Windham County VT Homes for Sale

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  $118,000

  • Land
  • 10.04 Acres
  • $11,753 per Acre

  Lot 2 North St, Dover, VT 05431

  Discover the perfect Vermont retreat on this 10.48 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 2 North St, Dover, VT 05431
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  /2

  $95,000

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft

  321 Williams St, Brattleboro, VT 05301

  Opportunity to live and invest in upgrades for your new home.

  Susan Bellville Bellville Realty

  321 Williams St, Brattleboro, VT 05301
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  /45

  $798,000

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  619 Stratton Arlington Rd, West Wardsboro, VT 05360

  Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  619 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /17

  $73,140

  • Land
  • 10,890 Sq Ft
  • $292,560 per Acre

  Lot 4 -156 High Peak Way, Wilmington, VT 05363

  Lot 4 in the High Peak Development, a .25-acre wooded parcel offering an ideal opportunity to create your own Vermont getaway. Perfectly situated just a short drive from Mount Snow, The Hermitage Club, and the recreational offerings of the Deerfield Valley, this lot provides the charm of a cabin in the woods setting with exceptional convenience.With public sewer and public water access,

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 4 -156 High Peak Way, Wilmington, VT 05363
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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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  /27

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,306 Sq Ft

  32 Old Town Rd, Dover, VT 05356

  Lovely mountain and sunset views from this absolutely immaculate home just south of the Mount Snow ski resort. Enjoy total privacy yet easy access to skiing, direct access to snowmobile trails, and nearby access to the villages of Wilmington and Dover for shopping and dining. The property consists of a level 2 acres with swimming pond, lawn space for summer fun, stone patio, storage shed, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  32 Old Town Rd, Dover, VT 05356
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  /54

  $999,000

  • 4 Beds
  • 4.5 Baths
  • 4,908 Sq Ft

  131 Stark Rd, Brattleboro, VT 05301

  Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, rolling meadows, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect location...minutes to town,

  Christine Lewis Brattleboro Area Realty

  131 Stark Rd, Brattleboro, VT 05301
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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

  $115,000

  • Land
  • 5 Acres
  • $23,000 per Acre

  0 Happy Haven Rd Unit 4998180, Wilmington, VT 05363

  Beautiful 5-Acre Lot with Mountain Views – Approved for Two Homes!Here’s your chance to own a truly special piece of Vermont! This gorgeous 5-acre parcel on Route 100, just north of Wilmington center, offers the perfect setting for your dream home—or two. Recent soil tests support the potential to build two single-family homes, each with up to three bedrooms. The land features an open,

  Monique White Deerfield Valley Real Estate

  0 Happy Haven Rd Unit 4998180, Wilmington, VT 05363
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  /26

  $395,000

  • 3,240 Sq Ft

  458 Williams St, Brattleboro, VT 05301

  458 Williams Street, formerly the WKVT headquarters, presents an opportunity for buyers exploring potential residential or mixed-use conversion in a convenient Brattleboro location. The 3,240 SF building is currently configured for office use across two levels, with more than 10 individual rooms, multiple bathrooms, and an existing kitchenette. This layout may lend itself to reconfiguration

  Neil Goldberg Brattleboro Area Realty

  458 Williams St, Brattleboro, VT 05301
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  /27

  $380,000

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  34 Main St, Wardsboro, VT 05355

  Lovely late 1800s farmhouse conveniently located in the village of Wardsboro, Vermont, just a short drive to both Mount Snow and Stratton ski resorts. Meticulously maintained, the home sits on a well-positioned parcel with ample parking, private lawn space, and direct snowmobile trail access, plus easy walking access to the nearby convenience store for everyday necessities. Inside, the home

  Adam Palmiter Berkley & Veller Greenwood/Dover

  34 Main St, Wardsboro, VT 05355
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  /2

  $129,900

  • Land
  • 3 Acres
  • $43,300 per Acre

  57 Cheney Brook Loop, Dover, VT 05356

  Rare 3 acre south facing parcel in an area of fine homes, an incredibly short distance from West Dover center dining, shopping, and golf & skiing. Yet, it is just off the paved main artery that provides access to Dover Hills. Plenty of room to provide buffering, a truly unusual offering that shouldn't be missed if you're interested in constructing what you can't find in a limited inventory

