Windsor County VT Homes for Sale

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  /14

  $74,000

  • Land
  • 15.5 Acres
  • $4,774 per Acre

  00 Remington Rd, Chester, VT 05143

  Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  00 Remington Rd, Chester, VT 05143
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  /39

  $435,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  22 Birchwood Dr, Perkinsville, VT 05151

  Tucked away at the end of a quiet cul-de-sac, this charming 3-bedroom, 2-bathroom log home offers the perfect blend of privacy, comfort, and convenience. Set on 3.88 acres, this property provides a peaceful retreat with easy access to everyday essentials. Step inside to find warm wood tones, spacious living areas, and classic log home character throughout. The open-concept layout is ideal for

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  22 Birchwood Dr, Perkinsville, VT 05151
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  /42

  $399,800

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056

  Perched at 1,600 feet elevation between Okemo and Killington, this beautifully furnished 3-bedroom, 2-bath condo at Hawk Resort offers the perfect mountain escape--complete with everything you need to move right in.Step into an open-concept living and dining area that flows onto a private deck through glass sliders--perfect for enjoying the sunsets. The living room features soaring cathedral

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056
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  /49

  $749,000

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  37 South St, Woodstock, VT 05091

  Holiday price reduction! Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  37 South St, Woodstock, VT 05091
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  /27

  $369,000

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

  447 Elm St, Chester, VT 05143

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

  Lisa Kelley Cummings & Co

  447 Elm St, Chester, VT 05143
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  /17

  $149,000

  • Land
  • 1.83 Acres
  • $81,421 per Acre

  00 Raymond Rd, Ludlow, VT 05149

  LAND PARCEL WITH LAKE RESCUE ACCESS....This parcel is the last undeveloped lot available that has lake access, shared with a small association, SUNNY VALLEY, with only (8) properties. The building envelope is level and power is at the road. The lot overlooks a pretty meadow with undeveloped woodlands as a backdrop. The Sunny Valley privileges at Lake Rescue include (2) deck platforms overlooking

  Roger Danyew Diamond Realty

  00 Raymond Rd, Ludlow, VT 05149
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  /43

  $595,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  1514 South Rd, Woodstock, VT 05091

  This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car

  Danny Kogut Williamson Group Sothebys Intl. Realty

  1514 South Rd, Woodstock, VT 05091
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  /2

  $210,000

  • 3,950 Sq Ft

  454 Giddings St, Springfield, VT 05150

  GREAT LOCATION ON THIS 3 FAMILY HOME IDEAL FOR A LIVE IN SITUATION OR AS AN INVESTMENT PROPERTY. PRESENT RENT IS BELOW MARKET AND OFFERS GOOD UPSIDE.

  Don Chabot Town and Country Realty

  454 Giddings St, Springfield, VT 05150
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  /5

  $215,000

  • 2,381 Sq Ft

  3 Olney Rd, North Springfield, VT 05150

  FULLY LEASED BUILDING WITH 4 1 BR APARTMENTS JUST 5 MINUTES AWAY FROM SPRINGFIELD INDUSTRIAL PARK. GOOD UPSIDE WITH BELOW MARKET RENTS.

  Don Chabot Town and Country Realty

  3 Olney Rd, North Springfield, VT 05150
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  /43

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 2,970 Sq Ft

  1877 Willard Rd, Hartford, VT 05047

  Stunning Deck House perfectly designed for light, views, and easy Vermont living. Soaring floor-to-ceiling glass in the entryway and stairwell connects all levels and creates a warm, treehouse-like feel, drenched in natural light. Honey-colored hardwood floors warm the main level, while wall-to-wall carpet and tile finish the rest of the spaces. The main level also features a striking stone

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  1877 Willard Rd, Hartford, VT 05047
• 

  

  /11

  $1,350,000

  • 4 Beds
  • 3 Baths
  • 2,277 Sq Ft

  4074 Tichenor Rd Unit 4074, Hartford, VT 05059

  To be built, Mountain Stream at Quechee Lakes seamlessly integrates new construction with the natural beauty of Vermont's premier four-season resort community. Offering over 200 homesites and five distinct home styles, Mountain Stream’s residences feature modern, open layouts, abundant natural light, and soaring ceilings. The exclusive designs establish a commitment to sustainable,

  Richard Higgerson Higgerson & Company

  4074 Tichenor Rd Unit 4074, Hartford, VT 05059
• 

  

  /13

  $1,675,000 New Construction

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

  4071 Tichnor Rd Unit 4071, Hartford, VT 05001

  To be built, Mountain Stream at Quechee Lakes seamlessly integrates new construction with the natural beauty of Vermont's premier four-season resort community. Offering over 200 homesites and five distinct home styles, Mountain Stream’s residences feature modern, open layouts, abundant natural light, and soaring ceilings. The exclusive designs establish a commitment to sustainable,

