Windham County VT Homes for Sale

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  /33

  $1,760,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

  Trailside!!! Ski in, ski out!! The very best Ski Direct Access at Stratton!! Most popular of luxury townhomes---offering an enlarged patio with Hot Tub, Open and Sunny, Four Bedrooms plus a Den Floorplan, Single Car Garage! Fully Furnished. Hardwood Flooring, floor to ceiling stone, wood burning fireplace! Enjoy this outstanding trailside location. And as an added benefit, the Stratton Training

  Edwin Kevil Stratton Real Estate

  89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
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  /3

  $625,000

  • 4 Beds
  • 1.5 Baths
  • 2,764 Sq Ft

  768 Vt Route 30, Jamaica, VT 05343

  Large farmhouse with 15.78 acres, metal roof, easy access to multiple ski resorts. Four bedrooms, one and a half baths. Large front and back yard, level with some fencing. Will need notice to show.

  Julie Lowe Lowe's Real Estate, LLC

  768 Vt Route 30, Jamaica, VT 05343
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  /16

  $449,000

  • 3 Beds
  • 3 Baths
  • 1,726 Sq Ft

  4A Suntec Loop Unit 4A, Dover, VT 05356

  Beautiful woodsy Suntec townhome just down from the base of the Mount Snow ski resort. This spacious 3 bedroom plus loft townhome sits about a mile south of Mount Snow, with direct access to snowmobile trails, and easy access to the nearby village of Wilmington and lakes. The unit has a large open concept floor plan with living room with wood burning fireplace and brick hearth, rustic wood

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4A Suntec Loop Unit 4A, Dover, VT 05356
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  /16

  $19,999

  • Land
  • 1 Acre
  • $19,999 per Acre

  32 Hunter Brook Rd, Newfane, VT 05351

  Beautiful creekside property in Newfane, ideal for camping, fishing, or RVing. The western boundary line follows Hunter Brook, which turns like a horseshoe at this location and almost meets the eastern boundary: Hunter Brook Road. As a result the property naturally divides itself into two sides, each with its own strengths and weaknesses.The northeastern side is larger, more private, and

  David White OwnerEntry.com

  32 Hunter Brook Rd, Newfane, VT 05351
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  /35

  $875,000

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

  9A Dover Springs Ln, Dover, VT 05356

  Greenspring townhome across the street from the Mount Snow ski resort with stunning direct views of the ski trails. This 4 bedroom, 4 bath unit is being offered by the original owners and has been well maintained and never rented. It features an an open concept floor plan with living room with vaulted ceiling and wood burning two sided fireplace, large kitchen with breakfast bar on the island,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9A Dover Springs Ln, Dover, VT 05356
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  /44

  $299,900

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  10 King St, Bellows Falls, VT 05101

  Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With

  Floyd Amidon Maple Leaf Realty

  10 King St, Bellows Falls, VT 05101
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  /14

  $210,000

  • Land
  • 35 Acres
  • $6,000 per Acre

  00 Vermont Route 100, Jamaica, VT 05343

  Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

  Patrice Schneider Southern Vermont Realty Group

  00 Vermont Route 100, Jamaica, VT 05343
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  /45

  $28,500

  • 1 Bed
  • 2 Baths
  • 771 Sq Ft

  204/206 Qtr 2 Grand Summit Way Unit 204/206 Qtr 2, Dover, VT 05356

  Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious valley-side lockout unit, comfortably sleeps 8. Unit 204 is a hotel room with 2 king-size beds, a full bath, & a deck. The adjoining

  Donna Brown Skihome Realty

  204/206 Qtr 2 Grand Summit Way Unit 204/206 Qtr 2, Dover, VT 05356
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  /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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  /36

  $499,000

  • Land
  • 41 Acres
  • $12,171 per Acre

  706 Vt Route 100, Stratton, VT 05360

  Exceptional New Offering! Rare 41± acres in Stratton with extraordinary 180 +/- long-range mountain views, improvements, base camp, driveway, clearings, trails, wildlife, and a substantial WOW factor. All for approx. $12,000/acre. A short drive in from paved Route 100, before the land rises further in elevation, sits the rustic 1-bed base camp overlooking open field and multiple ski

  Jacki Murano Southern Vermont Realty Group

  706 Vt Route 100, Stratton, VT 05360
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  /24

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  115 Country Hill, Brattleboro, VT 05301

  This lovely West Brattleboro cape is located on a quiet cul-de-sac right on the outskirts of town. Built in 2002 with a spacious design, you enter through the oversized two-car garage into a contemporary kitchen. Features include granite countertops, tile floors, an elegant backsplash, and a door leading to a private terrace, ideal for family gatherings or entertaining. The first floor has

  Kristen Ziter Taylor Brattleboro Area Realty

  115 Country Hill, Brattleboro, VT 05301
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  /33

  $229,000

  • 3,302 Sq Ft

  36 Barker St, Town of Rockingham, VT 05101

  This charming three-unit property in the heart of Bellows Falls, VT, offers a rare combination of historic character and modern appeal. With its exterior freshly painted in November 2025, the building exudes curb-appeal and care. Inside, the first-floor unit features three bedrooms and a full bath—perfect for a family or long-term tenant—while the second and third-floor units each offer two

  Rob Weltz Barrett and Valley Associates Inc.

