Windham County VT Homes for Sale

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  /45

  $1,625,000

  • 15 Beds
  • 10 Baths
  • 12,845 Sq Ft

  4 Court St, Newfane, VT 05345

  A rare offering on the Newfane village green: a Federal-style inn dating to 1787, set beside the Windham County Courthouse along VT Route 30 in one of New England's most photographed villages. The property combines eight guest accommodations (a mix of multi-room suites and private rooms, each with a private bath) with a three-bedroom, two-bath owner's residence featuring its own full kitchen and

  Eben Viens Berkley & Veller Greenwood Country

  4 Court St, Newfane, VT 05345
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  /33

  $139,000

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

  185 Valley View Rd, Dover, VT 05256

  Rare opportunity to own a beautiful 5-acre wooded parcel in a peaceful country setting. Set back from the paved public road, this property offers privacy while remaining easily accessible year-round. A state Wastewater Permit for a 4-bedroom home is already in place, making it easy to begin planning your dream home or Vermont getaway. The land features a gentle, slightly sloping topography that's

  Chad Lackey Deerfield Valley Real Estate

  185 Valley View Rd, Dover, VT 05256
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  /5

  $250,000

  $20K PRICE DROP

  • 2,112 Sq Ft

  556 S Main St, Brattleboro, VT 05301

  New beginnings! Just right to live in one side, fix the other and have the tenant pay for your new lifestyle or have a family duplex and lie with extended family. the north side is vacant, needs renovation, and the south side has a tenant that will transfer with the building. Corner lot, yard, off street parking. Easy to see north unit, but otherwise a 48 hour notice to show.

  Christine Lewis Brattleboro Area Realty

  556 S Main St, Brattleboro, VT 05301
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  /14

  $249,999

  • Land
  • 29 Acres
  • $8,621 per Acre

  0 Stickney Brook Rd Unit 5101849, Dummerston, VT 05301

  Here's your chance to own 29 acres of wooded Vermont countryside with frontage on both Stickney Brook Road and Hopkins Road, offering flexible access and endless possibilities. Set along one of Dummerston's most picturesque country roads this unique parcel offers privacy, potential and the perfect setting for a private retreat, camp or future homesite. A mix of timber and classic New England

  Lily Gautot Greenwald Realty Group

  0 Stickney Brook Rd Unit 5101849, Dummerston, VT 05301
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  /16

  $259,900

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

  1270 Melendy Hill Rd, Guilford, VT 05301

  A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is a

  Christine Lewis Brattleboro Area Realty

  1270 Melendy Hill Rd, Guilford, VT 05301
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  /33

  $475,000

  $150K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft

  4448 Route 100, Wardsboro, VT 05355

  This four-bedroom, three-bathroom home with additional office or bonus room space can be yours! Offering a spacious family room with fireplace, a cozy den off the garage entry. A formal dining room in addition to kitchen that allows for another sitting area with plenty of wall space to decorate. The location is set back off Route 100, so very minimal road noise yet the highway is always

  Julie Lowe Lowe's Real Estate, LLC

  4448 Route 100, Wardsboro, VT 05355
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  /33

  $110,000

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  77 Hatch School Rd, Brattleboro, VT 05301

  Beautiful country setting! Manufactured home with addition located just off the pavement in Halifax, VT, rural yet central to VT Routes 9 & VT/MA 112 and the outlying towns of Guilford, Marlboro, Whitingham (Jacksonville), Wilmington and Dover, VT. The trustee seller has never occupied the home and has minimal information; financing may be limited due to the home pre-dating 1976. Shown by

  Stephanie Wilde

  77 Hatch School Rd, Brattleboro, VT 05301
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  /32

  $24,500

  • 1 Bed
  • 2 Baths
  • 869 Sq Ft

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

  This unique style, a sleep six condo, is located on the top floor of the hotel and features two levels, including a loft bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area has a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping four people. The spacious loft bedroom features a king-size bed, a large walk-in closet, and an

  Patricia Fitzpatrick Skihome Realty

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
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  /13

