Windsor County VT Homes for Sale with Acreage

• 

  

  

  /57

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  3993 Royalton Hill Rd, South Royalton, VT 05068

  A one-of-a-kind Vermont retreat where thoughtful design, craftsmanship, and landscape converge. This 3-bedroom, 2-bath home has been expanded and fully renovated including a new roof, state-of-the-art heating system, and solid hardwood flooring. Every surface has been custom-finished, blending modern comfort with artistic mid-century modern influences for a home that feels more curated than

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  3993 Royalton Hill Rd, South Royalton, VT 05068
• 

  

  

  /60

  $3,550,000

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

  657 Town Farm Rd, Ludlow, VT 05149

  Rare opportunity to own one of the largest privately owned parcels within minutes of Okemo! 163+ Acre estate with sweeping views and open fields in Ludlow's prestigious South Hill area. Under 10 minutes to Okemo, 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

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

  657 Town Farm Rd, Ludlow, VT 05149
• 

  

  

  /16

  $3,150,000

  • Land
  • 506 Acres
  • $6,225 per Acre

  00 Marsh Cross Rd, Andover, VT 05143

  Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence. This land's historical roots run deep, originally belonging to the Marsh

  Story Jenks LandVest, Inc/Woodstock

  00 Marsh Cross Rd, Andover, VT 05143
• 

  

  

  /16

  $74,500

  • Land
  • 16.24 Acres
  • $4,587 per Acre

  TBD Farrar Rd, Chester, VT 05143

  Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

  Erin Kendall EXP Realty

  TBD Farrar Rd, Chester, VT 05143
• 

  

  

  /20

  $249,000

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  574 Willard Rd Unit 4A, Quechee, VT 05059

  Experience the ultimate Vermont lifestyle in this stunning end-unit condominium, where modern elegance meets trailside serenity. This home offers a rare sense of privacy, featuring a spacious deck that wraps around the the condo, providing a front-row seat to the soothing sounds of the nearby brook and the quiet beauty of the surrounding woods. Inside, the residence is completely move-in ready

  Linda Hicks Quechee Lakes Real Estate Center

  574 Willard Rd Unit 4A, Quechee, VT 05059
• 

  

  /47

  $149,000

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft

  49 Clay Hill Rd, Hartland, VT 05048

  Partially finished circa 1998 26' x 24' ranch house on 2 lots totalling 1.76+/- acres. This fixer-upper has been lived in year round since its construction but never fully finished. The space consists of a kitchen that opens into a single main room being used as a living room, bedroom and dining area. Both the interior and exterior wall surfaces need finishing in places. The interior needs

  Steve Schoppmeyer BHG Masiello Brattleboro

  49 Clay Hill Rd, Hartland, VT 05048
• 

  

  /60

  $889,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 3,310 Sq Ft

  201 Spruce Dr, Chester, VT 05143

  Situated on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home offers effortless access to Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area, and is being sold turnkey. Designed for those who value both comfort and connection to the outdoors, this property is a true four-season retreat. In winter, enjoy world-class skiing

  Mendi Michael Engel & Völkers Okemo

  201 Spruce Dr, Chester, VT 05143
• 

  

  /60

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,205 Sq Ft

  688 Hidden Heights Rd, Chester, VT 05143

  Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the

  Joseph Karl William Raveis Real Estate Vermont Properties

  688 Hidden Heights Rd, Chester, VT 05143
• 

  

  /45

  $1,299,000

  • 8 Beds
  • 5 Baths
  • 3,814 Sq Ft

  7030 U S 4, Bridgewater, VT 05034

  Situated between historic Woodstock Vermont and the ski slopes of Killington, 7030 US Route 4 provides easy access to the best amenities of the area. The Property has two separate spaces, a standalone two-level garage with ample storage area below, and sits on 6 acres with direct river access. The "Apartment” first floor has an open design with a kitchen, living area, and tucked away bathroom.

  Eric Benvenuti

  7030 U S 4, Bridgewater, VT 05034
• 

  

  /31

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  1397 Popple Dungeon Rd, Chester, VT 05143

  Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved

  Daire Gibney Barrett and Valley Associates Inc.

