Windsor County VT Homes for Sale

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  /55

  $1,595,000

  • 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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  /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
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  /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
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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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  /14

  $54,900

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  159 Ash Ln, Springfield, VT 05156

  Are you looking for a reasonable place to live? This 14 x 70 1983 3BR/1BA home could be just it. Located outside the village limits in a nice country setting is available. Seller has upgraded the power to a 200 Amp panel, installed central air conditioning, and freshly painted the interior.Park approval is required prior to closing.

  

  Julie Buffum

  Buffum Realty

  159 Ash Ln, 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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  /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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  /52

  $1,249,000

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

  52 Fishing Access Rd, Ludlow, VT 05149

  Lakefront Living on Lake Rescue- Minutes from Okemo Mountain.Rarely does a Lake Rescue property offer this combination of location, views, privacy and four-season appeal. Perched above the clear waters of Lake Rescue, this distinctive lake house offers sweeping water views, easy access to boating and swimming, and the convenience of being just minutes from Okemo Mountain. Whether your ideal

  

  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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  /29

  $449,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  167 Chestnut St, Hartford, VT 05001

  Freshly painted inside and out, this beautifully renovated New Englander in Wilder Village blends timeless charm with modern updates, including a new roof, boiler, updated electric service, many new appliances, hardwood floors, and an upstairs washer and dryer. Situated on a rare, level 0.73-acre double lot with three garage bays, the property is just a short walk to the Connecticut River and

  

  Jeff Fogg

  Black House Real Estate

  167 Chestnut St, Hartford, VT 05001
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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

  Coming Soon

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

  151 Dwight Rd, Hartford, VT 05001

  Immaculately maintained 2 BR plus loft, 2BA home located on a private, quiet dead end road. Some of the many recent upgrades include: all new flooring through out including engineered hard wood floors on the main and upper level and new tile on the basement level, new paint through out the entire house including removal of popcorn ceilings and much, much more (a list of improvements is available

  

  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

  $1,695,000

  • 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#5072395Well-maintained 2-bedroom, 1.5-bath single-family home offering 1,278 sq. ft. of living space. Featuring a wrap-around enclosed porch and a full basement, ideal for storage. Set on a .65± acre property with excellent Route 4 frontage and visibility, just seconds to Interstate 89.The sale also includes a 3,020 sq. ft. commercial building and a second

  

  Cheryl Herrmann

  RE/MAX Group One Realtors

  3803 Woodstock Rd, Hartford, VT 05001
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  /59

  $1,550,000

  $140K PRICE DROP

  • 7,566 Sq Ft

  156 Main St, Ludlow, VT 05149

  In the heart of the ever-popular Ludlow, Vermont, sits an 11,409 square foot commercial building with 7,566 square feet of finished space. Built in 1990, it is situated in a prime location on Main Street in the center of the village providing it with excellent visibility, walkability, and proximity to Ludlow’s charming boutiques and local dining. It is full of investment possibilities with seven

  

  John Napier

  TPW Real Estate

  156 Main St, Ludlow, VT 05149
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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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  /6

  $300,000

  • Land
  • 10.2 Acres
  • $29,412 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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  /16

  $79,900

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 938 Sq Ft

  18 Water Ave, Weathersfield, VT 05030

  Meticulously maintained and move-in ready! This well cared for 2001 manufactured home offers 2 bedrooms and 2 full baths in a desirable 55+ community with a quiet dead-end location. The spacious kitchen features an abundance of cabinetry, providing plenty of storage and workspace, while the comfortable floor plan makes excellent use of the home's space.A convenient carport provides

  

  Justin Ranney

  Coldwell Banker Homes Unlimited

  18 Water Ave, Weathersfield, VT 05030
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  /45

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,180 Sq Ft

  259 Beaver Meadow Rd, Norwich, VT 05055

  A wonderful opportunity to own a solid, thoughtfully designed Colonial, built by a respected local Norwich builder and offered for the first time on the market. This inviting 4-bedroom, 2.5 bath home features an open living concept with a beautiful kitchen complete with granite countertops and a generous center island. Perfect for everyday living and entertaining. The first floor also offers a

