439

Windham County VT Homes for Sale

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  • /55

    $329,000

    • 6 Beds
    • 2 Baths
    • 2,656 Sq Ft

    24 South St, Bellows Falls, VT 05101

    Unique in-village Victorian home offers so many possibilities: a large 6 bedroom home, as a primary with a large in-law suite, or as a duplex multifamily with possible 3rd or 4th rental units Both units on the 1st and 2nd floor feature high quality construction and finishes with many thoughtful touches. Both units are move in ready. Each floor has 3 bedrooms, newer quality kitchens, dining room,

    Steve Schoppmeyer BHG Masiello Brattleboro

    24 South St, Bellows Falls, VT 05101
  • /31

    $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
  • /28

    $285,000

    • 2 Beds
    • 1 Bath
    • 903 Sq Ft

    1555 W River Rd, Dummerston, VT 05301

    Open House 11/15 - 12pm-2pm Welcome home to this inviting 2-bedroom, 1-bath Cape on scenic West River Road. Perfectly located just a short drive to downtown Brattleboro’s shops, restaurants, and local conveniences—just over a quarter mile to West River Park and about 30 minutes to Mount Snow—this home offers the ideal blend of country charm and everyday comfort. Set on a beautiful .6-acre lot

    Morriah Adams BHG Masiello Brattleboro

    1555 W River Rd, Dummerston, VT 05301
  • /43

    $299,000

    • 6 Beds
    • 5 Baths
    • 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 Realty

    2072 N Main St, Londonderry, VT 05148
  • /32

    $295,000

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

    70 Overlook Dr, Londonderry, VT 05148

    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 but is modest and needs some updating. There are three bedrooms and 1.5

    Claudia Harris Mary Mitchell Miller Real Estate

    70 Overlook Dr, Londonderry, VT 05148
  • /8

    $52,000

    • Land
    • 6.1 Acres
    • $8,525 per Acre

    0 Cooke Rd, Brattleboro, VT 05301

    Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

    Victoria Woods Brattleboro Area Realty

    0 Cooke Rd, Brattleboro, VT 05301
  • /12

    $249,000

    • Land
    • 19.6 Acres
    • $12,704 per Acre

    227 Gault Rd, Wardsboro, VT 05355

    This property is ready for you to push the pedal down and Go. All the engineering work has been done! There is an inground 3 bedroom septic system, a drilled well and a long gravel driveway with culverts.With almost half of the 19 acres being cleared, there is massive solar potential here for off the grid living. There is a large shed/cabin at the beginning of the driveway, which you could

    Victoria Woods Brattleboro Area Realty

    227 Gault Rd, Wardsboro, VT 05355
  • /15

    $20,000

    • 1 Bath
    • 407 Sq Ft

    152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356

    Quarter share (deeded interval 3) ownership at the Grand Summit offers 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. Experience the mountain resort lifestyle affordably!! This first floor (Unit 152) with a sleep four studio is 407 sq ft and has a Murphy bed in the living area, a kitchen/dining area, and a full bath. This unit is located on

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356
  • /12

    $165,000

    • Land
    • 16.48 Acres
    • $10,012 per Acre

    1854 Vermont 9, Marlboro, VT 05344

    Escape to Nature – 16.48-Acre Glampsite with Cozy Cabins and Endless Potential Discover your private retreat on 16.48 serene wooded acres featuring two comfortably appointed sleeping cabins, each offering electricity, electric fireplaces for year-round comfort, and the possibility of internet. Enjoy modern convenience in a natural setting, with facilities for cooking and showering already onsite.

    Kristen Breeden Southern Vermont Realty Group

    1854 Vermont 9, Marlboro, VT 05344
  • /18

    $199,000

    • 2,139 Sq Ft

    34 Williams St, Bellows Falls, VT 05101

    Discover a superb investment or owner-occupant opportunity in the heart of downtown Bellows Falls, Vermont. This well-maintained two-story multi-family building offers two separate units, each featuring two bedrooms and one full bathroom. The property is dressed in durable vinyl siding for low-maintenance appeal and is fully insulated in the basement, exterior walls, and attic—enhancing energy

    Rob Weltz Barrett and Valley Associates Inc.

