Windham County VT Houses for Sale

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  /38

  $495,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,115 Sq Ft

  367 Stratton Gate Rd, Jamaica, VT 05343

  Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

  

  Alison Cummings

  Cummings & Co

  367 Stratton Gate Rd, Jamaica, VT 05343
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  /40

  $535,000

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

  619 Main St, South Londonderry, VT 05155

  Set on 3 lovely acres in the heart of South Londonderry, this gracious four-bedroom, 2½-bath Victorian blends timeless character with thoughtful modern updates. Original floor-to-ceiling windows, soaring ceilings, hardwood floors, and classic Victorian details create a warm and inviting sense of history throughout the home.The newly renovated kitchen provides a fresh, functional gathering

  

  Alison Cummings

  Cummings & Co

  619 Main St, South Londonderry, VT 05155
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  /60

  $3,800,000

  $2M PRICE DROP

  • 4 Beds
  • 8 Baths
  • 16,736 Sq Ft

  1950 Collins Rd, Brattleboro, VT 05301

  Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or

  

  Margretta Fischer

  Wohler Realty Group

  1950 Collins Rd, Brattleboro, VT 05301
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  /43

  $495,000

  $40K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft

  176 Brophy Ln, Londonderry, VT 05148

  Discover this charming Vermont log cabin, situated on a quiet, secluded lot just 5 minutes from downtown Londonderry, and 15 minutes to downtown Manchester's restaurants and shopping. This home offers the perfect balance of peaceful mountain living and easy access to local amenities.The first level welcomes you into a large, open-concept living room, dining room, and kitchen area, perfect

  

  Christopher Cummings

  Cummings & Co

  176 Brophy Ln, Londonderry, VT 05148
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  /31

  $253,000

  $6K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  51 Golding Rd, Windham, VT 05359

  This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the

  

  Alison Cummings

  Cummings & Co

  51 Golding Rd, Windham, VT 05359
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  /13

  $699,000

  • 3 Beds
  • 2 Baths
  • 3,044 Sq Ft

  661 Wright Orchard Rd, Grafton, VT 05146

  Turn-key, beautifully furnished, and ready to enjoy, this exceptional Vermont property is being offered with all brand-new furnishings included, making it a rare opportunity to step right into the Vermont lifestyle. Set on 20 private acres in the heart of Grafton, this beautifully maintained 3-bedroom, 2-bath home with a custom office offers the perfect blend of comfort, versatility, and modern

  

  Gail Beardmore

  Engel & Völkers Okemo

  661 Wright Orchard Rd, Grafton, VT 05146
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  /51

  $799,000

  • 4 Beds
  • 5 Baths
  • 3,992 Sq Ft

  1035 Vermont 121, Windham, VT 05359

  Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A

  Jamie Wylie Stratton Real Estate

  1035 Vermont 121, Windham, VT 05359
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  /52

  $499,000

  • 5 Beds
  • 4 Baths
  • 3,665 Sq Ft

  522 Vermont Route 100, Wardsboro, VT 05355

  Dating to the 1830s and thoughtfully renovated through the 1990s and early 2000s, this Vermont homestead blends historic character with the comforts of modern living. Set on 12 mostly open, level acres surrounded by mountains, it offers the kind of setting people dream about but rarely find. Start your morning with coffee overlooking the meadow as mist rises from the fields and the sound of the

  Lee Brown Four Seasons Sotheby's Int'l Realty

  522 Vermont Route 100, Wardsboro, VT 05355
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  /24

  $229,000

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  8 Novice Village Rd, West Dover, VT 05356

  Offered for the first time in nearly 50 years, this two bedroom chalet with a sleeping loft is perfectly suited as a ski retreat, weekend getaway, or renovation project in the heart of Dover. The main level offers an open concept kitchen, dining, and living area anchored by a cozy wood burning fireplace, ideal for unwinding after a day on the slopes. Two bedrooms and a full bathroom round out

  Megan Quinn Southern Vermont Realty Group

  8 Novice Village Rd, West Dover, VT 05356
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  /42

  $479,999

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  7 High Top Unit B117, Wilmington, VT 05363

  Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and

  Sigrid Pickering Chimney Hill Realty

  7 High Top Unit B117, Wilmington, VT 05363
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  /21

  $349,000

  • 4 Beds
  • 1 Bath
  • 1,608 Sq Ft

  2068 S Wardsboro Rd, Wardsboro, VT 05355

  Charming cabin just outside the village of Wardsboro in Southern Vermont. This home away from home is being offered for sale for the first time by the original owners that built it. Up a private drive with easy access off a paved road sits this rustic retreat, overlooking a river and short range mountain view across the way. The home has a large open concept living space with the exposed log