  $49,900

  $29K PRICE DROP

  • Land
  • 3.69 Acres
  • $13,523 per Acre

  0 Honeycomb Hill, Marlboro, VT 05301

  On the privately maintained road of Honeycomb Hill sits this 3.69 acre lot. The wooded parcel has young tree growth and slopes gently. There are three areas that are fairly level and open and may be suitable building sites. Just 30 minutes to Mt. Snow, 25 minutes to Brattleboro and 15 minutes to Harriman Reservoir, this conveniently located parcel offers easy access to all of Southern Vermont's

  Laura D'Angelo Berkley & Veller Greenwood Country

  0 Honeycomb Hill, Marlboro, VT 05301
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  /16

  $260,000

  • 1 Bed
  • 1 Bath
  • 512 Sq Ft

  319 River Rd S, Putney, VT 05346

  Looking for the simple life in tiny home living, or maybe just a good basecamp to explore the outdoors? Look no further! This unique property is conveniently located just a couple miles outside the bucolic village of Putney off a main road, with easy access to I-91. With 33 acres of rolling woods and local valley views there's plenty of land to explore and play with, while the cozy little home

  Courtney Doubleday EXP Realty

  319 River Rd S, Putney, VT 05346
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  /54

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,512 Sq Ft

  40 Ellis Brook Rd, West Dover, VT 05356

  Welcome to the beloved "Papa's Blue House," a cherished family home since its construction in 1968. Nestled in the desirable Dover Hills section of Dover, VT, this property offers the perfect blend of charm and potential. With good bones and a generous layout, it’s an ideal canvas for creating your dream home. Featuring a spacious open-concept living room, dining room, and kitchen, perfect for

  Donna Brown Skihome Realty

  40 Ellis Brook Rd, West Dover, VT 05356
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  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
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  /25

  $334,000

  $65K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  1511 E Dover Rd, Wardsboro, VT 05355

  Tucked along a scenic stretch of East Dover Road, this charming Wardsboro property captures the essence of Vermont country living with the added bonus of easy access to some of Southern Vermont’s most sought-after destinations. Just a short drive to Mount Snow and Stratton Mountain Resort, this location is ideal for year-round recreation from skiing and snowboarding in the winter to hiking,

  Mike Masters Four Seasons Sotheby's Int'l Realty

  1511 E Dover Rd, Wardsboro, VT 05355
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  /49

  $399,000

  $96K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  137 Stratton Arlington Rd, West Wardsboro, VT 05360

  Now Offered at $399,000! Exceptional Value Near Mount Snow & Stratton. Classic Vermont Home with Stunning Hilltop Views – Minutes from Mount Snow & Stratton. Set atop a peaceful New England hill, this classic Vermont home offers beautiful local and local mountain views in one of Southern Vermont's most desirable four-season locations. Just six miles from Mount Snow, Stratton Mountain, Grout Pond,

  Donald Koelsch Deerfield Valley Real Estate

  137 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /36

  $725,000

  • 5 Beds
  • 3 Baths
  • 2,427 Sq Ft

  95 Hemlock Dr, Londonderry, VT 05148

  The smell of woodsmoke on a crisp alpine afternoon, the quiet crunch of fresh powder underfoot, and the sense that the rest of the world has dropped away, this is the reality waiting at the top of Powder Mill Ridge. Tucked into three acres of private Vermont forest, this contemporary retreat is designed less like a standard house and more like a basecamp for a life well lived.Winters mean

  Robin Apps Four Seasons Sotheby's Int'l Realty

  95 Hemlock Dr, Londonderry, VT 05148
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  /3

  $450,000

  • Land
  • 3.38 Acres
  • $133,136 per Acre

  Lot 4 Mountain Ridge Estates, Wilmington, VT 05363

  Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 3.38+ acres overlooking the 18th tee box and mountains beyond for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot 4 Mountain Ridge Estates, Wilmington, VT 05363
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  /12

  $324,000

  New Construction $145K PRICE DROP

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

  442 Mcmillan Rd, Whitingham, VT 05342

  New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three levels.

