Windham County VT Homes for Sale

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  $89,900

  • 4 Beds
  • 2 Baths
  • 1,902 Sq Ft

  206 Smith Rd, Jamaica, VT 05343

  Looking for a project? Featuring a drilled well, existing septic, electric, and driveway, you have a good start for a new build, renovation or a combination of the two. The cabin has been added onto many times, making room for a growing family. The land is mostly level, with some nice plantings and the house sits back a little distance from the neighbors. The well is being shared, electric is run

  Christine Lewis Brattleboro Area Realty

  206 Smith Rd, Jamaica, VT 05343
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  /30

  $334,000

  $65K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  1511 E Dover Rd, Wardsboro, VT 05355

  Tucked along a scenic stretch of East Dover Road, this charming Wardsboro property captures the essence of Vermont country living with the added bonus of easy access to some of Southern Vermont’s most sought-after destinations. Just a short drive to Mount Snow and Stratton Mountain Resort, this location is ideal for year-round recreation—from skiing and snowboarding in the winter to hiking,

  Mike Masters Four Seasons Sotheby's Int'l Realty

  1511 E Dover Rd, Wardsboro, VT 05355
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  /39

  $639,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft

  198 E Hill Rd, Wardsboro, VT 05355

  Gorgeous home with so many recent upgrades! Beautiful kitchen with newer updated appliances, baths, roof, windows, flooring, well pump, mini splits, high efficiency propane combo unit for heat and hot water, new pavement, three car detached garage, woodshed, fenced in doghouse area and so much more! This is truly MOVE IN READY! These are just a few of the items this homeowner has done to improve

  Julie Lowe Lowe's Real Estate, LLC

  198 E Hill Rd, Wardsboro, VT 05355
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  /39

  $55,000

  • Land
  • 21,780 Sq Ft
  • $110,000 per Acre

  404 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding,

  Sigrid Pickering Chimney Hill Realty

  404 Fox Mountain Rd, Wilmington, VT 05363
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  /60

  $999,000

  $89K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 5,828 Sq Ft

  151 Townshend Rd, Grafton, VT 05146

  STRONG RENTAL HISTORY & INVESTMENT OPPORTUNITY IN A TURN-KEY PROPERTY. Located in the heart of Grafton, Vermont, on a spacious one-acre, flat lot a quick stroll from town, this extensively renovated property offers exceptional flexibility and scale. The single family or multi-family property is configured to allow division into two condominium-style living spaces plus a separate artist loft or

  Erin McCormick KW Vermont

  151 Townshend Rd, Grafton, VT 05146
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  /23

  $260,000

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  429 Vt Route 30, Newfane, VT 05345

  Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  429 Vt Route 30, Newfane, VT 05345
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  /32

  $24,500

  • 1 Bed
  • 2 Baths
  • 869 Sq Ft

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356

  This unique style, a sleep six condo, is located on the top floor of the hotel and features two levels, including a loft bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area has a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping four people. The spacious loft bedroom features a king-size bed, a large walk-in closet, and an

  Patricia Fitzpatrick Skihome Realty

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
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  /36

  $599,000

  $20K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,354 Sq Ft

  556 Sawmill Rd, Wardsboro, VT 05355

  Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with a dedicated office space and attached garage offers over 3,000 square feet of living space. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment — from winter skiing and riding to relaxing summer

  Kim Meeker Southern Vermont Realty Group

  556 Sawmill Rd, Wardsboro, VT 05355
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  /8

  $74,900

  • Land
  • 1.1 Acres
  • $68,091 per Acre

  2 Johnson Hill, Dover, VT 05356

  Private 1.10 +/- Acre lot in Dover Hills VT. #WW-2-2888 Permit in place. Trinity Engineering did the engineering and the lot was approved for a three bedroom dwelling.

  Janet Boyd Boyd Real Estate

  2 Johnson Hill, Dover, VT 05356
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  /2

  $25,000

  • Land
  • 26,136 Sq Ft
  • $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
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  /23

  $470,000

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

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

  OPEN HOUSE ~ Memorial Day Weekend ~ Sunday May 24th ~ 12:00-2:00pm ~ 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

  Monique White Deerfield Valley Real Estate

  6D White Oaks Loop Unit 7, Dover, VT 05356
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  $715,000

  $5K PRICE DROP

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

  587 Vermont 121, Grafton, VT 05146

  Built in 1818 for early woolen mill owner John Woolley, the Woolley House is a rare and beautifully preserved Federal-style brick residence that blends historic character with the demands of contemporary life. Listed on the National Register of Historic Places within the Mechanicsville Historic District, this exceptional property offers unique architectural significance. Classic period details

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /38

  $749,000

  $46K PRICE DROP

  • 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
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  /17

  $255,000

  $30K PRICE DROP

  • 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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  $469,000

  $30K PRICE DROP

  • 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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  $915,000

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

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

  A rare opportunity in Long Trail House, this corner residence has been thoughtfully reimagined from two separate units into a spacious, fully renovated retreat designed for flexible living. The expanded layout now includes multiple sleeping areas and a den/office, offering versatility for guests or remote work. Natural light fills the home thanks to its corner position, while open living space

  Edwin Kevil Stratton Real Estate

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

  $399,900

  $25K PRICE DROP

  • 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
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  /30

