Windham County VT Houses for Sale

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  /39

  $1,750,000

  • 7 Beds
  • 5 Baths
  • 4,649 Sq Ft

  4669 Vermont Route 100, Londonderry, VT 05148

  Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with

  Story Jenks LandVest, Inc/Woodstock

  4669 Vermont Route 100, Londonderry, VT 05148
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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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  /60

  $749,000

  • 4 Beds
  • 4 Baths
  • 2,964 Sq Ft

  16 Rock Split Way, Wilmington, VT 05363

  Turnkey mountain retreat with style, space, and serious four-season fun—welcome to Chimney Hill living at its best. This beautifully crafted 4 bedroom home offers 4 full tiled baths and approximately 3,000 sq ft of warm, inviting living space on 3 levels designed for gathering, relaxing, and making memories. The open concept main level delivers instant wow factor with soaring cathedral ceilings,

  Chad Lackey Deerfield Valley Real Estate

  16 Rock Split Way, Wilmington, VT 05363
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  /27

  $380,000

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  34 Main St, Wardsboro, VT 05355

  Lovely late 1800s farmhouse conveniently located in the village of Wardsboro, Vermont, just a short drive to both Mount Snow and Stratton ski resorts. Meticulously maintained, the home sits on a well-positioned parcel with ample parking, private lawn space, and direct snowmobile trail access, plus easy walking access to the nearby convenience store for everyday necessities. Inside, the home

  Adam Palmiter Berkley & Veller Greenwood/Dover

  34 Main St, Wardsboro, VT 05355
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  /26

  $625,000

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft

  68 Ellis Brook Rd, Dover, VT 05341

  Gorgeous updated chalet on a private 2-acre parcel with mountain views and easy access to Mount Snow. Nestled in the desirable Dover Hills, this charming country retreat offers privacy befitting a year-round getaway, yet is just a short drive to the Mount Snow ski resort. Ample parking off a paved road, generous lawn space for play or pets, a garden shed, and excellent sun exposure complete the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 Ellis Brook Rd, Dover, VT 05341
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  /36

  $749,000

  • 4 Beds
  • 4 Baths
  • 3,691 Sq Ft

  42 Airport Rd, Shaftsbury, VT 05262

  Set just minutes from world class skiing at Mount Snow, this inviting timber frame home offers comfort, convenience, and year-round adventure right outside your door. Located just off the Mount Snow Golf course and with direct access to VAST snowmobile trails, this property is perfectly positioned for ski weekends, snowmobiling adventures, summer hiking, and everything in between. Inside, you’ll

  Mike Masters Four Seasons Sotheby's Int'l Realty

  42 Airport Rd, Shaftsbury, VT 05262
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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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  /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

  $549,000

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

  35 Upper Bartonsville Rd, Chester, VT 05143

  Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home

  Erin Kendall EXP Realty

  35 Upper Bartonsville Rd, Chester, VT 05143
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  /38

  $1,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,965 Sq Ft

  26 Springhill Rd, Dover, VT 05301

  This spectacular Post & Beam home is located just off the 13th hole of the Mount Snow Golf Course just minutes from the Mount Snow ski area. Nestled in a quiet community, with tremendous curb appeal, enjoy year round enjoyment thanks to the adjacent course, for obvious summer fun, but also snowshoeing and hiking in the winter. The interior of the home is about as good as it gets when looking for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  26 Springhill Rd, Dover, VT 05301
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  /45

  $380,000

  • 5 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  1033 Burrington Hill Rd, Whitingham, VT 05361

  Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's

  Monique White Deerfield Valley Real Estate

  1033 Burrington Hill Rd, Whitingham, VT 05361
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  /46

  $898,000

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

  41 Two Brook Dr, Wilmington, VT 05363

  Tucked onto .50-acre setting with Two Brook gently flowing through the backyard, this beautifully appointed 4 bedroom, 5 bath home captures everything buyers love about Vermont mountain living privacy, warmth, and year-round recreation just minutes from it all.Ideally located near The Hermitage Club and Mount Snow, with direct access to VAST snowmobile trails and a short drive to the shops

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  41 Two Brook Dr, Wilmington, VT 05363
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  /27

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,306 Sq Ft

  32 Old Town Rd, Dover, VT 05356

  Lovely mountain and sunset views from this absolutely immaculate home just south of the Mount Snow ski resort. Enjoy total privacy yet easy access to skiing, direct access to snowmobile trails, and nearby access to the villages of Wilmington and Dover for shopping and dining. The property consists of a level 2 acres with swimming pond, lawn space for summer fun, stone patio, storage shed, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  32 Old Town Rd, Dover, VT 05356
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  /16

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  39 Atwood St, Brattleboro, VT 05301