  36 Barker St, Town of Rockingham, VT 05101
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  /60

  $875,000

  • 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
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  /35

  $620,000

  • 6 Beds
  • 4 Baths
  • 3,592 Sq Ft

  1375 Sheldon Hill Rd, Wardsboro, VT 05355

  Stunning unique 2024 renovated chalet with rare 2+ acre parcel and easy access to both Mount Snow and Stratton. This home exudes the vibe of a true Vermont ski retreat. Inside you are treated to a large open concept great room with vaulted ceilings, natural woodwork, and great natural light throughout thanks to large windows and transoms. There is a gas fireplace with stone hearth, upscale custom

  Adam Palmiter Berkley & Veller Greenwood/Dover

  1375 Sheldon Hill Rd, Wardsboro, VT 05355
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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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  /34

  $389,900

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft

  295 Stratton Arlington Rd, West Wardsboro, VT 05360

  Beautifully renovated 2-bedroom, 2-bath cottage on 1.9 acres in Stratton. Ideally located just minutes from both Mount Snow and Stratton ski areas, with the Stratton Recreation Center conveniently down the road. Enter through the mudroom into a bright, open-concept kitchen and dining space featuring a cozy woodstove and 4 skylights. The living room is spacious with a mini split and also includes

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  295 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /39

  $890,000

  • 5 Beds
  • 3.5 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  This majestic log home offers peaceful mountain living with room for Everyone. Discover your tranquil 5-bedroom, 4-bathroom family retreat nestled just minutes from the year-round activities at Stratton Ski Resort. This authentic and expansive log cabin exudes classic Vermont charm. The inviting main living area is flooded with natural light, featuring an efficient wood stove to provide cozy

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  4880 Pikes Falls Rd, Jamaica, VT 05343
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  /3

  $60,000

  • Land
  • 1.1 Acres
  • $54,545 per Acre

  63 Villager Loop, Dover, VT 05356

  Lovely wooded building site not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. View potential and easy access off a paved road, with a large corner lot location, looking to the west over the ski mountains and sunsets.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  63 Villager Loop, Dover, VT 05356
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  /37

  $874,000

  • 6 Beds
  • 3 Baths
  • 2,900 Sq Ft

  261 Handle Rd, Dover, VT 05356

  Slopeside 6 Bedroom Ski Chalet at Carinthia Base, Mount Snow This ski chalet is perfectly positioned at the base of Carinthia, offering true slopeside access and unmatched convenience. Step out your door and onto the trails, with the Carinthia Base Lodge, terrain parks, lifts, and all the action of the mountain just steps away. Inside, the home blends classic chalet character with thoughtful

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  261 Handle Rd, Dover, VT 05356
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  /25

  $349,000

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  337 Handle (Snow Tree Pines K) Rd Unit Pines K, Dover, VT 05356

  Welcome to this beautifully updated two bedroom, two-bathroom condo in the desirable upper Snow Tree community. The home is perfectly positioned to capture incredible mountain views and the true essence of Mount Snow base area living. Step inside to find a bright, inviting interior featuring new efficient windows, a cozy gas fireplace, and beautiful cathedral ceiling that enhances the spacious

  Melissa Ellis Southern Vermont Realty Group

  337 Handle (Snow Tree Pines K) Rd Unit Pines K, Dover, VT 05356
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  /38

  $475,000

  • Land
  • 133.1 Acres
  • $3,569 per Acre

  40 E Putney Brook Rd, Putney, VT 05346

  Awesome 133± Acre Country Parcel in Putney, Vermont. A rare opportunity to own 133± acres of picturesque Vermont land in highly desirable Putney. This large country parcel offers multiple access points, including generous frontage on a major road as well as two unpaved roads. Existing logging roads weave through the property, leading to several clearings ideal for building, recreation, or

