Windham County VT Homes for Sale

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  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  /43

  $1,975,000

  • 5 Beds
  • 4.5 Baths
  • 5,063 Sq Ft

  183 Old Mill Ln, Wilmington, VT 05363

  Breathtaking Lake and Vermont Forever Wild views from this 10 acre parcel overlooking Lake Whitingham, with deeded lake access. The premiere Old Mill Lane development is host to some of Wilmington's finest homes thanks to large private parcels, extended driveways, exclusive shared lake access and beach area with kayak rack, swimming cove, and easy access to the Village of Wilmington and nearby

  Adam Palmiter Berkley & Veller Greenwood/Dover

  183 Old Mill Ln, Wilmington, VT 05363
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  /45

  $1,475,000

  • 7 Beds
  • 6 Baths
  • 6,292 Sq Ft

  53 Hickory Ridge Rd, Putney, VT 05346

  Hickory Ridge House is a Federal masterpiece: a definitive piece of Vermont history. Elegant and expansive, the home’s soul is rooted in the 19th century, while its heart beats with 21st-century innovation. The interiors are a masterclass in "refined rustic" design, with original features such as antique wood floors, 12-over-12 windows, crown moldings, and wood-burning fireplaces throughout the

  Thomas Dahlin Berkley & Veller Greenwood Country

  53 Hickory Ridge Rd, Putney, VT 05346
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  /35

  $825,000

  • 3 Beds
  • 3.5 Baths
  • 1,730 Sq Ft

  2C Townhouse Square Unit 2, Dover, VT 05356

  Ski-in/ski-out living from this beautifully updated Seasons townhome, positioned trailside at Mount Snow. Stop in and out for meals or to check on pets, without ever taking off your boots. This well-appointed unit makes an immediate impression with its open-concept living space featuring soaring vaulted ceilings, a floor-to-ceiling stone chimney with wood-burning fireplace, and generous natural

  Adam Palmiter Berkley & Veller Greenwood/Dover

  2C Townhouse Square Unit 2, Dover, VT 05356
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  /38

  $1,850,000

  • 6 Beds
  • 6 Baths
  • 4,154 Sq Ft

  3 Slopeside Rd, West Dover, VT 05356

  Trailside luxury in a class of its own. This stunning home was taken down to the frame and should be considered new construction — positioned immediately trailside at Mount Snow with a private ski trail connecting directly to the magic carpet at Carinthia for full-season ski access. Ski to and from your mudroom door and never worry about shuttles or parking again.Professionally designed and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  3 Slopeside Rd, West Dover, VT 05356
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  /33

  $2,100,000

  • 7 Beds
  • 4 Baths
  • 4,256 Sq Ft

  121 Fannie Hill Rd, Wilmington, VT 05363

  Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  121 Fannie Hill Rd, Wilmington, VT 05363
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  /7

  $20,000

  • Land
  • 1.3 Acres
  • $15,385 per Acre

  0 Smead Rd Unit 5097619, Wardsboro, VT 05360

  Affordable opportunities to own land in Southern Vermont are becoming increasingly hard to find. This 1.30+/- acre wooded parcel on Smead Road offers a gradual rise from the road, creating a private, natural setting to enjoy now or explore for the future. Conveniently located between Mount Snow and Stratton, the property is close to year-round recreation, including skiing, snowmobiling, hiking,

  Jacki Murano Southern Vermont Realty Group

  0 Smead Rd Unit 5097619, Wardsboro, VT 05360
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  /29

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,272 Sq Ft

  12 Encore Place, Dover, VT 05356

  Mountain Modern Living with unmatched trail views of Carinthia at Mount Snow. Discover the perfect blend of luxury and nature in this 3 year young contemporary home ideally situated to capture breathtaking unobstructed views of the Mountain. This thoughtfully designed 4 bedroom home offers an open concept floor plan while still offering privacy and cozy spaces that highlight the beauty of the

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  12 Encore Place, Dover, VT 05356
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  /5