  Michael Purcell Berkley & Veller Greenwood/Dover

  57 Cheney Brook Loop, Dover, VT 05356
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  $19,250

  • 1 Bed
  • 1 Bath
  • 671 Sq Ft

  302 Qtr.1, 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

  Kelly Agrillo Southern Vermont Realty Group

  302 Qtr.1, 89 Grand Summit Way, Dover, VT 05356
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  $279,900

  • 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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  /9

  $250,000

  • Land
  • 3.79 Acres
  • $65,963 per Acre

  000 Fort Dummer Heights, Brattleboro, VT 05301

  Easy to build!!! The land is open, so no fuss with a lot of prep. Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

  Christine Lewis Brattleboro Area Realty

  000 Fort Dummer Heights, Brattleboro, VT 05301
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  /22

  $56,800

  • 3 Beds
  • 3 Baths
  • 1,323 Sq Ft

  157/265/267qtr3 Grand Summit Way Unit 157/265/267, Dover, VT 05356

  TRAILSIDE. Imagine the opportunity of owning a unit at the Grand Summit that can be used as studios that sleep 4, a 1 bedroom sleep 8 or even host 12 guests. Unit 157 sleeps 4 and has a sleep sofa and a Murphy bed, full kitchenette and a full bath. 157 connects via a flight of stairs to unit 267, another studio with a sleep sofa, Murphy bed, kitchenette and full bath, sleeps 4. Unit 265 has 2

  Sheila Joyce-Albano Skihome Realty

  157/265/267qtr3 Grand Summit Way Unit 157/265/267, Dover, VT 05356
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  $589,000

  • 3 Beds
  • 2.5 Baths
  • 2,782 Sq Ft

  628 Townshend Rd, Grafton, VT 05146

  One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

  Jessica Landers Barrett and Valley Associates Inc.

  628 Townshend Rd, Grafton, VT 05146
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  /35

  $2,399,000

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

  662 Howe Farm Rd, Jamaica, VT 05343

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

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  662 Howe Farm Rd, Jamaica, VT 05343
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  /13

  $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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  $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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  /58

  $865,000

  • 3 Beds
  • 4.5 Baths
  • 3,318 Sq Ft

  42 Sugar House Rd, West Dover, VT 05356

  Furnished mountain home in Mount Snow, Vermont.This custom crafted mountain home offers the ideal blend of rustic charm and modern comfort just minutes from Mount Snow and The Hermitage Club. Set on a private lot with winter views of both ski mountains, this 3-bedroom(+bonus bedroom), 4.5-bath home features an open-concept layout with soaring cathedral ceilings, exposed beams, and a stunning

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  42 Sugar House Rd, West Dover, VT 05356
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  $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
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  $799,000

  • 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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  $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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  $285,000

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

  70 Overlook Dr, Londonderry, VT 05148

  Welcome Home!!! 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

  Claudia Harris Mary Mitchell Miller Real Estate

  70 Overlook Dr, Londonderry, VT 05148
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  /3

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  2173 Vermont 8a, Whitingham, VT 05361

  4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

  Mark Yule BHG Masiello Brattleboro

  2173 Vermont 8a, Whitingham, VT 05361
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  $57,000

  • 2 Beds
  • 1 Bath
  • 844 Sq Ft

  2036 Vermont 30, Jamaica, VT 05343

  A cozy base for days spent enjoying Vermont country life warmed by a cozy wood stove and enjoying countless meals prepared together in the upgraded cherry and tile kitchen. Property has direct access to the West River. a nice deck to sit on in the back and a nice sitting platform overlooking river. Two bedroom one bath mobile home. Six months occupancy per year. New tenants must be approved by

  Mike England Michael England Real Estate

  2036 Vermont 30, Jamaica, VT 05343
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  /34

  $125,000

  • Land
  • 1.31 Acres
  • $95,420 per Acre

  118 Chimney Hill Rd, Wilmington, VT 05363

  Brand new Quad Lot right on Chimney Hill Road! Former lots M118 & M119 have had two additional parcels added on each end to form a 1.31-Acre Lot suitable for a three-bedroom single family home. Build your dream home and live the all-season resort lifestyle. Chimney Hill Owners Association is located on 1,200 acres adjacent to the Green Mt. National Forest, with 550 acres owned in common by the

