Windham County VT Homes under $300,000

• 

  

  

  /35

  $34,500

  • 2 Beds
  • 3 Baths
  • 1,026 Sq Ft

  316/318, QTR 1 89 Grand Summit Way, Dover, VT 05356

  The best ski-on/ski-off location in Mount Snow! This two-bedroom, three-bathroom loft unit, which sleeps 8, features both valley vista views from the living room and deck, and mountain views from the loft bedroom. Enjoy your own little piece of Vermont with family and friends. You own 13 weeks of vacation to use, rent, or trade! Year-round use of the Grand Summit amenities includes valet parking,

  Patricia Fitzpatrick Skihome Realty

  316/318, QTR 1 89 Grand Summit Way, Dover, VT 05356
• 

  

  

  /41

  $85,000

  • Land
  • 1.02 Acres
  • $83,333 per Acre

  402 Fox Mountain Rd, Wilmington, VT 05363

  Fantastic double lot on top of the Hill with recent soil tests and septic design suitable for your dream home! As Chimney Hill approaches full build out, the number of remaining lots are limited. This is a brand-new cul-de-sac adjoining the National Forest. Of the 5 lots, only two remain available, including this one. Time to stop imagining and start living the dream of your own vacation home.

  Sigrid Pickering Chimney Hill Realty

  402 Fox Mountain Rd, Wilmington, VT 05363
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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
• 

  

  

  /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
• 

  

  

  /11

  $149,000

  • 1 Bed
  • 1 Bath
  • 128 Sq Ft

  1 N Ridge Rd, Town of Rockingham, VT 05101

  Tiny home living in a big way! Enjoy the conveniences of public sewer and water on a quiet plot of land close to I-91 and five minutes to the Amtrack station. This property is well cared for and maintained. All you need to do is either move in or start renting it out for extra income. This adorable home generates over $20,000 per year as an Airbnb, or you can get up to $1500/mo in long term

  Amanda Cota The Thomas Group of Northern New England, LLC

  1 N Ridge Rd, Town of Rockingham, VT 05101
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  /24

  $299,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,192 Sq Ft

  1329 Newfane Rd, Wardsboro, VT 05355

  Nature lovers rejoice! Escape to the charm of rural Vermont with this rustic cottage retreat, privately set on a secluded 1-acre lot surrounded by woods and nature. Tucked away in a peaceful setting, this inviting home offers warmth, character, and the simple beauty of country living. The first floor features an open floor plan with hardwood floors and natural woodwork throughout, a cozy

  Matt Waddington Hoffman Real Estate

  1329 Newfane Rd, Wardsboro, VT 05355
• 

  /2

  $90,000

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft

  93 Clark St, Brattleboro, VT 05301

  An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only

  Christine Lewis Brattleboro Area Realty

  93 Clark St, Brattleboro, VT 05301
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  /2

  $50,000

  • Land
  • 28 Acres
  • $1,786 per Acre

  non Pikes Falls Rd, Jamaica, VT 05343

  This is a land locked parcel. There is no right of way or easement to access it. This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5%

  Carrie Mathews Winhall Real Estate

  non Pikes Falls Rd, Jamaica, VT 05343
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  /12

  $269,000

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

  333 US Route 5, Westminster, VT 05158

  Nestled on approximately nine plus acres in Westminster, Vermont, this charming three-bedroom, two-bathroom ranch-style home offers the perfect blend of privacy, comfort, and country living. Set back from Route 5, the property provides a peaceful retreat while remaining conveniently accessible. The expansive grounds feature mature fruit trees, open space for recreation or gardening, and

  Kassie Rubico Berkley & Veller Greenwood Country

  333 US Route 5, Westminster, VT 05158
• 

  

  /9

  $99,000

  $26K PRICE DROP

  • Land
  • 10.04 Acres
  • $9,861 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
• 

  

  /20

  $149,900

  • 4 Beds
  • 1.5 Baths
  • 2,200 Sq Ft

  22 Old River Rd, Bellows Falls, VT 05101

  Property being sold 'as is'. Recently repaired roof. Vermiculite insulation identified in second floor ceilings/attics. Seller has not occupied dwelling, so no SPIR or disclosures are available. This property is included in First Look program.

