Windsor County VT Homes for Sale

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  /55

  $1,495,000

  $100K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 3,521 Sq Ft

  2615 North Rd, Barnard, VT 05031

  At 2615 North Road, the landscape is ever-present. Expansive decks and walls of windows invite the mountains into everyday life, from the first light across the hills to the rich colors of a Vermont sunset. Set along one of Barnard’s most coveted roads, this fully renovated five-bedroom, 5.5-bath home brings a sophisticated point of view to country living...beautifully considered, effortlessly

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  2615 North Rd, Barnard, VT 05031
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  /47

  $1,595,000

  $300K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,708 Sq Ft

  196 Cowdrey Outlook, Bethel, VT 05032

  For the first time in over half a century, this extraordinary 100+ acre estate-level property in Barnard is being offered for sale. Cherished by the same family for generations, the property presents a rare opportunity to own one of Vermont’s most scenic and versatile landscapes. Commanding long-range mountain views define the setting, while several picturesque spring-fed ponds, rolling meadows,

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  196 Cowdrey Outlook, Bethel, VT 05032
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  /20

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  1268 County Rd, Windsor, VT 05089

  Pull off County Road and the gravel goes quiet under the tires as 16.35 acres in Windsor, Vermont open in grass, timber, and sky. Hubbard Brook moves through the land with water over stone, cool in the shade and bright where the light finds it, and a snowmobile trail crosses the acreage when winter takes the fields. I-91 sits close enough that the Upper Valley is an easy reach. That is 1268

  

  Vin Morris

  BHHS Verani Upper Valley

  1268 County Rd, Windsor, VT 05089
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  /41

  $675,000

  • 4 Beds
  • 3.5 Baths
  • 2,625 Sq Ft

  443 Alden Partridge Rd Unit 3D, Hartford, VT 05001

  Welcome to this beautifully situated 4BR, 3.5BA end unit townhouse located within the highly desirable Ridge Condo Association. Offering exceptional privacy, abundant light and fantastic mountain views, this spacious property is the perfect combination of comfort, convenience and location. The open and inviting floor plan provides plenty of room for family and guests. Being sold fully furnished,

  

  Herb Hart

  Quechee Lakes Real Estate Center

  443 Alden Partridge Rd Unit 3D, Hartford, VT 05001
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  /38

  $549,000

  Open Fri 5PM - 7PM

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

  220 Missing Link Rd, Springfield, VT 05156

  Imagine waking up to the sun rising over the mist of the Connecticut River, then stepping outside your door with your morning coffee to relax on one of two expansive decks... or maybe heading down to your private beach and boat dock for a morning river cruise. This beautifully-maintained, elegant 3-BR / 3 BA waterfront colonial offers an unparalleled riverfront lifestyle, perched majestically

  

  Jeffrey Brown

  American Dream Real Estate Associates, L

  220 Missing Link Rd, Springfield, VT 05156
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  /53

  $425,000

  • 3 Beds
  • 2 Baths
  • 3,286 Sq Ft

  20 Barlow Rd, Springfield, VT 05156

  Welcome to your own personal oasis. This beautiful log home is located on a quiet country road just minutes from downtown Springfield. The home features a detached 2 car garage, covered front porch entry, (just room enough for a pair of rocking chairs), a large open deck, above ground pool, gazebo, seasonal outside toilet, a sweet little lily pond water feature, outside storage open laws and

  

  Julie Buffum

  Buffum Realty

  20 Barlow Rd, Springfield, VT 05156
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  /43

  $699,000

  • 2 Beds
  • 3 Baths
  • 1,364 Sq Ft

  193 Jackson Gore Unit 739/741, Ludlow, VT 05149

  Come and experience Vermont at its best! This condo is located in Jackson Gore on Okemo Mountain in Ludlow. This slope side condo unit has stunning views of the mountain and trails. This unit would serve well as a family retreat or rental investment property. It boasts a gas fireplace for cold winter nights. It has 2 bedrooms and 3 bathrooms and offers lock-out capability for separate rental

  

