Windham County VT Homes for Sale

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  /26

  $385,000

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

  48 Villager Loop, West Dover, VT 05356

  What a find! This well-maintained 3-bedroom plus den home in the Dover Hills is the perfect year-round Vermont getaway. Just 10 minutes to Mount Snow, you’ll have easy access to world-class skiing and riding in winter and scenic lift-served mountain biking in summer. With a first-floor bedroom and laundry, it’s designed for ease and convenience. Stay cozy with the pellet stove in winter, and cool

  Patrice Schneider Southern Vermont Realty Group

  48 Villager Loop, West Dover, VT 05356
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  /11

  $250,000

  • Land
  • 18 Acres
  • $13,889 per Acre

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

  Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

  Christine Lewis Brattleboro Area Realty

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
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  /46

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,960 Sq Ft

  16 Springhill Rd, Dover, VT 05356

  Experience modern luxury in this stunning contemporary home, less than 10 minutes from Mount Snow and just 15 minutes from The Hermitage Club. This thoughtfully designed retreat offers both sophistication and comfort, with high-end finishes and exceptional craftsmanship throughout. You will be captivated by the soaring freestanding stone fireplace, which serves as the heart of the home, complete

  Patrice Schneider Southern Vermont Realty Group

  16 Springhill Rd, Dover, VT 05356
• 

  

  

  /51

  $899,800

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
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  /35

  $34,900

  • 1 Bed
  • 2 Baths
  • 745 Sq Ft

  341/43 Qtr.4,89 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 (341) Queen murphy bed, kitchenette, full bathroom . Hotel unit (343) Two king beds, full bathroom. Units are located on the third floor mountain side of the hotel. Lock out units have the benefit of using the unit as a whole or stay in one side and rent the other

  Kelly Agrillo Southern Vermont Realty Group

  341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356
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  /43

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 2,872 Sq Ft

  1587 Upper Holbrook Rd, Whitingham, VT 05361

  Set on 3 beautiful acres, this well-maintained 3-bedroom plus loft, 2 1/2 bath home is truly move-in ready. Enter through a spacious mudroom with a convenient back opening for bringing in firewood for the cozy wood stove in the living room. The open-concept kitchen and dining area provide plenty of room for entertaining, while a den/game room just off the living room with a bar area (4X8) offers

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1587 Upper Holbrook Rd, Whitingham, VT 05361
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  /22

  $199,000

  • Land
  • 3.6 Acres
  • $55,278 per Acre

  00 Lake Hill Rd Unit "Spring Lot", Whitingham, VT 05361

  Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing showing positive results, utilities at the road,

  Chad Lackey Deerfield Valley Real Estate

  00 Lake Hill Rd Unit "Spring Lot", Whitingham, VT 05361
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  /60

  $1,255,000

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  136 Yeaw Rd, Dover, VT 05341

  This is the perfect Vermont getaway, private and secluded, minutes from skiing, restaurants, and all the charm of Southern Vermont. This property is truly special, set on landscaped grounds with rolling meadows, a small, renovated barn with deck, and a 30x40 insulated Q Building with heat, water and 220 amps, as well as a whole house generator.The location is choice: close to world-class

  Amy Carson Lowe's Real Estate, LLC

  136 Yeaw Rd, Dover, VT 05341
• 

  

  /20

  $469,000

  • 4 Beds
  • 2 Baths
  • 2,219 Sq Ft

  45 Dover Hill Rd, East Dover, VT 05341

  Recently renovated 1900s Colonial just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access off a paved town road. This cozy Vermont retreat sits on 3+ acres with established trails, a gurgling brook wrapping around the home, bridge to access the rear upper meadow, perennial landscaping, and more. The home is being offered

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Dover Hill Rd, East Dover, VT 05341
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  /8

  $65,000

  • Land
  • 2 Acres
  • $32,500 per Acre

  585 Sawmill Rd, Stratton, VT 05360

  Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway. Association

  Carrie Mathews Winhall Real Estate

  585 Sawmill Rd, Stratton, VT 05360
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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
• 

  