  Robert Balewicz Evergreen Realty of Vermont

  22 Old River Rd, Bellows Falls, VT 05101
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  /37

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  412 Western Ave, Brattleboro, VT 05301

  Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard—perfect for

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  412 Western Ave, Brattleboro, VT 05301
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  /18

  $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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  /20

  $149,000

  • Land
  • 24 Acres
  • $6,208 per Acre

  381 Whitaker Farm Rd, Marlboro, VT 05344

  24 improved acres in the hills of Marlboro offering a combination of privacy, accessibility, residential, and recreational potential. Recent driveway improvements have created excellent access into the property, leading to a cleared landing and potential building site set back from the road. Existing recreational and old logging trails meander throughout the acreage and are well-suited for

  Jacki Murano Southern Vermont Realty Group

  381 Whitaker Farm Rd, Marlboro, VT 05344
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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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  /32

  $19,250

  $11K PRICE DROP

  • 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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  /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
• 

  /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
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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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  /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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  /8

  $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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  /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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  /28

  $57,000

  $6K PRICE DROP

  • 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
• 

  

  /15

  $287,500

  • 4 Beds
  • 2 Baths
  • 1,472 Sq Ft

  66 Buckboard Dr, West Dover, VT 05356

  Off a quiet road, on a private lot, just a short drive from the Mount Snow ski resort and country village of Wilmington, sits this charming open concept chalet. Enjoy the best of both worlds with a true privacy on a level parcel, with private driveway and direct VAST snowmobile trail access, yet still near enough to the ski resort to pick up and go at a moments notice. Inside you are treated to a

  Adam Palmiter Berkley & Veller Greenwood/Dover

  66 Buckboard Dr, West Dover, VT 05356
• 

  

  /13

  $139,000

  • Land
  • 5 Acres
  • $27,800 per Acre

  14 Sugar Lot Ln, Jamaica, VT 05343

  Nestled in the heart of Jamaica, this pristine wooded lot offers a quintessential Vermont building canvas where privacy meets accessibility. As you pull off the quiet road onto the roughed-in driveway, you are immediately enveloped by a mature hardwoods that leads directly to a cleared homesite. This dedicated building envelope allows you to drive your car right to the center of your future

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  14 Sugar Lot Ln, 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
• 

  

  /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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  /5

  $150,000

  $25K PRICE DROP

  • 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
• 

  

  /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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  /9

  $249,000

  $46K PRICE DROP

  • Land
  • 54.8 Acres
  • $4,544 per Acre

  0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355

  Explore the potential of this beautiful 53.8-acre parcel just 3.5 miles from the scenic Townshend Dam. This expansive property offers a peaceful, wooded setting with ample privacy—ideal for recreation, a possible future homesite, or continued forest management. Currently enrolled in Vermont’s Current Use Program, the land offers significant tax savings and can remain in the program under new

  Carrie Mathews Winhall Real Estate

  0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
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  /19

  $68,900

  • Land
  • 21,780 Sq Ft
  • $137,800 per Acre

  Lot 1 - 161 High Peak Way, Wilmington, VT 05363

  Introducing Lot #1 in the High Peak Development, .50-acre double lot offering the foundation for your future Vermont home. This wooded parcel provides the peaceful setting of a cabin in the woods while still being just minutes from Mount Snow, The Hermitage Club, and the year-round recreation of the Deerfield Valley.With public sewer and public water access, the building process is made

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 1 - 161 High Peak Way, Wilmington, VT 05363
• 

  

  /29

  $19,500

  • 1 Bath
  • 332 Sq Ft

  218 Qtr.2 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Valley side unit includes: Queen murphy bed, kitchen, eating area, balcony and a full bath. 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

  Kelly Agrillo Southern Vermont Realty Group

  218 Qtr.2 89 Grand Summit Way, Dover, VT 05356
• 

  

  /18

  $250,000

  $30K PRICE INCREASE

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  5362 Us Route 5, Westminster, VT 05158

  BRAND NEW SEPTIC SYSTEM!! Move-in ready home, ideally situated in the heart of picturesque Westminster. This 3-bedroom, 1-bath home offers the perfect blend of charm, comfort and convenience. Step inside from the sunny, porch into a bright and functional kitchen featuring new countertops and easy access to the first-floor laundry area and recently renovated full bath. The layout flows seamlessly

  Karen Hoppe Berkley & Veller Greenwood Country

  5362 Us Route 5, Westminster, VT 05158
• 

  

  /20

  $79,500

  • Land
  • 13,939 Sq Ft
  • $248,438 per Acre

  Lot 2 - 162 High Peak Way, Wilmington, VT 05363

  Discover the perfect opportunity to build your Vermont retreat on this .32 acre lot in the High Peak Development, ideally positioned adjacent to the Haystack Golf Course. This wooded parcel offers the privacy of a cabin-in-the-woods setting while still being just minutes from Mount Snow, The Hermitage Club, and all the four season recreation the Deerfield Valley offers. Charming downtown

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 2 - 162 High Peak Way, Wilmington, VT 05363
• 

  

  /24

  $28,995

  • 2 Beds
  • 2 Baths
  • 745 Sq Ft

  304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units Studio unit (306) Queen murphy bed , kitchenette and full bathroom. Hotel unit (304) Two king beds and full bathroom. Units are located the valley side of the hotel . Lock out units has the benefit of using the unit as a whole or stay in one side and rent the other side out.

  Kelly Agrillo Southern Vermont Realty Group

  304/06 Qtr.2,89 Grand Summit Way, Dover, VT 05356

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