Windsor County VT Homes for Sale

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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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  /15

  $237,000

  • Land
  • 221 Acres
  • $1,072 per Acre

  0 New Boston Rd, Thetford, VT 05074

  IntroductionThe ownership is selling their property in two separate parcels, divided by the town line. The +/-60 acre Strafford parcel is well suited to future home development with paved town road frontage and roadside electric service. The +/-220 acre Thetford parcel is well suited to a camp or seasonal off-grid home development with beautiful local views.Both parcels have

  John Latham Fountains Land

  0 New Boston Rd, Thetford, VT 05074
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  /24

  $217,500

  • Land
  • 94 Acres
  • $2,314 per Acre

  6416 Vermont 107, Stockbridge, VT 05772

  Nestled among natural streams in the rolling hills of Vermont’s Green Mountains, this remarkable 94-acre parcel offers sweeping views overlooking the White River. Rich with potential for residential use or future development, the property includes a private septic system and a drilled well already in place. With 670 feet of frontage along VT Route 107, the land provides convenient access while

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  6416 Vermont 107, Stockbridge, VT 05772
• 

  

  

  /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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  /17

  $53,000

  • Land
  • 1.5 Acres
  • $35,333 per Acre

  2-66 Goshawk Dr, Plymouth, VT 05056

  Dreaming of building your own Vermont-style home but hoping to find an affordable parcel? This lot at Hawk Resort is the perfect opportunity. With power and other utilities already on site and the ability to connect to the community septic system, you’ll be well on your way to breaking ground on your dream home. Tucked among the trees in a peaceful natural setting, this property offers privacy

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  2-66 Goshawk Dr, Plymouth, VT 05056
• 

  

  /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
• 

  

  /25

  $115,000

  • Land
  • 10 Acres
  • $11,500 per Acre

  S-1C Great Roaring Brook Rd, Plymouth, VT 05056

  Ten-acre wooded parcel with potential views located near the top of Great Roaring Brook Rd. The topography is rolling too steep with multiple buildings sites, rock crop outs, and streams throughout. A wonderful opportunity to design and build your Vermont dream home. Located between Ludlow and Woodstock with equal distance to Killington and Okemo Ski areas. Close to Lake Rescue and Echo Lake for

  Terry Davis Williamson Group Sothebys Intl. Realty

  S-1C Great Roaring Brook Rd, Plymouth, VT 05056
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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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  /36

  $95,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149

  Experience Vermont's Premier Mountain Living Without Full Ownership Costs. Step directly onto Okemo's slopes from your slopeside retreat at Jackson Gore. This condo-tel quarter-share gives you deeded ownership of 13 weeks annually (25% of the year)—at a fraction of the cost of whole ownership. You own one of four deeded interests in this unit. You receive every fourth week on a rotating schedule,

  Rachael Lange Lange & Lange

  224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149
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  /12

  $199,000

  • Land
  • 29 Acres
  • $6,862 per Acre

  00 Vermont 12, Barnard, VT 05031

  A beautiful and private 29 acre building lot on a mountainside in an area of Barnard populated by estate properties. A road to the potential building site is in and soil testing for septic will be completed as soon as snow clears. Views of the valley and local mountains currently cleared and can be expanded with additional clearing. The location is a short drive to Woodstock, a shorter drive to

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Vermont 12, Barnard, VT 05031
• 

  

  /3

  $175,000

  • Land
  • 12.51 Acres
  • $13,989 per Acre

  377 Coach Rd, Chester, VT 05143

  Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

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

  377 Coach Rd, Chester, VT 05143
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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
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  /36

  $500,000

  • 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
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  /13

  $215,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  122 Quechee Hollow Ln Unit 4E, Hartford, VT 05059

  Welcome to easy living in Quechee Lakes! This charming 2-bedroom condo offers a cozy, traditional style that feels warm and inviting from the moment you arrive. Neat, tidy, and well-maintained, it's the perfect retreat for year-round enjoyment or a convenient getaway. As part of the Quechee Lakes community, you'll have access to an outstanding array of amenities, including championship golf,

  Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  122 Quechee Hollow Ln Unit 4E, Hartford, VT 05059
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  /31

  $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
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  /4

  $169,000

  • Land
  • 15.4 Acres
  • $10,974 per Acre

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091

  Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a

  Chelsea Bevis KW Vermont Woodstock

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091
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  /20