  Richard Higgerson Higgerson & Company

  4071 Tichnor Rd Unit 4071, Hartford, VT 05001
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  /12

  $1,525,500

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

  5677 Hendee Way Unit 5677, Hartford, VT 05001

  New Construction in Quechee! Introducing Mountain Stream at Quechee Lakes, where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  5677 Hendee Way Unit 5677, Hartford, VT 05001
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  /10

  $1,199,000

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  289 Taft Family Rd Unit 7118, Hartford, VT 05059

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  289 Taft Family Rd Unit 7118, Hartford, VT 05059
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  /12

  $1,495,000

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

  4070 Tichnor Rd Unit 4070, Hartford, VT 05001

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  4070 Tichnor Rd Unit 4070, Hartford, VT 05001
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  /10

  $1,625,000

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

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001
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  /33

  $399,000

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

  158 MacIntosh Hill Rd, Randolph, VT 05060

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

  Sherri McPhetres Vermont Heritage Real Estate

  158 MacIntosh Hill Rd, Randolph, VT 05060
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  /52

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,177 Sq Ft

  166 Woods Rd W, Ludlow, VT 05149

  Perched high on the hillside, this home offers expansive views of the lakes and mountains. Located at the end of a quiet road in the Farm Ridge Community just under 5 miles from the base of Okemo Mountain and 4 miles to Plymouth State Park for boating and swimming in the warmer months. The maintained trails on it's 16.15 acres makes it easy to explore, while the deck is a perfect place to relax,

  Jessica Citera Cummings & Co

  166 Woods Rd W, Ludlow, VT 05149
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  /40

  $685,000

  • 3 Beds
  • 3 Baths
  • 3,589 Sq Ft

  152 Parkview Rd, Springfield, VT 05156

  This beautiful Cape offers a wonderful blend of seclusion and privacy with distant mountain views, to include Okemo Mountain 30 minutes away. The property includes 31.72 acres of lovely meadowlands, woods and a private pond. The woods have several walking paths perfect for casual summer strolls and Winter fun for cross-country skiing and snow-shoeing and close to the VAST network of snowmobile

  Gale Alger Alger Real Estate Agency

  152 Parkview Rd, Springfield, VT 05156
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  /36

  $129,000

  • 1 Bed
  • 1 Bath
  • 240 Sq Ft

  505 Back Mountain Rd Unit 14, Windsor, VT 05089

  This beautifully crafted 2024 “Incredible Tiny Home,” built by Amish artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort.Step outside to enjoy the well-built

  Jenna Luce RE/MAX Upper Valley

  505 Back Mountain Rd Unit 14, Windsor, VT 05089
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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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  /21

  $110,000

  • Land
  • 1.13 Acres
  • $97,345 per Acre

  00 Evergreen Acres, Ludlow, VT 05149

  Located just 3.5 miles from Okemo Mountain, this prime parcel offers endless potential for your dream home. With selective clearing, enjoy breathtaking views of Okemo Mountain. The property comes with an existing Vermont Wastewater permit for a 3-bedroom residence, making it ready for your plans. Whether you're looking to build your perfect retreat or a year-round residence, this location is

  Kevin Barnes William Raveis Real Estate Vermont Properties

  00 Evergreen Acres, Ludlow, VT 05149
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  /32

  $279,000

  • Land
  • 10.2 Acres
  • $27,353 per Acre

  00 Parker Ln, Weston, VT 05161

  Great 10.2 Acre Building Lot with state approved 5 bedroom septic! Ready to bring your vision to life - this property has already had the hard work done for you and features a large 4 acre newly created meadow with spring fed pond. Architectural renderings of a potential home design are available to help you imagine the possibilities. With southern exposure, views of the Green Mountains, and

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  00 Parker Ln, Weston, VT 05161
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  /12

  $245,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  891 Vermont Route 100, Weston, VT 05161

  Charming and efficient, this 2-bedroom, 1-bath home offers a cozy retreat in the heart of Weston, Vermont. Designed for single-level living and low maintenance, the layout makes the most of its space. The main living area features an open flow between the living room and eat-in kitchen, leading to a deck that is perfect for morning coffee or outdoor grilling. Two bedrooms and a full bath complete

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  891 Vermont Route 100, Weston, VT 05161
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  /43

  $299,000

  • 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

  Patricia Harvey Xsell Realty LLC

  436 Mount View Loop, Rochester, VT 05767
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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
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  /35

