251

Windham County VT Homes for Sale with Acreage

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  • /12

    $39,999

    • Land
    • 2 Acres
    • $20,000 per Acre

    14 Brickyard Rd, Dover, VT 05341

    Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy. From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

    David White OwnerEntry.com

    14 Brickyard Rd, Dover, VT 05341
  • /8

    $35,000

    • Land
    • 1 Acre
    • $35,000 per Acre

    0 Bourbon Run Rd, Jamaica, VT 05343

    1-acre building lot in beautiful zoning-free Jamaica, VT. From the roadside the property briefly slopes down a few feet before flattening out for the majority of the land, which is densely wooded throughout. Perhaps the parcel's best quality is simply its location. Bourbon Run road is just ten minutes from the Stratton base lodge and five minutes from all the shops and restaurants in downtown

    David White OwnerEntry.com

    0 Bourbon Run Rd, Jamaica, VT 05343
  • /31

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,378 Sq Ft

    383 Brookline Rd, Townshend, VT 05353

    This inviting ranch style home nestled on a country road is a little slice of heaven. Situated along a 14.8 acre parcel this sweet house has views, views, views. One level living offers a large family room with gas stove, vaulted beamed ceilings and opens to a covered screen porch and deck. The entrance has a spacious mudroom, cozy kitchen and dining area with plenty of pantry space. In addition

    Janet Lucier Barrett & Valley Assoc. Inc

    383 Brookline Rd, Townshend, VT 05353
  • /44

    $429,900

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft

    1909 Davidson Hill Rd, Westminster, VT 05158

    This charming Vermont country farmhouse offers peaceful privacy at the end of a quiet town road. Recently updated with quality materials and meticulous attention to detail, the home blends classic warmth with modern comfort. The open-concept main floor features a beautifully appointed kitchen ideal for family meals, flowing into the dining area and a cozy living room with a bay window and

    Steve Schoppmeyer BHG Masiello Brattleboro

    1909 Davidson Hill Rd, Westminster, VT 05158
  • /11

    $85,000

    • Land
    • 3 Acres
    • $28,333 per Acre

    1154 Vermont 8a, Whitingham, VT 05361

    3 Acres in picturesque Jacksonville Vermont – Here’s a great opportunity to create your Vermont getaway or forever home. This beautiful 3-acre lot offers a perfect mix of open space and natural scenery — ideal for outdoor enthusiasts. Enjoy nearby VAST snowmobile trails, fishing, hiking, and you're just 25 minutes from Mount Snow for skiing and year-round recreation.A mobile home once

    Kerry Mulverhill

    1154 Vermont 8a, Whitingham, VT 05361
  • /3

    $500,000

    • Land
    • 5.05 Acres
    • $99,010 per Acre

    Lot 1 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 5+ acres overlooking the 18th hole and mountains beyond for year

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 1 Mountain Ridge Estates, Wilmington, VT 05363
  • /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
  • /3

    $500,000

    • Land
    • 1.1 Acres
    • $454,545 per Acre

    Lot 2 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 1.1 acres overlooking the fairway of the 18th hole and mountains

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
  • /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
  • /9

    $185,000

    • Land
    • 8 Acres
    • $23,125 per Acre

    4441 Vermont 30, Jamaica, VT 05343

    Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

    Helen Nault

    4441 Vermont 30, Jamaica, VT 05343
  • /18

    $165,000

    • 3 Beds
    • 1 Bath
    • 1,188 Sq Ft

    310 Vermont 30, Newfane, VT 05345

    River frontage on the Smith Brook! This cape sits on the outskirts of the village of Newfane, minutes from the farm stand, restaurants, hardware store and everything else! There is a LOMA but a lender may still require flood insurance.Hardwood floors underneath the carpet. Price for a quick sale, this is an estate and being sold as is. Seller has no knowledge about the property.

    Victoria Woods Brattleboro Area Realty

    310 Vermont 30, Newfane, VT 05345
  • /38

    $1,600,000

    • 5 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    4427 W Hill Rd S, Jamaica, VT 05343

    One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

    Carrie Mathews Winhall Real Estate

    4427 W Hill Rd S, Jamaica, VT 05343
  • /29

    $199,000

    • Land
    • 4 Acres
    • $49,750 per Acre

    385 Chester Hill Rd, Grafton, VT 05146

    Rare opportunity to own acreage near edge of Grafton Village Vermont! This 4 acre parcel is offered for the first time in over 50 years! It truly is Grafton's best kept secret, driving by you would never know this opportunity exists. A rectangular lot on a paved town-maintained road with a driveway roughed into the center of the lot where you'll find a lovely pond and rustic cabin now ready to

    Jessica Landers Barrett and Valley Associates Inc.

