Windham County VT Houses for Sale

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  /24

  $350,000

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,830 Sq Ft

  4850 Vermont Route 100, Wardsboro, VT 05355

  Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4850 Vermont Route 100, Wardsboro, VT 05355
• 

  

  

  /17

  $439,000

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  You've earned it.....the right to easy living.....have someone to do the heavy lifting...This community has become a much needed addition to the housing community. All are designed for the 55 and over who are looking for an easy way to settle in. Just think, the snowplowing, shoveling and salting are all taken care of, as well as the summer mowing and hedge trimming. One level living with no

  Christine Lewis Brattleboro Area Realty

  77 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  

  /30

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  255 Fitts Rd, Wardsboro, VT 05355

  Ready for its next stewards, this cozy home has been cherished by the same family for many years and is set on 10 acres of open land and woodlands. Enjoy a peaceful rural setting conveniently located between two of southern Vermont’s premier ski destinations: Stratton Mountain Resort and Mount Snow. At the heart of the house is an inviting kitchen featuring updated cabinets, soapstone

  Heidi Bernier Berkley & Veller Greenwood Country

  255 Fitts Rd, Wardsboro, VT 05355
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  /58

  $550,000

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

  59 Colonial Ridge Rd, Dover, VT 05356

  Located in the highly desirable Dover Hills, this beautifully maintained, custom-built 4-bedroom, 2-bath chalet offers the perfect combination of Vermont charm, comfort, and convenience. Set on a private 2-acres with easy paved access, the property is just a short drive to Mount Snow, the VAST snowmobile trail system, Harriman Reservoir, shopping, dining, and all the amenities of West Dover.

  Donald Koelsch Deerfield Valley Real Estate

  59 Colonial Ridge Rd, Dover, VT 05356
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  /39

  $520,342

  • 3 Beds
  • 3 Baths
  • 1,521 Sq Ft

  34 Rock Split Way, Wilmington, VT 05363

  Perched atop Chimney Hill, this 3-bedroom, 3-bathroom home is perfectly suited as a vacation retreat or a primary residence, offering fantastic indoor and outdoor entertaining spaces. Enter the main level via the newly expanded staircase and deck. Inside, a spacious tile entryway provides ample room for gear and clothing storage. The sunken living room, with stone fireplace, flows seamlessly into

  Megan Quinn Southern Vermont Realty Group

  34 Rock Split Way, Wilmington, VT 05363
• 

  

  /36

  $1,295,000

  $20K PRICE INCREASE

  • 5 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4427 W Hill Rd S, Jamaica, VT 05343

  One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

  Carrie Mathews Winhall Real Estate

  4427 W Hill Rd S, Jamaica, VT 05343
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  /48

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  35 Theron Fisher Rd, Grafton, VT 05146

  Nestled along the Saxtons River, moments from historic Grafton, this beautifully restored Colonial farmhouse offers a rare blend of Vermont history, modern luxury, and exceptional curb appeal. Originally built circa 1820, the home has been meticulously reimagined and rebuilt with extraordinary attention to quality and architectural integrity. The renovation includes new plumbing, electrical,

  Gary Coger Four Seasons Sotheby's Int'l Realty

  35 Theron Fisher Rd, Grafton, VT 05146
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  /32

  $1,697,000

  • 4 Beds
  • 3 Baths
  • 2,420 Sq Ft

  197 Lake Raponda Rd, Wilmington, VT 05363

  This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by

  Adam Palmiter Berkley & Veller Greenwood/Dover

  197 Lake Raponda Rd, Wilmington, VT 05363
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  /50

  $1,200,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft

  364 Houghtonville Rd, Grafton, VT 05146

  At the beginning of a dirt road just outside the historic village of Grafton VT you will find an exceptional country estate that combines timeless New England charm with modern comfort, privacy, and equestrian amenities. Thoughtfully designed to replicate a classic colonial home and extensively updated by its current owners, this meticulously maintained property offers an extraordinary lifestyle

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  364 Houghtonville Rd, Grafton, VT 05146
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  /52

  $629,900

  • 3 Beds
  • 2 Baths
  • 2,048 Sq Ft

  187 Poverty Row, Whitingham, VT 05361

  Outstanding contemporary farmhouse set on 5.3 acres of private, level acres, offering the perfect blend of comfort, space, and functionality. This well-maintained home features an open-concept first floor with a spacious great room highlighted by a cathedral ceiling. The main level also includes one bedroom and full bath, along with a convenient mudroom and laundry room.The custom maple

  Pauline Green

  187 Poverty Row, Whitingham, VT 05361
• 

  

  /43

  $679,000

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

  148 Townshend Rd, Grafton, VT 05146

  This circa 1860 Greek Revival home is one of Grafton Village’s gems, blending historic character with recent, thoughtful renovations. A sweeping backyard framed by rugged stone walls adds to the property’s appeal, while established perennials and a welcoming side porch create an inviting entrance. The delightful country kitchen flows into the formal dining room and living room, where a propane

  Heidi Bernier Berkley & Veller Greenwood Country

  148 Townshend Rd, Grafton, VT 05146
• 

  

