Windsor County VT Houses for Sale

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  /47

  $319,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,782 Sq Ft

  147 South St, Springfield, VT 05156

  Welcome to your own oasis! This lovingly updated, renovated and maintained 4-bedroom, 2-bath home located on a large 1.50 acre lot gives you the convenience of an in-town home and the back yard that looks like your own personal oasis with an above ground pool, landscaped perennial beds, deck with a shade awning, fire pit, fenced for family and pets along with room for a veggie bed beyond the

  

  Julie Buffum

  Buffum Realty

  (802) 521-2366

  147 South St, Springfield, VT 05156
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  /54

  $2,599,000

  • 9 Beds
  • 11 Baths
  • 5,993 Sq Ft

  41 Pleasant St, Woodstock, VT 05091

  This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

  

  Jennifer Falvey

  KW Vermont Woodstock

  (802) 347-9544

  41 Pleasant St, Woodstock, VT 05091
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  /39

  $699,000

  • 4 Beds
  • 3.5 Baths
  • 4,336 Sq Ft

  166 Robbins Hill, Hartford, VT 05059

  This sun-soaked Quechee Lakes home offers the privacy of single-family living with the added benefits of country club amenities. It sits at the end of a quiet road and offers on-site access to wooded walking trails, perfect for hiking or snowshoeing. Walk in through the front door to a warm foyer, which leads directly to the architecturally dramatic sunken living room featuring a stone fireplace

  

  Jennifer Falvey

  KW Vermont Woodstock

  (802) 278-9437

  166 Robbins Hill, Hartford, VT 05059
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  /49

  $319,000

  • 3 Beds
  • 3 Baths
  • 1,932 Sq Ft

  5 Church St, North Springfield, VT 05150

  Nicely maintained 3BR/3BA ranch home just waiting for a new family. This home features large, updated eat-in kitchen with sliders to a deck, main floor laundry, gas fireplace, home office/den, partially finished basement has a 3/4 bath, workshop area, partially finished rooms that could be additional bedrooms and a large partially finished area for family room. Primary bedroom with bath and lots

  

  Julie Buffum

  Buffum Realty

  (802) 520-0294

  5 Church St, North Springfield, VT 05150
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  /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

  (877) 419-4767

  505 Deweys Mills Rd, Hartford, VT 05047
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  /38

  $795,000

  • 4 Beds
  • 3 Baths
  • 2,099 Sq Ft

  6077 Vt Route 12, Barnard, VT 05031

  BARNARD VILLAGE CAPE- This elegant Cape sits in an ideal location in the idyllic village of Barnard, just a short walk to the Barnard General Store and Silver Lake. The perfect blend of original charm, sophistication, and modern amenities, the house is bright and welcoming with lovely natural woodwork and plenty of space for social gatherings or quiet privacy. A large central living room features

  David Donegan Snyder Donegan Real Estate Group

  6077 Vt Route 12, Barnard, VT 05031
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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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  /41

  $849,900

  • 3 Beds
  • 3 Baths
  • 3,392 Sq Ft

  117 Horseshoe Dr, Brownsville, VT 05037

  Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

  Katie Ladue Gilbert KW Vermont Woodstock

  117 Horseshoe Dr, Brownsville, VT 05037
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  /50

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  187 Hopson Rd, Norwich, VT 05055

  This one-of-a-kind spacious home was designed by the architect, George T. Hathorn, and built by G.R. Porter and Sons - both of whom represent an era of home building quality unsurpassed to this day. As befits the climate, the centerpiece of this house is a woodstove, framed by a grand 3-story brick chimney and adjacent staircase – a unique layout that is both beautiful and wonderfully efficient

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  187 Hopson Rd, Norwich, VT 05055
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  /40

  $2,299,000

  • 6 Beds
  • 6 Baths
  • 7,619 Sq Ft

  5518 Vt Route 12, Barnard, VT 05031

  An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All the amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round cultural events

  John Wetmore Wetmore Real Estate

  5518 Vt Route 12, Barnard, VT 05031
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  /46

  $8,000,000

  • 3 Beds
  • 3.5 Baths
  • 6,096 Sq Ft

  115 Eastman Rd, South Woodstock, VT 05071

  Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

  Keri Cole Williamson Group Sotheby's International Realty

  115 Eastman Rd, South Woodstock, VT 05071
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  /55

  $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
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  /46

  $750,000

  • 3 Beds
  • 3 Baths
  • 1,432 Sq Ft

  58 Greenbush Rd, Cavendish, VT 05142

  Charming Cape Cod Home in a Serene Country Setting – 10.10 Acres Welcome to this beautifully transformed Cape Cod-style home, nestled on just over 10 acres of picturesque countryside. Offering a perfect blend of classic charm and modern convenience, this inviting property is ideal for those seeking tranquility and space. Step onto the welcoming front porch, where you can relax and take in the

  Katie Ladue Gilbert KW Vermont Woodstock

  58 Greenbush Rd, Cavendish, VT 05142
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  /32

  $1,865,000

  • 3 Beds
  • 3.5 Baths
  • 3,827 Sq Ft

  2346 Quechee Main St, White River Junction, VT 05001

  A beautifully constructed residence, designed to take in breathtaking views of the river, the Lakeland course of the Quechee club golf course, the Quechee ski slopes, and lake Pinneo. The house offers high-quality details inside and out including porches, stone patios, octagonal viewing/sitting rooms and more. Gourmet kitchen of with a large walk-in pantry, 2 river stone fireplaces, tigerwood

  John Snyder Snyder Donegan Real Estate Group

  2346 Quechee Main St, White River Junction, VT 05001
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  /32

  $1,295,000

  • 2 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  33 Mountain Ave, Woodstock, VT 05091

  Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one

  Mary Mayhew Snyder Donegan Real Estate Group

  33 Mountain Ave, Woodstock, VT 05091
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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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  /41

  $795,000

  • 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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  /42

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  1979 N Hill Rd, Chester, VT 05143

  Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

  Geralyn Donohue Engel & Völkers Okemo

  1979 N Hill Rd, Chester, VT 05143
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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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  /47

  $8,000,000

  • 3 Beds
  • 3.5 Baths
  • 5,384 Sq Ft

  115 Eastman Rd, Woodstock, VT 05091

  Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

  Keri Cole Williamson Group Sothebys Intl. Realty

  115 Eastman Rd, Woodstock, VT 05091
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  /29

  $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 Realty

  29 Markham Ln, Weston, VT 05161
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  /37

  $165,000

  • 3 Beds
  • 1 Bath
  • 1,554 Sq Ft

  89 Route 12, Hartland, VT 05048

  Step into the charm of this antique home, offering an abundance of potential for restoration and customization. Highlights include beautiful wide board floors and a quiet, private backyard set on just under an acre. Ideal for buyers ready to take on a project and bring this special property back to life. Located in the desirable quaint town of Hartland, close to skiing, hiking, and Dartmouth,

  Erika Smith RE/MAX Upper Valley

  89 Route 12, Hartland, VT 05048
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  /43

  $1,600,000

  • 4 Beds
  • 3 Baths
  • 6,014 Sq Ft

  15 Central St, Woodstock, VT 05091

  15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building

  Laird Bradley Williamson Group Sothebys Intl. Realty

  15 Central St, Woodstock, VT 05091
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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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  /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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  /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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  /36

  $845,000

  • 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
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  /46

  $1,325,000

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

  325 Cemetery Rd, West Windsor, VT 05089

  Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide

  Story Jenks LandVest, Inc/Woodstock

  325 Cemetery Rd, West Windsor, VT 05089
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  /35

  $369,000

  • 3 Beds
  • 2 Baths
  • 1,911 Sq Ft

  1846 Dartt Hill Rd, Bethel, VT 05032

  1978 Saltbox on 10 acres of both open and wooded land. The home boasts wide plank floors throughout with 3 bedrooms, 2 baths, open floor plan on the main floor with spacious kitchen. A lovely home, a must see.

  Sherri McPhetres Vermont Heritage Real Estate

  1846 Dartt Hill Rd, Bethel, VT 05032
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  /57

  $817,000

  • 3 Beds
  • 2 Baths
  • 2,760 Sq Ft

  616 Rose Hill Rd, Woodstock, VT 05091

  This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house

  Carol Wood Williamson Group Sothebys Intl. Realty

  616 Rose Hill Rd, Woodstock, VT 05091
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  /44

  $449,000

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

  339 Ranney Rd, Stockbridge, VT 05772

  Take a look at this home in mid-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 options

  Risa Mornis Covered Bridge RE

  339 Ranney Rd, Stockbridge, VT 05772
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  /46

  $499,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 4 Baths
  • 2,258 Sq Ft

  79 Clarina Nichols Ln, Hartford, VT 05001

  Open House 11 am - 1:00 pm on Sunday, January 11, 2026. Nestled in the heart of the Quechee Club community with a seasonal view across the valley, just 7 miles east of Woodstock and Saskadena Six skiing, this spacious four-bedroom, four bathroom home offers the best of Vermont living. Quechee Lakes is a private, full-amenity resort with two championship golf courses, a private lake and beach,

  Sandy Reavill Real Broker LLC

  79 Clarina Nichols Ln, Hartford, VT 05001
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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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  /54

  $765,000

  • 4 Beds
  • 3.5 Baths
  • 2,828 Sq Ft

  119 Pine Hill Rd, Ludlow, VT 05149

  Nestled in the desirable Okemo Pines community, this 4-bedroom, 3.5-bath home offers the perfect blend of comfort, charm, and convenience, only minutes from Okemo Mountain Resort. Thoughtfully designed for year-round enjoyment, the home features multiple seasonal living areas, including a large deck with Okemo views, a sunroom, and a covered porch with mountain views. The house offers privacy

  Joseph Karl William Raveis Real Estate Vermont Properties

  119 Pine Hill Rd, Ludlow, VT 05149
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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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  /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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  /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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  /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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  /45

  $795,000

  • 4 Beds
  • 2.5 Baths
  • 2,663 Sq Ft

  490 W Hill Rd, Ludlow, VT 05149

  From mountain views to après-ski soaks in the hot tub, this home delivers the full Vermont lifestyle with ease. Located on one of Ludlow’s most coveted roads, this custom-built mountain retreat offers the perfect blend of quality, comfort, and convenience. Skip the village traffic and drive straight to the base of Okemo in just minutes! Thoughtfully designed and with so much to love, this

  Frank Provance Diamond Realty

  490 W Hill Rd, Ludlow, VT 05149
• 

  

  /37

  $589,000

  • 3 Beds
  • 1.5 Baths
  • 888 Sq Ft

  19 Strawberry Ln, Ludlow, VT 05149

  Wow! Been waiting for an eye-catcher with a mountain view? Okemo's trails are calling! Presenting something unique, efficient, classy and sleek to check your boxes. Set out in the lakes region close to Summer fun and a quick drive to the Okemo is this new custom-built container home waiting for some lucky peeps to chill on the deck, glisten in the sauna, refresh in the pool, and sled down the

  Tyleen Murray Kelley Real Estate, Inc.

  19 Strawberry Ln, Ludlow, VT 05149

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