  Mark Yule BHG Masiello Brattleboro

  442 Mcmillan Rd, Whitingham, VT 05342
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  /49

  $500,000

  • Land
  • 71 Acres
  • $7,042 per Acre

  00 Turkey Mountain Rd, Jamaica, VT 05343

  Escape to your own private 71-acre Vermont retreat, offering exceptional privacy and possibility plus access to nearby ski mountain villages. Tucked at the end of a town-maintained dead-end road and bordered on two sides by over 1,000 acres of conservation land, this property promises unmatched peace and lasting protection. Only 20 minutes to either Mt. Snow or Stratton, with over 3,300 feet of

  Jessica Landers Barrett and Valley Associates Inc.

  00 Turkey Mountain Rd, 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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  /41

  $999,000

  • 4 Beds
  • 4.5 Baths
  • 5,050 Sq Ft

  3 Shannon Ridge Rd, Dover, VT 05356

  Some homes are renovated. Others are carefully crafted. 3 Shannon Ridge Road is unmistakably the latter.At first glance, the home feels elegant. Spend time inside, however, & its character begins to emerge: 16-ft.-long wide pine floors secured w/ traditional square nails, remarkably high ceilings, beautifully composed architecture, expansive windows, live-edge wood, a kitchen for entertaining and

  Jacki Murano Southern Vermont Realty Group

  3 Shannon Ridge Rd, Dover, VT 05356
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  /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
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  /21

  $615,000

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  354 Orchard St, Brattleboro, VT 05301

  You don't have to wear pearls to live here! This home oozes classic charm, memories of Thanksgivings and every holiday celebrated. The first step in has a welcoming wood stove for winter chill and glass french doors to fling open the first day of spring....Bring them home to the heart of the house with a dining room big enough for a feast...living room with a fireplace....warm hardwood floors, a

  Christine Lewis Brattleboro Area Realty

  354 Orchard St, Brattleboro, VT 05301
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  /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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  /60

  $690,000

  • 5 Beds
  • 4 Baths
  • 2,642 Sq Ft

  57 Castle Hill Rd, Wilmington, VT 05363

  Welcome to "Pipe Dream", a cherished family vacation home for nearly two decades. This residence seamlessly blends history, charm, and modern touches to create a truly unique experience. The outdoor space of 3.5 acres is nothing short of magical, featuring stone walls and steps, an inviting in-ground pool, and a tennis court. The expansive level yard offers plenty of room for outdoor fun, while

  Donna Brown Skihome Realty

  57 Castle Hill Rd, Wilmington, VT 05363
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  /51

  $5,100,000

  • 10 Beds
  • 9.5 Baths
  • 6,648 Sq Ft

  15 Sawmill Rd, Stratton, VT 05155

  Location, Location, Location. Representing the pinnacle of Stratton Mountain trailside living, 15 Sawmill is a generational property where unrivaled ski-in/ski-out access creates one of Stratton's most exceptional legacy offerings. This is one of the few homes located along the trail - one you admire and wish was yours when you ski by it all winter season! Perfectly positioned directly on the ski

  Kim Morgan-Wohler Wohler Realty Group

  15 Sawmill Rd, Stratton, VT 05155
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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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  /60

  $6,898,000

  New Construction

  • 5 Beds
  • 8 Baths
  • 4,000 Sq Ft

  88 Mann Rd, Wilmington, VT 05363

  A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At

  Rich Caplan Deerfield Valley Real Estate

  88 Mann Rd, Wilmington, VT 05363
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  /3

  $500,000

  • Land
  • 1.82 Acres
  • $274,725 per Acre

  Lot 3 Mountain Ridge Estates, Wilmington, VT 05363

  Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.82+ acres overlooking the 18th fairway and mountains beyond for

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot 3 Mountain Ridge Estates, Wilmington, VT 05363
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  /11

  $125,000

  $24K PRICE DROP

  • 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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  /56

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,874 Sq Ft

  7 Cross St, Newfane, VT 05345

  This is your chance to be part of the historic and lively community in the center of Newfane.This home underwent a complete overhaul in the early 2000s, including a new slate roof, a relocated fireplace for a more practical layout, a reinforced stone foundation with a poured concrete floor, new windows, boiler, cement clapboard, and new kitchen countertops. The main level features radiant

