Windsor County VT Homes for Sale with Acreage

• 

  

  

  /22

  $290,000

  • Land
  • 75 Acres
  • $3,867 per Acre

  1175 Quarry Rd, Chester, VT 05143

  An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

  Jessica Samples BHG Masiello Keene

  1175 Quarry Rd, Chester, VT 05143
• 

  

  

  /19

  $125,000

  • Land
  • 10.24 Acres
  • $12,207 per Acre

  0 Hoey Rd, Cavendish, VT 05142

  This is a special property. Ten acres of woodland with a mix of hardwood and softwood. There appear to be many harvestable trees. There are a couple of different building sites...one on the flat spot on the lower side of the property overlooking the stonewall and the brook. The other is on the uphill side where you also have a flat spot and a gorgeous view of the neighboring field. The property

  Betty McEnaney Diamond Realty

  0 Hoey Rd, Cavendish, VT 05142
• 

  

  

  /37

  $1,995,000

  • 4 Beds
  • 2.5 Baths
  • 3,839 Sq Ft

  198 Piper Hill Rd, Weston, VT 05161

  Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house

  Story Jenks LandVest, Inc/Woodstock

  198 Piper Hill Rd, Weston, VT 05161
• 

  

  

  /38

  $1,499,000

  • 4 Beds
  • 5 Baths
  • 3,500 Sq Ft

  2391 Music Mountain Rd, Stockbridge, VT 05772

  OVER $496,000 PRICE ADJUSTMENT AND OVER $120,000 RENTAL INCOME, THIS ONE YOU SHOULD CONSIDER OWNING. LUXURY FURNISHINGS TOO. TIMBERS IN THE SKY – Featured in Log and Timber Home Living magazine, this one-of-a-kind Vermont timber frame retreat, built in 2022, blends dramatic architecture with refined comfort. Fully furnished with luxury pieces, the open floor plan showcases a soaring great room

  Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

  2391 Music Mountain Rd, Stockbridge, VT 05772
• 

  

  

  /60

  $2,499,000

  • 4 Beds
  • 3.5 Baths
  • 5,079 Sq Ft

  254 Town Line Rd, Plymouth, VT 05056

  First time offered on market! Stunning VT private estate on over 22 +/- acres w/mountain views, gorgeous gardens & 2 ponds one of which is a 7-feet-deep spring fed glacial pond. This exquisite property has been meticulously designed & custom crafted by the owner who is a well-known respected master builder. As you enter this gem you will experience the thoughtful care everywhere you look.

  Marni Rieger KW Vermont-Killington

  254 Town Line Rd, Plymouth, VT 05056
• 

  

  /60

  $475,000

  • 4 Beds
  • 5 Baths
  • 3,036 Sq Ft

  7868 Pomfret Rd, North Pomfret, VT 05053

  CASH FLOW POSITIVE - PRICE REDUCTION! A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 1.84 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office

  John Bassette Bassette Real Estate Group

  7868 Pomfret Rd, North Pomfret, VT 05053
• 

  

  /60

  $1,499,000

  • 4 Beds
  • 3.5 Baths
  • 3,560 Sq Ft

  652 Tierney Rd, Cavendish, VT 05142

  Tucked discretely off a meandering country road you will find this charming 4 bedroom, 3 and 1/2 bath contemporary home sited on 40 acres of land with miles of groomed trails that include a picnic area on Twenty Mile Stream. The grand living room , anchored by a wood-burning fireplace and lined by a wall of windows , frames views of the giant swimming pond and long range mountain views that

  Carol Wood Williamson Group Sothebys Intl. Realty

  652 Tierney Rd, Cavendish, VT 05142
• 

  

  /32

  $2,300,000

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

  134 Chester Arthur Rd, Hartford, VT 05047

  A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

  John Wetmore Wetmore Real Estate

  134 Chester Arthur Rd, Hartford, VT 05047
• 

  

