Windham County VT Homes for Sale

• 

  

  

  /43

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,812 Sq Ft

  1 Bucket Ln, Dover, VT 05356

  Classic chalet tastefully renovated by the current owner, blending rustic charm with thoughtful modern updates. The open-concept floor plan features vaulted ceilings and exposed beams throughout the main living area. A stunning floor-to-ceiling brick fireplace with wood stove insert anchors the spacious kitchen, living and dining areas, which open to an expansive deck perfect for entertaining.

  Linda Benoit Highland Realty

  1 Bucket Ln, Dover, VT 05356
• 

  

  

  /7

  $399,000

  • Land
  • 30 Acres
  • $13,300 per Acre

  Lot X Tyanoga Rd, Whitingham, VT 05361

  Spectacular opportunity to own a rare waterfront building lot on Lake Sadawga in Southern Vermont. This lot sits on a private dead end corner with southern exposure, private lake frontage including an earthen dam, and easy access along this pristine, natural lake. There is additional frontage along Stimpson Hill Road. The lake offers tremendous fishing, kayaking, canoeing, water sports, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot X Tyanoga Rd, Whitingham, VT 05361
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  /43

  $747,500

  • 5 Beds
  • 3.5 Baths
  • 3,436 Sq Ft

  67 Castle Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completely turnkey with extensive updates, thoughtful renovations, and modern amenities throughout. Ideally located just outside the country village of Wilmington for shopping and dining, a short drive to Mount Snow, and just up the street from Lake Whitingham’s boat launch and beach areas — truly four-season

  Adam Palmiter Berkley & Veller Greenwood/Dover

  67 Castle Hill Rd, Wilmington, VT 05363
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  /37

  $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
• 

  

  

  /52

  $549,000

  • 3 Beds
  • 2 Baths
  • 2,697 Sq Ft

  193 Rt 9 E, Wilmington, VT 05363

  Step into a piece of Wilmington history with this captivating 3+ bedroom, 2-bath Cape set on a picturesque 1-acre parcel just beyond Wilmington Village. Built in 1920 by Martin Brown, this former “Playhouse” of Beaver Brook Farm (AKA White House of Wilmington) blends timeless character with thoughtful modern updates. The heart of the home is a magnificent open-concept kitchen, living, and dining

  Chad Lackey Deerfield Valley Real Estate

  193 Rt 9 E, Wilmington, VT 05363
• 

  

  /57

  $850,000

  • 5 Beds
  • 4 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

  Mike England Michael England Real Estate

  4880 Pikes Falls Rd, Jamaica, VT 05343
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  /46

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 2,353 Sq Ft

  2416 Stage Rd, Guilford, VT 05301

  A truly magical setting! If you've never experienced the blissfulness of the Green River Village and its historic covered bridge and crib dam/waterfall and one of the most spectacular swimming holes imaginable, it's a must visit southern Vermont destination. Nestled in this picturesque valley village is this charming old home privately situated on 53.5 acres only a short stroll up the driveway

  Chris Long BHG Masiello Brattleboro

  2416 Stage Rd, Guilford, VT 05301
• 

  

  /40

  $825,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Imagine 216 acres of rolling fields, serene woodlands, and a glowing sugarbush tucked along a quiet country dirt road near the Massachusetts border in Halifax, just a short drive to Brattleboro and Wilmington. Held by the same family for generations, this timeless Southern Vermont property includes a farmhouse, barns, and several outbuildings—many ready for restoration, reimagining, or

  Melissa Nebelski Real Broker LLC

  6036 Jacksonville Stage Rd, Guilford, VT 05301
• 

  

  /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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  /32

  $1,975,000

  • 4 Beds
  • 3 Baths
  • 3,212 Sq Ft

  74 N Brookwood Rd, Stratton, VT 05360

  PRIME LOCATION near the coveted STRATTON MOUNTAIN RESORT. This EXCEPTIONAL four bedroom three bathroom turn-key home is PRIVATELY SITUATED on 1.5 acres and READY TO BE ENJOYED YEAR ROUND. Snowmobile right from the house to access thousands of acres of pristine VAST snowmobile trails for ENDLESS WINTER ADVENTURE. Ski home to the Covered Bridge neighborhood or hop on the resort shuttle, which runs

