Windham County VT Homes for Sale

• 

  

  

  /54

  $325,000

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

  2015 Vermont 30, Townshend, VT 05353

  Perfectly situated on the scenic road to Stratton Mountain—just 25 minutes from the slopes—this charming turn-of-the-century mixed-use property offers endless potential. Step inside to discover original period woodwork, gleaming hardwood floors, and classic details that give this roomy home its timeless character.The property also boasts a large two-story post-and-beam barn, lovingly restored

  Craig Ruggless EXP Realty

  2015 Vermont 30, Townshend, VT 05353
• 

  

  

  /12

  $125,000

  • Land
  • 15.6 Acres
  • $8,013 per Acre

  0 Thayer Rd, Westminster, VT 05158

  Rural 15.6 acre lot located at the end of Thayer Rd off Davidson Hill Rd in Westminster. This land is located in a quiet rural community on a gravel road about 10 minutes drive from Saxtons River Village and Bellows Falls Village. The lot consist of 3 lots of record all serviced by a common Right of Way. The ROW is also shared with a abutter to the north. The ROW provides ready to use access to

  Steve Schoppmeyer BHG Masiello Brattleboro

  0 Thayer Rd, Westminster, VT 05158
• 

  

  

  /38

  $475,000

  • Land
  • 133.1 Acres
  • $3,569 per Acre

  40 E Putney Brook Rd, Putney, VT 05346

  Awesome 133± Acre Country Parcel in Putney, Vermont. A rare opportunity to own 133± acres of picturesque Vermont land in highly desirable Putney. This large country parcel offers multiple access points, including generous frontage on a major road as well as two unpaved roads. Existing logging roads weave through the property, leading to several clearings ideal for building, recreation, or

  Geralyn Donohue Engel & Völkers Okemo

  40 E Putney Brook Rd, Putney, VT 05346
• 

  

  

  /21

  $379,000

  • Land
  • 12.05 Acres
  • $31,452 per Acre

  101 Catherine Rd, Jamaica, VT 05343

  Discover 12 scenic acres close to Stratton Mountain Resort with sweeping mountain views and endless potential. This unique property features a charming small treehouse and two Jamaica cottage structures set on permanent foundations ready to be finished. Cabin would be perfect for income producing tiny homes, storage, creative space, or future development. An active septic permit is already in

  Jamie Wylie Stratton Real Estate

  101 Catherine Rd, Jamaica, VT 05343
• 

  

  

  /20

  $99,500

  • Land
  • 10.27 Acres
  • $9,688 per Acre

  0 Theresa Ln, Wilmington, VT 05363

  This is a rare 10.27 acre offering located in the pastoral town of Wilmington, Vermont. Featuring approximately 8 acres open field, stone walls, cherry trees, potential views of the windmills with clearing, and the Beaver Brook running through the lower section, this property offers privacy and beauty. In addition, the land is close to Mount Snow and the Hermitage Club, plus provides easy access

  Lisa Mirando Deerfield Valley Real Estate

  0 Theresa Ln, Wilmington, VT 05363
• 

  /2

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

  Christine Lewis Brattleboro Area Realty

  109 Central St, Brattleboro, VT 05301
• 

  

  /24

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,475 Sq Ft

  166 Elliot St, Brattleboro, VT 05301

  This is a very cute 3-bedroom, 1 1/2 bathroom Cape, built in 1917. You'll appreciate the short distance on paved road to downtown Brattleboro. It's tucked in back of two Elliot St. houses. Propane-fired hot air furnace. The wood stove keeps the first floor very cozy. Lots of storage space, including the full basement. This is priced right to become your in-town home, so don't miss it. Showings

  John Hatton Berkley & Veller Greenwood Country

  166 Elliot St, Brattleboro, VT 05301
• 

  

  /54

  $3,750,000

  • 6 Beds
  • 6.5 Baths
  • 5,660 Sq Ft

  168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360

  Experience true mountain luxury in this stunning six bedroom six bathroom slope side single family home, perfectly positioned for effortless access to world-class skiing and snowboarding at the Stratton Mountain Resort. Designed with comfort and style in mind, this residence combines refined alpine architecture with modern amenities including a gym, steam shower, pool table that doubles as table

  Timothy Mich Doddridge Stratton Real Estate

  168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360
• 

  

  /29

  $739,999

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

  152 Main St, Grafton, VT 05146

  Newly renovated home located in the heart of Grafton Village! This home features 4 spacious bedrooms, and 2 full baths. Large primary bedroom suite located on the first floor of the home with working fireplace and private bathroom. Brand new kitchen with all new cabinetry, quartz countertops and stainless steel appliances. Original hardwood floors, moldings and original doors. All brand new