  $350,000

  $50K PRICE DROP

  • Land
  • 5.28 Acres
  • $66,288 per Acre

  0 Pond Rd, Town of Rockingham, VT 05346

  Looking for the dream land of your own, in town but outside of it? Look no further! With 5 acres of gently sloped woods there's plenty of space to site multiple building lots if you so wish, and with it abutting Minard's Pond nature area and just minutes from the village, there's plenty to do. Bring your dreams and plans, this might just be for you! Sale is subject to final survey & subdivision

  Courtney Doubleday EXP Realty

  0 Pond Rd, Town of Rockingham, VT 05346
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  /36

  $279,000

  $10K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 895 Sq Ft

  13 Snowtree Ln Unit Willows K, West Dover, VT 05356

  Just a short walk over bridge by Maples Building to the lifts at Mount Snow via the magic carpet, this stunning loft-style, fully remodeled Snowtree condo offers modern comfort and undeniable charm. The open-concept living area features vaulted ceilings, gleaming bamboo floors, and a cozy wood-burning fireplace. A glass slider leads to a private balcony overlooking a babbling brook and peaceful

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  13 Snowtree Ln Unit Willows K, West Dover, VT 05356
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  /2

  $59,900

  • Land
  • 1 Acre
  • $59,900 per Acre

  Lot 36 Woodsman Rd, Dover, VT 05356

  Super building lots up near the Dover Elementary School. Gentle sloping lots, with municipal sewer and underground telephone & electric. Prices reflect the quality of the view(s). Some with ski area(s) to the west and others with local ridgelines to south. Only moments from West Dover dining, shopping, and skiing. The Elementary School provides a fun campus for younger recreational fun. How many

  Michael Purcell Berkley & Veller Greenwood/Dover

  Lot 36 Woodsman Rd, Dover, VT 05356
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  /4

  $45,000

  • Land
  • 30 Acres
  • $1,500 per Acre

  00 Kidder Hill Rd, Grafton, VT 05146

  Invest in Vermont's forests and wildlife. This 30 acre wooded lot now available in Grafton. Entirety of parcel is enrolled in the Vermont Land Use program for forest management. Last cut was in 2020, plan update is required in 2028 with a projected next cut in approximately 2030. Topography does not offer typical residential building potential.

  Jessica Landers Barrett and Valley Associates Inc.

  00 Kidder Hill Rd, Grafton, VT 05146
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  /58

  $549,000

  $50K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  673 Vermont 121, Grafton, VT 05146

  Historic Charmer, this c. 1830 farmhouse has been loved and stewarded by its current owners for half a century. It is time to pass this amazing vintage home on to another lucky family. The house has original features including 2 fireplaces, curved plaster walls and beautiful honey colored wide pine floors. The first floor offers an eat-in- kitchen, formal dining room, spacious sunny living room

  Janet Lucier Barrett & Valley Assoc. Inc

  673 Vermont 121, Grafton, VT 05146
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  /24

  $275,000

  • 1 Bed
  • 1 Bath
  • 664 Sq Ft

  9 Mountain Village Unit 141, West Dover, VT 05356

  One of a kind 1 bedroom, 1 bath condo at Snow Mountain Village near the base of the Mount Snow ski resort. This gorgeous remodeled unit has all the style you would expect in a mountain retreat, with none of the headaches. Open concept space with a vaulted living room and kitchen, a wood burning fireplace, updated kitchen with ample storage and breakfast bar, updated furnishings, paint, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9 Mountain Village Unit 141, West Dover, VT 05356
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  /3

  $169,900

  • Land
  • 35.4 Acres
  • $4,799 per Acre

  0 Minard Rd, Westminster, VT 05346

  Over 35 wooded acres to call your own. Drive up the winding country road edged with meadows, views and a sense of peace to your own little haven. Spend some time on the land, scouting the views, finding the right site and falling in love with all the potential. Owned by the same family for over 30 years, it has finally come to market in just the right season to experience the golden glow of

