Windham County VT Homes for Sale

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  /43

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  34 Johnson Hill Rd, Dover, VT 05356

  Nestled on a corner parcel in the desirable Dover Hills area near Mount Snow, this beautiful chalet offers the perfect low-maintenance four-season retreat. Designed for easy upkeep and effortless enjoyment, the home combines warm mountain charm with modern amenities, abundant natural light, and true move-in-ready convenience. Ideally located just minutes from skiing, snowmobile trails, golf,

  Donald Koelsch Deerfield Valley Real Estate

  34 Johnson Hill Rd, Dover, VT 05356
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  /36

  $1,275,000

  • 5 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4427 W Hill Rd S, Jamaica, VT 05343

  One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

  Carrie Mathews Winhall Real Estate

  4427 W Hill Rd S, Jamaica, VT 05343
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  /60

  $1,300,000

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft

  580 Cross Rd, South Londonderry, VT 05155

  Thoughtfully designed with both craftsmanship & efficiency in mind, the home exceeds modern energy standard, achieving an impressive energy efficient rating. 3-bedroom, 2-bath barn-style residence with 1-bedroom guest house & sauna. The 5BR Wastewater permit allows for potential future expansion/addition. A Masterful fusion of heritage & refined elegance, situated on 5.4 pristine acres. Absorb

  Loana Sargent Wohler Realty Group

  580 Cross Rd, South Londonderry, VT 05155
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  /39

  $610,000

  • 4 Beds
  • 3 Baths
  • 3,700 Sq Ft

  53 Country Ln, Wardsboro, VT 05355

  Tucked between Mount Snow and Stratton, this charming mountain retreat offers the perfect blend of adventure, comfort, and classic Vermont living. Set in the heart of Wardsboro, this property provides easy access to both year-round recreation and peaceful natural surroundings. After a day on the slopes or exploring the nearby Green Mountain National Forest, cozy up beside the inviting wood

  Mike Masters Four Seasons Sotheby's Int'l Realty

  53 Country Ln, Wardsboro, VT 05355
• 

  

  

  /11

  $174,000

  • Land
  • 15 Acres
  • $11,600 per Acre

  491 Whitneyville Rd, Halifax, VT 05358

  Tucked away along a quiet, town-maintained dead-end road, this private 15-acre parcel offers a rare combination of seclusion, character, and natural beauty. Set high on a peaceful knoll, the property features an old homesite's stone foundation, open meadow areas, and several mature apple trees that hint at the land’s past, also a drilled well.A gentle babbling brook traces one boundary,

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  491 Whitneyville Rd, Halifax, VT 05358
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  /60

  $474,500

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  287 Powder Mill Rd, Londonderry, VT 05148

  Nestled in the heart of Vermont’s scenic countryside, this beautifully maintained log cabin offers the perfect blend of rustic charm and cozy comfort. Surrounded by nature and timeless New England beauty, the home welcomes you with warm wood interiors, exposed beams, and an inviting atmosphere ideal for year-round living or a peaceful getaway. Thoughtfully cared for and full of character, the

  Joe Castaluccio Winhall Real Estate

  287 Powder Mill Rd, Londonderry, VT 05148
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  /42

  $1,150,000

  • 4 Beds
  • 1 Bath
  • 1,972 Sq Ft

  2245 Burrington Hill Rd, Whitingham, VT 05361

  Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to

  Michael Purcell Berkley & Veller Greenwood/Dover

  2245 Burrington Hill Rd, Whitingham, VT 05361
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  /27

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,377 Sq Ft

  366 Hague Rd, Dummerston, VT 05301

  Historical build by local artist, incorporating wood pews and other architectural pieces reclaimed from an old Vermont church, culminating into a beautiful country home. Appreciate the picturesque views of this 5.5+- acres located on a quiet road, looking south to a lovely meadow, complete with fruit trees and a pine-lined border. This home is perfectly sized with 3 bedrooms, 2 baths and a large