  /27

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,530 Sq Ft

  72 Green Meadow Rd, West Brattleboro, VT 05301

  Nestled in a highly desirable West Brattleboro neighborhood, this well-cared-for home offers a wonderful community lifestyle and the ease of main-level living. The first floor features three bright bedrooms and a full bath - perfect for aging in place. Inside, you'll find classic hardwood floors and a cozy fireplace warming the living room. Step outside to an incredible, private backyard deck

  Thomas Dahlin Berkley & Veller Greenwood Country

  72 Green Meadow Rd, West Brattleboro, VT 05301
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  /28

  $235,000

  • 2 Beds
  • 1 Bath
  • 970 Sq Ft

  3153 Vermont Route 100, Wardsboro, VT 05355

  Charming 2-bedroom, 1-bath rustic cottage featuring a versatile 14x9 mudroom and plenty of recent upgrades. The spacious kitchen flows into a generous dining area, while the cozy living room offers a VT Castings woodstove, a side bar with stools, and warm, inviting finishes. Both bedrooms are nicely sized, with one offering sliding doors that open directly to the backyard perfect for easy outdoor

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  3153 Vermont Route 100, Wardsboro, VT 05355
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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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  /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
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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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  /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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  /44

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,611 Sq Ft

  279 Westminster Rd, Putney, VT 05346

  Built in 1962, this inviting home perfectly balances peaceful country living with convenient access to local amenities, including excellent public and private schools. Near to an extensive network of hiking, cross country skiing and mountain bike trails offering spectacular views. Whether seeking a peaceful retreat or an outdoorsy lifestyle, this property in a welcoming community has it all. Home

  Jonathan Minerick

  279 Westminster 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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  /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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  /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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  /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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  /53

  $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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  /29

  $289,000

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft

  110 Western Ave, Brattleboro, VT 05301

  This in town 4 bedroom, 2 bath home offers the perfect blend of comfort, convenience and versatility. Ideally located close to town amenities, this property provides easy access to shopping, dining, services, schools, parks and everyday essentials while offering a spacious place to call home. Inside you’ll find beautiful wood flooring, inviting living spaces and a layout that provides flexibility

  Wilma Skovinski Berkley & Veller Greenwood Country

  110 Western Ave, Brattleboro, VT 05301
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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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  /32

  $728,000

  $47K PRICE DROP

  • 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

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Bears Den Rd, Dover, VT 05356
• 

  

  /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
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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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  /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
• 

  

  /57

  $555,000

  $20K PRICE DROP

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

  3148 Route 11, Londonderry, VT 05148

  Located in picturesque Londonderry, Vermont on 14 spacious acres this home is looking for new owners to make it their own! Conveniently located near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done some updates to the home and property but have left spots for the new owners to still put their own finishing touches on the place! The house is very roomy with 3 bedrooms and 2

  Erin Kendall EXP Realty

  3148 Route 11, Londonderry, VT 05148
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  /31

  $375,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 3,502 Sq Ft

  715 Chase Rd, West Townshend, VT 05359

  In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for

  Christine Lewis Brattleboro Area Realty

  715 Chase Rd, West Townshend, VT 05359
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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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  /33

  $339,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  8 Beech Tree Ln, Newfane, VT 05345

  This is just the cutest little cottage you ever did see! It is just the right size not too big, not too small. This charming country cottage would be a wonderful small footprint primary home or would make an ideal weekend getaway! The first floor living space is open with lovely wood floors and a wood stove perfect for those crisp country evenings, tastefully updated kitchen, dining area, and

  Rebecca Seymour Brattleboro Area Realty

  8 Beech Tree Ln, Newfane, VT 05345
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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
• 

  

  /25

  $375,000

  • 4 Beds
  • 2.5 Baths
  • 2,066 Sq Ft

  313 Dover Rd, Newfane, VT 05362

  Step back in time while enjoying the comforts of today in this classic 1800s post-and-beam Cape set on 2 peaceful acres in the Vermont countryside. Rich in character and timeless charm, this 4-bedroom, 3-bath home showcases the warmth and craftsmanship of a bygone era with exposed beams, inviting living spaces, and room for family and guests. Outside, you’ll find established perennial gardens,

  Claire Renaud Berkley & Veller Greenwood Country

  313 Dover Rd, Newfane, VT 05362
• 

  

  /58

  $1,100,000

  $100K PRICE DROP

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

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly unique four season home. In the summer, kayak and swim on a private pond. In the fall, hike the many trails that are available and enjoy the foliage. When the Winter comes, it's a ten minute trip to Stratton Mountain and afterwards, ice skate on your own back yard pond. In the spring, step outside to a private hot tub inviting you to to soak while overlooking the sprawling

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
• 

  

  /29

  $599,000

  • 5 Beds
  • 2 Baths
  • 2,350 Sq Ft

  9282 Vt Route 100, Whitingham, VT 05361

  This Vermont Country Farmhouse has been recently completed renovated and is ready for turn key enjoyment. The property consists of 41+ acres with tremendous exposure and easy main road access, extensive pasture which could easily be used for farming, a 42x48 post and beam barn, multiple out buildings ideal for workshops and storage, and a location with easy access to Harriman Reservoir and not

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9282 Vt Route 100, Whitingham, VT 05361
• 

  

  /50

  $435,000

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  27 Country Ct, Wilmington, VT 05363

  Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous multi-use

  Janet Boyd Boyd Real Estate

  27 Country Ct, Wilmington, VT 05363

Showing Results 81 - 120, Page 3 of 6