  John Napier

  TPW Real Estate

  193 Jackson Gore Unit 739/741, Ludlow, VT 05149
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  /42

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,466 Sq Ft

  64 Bullock Rd, Norwich, VT 05055

  Discover contemporary living in this beautifully designed 1,400-square-foot, 2-bedroom, 2-bath home, built in 2016 and set on 10.5 private acres just 3 miles from downtown Hanover and 7 miles from Dartmouth Hitchcock Medical Center.The thoughtfully designed open floor plan features polished concrete floors, expansive windows, and abundant natural light, creating a bright, inviting atmosphere

  

  Cheryl Herrmann

  RE/MAX Group One Realtors

  64 Bullock Rd, Norwich, VT 05055
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  /39

  $949,000

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,183 Sq Ft

  63 Royall Tyler Rd, Hartford, VT 05001

  Settle into the farmers porch with a morning coffee and watch the seasons change across the Vermont hills. Inside, every detail speaks to quality craftsmanship — thoughtful appointments, warm finishes, and a layout designed for real family life. The yard has plenty of room for kids to run, explore, and make the kind of memories that bring families back to Vermont generation after

  

  Herb Hart

  Quechee Lakes Real Estate Center

  63 Royall Tyler Rd, Hartford, VT 05001
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  /60

  $1,725,000

  • 3 Beds
  • 3 Baths
  • 3,150 Sq Ft

  1089 Union Village Rd, Norwich, VT 05055

  Custom designed by owner/artist and renowned Vermont architect, Richard “Dick” Robson, this extraordinary residence is a true one-of-a-kind home, filled with thoughtful design, artistic details, and natural elements drawn directly from the property itself.A dramatic two-story stone chimney anchors the entry foyer and incorporates built-in waterfalls, while a dedicated meditation room offers

  

  Cheryl Herrmann

  RE/MAX Group One Realtors

  1089 Union Village Rd, Norwich, VT 05055
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  /51

  $1,249,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  52 Fishing Access Rd, Ludlow, VT 05149

  Lakefront Living Meets Mountain Adventure on Lake RescueLocated just minutes from Okemo Mountain, this home offers a rare opportunity to own a property that masterfully bridges the best of Vermont’s lake and ski seasons. Whether you are seeking a premier lakefront retreat or a cozy mountain lodge, this home is designed to deliver the perfect four-season lifestyle.The interior is built for

  

  Gail Beardmore

  Engel & Völkers Okemo

  52 Fishing Access Rd, Ludlow, VT 05149
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  /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

  00 Will Dean Rd, Springfield, VT 05156
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  /55

  $975,000

  • 4 Beds
  • 3.5 Baths
  • 4,474 Sq Ft

  56 Sundback Ln, Norwich, VT 05055

  Set against a beautiful backdrop of wooded Vermont hills, this Norwich home offers exceptional privacy, generous outdoor space, and easy access to the Upper Valley. Set on 5.56 acres, the four-bedroom home is surrounded by an expansive lawn and mature forest, creating a peaceful setting with room to garden, gather, play, and experience Vermont’s changing seasons.Inside, hardwood floors

  

  Lori Shipulski

  BHHS Verani Upper Valley

  56 Sundback Ln, Norwich, VT 05055
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  /6

  $299,000

  • Land
  • 116.2 Acres
  • $2,573 per Acre

  00 Grout Rd, Weathersfield, VT 05153

  A large private parcel of land located in Cavendish on the Weathersfield line. This 116+- acres is a mix of woods and cleared areas that has beautiful mountain views that can be accessed from Grout road. There is road frontage on scenic vermont route 131 that can access the land with grading. These 2 lot have been surveyed and there are multiple possible building sites. This property is close to

  

  John Napier

  TPW Real Estate

  00 Grout Rd, Weathersfield, VT 05153
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  /30

  $479,000

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  151 Dwight Rd, Hartford, VT 05001

  Immaculately maintained and truly move-in ready, this beautifully updated 2-bedroom plus loft, 2-bath home offers the perfect blend of comfort, privacy, and four-season Vermont living. Tucked away on a quiet, private dead-end road, the home is surrounded by a peaceful, setting while remaining exceptionally convenient to everything the Upper Valley has to offer.The home has been

  