  First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

  Christine Lewis Brattleboro Area Realty

  39 Atwood St, Brattleboro, VT 05301
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  /39

  $295,000

  • 4 Beds
  • 1 Bath
  • 1,248 Sq Ft

  552 - 554 Hinesburg Rd, Brattleboro, VT 05301

  Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

  Steve Schoppmeyer BHG Masiello Brattleboro

  552 - 554 Hinesburg Rd, Brattleboro, VT 05301
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  /60

  $429,000

  • 3 Beds
  • 3 Baths
  • 2,690 Sq Ft

  26 N Wind Rd, Wilmington, VT 05363

  Rustic Country Home This inviting rustic country home features a spacious great room with a vaulted ceiling and a beautiful fieldstone fireplace with a buckstove—perfect for cozy winter nights. A large dining area offers plenty of space for gathering with family and friends, complemented by an awesome bar ideal for entertaining. The first floor includes a generously sized bedroom, while the

  Rich Caplan Deerfield Valley Real Estate

  26 N Wind Rd, Wilmington, VT 05363
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  /31

  $459,000

  • 1 Bed
  • 2.5 Baths
  • 2,076 Sq Ft

  33 W Main St, Wilmington, VT 05363

  Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or

  Adam Palmiter Berkley & Veller Greenwood/Dover

  33 W Main St, Wilmington, VT 05363
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  /60

  $599,000

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

  673 Vermont 121, Grafton, VT 05146

  Historic Charmer, this c. 1830 farmhouse has been loved and stewarded by its current owners for half a century. It is time to pass this amazing vintage home on to another lucky family. The house has original features including 2 fireplaces, curved plaster walls and beautiful honey colored wide pine floors. The first floor offers an eat-in- kitchen, formal dining room, spacious sunny living room

  Janet Lucier Barrett & Valley Assoc. Inc

  673 Vermont 121, Grafton, VT 05146
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  /50

  $565,000

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

  3148 Route 11, Londonderry, VT 05148

  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 their own finishing touches on

  Erin Kendall EXP Realty

  3148 Route 11, Londonderry, VT 05148
• 

  /2

  $95,000

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft

  321 Williams St, Brattleboro, VT 05301

  Opportunity to live and invest in upgrades for your new home.

  Susan Bellville Bellville Realty

  321 Williams St, Brattleboro, VT 05301
• 

  

  /31

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  68 E Brook Crossing, Wilmington, VT 05363

  Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington and south of the Mount Snow ski resort. This home sits on a private lot with direct snowmobile trail access, great for summer hiking and biking, nearby access to Lake Whitingham, and is just a short drive into the downtown for shopping and dining. Inside you are treated to a vaulted living space with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 E Brook Crossing, Wilmington, VT 05363
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  /54

  $695,000

  • 6 Beds
  • 3 Baths
  • 2,740 Sq Ft

  1161 Little Pond Rd, Londonderry, VT 05148

  Set along a quintessential Vermont country road just moments from the pristine waters of Lowell Lake, this versatile property offers the rare opportunity to enjoy peaceful rural living with flexible multi-family potential. Surrounded by natural beauty and year-round recreation, the setting is both private and convenient to all that Londonderry has to offer. The home features approximately 2,700

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1161 Little Pond Rd, Londonderry, VT 05148
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  /26

  $179,000

  • 4 Beds
  • 2 Baths
  • 2,470 Sq Ft

  1153 Rockingham Rd, Town of Rockingham, VT 05101

  Calling all investors and handy people! This is your opportunity to bring a classic property back to its former glory. Set on approximately 8.67 acres with frontage along the Williams River and Route 103, the location offers endless potential for a variety of uses. The spacious home appears to have solid bones but will require rehabilitation to restore its charm. A concrete slab is already in

  Chelsea Richardson Barrett and Valley Associates Inc.

  1153 Rockingham Rd, Town of Rockingham, VT 05101
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  /55

  $389,000

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

  1 Frog Hollow, Wilmington, VT 05363

  Charming Rustic Country Saltbox on Lower Chimney HillNestled in a convenient Lower Chimney Hill location, this rustic country saltbox offers cozy comfort and classic Vermont charm. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace that keeps the house warmed right up, the home provides a warm and inviting atmosphere year-round.Outdoor enthusiasts will

  Rich Caplan Deerfield Valley Real Estate

  1 Frog Hollow, Wilmington, VT 05363
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  /33

  $249,000

  • 2 Beds
  • 1 Bath
  • 1,004 Sq Ft

  662 Vt Route 30, Newfane, VT 05345

  Whether you’re just starting out with your first home or looking to downsize and simplify, this sweet home is just the right size. It features two bedrooms plus bonus room upstairs, with a full bathroom conveniently located on the first floor. The kitchen is charming, complete with a dishwasher, newer refrigerator and stove, opens to a dining area, and a spacious living room with beautiful wood

