36

Modern & Contemporary Homes for Sale in Windham County VT

Section Image Section Image
  • /31

    $359,000

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

    410 Tallwood Cir, Londonderry, VT 05148

    This cute Sherwood Forest house is ready for the next owners! Nicely renovated over the past several years, this 3 bedroom, 1 and a half bath chalet is located in the heart of Vermont ski country. In between Londonderry and Bromley, minutes from Manchester or Stratton and Magic ,this central location allows for access to all that makes Vermont special! Enjoy the open living area after a day of

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 392-0721

    410 Tallwood Cir, Londonderry, VT 05148
  • /37

    $489,000

    • 2 Beds
    • 2 Baths
    • 1,194 Sq Ft

    4 Sportscenter Village Way Unit B33, West Dover, VT 05356

    Meticulously maintained and updated, rare to come on the market, top-floor 2-bedroom, 2-bath condo located in the Seasons on Mount Snow trailside community! A two-level unit featuring a primary ensuite on the main level and a bedroom with an ensuite on the second level. Newer appliances, granite kitchen counters, a tastefully renovated primary ensuite bathroom, and plush carpeting are some of the

    Patricia Fitzpatrick Skihome Realty

    4 Sportscenter Village Way Unit B33, West Dover, VT 05356
  • /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
  • /51

    $899,800

    • 5 Beds
    • 8 Baths
    • 7,430 Sq Ft

    925 Hinesburg Rd, Brattleboro, VT 05301

    Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

    Christine Lewis Brattleboro Area Realty

    925 Hinesburg Rd, Brattleboro, VT 05301
  • /37

    $795,000

    • 4 Beds
    • 4 Baths
    • 3,600 Sq Ft

    5 Hillwinds N, Brattleboro, VT 05301

    Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through

    Robert Doyle Berkley & Veller Greenwood Country

    5 Hillwinds N, Brattleboro, VT 05301
  • /27

    $445,000

    • 2 Beds
    • 2 Baths
    • 1,353 Sq Ft

    49 High Point Dr Unit A-14, Stratton, VT 05360

    Embrace the ultimate Stratton lifestyle in this turnkey, one-level 2BR/2BA condo designed for effortless mountain access. Located just moments from the Village and the Stratton training center, this home eliminates the logistics and maximizes the fun with a dedicated gear-ready mudroom and a complimentary shuttle that whisks you straight to the lifts. The interior features a bright, open-concept

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    49 High Point Dr Unit A-14, Stratton, VT 05360
  • /38

    $749,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    717 Horsenail Hill Rd, Chester, VT 05143

    Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

    Robin Apps Four Seasons Sotheby's Int'l Realty

    717 Horsenail Hill Rd, Chester, VT 05143
  • /51

    $915,000

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

    33 Carinthia Rd, Dover, VT 05356

    LOCATION, LOCATION, LOCATION!! 3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces, and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood-burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral

    Jacki Murano Southern Vermont Realty Group

    33 Carinthia Rd, Dover, VT 05356
  • /49

    $699,900

    • 3 Beds
    • 2 Baths
    • 2,450 Sq Ft

    300 Route 121 E, Grafton, VT 05146

    Nestled in a postcard-perfect setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Set on over two park-like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle.Inside, you’ll find a spacious eat-in kitchen with abundant counter space and

    Gary Coger Four Seasons Sotheby's Int'l Realty

    300 Route 121 E, Grafton, VT 05146
  • /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
  • /16

    $1,400,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,844 Sq Ft

    286 Coldbrook Rd, Wilmington, VT 05363

    This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf

    Melissa Nebelski Real Broker LLC

    286 Coldbrook Rd, Wilmington, VT 05363
  • /25

    $369,000

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

    36C N Access Rd Unit 703, Dover, VT 05356

    Spacious Snow Mountain Village townhome adjacent to the upper parking lots at Mount Snow ski resort. This unique large unit is one of only a handful of units with this size for the development. Inside you are greeted by a tiled mudroom area with laundry, and an adjacent large guest room with en suite full bath. The main level has a large open concept living room with wood burning fireplace and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    36C N Access Rd Unit 703, Dover, VT 05356
  • /48

    $394,000

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    9F Brumms Way Unit 9F, Dover, VT 05356

