Windham County VT Homes for Sale

• 

  

  /2

  $25,000

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

  28 Upper Howes Way, Wilmington, VT 05363

  Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house

  Sigrid Pickering Chimney Hill Realty

  28 Upper Howes Way, Wilmington, VT 05363
• 

  

  

  /23

  $470,000

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

  6D White Oaks Loop Unit 7, Dover, VT 05356

  Welcome to this spacious end-unit Timber Creek condominium, ideally located directly across from Mount Snow. This highly desirable community offers the perfect blend of mountain convenience and resort-style amenities, making it an exceptional year-round getaway. The main level features a welcoming mudroom entry with built-in bench and cubbies, opening into the dining area that flows seamlessly

  Monique White Deerfield Valley Real Estate

  6D White Oaks Loop Unit 7, Dover, VT 05356
• 

  

  

  /20

  $195,000

  • Land
  • 46.2 Acres
  • $4,221 per Acre

  1499 Josh Rd, Halifax, VT 05358

  Looking for true peace and tranquility? This 46.2-acre parcel faces South/SW and is located in a gorgeous remote valley with no road noise or any sound other than the sound of the crystal-clear brook crashing down the valley and the wind in the trees! The parcel does have some improvements including a modified camper with a 1000 gallon holding tank, existing gravel driveway off Josh Road (class

  Chris Long BHG Masiello Brattleboro

  1499 Josh Rd, Halifax, VT 05358
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  /58

  $720,000

  • 4 Beds
  • 3 Baths
  • 4,379 Sq Ft

  587 Vermont 121, Grafton, VT 05146

  The Woolley House, located at 587 Route 121 East and built around 1818, is a rare and remarkably preserved 2.5 story brick residence in the Federal style. This home, originally constructed for early woolen mill owner John Woolley, features a side-hall layout, blind-arch entryway, and fanlight transom.Original details are beautifully preserved throughout, including four elegant Regency

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /5

  $72,000

  • Land
  • 6.21 Acres
  • $11,594 per Acre

  0 Crane Mountain Rd, Townshend, VT 05353

  Nestled on top of Townshend Acres this 6.21 acre surveyed lot offers a amazing opportunity to build your dream home . This mostly level wooded parcel has easy access to a town-maintained road near a neighborhood community . Outdoor activities abound ; hiking , hunting , snowmobiling all available ...outside your door. Minutes from four seasons resorts for skiing, music and biking. Convenient to

  Janet Lucier Barrett & Valley Assoc. Inc

  0 Crane Mountain Rd, Townshend, VT 05353
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  /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 11 acres of landscaped grounds with lawns, stone walls, gardens, and woodland 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 a covered porch that opens into a marble floored foyer

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
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  /51

  $244,900 Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  72 Morningside Commons, Brattleboro, VT 05301

  Move up to a designer condo! Impeccable detailing by an IKEA design team raised this unit to a high level of quality. From the marble floor entrance to the architectural ceiling over the dining area to the custom kitchen and bathroom installations to the decorator lighting to the PAX closet wardrobe systems... it all speaks "beautiful". Newer features include a propane boiler and hot water heater

  Sally Fegley BHG Masiello Brattleboro

  72 Morningside Commons, Brattleboro, VT 05301
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  /17

  $285,000

  • 1 Bed
  • 1 Bath
  • 1,320 Sq Ft

  116 Birge St Unit 2, Brattleboro, VT 05301

  Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors—magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

  Christine Lewis Brattleboro Area Realty

  116 Birge St Unit 2, Brattleboro, VT 05301
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  /32

  $499,000

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  77 Buttonwood Dr, Brattleboro, VT 05301
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  /33

  $915,000

  • 3 Beds
  • 2.5 Baths
  • 1,529 Sq Ft

  761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360

  Originally a two bedroom and a one bedroom, this premiere condominium has been creatively converted into a very special family retreat. Completely renovated throughout----now three full bedrooms plus a den or office area, which could also serve as a fourth sleeping area--if so desired. You will also find two and a half beautifully renovated baths. The primary bedroom is oversized with a beautiful

  Edwin Kevil Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360
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  /35

