Windsor County VT Homes for Sale

• 

  

  

  /53

  $675,000

  • 3 Beds
  • 3 Baths
  • 2,916 Sq Ft

  133 Rousseau Rd, Royalton, VT 05068

  Extraordinary 9.93-acre property perched high above the charming village of Royalton, offering breathtaking panoramic views of central Vermont and beyond. On clear days, enjoy sweeping vistas stretching from Camel's Hump and Mount Mansfield to Mount Washington and New Hampshire's Presidential Range. Built in 2021, this thoughtfully designed home features an open-concept floor plan filled with

  Kyle Kershner Killington Pico Realty

  133 Rousseau Rd, Royalton, VT 05068
• 

  

  

  /14

  $845,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  234 Randall Rd, Wood Stock, VT 05091

  Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm

  Wade Treadway Wade I Treadway Real Estate

  234 Randall Rd, Wood Stock, VT 05091
• 

  

  

  /48

  $319,000

  • 4 Beds
  • 3 Baths
  • 3,548 Sq Ft

  16 Furnace St, Springfield, VT 05156

  Wonderfully renovated home with incredible income potential! This property features a fully updated, separate entrance 1-bedroom, 1-bathroom unit with its own electrical meter (shared baseboard heat between both sides). Market data suggests similar units in the area can command around $750/month in rent. For an owner-occupant, leveraging this 1-bed unit could significantly lower your net monthly

  Franchesca Collins Hall Collins Real Estate Group

  16 Furnace St, Springfield, VT 05156
• 

  

  

  /45

  $599,999

  • 6 Beds
  • 5 Baths
  • 4,184 Sq Ft

  49 Pleasant St, Ludlow, VT 05149

  If you are a skier, this is your hop-on-the shuttle to Okemo location. If you want to park your car and walk to restaurants and shops, this is a great home base to scoot out from. If you want to generate rental income, this is a property that can allow you to have your cake and eat it too. An easy keeper, without a lot of landscape to take care of, this large residence has hardwood floors and

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  49 Pleasant St, Ludlow, VT 05149
• 

  

  

  /38

  $413,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,888 Sq Ft

  273 Route 5 N, Windsor, VT 05089

  Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and

  Allison Griep BHHS Verani Upper Valley

  273 Route 5 N, Windsor, VT 05089
• 

  

  /56

  $3,650,000

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

  348 Turtle Hill Rd, Ludlow, VT 05149

  Set high with vistas of southern Vermont's valleys and mountains, "The Barn" is a remarkable custom timber frame retreat where exceptional craftsmanship meets breathtaking natural beauty. Completed in 2023 after two years of thoughtful design and construction, this residence was created to be a place of gathering, connection, and lasting memories for generations to come.Privately situated on

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  348 Turtle Hill Rd, Ludlow, VT 05149
• 

  

  /4

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 2,334 Sq Ft

  72 Wood Rd, Hartford, VT 05001

  US Route 4 in Vermont - the east/west corridor from I-89 and the Killington Ski Area. Highway frontage between Quechee and Woodstock, VT. Minutes from Dartmouth College in Hanover, NH; near the intersection of I-89 and 91 at the Connecticut River; also close to Northern New England’s major DH Medical complex and Cancer Center in Lebanon, NH, as well as the VA Hospital in White River Junction. 1.5

  Terry Boone Bassette Real Estate Group

  72 Wood Rd, Hartford, VT 05001
• 

  

  /47

  $749,000

  • 4 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  36 Lower IV Unit 48B, Ludlow, VT 05149

  This popular Sachem floor plan at the Okemo Trailside community is ready for new owners. Four bedrooms and two and a half baths across three levels, with a very recent remodel. It features a light, bright open floor plan, a beautifully updated kitchen with plenty of counter space and new appliances, a breakfast bar, a dining area with sliders off the deck, and a living room with a cathedral

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  36 Lower IV Unit 48B, Ludlow, VT 05149
• 

  

  /3

  $199,000

  $21K PRICE DROP

  • Land
  • 50.45 Acres
  • $3,944 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
• 

  

  /52

  $589,000

  • 2 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  14 Sterling Springs Dr, White River Junction, VT 05001

  A prize location situated at the top of Sterling Springs Drive with views to the hills. This light filled home has an open floor plan allowing for creative use of spaces. Many features include a generous sized primary bedroom with two walk-in closets, and a recently renovated ensuite bathroom. New flooring was added in a section of the main level. The second floor provides a bedroom and full

  Berna Rexford Four Seasons Sotheby's Int'l Realty

  14 Sterling Springs Dr, White River Junction, VT 05001
• 

  

  /16

  $129,900

  • 3 Beds
  • 2 Baths
  • 2,321 Sq Ft

  31 Amsden Hollow Rd, Perkinsville, VT 05151

  Older farmhouse looking for someone to bring it back to what it once was currently has 3-4 bedrooms, two baths, two kitchens, level lot, shed in the front yard area and a brook in the back yard area.

