculate condition, to ensure turn key enjoyment. Features include an open concept great room with vaulted ceiling and wood burning two sided fireplace, sunny exposure and sunset/ski

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9D Dover Springs Ln, Dover, VT 05356
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  /28

  $1,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,476 Sq Ft

  3B Freestyle Cir, Dover, VT 05356

  Trailside luxury at the base of the Mount Snow ski resort just off the Snowdance ski trail. This spectacular 2016 unit is just about as close and turn key as you can find. Amazing convenience to the mountain thanks to direct ski trail access, affording the ability to stop by to warm up or get a bite, yet with easterly views and a size usually only found in off mountain properties. The large

  Adam Palmiter Berkley & Veller Greenwood/Dover

  3B Freestyle Cir, Dover, VT 05356
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  /46

  $940,000

  • 3 Beds
  • 4.5 Baths
  • 3,318 Sq Ft

  42 Sugar House Rd, West Dover, VT 05356

  Tucked into the serene hills of Dover, Vermont, this custom crafted mountain home offers the ideal blend of rustic charm and modern comfort just minutes from Mount Snow and The Hermitage Club. Set on a private lot with winter views of both ski mountains, this 3-bedroom(+bonus bedroom), 4.5-bath home features an open-concept layout with soaring cathedral ceilings, exposed beams, and a stunning

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  42 Sugar House Rd, West Dover, VT 05356
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  /11

  $250,000

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

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

  Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

  Christine Lewis Brattleboro Area Realty

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
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  /6

  $795,000

  • 3 Beds
  • 2 Baths
  • 1,267 Sq Ft

  635 Vermont Route 100, Wardsboro, VT 05355

  Great short term or long term rental for investment or use by a large family. Rent one and enjoy the other. Located 1.6 miles north of Mt. Snow with direct access to VAST from this property. This home was renovated in 2014 including a new roof, windows and doors. Current owners replaced hot tub 2 years ago and a tankless water heater 3 years ago. THIS PROPERTY IS ALSO BEING SOLD WITH LISTING

  Ginny Read Read Realty LTD

  635 Vermont Route 100, Wardsboro, VT 05355
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  /8

  $795,000

  • 4 Beds
  • 3 Baths
  • 2,142 Sq Ft

  633 Route 100, West Wardsboro, VT 05360

  Great short or long term rental for investment or use by a large family. Rent one and enjoy the other. Located 1.6 miles north of Mount Snow and with direct access to VAST from this property. This home was renovated in 2014 including new ro0f, windows & doors. Current owners replaced the hot tub 1 year ago and the tankless water heater 3 years ago. Being sold furnished and ready for family,

  Ginny Read Read Realty LTD

  633 Route 100, West Wardsboro, VT 05360
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  /30

  $698,000

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

  10 Grouse Ln, Dover, VT 05356

  Welcome to your perfect Vermont getaway! This spacious 4 bedroom, 3 bathroom townhome is ideally located adjacent to the Mount Snow Golf Course, offering year-round enjoyment. Just a short drive to both Mount Snow and The Hermitage Club, you'll have easy access skiing, golfing, dining, and all that Southern Vermont has to offer.Step inside to find a warm and inviting interior, highlighted by

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  10 Grouse Ln, Dover, VT 05356
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  /24

  $20,000

  • 1 Bed
  • 2 Baths
  • 840 Sq Ft

  89 236 Qtr. 2 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

  Kelly Agrillo Southern Vermont Realty Group

  89 236 Qtr. 2 Grand Summit Way, Dover, VT 05356
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  /27

  $3,125,000

  • 4 Beds
  • 4 Baths
  • 4,333 Sq Ft

  56 Coldbrook Crossing, Wilmington, VT 05363

  Spectacular custom home at the base of the Hermitage Club in the Coldbrook Crossing community, adjacent to the base of Haystack mountain. This is a stunning lot overlooking the trails and sunsets beyond, with easy mountain access, snowmobile trail access, and views unimpeded by any other homes. The luxurious features include a vaulted great room with exposed natural wood beams and stone hearth

  Adam Palmiter Berkley & Veller Greenwood/Dover

  56 Coldbrook Crossing, Wilmington, VT 05363
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  /10

  $29,999

  • Land
  • 1.1 Acres
  • $27,272 per Acre

  4 Antler Loop, Dover, VT 05356

  Wooded Acre Close to Skiing at Mount SnowBeautiful wooded parcel less than ten minutes from skiing at Mount Snow and all the attractions in downtown Dover.While the property's address is technically 4 Antler Loop, it's much easier to access off the end of Timberview Road, which is one street up the hill. After passing by a gorgeous home at 15 Timberview, the road swaps over from