  1397 Popple Dungeon Rd, Chester, VT 05143
• 

  

  /60

  $1,245,000

  • 3 Beds
  • 4 Baths
  • 2,971 Sq Ft

  42 Deerfield Dr, Ludlow, VT 05149

  Welcome to South Hill Overlook on Deerfield Drive. This perfectly situated, idyllic country home boasts a beautifully appointed interior and sweeping views of Okemo and the surrounding mountains, with a sophisticated three-bedroom, four-bath contemporary design that blends luxury and comfort-ideal as either a primary residence or a vacation retreat. This sun-filled home was built by one of the

  Kevin Barnes William Raveis Real Estate Vermont Properties

  42 Deerfield Dr, Ludlow, VT 05149
• 

  

  /60

  $699,000

  • 4 Beds
  • 4 Baths
  • 2,578 Sq Ft

  78 Coopers Trace, Plymouth, VT 05056

  Set in Hawk Resort, conveniently located between Killington and Okemo, this well-kept four-bedroom, four-bath home offers privacy, space, and easy access to Vermont’s best outdoor recreation. The main level features an open layout with cathedral ceilings, wide pine floors, and excellent natural light from large windows and skylights. A renovated kitchen and fresh interior paint give the home a

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  78 Coopers Trace, Plymouth, VT 05056
• 

  

  /16

  $299,000

  • Land
  • 8.1 Acres
  • $36,914 per Acre

  0 Fay Ln Unit 7226 and 7227, Hartford, VT 05059

  Discover the serene beauty of Vermont from this expansive 8.1-acre parcel along Fay Lane! The lot is located in the esteemed Quechee Lakes Landowners Association (QLLA). Quechee Lakes is a private, full-amenity resort with two championship golf courses, a private lake and beach, tennis and pickleball, indoor/outdoor pools, a fitness center, and a racquet sport complex. In winter, enjoy downhill

  Brooks Reavill

  0 Fay Ln Unit 7226 and 7227, Hartford, VT 05059
• 

  

  /18

  $259,900

  • 4 Beds
  • 1 Bath
  • 1,738 Sq Ft

  1009 Vermont 131, Weathersfield, VT 05156

  GREAT LOCATION - Check out this Circa 1840's Farmhouse with attached Garage and Shed on 3.98 acres with open meadows and woods. First floor features an Eat-In Kitchen, Full Bathroom, Laundry Room, Living Room, Bedroom and Den/Dining Room with Pellet Stove. Upstairs you'll find 4 Bedrooms that need some cosmetic work. Just 3/4 mile from Exit 8 for easy commute to Upper Valley and Short drive to

  Don Chabot Town and Country Realty

  1009 Vermont 131, Weathersfield, VT 05156
• 

  

  /60

  $800,000

  • 7 Beds
  • 4.5 Baths
  • 4,733 Sq Ft

  107 Baker Rd, Springfield, VT 05156

  Welcome to this spacious and beautifully expanded Gambrel-style home, nestled on a breathtaking 9.55-acre property with sweeping mountain views in the heart of Springfield, Vermont. Combining classic New England charm with thoughtful modern upgrades, this property is more than just a home; it's a vibrant lifestyle. The main house, built in 1955, was thoughtfully enhanced with a large addition in

  Jeremy Collins Ridgeline Real Estate

  107 Baker Rd, Springfield, VT 05156
• 

  

  /60

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 2,794 Sq Ft

  34 Midsomer Meadows Ln, Woodstock, VT 05091

  Welcome to Starry Hill, a fully furnished, handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock. This 3-bedroom, 2.5 bath home was built over 4 years by a family of loggers and master craftsmen. Used recently as an AirBnB rental and ready for occupancy. This exceptional home features Eastern white pine walls, hemlock structural beams, and

  John Bassette Bassette Real Estate Group

  34 Midsomer Meadows Ln, Woodstock, VT 05091
• 

  

  /58

  $3,490,000

  • 4 Beds
  • 4.5 Baths
  • 2,894 Sq Ft

  1726 Skitchewaug Trail, Springfield, VT 05156

  A circa 1734 Cape, displaying museum quality authentic detailing, in a setting worthy of a Vermont Life Magazine cover! Originally sited in N.H., the Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The interior seamlessly blends early New England architectural features with benefits of contemporary design amenities.