  Adam Palmiter Berkley & Veller Greenwood/Dover

  2068 S Wardsboro Rd, Wardsboro, VT 05355
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  /21

  $489,000

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  12 Lilla Ln, Wilmington, VT 05363

  Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

  Adam Palmiter Berkley & Veller Greenwood/Dover

  12 Lilla Ln, Wilmington, VT 05363
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  /48

  $565,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Great Location, New Roof, New Septic, recent exterior painting! This turn key residence is ideally located between three ski areas and near schools and shopping. Gourmet kitchen, wood floors, upscale baths and a huge 3 car garage/ barn with finished office space. Tucked amidst the forest with views of Magic Mountain's ridge line, whether you are looking for a second home in the mountains or

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
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  /34

  $695,000

  $170K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 2,481 Sq Ft

  1871 W Hill Rd, Townshend, VT 05353

  Welcome to your fully furnished chalet-style escape in Townshend, Vermont. Tucked away at the end of a private drive on 10 partially cleared, usable acres, this 2-bedroom, 2-bathroom home offers the perfect blend of comfort and Vermont charm. With four separate sleeping areas, there's plenty of space. The first-floor primary suite provides a private retreat with its own ensuite bathroom. Above, a

  Kim Meeker Southern Vermont Realty Group

  1871 W Hill Rd, Townshend, VT 05353
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  /29

  $799,999

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,592 Sq Ft

  62 Potter Rd, Wardsboro, VT 05355

  Brand-new construction in process in Wardsboro, set on a spacious 2-acre parcel. Introducing a brand-new 3-bedroom, 3.5-bath home is slated for completion in late fall 2026. Inside, you’ll find beautiful natural light, wide-plank pine flooring, oversized windows, and an inviting, bright living space. The main level offers an open-concept layout with a well-appointed kitchen, dining area, and

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  62 Potter Rd, Wardsboro, VT 05355
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  /26

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  57 Vartland Ridge, Londonderry, VT 05148

  Set on 1.1 acres with access to VAST trails, this property offers a blend of recent upgrades, functional space, and future potential. Being sold as-is, the property offers the chance to update and customize while benefiting from several major upgrades already completed. Recent improvements include a new furnace and hot water heater installed in 2022, along with a new propane tank and updated

  Jamie Wylie Stratton Real Estate

  57 Vartland Ridge, Londonderry, VT 05148
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  /39

  $2,195,000

  • 4 Beds
  • 4 Baths
  • 3,524 Sq Ft

  392 Lake Raponda Rd, Wilmington, VT 05363

  A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake - with a private dock - just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats

  Adam Palmiter Berkley & Veller Greenwood/Dover

  392 Lake Raponda Rd, Wilmington, VT 05363
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  /60

  $995,000

  • 4 Beds
  • 3 Baths
  • 2,821 Sq Ft

  179 Reed Rd, Athens, VT 05143

  Custom Swedish Cope Log Home on 14 plus acres in Southern Vermont.Hidden among the hills, this custom log home combines rugged craftsmanship with warm, open living spaces. Oversized timbers transported from Idaho were assembled in the Swedish Cope style, featuring traditional saddle notched logs that give the home its distinctive character.A cathedral style entry leads into a dramatic

  Julie Lowe Lowe's Real Estate, LLC

  179 Reed Rd, Athens, VT 05143
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  /59

  $425,000

  • 5 Beds
  • 3 Baths
  • 1,440 Sq Ft

  135 Overlook Dr, Londonderry, VT 05148

  Investment opportunity! This beautiful ski country compound offers 3 potential streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are

  Zachary Zupan EXP Realty

  135 Overlook Dr, Londonderry, VT 05148
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  /26

  $290,000

  • 5 Beds
  • 1.5 Baths
  • 2,167 Sq Ft

  207 Elliot St, Brattleboro, VT 05301

  Offered to the public for the first time in nearly 60 years, this majestic Colonial-style home is located in one of Brattleboro’s oldest neighborhoods. The property showcases exquisite original details, including maple floors and fine hardwood trim throughout both levels. Many of the original plaster walls and ceilings have been professionally restored and await your personal color choices. The

  Bill Hickok Berkley & Veller Greenwood Country

  207 Elliot St, Brattleboro, VT 05301
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  /24

  $269,400

  • 1 Bed
  • 1,350 Sq Ft

  2903 State Forest Rd, Townshend, VT 05353

  This is such a blank canvas for you to make your own. Taken down to the studs with a newer roof, windows, and siding, this home is ready for you to come in and make it your own. Seller has never lived here, so the Buyer will have to do their due diligence. Lot is currently 1.5 acres, but the boundary line will be adjusted prior to closing to make the lot around 5+/- acres including river frontage

