Windsor County VT Homes for Sale

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  /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
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  /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
• 

  

  

  /35

  $105,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  246/248 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Unit 246/248, Quarter I: Quarter ownership. Located on the second floor, convenient to the pool, fitness room and the ski base areas! Great two bedroom / lock-out capabilities. Unit J Features:2 Bedrooms, Sleeps eight, Lock out capability, King bed, Queen bed, Queen sleep sofa, Double sleep sofa, full kitchen, covered balcony, jetted bath tub, fireplace, entertainment center. Come and enjoy what

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  246/248 Qtr I Jackson Gore Inn, Ludlow, VT 05149
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  /26

  $149,000

  • Land
  • 0.23 Acre
  • $647,826 per Acre

  0 Prospect St Unit 5063213, Ludlow, VT 05149

  Here's your opportunity to purchase Ludlow's newest village lot offering. Lot 3 is located on the right side of the road and is the last lot on the street. Lot 3 is a nice level lot with endless possibilities. It has partial views of Okemo Mountain, and you'll see some spectacular sunsets. Ludlow's restaurants, shops, and parks are just a short walk away, and Okemo Mountain is about a mile away.

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Prospect St Unit 5063213, Ludlow, VT 05149
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  /44

  $439,000

  • 2 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  339 Ranney Rd, Stockbridge, VT 05772

  Take a look at this home in central Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 2 acre lot with plenty of sun and space for pets, gardens or greenhouses. An adjoining 1 acre house lot can be purchased for an additional 30k if interested now. This Stockbridge home has an extra living apartment below- accessible by a separate driveway. It provides

  Risa Mornis Covered Bridge RE

  339 Ranney Rd, Stockbridge, VT 05772
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  /58

  $3,490,000

  • 4 Beds
  • 4.5 Baths
  • 2,894 Sq Ft

  1726 Skitchewaug Trail, Springfield, VT 05156

  A circa 1734 Cape, displaying museum quality authentic detailing, in a setting worthy of a Vermont Life Magazine cover! Originally sited in N.H., the Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The interior seamlessly blends early New England architectural features with benefits of contemporary design amenities.

  John Wetmore Wetmore Real Estate

  1726 Skitchewaug Trail, Springfield, VT 05156
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  /14

  $289,000

  • 2 Beds
  • 2.5 Baths
  • 1,475 Sq Ft

  106 Contro Rd, Chester, VT 05143

  Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

  Christine Lewis Brattleboro Area Realty

  106 Contro Rd, Chester, VT 05143
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  /7

  $1,250,000

  • Land
  • 0.34 Acre
  • $3,676,471 per Acre

  130 Main St, Ludlow, VT 05149

  For generations, the Pot Belly building was a familiar and beloved part of Ludlow Village—a place where locals and visitors gathered, stories were shared, and the energy of the village came to life. Today, the building may be gone, but the opportunity it created is just beginning.Now offered as a prime, cleared village lot, this property represents a rare chance to be part of Ludlow’s next

  Joseph Karl William Raveis Real Estate Vermont Properties

  130 Main St, Ludlow, VT 05149
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  /60

  $200,000

  • 3 Beds
  • 3 Baths
  • 2,011 Sq Ft

  625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149

  Jackson Gore area of Okemo– Adams House Quarter Share Ownership, Unit 625/627 Quarter III (includes Christmas weeks for 2026). Enjoy slopeside living with mountain views in this three-bedroom, three-bathroom condominium with just over 2000 square feet of living space. Located within The Adams House at Jackson Gore on Okemo, offering direct slope access. Enjoy luxury living with full access to The

  Kevin Barnes William Raveis Real Estate Vermont Properties

  625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149
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  /45

  $499,000

  • 3 Beds
  • 1.5 Baths
  • 2,656 Sq Ft

  2140 Brandon Mountain Rd, Rochester, VT 05767

  Tucked away on a picturesque 3-acre lot, this classic three-bedroom expanded Cape offers privacy, seclusion, and peaceful views in a beautiful Rochester valley setting. Set nearly 700 feet back from the road and bordering the Green Mountain National Forest, the property enjoys a tranquil natural backdrop where a scenic pond at the edge of the land attracts birds and wildlife. The main level

  Kyle Kershner Killington Pico Realty

  2140 Brandon Mountain Rd, Rochester, VT 05767
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  /11

  $190,000

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  99 Safford Commons Way, Woodstock, VT 05091

  These 1200 sq. ft., 2-bedroom, 1.5-bathroom condos are being sold for less than half of their fair market value! Available for immediate move-in, each condo has an open-concept kitchen, dining room, and living room, which are on the airy and light-filled second floor. There is a small deck off the living room. The two cozy bedrooms are on the first floor. Electricity bills will be offset by solar