    385 Chester Hill Rd, Grafton, VT 05146
  • /6

    $17,000

    • Land
    • 1.1 Acres
    • $15,455 per Acre

    00 Alpendorf Ave, Readsboro, VT 05353

    Build your dream mountain retreat in the heart of Vermont’s Green Mountains with this serene lot in Alpenwald Village, a private alpine-style community in Readsboro. Nestled across from the Green Mountain National Forest and the former Dutch Hill ski area, this parcel offers year-round recreation, peaceful surroundings, and direct access to VAST and VASA trail systems. This lot is ideal for a

    Kristen Breeden Southern Vermont Realty Group

    00 Alpendorf Ave, Readsboro, VT 05353
  • /6

    $27,000

    • Land
    • 2.2 Acres
    • $12,273 per Acre

    00 Bergrucken Ln, Readsboro, VT 05353

    Discover the perfect blend of privacy and community in Alpenwald Village with this beautiful double wooded lot. Located on a quiet street, this parcel offers a peaceful setting for your dream home or getaway cabin. The property comes with a wastewater site plan, saving you time and money as you plan your build. Enjoy year-round outdoor activities with nearby access to VAST and VASA trails,

    Kristen Breeden Southern Vermont Realty Group

    00 Bergrucken Ln, Readsboro, VT 05353
  • /27

    $249,000

    • 2 Beds
    • 1 Bath
    • 1,155 Sq Ft

    4668 Vermont 112, Halifax, VT 05342

    Historic hillside farm situated along the North River valley just a few miles into VT from MA on 31 acres of land. Approx. 5 acres of open sloping pasture most recently used as a sheep farm. The house is circa 1860 and has good bones and updated systems including a new drilled well, on demand HW, propane backup generator and other modern improvements. The interior of the home is in need of

    Chris Long BHG Masiello Brattleboro

    4668 Vermont 112, Halifax, VT 05342
  • /9

    $295,000

    • Land
    • 54.8 Acres
    • $5,383 per Acre

    0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355

    Explore the potential of this beautiful 53.8-acre parcel just 3.5 miles from the scenic Townshend Dam. This expansive property offers a peaceful, wooded setting with ample privacy—ideal for recreation, a future homesite, or continued forest management. Test pits have been completed, and results support the feasibility of a permitted septic system, paving the way for future development. Currently

    Carrie Mathews Winhall Real Estate

    0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
  • /25

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,536 Sq Ft

    1091 Townshend Dam Rd, Townshend, VT 05353

    Tucked away on 3 private acres, this 3-bedroom home offers the perfect blend of charm, space, and potential. Just 3.5 miles from Townshend Dam and 5 miles to the Wardsboro General Store, it's ideally located—only 20 minutes to Mount Snow and 30 to Stratton. Inside, a dramatic wall of glass with two sets of French doors floods the living space with natural light and brings the outdoors in. The

    Carrie Mathews Winhall Real Estate

    1091 Townshend Dam Rd, Townshend, VT 05353
  • /55

    $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
  • /56

    $425,000

    • 5 Beds
    • 3 Baths
    • 2,244 Sq Ft

    63 Big Story Ln, Grafton, VT 05146

    Discover the storybook charm and endless potential of 63 Big Story Lane in Grafton, Vermont. This extraordinary property spans just under 47 acres and features not one, but two unique dwellings — lovingly referred to as “Big Story” and “Short Story.” The main residence offers comfortable living with timeless Vermont charm and a natural pond, while the guest house, affectionately named “Short

    Erica Reynolds Southern Vermont Realty Group

    63 Big Story Ln, Grafton, VT 05146
  • /6

    $45,000

    • Land
    • 1.1 Acres
    • $40,909 per Acre

    9 Sun and Ski Rd, Wilmington, VT 05363

    Prime Land Lot – Minutes from Wilmington, Close to Mount Snow!Discover the perfect blend of seclusion and convenience with this exceptional land opportunity, ideally located just 8 minutes from Main Street Wilmington and only 20 minutes from the slopes of Mount Snow. Whether you're dreaming of a private mountain getaway, a cozy Airbnb investment, or building your forever home, this lot

    Flex Realty Group Flex Realty

    9 Sun and Ski Rd, Wilmington, VT 05363
  • /31

    $445,000

    • 2 Beds
    • 2 Baths
    • 1,230 Sq Ft

    212 S Pine Banks Rd, Putney, VT 05346

    Enchanting Putney Bungalow Retreat. Tucked away in a peaceful, sun-drenched meadow, this charming Putney bungalow offers the perfect blend of privacy, nature, and character. Surrounded by mature trees, stone walls, and abundant garden space, it’s a true hidden gem just minutes from the village center. Enjoy one-level living with a cozy first-floor bedroom and full bath and laundry—ideal for