  April Shepard Twin State Realty LLC

  31 Amsden Hollow Rd, Perkinsville, VT 05151
• 

  

  /36

  $399,000

  $80K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,094 Sq Ft

  75 Naulahka Ln, Hartford, VT 05059

  This Quechee retreat feels like a tree house. Combining three lots provides a level of privacy that is becoming increasingly rare in the Upper Valley, and the vertical layout makes excellent use of that wooded backdrop.By placing the Great Room behind two large picture windows, the design creates a seamless visual transition between the interior and the forest canopy.With a bedroom and full bath

  Linda Hicks Quechee Lakes Real Estate Center

  75 Naulahka Ln, Hartford, VT 05059
• 

  

  /5

  $850,000

  • Land
  • 1.47 Acres
  • $578,231 per Acre

  97 Valley View Rd, Woodstock, VT 05091

  The justifiably proud owner of this property points out these features: Potential "Barnominium." Conveniently located just 1/4 mile from Woodstock Village town line and just 40 minutes from Killington Ski area. Built for an auto collection. Full bathroom, blown in insulation in ceiling, foam spray insulation in walls (with bug mesh in walls.) 3/4" sheet rock! All electrical is done in 3/4'

  John Wetmore Wetmore Real Estate

  97 Valley View Rd, Woodstock, VT 05091
• 

  

  /22

  $1,490,950

  New Construction $421K PRICE INCREASE

  • 5 Beds
  • 3.5 Baths
  • 2,709 Sq Ft

  399 Bentley Rd, Hartford, VT 05059

  The Evergreen at Mountain Stream — Currently under construction at 399 Bentley Road, the Evergreen offers 2,709 square feet of contemporary living across two finished levels, paired with a detached two-car garage. A long, low silhouette under a standing-seam metal roof, composite board-and-batten siding, and oversized windows give the home a distinctly modern presence — clean architectural lines

  Richard Higgerson Higgerson & Company

  399 Bentley Rd, Hartford, VT 05059
• 

  

  /6

  $175,000

  • Land
  • 1.02 Acres
  • $171,569 per Acre

  Lot 51 Partridge Rd, Ludlow, VT 05149

  1.02+/- acres. Lot 51. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

  Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

  Lot 51 Partridge Rd, Ludlow, VT 05149
• 

  /2

  $26,900

  $2K PRICE DROP

  • Land
  • 1.9 Acres
  • $14,158 per Acre

  223 Falcon Loop Rd E, Rochester, VT 05767

  Build your Vermont retreat on this 1.90-acre wooded lot in thedesirable Great Hawk community in Rochester. Surrounded by natural beauty, this property offers a peaceful setting with access to hiking, skiing, and year-round outdoor recreation, plus nearby attractions like the Green Mountain National Forest and scenic Route 100. Rochester is loved for its quiet charm, local farms, and

  Derek Greene Derek Greene

  223 Falcon Loop Rd E, Rochester, VT 05767
• 

  

  /26

  $299,900

  • 2 Beds
  • 1.5 Baths
  • 1,063 Sq Ft

  253 Old Quechee Rd Unit 6C, Hartford, VT 05001

  OPEN HOUSE SUNDAY JUNE 7 FROM 2-4 PM. When we say turn-key, it is TURN-KEY! Come hang your clothes in the walk-in closet and put your feet up to enjoy this fully furnished Mill Run II condo in the beautiful Quechee Lakes community. This low-maintenance condo has been exceptionally well renovated. Some of the upgrades include: upgraded kitchen with granite counters, stainless steel appliances,

  Franchesca Collins Hall Collins Real Estate Group

  253 Old Quechee Rd Unit 6C, Hartford, VT 05001
• 

  

  /13

  $50,000

  • Land
  • 1.5 Acres
  • $33,333 per Acre

  2-63 Goshawk Dr, Plymouth, VT 05056

  Affordable opportunity to build your dream home in a quiet neighborhood located between Okemo and Killington Mountain Resorts, with nearby access to Echo Lake, Hawk Resort hiking trails, and Plymouth State Park. With utilities close by and the ability to connect to the community wastewater system, this lot is ready for your new Vermont home. Community covenants and design standards help protect

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  2-63 Goshawk Dr, Plymouth, VT 05056
• 

  

  /14

  $239,000

  • 9 Beds
  • 2 Baths
  • 11,500 Sq Ft

  199 Summer St, Springfield, VT 05156

  A unique opportunity to acquire the former East School property at 199 Summer Street in Springfield, Vermont. Set on approximately 2.5 acres, the property includes a roughly 11,500 sq. ft. former school building with road access, municipal water and sewer, and Medium Density Residential zoning. Listed at $239,000, this property offers significant potential for multifamily housing, residential