  Herb Hart

  Quechee Lakes Real Estate Center

  151 Dwight Rd, Hartford, VT 05001
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  /30

  $75,000

  • 1,440 Sq Ft

  178 Church St, Bethel, VT 05032

  Looking for a Summer Project? Put your ambition and skills to work in this unfinished, single-story 30' x 24'+ wood framed shell constructed with beefy rough-cut lumber. Electric service provided by Green Mountain Power (meter on building). Public water service to, and public sewage disposal from, are available on site. Currently, there is no electrical wiring, plumbing pipes, nor fixtures, but

  

  Lori Holt

  BHHS Vermont Realty Group/Montpelier

  178 Church St, Bethel, VT 05032
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  /60

  $1,645,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,800 Sq Ft

  2706 E Woodstock Rd, Woodstock, VT 05091

  Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former

  

  John Bassette

  Bassette Real Estate Group

  2706 E Woodstock Rd, Woodstock, VT 05091
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  /27

  $539,000

  $360K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,278 Sq Ft

  3803 Woodstock Rd, Hartford, VT 05001

  **Sale Price includes MLS#5072395Unlock unmatched flexibility and long-term value with this unique multi-property offering, perfectly positioned with excellent Route 4 frontage and high visibility just seconds from Interstate 89. Being sold together, this package includes both a turnkey residential home and a spacious commercial building (MLS#5072395), making it an ideal setup for

  

  Cheryl Herrmann

  RE/MAX Group One Realtors

  3803 Woodstock Rd, Hartford, VT 05001
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  /49

  $2,195,000

  • 3 Beds
  • 3 Baths
  • 2,997 Sq Ft

  9671 Vt Route 12, Barnard, VT 05031

  SPRING HILL FARM– A Storied Vermont Estate with Timeless Appeal. Set amidst the rolling hills of Barnard, Vermont, Spring Hill Farm is a distinguished country estate where historic charm and thoughtful stewardship come together across 207 acres of beautifully maintained landscape. Anchoring the property is a stately brick residence dating to 1795, offering a refined sense of heritage and

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  9671 Vt Route 12, Barnard, VT 05031
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  /30

  $279,000

  • 3 Beds
  • 1 Bath
  • 1,331 Sq Ft

  139 Pleasant Valley Rd, Springfield, VT 05156

  Original 1800's cape style home situated conveniently between Springfield and Chester. Home has seen updates over the years but continues to show original charm of an 1800's period home, exposed beams in primary bedroom, mixed wood floors, post and beam shed/garage with usable and accessible second floor. The enclosed front porch leads you to the comfortable, sunlit eat in country kitchen which

  

  Julie Buffum

  Buffum Realty

  139 Pleasant Valley Rd, Springfield, VT 05156
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  /54

  $2,599,000

  • 9 Beds
  • 11 Baths
  • 5,993 Sq Ft

  41 Pleasant St, Woodstock, VT 05091

  This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

  

  Jennifer Falvey

  KW Vermont Woodstock

  41 Pleasant St, Woodstock, VT 05091
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  /52

  $499,000

  $200K PRICE DROP

  • 2.5 Baths
  • 7,445 Sq Ft

  66 Duttonsville School Dr, Cavendish, VT 05142

  Where History Meets Possibility. An 1862 Schoolhouse Reimagined.Step back in time and into opportunity. Built in 1862, this remarkable historic schoolhouse has been lovingly preserved, its character and craftsmanship thoughtfully maintained while seamlessly supporting modern use.Since 1973, the building has served as the home of a thriving distribution business, proof of its adaptability,

  

  Gail Beardmore

  Engel & Völkers Okemo

  66 Duttonsville School Dr, Cavendish, VT 05142
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  /49

  $2,499,000

  • 5 Beds
  • 5.5 Baths
  • 4,462 Sq Ft

  3398 Jericho Rd, White River Junction, VT 05001

  Built in 1789, the year George Washington was elected President, the Philemon Hazen Homestead is a rare Vermont property where history, architecture and modern luxury come together. Set among rolling pastures in Hartford’s Jericho Rural Historic District, this 4,462 sq. ft. historic farmhouse feels a world away—yet is just 6 miles from Hanover and Dartmouth College, 5 miles from Norwich and less

  

