Windsor County VT Homes for Sale

• 

  

  

  /30

  $169,500

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  25 Wilder Ln, Bethel, VT 05032

  Welcome to this spacious 3-bedroom, 2-bath mobile home on .65 acres of owned land in the lovely town of Royalton, Vermont. Built in 1997, this place offers 1,140 square feet of comfortable, single-level living that perfectly blends convenience, affordability, and peaceful tranquility. Nestled on a quiet dead-end road, the home provides great privacy while still being close to local amenities and

  Jeremy Collins Ridgeline Real Estate

  25 Wilder Ln, Bethel, VT 05032
• 

  

  

  /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
• 

  

  

  /36

  $369,000

  • 5 Beds
  • 1 Bath
  • 2,243 Sq Ft

  2029 N Hill Rd, Chester, VT 05143

  Come, enjoy the quiet charm of Andover in this inviting, private Vermont home—perfect for year-round living or a peaceful getaway. Nestled among evergreens with beautiful snowy views, this property offers easy access to Okemo Mountain, and is also close to Stratton, Magic, and Bromley for skiing, riding, and four-season adventure. Snowmobile enthusiasts will love the nearby VAST trails, and the

  Daire Gibney Barrett and Valley Associates Inc.

  2029 N Hill Rd, Chester, VT 05143
• 

  

  /17

  $299,000

  • 1 Bed
  • 1 Bath
  • 320 Sq Ft

  103 Bear Hill Rd W, Ludlow, VT 05149

  Location, location, location! This recently built 320 sq. ft. tiny house sits on 2.34 stunning acres framed by majestic white birch trees, wooded privacy, and a partial view of Okemo Mountain. Completed in 2024, the home features an open floor plan with warm pine walls, a cozy combined living/bedroom area a functional kitchen, a 3⁄4 bath, and an additional 128 sq. ft. bonus loft—ideal for extra

  John Napier TPW Real Estate

  103 Bear Hill Rd W, Ludlow, VT 05149
• 

  

  /10

  $479,000

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  13 Bullard St Unit 15, White River Junction, VT 05001

  Fully rented duplex with strong rental history. One side has been completely remodeled and updated with slate flooring. vinyl planking and carpet in the bedrooms. Tile shower and granite countertops and new windows. Both sides have a full basement with washer and dryers. one with a boiler and one with a hot air furnace. Nice private back yard. Both driveways have recently been black topped.

  David White OwnerEntry.com

  13 Bullard St Unit 15, White River Junction, VT 05001
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  /53

  $390,000

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft

  531 Main St, Chester, VT 05143

  Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area

  Katherine Burns William Raveis Real Estate Vermont Properties

  531 Main St, Chester, VT 05143
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  /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
• 

  

  /60

  $799,000

  • 7 Beds
  • 7 Baths
  • 4,581 Sq Ft

  7137 US Route 4, Bridgewater, VT 05034

  Welcome to the historic Bridgewater Inn — a rare, turn-key Vermont property perfectly positioned between Woodstock Village, Killington Resort, and Okemo Mountain. This unique offering features a spacious 3-bedroom, 3-bath main home along with four fully equipped guest suites, creating exceptional flexibility for full-time living, multi-generational use, or continued short-term rental success. The

  Benjamin Cote EXP Realty

  7137 US Route 4, Bridgewater, VT 05034
• 

  

  /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

  $595,000

  • 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
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  /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
• 

  

  /3

  $170,000

  • Land
  • 10.04 Acres
  • $16,932 per Acre

  00 Will Dean Rd, Springfield, VT 05156

  Nice piece of land with some selected clearing done but more could be done with the potential of views. Land is both clear and wooded, level and sloping. Located on a quiet gravel road with a mix of single-family homes and small farms it is the perfect reflection of rural Vermont. Just minutes to I91and downtown Springfield makes this a great spot to set down roots.

  

  Julie Buffum

  Buffum Realty

  (802) 327-7566

  00 Will Dean Rd, Springfield, VT 05156
• 

  

  /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
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  /33

  $299,000

  • 2,702 Sq Ft

  41 Vt Route 103 S, Chester, VT 05143

  Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. Presently, all three units are vacant. Easy to show! There is good

  Glenn Olney Barrett and Valley Associates Inc.

  41 Vt Route 103 S, Chester, VT 05143
• 

  

  /58

  $2,950,000

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

  48 Alpine Way Unit D-1, Ludlow, VT 05149

  Show Stopper—this five-bedroom slopeside townhouse sits just steps from the trails and offers three private suites across three levels of beautifully curated living space. Completely reimagined by a talented local designer, it features an organic palette, thoughtful details, and a true move-in-ready feel—just hang your artwork and your skis. The chef’s kitchen showcases a Dekton waterfall

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  48 Alpine Way Unit D-1, Ludlow, VT 05149
• 

  

  /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

  $399,000

  • 5 Beds
  • 3.5 Baths
  • 2,200 Sq Ft

  109 Park Row, Rochester, VT 05767

  The Richard Steele Hubbard home, ideally situated just off the park in the charming village of Rochester, Vermont, is a fine example of the American Foursquare style popular in the late 19th and early 20th centuries. This five-bedroom residence retains many period details, including handcrafted woodwork, hardwood floors, coffered ceilings, stamped tin, and decorative moldings. Thoughtful updates

  Kyle Kershner Killington Pico Realty

  109 Park Row, Rochester, VT 05767
• 

  

  /42

  $665,000

  • 8 Beds
  • 6 Baths
  • 6,960 Sq Ft

  61 Depot St, Hartford, VT 05001

  Exceptional Investment or Conversion Opportunity in the Heart of Wilder Approved for conversion into four residential units and two commercial office spaces, this well-maintained six-unit office building offers outstanding flexibility for investors or owner-occupants. The proposed plan includes two street-level commercial suites with four apartments above, creating a desirable mixed-use property.