  John Wetmore Wetmore Real Estate

  1726 Skitchewaug Trail, Springfield, VT 05156
• 

  

  /28

  $3,300,000

  • 3 Beds
  • 4.5 Baths
  • 3,682 Sq Ft

  249 Sawyer Rd, Woodstock, VT 05091

  Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

  Andrew Bustin LandVest, Inc/Woodstock

  249 Sawyer Rd, Woodstock, VT 05091
• 

  

  /44

  $439,000

  • 2 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  339 Ranney Rd, Stockbridge, VT 05772

  Take a look at this home in central Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 2 acre lot with plenty of sun and space for pets, gardens or greenhouses. An adjoining 1 acre house lot can be purchased for an additional 30k if interested now. This Stockbridge home has an extra living apartment below- accessible by a separate driveway. It provides

  Risa Mornis Covered Bridge RE

  339 Ranney Rd, Stockbridge, VT 05772
• 

  

  /17

  $125,000

  • Land
  • 10.3 Acres
  • $12,136 per Acre

  167 Leons Ln, Sharon, VT 05068

  Discover a rare development opportunity tucked away in the Vermont woods. Situated on a quiet, dead-end road, this stunning 10+ acre parcel offers the perfect canvas for your dream mountain sanctuary. The land features a serene mix of deciduous and evergreen trees and slopes upward, offering excellent potential for a home with a walk-out basement. While a rustic cabin shell currently sits on the

  Holly Hall Hall Collins Real Estate Group

  167 Leons Ln, Sharon, VT 05068
• 

  

  /11

  $2,200,000

  • Land
  • 153.73 Acres
  • $14,311 per Acre

  0 Vermont 106, Reading, VT 05062

  Tucked away near the sought-after communities of Woodstock, West Windsor, and Ludlow, this untouched parcel invites endless possibilities. From its elevated perch, it offers sweeping views of Mt. Ascutney and the Connecticut River Valley in every direction. The Northern New England forested landscape is crisscrossed with trails, old roads, and natural springs, perfect for exploration. There are

  Laird Bradley Williamson Group Sothebys Intl. Realty

  0 Vermont 106, Reading, VT 05062
• 

  /2

  $159,000

  • Land
  • 25 Acres
  • $6,360 per Acre

  0 U S 5, Norwich, VT 05055

  Norwich building lot opportunity / land parcel very near retail businesses, Norwich Farmers Market and office areas. Don't miss this chance to build your single family home or possibly a multifamily project / senior living home in the Palmer Court area of Norwich, VT. A mostly wooded 25 +/- acre near town lot located at the end of Palmer Court. This property is also adjacent to an additional 8.52

  Alex DeFelice The Clerkin Agency, P.C.

  0 U S 5, Norwich, VT 05055
• 

  /2

  $221,000

  • Land
  • 8.52 Acres
  • $25,939 per Acre

  0 Barrister Dr Unit 3, Hartford, VT 05001

  In-town building lot opportunity! Don't miss this chance to build your single family home or possibly a multifamily project in the Barrister Drive area of Wider, VT. A nice 8.52 +/- acre in-town lot located at the end of Palmer Court or Barrister Drive. This property is adjacent to an additional 25 +/- acre Norwich, VT. lot that is also for sale at $159,000. and could possibly be used for an

  Alex DeFelice The Clerkin Agency, P.C.

  0 Barrister Dr Unit 3, Hartford, VT 05001
• 

  

  /24

  $646,500

  • Land
  • 37.85 Acres
  • $17,081 per Acre

  0 South Rd, Woodstock, VT 05071

  Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream.About two miles to GMHA and South Woodstock village, one mile to VAST trail.40 minutes to skiing at Killington, less to Okemos. Seven miles into Woodstock Village.

