Windsor County VT Houses for Sale

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  /58

  $985,000

  • 2 Beds
  • 3 Baths
  • 1,586 Sq Ft

  2865 Bridgewater Hill Rd, Bridgewater Corners, VT 05035

  Welcome to "Green Shutters," an exceptional 20-acre Vermont homestead that seamlessly bridges late-1800s heritage with state-of-the-art, sustainable luxury. While technically a two-bedroom, this highly versatile property offers far more space, featuring a fully renovated circa 1895 farmhouse and a striking modern addition with an oversized heated two-car garage, private guest suite, and multiple

  

  KC Gandee

  Real Broker LLC

  2865 Bridgewater Hill Rd, Bridgewater Corners, VT 05035
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  /52

  $799,000

  $50K PRICE DROP

  • 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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  /47

  $1,650,000

  $245K 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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  /52

  $599,000

  • 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

  583 Hawk Spur Rd, Plymouth, VT 05056
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  /60

  $475,000

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

  7868 Pomfret Rd, North Pomfret, VT 05053

  HAVING A HARD TIME FINDING AN AFFORDABLE LIVING SITUATION? With multiple income streams already established, this property offers a rare opportunity to choose your living preference (2 Bdrms, 1 Bdrm, or Efficiency) and offset almost ALL of your living expenses while owning a historic small town landmark. Originally established as the North Pomfret Store & Post Office c.1830, this classic 3-story

  

  John Bassette

  Bassette Real Estate Group

  7868 Pomfret Rd, North Pomfret, VT 05053
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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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  /32

  $349,000

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft

  45 Reservoir Rd, Springfield, VT 05156

  First time offered in over 60 years, this well cared for 3 bedroom, 2 bath home is a rare opportunity to own a property that has been truly loved and maintained. Set on a spacious, level lot in an area of well kept homes, the property immediately stands out with its large lawn, ideal for outdoor enjoyment, gardening, or simply relaxing. Inside, you’ll find over 1,500 square feet of comfortable

  

  Patrick Kelley

  Real Broker LLC

  45 Reservoir Rd, Springfield, VT 05156
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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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  /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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  /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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  /23

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,767 Sq Ft

  165 Dutton Farm Rd, Springfield, VT 05156

  Bring your vision to this private 3-bedroom, 2-bath home with a bonus room, nestled in a sought-after location. Surrounded by nature, this property offers the peace and privacy you've been searching for while providing endless potential to make it your own. Enjoy beautiful views from the large living room windows, or venture outdoors to explore the near-by walking trails. Established herbs and

  

  Kirsten Dole

  Coldwell Banker LIFESTYLES - Hanover

  165 Dutton Farm Rd, Springfield, VT 05156
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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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  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft

  3051 Vt Rt 107, Stockbridge, VT 05772

  A rare chance to own a substantial slice of Vermont's countryside, with commercial upside built in. This 62-acre property spans both sides of VT Route 107, offering a diverse landscape along with the flexibility of a commercial zoning designation, opening the door to a range of business and development possibilities. On the south side, mature forested acreage includes a former sugarbush offering

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  3051 Vt Rt 107, Stockbridge, VT 05772
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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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  /38

  $750,000

  $45K PRICE DROP

  • 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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  /60

  $2,500,000

  • 4 Beds
  • 3.5 Baths
  • 5,127 Sq Ft

  114 Oak Ridge Way, Woodstock, VT 05091

  See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero

  Tami Sullivan Snyder Donegan Real Estate Group

  114 Oak Ridge Way, Woodstock, VT 05091
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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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  /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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  /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

  $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
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  /58

  $2,900,000

  $200K 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
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  /44

  $824,900

  $25K PRICE DROP

  • 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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  /28

  $889,000

  • 3 Beds
  • 3.5 Baths
  • 2,383 Sq Ft

  5723 Vt Rt 12 Route, Barnard, VT 05031

  Beautifully renovated, this Barnard Village Cape seamlessly blends modern energy- efficient upgrades with the timeless charm of a classic New England home. A spacious slate-floored mudroom welcomes you into a bright, inviting interior featuring all-new Renewal by Andersen windows and beautifully restored original maple floors. The thoughtfully designed main level includes a stylish kitchen with

  Mary Mayhew Snyder Donegan Real Estate Group

  5723 Vt Rt 12 Route, Barnard, VT 05031
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  /58

  $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 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 softened by the surrounding forest. The main level opens to

  Richard Higgerson Higgerson & Company

  399 Bentley Rd, Hartford, VT 05059
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  /54

  $750,000

  • 3 Beds
  • 2.5 Baths
  • 1,972 Sq Ft

  207 Hartness Way, Hartford, VT 05001

  Are you looking for the ideal energy efficient property, perhaps perfect as a 2nd home or investment opportunity? The Sellers have paid less than $3,300 per year covering all utilities for this premium energy efficient home. Discover the perfect blend of comfort, efficiency, and adventure in this beautifully designed, sunny and bright newer-build home, nestled within Vermont's coveted Quechee

  Tyler Hall BHHS Verani Upper Valley

  207 Hartness Way, Hartford, VT 05001
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  /58

  $579,000

  • 3 Beds
  • 2 Baths
  • 1,924 Sq Ft

  530 West Rd, Barnard, VT 05031

  Set just up West Road in Barnard, this inviting Cape-style home offers a classic Vermont setting: a peaceful wooded backdrop, warm interior character, and easy access to village life, Silver Lake, and the outdoors. The Barnard General Store and Silver Lake, with the town hall, town library, and newly constructed fire station, are nearby. West Road also serves as a way to head toward the