  $100,000

  $10K PRICE DROP

  • Land
  • 2.5 Acres
  • $40,000 per Acre

  69 Old Haven Ln, Putney, VT 05346

  Escape to your own slice of Vermont paradise with this exceptional land offering on Old Haven Lane in highly desirable Putney. This serene, pristine lot offers the perfect canvas for your custom home, tucked away for ultimate privacy yet completely accessible to Putney’s vibrant town center, local schools, and cultural landmarks. Whether you are looking to hold a premium piece of land or break

  Kate Barry EXP Realty

  69 Old Haven Ln, Putney, VT 05346
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  /15

  $149,900

  $10K PRICE DROP

  • 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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  /20

  $195,000

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

  0 Stoney Brook Rd, Londonderry, VT 05148

  Long-range views of Stratton and Bromley define this 4.86 +/- acre offering in Londonderry, where elevation, privacy, and natural beauty come together in a compelling Southern Vermont setting. The access road and future building site are already roughed in, creating a strong foundation for a thoughtfully designed Vermont retreat.Supported by a State of Vermont wastewater permit for a

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  0 Stoney Brook Rd, Londonderry, VT 05148
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  /57

  $460,000

  Open Sat 10AM - 12PM $65K PRICE DROP

  • 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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  /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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  $700,000

  $25K PRICE DROP

  • 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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  /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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  /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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  /30

  $429,000

  $16K PRICE DROP

  • 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

  $250,000

  $230K PRICE DROP

  • Land
  • 7.8 Acres
  • $32,051 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

  $250,000

  $230K PRICE DROP

  • Land
  • 5.08 Acres
  • $49,213 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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  /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

  Robert Alger Alger Real Estate Agency

  10 Riverfront Dr, Bellows Falls, VT 05101
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  /60

  $319,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  3185 Higley Hill Rd, West Marlboro, VT 05363

  Vermont A-Frame Retreat in Marlboro! Escape to this charming 2-bedroom, 2-bath A-frame set on 2.18 wooded acres in scenic Marlboro, Vermont. With a stream, deck, and peaceful natural setting, this property offers the perfect blend of privacy and character. Inside, you’ll find 1,164 square feet of furnished living space featuring natural light, a wood fireplace, first-floor laundry, and a

  Grayson VanHendrick Flex Realty

  3185 Higley Hill Rd, West Marlboro, VT 05363
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  /49

  $275,000

  $75K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  106 Main St Unit 5, Putney, VT 05346

  Bright, airy, and full of personality, this charming two-bedroom, one-bathroom condo in the Village of Putney offers comfort, style, and convenience. Ideally located just minutes from I-91 and close to Putney’s vibrant downtown shops, cafés, and everyday amenities, this condo offers easy access to village life. Inside, natural light fills the thoughtfully designed space, highlighting dreamy

  Rebecca Hiam Southern Vermont Realty Group

  106 Main St Unit 5, Putney, VT 05346
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  /50

  $649,900

  $50K PRICE DROP

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

  300 Route 121 E, Grafton, VT 05146

  Nestled in a postcard-perfect riverfront 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

  Gary Coger Four Seasons Sotheby's Int'l Realty

  300 Route 121 E, Grafton, VT 05146
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  $625,000

  • 4 Beds
  • 2 Baths
  • 2,070 Sq Ft

  239 Valley View Rd, Dover, VT 05356

  This contemporary 3-bedroom plus loft, 2-bath home in Dover Hills offers both comfort and convenience. The property features a detached 2-car garage with overhead storage, an additional carport, and a wood shed. The recently remodeled kitchen boasts new cabinets, countertops, and appliances, complemented by wood floors throughout and new skylights that fill the space with natural light. A gas

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  239 Valley View Rd, Dover, VT 05356
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  /43

  $75,000

  $20K PRICE DROP

  • Land
  • 1 Acre
  • $75,000 per Acre

  169 Sun and Ski Rd, Wilmington, VT 05363

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

  Kim Meeker Southern Vermont Realty Group

  169 Sun and Ski Rd, Wilmington, VT 05363
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  /49

  $799,000

  $51K PRICE DROP

  • 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
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  /35

  $339,000

  $11K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft

  6795 Vt Route 100, Londonderry, VT 05148

  Motivated sellers! Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses –whether

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  6795 Vt Route 100, Londonderry, VT 05148
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  /44

  $799,000

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft

  39D Dover Springs Ln, Dover, VT 05356

  Located in the highly sought-after Greensprings community at Mount Snow, this spacious 4 bedroom, 4 bath townhouse offers the perfect blend of comfort, convenience, and year-round recreation.The bright, open-concept main living area features vaulted ceilings, abundant natural light, and a cozy fireplace ideal for gathering after a day on the slopes. Large windows and sliding doors invite the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  39D Dover Springs Ln, Dover, VT 05356
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  /41

  $1,600,000

  $150K PRICE DROP

  • 7 Beds
  • 5 Baths
  • 4,649 Sq Ft

  4669 Vermont Route 100, Londonderry, VT 05148

  Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with

  Story Jenks LandVest, Inc/Woodstock

  4669 Vermont Route 100, Londonderry, VT 05148

Showing Results 241 - 280, Page 7 of 12