  $425,000

  • 4 Beds
  • 3 Baths
  • 4,488 Sq Ft

  35 School St, Bellows Falls, VT 05101

  This single-family Victorian home located in the village of Bellows Falls has lots of space for family and friends! Four bedrooms, three full baths, a second-floor laundry room, two kitchens, two living rooms, three bonus rooms, and even an area for a potential apartment above the one-car garage! The open-concept updated kitchen/living room offer plenty of storage and seating for everyone and

  Heather Gleim CENTURY 21 North East

  35 School St, Bellows Falls, VT 05101
• 

  

  /23

  $159,000 Coming Soon

  • 1 Bed
  • 1 Bath
  • 592 Sq Ft

  219 High St Unit 3, Brattleboro, VT 05301

  Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

  Kristen Ziter Taylor Brattleboro Area Realty

  219 High St Unit 3, Brattleboro, VT 05301
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  /18

  $285,000

  • 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
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  /22

  $110,000

  • Land
  • 2.5 Acres
  • $44,000 per Acre

  69 Old Haven Ln, Putney, VT 05346

  Nestled in an idyllic setting at 69 Old Haven Lane, this exceptional building lot offers a rare opportunity to bypass the typical hurdles of new construction and start bringing your vision to life immediately. Located in a sought-after and peaceful pocket of Putney, this property perfectly balances the privacy of a country retreat with the convenience of an excellent location. Much of the

  Kate Barry EXP Realty

  69 Old Haven Ln, Putney, VT 05346
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  /12

  $159,500

  • 1 Bed
  • 1 Bath
  • 685 Sq Ft

  39 Brookside Dr Unit 7, Brattleboro, VT 05301

  Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. Located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Shared basement with assigned storage space. Association fees include heat,

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 7, Brattleboro, VT 05301
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  /30

  $495,000 Open Sat 10AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  313 S Pine Banks Rd, Putney, VT 05346

  Experience the Magic of Putney, Vermont. Discover a private sanctuary in the heart of Vermont’s "Craft Capital." This meticulously maintained ranch offers the perfect blend of secluded country living and proximity to Putney’s vibrant cultural hub. Known for its world-class arts scene, organic farms, Yellow Barn Music, Next Stage Arts, Putney COOP, and iconic institutions like Sandglass Theater

  Thomas Dahlin Berkley & Veller Greenwood Country

  313 S Pine Banks Rd, Putney, VT 05346
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  /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
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  /44

  $530,900

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

  37B Kingswood Rd, Dover, VT 05356

  Refined mountain luxury meets effortless four-season living in this impeccable Kingswood townhome, offering direct snowmobile trail access and private shuttle service to Mount Snow. Ideally positioned on the level portion of the development, this exceptional four-bedroom residence enjoys convenient trail access and a more expansive, usable, level rear yard—a rare and highly sought-after offering

  Michelle O'Neil Deerfield Valley Real Estate

  37B Kingswood Rd, Dover, VT 05356
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  /8

  $195,000

  • Land
  • 4.86 Acres
  • $40,123 per Acre

  0 Stoney Brook Rd, Londonderry, VT 05148

  4.86 acre building lot in Londonderry, Vermont with mountain views of Stratton and Bromley, offering privacy, elevation, and a compelling Southern Vermont setting. Access and building site are roughed in, and the property includes a State of Vermont wastewater permit for a 5 bedroom single family residence. Private setting, just minutes to Magic Mountain Ski Area and Londonderry Marketplace, with

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  0 Stoney Brook Rd, Londonderry, VT 05148
• 

  

  /55

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  57 Oak Ln, Jamaica, VT 05343

  This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

  Mike England Michael England Real Estate

  57 Oak Ln, Jamaica, VT 05343
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  /15

  $309,000

  • Land
  • 30 Acres
  • $10,300 per Acre

  00 Pratt Bridge Rd, Jamaica, VT 05343

  Thinking of building!! Enjoy Vermont in all the seasons!! This land has a number of options! A sectioned parcel of 30 acres of land has been already approved for a 4 lot subdivision with state approved septic designs. OR develop one site to sell and keep one for yourself with more land to share. OR keep it all to yourself and build your dream home. Pratt Bridge Road is a close drive to Stratton,

