Windsor County VT Houses for Sale

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  /27

  $249,000 Open Sat 1PM - 3PM

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  106 Hall Rd, Chester, VT 05143

  Open House Saturday, September 20, 1:00 - 3:00 Welcome to your Vermont retreat, an inviting one bedroom, one bath home sat on 2.5 acres at the end of a dead end road in Chester. This 528 square-foot cottage has been thoughtfully updated for four season, comfort, featuring full insulation, a woodstove for cozy evenings, and efficient mini-splits providing both heating and air-conditioning. Recent

  Sandy Reavill Real Broker LLC

  106 Hall Rd, Chester, VT 05143
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  /43

  $349,000

  • 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
• 

  

  

  /34

  $399,000

  • 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?This beautifully updated Quechee Lakes home is just a quick 7-minute ride to the clubhouse, offering year-round resort living right at your doorstep.Step inside to a stunning new kitchen outfitted with Wolf appliances, 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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  /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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  /58

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,146 Sq Ft

  615 Old County Rd, Cavendish, VT 05142

  In need of the perfect ski cabin just 15 minutes from Okemo Mountain? Set on over ten private acres, this home offers the perfect mix of comfort and country charm. The main living room features cathedral ceilings, a propane stove, and access to the deck with a hot tub—ideal for relaxing after a day on the slopes. The kitchen, finished with Vermont soapstone counters and updated appliances, opens

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  615 Old County Rd, Cavendish, VT 05142
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  /46

  $1,595,000

  • 7 Beds
  • 6 Baths
  • 5,774 Sq Ft

  310 Pierce Hill Rd, West Windsor, VT 05089

  Unique Two-Home Property with Stunning Mountain Views.Discover this exceptional property featuring two connected homes, seamlessly blending contemporary design with functionality. Originally built in 1975 and expanded in 2000, this unique residence offers a total of 7 bedrooms, perfect for multi-generational living or as a rental opportunity.The newer side of the home showcases beautiful

  Gary Coger Four Seasons Sotheby's Int'l Realty

  310 Pierce Hill Rd, West Windsor, VT 05089
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  /33

  $149,000

  • 1 Bed
  • 1 Bath
  • 192 Sq Ft

  1150 Tarbell Hill Rd, Cavendish, VT 05142

  Have you been waiting for your own piece of Vermont? Something affordable and easy to maintain? Whether you are looking for a getaway for skiing, relaxing, or a cozy place to call home, this tiny home might be just what you need. This Jamaica Cottage Shop timber frame camp is awaiting new owners to put their own touches on this tiny home. The current owner would be happy to explain all about the

  Tyleen Murray Kelley Real Estate, Inc.

  1150 Tarbell Hill Rd, Cavendish, VT 05142
• 

  

  /22

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  226 N Main St, Bethel, VT 05032

  This 3-bedroom, 1-bathroom home sits on a manageable .10-acre lot and offers the charm of a classic craftsman style. With upgraded electrical and a new water heater, the home is move-in ready while still leaving room for your finishing touches. It needs a little TLC, but the major systems are already in place. Conveniently located close to shopping, dining, and everyday amenities, a great

  Evan Russell Real Broker LLC

  226 N Main 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

  Story Jenks LandVest, Inc/Woodstock

  198 Piper Hill Rd, Weston, VT 05161
• 

  

  /41

  $425,000

  • 4 Beds
  • 1.5 Baths
  • 2,562 Sq Ft

  26 Main St, Chester, VT 05143

  Historically known as the Frank Harris House, this distinguished circa 1880 Queen Anne style Victorian commercial building on .75+/- acres has long been a landmark presence in the village of Chester. With its welcoming veranda and timeless charm, the property has served as a thriving office for many years and has many period architectural details throughout such as, a unique, colored transom

  Geralyn Donohue Engel & Völkers Okemo

  26 Main St, Chester, VT 05143
• 

  

  /19

  $399,900

  • 1 Bed
  • 1 Bath
  • 425 Sq Ft

  1441 Jerusalem Hill, Rochester, VT 05767

  Escape to Serenity: Your Off-Grid Vermont Retreat Awaits...Discover 36.9 acres of pure Vermont bliss at 1441 Jerusalem Hill Rd, Rochester. This unique property offers the ultimate off-grid lifestyle, blending rustic charm with endless possibilities.Imagine waking up in a cozy 1-bed/1-bath cabin (approx. 425 sq ft), nestled amidst nature's embrace. This property offers the potential

  Renae Bouchard KW Vermont

  1441 Jerusalem Hill, Rochester, VT 05767
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  /58

  $550,000

  • 3 Beds
  • 1.5 Baths
  • 1,755 Sq Ft

  2295 Quechee Main St, Hartford, VT 05047

  Charming New Englander in the Heart of Quechee! Owned by the same family for more than 30 years, this classic New Englander is set on a spacious double lot in Quechee’s Historic Mill District. The home offers practical living spaces inside, while outside you’ll find ample room for gardening, play, or simply relaxing by the shade trees and small water feature.Being sold “As Is,” this is a