  Rebecca Seymour Brattleboro Area Realty

  662 Vt Route 30, Newfane, VT 05345
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  /23

  $474,900

  • 3 Beds
  • 2.5 Baths
  • 1,548 Sq Ft

  28 Lightning Ledge Way, Wilmington, VT 05363

  Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Lightning Ledge Way, Wilmington, VT 05363
• 

  

  /41

  $875,000

  • 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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  /50

  $2,099,000

  • 5 Beds
  • 5.5 Baths
  • 5,235 Sq Ft

  6 Trail View Ln, Dover, VT 05356

  Enjoy stunning views, privacy, and luxury, from a rare offering of a home at the Peaks at Mt Snow. This luxury community sits above the Greenspring development, directly across from the ski slopes at Mount Snow, with access to all the great amenities including club house, gym, indoor pool and hot tub, tennis courts, game room, on site management company, and direct shuttle service between your

  Adam Palmiter Berkley & Veller Greenwood/Dover

  6 Trail View Ln, Dover, VT 05356
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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
• 

  

  /43

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 2,496 Sq Ft

  60 Higley Hill, East Dover, VT 05341

  Welcome to 60 Higley Hill — a well-equipped country home on just over 5 acres, offering comfort, convenience, and value in one of Dover’s desirable areas. The property features a standing seam metal roof, a brand-new septic system, and a 600-ft well drilled within the last 10 years, providing peace of mind for water and waste systems. Inside, enjoy the convenience of a first-floor bedroom, a

  Erica Reynolds Southern Vermont Realty Group

  60 Higley Hill, East Dover, VT 05341
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  /44

  $279,900

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  10 King St, Bellows Falls, VT 05101

  Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With

  Floyd Amidon Maple Leaf Realty

  10 King St, Bellows Falls, VT 05101
• 

  

  /21

  $489,000

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  12 Lilla Ln, Wilmington, VT 05363

  Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

  Adam Palmiter Berkley & Veller Greenwood/Dover

  12 Lilla Ln, Wilmington, VT 05363
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  /59

  $425,000

  • 5 Beds
  • 3 Baths
  • 1,440 Sq Ft

  135 Overlook Dr, Londonderry, VT 05148

  Investment opportunity! This beautiful ski country compound offers 3 streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped

  Zachary Zupan EXP Realty

  135 Overlook Dr, Londonderry, VT 05148
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  /39

  $890,000

  • 5 Beds
  • 3.5 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  This majestic log home offers peaceful mountain living with room for Everyone. Discover your tranquil 5-bedroom, 4-bathroom family retreat nestled just minutes from the year-round activities at Stratton Ski Resort. This authentic and expansive log cabin exudes classic Vermont charm. The inviting main living area is flooded with natural light, featuring an efficient wood stove to provide cozy

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  4880 Pikes Falls Rd, Jamaica, VT 05343
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  /42

  $499,990

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  555 Vermont 9, Wilmington, VT 05363

  MOTIVATED SELLER WITH A NEW PRICE IMPROVEMENT! This brand-new construction, three-bedroom, two-bath residence blends modern comfort with classic Vermont charm and sits on a desirable double lot, offering both space and privacy. Designed for year-round living or a weekend retreat, the home features a bright, open-concept layout filled with natural light from high-quality Anderson windows and

  Colt Hazell Flex Realty

  555 Vermont 9, Wilmington, VT 05363
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  /33

  $2,100,000

  • 7 Beds
  • 4 Baths
  • 4,256 Sq Ft

  121 Fannie Hill Dr, Wilmington, VT 05363

  Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  121 Fannie Hill Dr, Wilmington, VT 05363
• 

  

  /39

  $285,000

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

  70 Overlook Dr, Londonderry, VT 05148

  Welcome Home!!! Located close to town but in a private and quiet area, this property offers an affordable option for locals and first-time homebuyers who want to be in one of Vermont’s best little communities and are willing to make the time and investment to turn this house into a home. The house is solid and has been well-maintained, and there are three bedrooms and 1.5 bathrooms and a nice

  Claudia Harris Mary Mitchell Miller Real Estate

  70 Overlook Dr, Londonderry, VT 05148
• 

  

  /41

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,091 Sq Ft

  798 Vermont Route 100, Wilmington, VT 05363

  Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  798 Vermont Route 100, Wilmington, VT 05363
• 

  

  /36

  $382,000

  • 6 Beds
  • 2.5 Baths
  • 3,590 Sq Ft

  88 Westminster St, Town of Rockingham, VT 05101

  Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 15 rooms, 6 bedrooms and the potential for 4 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period

  Jamie Watson BHG Masiello Keene

  88 Westminster St, Town of Rockingham, VT 05101
• 

  

  /45

  $798,000

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  619 Stratton Arlington Rd, West Wardsboro, VT 05360

  Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  619 Stratton Arlington Rd, West Wardsboro, VT 05360

Showing Results 41 - 80, Page 2 of 4