  $394,000

  • 3 Beds
  • 2.5 Baths
  • 1,918 Sq Ft

  60 Fletcher Ln, Hartford, VT 05001

  Why go on vacation when you can live the lifestyle every day?Updated Quechee Lakes home is just a quick 7-minute ride to the clubhouse, with year-round resort living right at your doorstep.Step inside to a new kitchen outfitted with Wolf appliances, an updated above code wiring, complemented by tile and wood flooring, and a partially replaced roof for peace of mind. With a newer on-demand

  Gerry Stark RE/MAX Upper Valley

  60 Fletcher Ln, Hartford, VT 05001
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  /55

  $949,000

  • 5 Beds
  • 3 Baths
  • 2,807 Sq Ft

  157 Dartt Hill Rd, Bethel, VT 05032

  Nestled on 102 acres in Bethel, Vermont, this property offers the perfect blend of privacy, natural beauty, and functionality. Rolling pastures, wooded trails, and breathtaking Green Mountain views create a serene backdrop for everyday living or a weekend retreat. The land is well-suited for equestrian or hobby farming pursuits, featuring multiple open fields, a four-stall run-in barn, and a

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  157 Dartt Hill Rd, Bethel, VT 05032
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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
• 

  

  /8

  $247,000

  • 5 Beds
  • 3 Baths
  • 3,100 Sq Ft

  99 Depot St, Hartford, VT 05001

  Prime investment opportunity in Wilder, one of Hartford’s five thriving villages. This early-1900s multifamily, minutes from Upper Valley amenities, is ready for redevelopment with significant upside potential.The property features three units offering multiple strategies: renovate and lease all for strong cash flow, or occupy one while offsetting costs with rental income. Its location

  Ralph Harvey Listwithfreedom.com

  99 Depot St, Hartford, VT 05001
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  /21

  $145,000

  • Land
  • 22.23 Acres
  • $6,523 per Acre

  918 Lovers Lane Rd, Chester, VT 05143

  Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State

  Alan Gombosi Northland Real Estate

  918 Lovers Lane Rd, Chester, VT 05143
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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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  /22

  $290,000

  • Land
  • 75 Acres
  • $3,867 per Acre

  1175 Quarry Rd, Chester, VT 05143

  An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

  Jessica Samples BHG Masiello Keene

  1175 Quarry Rd, Chester, VT 05143
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  /60

  $210,000

  • 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. 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 Spring House, which offers an

  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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  /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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  /38

  $139,900

  • 2 Beds
  • 3 Baths
  • 1,190 Sq Ft

  225/227 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn 225/227; Quarter II: Great Location with Deck off the living area with spectacular views of Jackson Gore slopes, overlooking the fire pit and courtyard! Two bedroom lockout design with plenty of room sleeping 10. Cozy and Comfortable open concept living, dining and kitchen. The lockout gives you flexibility for renting and privacy. Convenient elevator access to the pool, daycare

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

  225/227 Qtr I Jackson Gore Inn, Ludlow, VT 05149
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  /60

  $1,425,000

  • 4 Beds
  • 3.5 Baths
  • 4,204 Sq Ft

  411 Wood Rd, Hartford, VT 05001

  Set On 35 acres, This hilltop contemporary captures sweeping long-range views of the Quechee Valley, the Woodstock hills, and the Quechee Ski Hill. With over 4,000 sq. ft. of finely crafted living space, the home showcases quality throughout - custom trim, warm wood and tile floors, radiant heat, and walls of glass designed to frame Vermont’s beauty from nearly every room. The main level is ideal

  Sandy Reavill Real Broker LLC

  411 Wood Rd, Hartford, VT 05001
• 

  

  /38

  $1,995,000

  • 4 Beds
  • 5 Baths
  • 3,500 Sq Ft

  2391 Music Mountain Rd, Stockbridge, VT 05772

  TIMBERS IN THE SKY – Featured in Log and Timber Home Living magazine, this one-of-a-kind Vermont timber frame retreat, built in 2022, blends dramatic architecture with refined comfort. Fully furnished with luxury pieces, the open floor plan showcases a soaring great room with vaulted ceilings, walls of glass framing breathtaking mountain views, exposed beams, and a striking tile gas fireplace.

  Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

  2391 Music Mountain Rd, Stockbridge, VT 05772
• 

  

  /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
• 

  

  /5

  $75,000

  • Land
  • 0.5 Acre
  • $150,000 per Acre

  1015 Maple St, White River Junction, VT 05001

  Nice IN-town building lot! Don't miss this opportunity to build a home, business or garage / storage space along Route 14 / Maple Street. Situated just above the White River and Watson Park in Hartford village! This .50+/- acre in town lot has town water, sewer and power available at the street. Just minutes to I 89 & I 91, Dartmouth College, Dartmouth Hitchcock Medical Center, the VA Hospital,

  Alex DeFelice The Clerkin Agency, P.C.

  1015 Maple St, White River Junction, VT 05001

Showing Results 201 - 240, Page 6 of 11