  Jill Harlow Coldwell Banker LIFESTYLES - Hanover

  2295 Quechee Main St, Hartford, VT 05047
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  /34

  $459,000 Open House 10/11

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft

  40 Middle Rd, Weston, VT 05161

  *MOTIVATED SELLERS* Down a quiet country road, where pavement yields to gravel and the air carries the scent of pine and possibility, this 3-bedroom, 3-bathroom home is nestled into 2.8 acres of Vermont woodland. Private and peaceful, yet just a short drive to both Weston Village and Londonderry Village, with ski resorts close enough for spontaneous powder days, yet far enough to keep the traffic

  Rachel Febbie EXP Realty

  40 Middle Rd, Weston, VT 05161
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  /25

  $207,000

  • 3 Beds
  • 3 Baths
  • 1,604 Sq Ft

  295 Hotel Rd Unit 10/10A, Brownsville, VT 05037

  This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the tubing hill and take in all the action just outside your door!This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including

  Allison Griep KW Vermont Woodstock

  295 Hotel Rd Unit 10/10A, Brownsville, VT 05037
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  /21

  $299,500

  • 3 Beds
  • 1.5 Baths
  • 1,716 Sq Ft

  306 Camp Brook Rd, Bethel, VT 05032

  $3,000 TOWARDS CLOSING COSTS. MOTIVATED SELLER! Welcome to 306 Camp Brook Road, a charming Vermont home nestled on 1.1 peaceful acres in Bethel. This inviting 3-bedroom, 1.5-bath residence offers a perfect blend of classic New England warmth and comfortable living.Step inside to discover beautiful wide-plank wood floors, an airy open-concept living and dining area, and a cozy wood

  Nathan Wright Century 21 The One

  306 Camp Brook Rd, Bethel, VT 05032
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  /28

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  25 Felton Rd, Weston, VT 05161

  Beautiful Weston! Just 2 miles from the town center, this 3 Bedroom, 2 Bath Ranch style home on 1.5 Acres offers easy access, just off Route 100, with single level living. Enter into a large Sunroom surrounded with windows, giving the feeling of being outdoors year round and enjoy the wonderful Pellet stove. The eat-in Kitchen, with granite counter tops, offers plenty of cabinet space. The

  Brian Gehlich RE/MAX Four Seasons

  25 Felton Rd, Weston, VT 05161
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  /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
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  /60

  $1,395,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 3.5 Baths
  • 3,590 Sq Ft

  332 Cushing Rd, Hartford, VT 05001

  Perched at 1,700 feet on 40 private acres, this Vermont retreat captures sweeping views across the Connecticut River Valley to New Hampshire’s Presidential Range. Despite its sense of seclusion, it’s only minutes to Quechee Village, Woodstock, and Dartmouth College in Hanover.Part of a 10-home association, the property includes access to 52 acres of meadows, woodlands, and a spring-fed

  Keri Cole Williamson Group Sothebys Intl. Realty

  332 Cushing Rd, Hartford, VT 05001
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  /60

  $2,499,000

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

  254 Town Line Rd Unit 14 and 16, 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 Unit 14 and 16, Plymouth, VT 05056
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  /40

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 3,089 Sq Ft

  16 Church St, Woodstock, VT 05091

  16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village,

  John Snyder Snyder Donegan Real Estate Group

  16 Church St, Woodstock, VT 05091
• 

  

  /31

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 3,466 Sq Ft

  649 Spencer Hollow Rd, Springfield, VT 05156

  Welcome to your dream retreat! Nestled on 10.10 sprawling acres of peaceful countryside, this beautifully maintained 3-bedroom, 3-bathroom single-family home offers the perfect blend of privacy, charm, and modern comfort. Step inside to discover vaulted ceilings that enhance the spacious, open-concept living area, complemented by warm natural light and serene views. The loft space, ideal as a

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  649 Spencer Hollow Rd, Springfield, VT 05156
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  /51

  $1,475,000

  • 5 Beds
  • 4.5 Baths
  • 3,060 Sq Ft

  593 Red Barn Rd, White River Junction, VT 05001

  A rare opportunity! This private, tranquil 6.7 AC farm is just a short stroll to the Quechee Club and all amenities. Built in 1975 to the highest standard, and sited to take advantage of a lovely valley view overlooking pastures, rolling fields and your very own spring fed swimming pond. The home is beautifully composed with bright open spaces flowing seamlessly for entertaining and everyday

  Danny Kogut Williamson Group Sothebys Intl. Realty

  593 Red Barn Rd, White River Junction, VT 05001
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  /56

  $564,000

  • 3 Beds
  • 2 Baths
  • 2,123 Sq Ft

  2 Lacava Ln, Ludlow, VT 05149

  This charming renovated farmhouse being sold totally turnkey sits up above the Village of Ludlow on a country lot complete with a peaceful spot to sit by the brook. The current owners have picked up where the prior owners left off with some stylish updates and improvements. The main level of the home will welcome you with beautiful wood floors in the open living area with many spaces to sit and

  Tyleen Murray Kelley Real Estate, Inc.