  Victoria Woods Brattleboro Area Realty

  7 Cross St, Newfane, VT 05345
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  /33

  $249,000

  • 1 Bed
  • 468 Sq Ft

  246 Mann Rd, Wilmington, VT 05363

  Location, location, location! This rare opportunity is surrounded by the beautiful Haystack Golf Course, offering an unbeatable setting in one of southern Vermont's premier resort destinations. The property currently features a camp and a one-car garage, allowing you to enjoy the land immediately while planning your dream home or future getaway. Just minutes from Mount Snow, The Hermitage Club,

  Jeffrey Brisson Cohn & Company

  246 Mann Rd, Wilmington, VT 05363
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  /25

  $287,900

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  17 Willis Rd, Wilmington, VT 05363

  Enjoy the best of Southern Vermont from this spacious and inviting condo, offering a wonderful blend of comfort, convenience, and privacy. Ideally located just a short drive from Mount Snow and downtown Wilmington, this property is perfectly suited as a year-round retreat or four season vacation home. The open concept second floor offers an effortless flow between the kitchen, dining, and living

  Meghan Buckley Skihome Realty

  17 Willis Rd, Wilmington, VT 05363
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  /50

  $250,000

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  147 Morningside Dr, Brattleboro, VT 05301

  Easy living. This move-in-ready townhouse comes with snow removal; trash, recycling and compost removal; landscaping; a swimming pool; tennis and pickleball courts; a hiking trail and little libraries included. The seller has refurbished the entire unit by installing beautiful flooring on the first floor and in bathrooms, refinishing cabinets, painting, and cleaning carpeting in order to get the

  Sally Fegley BHG Masiello Brattleboro

  147 Morningside Dr, Brattleboro, VT 05301
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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
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  /33

  $499,000

  • 2 Beds
  • 2 Baths
  • 3,320 Sq Ft

  5855 Windham Hill Rd, West Townshend, VT 05359

  Bring your vision to life on 33.34 acres in the scenic hills of Windham, Vermont. This partially completed home offers a rare opportunity to finish a thoughtfully designed residence surrounded by open meadows, established trails, and an idyllic rural setting.Designed with a 4 bedroom septic system, the home is ready for the next owner to complete the interior and exterior finishes. The

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  5855 Windham Hill Rd, West Townshend, VT 05359
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  /23

  $395,000

  $30K PRICE DROP

  • Land
  • 133 Acres
  • $2,970 per Acre

  40 E Putney Brook Rd, Putney, VT 05346

  Motivated Sellers! Rare opportunity to own 133 +/- acres of Vermont land near the village of Putney, Vermont. Whether you are seeking a residential retreat, recreational escape, hunting terrain or exploring subdivision/development opportunities, this property offers exceptional possibilities. The 133+/- acres is pleasantly interrupted by the East Putney Brook and offers 3 points of access,

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  40 E Putney Brook Rd, Putney, VT 05346
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  /33

  $1,450,000

  $200K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 4,443 Sq Ft

  874 Middletown Rd, Grafton, VT 05146

  Set along picturesque Middletown Road, just beyond the historic village of Grafton, this elegant five-bedroom residence enjoys a setting that feels both timeless and deeply peaceful. Perhaps it is the pleasing symmetry and classic proportions of the c.1815 brick Federal home with its Georgian floor plan. Perhaps it is the views of rolling meadows and rounded hills that unfold in both directions.

  Story Jenks LandVest, Inc/Woodstock

  874 Middletown Rd, Grafton, VT 05146
• 

  

  /48

  $599,000

  $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  774 Stratton Arlington Rd, Stratton, VT 05360

  Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  774 Stratton Arlington Rd, Stratton, VT 05360
• 

  

  /12

  $67,500

  • Land
  • 3.5 Acres
  • $19,286 per Acre

  0 Dover Rd Unit 5102886, Newfane, VT 05345

  Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that your new home

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  0 Dover Rd Unit 5102886, Newfane, VT 05345
• 

  

  /23

  $250,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  429 Vt Route 30, Newfane, VT 05345

  Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  429 Vt Route 30, Newfane, VT 05345

Showing Results 361 - 400, Page 10 of 12