  Jennifer Falvey

  KW Vermont Woodstock

  3398 Jericho Rd, White River Junction, VT 05001
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  /6

  $269,900

  $30K PRICE DROP

  • Land
  • 10.2 Acres
  • $26,461 per Acre

  0 Union Village Rd Unit 5106130, Norwich, VT 05055

  Discover the perfect canvas for your Vermont dream property! This expansive 10.22-acre parcel sits prominently in the highly desirable Rural Residential (RR) district of Norwich. Boasting over 1,000 feet of expansive road frontage along Union Village Road, this land offers incredible privacy and presence while keeping you just 2 miles from the heart of town and the iconic Dan & Whit’s general

  

  Cheryl Herrmann

  RE/MAX Group One Realtors

  0 Union Village Rd Unit 5106130, Norwich, VT 05055
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  /12

  $99,999

  $20K PRICE DROP

  • Land
  • 3.24 Acres
  • $30,864 per Acre

  508 Mattson Rd, Chester, VT 05143

  This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn, ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded

  

  Jessica Citera

  Cummings & Co

  508 Mattson Rd, Chester, VT 05143
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  /51

  $950,000

  • 3 Beds
  • 1.5 Baths
  • 2,020 Sq Ft

  888 Skyline Dr, Springfield, VT 05156

  Being offered for sale for the second time since our country was founded, this 1750's cape is sitting on 50 0f the 110 acres of the original land grant. Current family has owned the property since 1936, lovingly caring for and maintaining the home and land. The land is both open and wooded with the wooded in land use. Snow mobile trails cross a portion of the property for easy access for winter

  

  Julie Buffum

  Buffum Realty

  888 Skyline Dr, Springfield, VT 05156
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  /58

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 4,280 Sq Ft

  844 Greeley Rd, Springfield, VT 05156

  Pastoral views abound with this newer built home in a farming neighborhood. This beautiful, energy efficient home was built for family, friends and entertainment. From the moment you enter the large foyer you aren't sure where to look first; straight ahead and out the French doors to the deck and onto the fields and mountains beyond, to the dream kitchen with stunning cabinetry and granite

  

  Julie Buffum

  Buffum Realty

  844 Greeley Rd, Springfield, VT 05156
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  /58

  $1,275,000

  $125K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 4,571 Sq Ft

  505 Deweys Mills Rd, Hartford, VT 05047

  The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the

  

  Jennifer Falvey

  KW Vermont Woodstock

  505 Deweys Mills Rd, Hartford, VT 05047
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  /25

  $349,000

  $20K PRICE INCREASE

  • 2 Beds
  • 1.5 Baths
  • 1,380 Sq Ft

  355 Lyman Batcheller Rd Unit 9A, Hartford, VT 05001

  Cozy 2BR, 1.5Ba end unit condo with an open floor plan being sold mostly furnished with only a few exceptions. Located in the Saltbox Village Condo association which offers a private, quiet and well maintained country setting. Within walking distance to the Library, Post Office, Simon Pearce and the Village Green. The kitchen has been updated and a mini split has been added to keep the condo cool

  

  Herb Hart

  Quechee Lakes Real Estate Center

  355 Lyman Batcheller Rd Unit 9A, Hartford, VT 05001
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  /43

  $509,000

  • 4 Beds
  • 3 Baths
  • 2,526 Sq Ft

  231 Rte 100, Weston, VT 05161

  Quintessential 1880s Vermont farmhouse in bucolic Weston. Nestled on 7 private acres, this 4 bedroom, 3 bath retreat offers authentic pine floors, historical charm throughout with a tranquil pond greeting you upon arrival. It is the perfect blend or timeless character and rural serenity. BRAND NEW DRILLED WELL & MOUND SEPTIC SYSTEM just installed in August 2026. Updated electric makes this house

  

  Margretta Fischer

  Wohler Realty Group

  231 Rte 100, Weston, VT 05161
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  /43

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,489 Sq Ft

  32 Mark St, Springfield, VT 05156

  More photos are coming! This home has been loved and cared for 50 plus years by the same family and now it is ready for a new chapter. Located in a nice family friendly neighborhood that is perfect for evening strolls around the block. Home features newer windows, hardwood floors, a heated sunroom, and a large dining room. The living room flows nicely into the heated sunroom for lots of

  

  Julie Buffum

  Buffum Realty

  32 Mark St, Springfield, VT 05156
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  /17

  $75,000

  • 2 Beds
  • 1 Bath
  • 620 Sq Ft

  1144 Potash Brook Rd, Chester, VT 05143

  Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

  