  /10

  $199,000

  • Land
  • 23.1 Acres
  • $8,615 per Acre

  184 Dupre Dr, Guilford, VT 05301

  Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

  A.J. Bellville Bellville Realty

  184 Dupre Dr, Guilford, VT 05301
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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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  /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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  /60

  $579,000

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft

  794 White Rd, Windham, VT 05359

  Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

  Erica Reynolds Southern Vermont Realty Group

  794 White Rd, Windham, VT 05359
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  /2

  $145,000

  • Land
  • 2.9 Acres
  • $50,000 per Acre

  00 W River Rd, Brattleboro, VT 05301

  A 2.9 acre build-able lot in Brattleboro's Waterfront District, on heavily-trafficked Route 30, next to the well-loved Fire Arts' building. There are many allowed and conditional uses for this zoning, including Residential, Retail, Marina, Fitness, Art Gallery and more. A great location for your new business, with great visibility to over 1500 cars daily.

  John Hatton Berkley & Veller Greenwood Country

  00 W River Rd, Brattleboro, VT 05301
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  /54

  $619,000

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  87 Townshend Rd, Grafton, VT 05146

  Welcome home to The Woodard House, a light-filled, historic home in the heart of beautiful Grafton, Vermont. Just a stroll from the Grafton Inn, Phelps Barn Pub, Nature Museum, dining options, and recreation, the spacious, historic home offers exceptional appeal for personal use or as a proven short-term rental. Available fully furnished for a seamless transition, it’s ready to welcome guests or

  Erin McCormick KW Vermont

  87 Townshend Rd, Grafton, VT 05146
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  /21

  $25,500

  • 1 Bed
  • 2 Baths
  • 709 Sq Ft

  243/245 qtr 2, Grand Summit Way Unit 243/245, Dover, VT 05356

  TRAILSIDE! A great and affordable opportunity to own the best location to be on the Mount Snow ski trails. Unit 243 boast a queen size Murphy bed, kitchenette and full bath. This unit sleeps 2 and has amazing views of the mountain. Unit 245 has 2 queen beds a full bath, a mini fridge and a private deck overlooking the ski trails. This lockout combination allows you to use the studio and the hotel

  Sheila Joyce-Albano Skihome Realty

  243/245 qtr 2, Grand Summit Way Unit 243/245, Dover, VT 05356
• 

  

  /3

  $125,000

  • Land
  • 1.75 Acres
  • $71,429 per Acre

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301

  Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what morecould you want? Easy to build!!! The land is open, so no fuss with a lot of prep. 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

  Christine Lewis Brattleboro Area Realty

  0 Fort Dummer Heights Unit 4934976, Brattleboro, VT 05301
• 

  

  /60

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  8 Little Bend Unit M-175, Wilmington, VT 05363

  Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Haven is a short walk to the Clubhouse, at the end of the road, with a wood burning fireplace, family room, open concept living, dining and kitchen, with deck, and three levels of living and sleeping spaces. Main level has a mudroom for gear, bedroom and full bath, kitchen/dining, deck with a babbling brook

  Sigrid Pickering Chimney Hill Realty

  8 Little Bend Unit M-175, Wilmington, VT 05363
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  /36

  $799,000

  • 3 Beds
  • 3.5 Baths
  • 2,842 Sq Ft

  43C Dover Springs Ln, Dover, VT 05356

  This Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A meticulously maintained 3 bedroom, 3.5 bath unit with lots of bonus space, some recent updates and unique features. These include an open concept great room with vaulted ceilings, sunny natural light and sunset/ski trail views, wood burning double sided fireplace,

  Adam Palmiter Berkley & Veller Greenwood/Dover

  43C Dover Springs Ln, Dover, VT 05356
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  /27

  $24,900

  • 1 Bed
  • 2 Baths
  • 941 Sq Ft

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

  This one-of-a-kind unit-style is on one level and includes one bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area features a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping six people. The spacious bedroom includes a king-size bed and a balcony with beautiful ridgeline views. The benefits of Grand Summit ownership

  Patricia Fitzpatrick Skihome Realty

  230, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
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  /6