  Kristen Ziter Taylor Brattleboro Area Realty

  366 Hague Rd, Dummerston, VT 05301
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  /44

  $675,000

  • 5 Beds
  • 3 Baths
  • 2,916 Sq Ft

  34 Ellis Brook Rd, Dover, VT 05356

  Tucked along the peaceful banks of Ellis Brook in Dover, this spacious 5-bedroom home offers the perfect blend of comfort, privacy, and year-round recreation. Set on an expanded parcel that includes the neighboring lot for added space and seclusion, the property provides a serene Vermont setting with the soothing sounds of the babbling brook just beyond the backyard. Inside, the warm and inviting

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  34 Ellis Brook Rd, Dover, VT 05356
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  /55

  $418,000

  • 3 Beds
  • 2 Baths
  • 1,378 Sq Ft

  6 Outer Limits Ln, Wilmington, VT 05363

  Nestled in the coveted Chimney Hill Community, this charming 3-bedroom, 2-bathroom turn-key home is a delightful find. The main level features a convenient bedroom and full bath, along with a laundry area, a well-appointed kitchen, a dining room, and a cozy living room complete with a gas fireplace. Double sliding doors lead to a spacious deck, inviting an abundance of natural light. The home

  Donna Brown Skihome Realty

  6 Outer Limits Ln, Wilmington, VT 05363
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  /48

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  1905 Turkey Mountain Rd, Jamaica, VT 05343

  BEST AND FINAL OFFERS DUE BY WEDNESDAY, MAY 27TH AT 5PMWelcome to Cloister Falls, a truly special offering in the Green Mountains! Tucked among extensive grounds with mature gardens, a pond, and thoughtfully landscaped outdoor spaces, this 3+ bed 3 bath log home offers a setting that feels connected to the surrounding Vermont landscape. The property's signature feature is its swimming hole

  Jacki Murano Southern Vermont Realty Group

  1905 Turkey Mountain Rd, Jamaica, VT 05343
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  /44

  $695,000

  • 4 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  54 Main St, Grafton, VT 05146

  This home IS quintessential Grafton Vermont! Built c. 1850 this stately 4 over 4 colonial served as the Parsonage for the Grafton Church as it is still referred to this day. Privately owned for nearly 30 years this handsome home is ready for new stewardship. Spacious and sturdy, this vintage gem offers plenty of space and has been updated for today’s lifestyle. The first floor offers open concept

  Jessica Landers Barrett and Valley Associates Inc.

  54 Main St, Grafton, VT 05146
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  /24

  $399,000

  • 7 Beds
  • 3 Baths
  • 3,700 Sq Ft

  197 Western Ave, Brattleboro, VT 05301

  Excellent opportunity to own a well-maintained and fully occupied 3-unit investment property in the heart of Brattleboro. Located in-town with convenient access to shopping, restaurants, entertainment, and everyday amenities, this property offers strong in-place income with additional upside potential. The building consists of two 2-bedroom units and one spacious 3-bedroom unit and has been

  Karen Hoppe Berkley & Veller Greenwood Country

  197 Western Ave, Brattleboro, VT 05301
• 

  

  /22

  $399,000

  • 9 Beds
  • 3 Baths
  • 3,286 Sq Ft

  19 Canal St, Brattleboro, VT 05301

  Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an

  Karen Hoppe Berkley & Veller Greenwood Country

  19 Canal St, Brattleboro, VT 05301
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  /59

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,345 Sq Ft

  52 Ruth Way, Wilmington, VT 05363

  Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for

  Donna Brown Skihome Realty

  52 Ruth Way, Wilmington, VT 05363
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  /29

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  18 Ripple Ln, Bellows Falls, VT 05101

  Welcome to peaceful country living with room to breathe. Nestled on a private road, this well-maintained 3-bedroom, 13⁄4-bath ranch offers privacy, comfort, and over 13 acres of beautiful land to enjoy. The home's single-level layout provides convenient living with spacious bedrooms, functional living areas, and a comfortable flow for everyday life and entertaining. A two-car garage offers plenty

  Rob Weltz Barrett and Valley Associates Inc.