  Julie Buffum

  Buffum Realty

  1144 Potash Brook Rd, Chester, VT 05143
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  /12

  $149,000

  • Land
  • 17.7 Acres
  • $8,418 per Acre

  0 Trebo Rd, Chester, VT 05143

  Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont

  

  Gail Beardmore

  Engel & Völkers Okemo

  0 Trebo Rd, Chester, VT 05143
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  /56

  $850,000

  • 4 Beds
  • 2 Baths
  • 2,352 Sq Ft

  208 Jarvis Rd, Perkinsville, VT 05151

  Motivated Seller! This exceptional four-bedroom home encompasses 11.5 pristine acres. The residence features light-filled, elegantly scaled principal rooms optimized for entertaining and daily living. There is a study/bedroom on the first floor with a three-quarter hall bath next to it. Upstairs, there are three bedrooms (one is being used as a study) and a generously scaled but cozy reading

  

  Jennifer Falvey

  KW Vermont Woodstock

  208 Jarvis Rd, Perkinsville, VT 05151
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  /33

  $537,000

  Open Sat 11AM - 1PM Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,104 Sq Ft

  1778 Goulden Ridge Rd, Springfield, VT 05156

  Tucked away in a peaceful, private setting with an incredible mountain view, this 3-bedroom, 1¾-bath home offers the kind of seclusion that's hard to find without giving up convenience. Easy access to I-91 puts Lebanon, Dartmouth, shopping, dining, and the Upper Valley within reach, while Killington, Okemo, and Stratton are all options for a day on the slopes. Crown Point Country Club, Wellwood

  

  Kirsten Dole

  Coldwell Banker LIFESTYLES - Hanover

  1778 Goulden Ridge Rd, Springfield, VT 05156
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  /60

  $475,000

  $20K PRICE DROP

  • 3,036 Sq Ft

  7868 Pomfret Rd, North Pomfret, VT 05053

  CASH FLOW POSITIVE - GREAT VALUE! 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 space,

  

  John Bassette

  Bassette Real Estate Group

  7868 Pomfret Rd, North Pomfret, VT 05053
• 

  /2

  $129,000

  $10K PRICE DROP

  • 2,144 Sq Ft

  73 Union St, Springfield, VT 05156

  Nice sized in-town home and yard with large 2 car garage and shed. Lots of room for your toys. The home is currently a 2-unit home but was originally a single-family home and could be changed back into a one family without a lot of effort. Home does need some work so cash buyers only please. This could be your chance to get into rental business. Lots of possibilities for this home.Home is

  

  Julie Buffum

  Buffum Realty

  73 Union St, Springfield, VT 05156
• 

  

  /47

  $670,000

  $29K PRICE DROP

  • 7 Beds
  • 5.5 Baths
  • 4,642 Sq Ft

  41 Lawrence Hill Rd, Weston, VT 05161

  Perfectly situated in the heart of one of Southern Vermont's most picturesque villages. Just a short drive from Stratton Mountain, Okemo Mountain Resort, Bromley Mountain, and Magic Mountain, this beautifully preserved property offers the ideal combination of historic character and modern comfort.Thoughtfully maintained, the home showcases classic New England architecture with warm pine

  

  Jessica Citera

  Cummings & Co

  41 Lawrence Hill Rd, Weston, VT 05161
• 

  

  /37

  $399,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,148 Sq Ft

  40 Fenton Rd, Chester, VT 05143

  This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

  

  John Napier

  TPW Real Estate

  40 Fenton Rd, Chester, VT 05143
• 

  

  /59

  $3,500,000

  • 5 Beds
  • 4.5 Baths
  • 6,170 Sq Ft

  56 Cream Pot Rd, Hartland, VT 05048

  CREAMPOT FARM- Idyllic country estate with easy access to Woodstock Village. Set on 104+ acres, this pristine property offers private groomed trails, beautifully landscaped grounds, multiple ponds, and stunning southerly views toward Mount Ascutney. From the moment you enter the gated drive and wind through stone walls, there is an immediate sense of peace and privacy. Originally built by G.R.

  David Donegan Snyder Donegan Real Estate Group

  56 Cream Pot Rd, Hartland, VT 05048

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