  Paul Marino WWW.FLATFEEMLS4FREE.COM

  74 N Brookwood Rd, Stratton, VT 05360
• 

  

  /33

  $489,000

  • 4 Beds
  • 2 Baths
  • 2,070 Sq Ft

  18 Quail Ct, Wilmington, VT 05363

  Spacious ski chalet in the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. Just down from the rec center and clubhouse sits this well maintained home with easy access, ample parking, a level back yard, and nice privacy, yet with all the conveniences of community living. The interior has a vaulted open concept living space with natural light and large

  Adam Palmiter Berkley & Veller Greenwood/Dover

  18 Quail Ct, Wilmington, VT 05363
• 

  

  /31

  $599,000

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  48 Upper Highlands, Dover, VT 05356

  Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning fireplace, natural woodwork and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48 Upper Highlands, Dover, VT 05356
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  /28

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  49 West Rd, Wilmington, VT 05363

  Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  49 West Rd, Wilmington, VT 05363
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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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  /19

  $469,000

  • 2 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363

  Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363
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  /2

  $245,000

  • 4 Beds
  • 2 Baths
  • 2,148 Sq Ft

  69 Grove St, Brattleboro, VT 05301

  69 Grove Street is a pleasant 2 unit home just a short walk from vibrant downtown. Each unit features 2 bedrooms, bath, living room and kitchen with wide board flooring and replacement windows. The first floor unit has a covered front porch, pantry and W&D hookups in the basement. The second floor apartment has an additional room (office), W&D hookups, decking and a rear staircase. Recent

  Robert Doyle Berkley & Veller Greenwood Country

  69 Grove St, Brattleboro, VT 05301
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  /42

  $349,000

  • 5 Beds
  • 3 Baths
  • 3,364 Sq Ft

  21 Main St, Saxtons River, VT 05154

  Historic 5 bedroom 3 bath home located in the heart of Saxtons River Village offering generous living space, classic character, and a convenient village setting. With multiple levels of living space and large rooms throughout, this home provides flexibility for a variety of living arrangements including space for guests, home offices, hobbies, or extended living needs. Original details and

  Thaddeus Abare Barrett and Valley Associates Inc.

  21 Main St, Saxtons River, VT 05154
• 

  

  /7

  $185,000

  • Land
  • 7 Acres
  • $26,429 per Acre

  0 Turkwood Rd Unit 5088320, Wardsboro, VT 05355

  Lovely parcels on town road, just off Route 100. 7 parcel subdivision, currently undeveloped, might be perfect location and keep the individual lots joined. Definitely good access on Route 100 for Skiing, winter and summer sports and the like. There an existing wooden shed on the property. Call your agent to set up a showing, this is a very nice property with a ton of potential.

  Tony Tribuno Skihome Realty

  0 Turkwood Rd Unit 5088320, Wardsboro, VT 05355
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  /6

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft

  48 Pleasant St, Brattleboro, VT 05301

  This handsome two unit home is located on desirable Pleasant Street and includes a large yard with plenty of parking. Each unit is 2 bedrooms, bath, living room and kitchen and they feature softwood flooring, bulls eye molding, replacement windows, decking and a covered front porch. Tenant pays for Electric and Heat and each unit has new Buderus boilers. W&D hookup up and Coin washer and dryer in

  Robert Doyle Berkley & Veller Greenwood Country

  48 Pleasant St, Brattleboro, VT 05301
• 

  

  /35

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,024 Sq Ft

  383 S Wardsboro Rd, Newfane, VT 05345

  Steeped in local history and meticulously preserved, this immaculate 1906 schoolhouse-turned-residence is a rare find in the heart of Newfane. After two decades as a cherished family retreat, this pristine three-bedroom home is ready for its next chapter. Positioned at the scenic intersection of South Wardsboro and Grout Pond Roads, the property is a true sensory sanctuary, where the gentle