  Derek Greene Derek Greene

  152 Main St, Grafton, VT 05146
• 

  

  /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
• 

  

  /32

  $95,000

  • Land
  • 1 Acre
  • $95,000 per Acre

  169 Sun and Ski Rd, Wilmington, VT 05363

  Dreaming of building a home in Vermont but not sure where to start? With several significant steps in the preparation process already done, this one-acre lot is truly ready for your vision. A three-bedroom septic design by a Vermont engineer has been completed, with permits filed and approved by the state of Vermont. Plus, the land has already been partially cleared for a driveway and building

  Kim Meeker Southern Vermont Realty Group

  169 Sun and Ski Rd, Wilmington, VT 05363
• 

  

  /30

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  1089 Marlboro Rd, Brattleboro, VT 05301

  The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
• 

  

  /29

  $235,000

  • Land
  • 33.48 Acres
  • $7,019 per Acre

  0 Vt Route 100 Unit 5072614, Londonderry, VT 05155

  Beautiful 33.48 acre building lot in Londonderry. Some views possible and some clearing has been done. There are some wetlands on property but various choices for building sites exist. South East Facing

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  0 Vt Route 100 Unit 5072614, Londonderry, VT 05155
• 

  

  /20

  $475,000

  • Land
  • 136.9 Acres
  • $3,470 per Acre

  0 Taft Rd Unit 5064573, Townshend, VT 05353

  In the late 1790's, General Samuel Fletcher gave a large parcel of land to young Benjamin Murdock, whose father had died from smallpox while serving in the Revolutionary War. Benjamin built a cabin and then a house, cleared and plowed the land, and with his wife raised 8 children. That land is now known as Murdock Mountain. Entering the property is like stepping into the past. The deep stone

  Bill Hickok Berkley & Veller Greenwood Country

  0 Taft Rd Unit 5064573, Townshend, VT 05353
• 

  

  /54

  $1,499,000 Open Sat 2PM - 5PM

  • 4 Beds
  • 3.5 Baths
  • 3,666 Sq Ft

  3 Overbrook Dr Unit Outlook, Dover, VT 05356

  STUNNING NEW CONSTRUCTION, SPECTACULAR VIEWS, GREAT LOCATION! Set against the backdrop of Mount Snow, this just-completed luxury single-family home offers the perfect blend of modern design and spacious living. Located in the base area of the Mount Snow Resort, The OutLook at Mount Snow offers the perfect mix of mountain modern luxury and the ultimate convenience. This home features an open

  John Redd Skihome Realty

  3 Overbrook Dr Unit Outlook, Dover, VT 05356
• 

  

  /33

  $349,000

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  29 Pikes Falls Rd, Jamaica, VT 05343

  Experience the timeless appeal of this beautifully preserved 1800s Greek Revival residence in the center of Jamaica Village. Offering more than 2,500 square feet of living space, the home pairs classic architectural detail with thoughtful modern updates for effortless year-round living.Ideally situated just 15 minutes from Stratton Mountain and 25 minutes to Mount Snow, the location balances

  Carrie Mathews Winhall Real Estate

  29 Pikes Falls Rd, Jamaica, VT 05343
• 

  

  /60

  $798,000

  • 3 Beds
  • 3 Baths
  • 2,757 Sq Ft

  1909 Pine Banks Rd, Putney, VT 05346

  Sweetwood Farm circa 1894, this beautifully maintained extended Cape encompasses 60 serene acres of rolling meadows, shaded woodlands, and a peaceful, cascading brook. If you've been dreaming of a home that offers a convenient location, charm, and connection to the land, this is it. Inside, you'll find warm wide-pine floors, handcrafted cherry cabinets, and cozy living spaces filled with

  Heidi Bernier Berkley & Veller Greenwood Country

  1909 Pine Banks Rd, Putney, VT 05346
• 

  

  /20

  $400,000

  • 3 Beds
  • 2 Baths
  • 1,599 Sq Ft

  175 Sak Rd, Vernon, VT 05354

  This is it!!!! One level living with a bonus room and bath in the lower level for a bit of get away family room living. Perfect for downsizing or just beginning. Professional builder has taken this home to a brand new level, adding a living room with vaulted ceilings, wall of windows and a slider to a lovely back deck. The lot is level and sunny enough for a garden, and crosses the Sak Brook with

  Christine Lewis Brattleboro Area Realty

  175 Sak Rd, Vernon, VT 05354
• 

  