  David White OwnerEntry.com

  4 Antler Loop, Dover, VT 05356
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  /51

  $899,800

  • 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
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  /16

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  10 Riverfront Dr, Bellows Falls, VT 05101

  This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

  Gale Alger Alger Real Estate Agency

  10 Riverfront Dr, Bellows Falls, VT 05101
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  /26

  $497,500

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

  28 Country Club Rd, Dover, VT 05356

  Beautifully updated and rustic chalet just south of Mount Snow and near the Mount Snow golf course and Valley Trail. This home sits on a wooded private lot but with amazing convenience just up from a MOOver shuttle drop off location, on a paved road, with easy access to nearby trails. Just about everything has been updated to make this a turn key property, and ready for immediate enjoyment.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Country Club Rd, Dover, VT 05356
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  /8

  $35,000

  • Land
  • 5 Acres
  • $7,000 per Acre

  0 Ober Hill Rd, Townshend, VT 05353

  Escape to your own private piece of Vermont with this beautiful 5-acre sloping wooded property. Located off the beaten path, yet conveniently close to route 30, you’ll find a peaceful forest of mature Oak, Ash and Pine trees. Whether you're a camping enthusiast or seeking a serene hideaway, this land offers a spectacular setting. Property is accessed at the end of an old town road that is no

  Rebecca Hiam Southern Vermont Realty Group

  0 Ober Hill Rd, Townshend, VT 05353
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  /6

  $239,000

  • Land
  • 1.57 Acres
  • $152,229 per Acre

  2 Gold Medal Cir, Stratton, VT 05343

  This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont.

  Andrew King Stratton Real Estate

  2 Gold Medal Cir, Stratton, VT 05343
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  /30

  $139,000

  • Land
  • 20.1 Acres
  • $6,915 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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  /60

  $895,000

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft

  266 Ursa Ridge Rd, Dummerston, VT 05301

  This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

  Randi Ziter Brattleboro Area Realty

  266 Ursa Ridge Rd, Dummerston, VT 05301
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  /27

  $559,000

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  16 View Rd, Wilmington, VT 05363

  Great Chimney Hill vacation home in Lower B section. Super layout where kitchen, counter conversers, dining room folks and living room relaxers can choose to interact as one happy group, or maintain their own separate activities. The pellet stove fireplace & vaulted ceiling in the living room make for such a relaxing space, while the steps that lead to the large loft above provides yet another

  Michael Purcell Berkley & Veller Greenwood/Dover

  16 View Rd, Wilmington, VT 05363
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  /18

  $309,900

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  164 Chestnut St, Brattleboro, VT 05301

  Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders

  Christine Lewis Brattleboro Area Realty

  164 Chestnut St, Brattleboro, VT 05301
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  /12

  $79,000

  • 3 Beds
  • 1 Bath
  • 744 Sq Ft

  100 Dorr Fitch Rd, Dover, VT 05356

  This manufactured home needs a complete overhaul and is being sold as-is, but is priced to sell! Having been taken over by critters, which have since been relocated, it would appear that it has to be gutted, but there is a steel frame, a dug well, and cesspool. Thanks to sewer hook up located at the street, there is great potential, as well as view potential from the rear of the property, direct

  Adam Palmiter Berkley & Veller Greenwood/Dover

  100 Dorr Fitch Rd, Dover, VT 05356
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  /35

  $795,000

  • 4 Beds
  • 5 Baths
  • 3,129 Sq Ft

  20 Ray Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a completely remodeled and updated vintage farmhouse, completely turn key. This stunning home sits just up from the country village of Wilmington with easy access to dining and shopping, a short drive to Mount Snow, and near the amazing Lake Whitingham, for true four season enjoyment. The interior features meticulously updated open concept living areas, a chef's kitchen

  Adam Palmiter Berkley & Veller Greenwood/Dover

  20 Ray Hill Rd, Wilmington, VT 05363
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  /48

  $380,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  183 Bear Hill Rd, Dummerston, VT 05301

  Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency. This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