  Katie Ladue Gilbert KW Vermont Woodstock

  61 Depot St, Hartford, VT 05001
• 

  

  /60

  $1,300,000

  • 4 Beds
  • 5 Baths
  • 3,195 Sq Ft

  125 Shurtleff Ln, Woodstock, VT 05091

  Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor

  Keri Cole Williamson Group Sothebys Intl. Realty

  125 Shurtleff Ln, Woodstock, VT 05091
• 

  

  /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
• 

  

  /31

  $299,000

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft

  29 Markham Ln, Weston, VT 05161

  This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

  Catherine Cairns Maple Leaf Realty

  29 Markham Ln, Weston, VT 05161
• 

  

  /41

  $999,500

  • 3,218 Sq Ft

  1 Depot St, Hartford, VT 05001

  Excellent Upper Valley investment opportunity! This well-maintained six-unit multifamily property features a desirable mix of 3 one-bedroom apartments and 3 two-bedroom apartments, ideally situated in the heart of Wilder. The property sits directly across from the bus stop and offers convenient access to major employers and amenities — just 9 minutes (4.2 miles) from Dartmouth College and 17

  Loren Wehmeyer Tesla Realty Group, LLC

  1 Depot St, Hartford, VT 05001
• 

  

  /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
• 

  

  /45

  $1,100,000

  • 4 Beds
  • 4 Baths
  • 2,640 Sq Ft

  307 Remick Rd, White River Junction, VT 05001

  Nestled at the end of a quiet dead-end road, this 68-acre private homestead offers exceptional privacy, timeless New England charm, and direct access to over 560 acres of town-owned land—the Hurricane Forest and Hurricane Wildlife Refuge. With conservation land on two sides, this property is a rare blend of seclusion, natural beauty, and convenience—a one mile drive to the intersection of RT 89

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  307 Remick Rd, White River Junction, VT 05001
• 

  

  /37

  $529,000

  • 5 Beds
  • 5 Baths
  • 3,880 Sq Ft

  514 1st Ave, Chester, VT 05143

  Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals,

  Daire Gibney Barrett and Valley Associates Inc.

  514 1st Ave, Chester, VT 05143
• 

  

  /40

  $795,000

  • 6 Beds
  • 9 Baths
  • 4,744 Sq Ft

  19 Huntington Place, Rochester, VT 05767

  Imagine living in an 1806 home on a Vermont green. Located in the heart of the Green Mountains in the quaint town of Rochester, along the scenic Route 100 corridor. The property is currently a classic Vermont Inn with a chef-owned restaurant and tavern with lovely accommodations. Easily refurnished for private use. The home sits atop the Rochester Green. The village features galleries, shops, and

  Kate Cassidy Four Seasons Sotheby's Int'l Realty

  19 Huntington Place, Rochester, VT 05767
• 

  

  /9

  $249,000

  • 8 Beds
  • 4 Baths
  • 3,312 Sq Ft

  715 Giddings St, Springfield, VT 05150

  This Unique property features a large 3 unit building all featuring 2 bedrooms and 1 bathroom, with an additional carriage house with 2 bedrooms and 1 bathroom aswell. With a new heating system replaced in 2023 and many other key updates.

  Thaddeus Abare Barrett and Valley Associates Inc.

  715 Giddings St, Springfield, VT 05150
• 

  

  /56

  $699,000

  • 3 Beds
  • 2 Baths
  • 2,542 Sq Ft

  333 Music Mountain Rd, Stockbridge, VT 05772

  Nestled on a hilltop above scenic Music Mountain Road, this exceptional architect-designed home offers a private, sunny setting with breathtaking long-range views. The open floor plan provides one-level living ideal for every lifestyle, with radiantly heated white oak floors, a striking carved-oak mantel fireplace, and French doors framing the mountain panorama. The chef’s kitchen features

  Kyle Kershner Killington Pico Realty

  333 Music Mountain Rd, Stockbridge, VT 05772
• 

  

  /5

  $249,000

  • 4 Beds
  • 4 Baths
  • 2,767 Sq Ft

  3 Wall St, Springfield, VT 05156

  This property is a great source of revenue, with a good sound structure and well maintained utilities this property can serve as a great investment. Within walking distance to down town Springfield where you can find groceries, shops, restaurants and more.

  Thaddeus Abare Barrett and Valley Associates Inc.

  3 Wall St, Springfield, VT 05156
• 

  

  /11

  $39,999

  • Land
  • 1 Acre
  • $39,999 per Acre

  341 Seavers Brook Rd, Springfield, VT 05156

  Easy building lot in a nice neighborhood in Springfield. Near the road roughly half of the property is flat with some clearing. This was actually a former home site, however the building was lost in a fire. Beyond the flat area (about 90 feet in) the topography rises up steeply and it would be difficult to build beyond this point. There is an old septic system on the property however it would

  David White OwnerEntry.com

  341 Seavers Brook Rd, Springfield, VT 05156
• 

  

  /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
• 

  

  /37

  $102,000

  • 2 Beds
  • 3 Baths
  • 1,367 Sq Ft

  617/619 Qtr I Adams House, Ludlow, VT 05149

  Adams House Unit 617/619 Qtr.I : Quarter OwnershipExperience mountain comfort in this spacious 2-bedroom, 3-bath slope-facing condominium that sleeps eight. The primary bedroom features a king bed and ensuite bathroom. The main living area includes a full kitchen, a cozy gas fireplace, a sleep sofa, and a convenient guest bathroom. The lockout side offers two queen beds and a private

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  617/619 Qtr I Adams House, Ludlow, VT 05149
• 

  

  /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

Showing Results 121 - 160, Page 4 of 10