  David White OwnerEntry.com

  199 Summer St, Springfield, VT 05156
• 

  

  /48

  $6,750,000

  New Construction $500K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,087 Sq Ft

  412 Skyland Ln, Woodstock, VT 05091

  Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

  Story Jenks LandVest, Inc/Woodstock

  412 Skyland Ln, Woodstock, VT 05091
• 

  /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
• 

  

  /15

  $96,232

  New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  108 Cubb Ct, Windsor, VT 05089

  Welcome to 132 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  108 Cubb Ct, Windsor, VT 05089
• 

  

  /37

  $865,000

  $320K PRICE DROP

  • 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
• 

  

  /60

  $1,350,000

  • 4 Beds
  • 3 Baths
  • 2,311 Sq Ft

  323 Turnpike Rd, Norwich, VT 05055

  Where to begin, this property has so many special facets: Antique Cape that has been sensitively updated consistent with the style of the house; a guest house (Cape) built in 2004; an amazing renovated barn ready to host gatherings of all sorts and plenty of storage under the main level;stonewalls, stone patio, raised stone patio, fenced garden space, large openlawn area at the back of

  Berna Rexford Four Seasons Sotheby's Int'l Realty

  323 Turnpike Rd, Norwich, VT 05055
• 

  

  /38

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  847 Simonsville Rd, Andover, VT 05143

  Looking to find your own peaceful piece of the Vermont countryside? Look no further than this move in ready homestead on 51.2 rolling acres with twopaddocks already fenced and ready waiting for your animals. Also complete with two spacious sheds for animals or storage, and a chicken coop ready to house them. Established asparagus patch, garden plot,blueberry bushes, apple trees, and even

  Erin Kendall EXP Realty

  847 Simonsville Rd, Andover, VT 05143
• 

  

  /53

  $525,000

  • 4 Beds
  • 2 Baths
  • 2,232 Sq Ft

  133 Baltimore Rd, North Springfield, VT 05150

  A true farm ready for its next chapter! These grounds have been lovingly tilled, gardened, sown, and harvested; the soil meticulously fed, and the pastures grazed by generations of animals. Hundreds of pounds of produce have been grown in and out of the greenhouse high tunnel. A massive, fixed-rack solar array covers the primary costs of electricity and feeds back into the grid. What is most

  Franchesca Collins Hall Collins Real Estate Group

  133 Baltimore Rd, North Springfield, VT 05150
• 

  

  /20

  $290,000

  $10K PRICE DROP

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

  1175 Quarry Rd, Chester, VT 05143

  Discover the true meaning of "getting away from it all" at 1175 Quarry Road. This expansive 75 acre parcel is tucked away a full mile up a quiet, dead end dirt road in the desirable town of Chester. Mostly wooded with rising topography.It’s an ideal canvas for a private homestead, a hunting camp, or a seasonal getaway. You get the peace of a dead end road with the convenience of being near

  Jessica Samples BHG Masiello Keene

  1175 Quarry Rd, Chester, VT 05143
• 

  

  /30

  $100,000

  $70K PRICE DROP

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

  25 Wilder Ln, Bethel, VT 05032

  Both toilets in the bathroom broke and flooded the home. It is now being sold as essentially land, and the mobile home will need to be removed.Water/septic/electric were all in working order Fall 2025.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,

  Jeremy Collins Ridgeline Real Estate

  25 Wilder Ln, Bethel, VT 05032
• 

  

  /22

  $199,000

  • 1 Bed
  • 448 Sq Ft

  1440 Stevens Rd, Bridgewater, VT 05034

  Serenity and nature await you on 2 beautiful acres and a well loved seasonal one bedroom camp with propane vented wall heater and gas cookstove. Located almost at the end of the Bridgewater town maintained road. Beyond the town maintained road is Killington and at that portion of the road it is not maintained by the municipality. Enjoy access to VAST and VASA trails. Awesome mountain biking,

  Meredith Rieger KW Vermont-Killington

  1440 Stevens Rd, Bridgewater, VT 05034
• 

  

  /47

  $395,000

  $44K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  5798 W Woodstock Rd, Woodstock, VT 05091

  Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors

  Carol Wood Williamson Group Sothebys Intl. Realty

  5798 W Woodstock Rd, Woodstock, VT 05091
• 

  

  /50

  $1,600,000

  Open Sat 1PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  328 Gravelin Rd, Perkinsville, VT 05151

  High Shelter Farm offers the ultimate Vermont lifestyle on 271 extraordinary acres of fields, forests, and breathtaking views. Once a working farm, this remarkable property features over six miles of professionally designed trails by John Morton of Morton Trails, providing year-round recreation for cross-country skiing, snowmobiling, ATV adventures, hiking, and exploration. Direct access to