  Jane Darrach Martha E. Diebold/Hanover

  99 Safford Commons Way, Woodstock, VT 05091
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  /34

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft

  6852 Us Route 4, Bridgewater, VT 05034

  This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

  Laird Bradley Williamson Group Sothebys Intl. Realty

  6852 Us Route 4, Bridgewater, VT 05034
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  /59

  $1,450,000

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

  144 Lodge Rd Unit 1, Ludlow, VT 05149

  Experience the ultimate in ski-on/ski-off living with this exceptional 3-bedroom, 3-bathroom slopeside condominium on Okemo Mountain, located in the sought-after SouthFace Village. Park with ease in your assigned covered space beneath the building, complete with a private storage closet for all your mountain gear. From there, take the elevator or walk up the stairs to this first-floor residence,

  Joseph Karl William Raveis Real Estate Vermont Properties

  144 Lodge Rd Unit 1, Ludlow, VT 05149
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  /8

  $125,000

  • Land
  • 7.5 Acres
  • $16,667 per Acre

  00 Howe Hill Rd, Sharon, VT 05065

  Vermont Retreat Awaits. A 7.5 acre wooded parcel with spectacular mountain view potential and five bedroom state waste water permit is ready for your vision. Located off town-maintained Howe Hill Road in Sharon, Vermont, via right of way from lower parcel. Convenient access to power and ultra-high speed fiber optic (EC Fiber) internet at the street, just one mile from I-89. Enjoy easy access to

  Joanne Kent Four Seasons Sotheby's Int'l Realty

  00 Howe Hill Rd, Sharon, VT 05065
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  /15

  $329,000

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

  40 Union St, White River Junction, VT 05001

  Good Cash Flow! Possibilty of Commercial business aspect exists with this property as its in the CB zone / Central Business district. This fully leased two unit property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an onsite owner to occupy one unit and let the extra additional rent help pay for your housing. A fairly low maintenance

  Alex DeFelice The Clerkin Agency, P.C.

  40 Union St, White River Junction, VT 05001
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  /20

  $250,000

  • Land
  • 28.5 Acres
  • $8,772 per Acre

  00 Chapel Hill Rd, Sharon, VT 05065

  Located on a class IV road, right after the end of the publicly maintained section of Chapel Hill Road, this 28.5 acre parcel has potential for a camp, off-grid home, or as a recreational getaway. Extensive work has been done to the road leading to the lot including widening the road and adding culverts and the Seller has roughed in a driveway to a level spot about 600 feet from the town

  Tami Sullivan Snyder Donegan Real Estate Group

  00 Chapel Hill Rd, Sharon, VT 05065
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  /43

  $279,000

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

  436 Mount View Loop, Rochester, VT 05767

  Located on the back side of Mt View Loop is this comfy home, furnished and ready to move right in. Very open concept living space on top floor with woodstove and large dining room set up to enjoy gatherings of any size. Lower floor bedrooms and full bath. Community swim or fishing pond is a deeded right with garden space available and cross country skiing terrain. North Hollow is a desirable area

  Patricia Harvey Xsell Realty LLC

  436 Mount View Loop, Rochester, VT 05767
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  /41

  $399,000

  • 5 Beds
  • 3.5 Baths
  • 2,200 Sq Ft

  109 Park Row, Rochester, VT 05767

  The Richard Steele Hubbard home, ideally situated just off the park in the charming village of Rochester, Vermont, is a fine example of the American Foursquare style popular in the late 19th and early 20th centuries. This five-bedroom residence retains many period details, including handcrafted woodwork, hardwood floors, coffered ceilings, stamped tin, and decorative moldings. Thoughtful updates

  Kyle Kershner Killington Pico Realty

  109 Park Row, Rochester, VT 05767
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  /24

  $675,000

  • Land
  • 41.9 Acres
  • $16,110 per Acre

  8 Grout Rd, Hartland, VT 05048

  Rare, one-of-a-kind land offering with close proximity to Quechee and Hartland.Beautiful building site with Western exposure and exceptional views to the West and North. Pastureland and open meadows for any farming and cultivation needs. Easy construction for additional out buildings or subdivision is possible.Road frontage on Grout Road and the Quechee Hartland road.Private, with

  Charles Bacon Quechee Lakes Real Estate Center

  8 Grout Rd, Hartland, VT 05048
• 

  

  /13

  $489,000

  • 8 Beds
  • 4 Baths
  • 3,483 Sq Ft

  13 Hawthorn St, Hartford, VT 05001

  Strong Cash Flow! Profitable Investment Opportunity! This four unit multifamily property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an on site owner occupancy and the extra rents to pay for your housing.Located in charming Wilder village on a generous .25 +/- acre in town lot. The units consist of three bedroom, two bedrooms and a

  Alex DeFelice The Clerkin Agency, P.C.

