Windsor County VT Homes for Sale

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  /38

  $599,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 3,428 Sq Ft

  583 Hawk Spur Rd, Plymouth, VT 05056

  Looking for a property with HUGE equity possibilities?? Your dream mountain retreat perfectly nestled between Okemo/Vail and Killington awaits! This contemporary diamond in the rough boasts mountain views and sits on a double lot in the desirable Hawk resort area. You will fall in love with the floods of natural light that bring the outdoors in. This home is ready for your ideas and finishes

  

  Lisa Kelley

  Cummings & Co

  (802) 988-7969

  583 Hawk Spur Rd, Plymouth, VT 05056
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  /56

  $795,000

  • 3 Beds
  • 2 Baths
  • 1,940 Sq Ft

  211 Wood Rd, Hartford, VT 05001

  100 ACRE WOODS!! - Complete turn-key package for vacation rentals and a second home. Tucked away on 96+ protected acres spanning Hartford/Quechee, and a portion of Hartland, this fully furnished 3-bedroom, 2-bath log home offers exceptional privacy, quiet, & year-round recreation....Includes a robust (optional) rental program close to Woodstock. There is an existing subdivision in place if you

  

  John Bassette

  Bassette Real Estate Group

  (802) 613-0560

  211 Wood Rd, Hartford, VT 05001
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  /33

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,446 Sq Ft

  158 MacIntosh Hill Rd, Randolph, VT 05060

  Charming 1820's antique farmhouse with handcrafted cabinets and wide board floors. The home has updated systems including Viessmann on demand water heater, holding tank, pressure tank, newer electrical. Fabulous upgraded bathroom. There is a space of many uses that could be a studio, master suite, in law/guest suite. Also the most lovely screened in back sitting porch overlooking the pastures.

  

  Sherri McPhetres

  Vermont Heritage Real Estate

  (802) 499-2434

  158 MacIntosh Hill Rd, Randolph, VT 05060
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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

  (802) 327-7566

  00 Will Dean Rd, Springfield, VT 05156
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  /17

  $224,900

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  135 Wall St, Springfield, VT 05156

  Large, in town family home. Lots of room to spread out, 1st floor laundry, formal dining room, first floor bedroom, open second floor landing makes for a great space for a workspace, tv space or reading nook. All rooms are generous in size; large covered front porch makes for great place to hang out in rain or shine. Covered side entry into the home for convenience right off the driveway. This is

  

  Julie Buffum

  Buffum Realty

  (802) 613-9305

  135 Wall St, Springfield, VT 05156
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  /21

  $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

  (802) 330-8205

  178 Church St, Bethel, VT 05032
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  /57

  $535,000

  • 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

  (802) 802-3094

  298 Jenneville Rd, Windsor, VT 05089
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  /49

  $2,195,000

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

  9671 Vt Route 12, Barnard, VT 05031

  [See the property specific website with video, hi-rez photos and more]. 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

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  (802) 300-4226

  9671 Vt Route 12, Barnard, VT 05031
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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

  (802) 347-9544

  41 Pleasant St, Woodstock, VT 05091
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  /33

  $195,000

  • Land
  • 3.41 Acres
  • $57,185 per Acre

  119 Advent Hill Rd, Hartland, VT 05048

  Perched high in the scenic hills of Hartland, this exceptional 3.41 acre parcel offers the perfect balance of privacy, sunshine, and sweeping Vermont beauty. Fully surveyed, the property features a selectively cleared and thoughtfully laid out open house site, positioned to capture big vistas overlooking abutting fields and pastureland. In a neighborhood with multi-million dollar homes nearby,

  

  John Bassette

  Bassette Real Estate Group

  (802) 523-2987

  119 Advent Hill Rd, Hartland, VT 05048
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  /60

  $950,000

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

  34 Midsomer Meadows Ln, Woodstock, VT 05091

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

  

  John Bassette

  Bassette Real Estate Group

  (802) 347-6383

  34 Midsomer Meadows Ln, Woodstock, VT 05091
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  /2

  $349,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft

  31 Northfield Dr, North Springfield, VT 05150

  First time on market! This custom-built home has had only one owner. Shows like a new home. The owners have meticulously maintained this home and are ready to pass it on for its next chapter. Situated in a neighborhood in North Springfield just off the beaten path you'll enjoy the neighborhood, great area for walking and nature is literally out your back door. This home features an efficient

  

  Julie Buffum

  Buffum Realty

  (802) 200-2986

  31 Northfield Dr, North Springfield, VT 05150
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  /34

  $320,000

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  860 Murphy's Rd Unit 4A, Quechee, VT 05059

  Move in ready 2BR, 1.5BA end unit condo with a fabulous view being sold fully furnished. This condo has been tastefully updated throughout and includes two mini splits in the living room and primary bedroom. Located within walking distance to both Lake Pinneo and the Quechee Clubhouse.

