Windsor County VT Houses for Sale

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  /60

  $2,499,000

  • 4 Beds
  • 3.5 Baths
  • 5,079 Sq Ft

  254 Town Line Rd, Plymouth, VT 05056

  First time offered on market! Stunning VT private estate on over 22 +/- acres w/mountain views, gorgeous gardens & 2 ponds one of which is a 7-feet-deep spring fed glacial pond. This exquisite property has been meticulously designed & custom crafted by the owner who is a well-known respected master builder. As you enter this gem you will experience the thoughtful care everywhere you look.

  Marni Rieger KW Vermont-Killington

  254 Town Line Rd, Plymouth, VT 05056
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  /42

  $4,500,000

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

  85 Pallottas Hill Rd, Ludlow, VT 05149

  MAJOR 7 FIGURE PRICE REDUCTION! Your Vermont Mountain Retreat Awaits Discover 127 acres of pure Vermont beauty at the foot of Okemo Mountain, just 2 minutes from downtown Ludlow. This rare property offers expansive meadows, forested trails, and panoramic views of Okemo, Mount Ascutney and beyond. Enjoy direct access to cross country skiing, hiking, snowshoeing, the VAST trail system, and

  Frank Provance Diamond Realty

  85 Pallottas Hill Rd, Ludlow, VT 05149
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  /14

  $1,560,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,120 Sq Ft

  7034 Hiram Atkins Byway Rd Unit 7043, Hartford, VT 05059

  To be built by Mountain Stream at Quechee Lakes, the Thistle offers 3,120 square feet of contemporary living across two levels. The main floor includes kitchen, dining, and living areas with fireplace, along with a mudroom, half bath, and two bedrooms — each with a private full bathroom. The lower level features a garage or heated storage area, laundry and mechanical rooms, a family room, and two

  Richard Higgerson Higgerson & Company

  7034 Hiram Atkins Byway Rd Unit 7043, Hartford, VT 05059
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  /36

  $369,000

  • 5 Beds
  • 1 Bath
  • 2,243 Sq Ft

  2029 N Hill Rd, Chester, VT 05143

  Come, enjoy the quiet charm of Andover in this inviting, private Vermont home—perfect for year-round living or a peaceful getaway. Nestled among evergreens with beautiful snowy views, this property offers easy access to Okemo Mountain, and is also close to Stratton, Magic, and Bromley for skiing, riding, and four-season adventure. Snowmobile enthusiasts will love the nearby VAST trails, and the

  Daire Gibney Barrett and Valley Associates Inc.

  2029 N Hill Rd, Chester, VT 05143
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  /60

  $4,999,000

  • 5 Beds
  • 4.5 Baths
  • 9,170 Sq Ft

  62 Moonshadow Dr Unit M4 & M5, Ludlow, VT 05149

  Welcome to one of Okemo’s most distinctive properites, an iconic SKI-ON, SKI-OFF Tennessee log-style home set directly on the Moon Shadow ski trail within Solitude Village. This home offers the ultimate slopeside lifestyle with panoramic mountain views stretching across the Okemo Valley. Crafted with authentic log construction, showcasing broad hewn timbers, wide chinking, reclaimed wood floors,

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  62 Moonshadow Dr Unit M4 & M5, Ludlow, VT 05149
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  /46

  $215,000

  • 3 Beds
  • 1.5 Baths
  • 2,121 Sq Ft

  222 River St, Bethel, VT 05032

  Nestled on over an acre of serene countryside, this 3-bedroom, 2-bathroom home offers endless potential for those seeking a peaceful retreat with room to make it their own. Enjoy the beauty of nature with direct river frontage, perfect for fishing, kayaking, or simply relaxing to the soothing sounds of the water. The home features a spacious layout with abundant natural light, offering a cozy