  13 Hawthorn St, Hartford, VT 05001
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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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  /11

  $150,000

  • Land
  • 1.79 Acres
  • $83,799 per Acre

  83 Coaching Ln, West Windsor, VT 05037

  Shovel ready project in Brownsville Vt.Fully permitted and ready to go for a timber-frame plan up to 5 bedrooms. 1.79 acre vacant lot only for asking price, or built to suit option. Proven aquifer for high production well. Gorgeous views of Mt. Ascutney, minutes to the ski mountain and outdoor recreation center. The area is known for kind welcoming people and local farms. The Ascutney outdoor

  Jason Saphire www.HomeZu.com

  83 Coaching Ln, West Windsor, VT 05037
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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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  /11

  $2,200,000

  • Land
  • 153.73 Acres
  • $14,311 per Acre

  0 Vermont 106, Reading, VT 05062

  Tucked away near the sought-after communities of Woodstock, West Windsor, and Ludlow, this untouched parcel invites endless possibilities. From its elevated perch, it offers sweeping views of Mt. Ascutney and the Connecticut River Valley in every direction. The Northern New England forested landscape is crisscrossed with trails, old roads, and natural springs, perfect for exploration. There are

  Laird Bradley Williamson Group Sothebys Intl. Realty

  0 Vermont 106, Reading, VT 05062
• 

  /2

  $149,999

  • Land
  • 56.5 Acres
  • $2,655 per Acre

  00 Blackmer Blvd, Stockbridge, VT 05772

  An affordable 56.5 acres of desirable woodland! Pathways heading towards elevated destinations meander up through this tranquil hillside of trees. While some marketable timber has been identified, for many people these classic Vermont woods could be the setting for the construction of a rustic cabin. The property has been "perc tested" by the owners and it has been determined that the property

  John Wetmore Wetmore Real Estate

  00 Blackmer Blvd, Stockbridge, VT 05772
• 

  

  /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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  /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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  /58

  $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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  /28

  $4,500,000

  • Land
  • 127 Acres
  • $35,433 per Acre

  85 Pallottas Hill Rd, Ludlow, VT 05149

  MAJOR 7 FIGURE PRICE REDUCTION! Live, Build, Develop - 127 Acres at Okemo's Doorstep. ~Prime Development Opportunity at the Base of Okemo Mountain. A rare and highly developable 127-acre parcel located just 2 minutes from downtown Ludlow at the foot of world-renowned Okemo Mountain. ~Preliminary engineering, structural work and surveys are complete making this a premier opportunity for a luxury

  Frank Provance Diamond Realty

  85 Pallottas Hill Rd, Ludlow, VT 05149
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  /2

  $221,000

  • Land
  • 8.52 Acres
  • $25,939 per Acre

  0 Barrister Dr Unit 3, Hartford, VT 05001

  In-town building lot opportunity! Don't miss this chance to build your single family home or possibly a multifamily project in the Barrister Drive area of Wider, VT. A nice 8.52 +/- acre in-town lot located at the end of Palmer Court or Barrister Drive. This property is adjacent to an additional 25 +/- acre Norwich, VT. lot that is also for sale at $159,000. and could possibly be used for an

  Alex DeFelice The Clerkin Agency, P.C.

  0 Barrister Dr Unit 3, Hartford, VT 05001
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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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  /15

  $85,000

  • Land
  • 4.05 Acres
  • $20,988 per Acre

  00 Hillcrest Dr, Andover, VT 05143

  Ready to Build in Southern Vermont! Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for remote work

  Daire Gibney Barrett and Valley Associates Inc.

  00 Hillcrest Dr, Andover, VT 05143
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  /11

  $779,000

  • Land
  • 6.46 Acres
  • $120,588 per Acre

  0 Barnard Rd Unit 20.002, Woodstock, VT 05091

  A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

  John Wetmore Wetmore Real Estate

  0 Barnard Rd Unit 20.002, Woodstock, VT 05091
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  /41

  $999,500

  • 3,218 Sq Ft

  1 Depot St, Hartford, VT 05001

  Excellent Upper Valley investment opportunity! This well-maintained six-unit multifamily property features a desirable mix of 3 one-bedroom apartments and 3 two-bedroom apartments, ideally situated in the heart of Wilder. The property sits directly across from the bus stop and offers convenient access to major employers and amenities — just 9 minutes (4.2 miles) from Dartmouth College and 17

  Loren Wehmeyer Tesla Realty Group, LLC

  1 Depot St, Hartford, VT 05001
• 

  

  /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
• 

  

  /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
• 

  /2

  $650,000

  • 5 Beds
  • 2 Baths
  • 2,947 Sq Ft

  108 Main St, Ludlow, VT 05149

  Wonderful investment opportunity in the Ludlow village. 2 unit multi-family with great rental history. Units are in excellent shape. First floor features a spacious 3 bedroom with hardwood floors. The second unit has 2 bedrooms also with Hardwood floors, both in move in ready condition. Units are currently rented and producing income. Just a mile from the Okemo access road and right in the

  Gary Coger Four Seasons Sotheby's Int'l Realty

  108 Main St, Ludlow, VT 05149
• 

  

  /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
• 

  

  /10

  $450,000

  • Land
  • 69 Acres
  • $6,522 per Acre

  00 Vermont 12, Barnard, VT 05031

  A 69 acre mountaintop building lot with dramatic views of distant mountains in an area of Barnard populated with estate properties. The road is in to a potential building site at the height of the land. Soil testing for septic will be completed as soon as snow clears. Subdivision pending. This parcel is currently comprised of two parcels, one being 40+/- acres and the second being 29+/- which can

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Vermont 12, Barnard, VT 05031

Showing Results 81 - 120, Page 3 of 10