  $169,000

  • Land
  • 22,651 Sq Ft
  • $325,000 per Acre

  71 S Windsor St, Royalton, VT 05068

  Centrally located, in the picturesque village of South Royalton, is a building lot with multifaceted potential! The desirable attributes of both the ability for connection to the municipal sewer and connection to the municipal water system could present the opportunity for multi-unit residential construction! An extensive level lawn area makes visualizing prospective building sites a simple

  John Wetmore Wetmore Real Estate

  71 S Windsor St, Royalton, VT 05068
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  /36

  $515,000

  $20K 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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  /12

  $79,000

  • Land
  • 2.53 Acres
  • $31,225 per Acre

  Lot #4 Meadow Rd, Ludlow, VT 05149

  Private 2.53+/- acre state approved building lot located at the end of a dead-end, private road. Positioned at the south end of Ludlow off East Hill Road, this lot offers easy access to town amenities and the Okemo Ski Area. Possible views of Okemo with clearing.

  Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  Lot #4 Meadow Rd, Ludlow, VT 05149
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  /20

  $85,000

  • Land
  • 3.99 Acres
  • $21,303 per Acre

  00 Simonsville Rd, Andover, VT 05143

  ANDOVER 3.99 Acres on the Williams River that was once a part of the Historic Jaquith Homestead. Walk the old mowing road that winds through the property, leading to three meadow areas along the river. The central meadow has a designated home site for a 4 bedroom state approved septic. The owners have just had the house location resighted to make sure it is out of the flood zone. A great spot for

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Simonsville Rd, Andover, VT 05143
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  /6

  $195,000

  • Land
  • 1 Acre
  • $195,000 per Acre

  Lot 48 Partridge Rd, Ludlow, VT 05149

  1.01+/- acres. Lot 48. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

  Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

  Lot 48 Partridge Rd, Ludlow, VT 05149
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  /60

  $1,250,000

  • 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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  /41

  $1,576,000

  • 9,455 Sq Ft

  14 Summarsell Dr Unit 16, Hartland, VT 05048

  This charming converted farmstead features two primary buildings on one parcel, combining classic Vermont character with solid investment returns. The property offers a diverse mix of one-, two-, and four-bedroom apartments, plus one commercial unit currently leased to a local bath and body company. Additional income comes from a three-bay garage, a shed, and a storage container — all fully

  Loren Wehmeyer Tesla Realty Group, LLC

  14 Summarsell Dr Unit 16, Hartland, VT 05048
• 

  

  /31

  $795,000

  $50K PRICE DROP

  • 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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  /20

  $460,000

  $135K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,228 Sq Ft

  145 Okemo Trailside Extension Unit 23C, upper, Ludlow, VT 05149

  Walk to the Sachem Trail from this recently remodeled, warm and charming, 2 bedroom, 2 bath, 2 level condominium. Easy maintenance with an open floor plan (kitchen, dining and living room with wood burning fireplace and slider to the deck). Updates include: new kitchen cabinets, granite countertops, wood plank flooring, carpet, and paint. The new bathrooms have large format tiling and frameless

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

  145 Okemo Trailside Extension Unit 23C, upper, Ludlow, VT 05149
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  /20

  $599,000

  $190K PRICE DROP

  • Land
  • 33 Acres
  • $18,152 per Acre

  00 Olcott Rd Unit 189, Norwich, VT 05055

  This 33-acre estate-quality parcel is offered with conceptual drawings and a fully permitted four-bedroom wastewater system design, presenting an exceptional opportunity to build in a prime Upper Valley location. Overlooking and bordering conserved land, the property is located just 1.5 miles from the center of Norwich, Vermont. Its close proximity to downtown Hanover, NH, and Dartmouth College,

  Richard Higgerson Higgerson & Company

  00 Olcott Rd Unit 189, Norwich, VT 05055
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  /48

  $2,500,000

  • 6 Beds
  • 6 Baths
  • 7,019 Sq Ft

  5518 Vermont 12, Barnard, VT 05031

  This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family. Now, with children grown and off on their own paths, it is time to pass stewardship of the historic

  Laird Bradley Williamson Group Sothebys Intl. Realty

  5518 Vermont 12, Barnard, VT 05031
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  /58

  $485,000

  • 8 Beds
  • 1 Bath
  • 3,500 Sq Ft

  1254 U S 5, Springfield, VT 05156

  Welcome to the former Danforth Inn! Take a trip back in time to 1780 as you look at this extremely original old building that was built in Weathersfield Bow in 1780 by Gideon Lyman. In 1789 Joseph Danforth moved to the Bow and he leased and then bought the Inn, changing the name to the Danforth Inn. This property will need some love, but it has never been spoiled in its originality, and it's just

  Glenn Olney Barrett and Valley Associates Inc.