  /60

  $200,000

  • Land
  • 6.63 Acres
  • $30,166 per Acre

  00 Vermont 103, Andover, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

  Rachael Rogala Lange & Lange

  00 Vermont 103, Andover, VT 05143
• 

  

  /60

  $115,000

  • Land
  • 3.28 Acres
  • $35,061 per Acre

  00 Vt Route 103 N, Chester, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

  Rachael Rogala Lange & Lange

  00 Vt Route 103 N, Chester, VT 05143
• 

  

  /37

  $985,000

  • 4 Beds
  • 3 Baths
  • 2,785 Sq Ft

  1782 Randall Rd, Woodstock, VT 05091

  This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

  Wade Treadway Wade I Treadway Real Estate

  1782 Randall Rd, Woodstock, VT 05091
• 

  

  /54

  $685,000

  • 4 Beds
  • 3.5 Baths
  • 2,828 Sq Ft

  119 Pine Hill Rd, Ludlow, VT 05149

  Nestled in the desirable Okemo Pines community, this 4-bedroom, 3.5-bath home offers the perfect blend of comfort, charm, and convenience, only minutes from Okemo Mountain Resort. Thoughtfully designed for year-round enjoyment, the home features multiple seasonal living areas, including a large deck with Okemo views, a sunroom, and a covered porch with mountain views. The house offers privacy

  Joseph Karl William Raveis Real Estate Vermont Properties

  119 Pine Hill Rd, Ludlow, VT 05149
• 

  /2

  $450,000

  • Land
  • 119 Acres
  • $3,782 per Acre

  00 Bradley Hill Rd Unit 121, Norwich, VT 05055

  Unusually large parcel of land in Norwich. 119 +/- ac with over 2500' of road frontage on delightful Bradley Hill Road. Close to town yet calm and quiet. The land abuts conservation land and the "Bradley Hill Loop" - a maintained trail. Not yet in Current Use though the forestry plan is ready to be implemented. A great opportunity to build in the Dresden School District.

  Jane Darrach Martha E. Diebold/Hanover

  00 Bradley Hill Rd Unit 121, Norwich, VT 05055
• 

  

  /14

  $199,000

  • Land
  • 27.1 Acres
  • $7,343 per Acre

  00 Albin Hill Rd, Braintree, VT 05060

  Imagine waking up to sweeping vistas of Vermont’s Green Mountains, surrounded by 27.1 acres of pure tranquility. This rare parcel offers the perfect canvas for your dream estate, luxury retreat, or off-the-grid sanctuary. Perched at an impressive 1,800 feet in elevation, the property offers stunning panoramic views and unparalleled privacy, while still being just minutes from amenities, shopping

  Will Spanos KW Vermont-Killington

  00 Albin Hill Rd, Braintree, VT 05060
• 

  

  /32

  $875,000

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

  233 Brothers Rd, Hartland, VT 05048

  The idyllic Hartland countryside is the setting for this handsome cape. A delightful three season porch is entered by way of the attached two car garage or directly by a lovely landscaped pathway. Once inside you will be greeted by a warm and inviting kitchen detailed with cherry cabinetry, the dining room with a bay window view of the gardens,a living room with fireplace, and a spacious

  Mary Mayhew Snyder Donegan Real Estate Group

  233 Brothers Rd, Hartland, VT 05048
• 

  

  /19

  $325,000

  • Land
  • 18 Acres
  • $18,056 per Acre

  00 Turtle Hill Rd, Ludlow, VT 05149

  Build Your Dream Home on a Private 18-Acre Estate in South HillDiscover the perfect setting for your custom-designed residence on this expansive 18-acre parcel, ideally situated at the secluded end of a cul-de-sac within South Hill's exclusive community. This exceptional property offers a rare blend of privacy and convenience, surrounded by other custom-built homes. Imagine your new home

  Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

  00 Turtle Hill Rd, Ludlow, VT 05149
• 

  

  /15

  $85,000

  • Land
  • 4.05 Acres
  • $20,988 per Acre

  00 Hillcrest Dr, Andover, VT 05143

  Ready to Build in Southern Vermont! Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for remote work

  Daire Gibney Barrett and Valley Associates Inc.