  $45,000

  • Land
  • 1 Acre
  • $45,000 per Acre

  0 Boardman Loop, Wardsboro, VT 05360

  In the Heart of it all! This affordable acre of land is close to skiing, hiking, ponds and all the good stuff Vermont has to offer. Electric poles are across the street and the neighbors are hooked up. Starlink and Xfinity charts say they service the area for at home work, streaming or game playing. There are Covenants attached for the after midnight reading. There is a small stream on the

  Christine Lewis Brattleboro Area Realty

  0 Boardman Loop, Wardsboro, VT 05360
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  /28

  $499,000

  • 5 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  47 Ives Rd, Wilmington, VT 05363

  Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

  Adam Palmiter Berkley & Veller Greenwood/Dover

  47 Ives Rd, Wilmington, VT 05363
• 

  

  /11

  $245,000

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  3C Snow Mountain Village Unit 113, Dover, VT 05356

  Showings to start 1/12/26. The special assessment on this unit has been paid in full! Don’t miss out on this incredible opportunity to own a cozy mountain getaway at Snow Mountain Village! This beautifully updated 1 bed, 1 bath condo offers the perfect balance of comfort and convenience. With breathtaking mountain views right from your first-floor patio, you can relax and enjoy the natural beauty

  Carrie Mathews Winhall Real Estate

  3C Snow Mountain Village Unit 113, Dover, VT 05356
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  /35

  $39,000

  • 2 Beds
  • 2 Baths
  • 914 Sq Ft

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

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Mountainside two bedroom sleep 6 unit with a covered balcony. Kitchen, living room with a queen sleeper sofa. The lofted bedroom and private bedroom both have king beds. Full bath with double sink vanity on the first floor and a 3/4 bath on the second floor. Benefits of Grand Summit ownership include the best ski in/out

  Kelly Agrillo Southern Vermont Realty Group

  311 Qtr.2, 89 Grand Summit Way, Dover, VT 05356
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  /39

  $849,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  101 North Rd, Wilmington, VT 05363

  Stunning new construction in the Chimney Hill community just outside the village of Wilmington, and a short drive to both the Mount Snow ski resort, Hermitage Club, and Lake Whitingham. Located on an easily accessible corner lot in the desirable B section at the bottom of the hill with unique double lot size allowing for tremendous expansion potential . This home was built sparing no expense and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  101 North Rd, Wilmington, VT 05363
• 

  

  /31

  $947,000

  • 5 Beds
  • 3 Baths
  • 3,015 Sq Ft

  100 Mowing Way, Wilmington, VT 05363

  Impeccably maintained golf course home nestled in the Vermont mountains just 5 miles from lakes, ski resorts, and scenic trails. Perfect for entertaining or quiet enjoyment, this elegant property combines luxury and comfort in a stunning natural setting. The soaring great room features beamed ceilings, radiant heated hickory floors, and a gas fireplace flanked by built ins. A chefs dream kitchen

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  100 Mowing Way, Wilmington, VT 05363
• 

  

  /5

  $65,000

  • Land
  • 5.1 Acres
  • $12,745 per Acre

  212 S Pine Banks Rd, Putney, VT 05346

  Lovely 5.1 acre building site in Putney Vermont with easy access to downtown and Rte 91. This level building site was partially cleared in 2017 and has a 12x16 shed on it at present. There was a prior perc test and approved sites for septic and well that would need to be updated. Despite being overgrown at present, with a little work this could be a lovely spot for a private home site in a great

  Adam Palmiter Berkley & Veller Greenwood/Dover

  212 S Pine Banks Rd, Putney, VT 05346
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  /35

  $2,197,000

  • 5 Beds
  • 4.5 Baths
  • 5,110 Sq Ft

  14 Tarheel Trail, Wilmington, VT 05363

  This custom built 2018 log home, designed by RH Log Works and Hilderbrand Interiors, offers the ultimate in sophistication and luxury. Featured in Better Homes and Gardens, New England Home and Country Home magazines, this 5 bedroom, 4.5 bathroom sanctuary (plus extra bunk room) is nestled on 2.2 wooded acres with a river running alongside. Just 4 minutes from Hermitage Club and 10 minutes from