  Flex Realty Group Flex Realty

  222 River St, Bethel, VT 05032
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  /37

  $1,995,000

  • 4 Beds
  • 2.5 Baths
  • 3,839 Sq Ft

  198 Piper Hill Rd, Weston, VT 05161

  Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house

  Story Jenks LandVest, Inc/Woodstock

  198 Piper Hill Rd, Weston, VT 05161
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  /60

  $4,775,000

  • 7 Beds
  • 6.5 Baths
  • 6,624 Sq Ft

  924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149

  Perched in Solitude, one of Okemo’s most sought-after on-mountain neighborhoods, 924 Okemo Ridge Road offers exceptional slope access, sweeping long-range views, and the scale to comfortably bring generations together under one roof. With 7 bedrooms and 6.5 bathrooms, this is a true ski home—designed for gathering, hosting, and making memories year after year. The home delivers classic ski lodge

  Katherine Burns William Raveis Real Estate Vermont Properties

  924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149
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  /60

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,205 Sq Ft

  688 Hidden Heights Rd, Chester, VT 05143

  Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the

  Joseph Karl William Raveis Real Estate Vermont Properties

  688 Hidden Heights Rd, Chester, VT 05143
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  /50

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  95 Union St, Springfield, VT 05156

  CASH ONLY. This well-priced home is full of potential and ready for your cosmetic upgrades and a bit of sweat equity. Offering three bedrooms and two baths on a generous lot, it’s conveniently located near the hospital, shopping, and essential amenities. The spacious master bedroom features an ensuite bath, while the additional partially finished attic provides room for expansion or storage.

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  95 Union St, Springfield, VT 05156
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  /40

  $2,650,000

  • 5 Beds
  • 5.5 Baths
  • 6,188 Sq Ft

  113 N Village Rd, Ludlow, VT 05149

  This beautiful and very spacious newly constructed home, with energy efficient upgrades, has over 6,000 square feet of living space on three levels. Within walking distance to the slopes, located close to the Base Lodge area, this home has everything a ski home needs. Enter through the carefully crafted front door into one of the two mudrooms, or through the two car garage or by the side mudroom

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

  113 N Village Rd, Ludlow, VT 05149
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  /49

  $715,000

  • 4 Beds
  • 3.5 Baths
  • 2,654 Sq Ft

  760 E Ash Rd, Plymouth, VT 05056

  Spacious Hawk Resort Home with Scenic Views Enjoy the perfect blend of comfort, space, and mountain charm in this inviting Hawk home. Designed for family gatherings and entertaining, the generous open-concept living area features a beautiful fieldstone fireplace and updated greenhouse windows that bring in natural light and picturesque views. The primary suite offers a cozy fireplace, private

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  760 E Ash Rd, Plymouth, VT 05056
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  /58

  $1,499,000

  • 5 Beds
  • 5 Baths
  • 5,074 Sq Ft

  423 Taft Family Rd, Hartford, VT 05001

  RARE OPPORTUNITY to own a fully renovated luxury home in Quechee Lakes with spectacular mountain views and over 5,000 sq ft of versatile living space on a 4.3-acre double lot. Updated throughout in 2023–2024 and now back on the market due to a professional relocation. This 5-bedroom, 5-bath luxury home offers substance and versatility to suit any new owners’ needs. A private studio apartment with

  Marco Day BHHS Verani Upper Valley

  423 Taft Family Rd, Hartford, VT 05001
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  /59

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,800 Sq Ft

  248 Gird Lot Rd, Weathersfield, VT 05151

  Perched above the Connecticut River Valley with sweeping views to the New Hampshire mountains, this meticulously maintained five bedroom, four and a half bath home offers a rare opportunity just 30 minutes to Hanover, NH, Dartmouth College, and Dartmouth Hitchcock Medical Center. For medical professionals relocating to the Upper Valley, this property provides privacy, acreage, and panoramic views

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
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  /59