    34 Williams St, Bellows Falls, VT 05101
  • /18

    $65,000

    • 3 Beds
    • 1.5 Baths
    • 924 Sq Ft

    78 Shady Pines Park, Westminster, VT 05158

    Looking for an affordable place to call home? This could be the place for you! This 1989 Mobile Home currently sits on a large, rented lot in the conveniently located Shady Pines Park in Westminster VT, close to I-91, and many surrounding towns like Bellows Falls, Saxtons River, and Walpole. The home features a large eat-in kitchen, 3 bedrooms, one and a half bathrooms, and the addition of a

    Chelsea Richardson Barrett and Valley Associates Inc.

    78 Shady Pines Park, Westminster, VT 05158
  • /40

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,516 Sq Ft

    166 Taylor Ln, Whitingham, VT 05361

    Nestled in the scenic hills of Whitingham, this beautifully updated Vermont retreat offers the perfect blend of comfort, privacy, and breathtaking natural surroundings. Enjoy stunning views overlooking Lake Sadawga and the surrounding mountain landscape, creating a peaceful setting ideal for year-round living or a seasonal getaway. The home features new siding and a new roof, ensuring long-term

    Flex Realty Group Flex Realty

    166 Taylor Ln, Whitingham, VT 05361
  • /56

    $475,000

    • 3,954 Sq Ft

    430 Hucklehill Rd, Vernon, VT 05354

    NEW PRICE!! LOTS OF OPTIONS!! This quality built home can be enjoyed as spacious one floor living. There is a full finished walkout basement expanding your living space. A second full kitchen with granite counter tops, large family room, 3 bedrooms, bath, and laundry area, . Double doors open to a private patio, making this level ideal for an in-law suite, extended family, guests, or rental.

    Carol Slocum Keller Williams Realty Metro-Keene

    430 Hucklehill Rd, Vernon, VT 05354
  • /16

    $19,900

    • Land
    • 0.46 Acre
    • $43,261 per Acre

    00 Country Ct Unit 693, Wilmington, VT 05363

    Attention skiers, golfers, hikers, boaters, VAST lovers, and more! Discover the perfect blend of a country setting, amenities, and convenience with this exceptional land opportunity! This nearly half-acre lot is admirably located within Chimney Hill’s 1,200-acre private resort community with access to a wide range of recreational amenities for both summer and winter enjoyment. Located at the

    Casey Scott Southern Vermont Realty Group

    00 Country Ct Unit 693, 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 6 bedrooms and 3 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period details remain throughout,

    Jamie Watson BHG Masiello Keene

    88 Westminster St, Town of Rockingham, VT 05101
  • /33

    $390,000

    • 3 Beds
    • 1.5 Baths
    • 2,208 Sq Ft

    440 Stratton Arlington Rd, Stratton, VT 05360

    Experience the charm of owning a chalet in Vermont’s sought-after Stratton area, ideally located between Stratton Mountain and Mount Snow for easy ski access. Recent road improvements ensure smooth travel year-round. Outdoor lovers will enjoy nearby trails for hiking, snowmobiling, and snowshoeing, making this an ideal retreat for both relaxation and adventure. The home features a finished

    Mike England Michael England Real Estate

    440 Stratton Arlington Rd, Stratton, VT 05360
  • /22

    $365,000

    • 4 Beds
    • 2 Baths
    • 1,742 Sq Ft

    801 Newton Rd, Vernon, VT 05354

    Charming renovated split level chalet located conveniently in the heart of Vernon. This lovely spot has a large yard space with ample privacy, and easy nearby access to the Vernon community park. Inside you are treated to a vaulted great room with exposed beams and brick hearth for wood stove, with great natural light. There is a new kitchen with the same vaulted ceilings and slider out to the

    Adam Palmiter Berkley & Veller Greenwood/Dover

    801 Newton Rd, Vernon, VT 05354
  • /34

    $365,000

    • 1 Bed
    • 1 Bath
    • 861 Sq Ft

    12 Cross St, Newfane, VT 05345

    Can you imagine...the cutest cottage, on an acre of open, rolling meadow in the center of one of the area's most photographed towns.....and....just big enough to be perfect...the kitchen is large enough for more than just one cook, so you can share the joy! There is a ton of counter top and much needed storage. The center island helps divide up the tasks! Decorate the sweet fireplace mantle for

    Christine Lewis Brattleboro Area Realty

    12 Cross St, Newfane, VT 05345
  • /21

    $249,000

    • Land
    • 48.5 Acres
    • $5,134 per Acre

    590 Howard Hill Rd, Landgrove, VT 05148

    Discover the perfect blend of privacy, recreation, and natural beauty with this exceptional 48+ acre parcel located in the desirable Powder Mill development. Set at the end of a quiet, dead-end road, this property offers peace and seclusion while being part of a community known for its extensive network of trails, ideal for year-round enjoyment — hike, cross-country ski, snowshoe, or snowmobile