  

  Herb Hart

  Quechee Lakes Real Estate Center

  (802) 204-5972

  860 Murphy's Rd Unit 4A, Quechee, VT 05059
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  /58

  $1,400,000

  • 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

  (877) 419-4767

  505 Deweys Mills Rd, Hartford, VT 05047
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  /4

  $160,000

  • Land
  • 6 Acres
  • $26,667 per Acre

  1901 Royalton Hill Rd, South Royalton, VT 05068

  Great opportunity to turn this private lot into your dream Vermont retreat. Just 10 minutes from the highway. Current owner has started some clearing and land prep.

  

  Steve Swanson

  EXP Realty

  (802) 215-3062

  1901 Royalton Hill Rd, South Royalton, VT 05068
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  /43

  $425,000

  • 5 Beds
  • 2 Baths
  • 1,982 Sq Ft

  176 Meadow Rd, Chester, VT 05143

  The Best of Both Worlds: Modern Comfort Meets Village Charm!Discover the perfect blend of contemporary upgrades and serene neighborhood. This meticulously updated raised ranch offers an expansive layout designed for both effortless entertaining and comfortable daily living.Step inside to find a light-filled open-concept living and dining area, anchored by stunning hickory hardwood floors

  

  Lauren Behm

  Berkshire Hathaway HomeServices Stratton Home

  (802) 416-3199

  176 Meadow Rd, Chester, VT 05143
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  /29

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  447 Elm St, Chester, VT 05143

  Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by

  

  Lisa Kelley

  Cummings & Co

  (802) 200-2452

  447 Elm St, Chester, VT 05143
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  /60

  $475,000

  • 4 Beds
  • 5 Baths
  • 3,036 Sq Ft

  7868 Pomfret Rd, North Pomfret, VT 05053

  CASH FLOW POSITIVE - PRICE REDUCTION! 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

  

  John Bassette

  Bassette Real Estate Group

  (802) 215-9321

  7868 Pomfret Rd, North Pomfret, VT 05053
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  /2

  $169,000

  • 1,662 Sq Ft

  32 Reed St, Springfield, VT 05156

  Nice, neat 2-unit property with good rental history. Each unit has 2 bedrooms, 1 bath. Separate parking for both units and back yard for outdoor enjoyment. Property has been well maintained and could be converted into a one family if desired. Great income opportunity or great starter home if you are looking to get part of your mortgage paid by rental income.

  

  Julie Buffum

  Buffum Realty

  (802) 471-3386

  32 Reed St, Springfield, VT 05156
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  /5

  $139,000

  • 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

  (802) 423-2965

  73 Union St, Springfield, VT 05156
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  /47

  $1,895,000

  • 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

  (802) 284-4197

  196 Cowdrey Outlook, Bethel, VT 05032
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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
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  /60

  $899,000

  • 6 Beds
  • 6 Baths
  • 5,497 Sq Ft

  31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767

  Charming 1900s Village Building, Three Condo Units, One Incredible Opportunity! In the heart of Rochesters picturesque village, this beautifully restored early 1900s building is a rare investment opportunity, offered as a single property with three fully furnished condo units. Perfect for an owner-occupant, a multi-generational retreat, or a savvy investor, this historic gem blends classic New

  Kate Cassidy Four Seasons Sotheby's Int'l Realty

  31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767
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  /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

  $2,495,000

  • 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
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  /41

  $1,495,000

  • 4 Beds
  • 1.5 Baths

  7 Slayton Terrace, Woodstock, VT 05091

  A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

  Keri Cole Williamson Group Sotheby's International Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /60

  $2,195,000

  • 5 Beds
  • 6 Baths
  • 5,625 Sq Ft

  16 Olcott Rd, Norwich, VT 05055

  16 OLCOTT ROAD- Elegant, spacious, and immaculate reproduction colonial constructed by premier builder Douglas Gest in an idyllic location minutes to Norwich Village yet privately set with lovely westerly views. This gorgeous home is well-appointed, bright, and has fine finish work at every turn. The main level flows effortlessly from a spacious kitchen and pantry to open concept dining and