  /38

  $447,000

  • 3 Beds
  • 3 Baths
  • 1,768 Sq Ft

  52A Suntec Loop, Dover, VT 05356

  New and improved Suntec units, with brand NEW building exterior, windows, doors! Welcome to this beautifully maintained, bright & spacious 3 bedroom, 3 bath, plus loft townhome, offering the perfect blend of space, comfort, and convenience just minutes from Mount Snow’s main base lodge, Carinthia Lodge, and the Hermitage Club. This home features three large bedrooms with high ceilings, a

  Prema Fitzpatrick Real Broker LLC

  52A Suntec Loop, Dover, VT 05356
• 

  

  /58

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,772 Sq Ft

  7 Grassy Brook Rd, Brookline, VT 05345

  Incredible Opportunity! This fully renovated, move-in ready retreat is perfectly situated on the picturesque West River. Enjoy your own private beach and waterfront lifestyle at its finest. Whether you’re seeking a peaceful getaway, a year-round residence, or an investment property with proven short-term rental history, this home checks every box. Inside, the property has been thoughtfully

  Flex Realty Group Flex Realty

  7 Grassy Brook Rd, Brookline, VT 05345
• 

  

  /9

  $40,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  189 Shady Pines Park, Westminster, VT 05158

  1981 Skyline Homette mobile home in Shady Pines Park in Westminster. Very affordable approach to housing. Convenient to Rt. 91, Bellows Falls, Putney, Walpole, Brattleboro. Buyer will need to apply to Shady Park for approval. Property is being sold "as is".

  John Hatton Berkley & Veller Greenwood Country

  189 Shady Pines Park, Westminster, VT 05158
• 

  

  /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
• 

  

  /58

  $32,000

  • 1 Bed
  • 2 Baths
  • 771 Sq Ft

  123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356

  Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious mountain-side lockout unit, the closest unit to the back door to the slopes, comfortably sleeps 8. Unit 123 is a hotel room with 2

  Donna Brown Skihome Realty

  123/125 Qtr 4 Grand Summit Way Unit 123/125, Qtr 4, Dover, VT 05356
• 

  

  /54

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 4,040 Sq Ft

  17 Boulder Ridge Dr Unit A, Dover, VT 05356

  This magnificent 5-bedroom, 4.5-bath townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design. The living room, graced with hardwood (hickory) flooring, a gas fireplace, large windows, a slider to the deck with an amazing view of Mount Snow, and a vaulted ceiling, creates an ambiance

  John Redd Skihome Realty

  17 Boulder Ridge Dr Unit A, Dover, VT 05356
• 

  

  /34

  $539,000

  • 4 Beds
  • 3 Baths
  • 3,081 Sq Ft

  3996 Vermont 30, Jamaica, VT 05343

  Village charm meets mountain lifestyle in this beautifully updated home in the heart of Jamaica. Set above the road for added privacy, the property captures lovely winter views of the surrounding mountains and river while remaining just a short stroll to local shops and village conveniences.Inside, you’ll find generous living space with warm wood floors and a flowing, open layout designed for

  Carrie Mathews Winhall Real Estate

  3996 Vermont 30, Jamaica, VT 05343
• 

  

  /41

  $474,900

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  216 Ghastly Job Way, Wilmington, VT 05363

  Vermont mountain getaway perched on a private parcel at the end of a quiet country road, this charming mountain retreat offers sweeping long-range views spanning from the Green Mountains within the National Forest north to Mount Snow and east toward neighboring Marlboro. Enjoy breathtaking sunsets from the covered front porch or relax in the outdoor hot tub surrounded by nature. Inside, the

  Monique White Deerfield Valley Real Estate

  216 Ghastly Job Way, Wilmington, VT 05363
• 

  

  /29

  $25,000

  • Land
  • 0.6 Acre
  • $41,667 per Acre

  26 Upper Howes Way, Wilmington, VT 05363

  BUILD your dream home in this Lot in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse

  Sigrid Pickering Chimney Hill Realty

  26 Upper Howes Way, Wilmington, VT 05363
• 

  

  /27

  $33,900

  • 1 Bed
  • 2 Baths
  • 771 Sq Ft

  235/237, QTR 2 89 Grand Summit Way, Dover, VT 05356

  Own Where You Play! One-of-a-kind sleep eight quartershare, featuring a gas fireplace and gorgeous mountain views, this is a rare find in the Grand Summit Resort Hotel! This comfortable condo has two full baths and a lockout feature, with an adjoining door within the unit, so you can use it, rent it, or trade it for a timeshare vacation simultaneously! Overlooking the Grand Summit pool and the