    Beautiful end unit on edge of Bear’s Crossing Condo and Home Community with a stream and the forest as your neighbor. Close to the Ski Home trail. This mixed community is 2 minutes to Mount Snow Ski Resort and to mixed use trails for snowmobiling, xcountry skiing and mountain biking. There is also a shuttle running regularly to the resort and beyond! This unit is “turn key” with 2 bedrooms and a

    Steve Goldfarb Deerfield Valley Real Estate

    9F Brumms Way Unit 9F, Dover, VT 05356
  • /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
  • /43

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    1 Lower Highlands Rd, West Dover, VT 05356

    Custom-built 4-bedroom, 2.5-bath home ideally located less than a mile from Mount Snow. The main level welcomes you with an inviting foyer off the covered front porch and offers a well-designed layout featuring a spacious living room, formal dining room, comfortable family room, versatile den, and a well-appointed kitchen. Additional conveniences include a half bath, dedicated laundry area, and a

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1 Lower Highlands Rd, West Dover, VT 05356
  • /20

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 1,800 Sq Ft

    56 Shattarack Rd Unit D6, Stratton, VT 05360

    Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

    Kim Morgan-Wohler Wohler Realty Group

    56 Shattarack Rd Unit D6, Stratton, VT 05360
  • /58

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    1192 Chapel Hill Rd, Whitingham, VT 05361

    Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level,

    Cliff Leinonen Four Seasons Sotheby's Int'l Realty

    1192 Chapel Hill Rd, Whitingham, VT 05361
  • /2

    $174,900

    • 2 Beds
    • 2,710 Sq Ft

    29 Stable Rd, Wilmington, VT 05363

    The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area, The Golf Course and The Hermitage Club close to the Coldbrook. Built as a post and beam home. Features 4 plus acres with ample parking. Building will need an extensive rehab. Not safe to go into the structure.

    Mark Yule BHG Masiello Brattleboro

    29 Stable Rd, Wilmington, VT 05363
  • /32

    $595,000

    • 5 Beds
    • 2 Baths
    • 2,892 Sq Ft

    238 Hemlock Hill Rd, Wardsboro, VT 05355

    This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The Property has a brand new roof!!! The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails across the street. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for aprés ski gatherings, and the

    Jeffrey Sheehan Cummings & Co

    238 Hemlock Hill Rd, Wardsboro, VT 05355
  • /26

    $899,000

    • 3 Beds
    • 3.5 Baths
    • 1,730 Sq Ft

    1C Townhouse Square Unit 7, Dover, VT 05356

    Experience true ski-in/ski-out living at Mount Snow in the highly desirable Seasons on Mount Snow community - on Tin Lizzy, and just seconds to the lift. This spacious 3-bedroom, 3.5-bath townhouse offers a thoughtful and functional layout, including two private en suite bedrooms for added comfort and flexibility. Two separate living areas provide ample space for entertaining and relaxing, while

    Stephanie Sugden Real Broker LLC

    1C Townhouse Square Unit 7, Dover, VT 05356
  • /19

    $249,000

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155

    Close to Magic, Bromley and Stratton! This two-bedroom, one bath condo with woodburning fireplace overlooks a beautiful brook and tennis court area. Private deck out back to enjoy some sun. Eat in kitchen with pass through countertop area opens into the living room. Manageable and spacious for a nice weekend getaway or make this your fulltime home. Just minutes to downtown with shopping, fuel,

    Julie Lowe Lowe's Real Estate, LLC

    3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155
  • /19

    $349,000

    • 2 Beds
    • 2 Baths
    • 1,035 Sq Ft

    32B Snow Tree Ln Unit Oaks B, Dover, VT 05356

    Owner open to offers. This nicely updated two bedroom, two bath Snowtree unit is located at the base of the Mount Snow ski resort. There is shuttle service to and from the mountain, easy access by way of a foot bridge through the community, and the unit looks west with views of gorgeous sunsets, down the valley, and winter views of the slopes of the mountain, so that you can check the conditions

    Adam Palmiter Berkley & Veller Greenwood/Dover

    32B Snow Tree Ln Unit Oaks B, Dover, VT 05356
  • /52

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 2,814 Sq Ft

    195 Mann Rd Unit 12, Wilmington, VT 05363

    Beautifully positioned along the 11th fairway of the Haystack Golf Course, this contemporary 3-bedroom, 4-bath townhouse offers four-season comfort with gorgeous mountain and sunrise views. The bright main level features an open layout with vaulted ceilings, a wood-burning fireplace, contemporary kitchen with breakfast bar, and a spacious dining area overlooking the outdoors. The primary suite is