    Carrie Mathews Winhall Real Estate

    590 Howard Hill Rd, Landgrove, VT 05148
  • /23

    $500,000

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft

    137 Pleasant Valley Rd, Brattleboro, VT 05301

    This is IT! If you are looking for an incredible small home...not tiny...but compact and just the right size, this is it. Timber framing at it's best gives you an open concept, live in every inch, light filled, high quality charming home. Nestled in a wildflower meadow, with plenty of room for a homestead garden, enough open sky for stargazers, big and flat enough for your own cross country ski

    Christine Lewis Brattleboro Area Realty

    137 Pleasant Valley Rd, Brattleboro, VT 05301
  • /12

    $39,999

    • Land
    • 2 Acres
    • $20,000 per Acre

    14 Brickyard Rd, Dover, VT 05341

    Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy. From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

    David White OwnerEntry.com

    14 Brickyard Rd, Dover, VT 05341
  • /19

    $190,000

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft

    39 Brookside Dr Unit 3, Brattleboro, VT 05301

    Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the woods and a small yard space. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement for extra storage with washer/dryer hookup. The entire interior has been freshly painted, new kitchen cabinets, countertop, new flooring, new bathroom

    Angela Sherman Brattleboro Area Realty

    39 Brookside Dr Unit 3, Brattleboro, VT 05301
  • /24

    $29,900

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft

    97 Glen St, Brattleboro, VT 05301

    Finally!! Affordable!! This just right sized home is tucked into the 55 and older park for peace and quiet. Along the brook, the damaged homes have been removed and replaced with open green space with a gentle park like feel. There is an awning over the stairs, an added pitched roof, spacious front end kitchen/dining with several windows and some built-ins. Located in one of the 3 parks, making

    Angela Sherman Brattleboro Area Realty

    97 Glen St, Brattleboro, VT 05301
  • /44

    $429,900

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft

    1909 Davidson Hill Rd, Westminster, VT 05158

    This charming Vermont country farmhouse offers peaceful privacy at the end of a quiet town road. Recently updated with quality materials and meticulous attention to detail, the home blends classic warmth with modern comfort. The open-concept main floor features a beautifully appointed kitchen ideal for family meals, flowing into the dining area and a cozy living room with a bay window and

    Steve Schoppmeyer BHG Masiello Brattleboro

    1909 Davidson Hill Rd, Westminster, VT 05158
  • /11

    $85,000

    • Land
    • 3 Acres
    • $28,333 per Acre

    1154 Vermont 8a, Whitingham, VT 05361

    3 Acres in picturesque Jacksonville Vermont – Here’s a great opportunity to create your Vermont getaway or forever home. This beautiful 3-acre lot offers a perfect mix of open space and natural scenery — ideal for outdoor enthusiasts. Enjoy nearby VAST snowmobile trails, fishing, hiking, and you're just 25 minutes from Mount Snow for skiing and year-round recreation.A mobile home once

    Kerry Mulverhill

    1154 Vermont 8a, Whitingham, VT 05361
  • /41

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    25 Upper Handle Rd Unit A, Dover, VT 05356

    Welcome to this inviting 3-bedroom plus loft, 2-bath Apple Hill condominium—perfectly located just minutes from Mount Snow. This spacious and well-maintained home offers a comfortable layout for a relaxing Vermont getaway. The updated kitchen and dining area feature a charming window seat, while the open-concept living room boasts another cozy window seat and a wood-burning fireplace for those

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    25 Upper Handle Rd Unit A, Dover, VT 05356
  • /3

    $500,000

    • Land
    • 5.05 Acres
    • $99,010 per Acre

    Lot 1 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 5+ acres overlooking the 18th hole and mountains beyond for year

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 1 Mountain Ridge Estates, Wilmington, VT 05363
  • /3

    $450,000

    • Land
    • 3.38 Acres
    • $133,136 per Acre

    Lot 4 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 3.38+ acres overlooking the 18th tee box and mountains beyond for

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 4 Mountain Ridge Estates, Wilmington, VT 05363
  • /3

    $500,000

    • Land
    • 1.1 Acres
    • $454,545 per Acre

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.1 acres overlooking the fairway of the 18th hole and mountains

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
  • /3

    $500,000

    • Land
    • 1.82 Acres
    • $274,725 per Acre

    Lot 3 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.82+ acres overlooking the 18th fairway and mountains beyond for