  Jim Bellville Bellville Realty

  2903 State Forest Rd, Townshend, VT 05353
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  /30

  $649,000

  • 5 Beds
  • 3 Baths
  • 2,830 Sq Ft

  36 Bears Den Rd, West Dover, VT 05356

  Lovely ski home home in an ideal location, offering the privacy of a single-family residence with the convenience of a groomed ski-home trail and direct shuttle service just steps from your front door.Nestled on a well-positioned lot in the desirable Bears Crossing community, the home backs directly to the ski-home trail with a bridge to cross right to your deck on your way home and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  36 Bears Den Rd, West Dover, VT 05356
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  /27

  $249,900

  • 2 Beds
  • 1.5 Baths
  • 2,184 Sq Ft

  6 Church St, Wilmington, VT 05363

  Located in the heart of Wilmington, this charming two bedroom, one and a half bath home offers an excellent opportunity to create something truly special. Just a short walk to shops, restaurants, and everything downtown has to offer, the location is hard to beat. The home features an attached garage with potential unfinished space above, offering endless possibilities for expansion, a home

  Julie Lowe Lowe's Real Estate, LLC

  6 Church St, Wilmington, VT 05363
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  /56

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 2,392 Sq Ft

  46 Pearce Cir, Town of Rockingham, VT 05101

  Nestled on 8.75 private, mostly wooded acres with gorgeous mountain and river valley views, this turnkey 3 bedroom, 3 bathroom contemporary home has been extensively updated and thoughtfully improved. Step in from the front entryway into a generous mudroom with custom built-ins and tiled floors, leading directly into an expansive open-= concept living space with vaulted ceilings, radiant heat,

  Kate Barry EXP Realty

  46 Pearce Cir, Town of Rockingham, VT 05101
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  /33

  $459,000

  • 1 Bed
  • 2.5 Baths
  • 2,076 Sq Ft

  33 W Main St, Wilmington, VT 05363

  Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or

  Adam Palmiter Berkley & Veller Greenwood/Dover

  33 W Main St, Wilmington, VT 05363
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  /56

  $624,900

  • 4 Beds
  • 2.5 Baths
  • 2,904 Sq Ft

  37 Stowe Hill Rd, Wilmington, VT 05363

  Welcome to Spruce Hill Farm, circa 1890, a beautifully restored farmhouse set on 47.7 picturesque acres just minutes from the charming village of Wilmington, Lake Raponda, Lake Whitingham, Mount Snow Ski Resort, and The Hermitage Club at Haystack. Lovingly renovated by its current owners since 1997, this exceptional property seamlessly blends modern amenities with timeless New England charm.

  Monique White Deerfield Valley Real Estate

  37 Stowe Hill Rd, Wilmington, VT 05363
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  /59

  $309,000

  $66K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  1192 Chapel Hill Rd, Whitingham, VT 05361

  Discover the perfect Vermont four-season retreat in this architecturally unique round home, set on a picturesque 1-acre corner lot in Southern Vermont. Offered fully furnished and move-in ready, this 1,840-square-foot, 3-bedroom, 2-full-bath property is ideal as a year-round residence, vacation home, or turnkey getaway.The welcoming lower level features three comfortable bedrooms, a

  Cliff Leinonen Four Seasons Sotheby's Int'l Realty

  1192 Chapel Hill Rd, Whitingham, VT 05361
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  /37

  $699,000

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

  42 Bills Rd, Stratton, VT 05360

  Private Vermont Log Cabin Retreat Near Stratton Mountain. Nestled at the end of a quiet dead-end road and bordering the Green Mountain National Forest, this exceptional log cabin at 42 Bills Road offers the ultimate Vermont mountain escape. Located just minutes from Stratton Mountain Resort, this fully furnished three-bedroom, three-bathroom home combines rustic charm with modern comfort in a

  Julie Lowe Lowe's Real Estate, LLC

  42 Bills Rd, Stratton, VT 05360
• 

  

  /35

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 2,359 Sq Ft

  116 Teacher Rd, Jamaica, VT 05343

  Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time

  Carrie Mathews Winhall Real Estate

  116 Teacher Rd, Jamaica, VT 05343
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  /29

  $224,900

  • 2 Beds
  • 1 Bath
  • 1,017 Sq Ft

  1892 US Rt 5, Dummerston, VT 05346

  Local history suggests this charming Dummerston bungalow may have begun its life as a one-room schoolhouse. Offering 1,017 square feet of living space, the home features two bedrooms, a full bath, a dedicated dining area, and a separate laundry room. Its warm wood details and practical single-level layout provide an inviting starting point for restoration and personalization.Outside, the