    Donald Koelsch Deerfield Valley Real Estate

    195 Mann Rd Unit 12, Wilmington, VT 05363
  • /43

    $2,000,000

    • 6 Beds
    • 4.5 Baths
    • 4,950 Sq Ft

    43 Upton Rd, Dover, VT 05356

    The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end

    Adam Palmiter Berkley & Veller Greenwood/Dover

    43 Upton Rd, Dover, VT 05356
  • /36

    $269,000

    • 1 Bed
    • 1 Bath
    • 2,000 Sq Ft

    116 Birge St Unit 3, Brattleboro, VT 05301

    Huge price reduction! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings,

    Liz LaVorgna Brattleboro Area Realty

    116 Birge St Unit 3, Brattleboro, VT 05301
  • /41

    $539,000

    • 4 Beds
    • 3 Baths
    • 2,948 Sq Ft

    196 Powder Mill Rd, Londonderry, VT 05148

    Mountain Escape with Multi-Generational Potential in Powder Mill Welcome to your mountain retreat in the heart of Vermont’s ski country! This spacious home in the desirable Powder Mill community has been thoughtfully updated with brand new kitchen cabinets, gleaming granite countertops, stainless steel appliances, and fresh carpet and flooring throughout. The flexible layout offers room for

    Katie Ladue Gilbert BHHS Verani Upper Valley

    196 Powder Mill Rd, Londonderry, VT 05148
  • /59

    $2,398,000

    • 4 Beds
    • 4 Baths
    • 3,585 Sq Ft

    127 Fannie Hill Dr, Wilmington, VT 05363

    Welcome to 127 Fannie Hill Road, an exceptional mountain retreat ideally located adjacent to The Hermitage Club in Wilmington, Vermont. This stunning 4 bedroom, (with two bonus bunk rooms) 4 bathroom home artfully blends modern mountain living with rustic charm. Featuring a thoughtful mix of materials which include reclaimed barn board, sleek corrugated metal, and contemporary cable railing this

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    127 Fannie Hill Dr, Wilmington, VT 05363
  • /26

    $579,000

    • 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
  • /45

    $437,000

    • 4 Beds
    • 3.5 Baths
    • 2,015 Sq Ft

    29 First Unit 17, Wilmington, VT 05363

    Enjoy Green Mountain views from this bright and spacious end-unit townhouse, perfectly sited on the 1st fairway at the Haystack Golf Course. An oversized deck invites outdoor dining and entertaining, with sunsets over Haystack Mountain as your backdrop. Inside, natural light pours through windows and skylights into the open floor plan featuring vaulted ceilings, a fieldstone wood-burning

    Monique White Deerfield Valley Real Estate

    29 First Unit 17, Wilmington, VT 05363
  • /54

    $1,499,000

    • 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
  • /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
  • /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
  • /35

    $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
  • /39

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,957 Sq Ft

    256 Potter Rd, Wardsboro, VT 05355

    Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    256 Potter Rd, Wardsboro, VT 05355
  • /37

    $939,000

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

    25 Boulder Ridge Dr Unit B, Dover, VT 05356

    This magnificent 4-bedroom, 4-bathroom townhouse, spanning over three tastefully designed floors, will captivate you with its elegance. The open floor plan combines contemporary aesthetics with practical design, offering a living experience par excellence. This townhouse was finished in 2021 and has the “new construction” feel. The living room, graced with hardwood flooring, a gas fireplace,

    John Redd Skihome Realty

    25 Boulder Ridge Dr Unit B, Dover, VT 05356
  • /33

    $229,000

    • 1 Bath
    • 475 Sq Ft

    11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356

    Discover effortless mountain living in this beautifully updated studio condominium that is walking distance to the slopes and in the desirable Snow Tree community. Perfect for weekend getaways, seasonal escapes, or as a high performing rental investment. This home boasts an extremely strong rental history supported by a documented 3 year history of over $25,000 annually and is being offered fully

    Melissa Ellis Southern Vermont Realty Group

    11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356
How to Buy a Home How to Finance a Home How to Sell a Home