  $3,100,000

  • 5 Beds
  • 4.5 Baths
  • 7,634 Sq Ft

  165 Moonshadow Dr Unit M-15, Ludlow, VT 05149

  Welcome to your mountain sanctuary in the heart of Solitude Village—Okemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great

  Joseph Karl William Raveis Real Estate Vermont Properties

  165 Moonshadow Dr Unit M-15, Ludlow, VT 05149
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  /49

  $950,000

  • 4 Beds
  • 3 Baths
  • 2,618 Sq Ft

  211 Abnaki Trace, Hartford, VT 05001

  Stunning! Completely renovated- This is a fantastic turn-key home with all of the modern upgrades buyers are looking for. All the bathrooms have been tiled with stone-top vanities. Stunning, renovated kitchen with navy/dark gray cabinetry accented with stone counters, new appliances and tiled back splash. Wood floors throughout, open concept for easy entertaining for guests and family. Vaulted

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  211 Abnaki Trace, Hartford, VT 05001
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  /41

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,532 Sq Ft

  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 Sothebys Intl. Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /26

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  160 Depot St, Chester, VT 05143

  Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

  Joshua Lemieux Remax Summit

  160 Depot St, Chester, VT 05143
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  /47

  $535,000

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  400 E Lake Rd, Ludlow, VT 05149

  Versatile Ludlow retreat on 9 acres with proven short-term rental history, offering flexible living options ideal for owner-occupants or investors seeking income near Okemo Mountain. This property is configured as a single-family residence with two distinct living levels, each featuring private entrances and amenities that allow for multiple use scenarios. The ground floor living area includes a

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

  400 E Lake Rd, Ludlow, VT 05149
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  /40

  $3,500,000

  • 6 Beds
  • 6 Baths
  • 5,433 Sq Ft

  61 Academy Cir, Woodstock, VT 05071

  Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

  Carol Wood Williamson Group Sothebys Intl. Realty

  61 Academy Cir, Woodstock, VT 05071
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  /60

  $3,650,000

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

  348 Turtle Hill Rd, Ludlow, VT 05149

  Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited on over 13 acres, the property offers sweeping, panoramic views of southern Vermont's mountains and valleys; vistas that are truly second to none. The home's architectural highlights include hand-hewn Douglas fir beams

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  348 Turtle Hill Rd, Ludlow, VT 05149
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  /59

  $325,000

  • 5 Beds
  • 2 Baths
  • 2,400 Sq Ft

  54 Twitchell Settlement, Rochester, VT 05767

  PRICE REDUCTION TODAY - NOW OFFERED AT $325,000 (PREVIOUSLY $410,000). Set in Rochester, this chalet-style single family home pairs a dramatic vaulted great room with cathedral ceilings and an arched window wall that pours in natural light and captures seasonal mountain views. The setting spans 3.20 acres with a mix of open field and wooded privacy, giving you room to spread out while enjoying a

  Nick Sicard EXP Realty

  54 Twitchell Settlement, Rochester, VT 05767
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  /60

  $999,000

  • 6 Beds
  • 7.5 Baths
  • 5,588 Sq Ft

  726 E Ash Rd, Plymouth, VT 05056

  Nestled on a 3-acre private lot at Hawk Resort in Vermont’s Lakes Region, this expansive custom residence offers an exceptional mountain retreat. Thoughtfully designed across four levels--each accessible by elevator--the home provides outstanding separation of space, perfect for hosting family and guests.Designed by architect Robert Carl Williams, the home showcases signature craftsmanship,

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  726 E Ash Rd, Plymouth, VT 05056
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  /32

  $445,000

  • 3 Beds
  • 3 Baths
  • 2,074 Sq Ft

  259 Jay Hill Rd, Hartford, VT 05001

  Bright, easy to maintain and furnished 3 bedroom, 3 bath house with all that Quechee Lakes has to offer. This home includes newer floors. kitchen appliances, 2 remodeled bathrooms, a whole house generator, and a garage with an electric car charger. Enjoy the outdoors with a large deck and an electric dog fence around the whole house.