  Christine Lewis Brattleboro Area Realty

  0 Minard Rd, Westminster, VT 05346
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  /27

  $199,595

  • Land
  • 4.2 Acres
  • $47,523 per Acre

  19 Stone Ridge Loop, Dover, VT 05356

  Located within the prestigious Village at Sawmill Farm, this exceptional homesite presents a rare opportunity to own in one of the Mount Snow Valley’s most sought-after communities. The extremely private property enjoys desirable southeasterly exposure with potential views of surrounding ridgelines, beautifully framed by timeless stone walls and majestic pines. A gentle slope makes it ideally

  Monique White Deerfield Valley Real Estate

  19 Stone Ridge Loop, Dover, VT 05356
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  /50

  $649,900

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  300 Route 121 E, Grafton, VT 05146

  Nestled in a postcard perfect riverfront setting in the picturesque village of Grafton, this exceptional 2002 contemporary home offers the rare blend of privacy, natural beauty, and convenience. Set on over two park like acres with frontage along the peaceful Saxtons River, the property delivers a true Vermont dream lifestyle.Inside, you’ll find a spacious eat in kitchen with abundant counter

  Gary Coger Four Seasons Sotheby's Int'l Realty

  300 Route 121 E, Grafton, VT 05146
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  /24

  $189,500

  • 2 Beds
  • 1 Bath
  • 893 Sq Ft

  1018 S Hill Rd, Jamaica, VT 05343

  OPEN HOUSE - Sunday 8/2, 1-3 ** BEST AND FINAL DEADLINE - Monday, August 3rd, 5pm. This charming A-frame offers a woodsy Vermont retreat on 2.8 acres on quiet and scenic South Hill Road. Set at the end of a long driveway and perched on a hill, surrounded by mature woods, this 2 bedroom, 1 bath home blends rustic character with a warm, inviting atmosphere. Natural wood flooring and wood features

  Prema Fitzpatrick Real Broker LLC

  1018 S Hill Rd, Jamaica, VT 05343
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  /31

  $260,000

  • 4 Beds
  • 2.5 Baths
  • 2,572 Sq Ft

  106 Coolidge Hwy Unit 6-276, Guilford, VT 05301

  Beautiful 1925 stucco Craftsman home needing TLC. Narrow strip oak flooring throughout, brick fireplace with original oak trim, original windows, beautiful oak staircase, arched doorways, dining room with enclosed porch, and a big country kitchen. There are many original features that make this property a great investment. The main house offers 2 sunny bedrooms; the adjacent finished apartment

  John Mcpherson Berkley & Veller Greenwood Country

  106 Coolidge Hwy Unit 6-276, Guilford, VT 05301
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  /9

  $85,000

  $30K PRICE INCREASE

  • Land
  • 1 Acre
  • $85,000 per Acre

  000F-320 Bourbon Run Rd, Jamaica, VT 05343

  This 1-acre wooded lot in Jamaica permitted for a 3 bedroom , Vermont offers a unique opportunity for peaceful living in a quiet town with no zoning restrictions. Jamaica maintains its own roads and is home to a State Park that provides excellent camping and summer recreational activities. The property is conveniently located near major ski resorts including Stratton, Bromley, Magic Mountain, and

  Mike England Michael England Real Estate

  000F-320 Bourbon Run Rd, Jamaica, VT 05343
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  /8

  $109,000

  $16K PRICE DROP

  • Land
  • 14.91 Acres
  • $7,311 per Acre

  0 Higley Hill Unit 5047164, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Package lot offers considered. Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill Unit 5047164, Dover, VT 05356
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  /36

  $22,500

  • 1 Bed
  • 1 Bath
  • 671 Sq Ft

  308 Qtr.4, 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

  308 Qtr.4, 89 Grand Summit Way, Dover, VT 05356
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  /44

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  85 Browns Rd, Newfane, VT 05345

  Steeped in Vermont history and surrounded by more than 80 acres of fields, woods, and walking trails, this beautifully preserved Newfane farmhouse offers the rare opportunity to own a property where timeless character and modern comfort come together. Whether you're looking for a full-time residence, country retreat, or recreational property, this is a place to slow down and enjoy the beauty of

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  85 Browns Rd, Newfane, VT 05345
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  /16