  Adam Palmiter Berkley & Veller Greenwood/Dover

  14 Tarheel Trail, Wilmington, VT 05363
• 

  

  /40

  $1,695,000

  • 7 Beds
  • 7.5 Baths
  • 8,364 Sq Ft

  251 Pratt Bridge Rd, Jamaica, VT 05343

  Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

  TG Glazer Winhall Real Estate

  251 Pratt Bridge Rd, Jamaica, VT 05343
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  /47

  $999,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  151 Holland Rd, Dover, VT 05341

  An outdoor enthusiast’s dream retreat! This breathtaking 92.6-acre Vermont sanctuary is a paradise for nature lovers, equestrians, and adventurers alike. The property features rambling stone walls, lush gardens, cherry trees, blueberry bushes, rolling pastures, woodlands, babbling brooks, a serene pond, and miles of scenic trails. The charming, open-concept, four-bedroom Cape includes a

  Patrice Schneider Southern Vermont Realty Group

  151 Holland Rd, Dover, VT 05341
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  /16

  $22,000

  • 1 Bath
  • 407 Sq Ft

  121 Qtr 4 89 Grand Summit Way Unit 121, Dover, VT 05356

  Quarter share (deeded interval 4) 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 121) 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

  121 Qtr 4 89 Grand Summit Way Unit 121, Dover, VT 05356
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  /18

  $1,145,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  80 Banning Rd, Putney, VT 05346

  Rare offering on Putney Mountain! Spectacular house site with new foundation and great Southern exposure awaits your vision! Includes four bedroom septic system, and drilled well. Create your new home with the included framing lumber and your team of craftsmen. House is sited in a private location, yet is accessible to the town road via an easily maintained level driveway. Additional

  David White OwnerEntry.com

  80 Banning Rd, Putney, VT 05346
• 

  /2

  $64,900

  • Land
  • 3.65 Acres
  • $17,781 per Acre

  Lot 18 Central Park Estates, Vernon, VT 05354

  3.65 acre building lot in a quiet rural setting in Vernon. Bypass the housing shortage, construct your own dream house. This is near Vernon's popular recreation center, home to home to a swimming pool, tennis courts, basketball courts, playground, and picnic area. Lily Pond is also nearby, a 40-acre body of quite shallow water with many varieties of birds and plants.

  John Hatton Berkley & Veller Greenwood Country

  Lot 18 Central Park Estates, Vernon, VT 05354
• 

  

  /48

  $32,000

  • 1 Bed
  • 2 Baths
  • 846 Sq Ft

  226/228, Qtr 2 Grand Summit Way Unit 226/228, 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 and features 2 full baths, a kitchen/dining area, and stunning valley views. Unit 226 is a

  Donna Brown Skihome Realty

  226/228, Qtr 2 Grand Summit Way Unit 226/228, Qtr 2, Dover, VT 05356
• 

  

  /12

  $325,000

  • Land
  • 3.42 Acres
  • $95,029 per Acre

  2366 Middletown Rd, Landgrove, VT 05148

  This property is within walking distance to the village of Londonderry and overlooks the town from its location approximately 500 paces up the hill on Middletown Road. The lot encompasses a hill that gives it privacy and security. Spring water flows to the base of the hill at one end of the propertyThe village commercial zoning gives the site options for multiple residential units (condos?),

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  2366 Middletown Rd, Landgrove, VT 05148
• 

  

  /38

  $1,600,000

  • 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
• 

  

  /32

  $1,697,000

  • 4 Beds
  • 3 Baths
  • 2,420 Sq Ft

  197 Lake Raponda Rd, Wilmington, VT 05363

  This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by

  Adam Palmiter Berkley & Veller Greenwood/Dover

  197 Lake Raponda Rd, Wilmington, VT 05363
• 

  

  /24

  $20,000

  • 1 Bed
  • 2 Baths
  • 840 Sq Ft

  89 236 Qtr. 2 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

  89 236 Qtr. 2 Grand Summit Way, Dover, VT 05356

Showing Results 81 - 120, Page 3 of 10