  Kate Barry EXP Realty

  183 Bear Hill Rd, Dummerston, VT 05301
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  /6

  $90,000

  • Land
  • 3.2 Acres
  • $28,125 per Acre

  123 U S 5, Westminster, VT 05158

  Beautiful flat, open, grassy lot on Rte 5, just over the Westminster town line from Putney. This lot is completely cleared! Used for hay in the past. The house site is in the front 1/3, as the back 2 Acres is a conservation area, for agricultural use only. There are two, 2.5 acre lots available for purchase as well; separately or together. This parcel is separated from the other 2 lots by two

  Victoria Woods Brattleboro Area Realty

  123 U S 5, Westminster, VT 05158
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  /14

  $65,000

  • Land
  • 2.5 Acres
  • $26,000 per Acre

  123 U S 5, Westminster, VT 05158

  Beautiful flat, wooded lot on Rte 5, just over the Westminster town line from Putney. There are two, 2.5 acre lots available for purchase; separately or together. Additionally, there is a 3.2 acre open, grassy lot available. This is separated from the other 2 lots by two house parcels.All 3 lots are being sold with deferral language, as they do not have state permits, however they've all had

  Victoria Woods Brattleboro Area Realty

  123 U S 5, Westminster, VT 05158
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  /50

  $339,000

  • 7 Beds
  • 4 Baths
  • 3,000 Sq Ft

  89 Gates Pond Rd, Whitingham, VT 05342

  This rare multi-family home presents a unique investment opportunity, featuring four well-designed units. Nestled in the charming town of Jacksonville you're just 23 minutes from the exhilarating slopes of Mount Snow ski resort. The property offers two one-bedroom units on the first floor, alongside a spacious two-bedroom unit and a generous three-bedroom unit on the second floor. Enjoy the large

  Monique White Deerfield Valley Real Estate

  89 Gates Pond Rd, Whitingham, VT 05342
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  /60

  $1,350,000

  • 5 Beds
  • 3.5 Baths
  • 3,516 Sq Ft

  732 Under the Mountain Rd, South Londonderry, VT 05155

  Welcome to "Fairmount," a beautiful historic home with unrivaled panoramic views and an extraordinary blend of history, grace, and quintessential Vermont living on 42 acres. Originally built in 1810 and artfully reimagined in 1987, the 5BR farmhouse seamlessly merges historic charm with modern sensibility. Exposed beams, wide plank floors, and architectural character remain, while the thoughtful

  Claudia Harris Mary Mitchell Miller Real Estate

  732 Under the Mountain Rd, South Londonderry, VT 05155
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  /12

  $139,000

  • Land
  • 5 Acres
  • $27,800 per Acre

  0 Banning Rd, Putney, VT 05346

  Location is key, and locations like this don't come along often. Almost at the top of Putney Mountain is this 5+/- acres of mature hard and soft woods, including red oak, birch, beech, pine and hemlock, just waiting to host your full or part time dwelling. The existing driveway, which is shared with the seller, offers access to the length of the parcel. There's a State Wastewater Permit with a

  Bill Hickok Berkley & Veller Greenwood Country

  0 Banning Rd, Putney, VT 05346
• 

  

  /37

  $739,000

  • 3 Beds
  • 4 Baths
  • 3,352 Sq Ft

  183 Vacation Lodge Rd, Londonderry, VT 05148

  Welcome to your mountain oasis tucked away in the scenic hills of Londonderry, Vermont. This contemporary 3-bedroom, 4-bathroom home is designed for comfort, entertaining, and enjoying every season. Whether you're looking for a relaxing retreat, a rental income opportunity, or a full-time family compound, this property offers something special for everyone.Step into a space that blends

  Brian Hill Remax Summit

  183 Vacation Lodge Rd, Londonderry, VT 05148
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  /41

  $725,000

  • 3 Beds
  • 3.5 Baths
  • 4,219 Sq Ft

  5 N Main St, Wilmington, VT 05363

  Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman Reservoir, this exceptional mixed-use property offers incredible flexibility, income potential, and style. Currently operating as a successful VRBO rental that sleeps 12, this all-season retreat includes multiple living areas, a hot tub, sauna, and a stunning vaulted post-and-beam loft with a bar, pool

  Morriah Adams BHG Masiello Brattleboro

  5 N Main St, Wilmington, VT 05363
• 

  

  /17

  $150,000

  • Land
  • 2.8 Acres
  • $53,571 per Acre

  37 Fred Houghton Rd, Putney, VT 05346

  Just in time! So special! This unusual offering was a beloved family complex for many years. The land is a delight of mixed hardwoods and evergreens, easy to walk and gently rolling for intrigue. Walk to "downtown" Putney for the small town energy, pop in the auto for a short drive to everything else...interstate access, NH, skiing...hospitals and services.....or tuck in at home for a