  $1,400,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,844 Sq Ft

  286 Coldbrook Rd, Wilmington, VT 05363

  This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf

  Melissa Nebelski Real Broker LLC

  286 Coldbrook Rd, Wilmington, VT 05363
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  /27

  $140,000

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft

  2074 Vt Rt 30, Jamaica, VT 05343

  Some places stop time. River's Edge is one of them.Step off the front door and onto a 10×12 covered porch shaded by old hemlocks, facing directly over the West River — away from the road, away from everything. The sound of moving water. The smell of the trees after rain. This porch is not an afterthought Brand new Lancaster Log Cabins "Sierra" Park Model. This 100% turn-key real log cabin

  Mike England Michael England Real Estate

  2074 Vt Rt 30, Jamaica, VT 05343
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  /39

  $349,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1 Frog Hollow, Wilmington, VT 05363

  Charming Rustic Country Saltbox on Lower Chimney HillNestled in a convenient Lower Chimney Hill location, this rustic country saltbox offers cozy comfort and classic Vermont charm. Featuring post-and-beam construction and a beautiful Pozzi wood-burning brick fireplace that keeps the house warmed right up, the home provides a warm and inviting atmosphere year-round.Outdoor enthusiasts will

  Rich Caplan Deerfield Valley Real Estate

  1 Frog Hollow, Wilmington, VT 05363
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  /6

  $329,000

  $9K PRICE DROP

  • Land
  • 47.58 Acres
  • $6,915 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of NH mountains & valleys. A super roadway already exists, providing access to places around the 47 private acres. Several places to build, affording long range views & glorious sunrises. Perfect location for that magical place you've been waiting to build. Ski area resort amenities are a short drive right around the corner, while Brattleboro & the CT River Valley

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
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  /12

  $125,000

  • Land
  • 15.6 Acres
  • $8,013 per Acre

  0 Thayer Rd, Westminster, VT 05158

  Rural 15.6 acre lot located at the end of Thayer Rd off Davidson Hill Rd in Westminster. This land is located in a quiet rural community on a gravel road about 10 minutes drive from Saxtons River Village and Bellows Falls Village. The lot consist of 3 lots of record all serviced by a common Right of Way. The ROW is also shared with a abutter to the north. The ROW provides ready to use access to

  Steve Schoppmeyer BHG Masiello Brattleboro

  0 Thayer Rd, Westminster, VT 05158
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  /20

  $99,500

  • Land
  • 10.27 Acres
  • $9,688 per Acre

  0 Theresa Ln, Wilmington, VT 05363

  This is a rare 10.27 acre offering located in the pastoral town of Wilmington, Vermont. Featuring approximately 8 acres open field, stone walls, cherry trees, potential views of the windmills with clearing, and the Beaver Brook running through the lower section, this property offers privacy and beauty. In addition, the land is close to Mount Snow and the Hermitage Club, plus provides easy access

  Lisa Mirando Deerfield Valley Real Estate

  0 Theresa Ln, Wilmington, VT 05363
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  /2

  $350,000

  $50K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to

  Christine Lewis Brattleboro Area Realty

  109 Central St, Brattleboro, VT 05301
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  /44

  $1,575,000

  $75K PRICE INCREASE

  • 5 Beds
  • 4 Baths
  • 4,099 Sq Ft

  314 Putnam State Forest Rd, Grafton, VT 05146

  Grafton Lodge is a striking five-bedroom, four-bathroom timber frame retreat set on 72 acres of complete privacy, directly bordering the 146-acre Putnam State Forest. Built in 2022, this 4,000+ sq ft home blends timeless craftsmanship with modern comforts, featuring wide hemlock floors, exposed beams, and walls of windows that invite the natural surroundings inside.At the heart of the home is

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  314 Putnam State Forest Rd, Grafton, VT 05146
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  /14

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  12 Autumn Gem Dr, Dummerston, VT 05301

  This affordable Dummerston home is tucked away on 11 private acres. Built with personal privacy in mind, the primary bedroom is on one end and the other 2 bedrooms and bath are at the other, eliminating hallways and adding to the living area. Warm yourself and save on fuel with the large pellet stove in the living room. Abundant light with the picture window in the front and skylight over the