  18 Ripple Ln, Bellows Falls, VT 05101
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  /44

  $295,000

  • 2 Beds
  • 1.5 Baths
  • 1,494 Sq Ft

  298 Governor Hunt Rd, Vernon, VT 05354

  Convenient single-level living in a setting that perfectly captures the warmth and charm of small-town life. Currently offering two bedrooms along with a flexible bonus room that could easily serve as a third bedroom or home office, the town recognizes the property as a four-bedroom home. In recent years, however, the property has been thoughtfully utilized as office/commercial space. Designed

  Kerry Mulverhill

  298 Governor Hunt Rd, Vernon, VT 05354
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  /26

  $75,000

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

  170 Maple Dr, Wardsboro, VT 05355

  Are you looking for a beautiful, build-ready lot in Southern Vermont? This one-acre parcel at 170 Maple Drive in the Snow Mountain Farms community offers the perfect opportunity to start your Vermont dream home. The property already has a state-issued 4-bedroom wastewater permit in place, making it ready for your 2026 build. Located on a town-maintained road with a quiet cul-de-sac setting, this

  Chris Lowe Lowe's Real Estate, LLC

  170 Maple Dr, Wardsboro, VT 05355
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  /47

  $429,900

  Open Mon 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft

  1422 Merrifield Rd, Whitingham, VT 05361

  NEW LOG HOME LISTING ON 5+ ACRES WITH BARN AND GARAGE!! OPEN HOUSE MONDAY, MAY 25th, 11am to 1pm This true log home offers 3 beds and 2 baths, a garage, and barns in a setting designed for year-round enjoyment. Offering just over five acres with open fields, meadows, mature gardens, stone walls and stone gardens, perennial plantings, outbuildings, and charm! Inside, hardwood and tile floors, high

  Jacki Murano Southern Vermont Realty Group

  1422 Merrifield Rd, Whitingham, VT 05361
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  /9

  $165,000

  • Land
  • 1.9 Acres
  • $86,842 per Acre

  Lot A Sweet Pond Rd, Guilford, VT 05301

  Beautiful open 1.9-acre parcel on scenic Sweet Pond Road in Guilford, VT. Featuring open pastureland, generally level terrain, and excellent southern exposure, this property offers a wonderful opportunity for a primary residence, homestead, recreation property, or investment. A classic stone wall borders the western edge, adding timeless Vermont character. Buyers to verify utility availability

  Erica Reynolds Southern Vermont Realty Group

  Lot A Sweet Pond Rd, Guilford, VT 05301
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  /41

  $1,385,000

  • 4 Beds
  • 3.5 Baths
  • 4,153 Sq Ft

  487 Vermont Route 100, Londonderry, VT 05148

  Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a

  Jamie Wylie Stratton Real Estate

  487 Vermont Route 100, Londonderry, VT 05148
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  /43

  $679,000

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  148 Townshend Rd, Grafton, VT 05146

  This circa 1860 Greek Revival home is one of Grafton Village’s gems, blending historic character with recent, thoughtful renovations. A sweeping backyard framed by rugged stone walls adds to the property’s appeal, while established perennials and a welcoming side porch create an inviting entrance. The delightful country kitchen flows into the formal dining room and living room, where a propane

  Heidi Bernier Berkley & Veller Greenwood Country

  148 Townshend Rd, Grafton, VT 05146
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  /39

  $2,195,000

  • 4 Beds
  • 4 Baths
  • 3,524 Sq Ft

  392 Lake Raponda Rd, Wilmington, VT 05363

  A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake — with a private dock — just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats

  Adam Palmiter Berkley & Veller Greenwood/Dover

  392 Lake Raponda Rd, Wilmington, VT 05363
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  /23

  $339,000

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  117 Oak Grove Ave, Brattleboro, VT 05301

  Located in one of the area’s most desirable and close-knit neighborhoods, this beautifully preserved 1929 home blends timeless character with thoughtful updates. Featuring hardwood floors, natural woodwork, custom built-ins, classic wainscoting, and a welcoming mudroom, the home retains the charm and craftsmanship buyers love. The open and inviting first floor offers generous living space and a