  Sigrid Pickering Chimney Hill Realty

  118 Chimney Hill Rd, Wilmington, VT 05363
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  /32

  $27,000

  • 1 Bed
  • 2 Baths
  • 791 Sq Ft

  208/210 qtr2 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Unit 208 boasts a living dining area with a sleep sofa and a Murphy bed There is a full kitchenette including a stove, microwave, dishwasher and refrigerator. Unit 210 includes 2 queen size beds, minifridge and a deck. Use of the Grand

  Sheila Joyce-Albano Skihome Realty

  208/210 qtr2 89 Grand Summit Way, Dover, VT 05356
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  /51

  $879,900

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  7 Yodeling Ln, West Dover, VT 05356

  Charming Log Home with Modern Comfort and Prime Location. This warm and inviting log home offers the perfect blend of rustic charm and modern style. Nestled on a level lot with ample parking, it features a large covered front porch and a spacious rear deck, ideal for enjoying the beautiful outdoors. Step inside to the main level, where you'll find a welcoming living room anchored by a stunning

  Rich Caplan Deerfield Valley Real Estate

  7 Yodeling Ln, West Dover, VT 05356
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  /39

  $585,000

  • Land
  • 67.63 Acres
  • $8,650 per Acre

  932 Middle Rd, Dummerston, VT 05301

  Discover the perfect blend of peace, privacy, and potential on this 67.63-acre privately owned parcel of land. Nestled in a scenic and serene setting, this expansive property is a rare opportunity to build your dream home, estate, or getaway retreat. Two picturesque ponds – ideal for fishing, wildlife watching, or just enjoying the view. The main home site has amazing mountain views and sits atop

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  932 Middle Rd, Dummerston, VT 05301
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  $639,000

  • 4 Beds
  • 2.5 Baths
  • 2,573 Sq Ft

  11 Strawberry Hill, Brattleboro, VT 05301

  Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed

  Dan Normandeau Berkley & Veller Greenwood Country

  11 Strawberry Hill, Brattleboro, VT 05301
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  $529,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  19B Kingswood Rd, Dover, VT 05356

  Beautiful 3-bedroom, 3 bath Kingswood townhouse ideally located between Mount Snow and Hermitage Club. This Kingswood townhouse offers the perfect mountain getaway. Enjoy the well-appointed kitchen with a center island, a bright dining area, and a living area with a vaulted ceiling and a stunning 3 sided wood-burning fireplace, creating a warm, inviting atmosphere. Step outside onto a private

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  19B Kingswood Rd, Dover, VT 05356
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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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  /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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  /23

  $679,000

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

  14A Grouse Ln Unit 14A, Dover, VT 05356

  Gorgeous Post and Beam style townhome overlooking spectacular views of the Hermitage Club ski trails and sunsets over the ridgeline. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, easy nearby access to the Mount Snow ski resort, hiking and biking trails in the summer, and nearby convenience to the area's numerous lakes, dining and shopping.

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14A Grouse Ln Unit 14A, Dover, VT 05356
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  /5

  $150,000

  • Land
  • 23.4 Acres
  • $6,410 per Acre

  4125 Chester Hill Rd, Grafton, VT 05146

  Escape to nature at 4125 Chester Rd, Grafton, VT—a serene 23.4-acre retreat where peaceful living meets outdoor adventure. Enjoy the soothing sounds of Hall Brook as it winds through the property, perfect for quiet reflection and leisurely strolls. Embrace the winter wonderland with nearby snowmobile trails and take advantage of the location's proximity to Okemo Mountain for a variety of

  Jamie Watson BHG Masiello Keene

  4125 Chester Hill Rd, Grafton, VT 05146
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  /16

  $19,900

  • Land
  • 20,037 Sq Ft
  • $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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  /34

  $699,000

  • 3 Beds
  • 4 Baths
  • 3,796 Sq Ft

  233 Poverty Row, Whitingham, VT 05361

  What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, beautiful

  Adam Palmiter Berkley & Veller Greenwood/Dover

  233 Poverty Row, Whitingham, VT 05361
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  /33

  $229,000

  • 1 Bath
  • 475 Sq Ft

  11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356

  Discover effortless mountain living in this beautifully updated studio condominium that is walking distance to the slopes and in the desirable Snow Tree community. Perfect for weekend getaways, seasonal escapes, or as a high performing rental investment. This home boasts an extremely strong rental history supported by a documented 3 year history of over $25,000 annually and is being offered fully

  Melissa Ellis Southern Vermont Realty Group

  11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356

Showing Results 281 - 320, Page 8 of 9