  1254 U S 5, Springfield, VT 05156
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  /48

  $502,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  88 Happy Valley Rd, Woodstock, VT 05091

  Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including

  Julie Davis KW Vermont Woodstock

  88 Happy Valley Rd, Woodstock, VT 05091
• 

  

  /13

  $1,525,500

  New Construction

  • 4 Beds
  • 4 Baths
  • 2,752 Sq Ft

  5677 Hendee Way, Hartford, VT 05001

  The Jasper at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Jasper offers 2,752 square feet of refined single-level living, paired with a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic central chimney give the home a distinctly modern presence — clean architectural lines softened by the

  Richard Higgerson Higgerson & Company

  5677 Hendee Way, Hartford, VT 05001
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  /47

  $149,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft

  49 Clay Hill Rd, Hartland, VT 05048

  Partially finished circa 1998 26' x 24' ranch house on 2 lots totalling 1.76+/- acres. This fixer-upper has been lived in year round since its construction but never fully finished. The space consists of a kitchen that opens into a single main room being used as a living room, bedroom and dining area. Both the interior and exterior wall surfaces need finishing in places. The interior needs

  Steve Schoppmeyer BHG Masiello Brattleboro

  49 Clay Hill Rd, Hartland, VT 05048
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  /22

  $85,000

  • Land
  • 5 Acres
  • $17,000 per Acre

  0 Linden Way Unit 5093908, Chester, VT 05143

  Privacy doesn't have to mean isolation!!Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a

  Daire Gibney Barrett and Valley Associates Inc.

  0 Linden Way Unit 5093908, Chester, VT 05143
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  /30

  $350,000

  • 4 Beds
  • 2 Baths
  • 1,373 Sq Ft

  35 Andover St, Ludlow, VT 05149

  This is a great opportunity. A turnkey unit in a super location in the village where you can walk to restaurants, shops, little league field and pickle ball courts all within a single block. It doesn't get any better. There are four units in the building. All of them are upstairs/downstairs unit. No chance of someone above or below you disrupting your peace and quiet. On the first level is the

  Betty McEnaney Diamond Realty

  35 Andover St, Ludlow, VT 05149
• 

  

  /16

  $3,150,000

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

  00 Marsh Cross Rd, 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, Inc/Woodstock

  00 Marsh Cross Rd, Andover, VT 05143
• 

  

  /14

  $69,000

  • Land
  • 1.05 Acres
  • $65,714 per Acre

  Lot 49 Spring St, Stockbridge, VT 05772

  Attractive building lot in the desirable Highwood community. This lot offers potential long-range views and includes sewer rights in the Highwood community sewer system, sufficient for a three-bedroom residence. Architectural review and protective covenants ensure that the quality of life in this small community is always preserved. Highwood is adjacent to the Green Mountain Trail network for

  Kyle Kershner Killington Pico Realty

  Lot 49 Spring St, Stockbridge, VT 05772
• 

  

  /36

  $845,000

  $50K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,840 Sq Ft

  49 Vt Rt 12, Pomfret, VT 05053

  Discover the possibilities with this beautifully crafted three bedroom, three and one half bath home and versatile Post and Beam barn/studio, set between Woodstock and Silver Lake in scenic Barnard. The main residence features an airy great room with vaulted ceilings, warm wood accents, and expansive windows that invite natural light and frame peaceful views. Thoughtful design and quality

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  49 Vt Rt 12, Pomfret, VT 05053
• 

  

  /60

  $4,999,000

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

  62 Moon Shadow Dr, 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 Moon Shadow Dr, Ludlow, VT 05149
• 

  

  /31

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  111 Lakeland Dr Unit 6B, Quechee, VT 05059

  Welcome to this sunny, immaculate condominium in Lakeland Village — just in time for summer enjoyment! Often considered one of the most desirable developments in Quechee Lakes, Lakeland Village offers exceptional convenience with easy walking or golf cart access to two championship golf courses, Lake Pinneo, indoor and outdoor pools, tennis courts, and the clubhouse. This turnkey property is

  Mary Paino Coldwell Banker LIFESTYLES - Quechee

  111 Lakeland Dr Unit 6B, Quechee, VT 05059

Showing Results 41 - 80, Page 2 of 12