Windham County VT Houses for Sale

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  /34

  $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

  

  Alison Cummings

  Cummings & Co

  (802) 392-0721

  410 Tallwood Cir, Londonderry, VT 05148
• 

  

  

  /60

  $674,950

  • 3 Beds
  • 2.5 Baths
  • 2,386 Sq Ft

  56 Whitetail Dr, Vernon, VT 05354

  Properties of this scale and setting are a rare find. Designed with entertaining in mind, the home’s circulation flows effortlessly through a dramatic great room anchored by a striking two-story fireplace. The space opens seamlessly to the dining and kitchen areas and is framed by a wall of windows that lead to an expansive deck overlooking a tranquil pond. A statement staircase ascends to a

  

  Mathew Ghafoori

  RE/Max Heritage

  (802) 278-9432

  56 Whitetail Dr, Vernon, VT 05354
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  /60

  $4,950,000

  • 4 Beds
  • 8 Baths
  • 16,736 Sq Ft

  1950 Collins Rd, Brattleboro, VT 05301

  Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

  

  Margretta Fischer

  Wohler Realty Group

  (802) 317-7158

  1950 Collins Rd, Brattleboro, VT 05301
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  /60

  $849,000

  • 5 Beds
  • 4.5 Baths
  • 3,840 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

  MaryKate Grey Stratton Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
• 

  

  

  /35

  $2,399,000

  • 4 Beds
  • 4.5 Baths
  • 3,569 Sq Ft

  662 Howe Farm Rd, Jamaica, VT 05343

  Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  662 Howe Farm Rd, Jamaica, VT 05343
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  /26

  $325,000

  • 2 Beds
  • 2 Baths
  • 976 Sq Ft

  9047 Vermont 30, Jamaica, VT 05155

  “The Yellow Sweetie” offers a rare blend of charm, convenience, and proven income potential. This stylish country-meets-shabby-chic retreat has been a high-income producing rental for many years, making it an excellent opportunity for investment, year-round living, or a Vermont vacation retreat.Ideally located near the base of Stratton Mountain, the property sits just one minute from the

  Carrie Mathews Winhall Real Estate

  9047 Vermont 30, Jamaica, VT 05155
• 

  

  /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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  /41

  $495,000

  • 4 Beds
  • 2.5 Baths
  • 2,756 Sq Ft

  214 Putney Rd, Brattleboro, VT 05301

  Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  214 Putney Rd, Brattleboro, VT 05301
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  /40

  $214,900

  • 5 Beds
  • 3.5 Baths
  • 3,600 Sq Ft

  2139 Vt Route 30, Townshend, VT 05353

  Great days ahead for the buyer of this stately, manor styled home on close to three (3) acres. You have to see the interior to believe it. Dated? Yes, but solid bones. Crazy nice wood floors, classic built-ins & style. So many 'nooks & crannies. Cavernous, dry & clean basement. Exterior: 'challenged', but I have all the bids to bring it to 'good' condition & the techies are ready to complete

  Robert Balewicz Evergreen Realty of Vermont

  2139 Vt Route 30, Townshend, VT 05353
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  /51

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Exceptional property tucked amidst nature with views toward Magic. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or looking for a year round residence with great schools, this property offers an optimal location- convenient to Stratton, Bromley and Magic Mountains as well as Burr and Burton Academy and Floodbrook School. Gourmet kitchen with gas

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
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  /27

  $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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  /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
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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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  /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
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  /54

  $2,050,000

  • 4 Beds
  • 4.5 Baths
  • 2,486 Sq Ft

  97 N Brookwood Rd, Stratton, VT 05360

  Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk room with attached bathroom. Gorgeous great room with stone

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  97 N Brookwood Rd, Stratton, VT 05360
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  /29

  $625,000

  • 5 Beds
  • 2 Baths
  • 2,774 Sq Ft

  618 Shearer Hill Rd, Brattleboro, VT 05301

  Discover the Best of Southern Vermont Living! Nestled in a bucolic country setting, this versatile property offers breathtaking views of a neighboring classic Sugar House and a large beaver pond that is the headwaters of the Green River. Whether you're seeking a serene country retreat, a dedicated ski house, or a comfortable year-round home, this classic cape checks all the boxes. The bright,