  Geralyn Donohue Engel & Völkers Okemo

  40 E Putney Brook Rd, Putney, VT 05346
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  /4

  $160,000

  • Land
  • 9.3 Acres
  • $17,204 per Acre

  00 E Putney Brook Rd, Putney, VT 05346

  Located on E. Putney Brook Rd., approx. 2.5 miles from Putney Village, this beautiful, wooded 9+ ac property offers a desirable place to build. Bring your own building plans, power is nearby, and septic design is available. Clear a prime building site on level plateau and surround your home with mature woodlands. This county location offers easy access to orchards, farmstands for local produce,

  Heidi Bernier Berkley & Veller Greenwood Country

  00 E Putney Brook Rd, Putney, VT 05346
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  /55

  $1,345,000

  • 3 Beds
  • 2 Baths
  • 2,546 Sq Ft

  135 Fred Houghton Rd, Putney, VT 05346

  This one-of-a-kind Vermont property offers three dwellings on 5.6 acres - each blending elevated aesthetics, thoughtful design, and a true connection to nature. The 2011 main house features an open layout and handcrafted finishes throughout. The kitchen boasts soapstone countertops and custom cherry cabinetry. A very special wood-fired masonry heater anchors the living space and a spacious

  Benjamin Cote EXP Realty

  135 Fred Houghton Rd, Putney, VT 05346
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  /42

  $559,990

  • 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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  /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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  /28

  $265,000

  • 2 Beds
  • 1 Bath
  • 903 Sq Ft

  1555 W River Rd, Dummerston, VT 05301

  Welcome home to this inviting 2-bedroom, 1-bath Cape on scenic West River Road. Perfectly located just a short drive to downtown Brattleboro’s shops, restaurants, and local conveniences—just over a quarter mile to West River Park and about 30 minutes to Mount Snow—this home offers the ideal blend of country charm and everyday comfort. Set on a beautiful .6-acre lot with mature perennial trees and

  Morriah Adams BHG Masiello Brattleboro

  1555 W River Rd, Dummerston, VT 05301
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  /33

  $295,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  70 Overlook Dr, Londonderry, VT 05148

  Located close to town but in a private and quiet area, this property offers an affordable option for locals and first-time homebuyers who want to be in one of Vermont’s best little communities and are willing to make the time and investment to turn this house into a home. The house is solid and has been well-maintained, and there are three bedrooms and 1.5 bathrooms and a nice one-level layout

  Claudia Harris Mary Mitchell Miller Real Estate

  70 Overlook Dr, Londonderry, VT 05148
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  /8

  $48,000

  • Land
  • 6.1 Acres
  • $7,869 per Acre

  0 Cooke Rd, Brattleboro, VT 05301

  Amidst rolling VT farmland, sits these 6 acres in West Brattleboro. While there is road frontage on Rte 9, the driveway is off the class 4 section of Cooke Rd. There's about 250 feet of Cooke Rd that you would need to maintain before the town road. The ROW into the land parallels the power lines, which you cannot see when you're on the land. There a nice cleared shelf when you walk in and then

  Victoria Woods Brattleboro Area Realty

  0 Cooke Rd, Brattleboro, VT 05301
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  /23

  $3,500,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 7,000 Sq Ft

  29 Mountain Ridge Dr, Wilmington, VT 05363

  The Mountain Ridge community is newly developed and this is the first opportunity to enter this new prestigious location. 38 acres with 5 total lots, including a spectacular newly built luxury Timber Frame home being sold as-is near completion, with a builder on board ready to finish, plus 4 separate gorgeous mountain view building sites. Finish this home with the fixtures and finishes already

  Adam Palmiter Berkley & Veller Greenwood/Dover

  29 Mountain Ridge Dr, Wilmington, VT 05363
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  /12

  $249,000

  • Land
  • 19.6 Acres
  • $12,704 per Acre

  227 Gault Rd, Wardsboro, VT 05355

  This property is ready for you to push the pedal down and Go. All the engineering work has been done! There is an inground 3 bedroom septic system, a drilled well and a long gravel driveway with culverts.With almost half of the 19 acres being cleared, there is massive solar potential here for off the grid living. There is a large shed/cabin at the beginning of the driveway, which you could

  Victoria Woods Brattleboro Area Realty

  227 Gault Rd, Wardsboro, VT 05355
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  /15

  $20,000

  • 1 Bath
  • 407 Sq Ft

  152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356

  Quarter share (deeded interval 3) ownership at the Grand Summit offers 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. Experience the mountain resort lifestyle affordably!! This first floor (Unit 152) with a sleep four studio is 407 sq ft and has a Murphy bed in the living area, a kitchen/dining area, and a full bath. This unit is located on

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356
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  /43