  00 Hillcrest Dr, Andover, VT 05143
• 

  

  /60

  $3,650,000

  • 5 Beds
  • 4 Baths
  • 5,181 Sq Ft

  348 Turtle Hill Rd, Ludlow, VT 05149

  Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited on over 13 acres, the property offers sweeping, panoramic views of southern Vermont's mountains and valleys; vistas that are truly second to none. The home's architectural highlights include hand-hewn Douglas fir beams

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  348 Turtle Hill Rd, Ludlow, VT 05149
• 

  

  /60

  $1,500,000

  • 10 Beds
  • 12 Baths
  • 7,153 Sq Ft

  1589 Main St, Cavendish, VT 05142

  Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

  Kevin Barnes William Raveis Real Estate Vermont Properties

  1589 Main St, Cavendish, VT 05142
• 

  

  /19

  $224,000

  • Land
  • 68.5 Acres
  • $3,270 per Acre

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156

  Behold this rare opportunity to own 68 acres of pristine Vermont land located on a quiet, town-maintained dirt road in the peaceful hills of Springfield. This expansive parcel is a dream for outdoor enthusiasts—offering direct access to nature with miles of established trails, a diverse and healthy forest, and abundant wildlife. Bordering the beloved Muckross State Park—over 200 acres of

  Daire Gibney Barrett and Valley Associates Inc.

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156
• 

  

  /45

  $739,000

  • 4 Beds
  • 2.5 Baths
  • 2,663 Sq Ft

  490 W Hill Rd, Ludlow, VT 05149

  From mountain views to après-ski soaks in the hot tub, this home delivers the full Vermont lifestyle with ease. Located on one of Ludlow’s most coveted roads, this custom-built mountain retreat offers the perfect blend of quality, comfort, and convenience. Skip the village traffic and drive straight to the base of Okemo in just minutes! Thoughtfully designed and with so much to love, this

  Frank Provance Diamond Realty

  490 W Hill Rd, Ludlow, VT 05149
• 

  

  /60

  $4,850,000

  • 5 Beds
  • 6 Baths
  • 9,153 Sq Ft

  476 Salt Ash Rd, Plymouth, VT 05056

  Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondacks, known as The Point, and thoughtfully designed to reflect its inviting look and warm, rustic elegance. This 9,000+ square foot residence sits atop a knoll beside a lively creek with small waterfalls, creating a peaceful, natural soundtrack.The Great Room is the centerpiece of the home, with a soaring

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  476 Salt Ash Rd, Plymouth, VT 05056
• 

  

  /41

  $614,000

  • 3 Beds
  • 2 Baths
  • 1,908 Sq Ft

  530 West Rd, Barnard, VT 05031

  Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

  Dan Noble Snyder Donegan Real Estate Group

  530 West Rd, Barnard, VT 05031
• 

  

  /60

  $2,295,000

  • 4 Beds
  • 4.5 Baths
  • 6,548 Sq Ft

  657 Town Farm Rd, Ludlow, VT 05149

  61 Acre estate with sweeping views and open fields in Ludlow's prestigious South Hill area. Less than 10 minutes to the Okemo ski area and the Ludlow village amenities, this luxury home has received numerous updates in the last several years.Large updated eat-in country kitchen w/ wood cabinetry, stone countertops and updated stainless steel appliances. A gas fireplace with sitting room

  Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  657 Town Farm Rd, Ludlow, VT 05149
• 

  

  /57

  $1,199,000

  • 5 Beds
  • 4 Baths
  • 3,282 Sq Ft

  1873 North Rd, Bethel, VT 05032

  On the west-facing ridge of Barnard, Vermont’s fabled North Road, this ca. 1982 Cape enjoys panoramic long-range views of the Green Mountain Range to the west and North. With ten acres of fenced open pasture and a wood lot, a large, detached barn, and plenty of land to use, the property offers a range of possibilities. Expanded and improved by the current owners over the last 20 years, the house