  David Donegan Snyder Donegan Real Estate Group

  16 Olcott Rd, Norwich, VT 05055
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  /44

  $849,900

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

  117 Horseshoe Dr, Brownsville, VT 05037

  Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

  Katie Ladue Gilbert BHHS Verani Upper Valley

  117 Horseshoe Dr, Brownsville, VT 05037
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  /32

  $1,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,592 Sq Ft

  26 Mount Peg Rd Unit A, 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 A, Woodstock, VT 05091
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  /31

  $995,000

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

  26 Mount Peg Rd Unit B, 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 B, Woodstock, VT 05091
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  /38

  $795,000

  • 4 Beds
  • 3 Baths
  • 2,099 Sq Ft

  6077 Vt Route 12, Barnard, VT 05031

  BARNARD VILLAGE CAPE- This elegant Cape sits in an ideal location in the idyllic village of Barnard, just a short walk to the Barnard General Store and Silver Lake. The perfect blend of original charm, sophistication, and modern amenities, the house is bright and welcoming with lovely natural woodwork and plenty of space for social gatherings or quiet privacy. A large central living room features

  David Donegan Snyder Donegan Real Estate Group

  6077 Vt Route 12, Barnard, VT 05031
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  /52

  $849,000

  • 4 Beds
  • 4.5 Baths
  • 4,009 Sq Ft

  320 Old Bow Rd, Springfield, VT 05156

  Tucked away on a private road in Weathersfield, this property offers nearly 14 acres of open land, big sky, and clear views of Ascutney Mountain. A good portion of the land has already been cleared and is currently home to farm animals, so there is a head start here if that lifestyle appeals to you. You can keep it going as it is, expand into something more, or simply enjoy the open land for the

  Patrick Kelley Real Broker LLC

  320 Old Bow Rd, Springfield, VT 05156
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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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  /8

  $590,000

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

  0 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

  0 Wild Apple Rd, Pomfret, VT 05067
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  /16

  $3,150,000

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

  Markham Mountain, Andover, VT 05143

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

  Story Jenks LANDVEST

  Markham Mountain, Andover, VT 05143
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  /41

  $795,000

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

  115 Prior Rd, Cavendish, VT 05142

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

  Glenn Olney Barrett and Valley Associates Inc.

  115 Prior Rd, Cavendish, VT 05142
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  /60

  $699,000

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

  78 Coopers Trace, Plymouth, VT 05056

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

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  78 Coopers Trace, Plymouth, VT 05056
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  /44

  $749,000

  • 5 Beds
  • 2.5 Baths
  • 2,018 Sq Ft

  51 High St, Ludlow, VT 05149

  Welcome to 51 High Street — an immaculate, turnkey village home just steps from the Okemo shuttle stop, offering effortless access to Okemo Mountain Resort and all that Ludlow has to offer. This inviting residence features five bedrooms and 2.5 baths, thoughtfully updated for comfortable year-round living. The renovated kitchen shines with classic soapstone countertops and a charming Jøtul

  McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  51 High St, Ludlow, VT 05149
• 

  

  /38

  $614,000

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  62 Okemo Trailside Extension Unit 9-C, Ludlow, VT 05149

  Welcome to a place where comfort meets mountain lifestyle. This beautifully updated 3-bedroom, 2-bath condo offers the perfect blend of warmth, space, and convenience—just a short walk to the ski trail for effortless days on the mountain. Inside, you’ll find wood floors, a thoughtful open layout, and a cozy fireplace that anchors the living space, making it ideal for both quiet evenings and

  Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

  62 Okemo Trailside Extension Unit 9-C, Ludlow, VT 05149
• 

  

  /31

  $795,000

  • 3 Beds
  • 3.5 Baths
  • 2,282 Sq Ft

  3755 Quechee Main St Unit 9A, Quechee, VT 05059

  The perfect combination of feeling like a single family home but with the convenience and ease of townhouse living! Enjoy a park like setting with wonderful landscaping and stone walls throughout. Walk, bike or golf cart to the Quechee Club and Lake Pineo. Located adjacent to the 13th fairway of the Highland golf course. On site there is a beautiful in ground pool and two tennis courts for that

  Barbara Ruel Coldwell Banker LIFESTYLES - Quechee

  3755 Quechee Main St Unit 9A, Quechee, VT 05059

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