  Liz LaVorgna Brattleboro Area Realty

  117 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /22

  $167,500

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft

  116 Buck Hill, Jamaica, VT 05343

  Tucked away at the end of a shared driveway, this charming cottage chalet offers a wonderful sense of privacy on nearly three acres of picturesque land. The setting is a perfect blend of open lawn surrounding the home and peaceful mixed woodlands beyond, creating a serene retreat in every season. A storage shed provides added convenience, while both front and rear decks invite you to relax,

  Robert Doyle Berkley & Veller Greenwood Country

  116 Buck Hill, Jamaica, VT 05343
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  /35

  $570,000

  • 4 Beds
  • 2.5 Baths
  • 2,359 Sq Ft

  116 Teacher Rd, Jamaica, VT 05343

  Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time

  Carrie Mathews Winhall Real Estate

  116 Teacher Rd, Jamaica, VT 05343
• 

  

  /22

  $595,000

  • 4 Beds
  • 2 Baths
  • 1,430 Sq Ft

  9 Mountain Acres Rd, Jamaica, VT 05343

  Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system

  Carrie Mathews Winhall Real Estate

  9 Mountain Acres Rd, Jamaica, VT 05343
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  /42

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  147 Gilbert Rd, Guilford, VT 05301

  This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting

  Monica Sumner BHG Masiello Brattleboro

  147 Gilbert Rd, Guilford, VT 05301
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  /60

  $1,215,000

  • 4 Beds
  • 3 Baths
  • 3,632 Sq Ft

  350 Sunset Lake Rd, Newfane, VT 05301

  Experience the timeless charm of Vermont living at this beautifully renovated farmhouse estate sitting on 92 acres in Newfane Vermont. Originally restored and thoughtfully updated, this exceptional antique farmhouse seamlessly blends historic character with modern comfort and convenience. Unlike many older homes, this property features expansive rooms, high ceilings, wood floors, abundant natural

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  350 Sunset Lake Rd, Newfane, VT 05301
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  /16

  $185,000

  • Land
  • 16.05 Acres
  • $11,526 per Acre

  00 E Hill Rd, Wardsboro, VT 05355

  Discover the perfect setting for your Vermont dream on 00 East Hill Road in Wardsboro. This impressive 16.05-acre parcel captures the essence of the Green Mountains, offering a blend of absolute privacy and breathtaking mountain views. Whether you envision a contemporary mountain escape or a classic timber-frame homestead, this expansive acreage provides an incredible canvas characterized by its

  Steve Lawrence KW Vermont-Stowe

  00 E Hill Rd, Wardsboro, VT 05355
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  /15

  $215,000

  • 2 Beds
  • 1 Bath
  • 691 Sq Ft

  8581 Vermont 30 Unit B, Jamaica, VT 05343

  Escape to the mountains in this charming 2-bedroom/1 bath condominium conveniently located near premier ski areas and year-round outdoor recreation. It's only 15 minutes to Stratton, 20 minutes to Bromley, and 10 to the Jamaica State Park. Enjoy easy access to skiing, hiking, biking, golf, and snowmobile trails, all just minutes from your door, and Manchester's shopping and dining are 30 minutes

  Deborah Hanst

  8581 Vermont 30 Unit B, Jamaica, VT 05343
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  /53

  $200,000

  • 384 Sq Ft

  91 Vermont 35, Athens, VT 05143

  A little piece of heaven awaits you at this charming camp set on 44 acres. The cabin sits high on a knoll overlooking a beautiful view of the expansive lower field and the distant hills. The wrap-around porch afford a birds-eye view of the changing seasons and the perfect perch to observe wildlife. The land – a great mix of fields, hills and woods – is an oasis for year-round outdoor recreation.