  2 Lacava Ln, Ludlow, VT 05149
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  /36

  $499,900

  • 3 Beds
  • 1 Bath
  • 1,832 Sq Ft

  3738 Brownsville Hartland Rd, West Windsor, VT 05089

  Welcome to this 3-bedroom, 1-bath farmhouse in the heart of West Windsor, VT! Inside, you’ll find a warm and inviting open-concept layout featuring a main floor bedroom, and mudroom. Perfect for gatherings or quiet evenings.Beyond the farmhouse, the property includes a wonderful collection of outbuildings—a classic barn, a 2-car garage, a workshop with a woodstove, and even a

  Katie Ladue Gilbert KW Vermont Woodstock

  3738 Brownsville Hartland Rd, West Windsor, VT 05089
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  /28

  $585,000

  • 3 Beds
  • 3 Baths
  • 2,568 Sq Ft

  561 Neal Rd, White River Junction, VT 05001

  Beautifully maintained raised ranch set on a private, landscaped 2-acre lot just minutes from the VA hospital and in-town amenities. This home has been thoughtfully updated in 2017 with a new roof, siding, kitchen, baths, fresh paint and more -offering peace of mind and move-in readiness. The light filled interior features stylish finishes and modern comfort, while the outdoor spaces provide

  Susanne Pacilio Martha E. Diebold/Hanover

  561 Neal Rd, White River Junction, VT 05001
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  /35

  $549,000

  • 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.

  Keri Cole Williamson Group Sothebys Intl. Realty

  3364 W Woodstock Rd, Woodstock, VT 05091
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  /43

  $6,100,000

  • 6 Beds
  • 6 Baths
  • 8,264 Sq Ft

  37 Maxham Rd, Woodstock, VT 05091

  Hawk Gate Farm is a 352-acre estate, roughly square in shape, in the hills of South Pomfret. This storied landscape—once five independent farmsteads—embodies the evolution of rural New England from its earliest post-colonial roots to the present day. At its heart stands the Isaac Newton House, a c.1790 Federal-style brick Cape with preserved period detail. Features include finely crafted

  Story Jenks LandVest, Inc/Woodstock

  37 Maxham Rd, Woodstock, VT 05091
• 

  

  /23

  $269,000 Open Sat 10AM - 12PM

  • 2 Beds
  • 1 Bath
  • 1,336 Sq Ft

  6 Blodgett Ln, Hartland, VT 05048

  Come and fall in love with this charming home filled with character, right in town close to local stores, schools and town hall with a great community feel and easy access to the highway. Both bedrooms are on the first floor. Open Kitchen to dining and living room, with a cozy front porch perfect for lying in the hammock or enjoying a coffee. There are raspberries, strawberry's and mint growing

  Ara Cardew BHG Masiello Keene

  6 Blodgett Ln, Hartland, VT 05048
• 

  

  /44

  $895,745

  • 2 Beds
  • 2 Baths
  • 1,576 Sq Ft

  1342 Old Stage Rd, Chester, VT 05143

  Welcome to your own private retreat—98 acres of serene Vermont beauty featuring meadows, woods, two ponds, and eight versatile outbuildings. Thoughtfully maintained and tastefully appointed, this charming home is nestled in a park-like setting complete with long, historic rock walls, mature trees, and flourishing perennial gardens. Nature lovers will revel in the abundance of wildlife, from

  Jessica Landers Barrett and Valley Associates Inc.

  1342 Old Stage Rd, Chester, VT 05143
• 

  

  /58

  $1,435,000

  • 4 Beds
  • 2.5 Baths
  • 4,419 Sq Ft

  15 Brigham Hill Rd, Norwich, VT 05055

  This magical property is what Vermont dreams are made of! Located one mile from downtown Norwich, this antique cape has been thoughtfully maintained, renovated into fabulous and unique spaces and sits on 3+ perfect acres. Four bedrooms, included a first floor primary suite, two great offices, an amazing family room for movies nights and a great recreation room for all your games. The main

  Amy Redpath Coldwell Banker LIFESTYLES - Hanover

  15 Brigham Hill Rd, Norwich, VT 05055
• 

  

  /42

  $3,500,000

  • 6 Beds
  • 8 Baths
  • 5,142 Sq Ft

  18 The Green, Woodstock, VT 05091

  Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort

  Danny Kogut Williamson Group Sothebys Intl. Realty

  18 The Green, Woodstock, VT 05091
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  /35

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 1,304 Sq Ft

  231 Richardson Rd, Chester, VT 05143

  This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also

  Thaddeus Abare Barrett and Valley Associates Inc.