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  00 Pratt Bridge Rd, Jamaica, VT 05343
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  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  /60

  $725,000

  • 6 Beds
  • 3 Baths
  • 3,630 Sq Ft

  5 William Mundell Rd, South Newfane, VT 05351

  Just a short drive from the slopes of Mount Snow, this beautifully renovated 1800s Vermont farmhouse seamlessly blends historic charm with modern comfort. Situated on 7.5 picturesque acres just beyond the Dover town line in South Newfane, the property offers rolling pasture, classic stone walls, established gardens, and multiple outbuildings, all with easy access to nearby villages, lakes, and

  The Malley Group KW Vermont

  5 William Mundell Rd, South Newfane, VT 05351
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  /39

  $725,000

  • 5 Beds
  • 4 Baths
  • 2,962 Sq Ft

  250 Valley View Rd, Dover, VT 05356

  Unique, spacious, and just minutes to Mount Snow, this 5-bedroom, 4-bath home with a private pond is the kind of property buyers wait for. Whether for personal use, a vacation getaway, or short-term rental potential, it offers a setting to enjoy every season. Set on a beautiful 2-acre lot, the home features a large open-concept main living area with a cathedral ceiling and oversized windows that

  Melissa Nebelski Real Broker LLC

  250 Valley View Rd, Dover, VT 05356
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  /60

  $825,000

  • 2 Beds
  • 2 Baths
  • 2,220 Sq Ft

  177 Vermont 121, Grafton, VT 05146

  Get your own Corner of the Sky! Experience an extraordinary 17-acre hilltop retreat offering absolute seclusion, yet situated just a short walk from the heart of historic Grafton Village. Enjoy morning pastries at the general store or a cocktail at the Inn, then retreat to your private sanctuary. The sun-drenched 2-bedroom, 2-bathroom residence has been meticulously renovated for the modern

  Heidi Bernier Berkley & Veller Greenwood Country

  177 Vermont 121, Grafton, VT 05146
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  /43

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 2,295 Sq Ft

  31 Poplar Ln, Vernon, VT 05354

  Is complete privacy important to you? How does this beautiful 3-bedroom, 3 bath home with a two-car garage on 12+ acres sound? This attractive property is located in Vernon's desirable "Central Park Estates" neighborhood amongst other well-kept homes and a mile or so to the beloved Vernon Recreation Center. Just off of a quiet, side-road cul-de-sac, enter the property down the driveway through

  Stephanie Peduzzi-Baker Brattleboro Area Realty

  31 Poplar Ln, Vernon, VT 05354
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  /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
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  /23

  $189,000

  • Land
  • 3.6 Acres
  • $52,500 per Acre

  00 Lake Hill Rd, Whitingham, VT 05361

  Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing & septic design showing positive results,

  Chad Lackey Deerfield Valley Real Estate

  00 Lake Hill Rd, Whitingham, VT 05361
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  /31

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  459 Silver Ln, Wardsboro, VT 05355

  Come and visit your potential get away in the much sought after development of Snow Mountain Farms in Wardsboro, VT. This community offers an indoor swimming pool, tennis courts and an exercise facility for an extremely modest fee. A three-bedroom, one bonus room home has the perfect balance of Vermont charm and comfort for you and your guests. With recently installed floors and all new

  Peggy O'neill Cummings & Co

  459 Silver Ln, Wardsboro, VT 05355
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  /36

  $1,590,000

  • 5 Beds
  • 4.5 Baths
  • 4,325 Sq Ft

  19 Boulder Ridge Dr Unit 19 B, Dover, VT 05356

  Once in a while, a property comes along that truly leaves you speechless — and this is one of those rare moments. This 5-bedroom, 4.5-bath Boulder Ridge townhome has been meticulously renovated with precision and style at every turn. This is not the Boulder Ridge you've known before, and it's being offered completely turn-key.This immaculate unit sits in an ideal location with unobstructed

  Adam Palmiter Berkley & Veller Greenwood/Dover

  19 Boulder Ridge Dr Unit 19 B, Dover, VT 05356
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  /17

  $339,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  274 Vermont Route 100, Dover, VT 05356