  Christine Lewis Brattleboro Area Realty

  12 Autumn Gem Dr, Dummerston, VT 05301
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  /35

  $549,000

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  7 Lightning Ledge Way, Wilmington, VT 05363

  Located in the Chimney Hill community, this four-bedroom, two-bath home offers the perfect Southern Vermont retreat for every season. The open-concept living, kitchen, and dining area creates a welcoming space for gathering with family and friends after a day of skiing, boating, hiking, or exploring the area. Warm wood accents and comfortable living spaces create a relaxed Vermont atmosphere that

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  7 Lightning Ledge Way, Wilmington, VT 05363
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  /11

  $174,000

  • Land
  • 15 Acres
  • $11,600 per Acre

  491 Whitneyville Rd, Halifax, VT 05358

  Tucked away along a quiet, town-maintained deadend road, this private 15-acre parcel offers a rare combination of seclusion, character, and natural beauty. Set high on a peaceful knoll, the property features an old homesite's stone foundation, open meadow areas, and several mature apple trees that hint at the land’s past, also a drilled well.A gentle babbling brook traces one boundary, adding

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  491 Whitneyville Rd, Halifax, VT 05358
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  /41

  $1,498,500

  $252K PRICE DROP

  • 7 Beds
  • 5 Baths
  • 4,649 Sq Ft

  4669 Vermont Route 100, Londonderry, VT 05148

  Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with

  Story Jenks LandVest, Inc/Woodstock

  4669 Vermont Route 100, Londonderry, VT 05148
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  /48

  $1,650,000

  • 4 Beds
  • 3.5 Baths
  • 3,268 Sq Ft

  161 Depot Rd, Williamsville, VT 05362

  Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive 219-acre setting, showcasing a harmonious blend of nature and architecture. This

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  161 Depot Rd, Williamsville, VT 05362
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  /29

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 1,842 Sq Ft

  15B Snow Tree Ln Unit Clovers B, Dover, VT 05356

  Lovely updated townhome in the Snowtree development adjacent to the base area at Mount Snow. Take the Snowtree shuttle to the mountain or access via the walking bridge to the magic carpet at the tubing hill. If you don't ski you can still easily access the mountain without worrying about parking. Ideal for the ski season, but also summer festivals, hiking, biking, and more. Unlike the condos with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15B Snow Tree Ln Unit Clovers B, Dover, VT 05356
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  /10

  $129,000

  • Land
  • 2.1 Acres
  • $61,429 per Acre

  179 Oak Hill Rd, Wardsboro, VT 05353

  TWO LOTS, H-4 & H-13, you choose where to build, septic permits in place for both lots! Two, FOUR BEDROOM WASTEWATER PERMITS on file with the state one for each lot! Cleared lot on Maple with driveway installed, the other has been cut and could be ready to go easily! Don't miss this chance to own two abutting lots! Is being offered together or separate! See also MLS#5090072.

  Chris Lowe Lowe's Real Estate, LLC

  179 Oak Hill Rd, Wardsboro, VT 05353
• 

  

  /14

  $235,000

  • Land
  • 33.48 Acres
  • $7,019 per Acre

  0 Vt Route 100 Unit 5072614, Londonderry, VT 05155

  Beautiful 33.48 acre building lot in Londonderry. Some views possible and some clearing has been done. There are some wetlands on property but various choices for building sites exist. South East Facing

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  0 Vt Route 100 Unit 5072614, Londonderry, VT 05155
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  /48

  $479,000

  $20K PRICE DROP

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

  34 Johnson Hill Rd, Dover, VT 05356

  Recently repositioned with a price improvement, this move-in-ready chalet offers even greater value in one of Dover's most desirable mountain neighborhoods. Nestled on a corner parcel in the desirable Dover Hills area near Mount Snow, this beautiful chalet offers the perfect low-maintenance four-season retreat. Designed for easy upkeep and effortless enjoyment, the home combines warm mountain

  Donald Koelsch Deerfield Valley Real Estate

  34 Johnson Hill Rd, Dover, VT 05356

Showing Results 281 - 320, Page 8 of 12