  231 Richardson Rd, Chester, VT 05143
• 

  

  /18

  $239,995 Open Sun 9AM - 11AM

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft

  2359 Vermont 107, Bethel, VT 05032

  $5,000 TOWARDS CLOSING COSTS!! Charming 2-Bedroom, 1 - "Office" VT Route 107 Home — High Ceilings, Hardwood Floors, Garage with Office, and Prime LocationJust minutes from Exit 3, this versatile Royalton property blends comfort, convenience, and flexibility—perfect for home living, a small business, or both.Bright, Spacious Living – Soaring high ceilings and beautiful hardwood

  Nathan Wright Century 21 The One

  2359 Vermont 107, Bethel, VT 05032
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  /60

  $399,900

  • 5 Beds
  • 4.5 Baths
  • 6,236 Sq Ft

  2615 North Rd, Bethel, VT 05032

  Million dollar home opportunity for pennies on the dollar! This massive home has been gutted down to the studs and is ready for your finishing touches. This home was previously run as an inn with 6 bedrooms and 5.5 baths. The finished walkout basement is still intact. Vaulted ceilings, multiple decks, and views from almost every room make this house a desirable project. The house is well hidden

  Lisa Friedman Great American Dream Realty

  2615 North Rd, Bethel, VT 05032
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  /28

  $459,000

  • 3 Beds
  • 2 Baths
  • 2,314 Sq Ft

  7265 U S 4, Bridgewater, VT 05034

  This captivating historic cape has been tastefully updated while retaining its unique architectural charm. The spacious floor plan is centered around the lovely eat-in kitchen with its butcher block covered center island all of which is detailed by a striking exposed beamed ceiling. Located off one side of the kitchen is the mudroom entryway with built-ins that introduces you to an inviting

  Mary Mayhew Snyder Donegan Real Estate Group

  7265 U S 4, Bridgewater, VT 05034
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  /60

  $1,499,000

  • 4 Beds
  • 3.5 Baths
  • 3,560 Sq Ft

  652 Tierney Rd, Cavendish, VT 05142

  Tucked discretely off a meandering country road you will find this charming 4 bedroom, 3 and 1/2 bath contemporary home sited on 40 acres of land with miles of groomed trails that include a picnic area on Twenty Mile Stream. The grand living room , anchored by a wood-burning fireplace and lined by a wall of windows , frames views of the giant swimming pond and long range mountain views that

  Carol Wood Williamson Group Sothebys Intl. Realty

  652 Tierney Rd, Cavendish, VT 05142
• 

  

  /34

  $1,295,000

  • 3 Beds
  • 3 Baths
  • 2,764 Sq Ft

  766 Masterson Rd, Bethel, VT 05032

  Tucked at the end of a quiet country road, Sugar Bowl Farm is a modern farmhouse set on 124 private acres. Completed in 2025, the home is beautifully finished and filled with natural light, especially in the cathedral-ceilinged great room where south and east facing windows catch the shifting light throughout the day. This airy central space flows effortlessly to the veranda, deck, and gardens

  Dia Jenks LandVest, Inc/Woodstock

  766 Masterson Rd, Bethel, VT 05032
• 

  

  /58

  $1,400,000

  • 6 Beds
  • 5 Baths
  • 4,571 Sq Ft

  505 Deweys Mills Rd, Hartford, VT 05047

  The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the

  Jennifer Falvey KW Vermont Woodstock

  505 Deweys Mills Rd, Hartford, VT 05047
• 

  

  /44

  $545,000

  • 4 Beds
  • 2.5 Baths
  • 1,674 Sq Ft

  2110 Lynds Hill Rd, Plymouth, VT 05056

  Wonderful location on over 14 acres with outstanding mountain views! Immediate access to VAST snowmobile trails and endless hiking/mountain biking trails. This 4 bedroom, 2 1/2 bath mountain contemporary chalet has an open concept floor plan with loads of glass to soak in the amazing views. Handsome fieldstone hearth with wood burning fireplace on the main living level. The primary bedroom with

  Marni Rieger KW Vermont-Killington

  2110 Lynds Hill Rd, Plymouth, VT 05056
• 

  

  /38

  $435,000

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft

  96 Dairy Ln, Windsor, VT 05089

  Before the leaves have fallen, the PRICE on this one has! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont’s natural beauty while being just minutes from town amenities, schools, and I-91.Inside, you'll find a traditional floor

  Katie Ladue Gilbert KW Vermont Woodstock

  96 Dairy Ln, Windsor, VT 05089

Showing Results 81 - 120, Page 3 of 8