  $619,900

  • 3 Beds
  • 3.5 Baths
  • 2,250 Sq Ft

  883 Smead Rd, Wardsboro, VT 05355

  Enjoy Vermont living in this bright and inviting 3-bedroom, 4-bathroom home, ideally located 7 minutes from Mount Snow and just under 20 minutes from Stratton. The open-concept kitchen (completely renovated in 2021) and dining area are perfect for gatherings, with natural light enhancing the home’s warm and welcoming feel.A new heating system for efficient year-round comfort is complemented by a

  Samantha Decker Deerfield Valley Real Estate

  883 Smead Rd, Wardsboro, VT 05355
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  /18

  $199,000

  • 2,139 Sq Ft

  34 Williams St, Bellows Falls, VT 05101

  Discover a superb investment or owner-occupant opportunity in the heart of downtown Bellows Falls, Vermont. This well-maintained two-story multi-family building offers two separate units, each featuring two bedrooms and one full bathroom. The property is dressed in durable vinyl siding for low-maintenance appeal and is fully insulated in the basement, exterior walls, and attic—enhancing energy

  Rob Weltz Barrett and Valley Associates Inc.

  34 Williams St, Bellows Falls, VT 05101
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  /41

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,091 Sq Ft

  798 Vermont Route 100, Wilmington, VT 05363

  Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  798 Vermont Route 100, Wilmington, VT 05363
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  /18

  $55,000

  • 3 Beds
  • 1.5 Baths
  • 924 Sq Ft

  78 Shady Pines Park, Westminster, VT 05158

  Looking for an affordable place to call home? This could be the place for you! This 1989 Mobile Home currently sits on a large, rented lot in the conveniently located Shady Pines Park in Westminster VT, close to I-91, and many surrounding towns like Bellows Falls, Saxtons River, and Walpole. The home features a large eat-in kitchen, 3 bedrooms, one and a half bathrooms, and the addition of a

  Chelsea Richardson Barrett and Valley Associates Inc.

  78 Shady Pines Park, Westminster, VT 05158
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  /56

  $475,000

  • 3,954 Sq Ft

  430 Hucklehill Rd, Vernon, VT 05354

  Welcome home! This inviting property offers the perfect blend of privacy and comfort. Nestled in a peaceful wooded setting, surrounded by classic stone walls and a year-round stream, this home provides the Vermont lifestyle you’ve been dreaming of! Inside, the main level features gleaming hardwood floors with radiant floor heat and an open-concept layout with vaulted ceilings. The bright kitchen

  Carol Slocum Keller Williams Realty Metro-Keene

  430 Hucklehill Rd, Vernon, VT 05354
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  /16

  $19,900

  • Land
  • 0.46 Acre
  • $43,261 per Acre

  00 Country Ct Unit 693, Wilmington, VT 05363

  Attention skiers, golfers, hikers, boaters, VAST lovers, and more! Discover the perfect blend of a country setting, amenities, and convenience with this exceptional land opportunity! This nearly half-acre lot is admirably located within Chimney Hill’s 1,200-acre private resort community with access to a wide range of recreational amenities for both summer and winter enjoyment. Located at the

  Casey Scott Southern Vermont Realty Group

  00 Country Ct Unit 693, Wilmington, VT 05363
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  /36

  $382,000

  • 6 Beds
  • 2.5 Baths
  • 3,590 Sq Ft

  88 Westminster St, Town of Rockingham, VT 05101

  Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 15 rooms, 6 bedrooms and the potential for 4 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period

  Jamie Watson BHG Masiello Keene

  88 Westminster St, Town of Rockingham, VT 05101
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  /33

  $390,000

  • 3 Beds
  • 1.5 Baths
  • 2,208 Sq Ft

  440 Stratton Arlington Rd, Stratton, VT 05360

  Experience the charm of owning a chalet in Vermont’s sought-after Stratton area, ideally located between Stratton Mountain and Mount Snow for easy ski access. Recent road improvements ensure smooth travel year-round. Outdoor lovers will enjoy nearby trails for hiking, snowmobiling, and snowshoeing, making this an ideal retreat for both relaxation and adventure. The home features a finished

  Mike England Michael England Real Estate

  440 Stratton Arlington Rd, Stratton, VT 05360
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  /39

  $312,000

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  15 Mountain Village Unit 234, West Dover, VT 05356

  Welcome to your mountain getaway! This 2-bedroom, 2-bath condo is perfectly situated at the base of Mount Snow. Enjoy your morning coffee or après-ski beverage on the private balcony while taking in the mountain air and breath taking views. Cozy up by the wood-burning fireplace, perfect for relaxing after a day on the mountain. Recent updates include new windows, slider doors, balcony, flooring

  Jillian Wimmelman Deerfield Valley Real Estate

  15 Mountain Village Unit 234, West Dover, VT 05356

Showing Results 41 - 80, Page 2 of 10