  Sandra Dell KW Coastal and Lakes & Mountains Realty/Hanover

  259 Jay Hill Rd, Hartford, VT 05001
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  /53

  $390,000

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft

  531 Main St, Chester, VT 05143

  Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area

  Katherine Burns William Raveis Real Estate Vermont Properties

  531 Main St, Chester, VT 05143
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  /60

  $1,250,000

  • 6 Beds
  • 5.5 Baths
  • 5,790 Sq Ft

  49 Burton Rd, Weston, VT 05161

  “Meadow & Mountain View” is the Vermont home you’ve been waiting for! Situated just outside of the charming village of Weston, this impressive property offers one of the area’s most delightful and picturesque locations with fantastic views, beautiful grounds, and a warm and welcoming house designed so that you can relax and truly enjoy your Vermont Life. The inviting layout features classic New

  Claudia Harris Mary Mitchell Miller Real Estate

  49 Burton Rd, Weston, VT 05161
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  /58

  $385,000

  • 4 Beds
  • 2 Baths
  • 2,554 Sq Ft

  1806 Vermont Route 100, Rochester, VT 05767

  This historic cape, circa 1785, is one of the oldest homes in Rochester, VT, blending timeless charm with modern updates. Centrally located to Sugarbush Resort along with Killington Resort and Pico Mountain. Its exposed beams, hand-built doors, and wide pine plank floors evoke classic New England architecture, while recent upgrades ensure comfort and convenience. Major enhancements include new

  Nathan Mastroeni

  1806 Vermont Route 100, Rochester, VT 05767
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  /37

  $585,000

  • 4 Beds
  • 4 Baths
  • 3,934 Sq Ft

  46 Runnals Rd, White River Junction, VT 05001

  Step into timeless character and modern comfort in this unique 4-bedroom, 4-bathroom home. A thoughtful 1984 expansion preserved the original home's historic core featuring a rare early American beehive oven and three-hearth fireplace, while adding over 3,200 sq. ft. of spacious living and a 1,000 sq. ft. in-law apartment. There’s room for everyone here. The sun-drenched kitchen and dining area

  Cheryl Herrmann RE/MAX Group One Realtors

  46 Runnals Rd, White River Junction, VT 05001
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  /46

  $699,000

  • 4 Beds
  • 3.5 Baths
  • 2,998 Sq Ft

  38 Ozzy Ln, White River Junction, VT 05001

  Welcome home! This energy efficient four bedroom, four bath home was completed in 2019. Perfectly located in the heart of the Upper Valley, only 10 minutes to downtown Hanover and 15 minutes to DHMC. This bright and sunny home is set on a quiet neighborhood street with beautiful mountain views. The thoughtfully designed layout balances everyday living with private retreat spaces.The open

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  38 Ozzy Ln, White River Junction, VT 05001
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  /41

  $579,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 3,080 Sq Ft

  1631 Christian St, White River Junction, VT 05001

  Extraordinary views and modern efficiency define this extensively renovated smart home on Christian Street in Wilder, VT. Ideally located just 6 minutes to Dartmouth College and 14 minutes to Dartmouth Health, this property offers both convenience and exceptional functionality. Recent major upgrades include a completely new kitchen, updated bathrooms, new furnace, upgraded 200-amp electrical

  Gerry Stark RE/MAX Upper Valley

  1631 Christian St, White River Junction, VT 05001
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  /41

  $845,000

  • 2 Beds
  • 1.5 Baths
  • 1,714 Sq Ft

  403 Horse Shoe Way, Woodstock, VT 05071

  Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  403 Horse Shoe Way, Woodstock, VT 05071
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  /60

  $825,000

  • 5 Beds
  • 5 Baths
  • 3,886 Sq Ft

  3961 Hartland Hill Rd, Woodstock, VT 05091

  NEW PRICE! This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor

  Tambrey Vutech KW Vermont Woodstock

  3961 Hartland Hill Rd, Woodstock, VT 05091
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  /60

  $599,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  5100 Route 100, Plymouth, VT 05056