  Thomas Dahlin Berkley & Veller Greenwood Country

  383 S Wardsboro Rd, Newfane, VT 05345
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  /9

  $369,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft

  47 Old Depot Rd, Putney, VT 05346

  Opportunities like this don't come around very often but this is your chance to own one of the most energy efficient, climate controlled, low carbon footprint, high performance builds around. Construction is underway right now. The home will be ready to move into by the end of August. Closing can happen anytime and the seller/project manager will stay on until the end. Best of all, you have the

  Victoria Woods Brattleboro Area Realty

  47 Old Depot Rd, Putney, VT 05346
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  /32

  $175,000

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

  9 Evergreen Ln, Brattleboro, VT 05301

  Discover a rare opportunity at 9 Evergreen in Brattleboro, VT. This 2-bedroom, 2-bathroom end unit condo is a blank canvas awaiting your creative vision. While the property requires a full renovation, the heavy lifting has already been done; the interior has been completely cleared out and is clean, making it truly ready for a straightforward and efficient transformation. The end unit position

  Kate Barry EXP Realty

  9 Evergreen Ln, Brattleboro, VT 05301
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  /53

  $1,249,000

  • 4 Beds
  • 3.5 Baths
  • 4,491 Sq Ft

  390 Pleasant Valley Rd, Brattleboro, VT 05301

  Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures

  Kristen Ziter Taylor Brattleboro Area Realty

  390 Pleasant Valley Rd, Brattleboro, VT 05301
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  /24

  $319,900

  • 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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  /14

  $50,000

  • Land
  • 12,632 Sq Ft
  • $172,414 per Acre

  41 Country Club Rd, Wilmington, VT 05363

  Set on 0.29 acres along a quiet dead-end, town-maintained paved road, this property offers a convenient and peaceful setting. The driveway is already in place, electric underground service is on site, and a natural spring is located on the property. Town sewer is available for hookup just down the street, making future improvements even easier. Nearby access to the VAST Trails. Included in the

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  41 Country Club Rd, Wilmington, VT 05363
• 

  

  /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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  /39

  $550,000

  • Land
  • 99.4 Acres
  • $5,533 per Acre

  188 Rattlesnake Mountain Rd, Townshend, VT 05353

  Townshend, Vermont sits in the heart of the West River Valley, minutes from Grafton, Londonderry, and Brattleboro. The property borders Vermont Route 30 and offers easy access to two of southern Vermont's premier ski resorts and the broader four-season recreational economy. A rare opportunity to own nearly 100 acres of productive Vermont forestland in one of Windham County's most scenic corridors

  Mike England Michael England Real Estate

  188 Rattlesnake Mountain Rd, Townshend, VT 05353
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  /51

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,874 Sq Ft

  41 Chapin St, Brattleboro, VT 05301

  Beautifully maintained, 1880s, in-town Victorian blends timeless elegance with modern comfort. The large, light-filled kitchen combines with an open, cathedral ceiling dining area inviting the gathering of family and friends. The renovated kitchen has granite, stainless steel appliances, and laundry area. Soaring, 9 ft ceilings create light-filled rooms. Elegance of timeless design and detailed

  Kristen Ziter Taylor Brattleboro Area Realty

  41 Chapin St, Brattleboro, VT 05301
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  /36

  $389,000

  • 7 Beds
  • 5 Baths
  • 3,460 Sq Ft

  733 Vermont 121, Westminster, VT 05101

  This 5-unit multi-family property presents a strong investment opportunity with steady, long-term tenants and consistent on-time rental history. Meticulously cared for over the years, the property features updated systems, public water, a double lot, and ample parking for tenants and guests alike. Current rents are below today’s market rates, offering clear opportunity for future income growth

  Morriah Adams BHG Masiello Brattleboro

  733 Vermont 121, Westminster, VT 05101
• 

  

  /52

  $545,000

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  1488 Hartley Hill Rd, Putney, VT 05346

  Welcome to this spacious contemporary home located on the desirable Hartley Hill Road, conveniently situated near Saxtons River, Bellows Falls, Putney, and I-91. Built in 2008, this well-maintained home offers quality craftsmanship, high-end utilities, and modern comforts throughout. The finished, walk-out lower level features radiant heat, abundant natural light, and exterior access from three

  Chelsea Richardson Barrett and Valley Associates Inc.