  Richard Higgerson Higgerson & Company

  1873 North Rd, Bethel, VT 05032
• 

  

  /16

  $399,000

  • Land
  • 13.4 Acres
  • $29,776 per Acre

  00 N Hill Pent Rd, Ludlow, VT 05149

  Opportunity awaits with these two connected wooded building lots totaling 13.44 acres, offering easy access to the VAST snowmobile trail network. Located on a quiet, dead-end country road, this peaceful setting is ideal for those seeking a private getaway with four-season recreational opportunities right at your doorstep. Lot A is 4.67 acres and lot B is 8.77 acres. Both parcels include

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  00 N Hill Pent Rd, Ludlow, VT 05149
• 

  

  /30

  $650,000

  • 3 Beds
  • 3 Baths
  • 4,324 Sq Ft

  3630 Vt Route 103 N, Chester, VT 05143

  Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3630 Vt Route 103 N, Chester, VT 05143
• 

  

  /18

  $50,000

  • Land
  • 2.07 Acres
  • $24,155 per Acre

  0 E Ash Rd, Plymouth, VT 05056

  Welcome to Hawk East lot 2-20. This 2.07 acres lot is one of the closest lots to the Hawk Mountain Resort. There is a nice level area in the middle of the property that would make a nice building site. Easy access to Route 100 and only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 E Ash Rd, Plymouth, VT 05056
• 

  

  /52

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,800 Sq Ft

  248 Gird Lot Rd, Weathersfield, VT 05151

  Perched above the Connecticut River Valley with sweeping views to the New Hampshire mountains, this meticulously maintained five bedroom, four and a half bath home offers a rare opportunity just 30 minutes to Hanover, NH, Dartmouth College, and Dartmouth Hitchcock Medical Center. For medical professionals relocating to the Upper Valley, this property provides privacy, acreage, and panoramic views

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
• 

  

  /60

  $599,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  5100 Route 100, Plymouth, VT 05056

  (Das Grünebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

  Marni Rieger KW Vermont-Killington

  5100 Route 100, Plymouth, VT 05056
• 

  

  /20

  $250,000

  • Land
  • 28.5 Acres
  • $8,772 per Acre

  00 Chapel Hill Rd, Sharon, VT 05065

  Located on a class IV road, right after the end of the publicly maintained section of Chapel Hill Road, this 28.5 acre parcel has potential for a camp, off-grid home, or as a recreational getaway. Extensive work has been done to the road leading to the lot including widening the road and adding culverts and the Seller has roughed in a driveway to a level spot about 600 feet from the town

  Tami Sullivan Snyder Donegan Real Estate Group

  00 Chapel Hill Rd, Sharon, VT 05065
• 

  

  /15

  $139,900

  • Land
  • 2.58 Acres
  • $54,225 per Acre

  0 Cedar Dr, Ludlow, VT 05149

  Discover the perfect canvas for your dream home on this serene 2.5+/-acre lot, ideally located at the end of a cul-de-sac on Cedar Drive in Ludlow, VT. Nestled in a peaceful subdivision, this wooded parcel offers the privacy, natural beauty, and tranquility that define Vermont living. With power conveniently available at the street, this property is ready for your vision—whether that’s a mountain

  Katherine Burns William Raveis Real Estate Vermont Properties

  0 Cedar Dr, Ludlow, VT 05149
• 

  

  /51

  $649,000

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  35 Stevens Rd, Cavendish, VT 05142

  Winter, Spring, Summer or Fall, this is a bit of heaven for the nature lover! Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The back yard has lawn area with room for

  Betty McEnaney Diamond Realty

  35 Stevens Rd, Cavendish, VT 05142
• 

  

