Windham County VT Homes for Sale

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  /29

  $789,000

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

  15 Sawmill Village Way, Dover, VT 05356

  Beautiful contemporary farmhouse in the prestigious Village at Sawmill Farms, just a short drive from the Mount Snow ski resort. This bright and airy farmhouse design sits on a private level lot, and has been completely renovated to be turn key for immediate enjoyment. The interior boasts a vaulted living room with large windows, great natural light, and a gas fireplace, there is an updated chefs

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Sawmill Village Way, Dover, VT 05356
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  /30

  $305,000

  $10K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,607 Sq Ft

  136 Morningside Dr, Brattleboro, VT 05301

  Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining

  Desiree Stango Berkley & Veller Greenwood Country

  136 Morningside Dr, Brattleboro, VT 05301
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  /46

  $485,000

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

  4027 Route 100 Hwy, Wardsboro, VT 05360

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

  Steve Goldfarb Deerfield Valley Real Estate

  4027 Route 100 Hwy, Wardsboro, VT 05360
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  /32

  $875,000

  • 4 Beds
  • 4 Baths
  • 3,374 Sq Ft

  11 Stone Ridge Loop, Dover, VT 05356

  Beautiful custom home in the prestigious Village at Sawmill Farms, just a short drive from the Mount Snow ski resort. This contemporary farmhouse design has been just recently updated throughout to offer country charm with modern amenities for turn key enjoyment. The interior boasts a large great room with soaring windows, great natural light, and a new gas fireplace on stone hearth, a large

  Adam Palmiter Berkley & Veller Greenwood/Dover

  11 Stone Ridge Loop, Dover, VT 05356
• 

  

  /2

  $59,900

  • Land
  • 1 Acre
  • $59,900 per Acre

  Lot 35 Woodsman Rd, Dover, VT 05356

  Super building lots up near the Dover Elementary School. Gentle sloping lots, with municipal sewer and underground telephone & electric. Prices reflect the quality of the view(s). Some with ski area(s) to the west and others with local ridgelines to south. Only moments from West Dover dining, shopping, and skiing. The Elementary School provides a fun campus for younger recreational fun. How many

  Michael Purcell Berkley & Veller Greenwood/Dover

  Lot 35 Woodsman Rd, Dover, VT 05356
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  /60

  $850,000

  $35K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,154 Sq Ft

  157 Old Sawmill Rd, Londonderry, VT 05148

  Nestled in a peaceful Londonderry setting, 157 Old Sawmill Road offers the perfect blend of Vermont charm, comfort, and outdoor recreation. Originally built in 1971 and extensively renovated and expanded in 1992, this inviting home features nearly 3,200 square feet of living space designed for year-round enjoyment.Take in front-row views of Magic Mountain's ski trails right from your front

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  157 Old Sawmill Rd, Londonderry, VT 05148
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  /60

  $2,495,000

  $394K PRICE DROP

  • 6 Beds
  • 7 Baths
  • 6,400 Sq Ft

  56 Handle Rd, Dover, VT 05356

  Incredible Legacy Property. This extraordinary estate blends timeless elegance with modern comfort. The first floor features a welcoming den, gourmet eat in kitchen with DCS range, stainless appliances, sub- zero refrigerator and wet bar. A dining room, gracious living room, office, and butler’s panty with fridge and ice maker make entertaining effortless. Five fireplaces, custom-built-ins, wood

  Rich Caplan Deerfield Valley Real Estate

  56 Handle Rd, Dover, VT 05356
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  /10

  $139,000

  $86K PRICE DROP

  • Land
  • 9.45 Acres
  • $14,709 per Acre

  0 Higley Hill Unit 5047136, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Package lot offers considered. Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill Unit 5047136, Dover, VT 05356
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  /60

  $945,000

  • 2 Beds
  • 1.5 Baths
  • 2,721 Sq Ft

  51 Dusty Ridge Rd, Putney, VT 05346

  Nestled along one of Putney's most scenic country roads, this private 18.3 acre property offers the perfect balance of wooded privacy, open space, and classic Vermont charm. Stone walls, mature perennial gardens, walking trails, and a meandering stream create a peaceful setting. The thoughtfully designed home offers 2,721 square feet of living space with 2 bedrooms and 2 bathrooms. A soaring