  1488 Hartley Hill Rd, Putney, VT 05346
• 

  

  /34

  $379,000

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft

  25 Speno Ct, Brattleboro, VT 05301

  Speno Court—one of Brattleboro’s most sought after neighborhoods—is a quiet, dead end street tucked between the beloved “Tree Streets” and just a short walk from downtown. With effortless access to over 9 miles of Retreat Farm trails, this tastefully remodeled home offers the perfect blend of convenience, comfort, and charm. Natural light fills the home through large picture windows and second

  Dan Normandeau Berkley & Veller Greenwood Country

  25 Speno Ct, Brattleboro, VT 05301
• 

  

  /34

  $899,000

  • 4 Beds
  • 3 Baths
  • 3,550 Sq Ft

  25 Yeaw Rd, Dover, VT 05341

  Enjoy year-round living in this handsome contemporary home set on over 12 acres of picturesque land, featuring open meadows, a gentle stream, a large pond, mixed woodland, and beautifully maintained gardens. Bright and inviting, the home offers a spacious layout designed for both comfort and entertaining. There is an attached 3 bay garage above which is a huge heated bonus room with storage

  Robert Doyle Berkley & Veller Greenwood Country

  25 Yeaw Rd, Dover, VT 05341
• 

  

  /30

  $580,000

  • 4 Beds
  • 4 Baths
  • 1,628 Sq Ft

  4 Lower Highlands Rd Unit G, Dover, VT 05356

  Welcome to 4G Lower Highlands Road in Dover, Vermont—a fully renovated 4-bedroom, 4-bathroom condo near Mount Snow offering modern upgrades and smart home technology. This turnkey mountain retreat has been thoughtfully updated from top to bottom, including remodeled bathrooms throughout, a fully finished lower level, and a stylish electric fireplace with custom hearth. The open and functional

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  4 Lower Highlands Rd Unit G, Dover, VT 05356
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  /57

  $650,000

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

  559 Parker Hill Rd, Springfield, VT 05156

  Nestled on Historic Parker Hill, this charming residence sits on a generous 10-acre lot that blends open spaces with woodlands, offering both privacy and natural beauty. The home features classic post and beam construction, highlighted by a cathedral ceiling and hardwood floors that create a warm and welcoming atmosphere. Large windows provide captivating views of the surrounding landscape,

  Heidi Bernier Berkley & Veller Greenwood Country

  559 Parker Hill Rd, Springfield, VT 05156
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  /44

  $65,000

  • Land
  • 36,154 Sq Ft
  • $78,313 per Acre

  123 High Top Rd, Wilmington, VT 05363

  Section B - new to market! Oversized building lot with new perc tests show it is suitable for a 3-bedroom single family home. Lot may support a larger home; buyer would have to pursue this option at their own cost. As an owner of an undeveloped lot in CHOA, you are entitled to all the recreation amenities in the Resort, including year-round swimming at the exclusive member-only clubhouse, located

  Sigrid Pickering Chimney Hill Realty

  123 High Top Rd, Wilmington, VT 05363
• 

  

  /50

  $1,800,000

  • 4 Beds
  • 5 Baths
  • 4,853 Sq Ft

  95 Middletown Rd, South Londonderry, VT 05155

  One-of-a-Kind Vermont Lifestyle PropertyHome, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated,

  Eric Nathan Nathan Auction & Real Estate Inc.

  95 Middletown Rd, South Londonderry, VT 05155
• 

  

  /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
• 

  

  /18

  $83,200

  • 3 Beds
  • 1 Bath
  • 1,414 Sq Ft

  2390 Morse Brook Rd, Putney, VT 05346

  Opportunity awaits in this serene Westminster Vermont setting! Nestled beside a charming babbling brook, this property offers the perfect backdrop to create your dream getaway or year-round home. The existing cottage is ready for a full renovation or a fresh start—bring your vision and unlock the true potential of this peaceful slice of Vermont. Rare chance to build equity in a highly desirable

  Linda Benoit Highland Realty

  2390 Morse Brook Rd, Putney, VT 05346
• 

  

  /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
• 

  

  /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

Showing Results 41 - 80, Page 2 of 10