  Matthew Spittle Vermont Horse Country Real Estate

  0 South Rd, Woodstock, VT 05071
• 

  

  /24

  $675,000

  • Land
  • 41.9 Acres
  • $16,110 per Acre

  8 Grout Rd, Hartland, VT 05048

  Rare, one-of-a-kind land offering with close proximity to Quechee and Hartland.Beautiful building site with Western exposure and exceptional views to the West and North. Pastureland and open meadows for any farming and cultivation needs. Easy construction for additional out buildings or subdivision is possible.Road frontage on Grout Road and the Quechee Hartland road.Private, with

  Charles Bacon Quechee Lakes Real Estate Center

  8 Grout Rd, Hartland, VT 05048
• 

  

  /21

  $119,000

  • Land
  • 3.95 Acres
  • $30,127 per Acre

  00 Barber Ln, Hartland, VT 05048

  Discover the ideal backdrop for your next build on this peaceful slice of Vermont countryside. Positioned on a gentle rise, the land offers elevated views and a serene natural setting surrounded by mature landscape. A privately maintained road leads you in, providing a quiet approach and a sense of retreat. This location strikes a perfect balance—rural charm with quick access to daily

  Chelsea Bevis KW Vermont Woodstock

  00 Barber Ln, Hartland, VT 05048
• 

  

  /57

  $565,000

  • 4 Beds
  • 2 Baths
  • 2,212 Sq Ft

  298 Jenneville Rd, Windsor, VT 05089

  PRICE REDUCED! Welcome to "Valley Brook Farm", an historic cape in the middle of horse country on 12.92 acres with barns, rolling & level pasture, a swimming pond, and brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 cape offers the warmth of wide pine floors, post-and-beam character,

  John Bassette Bassette Real Estate Group

  298 Jenneville Rd, Windsor, VT 05089
• 

  

  /17

  $250,000

  • Land
  • 3.06 Acres
  • $81,699 per Acre

  0 Burdock Ln Unit 5070352, Ludlow, VT 05149

  Welcome to an exceptional opportunity to create your ideal Vermont retreat in the highly sought-after Ludlow area — home to world-class skiing, pristine lakes, and year-round adventure. Lot #7 offers 3.06+/- acres a rare combination of natural beauty, privacy, and convenience, complete with underground power installed and a state-approved 4-bedroom wastewater permit. Bordering 488 acres of

  Heather Ashline BHHS Verani Upper Valley

  0 Burdock Ln Unit 5070352, Ludlow, VT 05149
• 

  

  /36

  $95,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149

  Experience Vermont's Premier Mountain Living Without Full Ownership Costs. Step directly onto Okemo's slopes from your slopeside retreat at Jackson Gore. This condo-tel quarter-share gives you deeded ownership of 13 weeks annually (25% of the year)—at a fraction of the cost of whole ownership. You own one of four deeded interests in this unit. You receive every fourth week on a rotating schedule,

  Rachael Rogala Lange & Lange

  224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149
• 

  

  /58

  $485,000

  • 8 Beds
  • 1 Bath
  • 3,500 Sq Ft

  1254 U S 5, Springfield, VT 05156

  Welcome to the former Danforth Inn! Take a trip back in time to 1780 as you look at this extremely original old building that was built in Weathersfield Bow in 1780 by Gideon Lyman. In 1789 Joseph Danforth moved to the Bow and he leased and then bought the Inn, changing the name to the Danforth Inn. This property will need some love, but it has never been spoiled in its originality, and it's just

  Glenn Olney Barrett and Valley Associates Inc.

  1254 U S 5, Springfield, VT 05156
• 

  

  /14

  $289,000

  • 2 Beds
  • 2.5 Baths
  • 1,475 Sq Ft

  106 Contro Rd, Chester, VT 05143

  Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

  Christine Lewis Brattleboro Area Realty

  106 Contro Rd, Chester, VT 05143
• 

  

  /3

  $159,000

  • Land
  • 5 Acres
  • $31,800 per Acre

  00 Contro Rd, Chester, VT 05143

  There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town

  Christine Lewis Brattleboro Area Realty

  00 Contro Rd, Chester, VT 05143
• 

  

  /41

  $1,576,000

  • 9,455 Sq Ft

  14 Summarsell Dr Unit 16, Hartland, VT 05048

  This charming converted farmstead features two primary buildings on one parcel, combining classic Vermont character with solid investment returns. The property offers a diverse mix of one-, two-, and four-bedroom apartments, plus one commercial unit currently leased to a local bath and body company. Additional income comes from a three-bay garage, a shed, and a storage container — all fully