    Karen Hoppe Berkley & Veller Greenwood Country

    212 S Pine Banks Rd, Putney, VT 05346
  • /54

    $2,050,000

    • 4 Beds
    • 4.5 Baths
    • 2,486 Sq Ft

    97 N Brookwood Rd, Stratton, VT 05360

    OPEN HOUSE SUNDAY OCTOBER 12TH 11:00AM-1:00PM!Welcome to your mountain chalet! 97 North Brookwood Road, one of the top most desirable locations on Stratton Mountain. Fully renovated and updated home, one of the eight original Austrian chalets on the mountain. Direct walk in and ski out to the Lower Wanderer trail. 4 bedroom in total with 3 en-suite bathrooms and 1 custom double bunk

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    97 N Brookwood Rd, Stratton, VT 05360
  • /12

    $325,000

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

    2366 Middletown Rd, Landgrove, VT 05148

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

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    2366 Middletown Rd, Landgrove, VT 05148
  • /39

    $194,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    236 Hall Bridge Rd, Bellows Falls, VT 05101

    Location location location! If you want to own your own piece of Vermont beauty surrounded by woods in a private setting that includes a pond, two garages, a tiny cabin and a shed, this might be the property of your dreams! The home needs TLC and updating, but taking a break on the expansive deck and enjoying the sounds and sights of nature is something you'll want to do. This property is the

    Heather Gleim CENTURY 21 North East

    236 Hall Bridge Rd, Bellows Falls, VT 05101
  • /41

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 4,153 Sq Ft

    487 Vermont Route 100, Londonderry, VT 05148

    Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a

    Jamie Wylie Stratton Real Estate

    487 Vermont Route 100, Londonderry, VT 05148
  • /60

    $798,000

    • 3 Beds
    • 3 Baths
    • 2,757 Sq Ft

    1909 Pine Banks Rd, Putney, VT 05346

    Sweetwood Farm circa 1894, this beautifully maintained extended Cape encompasses 60 serene acres of rolling meadows, shaded woodlands, and a peaceful, cascading brook. If you've been dreaming of a home that offers a convenient location, charm, and connection to the land, this is it. Inside, you'll find warm wide-pine floors, handcrafted cherry cabinets, and cozy living spaces filled with

    Heidi Bernier Berkley & Veller Greenwood Country

    1909 Pine Banks Rd, Putney, VT 05346
  • /15

    $530,000

    • Land
    • 30 Acres
    • $17,667 per Acre

    00 W Hill Rd S, Jamaica, VT 05343

    Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

    Jacki Murano Southern Vermont Realty Group

    00 W Hill Rd S, Jamaica, VT 05343
  • /53

    $1,470,000

    • 5 Beds
    • 4.5 Baths
    • 5,160 Sq Ft

    224 Cobble Ridge Rd, Londonderry, VT 05148

    Perched on scenic Cobble Ridge, this custom five-bedroom, four-and-a-half-bath retreat embodies balance, light, and renewal in the heart of Southern Vermont. Set on seven private, fenced acres framed by stone walls and dual gated entries, the property enjoys southwest exposure with soft, filtered ridgeline views that evolve beautifully through the seasons. Inside, a brick fireplace anchors the

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    224 Cobble Ridge Rd, Londonderry, VT 05148
  • /41

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    216 Ghastly Job Way, Wilmington, VT 05363

    Vermont mountain getaway perched on a private parcel at the end of a quiet country road, this charming mountain retreat offers sweeping long-range views spanning from the Green Mountains within the National Forest north to Mount Snow and east toward neighboring Marlboro. Enjoy breathtaking sunsets from the covered front porch or relax in the outdoor hot tub surrounded by nature. Inside, the

    Monique White Deerfield Valley Real Estate

    216 Ghastly Job Way, Wilmington, VT 05363
  • /20

    $195,000

    • Land
    • 46.2 Acres
    • $4,221 per Acre

    1499 Josh Rd, Halifax, VT 05358

    46 + acres (33 AC in Halifax & 13.20 AC in Guilford) with a modified camper accessed by an existing gravel woods road off Josh Road (class 4) and beautiful pond with dock in a peaceful remote valley surrounded by over 2,000 acres of private land mostly open to recreation with miles of trails and old town roads. Josh Brook is a major trout stream and has waterfalls and deep pools for cooling off.