  Patricia Fitzpatrick Skihome Realty

  235/237, QTR 2 89 Grand Summit Way, Dover, VT 05356
• 

  /2

  $249,000

  • Land
  • 1.29 Acres
  • $193,023 per Acre

  350 Route 100, Dover, VT 05356

  Amazing opportunity to have a building lot near Mount Snow with huge view potential, no HOA restrictions, and easy access off a main paved road. This unique site is being offered for the first time in a long time and could be the ideal spot to build your dream Vermont home.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  350 Route 100, Dover, VT 05356
• 

  

  /60

  $1,250,000

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

  732 Under the Mountain Rd, South Londonderry, VT 05155

  With 42+ stunning acres and unrivaled panoramic mountain (and sunset) views, this beautiful historic home seamlessly blends an extraordinary sense of history, grace, modern amenities, and will offer you the quintessential Vermont experience! Originally built in 1810 and artfully reimagined in 1987, the 5BR farmhouse features exposed beams, wide plank wood floors, and architectural character, and

  Claudia Harris Mary Mitchell Miller Real Estate

  732 Under the Mountain Rd, South Londonderry, VT 05155
• 

  

  /21

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,778 Sq Ft

  28 Summit Meadows Cir, Dover, VT 05356

  Lovely updated contemporary chalet nestled at the base of the Dover Hills in the village of Dover, just a short drive from the Mount Snow ski resort. This convenient location affords the privacy of a home, but much easier access, and proximity to amenities, dining, shopping, and more. At the end of a loop, this home sits on a private and quiet parcel with a nice buffer of trees, level lawn, stone

  Adam Palmiter Berkley & Veller Greenwood/Dover

  28 Summit Meadows Cir, Dover, VT 05356
• 

  

  /11

  $75,000

  • Land
  • 1.8 Acres
  • $41,667 per Acre

  L40 Boardman Loop, Wardsboro, VT 05360

  Nestled in the desirable Snow Mountain Farms West community, this 1.8-acre wooded lot offers the perfect setting to build your Vermont dream home or getaway. Gently sloping and bordered by the serene Wardsboro Brook (outside the FEMA flood zone), the property combines natural beauty with practical readiness. A state-issued wastewater permit for a 3 bedroom single family home and an individual

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  L40 Boardman Loop, Wardsboro, VT 05360
• 

  

  /49

  $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
• 

  

  /39

  $25,000

  • Land
  • 0.5 Acre
  • $50,000 per Acre

  30 Upper Howes Way, Wilmington, VT 05363

  Affordable Single Lot with favorable soil tests for a 3-bedroom single family home in Chimney Hill. Surrounded on two sides by common land, this lot is in a quiet section of the Main Hill. Buyer is responsible or securing a septic permit. Join a community of over 560 homes sited on 1,200-Acres adjoining the Green Mt. National Forest, with 550-Acres owned in common by the membership of the HOA.

  Sigrid Pickering Chimney Hill Realty

  30 Upper Howes Way, Wilmington, VT 05363
• 

  

  /31

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft

  8B Deer Creek, Dover, VT 05356

  Welcome to your dream home, nestled in the heart of the Mount Snow Valley. This charming 3-bedroom, 2-bath condominium offers a rare combination of value and convenience, making it the ideal retreat for families and adventurers alike.Prime Location: Situated just a short stroll from the exhilarating slopes of Mount Snow, you'll enjoy immediate access to two high-speed detachable 6-person

  Sheila Joyce-Albano Skihome Realty

  8B Deer Creek, Dover, VT 05356
• 

  

  /6

  $229,000

  • Land
  • 1.57 Acres
  • $145,860 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. Find

  Andrew King Stratton Real Estate

  2 Gold Medal Cir, Stratton, VT 05343
• 

  

  /5

  $270,000

  • 6 Beds
  • 2 Baths
  • 2,112 Sq Ft

  556 S Main St, Brattleboro, VT 05301

  What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit ofpressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

  Christine Lewis Brattleboro Area Realty

  556 S Main St, Brattleboro, VT 05301
• 

  

  /40

  $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
• 

  

  /16

  $259,900

  • Land
  • 29.2 Acres
  • $8,901 per Acre

  1270 Melendy Hill Rd, Guilford, VT 05301

  A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is

  Christine Lewis Brattleboro Area Realty

  1270 Melendy Hill Rd, Guilford, VT 05301
• 

  

  /45

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft

  4448 Route 100, Wardsboro, VT 05355

  This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always

  Julie Lowe Lowe's Real Estate, LLC

  4448 Route 100, Wardsboro, VT 05355

Showing Results 241 - 280, Page 7 of 10