  Christine Lewis Brattleboro Area Realty

  37 Fred Houghton Rd, Putney, VT 05346
• 

  

  /22

  $539,000

  • Land
  • 2.88 Acres
  • $187,153 per Acre

  309 Vermont Route 100, Dover, VT 05356

  Prime Investment Opportunity – Near Mount Snow Ski Resort!An exceptional development opportunity awaits just half a mile from Mount Snow Ski Resort. This level lot with stunning mountain views is ideally situated close to all area recreation – skiing, snowboarding, hiking, biking, and more.Plans for 8 units / 24 bedroomsTown sewer availableMost permits secured – only waiting on

  Rich Caplan Deerfield Valley Real Estate

  309 Vermont Route 100, Dover, VT 05356
• 

  

  /13

  $79,000

  • Land
  • 3.69 Acres
  • $21,409 per Acre

  0 Honeycomb Hill, Marlboro, VT 05301

  On the privately maintained road of Honeycomb Hill sits this 3.69 acre lot. The wooded parcel has young tree growth and slopes gently. There are three areas that are fairly level and open and may be suitable building sites. Just 30 minutes to Mt. Snow, 25 minutes to Brattleboro and 15 minutes to Harriman Reservoir, this conveniently located parcel offers easy access to all of Southern Vermont's

  Laura D'Angelo Berkley & Veller Greenwood Country

  0 Honeycomb Hill, Marlboro, VT 05301
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  /37

  $875,000

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

  25 Boulder Ridge Dr Unit B, Dover, VT 05356

  This magnificent 4-bedroom, 4-bathroom townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design, offering a living experience par excellence. This townhouse was finished in 2021 and has the “new construction” feel. The living room, graced with hardwood flooring, a gas fireplace,

  John Redd Skihome Realty

  25 Boulder Ridge Dr Unit B, Dover, VT 05356
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  /41

  $265,000

  • 4 Beds
  • 1 Bath
  • 1,612 Sq Ft

  178 Parsons Rd, Wilmington, VT 05363

  Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  178 Parsons Rd, Wilmington, VT 05363
• 

  

  /19

  $199,000

  • Land
  • 20.09 Acres
  • $9,905 per Acre

  189 North St, Dover, VT 05356

  Discover the perfect Vermont retreat on this 20.09 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  189 North St, Dover, VT 05356
• 

  

  /10

  $90,000

  • Land
  • 10.05 Acres
  • $8,955 per Acre

  Lot 3 North St, Dover, VT 05431

  Discover the perfect Vermont retreat on this 10.15 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 3 North St, Dover, VT 05431
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  /38

  $520,000

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

  829 Pennel Hill Rd, Halifax, VT 05342

  Spacious cabin set on 16.4 acres with stream and pond. Open main living area features hardwood floors, vaulted ceilings with skylights, exposed beams, and an efficient wood stove. Updated kitchen includes stainless steel appliances and breakfast bar seating.Main level bedroom with shared en suite bathroom featuring claw foot tub and walk-in shower. Spiral staircase leads to primary suite with

  Megan Quinn Southern Vermont Realty Group

  829 Pennel Hill Rd, Halifax, VT 05342
• 

  

  /9

  $120,000

  • Land
  • 10.04 Acres
  • $11,952 per Acre

  Lot 2 North St, Dover, VT 05431

  Discover the perfect Vermont retreat on this 10.48 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 2 North St, Dover, VT 05431
• 

  

  /9

  $430,000

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

  1950 N Main St, Londonderry, VT 05148

  PRICE REDUCTION! IT IS possible to Live rent or mortgage free!!! And HERE it is.This is a 3 unit multi-family, fully rented/money making property now..Live in one and let the other two pay your bills.. Or, use your imagination, create your vision of what this premier location could be. Zoned BOTH commercial AND residential.. this property could be a fabulous restaurant with rivers edge al fresco

  Wilkie Bushby TPW Real Estate

  1950 N Main St, Londonderry, VT 05148
• 

  

  /23

  $1,150,000

  • 6,442 Sq Ft

  69-71 Elliot St, Brattleboro, VT 05301

  Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

  Erica Reynolds Southern Vermont Realty Group

  69-71 Elliot St, Brattleboro, VT 05301

Showing Results 281 - 320, Page 8 of 11