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  530 West Rd, Barnard, VT 05031
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  /38

  $1,599,000

  • 4 Beds
  • 3.5 Baths
  • 3,456 Sq Ft

  96 Echo View Dr, Plymouth, VT 05056

  Experience the perfect blend of luxury, comfort, and Vermont charm in this exceptional 3,456-square-foot home. Built with superior craftsmanship andmeticulous attention to detail, this residence reflects a commitment to quality where every finish was carefully selected and thoughtfully executed. No detail wasoverlooked, with premium materials and high-end finishes throughout, creating a home that

  Gail Beardmore Engel & Volkers Okemo

  96 Echo View Dr, Plymouth, VT 05056
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  /58

  $1,395,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  1522 Barnard Rd, Woodstock, VT 05091

  Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add

  Keri Cole Williamson Group Sothebys Intl. Realty

  1522 Barnard Rd, Woodstock, VT 05091
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  /60

  $29,000,000

  $10M PRICE DROP

  • 2 Beds
  • 7 Baths
  • 9,950 Sq Ft

  650 Francis Rd, Barnard, VT 05031

  Set on 400+/- acres in Barnard, Vermont, Monsalvat Farm is a legacy estate where rolling pastures, stone walls, forests, and mountain views reflect the state’s timeless character. Settled in 1793, the land carries generations of stewardship, elevated by one of the finest residences in the country—an architectural masterpiece complemented by historic and companion structures that are carefully

  Chris Lang

  650 Francis Rd, Barnard, VT 05031
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  /41

  $725,000

  $70K PRICE DROP

  • 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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  /30

  $3,500,000

  • 4 Beds
  • 3 Baths
  • 2,571 Sq Ft

  58 Lakeshore Dr, Ludlow, VT 05149

  One-of-a-kind Lake Rescue sanctuary with 179 feet of shoreline, stone walls, perennial gardens, apple trees, and a sprawling flat lawn perfect for games and gatherings. Offering exceptional flexibility, this special setting on 4.35 acres has the potential to become a family compound, multi-generational retreat, or income-producing investment. A 3-bedroom septic permit is already in place,

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  58 Lakeshore Dr, Ludlow, VT 05149
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  /56

  $519,000

  $30K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,704 Sq Ft

  37 Robinson Ave, Rochester, VT 05767

  This beautifully updated property in charming Rochester, VT offers exceptional flexibility for investors or owner-occupants. Five bedrooms in total this home has space for everyone. All units have been nicely updated throughout and are well-suited for short or long-term rental, with a strong STR income history already in place. Major system upgrades include a new standing seam roof, new furnace,

  Nathan Mastroeni

  37 Robinson Ave, Rochester, VT 05767
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  /39

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,308 Sq Ft

  76 Goldthwaite Rd, Chester, VT 05143

  Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

  Gary Coger Four Seasons Sotheby's Int'l Realty

  76 Goldthwaite Rd, Chester, VT 05143
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  /44

  $729,000

  $20K PRICE DROP

  • 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
• 

  

  /36

  $480,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,122 Sq Ft

  1138 Bethel Mountain Rd, Rochester, VT 05767

  Set on 4.7± acres along scenic Bethel Mountain Road, this mountain-view property offers the kind of Vermont experience that you're yearning for. With a swimming pond, expansive outdoor living spaces, detached three-car garage, and easy access to some of the state’s best outdoor recreation, this is a home designed to be enjoyed in every season. The setting is exceptional. Long-range mountain views

  William Brokhof Vermont Backcountry Real Estate

  1138 Bethel Mountain Rd, Rochester, VT 05767
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  /29

  $530,000

  • 3 Beds
  • 2.5 Baths
  • 4,020 Sq Ft

  28 Fairview Terrace, Royalton, VT 05068

  This 3-bedroom, 2.5-bath home is full of potential, with the option to create an auxiliary dwelling for added flexibility. The current owner saw the promise in this gem and has already invested in the important updates: fresh exterior paint, a brand-new septic system, a new roof, upgraded electrical, and other quality improvements. With much of the essential work complete, the next owner has the

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  28 Fairview Terrace, Royalton, VT 05068
• 

  

  /36

  $299,000

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft

  29 Markham Ln, Weston, VT 05161

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

  Catherine Cairns Maple Leaf Real Estate

  29 Markham Ln, Weston, VT 05161
• 

  

  /36

  $510,000

  $25K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 4,933 Sq Ft

  2 Pine St, Windsor, VT 05089

  Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch

  Susan Bellville Bellville Realty

  2 Pine St, Windsor, VT 05089
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  /60

  $1,199,000

  $51K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 3,123 Sq Ft

  292 Hard Rd, Hartford, VT 05001

  Rooted in the traditions of New England architecture and thoughtfully built for modern living, this colonial reproduction occupies a special place within Quechee Lakes, Vermont's premier four-season community.Inspired by a Connor Historic Federal farmhouse design and constructed by one of the region's most respected builders, the home reflects a level of craftsmanship that is increasingly

  Richard Higgerson Higgerson & Company

  292 Hard Rd, Hartford, VT 05001

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