  (Das Grünebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

  Marni Rieger KW Vermont-Killington

  5100 Route 100, Plymouth, VT 05056
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  /47

  $550,000

  • 3 Beds
  • 3.5 Baths
  • 2,727 Sq Ft

  1787 Route 100 N, Ludlow, VT 05149

  From location to layout, this home offers the best of Vermont living. Set along scenic Route 100 in the heart of the lakes region, you’ll enjoy year-round recreation just minutes from Okemo Mountain Resort, Killington Resort, and Plymouth State Park. This thoughtfully remodeled farmhouse blends classic charm with modern updates. Offering 3 bedrooms and 3.5 bathrooms, the home features generous

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  1787 Route 100 N, Ludlow, VT 05149
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  /55

  $915,000

  • 3 Beds
  • 3 Baths
  • 2,150 Sq Ft

  509 Church Hill Rd, Wood Stock, VT 05091

  Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

  Carol Wood Williamson Group Sothebys Intl. Realty

  509 Church Hill Rd, Wood Stock, VT 05091
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  /35

  $495,000

  • 4 Beds
  • 3 Baths
  • 2,470 Sq Ft

  3364 W Woodstock Rd, Woodstock, VT 05091

  Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway. Inside, you’ll find four comfortable bedrooms and a warm, inviting layout designed for making memories. Gather

  Keri Cole Williamson Group Sothebys Intl. Realty

  3364 W Woodstock Rd, Woodstock, VT 05091
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  /19

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  130 Pleasant St, Cavendish, VT 05142

  This home has served as a primary residence and also as an income-producing rental. While the upper level of this home has three bedrooms, the walk-out lower level of the home has such potential as well.It is currently partially finished and is being used as a family room and for storage. The large deck on the end of the house is perfect for taking in some fresh Vermont air or grilling for

  Tyleen Murray Kelley Real Estate, Inc.

  130 Pleasant St, Cavendish, VT 05142
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  /31

  $425,000

  • 2 Beds
  • 1 Bath
  • 908 Sq Ft

  1873 Old River Rd, White River Junction, VT 05001

  Super cute, renovated two bedroom home. Detached garage for some extra storage. Only 15 minutes to Dartmouth Hitchcock & Dartmouth College. Being 2.5 acres, there is plenty of room to expand if you wanted to!

  Lyndsey Freeman Quechee Lakes Real Estate Center

  1873 Old River Rd, White River Junction, VT 05001
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  /16

  $1,675,000 New Construction

  • 5 Beds
  • 3 Baths
  • 3,837 Sq Ft

  4071 Tichnor Rd Unit 4071, Hartford, VT 05001

  To be built by Mountain Stream at Quechee Lakes, the Walnut offers 3,837 square feet of living space across three levels. The main level features an open-concept kitchen and dining area, a spacious living room with fireplace, and access to a front terrace. The home includes five bedrooms, four bathrooms, and a recreation room, providing ample space for family and guests. Exterior design features

  Richard Higgerson Higgerson & Company

  4071 Tichnor Rd Unit 4071, Hartford, VT 05001
• 

  

  /40

  $799,000

  • 7 Beds
  • 9 Baths
  • 7,428 Sq Ft

  52 Upper, Bridgewater, VT 05035

  The ideal property for a SKI CLUB! 7 bedrooms! 6 bathrooms! An immaculate, professionally appointed commercial kitchen! Spacious common rooms and dining areas! A classic and inviting bar/lounge area! An interior with the true Vermont style appeal of exposed beams, wood floors and a stone faced fireplace! This inviting New England style building is perfectly situated midway between world class

  John Wetmore Wetmore Real Estate

  52 Upper, Bridgewater, VT 05035

Showing Results 41 - 80, Page 2 of 5