  This storybook log cabin is the kind of place you picture when you think "perfect Vermont getaway." Tucked in the middle of town, everything you want is right here, and Mount Snow resort is just over a mile away. Whether you’re chasing powder days, snowmobile/summer trails, or just a cozy escape, this spot makes it easy to do it ALL. On the MOOver public transportation route to get you around

  Prema Fitzpatrick Real Broker LLC

  274 Vermont Route 100, Dover, VT 05356
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  /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
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  /9

  $480,000

  • Land
  • 7.8 Acres
  • $61,538 per Acre

  16 Overlook Dr, Dover, VT 05356

  A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 7.8 acres of land with a home site featuring full panoramic mountain and woodland views to the north and east, including mountain views to undeveloped national forest land. This property is the largest and most private lot in The Peaks community, providing a

  Patricia Fitzpatrick Skihome Realty

  16 Overlook Dr, Dover, VT 05356
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  /8

  $480,000

  • Land
  • 5.08 Acres
  • $94,488 per Acre

  10 Overlook Dr, Dover, VT 05356

  A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 5.08 acres of land and features full panoramic mountain and woodland views to the south, including mountain views to undeveloped national forest land. This property is one of the most private lots in The Peaks community, providing a full immersion in the woods

  Patricia Fitzpatrick Skihome Realty

  10 Overlook Dr, Dover, VT 05356
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  /17

  $729,000

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

  778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155

  Ski-In/Ski-Out Perfection: Your Premier Stratton Mountain Retreat! Experience the ultimate Vermont lifestyle in this rare 2-bedroom, 2-bathroom condo, perfectly positioned for true ski-in/ski-out convenience. Located just steps from the Villager Chairlift and the bustling heart of Stratton Village, this residence offers a seamless transition from the slopes to your front door.Designed with

  Robin Apps Four Seasons Sotheby's Int'l Realty

  778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155
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  /43

  $625,000

  • 5 Beds
  • 3 Baths
  • 2,600 Sq Ft

  15 Bills Rd, West Wardsboro, VT 05360

  This spacious five-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it’s perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  15 Bills Rd, West Wardsboro, VT 05360
• 

  

  /40

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  1355 Whitneyville Rd, Halifax, VT 05301

  Welcome to this charming country log home set on 30.6 private acres at the peaceful end of the road. Thoughtfully positioned to capture its surroundings, the home sits just high enough to enjoy pleasant views and beautiful mountain sunsets, best experienced from the inviting covered porches and open deck. Inside, the open-concept main level features abundant windows and cathedral ceiling creating

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  1355 Whitneyville Rd, Halifax, VT 05301
• 

  

  /40

  $4,087,000

  • 6 Beds
  • 7 Baths
  • 7,090 Sq Ft

  22 Stags Leap Ln, Wilmington, VT 05363

  Spectacular custom home at the base of the Hermitage Club in the Stags Leap community, adjacent to the ski trails at the base of Haystack mountain. This is a rare lot overlooking the trails, with direct ski-on/off and lift access, mountain views, and sunsets beyond, unimpeded by any other homes. Featuring 6 bedrooms, 5 and two half baths, with luxurious high ceiling great room with exposed

  Adam Palmiter Berkley & Veller Greenwood/Dover

  22 Stags Leap Ln, Wilmington, VT 05363
• 

  

  /60

  $420,000

  • 4 Beds
  • 2 Baths
  • 2,723 Sq Ft

  405 Main St, Wardsboro, VT 05355

  Lovingly shaped over generations of ownership, this is one of those special properties where the setting, charm, and character come together in a way that simply cannot be replicated. Set on 1.10 acres along a woodland creek, this property shines with natural beauty and Vermont charm. A stream-fed pond adds to the tranquil setting, while old stone walls, mature trees, butterfly gardens, and

  Rachel Febbie EXP Realty

  405 Main St, Wardsboro, VT 05355
• 

  

  /16

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  10 Riverfront Dr, Bellows Falls, VT 05101

  This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

  Gale Alger

  10 Riverfront Dr, Bellows Falls, VT 05101

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