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  51 Dusty Ridge Rd, Putney, VT 05346
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  /12

  $285,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  455 S Main St, Brattleboro, VT 05301

  Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

  Christine Lewis Brattleboro Area Realty

  455 S Main St, Brattleboro, VT 05301
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  /30

  $100,000

  $10K PRICE DROP

  • Land
  • 2.5 Acres
  • $40,000 per Acre

  69 Old Haven Ln, Putney, VT 05346

  Escape to your own slice of Vermont paradise with this exceptional land offering on Old Haven Lane in highly desirable Putney. This serene, pristine lot offers the perfect canvas for your custom home, tucked away for ultimate privacy yet completely accessible to Putney’s vibrant town center, local schools, and cultural landmarks. Whether you are looking to hold a premium piece of land or break

  Kate Barry EXP Realty

  69 Old Haven Ln, Putney, VT 05346
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  /14

  $50,000

  • Land
  • 12,632 Sq Ft
  • $172,414 per Acre

  41 Country Club Rd, Wilmington, VT 05363

  Set on 0.29 acres along a quiet dead-end, town-maintained paved road, this property offers a convenient and peaceful setting. The driveway is already in place, electric underground service is on site, and a natural spring is located on the property. Nearby access to the VAST Trails. Included in the sale is a 2015 Jayco Eagle Premier RV, providing comfortable seasonal living or a ready-made

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  41 Country Club Rd, Wilmington, VT 05363
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  /33

  $599,000

  $20K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,354 Sq Ft

  556 Sawmill Rd, Wardsboro, VT 05355

  Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with a dedicated office space and attached garage offers over 3,000 square feet of living space. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment from winter skiing and riding to relaxing summer

  Kim Meeker Southern Vermont Realty Group

  556 Sawmill Rd, Wardsboro, VT 05355
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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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  /20

  $24,500

  • 1 Bath
  • 673 Sq Ft

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

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? One bedroom, sleeps 6, single-le unit. Close to the elevator, the Owners Lounge, and the library. King bed, Queen sleeper sofa, Queen Murphy bed. One bathroom. Use it, rent it, trade it! Does having 13 weeks of vacation a year sound appealing? This one-bedroom unit accommodates up to six people and is conveniently located on

  Kelly Agrillo Southern Vermont Realty Group

  224 Qtr. 2, 89 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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  /60

  $8,200,000

  • 6 Beds
  • 10 Baths
  • 10,763 Sq Ft

  557 Trager Rd, Jamaica, VT 05343

  Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in

  Kim Morgan-Wohler Wohler Realty Group

  557 Trager Rd, Jamaica, VT 05343
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  /4

  $125,000

  $15K PRICE DROP

  • Land
  • 1.3 Acres
  • $96,154 per Acre

  00 Creamery Rd, Guilford, VT 05301

  Just in time for Spring building! This incredibly beautiful high meadow is perfect for your new home, be it a get away or primary. Wake up to the views of the local hills and rolling countryside...enjoy gardening, a pool, decks or covered porches ..or just install oversized windows to take advantage while you putter about! Soils tests are done...drive is into the lot...consult GMP for power...Get

  Christine Lewis Brattleboro Area Realty

  00 Creamery Rd, Guilford, VT 05301
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  /8

  $159,000

  $240K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $496,875 per Acre

  8A Freestyle Cir, Dover, VT 05356

  Ski in and out at Mount Snow from one of the last two buildable lots. In other words, if you like the convenience of slopeside living this could be the location for you to build your dream home with easy access to the mountain. This building site is part of the TrailsEdge PUD, sharing in their utilities and ski access to/from Mount Snow through the Snowdance Village ski trails. Note that this is

  John Redd Skihome Realty

  8A Freestyle Cir, Dover, VT 05356
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  /60

  $1,165,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,632 Sq Ft

  350 Sunset Lake Rd, Newfane, VT 05301

  Experience the timeless charm of Vermont living at this beautifully renovated farmhouse estate sitting on 92 acres in Newfane Vermont. Originally restored and thoughtfully updated, this exceptional antique farmhouse seamlessly blends historic character with modern comfort and convenience. Unlike many older homes, this property features expansive rooms, high ceilings, wood floors, abundant natural