  

  Cheryl Herrmann

  RE/MAX Group One Realtors

  259 Beaver Meadow Rd, Norwich, VT 05055
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  /58

  $1,350,000

  $50K 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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  /29

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,203 Sq Ft

  42 Mark St, Springfield, VT 05156

  Delightful cape style home in a family friendly neighborhood. Large lot with detached single car garage, additional building for storage, lots of level space for a garden or to fence in. Home features a covered entry. This home has seen lots of updates thru its life including a newer roof, new wooden siding that has been freshly painted, interior of the home has also been freshly painted. Lots of

  

  Julie Buffum

  Buffum Realty

  42 Mark St, Springfield, VT 05156
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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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  /57

  $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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  /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
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  /50

  $1,399,000

  $49K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  145 the Plateau, Windsor, VT 05089

  "The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two

  Dan Noble Snyder Donegan Real Estate Group

  145 the Plateau, Windsor, VT 05089
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  /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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  /58

  $450,000

  $25K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,865 Sq Ft

  81 Main St, Chester, VT 05143

  Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

  Betsy Adamovich Real Broker LLC

  81 Main St, Chester, VT 05143
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  /28

  $995,000

  • 3 Beds
  • 3.5 Baths
  • 2,584 Sq Ft

  26 Mount Peg Rd Unit C, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit C, Woodstock, VT 05091
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  /33

  $1,895,000

  • 2 Beds
  • 2.5 Baths
  • 2,944 Sq Ft

  2394 Fletcher Hill Rd, Woodstock, VT 05091

  Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

  John Snyder Snyder Donegan Real Estate Group

  2394 Fletcher Hill Rd, Woodstock, VT 05091
• 

  

  /31

  $1,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,385 Sq Ft

  26 Mount Peg Rd Unit D, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit D, Woodstock, VT 05091
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  /60

  $2,200,000

  $295K PRICE DROP

  • 5 Beds
  • 9 Baths
  • 7,322 Sq Ft

  1497 Bowman Rd, Barnard, VT 05068

  Circa 1799 Vermont cape, thoughtfully restored and expanded to over 7,300 finished square feet on 12.5 private acres, minutes to Silver Lake and Woodstock village. Five bedrooms, nine baths, and a layout that balances everyday living with the ability to host. Original materials carry throughout, including wide pine floors, skim-coat plaster walls, hand-carved paneling, and period hardware, giving

  Richard Higgerson Higgerson & Company

  1497 Bowman Rd, Barnard, VT 05068
• 

  

  /57

  $1,450,000

  • 3 Beds
  • 3 Baths
  • 1,836 Sq Ft

  144 Lodge Rd Unit 1, Ludlow, VT 05149

  Welcome to South Face Village! True slopeside living at its best. This front-row, ski-in/ski-out 3-bedroom, 3-bath condo is literally on the slope. Walk out your front door, plop your skis or board down and head to the Sunshine lift. This gives you direct access to the South Face Express Quad. Inside this immaculate, turnkey unit is everything you'll want in your mountain château. Step in take

  Frank Provance Diamond Realty

  144 Lodge Rd Unit 1, Ludlow, VT 05149
• 

  

  /58

  $2,650,000

  $450K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,843 Sq Ft

  66 Hollow Farm Rd, Woodstock, VT 05071

  CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows

  David Donegan Snyder Donegan Real Estate Group

  66 Hollow Farm Rd, Woodstock, VT 05071
• 

  

  /44

  $824,900

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,392 Sq Ft

  117 Horseshoe Dr, Brownsville, VT 05037

  Experience the best of Vermont living in this custom-built home in desirable West Windsor, where thoughtful craftsmanship, energy efficiency, and four-season recreation come together. Designed and built by its original builder, this home offers exceptional quality, low-maintenance living, and comfortable year-round enjoyment. Whether you're searching for a primary residence, a Vermont vacation

  Katie Ladue Gilbert BHHS Verani Upper Valley

  117 Horseshoe Dr, Brownsville, VT 05037

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