  Gary Coger Four Seasons Sotheby's Int'l Realty

  328 Gravelin Rd, Perkinsville, VT 05151
• 

  

  /40

  $499,500

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  111 E Gilson Ave, White River Junction, VT 05001

  This is the type of property that doesn't come around very often! It is set on 2.5 private acres at the end of the road, abutting Vermont State Forest land. That said, it has terrific walkability to stores, Simon Pearce, the elementary school, Lake Pinneo, nearby hiking trails and Quechee Gorge. It's an easy drive to skiing, shopping in West Lebanon and hospitals. The land features level sunny

  Mary Paino Coldwell Banker LIFESTYLES - Quechee

  111 E Gilson Ave, White River Junction, VT 05001
• 

  

  /41

  $5,150,000

  • 8 Beds
  • 7.5 Baths
  • 10,062 Sq Ft

  3800 Weston-Andover Rd, Andover, VT 05143

  Escape to Moosewalk Lane. This ultimate family compound is a fully furnished and equipped rural retreat in Andover, Vermont. Set on 384 acres rising to 2,200 feet, the tract blends seclusion and timeless craftsmanship, with miles of private trails for winter sports, horseback riding and recreational vehicles, all threading through open meadows, historic stone walls, and woodlands, with direct

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  3800 Weston-Andover Rd, Andover, VT 05143
• 

  

  /8

  $275,000

  • Land
  • 1.95 Acres
  • $141,026 per Acre

  3186 South Rd, Woodstock, VT 05091

  1.95 Acre lot minutes from Woodstock Village, South Woodstock, and Green Mountain Horse Association. Kidder Brook runs along the North property boundary, and a sunny lawn area has multiple small gardens. There is a large clearing, and a well-cared for 1973 mobile home on a concrete slab on the property. This lot has tremendous potential in a fantastic location. House is being sold As-is.

  Andrew Hubbell Vermont Real Estate Company

  3186 South Rd, Woodstock, VT 05091
• 

  

  /21

  $199,000

  $100K PRICE DROP

  • Land
  • 8.1 Acres
  • $24,568 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
• 

  

  /27

  $525,000

  $14K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 2,304 Sq Ft

  81 High St, Cavendish, VT 05142

  This 1850s renovated property located right in the heart of the village adapts perfectly to your lifestyle or investment goals. This home functions seamlessly as a spacious 5-bedroom, 2-bathroom home or is ready to operate as two separate income-generating rental units. The unfinished third floor can easily be converted into additional living space, a master suite, or a bonus room. The spacious

  Tyleen Murray Kelley Real Estate, Inc.

  81 High St, Cavendish, VT 05142
• 

  

  /60

  $3,250,000

  • 5 Beds
  • 6.5 Baths
  • 5,728 Sq Ft

  191 Moon Shadow Dr Unit M19, Ludlow, VT 05149

  Solitude home at the top of the hill awaits! Solitude on Okemo Mountain, where this exceptional five-bedroom home captures the ultimate ski location, breathtaking long-range views, and unparalleled privacy. Perfectly positioned to embrace the beauty of the surrounding mountains, this residence offers a rare opportunity to enjoy true slope-side living in one of Vermont’s most sought-after resort

  Katherine Burns William Raveis Real Estate Vermont Properties

  191 Moon Shadow Dr Unit M19, Ludlow, VT 05149
• 

  

  /14

  $299,900

  • 5 Beds
  • 2 Baths
  • 1,772 Sq Ft

  3 Lark Ln, Springfield, VT 05156

  Welcome to 3 Lark Lane in Springfield, VT! This expanded 5-bedroom home offers flexible living space and many updates throughout. A spacious addition created a large bonus room along with an expansive kitchen and dining area perfect for everyday living and entertaining. The updated kitchen with granite countertops offers plenty of cabinet and counter space with an open flow into the dining area.

  Bobbie Lynn Thomas The Thomas Group of Northern New England, LLC

  3 Lark Ln, Springfield, VT 05156
• 

  /2

  $269,000

  • Land
  • 13.9 Acres
  • $19,353 per Acre

  1 Barbara Lee Ln, Norwich, VT 05055

  Tucked off a quiet country lane in desirable Norwich, this 13.9 acre parcel offers a beautiful blend of privacy, convenience, and thoughtfully advanced planning. Just 10 minutes to center village and Dan & Whit’s, the land features a mostly level, roughed-in driveway approach and a peaceful setting ideal for a serene Vermont lifestyle. EC Fiber is available at the road for modern connectivity. A

  Kris Lippi Get Listed Realty

  1 Barbara Lee Ln, Norwich, VT 05055
• 

  

  /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 (Buyer would need to obtain a driveway permit prior

  Tami Sullivan Snyder Donegan Real Estate Group

  00 Chapel Hill Rd, Sharon, VT 05065

Showing Results 401 - 440, Page 11 of 12