  Loren Wehmeyer Tesla Realty Group, LLC

  14 Summarsell Dr Unit 16, Hartland, VT 05048
• 

  

  /8

  $590,000

  • Land
  • 61.49 Acres
  • $9,595 per Acre

  00 Wild Apple Rd, Pomfret, VT 05067

  One of the most sought-after locations in the Woodstock area, this 61-acre property is accessed off of Wild Apple Road with a building site oriented to the south and east. At 1,600 feet in elevation, it enjoys sweeping views of Killington, Mount Ascutney, and the surrounding hills. The land offers complete privacy with a blend of woodlands, open fields, a stream, and a pond site. Bordering the

  Story Jenks LandVest, Inc/Woodstock

  00 Wild Apple Rd, Pomfret, VT 05067
• 

  

  /24

  $452,600

  • 2,915 Sq Ft

  282 Skunk Hollow Rd, Hartland, VT 05048

  Two buildings on one parcel in desirable Hartland, Vermont! This flexible and well-maintained property includes a single-family home and a duplex, offering outstanding potential for owner occupancy, multi-generational living, or investment income. Ideally situated just 25 minutes from Hanover, NH, and 10 minutes from Woodstock, VT, this location provides the perfect balance of convenience and

  Loren Wehmeyer Tesla Realty Group, LLC

  282 Skunk Hollow Rd, Hartland, VT 05048
• 

  

  /49

  $715,000

  • 4 Beds
  • 3.5 Baths
  • 2,654 Sq Ft

  760 E Ash Rd, Plymouth, VT 05056

  Spacious Hawk Resort Home with Scenic Views Enjoy the perfect blend of comfort, space, and mountain charm in this inviting Hawk home. Designed for family gatherings and entertaining, the generous open-concept living area features a beautiful fieldstone fireplace and updated greenhouse windows that bring in natural light and picturesque views. The primary suite offers a cozy fireplace, private

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  760 E Ash Rd, Plymouth, VT 05056
• 

  

  /10

  $45,000

  • Land
  • 5.6 Acres
  • $8,036 per Acre

  0 Va Cutoff Rd, Hartford, VT 05001

  A unique property for imaginative business owners with commercial or industrial uses in mind. The property is a narrow strip in between I-89 and the Hartford Fire Department, very close to the VA Hospital, where both town water and sewer are available. The southern 3.5 acres (approximately) are covered by class 3 wetlands and cannot be used. The remaining 2 acres also have wet areas, however

  David White OwnerEntry.com

  0 Va Cutoff Rd, Hartford, VT 05001
• 

  

  /9

  $175,000

  • Land
  • 5.01 Acres
  • $34,930 per Acre

  476 Missing Link Rd, Springfield, VT 05156

  5 acres of magical Ct River frontage. This site boasts 2 wide open fields. The septic design for a 5 bdrm septic is in the first field. The seller has obtained permission from the state for a driveway curb cut (Missing Link Rd, is State Rte 5) The land sits 80 ft above the river, so flooding is not an issue but you'll have the most peaceful, private views of the water. There are 2 steep walking

  Victoria Woods Brattleboro Area Realty

  476 Missing Link Rd, Springfield, VT 05156
• 

  

  /3

  $220,000

  • Land
  • 50.45 Acres
  • $4,361 per Acre

  0 Missing Link Rd, Springfield, VT 05156

  Sitting high above Rte 5, this large parcel has a prime view out over the Connecticut River. There's a septic permit in place for a 5 bedroom home. You'll need to improve the old logging road to gain access to the top but once you do, there are 50 acres to explore. Enroll in the Use Value Program to reduce your taxes!

  Victoria Woods Brattleboro Area Realty

  0 Missing Link Rd, Springfield, VT 05156
• 

  

  /41

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  115 Prior Rd, Cavendish, VT 05142

  Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral

  Glenn Olney Barrett and Valley Associates Inc.

  115 Prior Rd, Cavendish, VT 05142

Showing Results 81 - 120, Page 3 of 6