  Laura D'Angelo Berkley & Veller Greenwood Country

  91 Vermont 35, Athens, VT 05143
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  /24

  $380,000

  • 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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  /43

  $125,000

  • 2 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  1940 Vermont 30, Jamaica, VT 05343

  YES this is a FULL time Residence ... Charming two-bedroom, two-bathroom mobile home situated along the scenic West River. The property includes two small storage buildings, a fruit tree screened enclosure, and a carport. Inside, there is ample space for comfort with two living rooms, one of which opens to a deck with picturesque views of the river. Located just 30 minutes from Stratton, Mount

  Mike England Michael England Real Estate

  1940 Vermont 30, Jamaica, VT 05343
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  /49

  $358,300

  • 2 Beds
  • 1.5 Baths
  • 1,701 Sq Ft

  214 Pine Acres Rd, Townshend, VT 05353

  Pristine and charming 2-bedroom log cabin with long-range mountain views coming soon in Townshend, Vermont! Showings begin Saturday, May 23rd at the Open House from 10:00 AM–2:00 PM. This beautifully maintained home offers the perfect blend of natural beauty, privacy, and thoughtful craftsmanship. Meticulously cared for, the home is truly move-in ready and designed for comfortable,

  Jessica Landers Barrett and Valley Associates Inc.

  214 Pine Acres Rd, Townshend, VT 05353
• 

  

  /29

  $205,000

  • 3 Beds
  • 2 Baths
  • 1,183 Sq Ft

  18 Lindy Rd, Vernon, VT 05354

  Welcome to this charming and well-maintained 3-bedroom, 13⁄4-bath single-level home, offering the ease and comfort of first-floor living. Tucked at the end of Lindy Road, the property provides a peaceful setting on a spacious, level 0.58-acre lot, surrounded by mature trees that offer both natural shade and privacy. Inside, the home is bright, open, and thoughtfully designed, creating an inviting

  Kerry Mulverhill

  18 Lindy Rd, Vernon, VT 05354
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  /39

  $875,000

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

  1D Townhouse Square Unit 8, Dover, VT 05356

  Ski-on and off from this beautifully updated Seasons townhome trailside on the Mount Snow ski resort. Ski home for lunch and then get back on the slopes for the afternoon, without ever having to take off your boots. This well appointed unit features a large open concept living space with vaulted ceiling, floor to ceiling stone chimney with wood burning fireplace, tremendous natural light from the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1D Townhouse Square Unit 8, Dover, VT 05356
• 

  

  /40

  $899,000

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

  9D Dover Springs Ln, Dover, VT 05356

  Stunning updated Greenspring unit, just across the street from the Mount Snow ski resort with stunning direct views of the ski trails. This 4 bedroom, 4 bath unit features extensive upgrades, new furnishings, and immaculate condition, to ensure turn key enjoyment. Features include an open concept great room with vaulted ceiling and wood burning two sided fireplace, sunny exposure and sunset/ski

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9D Dover Springs Ln, Dover, VT 05356
• 

  /2

  $149,000

  • Land
  • 16.74 Acres
  • $8,901 per Acre

  9 Brown Rd, Wilmington, VT 05363

  Nice private almost 17 acre site with driveway, dug well, dug pond, sitework and ski area and Mountain views. Log cabin or post and beam home is a great fit. VAST snowmobile trail runs through the property. Beautiful bright and sunny exposure.

  Mark Yule BHG Masiello Brattleboro

  9 Brown Rd, Wilmington, VT 05363
• 

  

  /26

  $525,000

  • 2 Beds
  • 2 Baths
  • 2,481 Sq Ft

  1871 W Hill Rd, Townshend, VT 05353

  OPEN HOUSE - Sunday, May 24 from 2:00 - 4:00. Welcome to your fully furnished chalet-style escape in Townshend, Vermont. Set on 10 partially cleared, usable acres, this 2-bedroom, 2-bathroom home offers the perfect blend of privacy, comfort, and classic Vermont charm. Featuring additional living space in the loft and den, this property provides flexibility.Step inside to find a warm, inviting

  Kim Meeker Southern Vermont Realty Group

  1871 W Hill Rd, Townshend, VT 05353

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