  Linda Benoit Highland Realty

  1892 US Rt 5, Dummerston, VT 05346
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  /59

  $354,900

  • 3 Beds
  • 1.5 Baths
  • 1,586 Sq Ft

  21 Big Bend Loop, Wilmington, VT 05363

  Welcome to 21 Big Bend Loop in Wilmington, VT, where mountain charm, year-round adventure, and peaceful surroundings come together. Tucked among the trees, this chalet-style home offers the perfect escape, whether you're looking for a full-time residence, a weekend getaway, or an investment property in one of Southern Vermont's most desirable recreation areas. Step inside through the spacious

  Kelsey Malloy Keller Williams Realty Metro-Keene

  21 Big Bend Loop, Wilmington, VT 05363
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  /43

  $549,900

  $25K PRICE DROP

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

  1 Bucket Ln, Dover, VT 05356

  NEW PRICE! Exceptional Value in Vermont’s Ski Country! This beautifully renovated classic chalet just became an even better opportunity! Offering the perfect blend of rustic Vermont charm and modern updates, this home features vaulted ceilings, exposed beams, a dramatic floor-to-ceiling brick fireplace, gorgeous remodeled kitchen with quartz countertops, and an expansive deck ideal for

  Linda Benoit Highland Realty

  1 Bucket Ln, Dover, VT 05356
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  /52

  $1,997,000

  • 4 Beds
  • 4.5 Baths
  • 3,631 Sq Ft

  14 Talon Dr, Stratton, VT 05360

  Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional custom timber frame home by Wadsworth Design Build offers the best of Southern Vermont living. Tucked within a private neighborhood and backing directly to the Green Mountain National Forest, the property provides a peaceful setting with immediate access to hiking, snowshoeing, and year-round outdoor recreation right

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  14 Talon Dr, Stratton, VT 05360
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  /60

  $3,995,000

  • 4 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  816 Black Bear Rd, Jamaica, VT 05343

  Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  816 Black Bear Rd, Jamaica, VT 05343
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  /41

  $2,699,000

  $2M PRICE DROP

  • 6 Beds
  • 3 Baths
  • 3,309 Sq Ft

  36 Woffenden Rd, Wilmington, VT 05363

  Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds.Boasting a coveted southeast exposure, the home and land are cheerful

  Melissa Ellis Southern Vermont Realty Group

  36 Woffenden Rd, Wilmington, VT 05363
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  /45

  $1,165,000

  • 4 Beds
  • 2.5 Baths
  • 3,338 Sq Ft

  1472 Carpenter Hill Rd, Guilford, VT 05301

  The Governor Carpenter Homestead, a pivotal piece of American history in Guilford, VT, is now accepting applications for its next Steward. This remarkable property was constructed in 1772 by Benjamin Carpenter, Vermont's first Lieutenant Governor. Lovingly maintained for decades, the residence combines historic integrity with modern functionality. Key features include: Architectural Significance:

  Thomas Dahlin Berkley & Veller Greenwood Country

  1472 Carpenter Hill Rd, Guilford, VT 05301
• 

  

  /41

  $439,000

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

  1137 Upper Dummerston Rd, Brattleboro, VT 05301

  Elegant and charming cape with an enchanting, exceptional garden that will impress even the seasoned green thumb. This magnificent home is solar equipped; the owner has had no electric bills for 3 years and the solar agreement may be transferred to the new buyer. Classic Vermont timeless style throughout features gorgeous archways, built-ins, and oak flooring. The kitchen is spacious with a

  Kristen Ziter Taylor Brattleboro Area Realty

  1137 Upper Dummerston Rd, Brattleboro, VT 05301
• 

  

  /33

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft

  57 Timber Ln, Wardsboro, VT 05360

  Conveniently located between Mount Snow and Stratton Resort you'll find this three-bedroom, two-bathroom home surrounded by lush perennial gardens that thrive in the sun of the one-acre lot's southern exposure within the desirable Snow Mountain Farms community of Wardsboro, Vermont. The main level features an inviting open-concept layout that seamlessly connects the galley kitchen with eat-in

  Kim Meeker Southern Vermont Realty Group

  57 Timber Ln, Wardsboro, VT 05360
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  /42

  $499,000

  $26K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  147 Gilbert Rd, Guilford, VT 05301

  This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting

  Monica Sumner BHG Masiello Brattleboro

  147 Gilbert Rd, Guilford, VT 05301
• 

  

  /40

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,022 Sq Ft

  564 Goodaleville Rd, Jamaica, VT 05343

  10 MINUTES TO STRATTON RESORT | This beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition, and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain

  Cheyanne Pugliese

  564 Goodaleville Rd, Jamaica, VT 05343

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