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  350 Sunset Lake Rd, Newfane, VT 05301
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  /50

  $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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  /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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  /24

  $239,000

  • Land
  • 35.4 Acres
  • $6,751 per Acre

  389 Brookline Rd, Athens, VT 05143

  Set on 35.4 acres, this unique property offers privacy, natural beauty, and abundant outdoor recreation. The property includes a camp that has been used year-round in the past and is served by electricity and a drilled well. The barn features a refinished upper level currently used as an art studio with a wood stove. Extensive perennial gardens, mature fruit trees, and thoughtfully landscaped

  Jessica Hunt Barrett & Valley Assoc. Inc

  389 Brookline Rd, Athens, VT 05143
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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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  /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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  /31

  $439,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  8C Trailside Village Way Unit I13, Dover, VT 05356

  Amazing trailside, ground unit opportunity at Mount Snow. This is a beautiful and bright 2 bedroom, 2 bath unit, located adjacent to the ski-on/ski-off trail for absolutely the easiest access you can enjoy. Each unit has a ground floor ski locker to stow your gear, and then you are in and out your own rear entry to make for easy access after a day of skiing. Enjoy the spacious living space with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  8C Trailside Village Way Unit I13, Dover, VT 05356
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  /42

  $675,000

  $20K PRICE DROP

  • 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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  /18

  $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
• 

  

  /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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  /33

  $225,000

  $75K PRICE DROP

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

  16 Washington St, Brattleboro, VT 05301

  Major price reduction! This price reduction involves the seller staying on as a tenant for up to a year after closing. Ask for details! 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

  Rebecca Seymour Brattleboro Area Realty

  16 Washington St, Brattleboro, VT 05301
• 

  

  /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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  /23

  $30,000

  • Land
  • 21,780 Sq Ft
  • $60,000 per Acre

  Lot 118 High Top Rd, Wilmington, VT 05363

  Section B building lot! 1/2 Acre of level, flat land at the end of the cul-de-sac. Site is untested. Build your dream home and start planning your vacation getaway design! As a Lot owner, you may enjoy all of the recreational amenities Chimney Hill Resort offers on its 1,200 Acre Campus. Once you start building, Chimney Hill Owners Association also supplies a water line at the street for you to

  Sigrid Pickering Chimney Hill Realty

  Lot 118 High Top Rd, Wilmington, VT 05363
• 

  

  /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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  /9

  $198,000

  • Land
  • 3.27 Acres
  • $60,550 per Acre

  0 Pleasant Valley Rd, Brattleboro, VT 05301

  It doesn't get better than this! Stunning! Over 3.25 acres in a neighborhood with a wait list, well known hiking trails, near cross country skiing, country club and minutes to downtown. There are 2 lots, the front being mostly wooded with some clearing started and the rear lot with an old horse meadow, stone wall and a bit of height for potential views. Not only is there road frontage on Pleasant

  Christine Lewis Brattleboro Area Realty

  0 Pleasant Valley Rd, Brattleboro, VT 05301
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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
• 

  

  /23

  $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
• 

  

  /46

  $869,900

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

  45 Sawmill Village Way, Dover, VT 05356

  Experience the perfect blend of Vermont charm and modern comfort in this beautifully crafted custom post-and-beam home with a beautiful view, ideally located in the heart of Dover. Just minutes from Mount Snow, local restaurants, shopping, area amenities, and the scenic Valley Trail, this home offers the perfect balance of convenience and privacy in a peaceful wooded setting. Inside, many windows

  Rich Caplan Deerfield Valley Real Estate

  45 Sawmill Village Way, Dover, VT 05356
• 

  

  /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
• 

  /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
• 

  

  /60

  $565,000

  $10K PRICE DROP

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

  3148 Route 11, Londonderry, VT 05148

  Looking for useable acreage with so much potential? Looking for a piece of Vermont to call your own? Look no further then this beautiful home, situated on 14 acres, 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

  Erin Kendall EXP Realty

  3148 Route 11, Londonderry, VT 05148

Showing Results 161 - 200, Page 5 of 12