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 3 Mountain Ridge Estates, Wilmington, VT 05363
  • /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
  • /9

    $185,000

    • Land
    • 8 Acres
    • $23,125 per Acre

    4441 Vermont 30, Jamaica, VT 05343

    Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

    Helen Nault

    4441 Vermont 30, Jamaica, VT 05343
  • /44

    $485,000

    • 3 Beds
    • 2 Baths
    • 1,751 Sq Ft

    2418 Vermont 11, Londonderry, VT 05148

    Discover this truly one-of-a-kind property in the heart of Londonderry, Vermont — a stunningly renovated former church that perfectly blends historic charm with modern elegance. This unique three-bedroom, two-bathroom home offers an expansive open-concept living space filled with natural light, showcasing soaring ceilings and gorgeous finishes throughout. The kitchen is a showstopper, featuring

    Noel Weeks Welcome Home Real Estate

    2418 Vermont 11, Londonderry, VT 05148
  • /52

    $1,150,000

    • 8 Beds
    • 4 Baths
    • 4,828 Sq Ft

    5 Tannery Rd, West Dover, VT 05356

    Discover your getaway at Mount Snow in this beautifully renovated 8-bedroom estate, ideal for unforgettable family gatherings, cherished reunions, or inspiring work retreats. Set on nearly 4 serene acres at the foot of Mount Snow, you'll be surrounded by breathtaking mountain views and enjoy effortless access to the slopes just a short drive away. This magnificent home features a dedicated

    Michelle O'Neil Deerfield Valley Real Estate

    5 Tannery Rd, West Dover, VT 05356
  • /26

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    106 Silver Birch Unit 17H, Dover, VT 05356

    Bright 3-Bedroom End Unit at Timber Creek – Across from Mount Snow Ski Area.Welcome to your mountain getaway! This sunny 3-bedroom, 2-bath end unit in the desirable Timber Creek condominium community offers the perfect blend of comfort, convenience, and year-round recreation. Located directly across from Mount Snow and a short drive to the Hermitage Club, you'll enjoy unbeatable access to

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    106 Silver Birch Unit 17H, Dover, VT 05356
  • /38

    $1,600,000

    • 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
  • /29

    $199,000

    • Land
    • 4 Acres
    • $49,750 per Acre

    385 Chester Hill Rd, Grafton, VT 05146

    Rare opportunity to own acreage near edge of Grafton Village Vermont! This 4 acre parcel is offered for the first time in over 50 years! It truly is Grafton's best kept secret, driving by you would never know this opportunity exists. A rectangular lot on a paved town-maintained road with a driveway roughed into the center of the lot where you'll find a lovely pond and rustic cabin now ready to

    Jessica Landers Barrett and Valley Associates Inc.

    385 Chester Hill Rd, Grafton, VT 05146
  • /35

    $139,000

    • 4 Beds
    • 2 Baths
    • 1,910 Sq Ft

    2197 N Main St, Londonderry, VT 05148

    Charming 1860 Village Home with Character and Potential – Sold As Is.Step back in time with this 1860 village home offering space, character, and opportunity. Located right on the main road in a busy village setting, this 4-bedroom, 2-bath home provides a traditional layout with all bedrooms on the upper level and multiple gathering spaces on the first floor. Inside, you’ll find a

    Lee Brown Four Seasons Sotheby's Int'l Realty

    2197 N Main St, Londonderry, VT 05148
  • /48

    $27,900

    • 1 Bed
    • 2 Baths
    • 941 Sq Ft

    230, Qtr 2 Grand Summit Way Unit 230, Qtr 2, 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 very spacious valley-side unit is the closest unit to the owner's library and lounge, and comfortably sleeps 6. This is a 1-level, 1-bedroom unit

    Donna Brown Skihome Realty

    230, Qtr 2 Grand Summit Way Unit 230, Qtr 2, Dover, VT 05356
  • /14

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft

    8 Happy Haven Rd, Wilmington, VT 05363

    Conveniently located to village center, elementary school, lakes and trails. This riverfront home is waiting for a facelift! Three bedrooms, 2 bathrooms, living room, kitchen with a dining area with siders to a deck over looking the Deerfield River. Room downstairs for a hobby or craft room and a family room with a gas fireplace. Newer hot water tank and furnace. Room for gardens and a two car

    Janet Boyd Boyd Real Estate

    8 Happy Haven Rd, Wilmington, VT 05363

Showing Results 41 - 80, Page 2 of 11

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