  Thomas Dahlin Berkley & Veller Greenwood Country

  618 Shearer Hill Rd, Brattleboro, VT 05301
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  /24

  $399,000

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

  4850 Vermont Route 100, Wardsboro, VT 05355

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

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4850 Vermont Route 100, Wardsboro, VT 05355
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  /32

  $949,000 New Construction

  • 3 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  49 Joan's Ridge Rd, Dover, VT 05356

  Gorgeous new construction home just completed and ready for immediate use this season. This lovely home looks out to the ski trails at Mount Snow yet is in the heart of Dover with very easy access off a paved road. The interior features gorgeous natural light and exposed natural woodwork throughout, 3/4 inch solid red oak flooring, oversized windows, a bright living area with gas fireplace off

  Adam Palmiter Berkley & Veller Greenwood/Dover

  49 Joan's Ridge Rd, Dover, VT 05356
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  /40

  $3,050,000

  • 6 Beds
  • 3 Baths
  • 3,309 Sq Ft

  36 Woffenden Rd, Wilmington, VT 05363

  Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and

  Melissa Ellis Southern Vermont Realty Group

  36 Woffenden Rd, Wilmington, VT 05363
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  /26

  $629,000

  • 3 Beds
  • 3 Baths
  • 2,170 Sq Ft

  14 Johnson Hill Rd, Dover, VT 05356

  Unique contemporary chalet just a short drive from the Mount Snow Ski Resort and village Wilmington, and with direct snowmobile trail access. This very cool open concept home has been completely renovated and upgraded, and sits on a on a private lot in the Dover Hills with beautiful lawn space and cul de sac driveway. Walk in through the spacious mudroom with plenty of room for gear, and head up

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14 Johnson Hill Rd, Dover, VT 05356
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  /35

  $899,900

  • 4 Beds
  • 3.5 Baths
  • 2,272 Sq Ft

  12 Encore Place, Dover, VT 05356

  Mountain Modern Living with unmatched ski views of Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of Carinthia. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the alpine landscape.

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  12 Encore Place, Dover, VT 05356
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  /41

  $539,000

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

  196 Powder Mill Rd, Londonderry, VT 05148

  Falling Leaves and PRICES! Buy now before the ski season begins!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

  Katie Ladue Gilbert KW Vermont Woodstock

  196 Powder Mill Rd, Londonderry, VT 05148
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  /2

  $199,000

  • 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 and Golf Course and The Hermitage Club close to the Coldbrook. Built to sleep 32 People. 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
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  /37

  $730,000

  • 5 Beds
  • 3 Baths
  • 2,635 Sq Ft

  341 Under the Mountain Rd, Londonderry, VT 05148

  Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

  Andy Reed Four Seasons Sotheby's Int'l Realty

  341 Under the Mountain Rd, Londonderry, VT 05148
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  /29

  $449,000

  • 4 Beds
  • 1 Bath
  • 1,730 Sq Ft

  83 Depot St, Jamaica, VT 05343

  Step back in time while enjoying modern comforts in this lovingly restored 1800s riverfront farmhouse with attached barn, set in the heart of Southern Vermont. Rich with historic character, the home features original wide pine floors, plaster walls, a slate roof, and classic architectural lines that reflect Vermont’s timeless heritage.The private backyard borders the West River, offering a

  Carrie Mathews Winhall Real Estate

  83 Depot St, Jamaica, VT 05343
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  /54

  $705,000

  • 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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  /60

  $650,000

  • 4 Beds
  • 4 Baths
  • 2,978 Sq Ft

  23 Brook Rd, Saxtons River, VT 05154

  Includes 1-Year Home Warranty. A Distinctive Country Retreat on 6.8± private acres in the heart of the historic village of Saxtons River. This idyllic country estate offers year-round views, exquisite perennial gardens, & two beautifully integrated wings—the timeless Cape & the charming Carriage House. Inside of the Cape wing is a sunlit eat-in kitchen, KraftMaid cherry cabinetry & Silestone

  Isabella Luhrs BHG Masiello Keene

  23 Brook Rd, Saxtons River, VT 05154
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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
• 

  

  /17

  $459,000

  • 5 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  46 Town Farm Rd, Wilmington, VT 05363