  /17

  $825,000

  • Land
  • 150 Acres
  • $5,500 per Acre

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091

  150 acres of recreational paradise! Absolute and total privacy! Enjoy long views of mountain peaks showing criss crossed ski trails, pristine cascading streams with mesmerizing waterfalls over large rock outcroppings, mature woodland which hasn't been logged in over 50 years, a fully equipped camper trailer with propane fired generator for off grid living and even a 4 wheeler outfitted with

  John Wetmore Wetmore Real Estate

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091
• 

  

  /36

  $349,000

  • Land
  • 10.56 Acres
  • $33,049 per Acre

  0 Valley View Dr, Ludlow, VT 05149

  Elevate Your Lifestyle at Summit Ridge - Tucked away in a private, gated community just minutes from the slopes of Okemo and our Lakes Region, this homesite is the perfect canvas for your mountain dream home. State wastewater permit for a four-bedroom home is in place. Imagine waking up to panoramic, long-range mountain views in every direction—serenity, space, and stunning scenery, all wrapped

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  0 Valley View Dr, Ludlow, VT 05149
• 

  

  /60

  $1,250,000

  • 6 Beds
  • 5.5 Baths
  • 5,790 Sq Ft

  49 Burton Rd, Weston, VT 05161

  “Meadow & Mountain View” is the Vermont home you’ve been waiting for! Situated just outside of the charming village of Weston, this impressive property offers one of the area’s most delightful and picturesque locations with fantastic views, beautiful grounds, and a warm and welcoming house designed so that you can relax and truly enjoy your Vermont Life. The inviting layout features classic New

  Claudia Harris Mary Mitchell Miller Real Estate

  49 Burton Rd, Weston, VT 05161
• 

  

  /12

  $399,000

  • Land
  • 4.73 Acres
  • $84,355 per Acre

  5209 5211 Willard Rd, Hartford, VT 05059

  We are pleased to present a rare opportunity to secure an estate-sized double lot in the highly desirable Upper Willard Road neighborhood of Quechee Lakes. Comprised of two thoughtfully assembled parcels totaling 4.73± acres, this offering provides both privacy and possibility in one of Vermont’s premier four-season resort communities. The current owner strategically combined these parcels to

  Richard Higgerson Higgerson & Company

  5209 5211 Willard Rd, Hartford, VT 05059
• 

  

  /33

  $549,000

  • Land
  • 20.2 Acres
  • $27,178 per Acre

  00 Long Hill Rd, Woodstock, VT 05071

  Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west. Located just minutes from South

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  00 Long Hill Rd, Woodstock, VT 05071
• 

  

  /11

  $135,000

  • Land
  • 1.19 Acres
  • $113,445 per Acre

  5417 Fletcher Ln, Hartford, VT 05059

  Located in the highly desirable Upper Willard Road neighborhood of Quechee Lakes, this 1.19-acre parcel offers an excellent opportunity to build your Vermont retreat in one of the region’s premier four-season communities. The gently sloping terrain provides flexibility for a homesite, either closer to Fletcher Lane or further back at a higher elevation toward the west end of the property. Recent

  Richard Higgerson Higgerson & Company

  5417 Fletcher Ln, Hartford, VT 05059
• 

  

  /25

  $115,000

  • Land
  • 10 Acres
  • $11,500 per Acre

  S-1C Great Roaring Brook Rd, Plymouth, VT 05056

  Ten-acre wooded parcel with potential views located near the top of Great Roaring Brook Rd. The topography is rolling too steep with multiple buildings sites, rock crop outs, and streams throughout. A wonderful opportunity to design and build your Vermont dream home. Located between Ludlow and Woodstock with equal distance to Killington and Okemo Ski areas. Close to Lake Rescue and Echo Lake for

  Terry Davis Williamson Group Sothebys Intl. Realty

  S-1C Great Roaring Brook Rd, Plymouth, VT 05056

Showing Results 161 - 200, Page 5 of 6