    Chris Long BHG Masiello Brattleboro

    1499 Josh Rd, Halifax, VT 05358
  • /58

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,583 Sq Ft

    25 Old School St, South Londonderry, VT 05155

    Welcome to your quintessential Vermont retreat! This freshly painted red Cape is perfect as a full-time residence or a ski-season getaway. Ideally located just off Main Street in South Londonderry, you can stroll to the post office or grab a bite at the beloved Corner Market Deli.Ski enthusiasts will love the proximity to multiple mountains — Magic Mountain (9 min), Bromley (13 min),

    Jared Bove United Country Real Estate Mike Jarvis Group Inc

    25 Old School St, South Londonderry, VT 05155
  • /35

    $579,000

    • 4 Beds
    • 1 Bath
    • 1,560 Sq Ft

    104 Karen Day Rd, Halifax, VT 05342

    1860's Colonial/Farmhouse situated on nearly 37 acres of gorgeous land. This location, exposure, access and overall site characteristics is truly one of a kind. Ultimate privacy due to the town-maintained road (Karen Day Road) running from Larrabee Road all the way to the house and compound with no other houses along the road or in sight whatsoever. The land is remarkable with level open fields,

    Chris Long BHG Masiello Brattleboro

    104 Karen Day Rd, Halifax, VT 05342
  • /54

    $1,400,000

    • 5 Beds
    • 4.5 Baths
    • 4,908 Sq Ft

    131 Stark Rd, Brattleboro, VT 05301

    Remember when you were 6 and the Hundred Acre Wood seemed as big as the whole world? Now is the time to write your own story...and live in your own Hundred Acre Wood....only this one is grown up with 103 acres, 35 acres of open meadow, about 1/4 mile bordering the Whetstone Brook, a great barn, nearly 4000 square feet of living space and so many stories to live! With a perfect

    Christine Lewis Brattleboro Area Realty

    131 Stark Rd, Brattleboro, VT 05301
  • /20

    $475,000

    • Land
    • 136.9 Acres
    • $3,470 per Acre

    0 Taft Rd Unit 5064573, Townshend, VT 05353

    In the late 1790's, General Samuel Fletcher gave a large parcel of land to young Benjamin Murdock, whose father had died from smallpox while serving in the Revolutionary War. Benjamin built a cabin and then a house, cleared and plowed the land, and with his wife raised 8 children. That land is now known as Murdock Mountain. Entering the property is like stepping into the past. The deep stone

    Bill Hickok Berkley & Veller Greenwood Country

    0 Taft Rd Unit 5064573, Townshend, VT 05353
  • /37

    $479,000

    • 2 Beds
    • 2 Baths
    • 2,016 Sq Ft

    529 Finkel Rd, Wardsboro, VT 05355

    Sage Hill offers the perfect blend of privacy and convenience, set along a scenic country road yet just minutes to groceries, gas, and skiing. This contemporary home is thoughtfully tucked back into the landscape, framed by classic stonewalls and majestic oak trees. Enter directly from the carport into a tiled mudroom with closet space, ideal for storing all your outdoor gear. The main living

    Monique White Deerfield Valley Real Estate

    529 Finkel Rd, Wardsboro, VT 05355
  • /26

    $149,000

    • Land
    • 19.4 Acres
    • $7,680 per Acre

    2610 Lower Dover Rd, Marlboro, VT 05344

    Marlboro Sanctuary – Private Meadow Retreat. Discover this beautiful and private parcel in the heart of Marlboro, featuring an open meadow with sunny southern exposure. With generous road frontage and easy access between two charming stonewalls, a well-maintained old logging road leads you into the property. Along the way, pass by a small pond site before arriving at the expansive meadow, framed

    Monique White Deerfield Valley Real Estate

    2610 Lower Dover Rd, Marlboro, VT 05344
  • /37

    $325,000

    • 2 Beds
    • 1 Bath
    • 588 Sq Ft

    787 Vermont 30, Newfane, VT 05345

    This Ain’t Your Average Cape Cod Cottage!Sure, this 2-bedroom, 1-bath Cape has the sweet front porch you’ve been dreaming about, perfect for sipping that morning coffee, plus a side patio that’s just begging for summer barbecues (bonus: pop on the panels and you’ve got yourself a three-season hangout!). But the real showstopper here isn’t the house—it’s the 30x40 heated workshop out

    TG Glazer Winhall Real Estate

    787 Vermont 30, Newfane, VT 05345
  • /39

    $519,000

    • Land
    • 80.11 Acres
    • $6,479 per Acre

    47 Whites Hill Rd, Dover, VT 05341

    Escape to Your Private 80-Acre Paradise – Nature, Adventure, and Opportunity Await!Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income

    Joe Castaluccio Winhall Real Estate

    47 Whites Hill Rd, Dover, VT 05341
  • /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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