  3 Story home with 1 car attached garage....new vinyl siding, windows and roofing installed in 2021 along with exterior foamboard insulation.FIRST FLOOR- Open concept entirely remodeled in 2022; mudroom, kitchen, 1/2 bath, and family/dining room. Vinyl plank flooring throughout, white shiplap walls and natural tongue & groove ceilings. Vermont castings wood burning stove.SECOND

  David White OwnerEntry.com

  46 Town Farm Rd, Wilmington, VT 05363
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  /39

  $869,000

  • 5 Beds
  • 3.5 Baths
  • 4,626 Sq Ft

  6 Brumms Way, Dover, VT 05356

  Located directly across from the ski-home trail in Bears Crossing, this 2011-built home offers unbeatable access. Designed with quality and function in mind, this lodge-style retreat blends rustic charm with thoughtful modern comfort. The lot provides exceptional convenience to Mount Snow via the ski-home trail and direct shuttle service to and from the base area. Ski from the trail right to the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  6 Brumms Way, Dover, VT 05356
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  /37

  $289,000

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  2378 Deer Park Rd, West Halifax, VT 05358

  Set back from the road, this charming rustic cabin on 10 acres is the perfect retreat for those seeking tranquility. Enter a warm, inviting open layout with a cozy wood stove. One-level living also includes two generous bedrooms and a full bath. You have spacious front and back decks to look out onto your acres of woods. Follow a trail up to a unique, spectacular glass treehouse that is calming

  Kristen Ziter Taylor Brattleboro Area Realty

  2378 Deer Park Rd, West Halifax, VT 05358
• 

  

  /23

  $489,000

  • 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
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  /32

  $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
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  /46

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,960 Sq Ft

  16 Springhill Rd, Dover, VT 05356

  Experience modern luxury in this stunning contemporary home, less than 10 minutes from Mount Snow and just 15 minutes from The Hermitage Club. This thoughtfully designed retreat offers both sophistication and comfort, with high-end finishes and exceptional craftsmanship throughout. You will be captivated by the soaring freestanding stone fireplace, which serves as the heart of the home, complete

  Patrice Schneider Southern Vermont Realty Group

  16 Springhill Rd, Dover, VT 05356
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  /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
• 

  

  /50

  $415,000

  • 3 Beds
  • 1 Bath
  • 701 Sq Ft

  3034 Route 11, Londonderry, VT 05148

  Are you a large business owner looking for housing for employees, an investor looking for a great opportunity, a landlord looking for more rental units, or are you looking for a ski home with rental income to make it more affordable, or looking for a property to make your home with existing rental income to help make that dream a reality? Look no further than this unique property with endless

  Erin Kendall EXP Realty

  3034 Route 11, Londonderry, VT 05148
• 

  

  /43

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 2,872 Sq Ft

  1587 Upper Holbrook Rd, Whitingham, VT 05361

  Set on 3 beautiful acres, this well-maintained 3-bedroom plus loft, 2 1/2 bath home is truly move-in ready. Enter through a spacious mudroom with a convenient back opening for bringing in firewood for the cozy wood stove in the living room. The open-concept kitchen and dining area provide plenty of room for entertaining, while a den/game room just off the living room with a bar area (4X8) offers

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1587 Upper Holbrook Rd, Whitingham, VT 05361
• 

  

  /58

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  136 Yeaw Rd, Dover, VT 05341

  Tranquil Vermont living with exceptional convenience.Tucked just off the beaten path on a serene and scenic country road, this southern Vermont retreat offers the rare combination of privacy and accessibility, only minutes to town shopping, ski mountains, and one of Vermont’s largest lakes.Inside, the home is filled with bright, cheerful spaces, warm hardwood floors, and an inviting

  Amy Carson Lowe's Real Estate, LLC

  136 Yeaw Rd, Dover, VT 05341
• 

  

  /20

  $449,000

  • 4 Beds
  • 2 Baths
  • 2,219 Sq Ft

  45 Dover Hill Rd, East Dover, VT 05341

  Recently renovated 1900s Colonial just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access off a paved town road. This cozy Vermont retreat sits on 3+ acres with established trails, a gurgling brook wrapping around the home, bridge to access the rear upper meadow, perennial landscaping, and more. The home is being offered

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Dover Hill Rd, East Dover, VT 05341
• 

  

  /42

  $529,990

  • 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

  Flex Realty Group Flex Realty

  555 Vermont 9, Wilmington, VT 05363

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