Windsor County VT Houses for Sale

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  /60

  $599,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  5100 Route 100, Plymouth, VT 05056

  (Das Grünebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

  Marni Rieger KW Vermont-Killington

  5100 Route 100, Plymouth, VT 05056
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  /42

  $699,900

  • 3 Beds
  • 1.5 Baths
  • 1,938 Sq Ft

  4205 Vermont 131, Weathersfield, VT 05151

  Step into timeless New England charm with this historic circa-1760s expanded Cape, offering a wonderful blend of early craftsmanship, character, and modern-day livability. The home showcases classic timber frame construction with hand hewn beams, beautiful wide plank floors, and preserved period details that create warmth and authenticity throughout every room. With three bedrooms and two full

  Thaddeus Abare Barrett and Valley Associates Inc.

  4205 Vermont 131, Weathersfield, VT 05151
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  /48

  $769,000

  • 4 Beds
  • 3 Baths
  • 3,179 Sq Ft

  31 Plumley Ave, Ludlow, VT 05149

  Charming Country Retreat in Ludlow – Minutes from Okemo MountainDon’t miss this rare opportunity to enjoy the peace of country living in the heart of Ludlow, a quintessential Vermont ski town and home to Okemo Mountain Resort. This meticulously maintained home has been lovingly cared for by the same owner for over 30 years. Designed for easy living, this move-in-ready property features

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  31 Plumley Ave, Ludlow, VT 05149
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  /53

  $595,000

  • 3 Beds
  • 2 Baths
  • 2,966 Sq Ft

  147 Pleasantview Ln, Chester, VT 05143

  Tucked away at the end of a quiet lane on three scenic acres, this well-maintained home offers a rare blend of privacy, versatility, and proximity to town. Set against the backdrop of the Williams River, the property delivers a peaceful setting with year-round interest: mature apple trees, open lawn, and seasonal views best enjoyed from the expansive back deck. Inside, over 2,500 square feet of

  Jay Farrar Four Seasons Sotheby's Int'l Realty

  147 Pleasantview Ln, Chester, VT 05143
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  /17

  $825,000

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

  1928 Vermont 131, Springfield, VT 05156

  COUNTRY LIVING ON 118 ACRES WITH FULLY APPLIANCED, 4 BR's, 1.5 BATH HOME WITH ATTACHED GARAGE WITH 2ND FLOOR, A STATE-OF-THE ART PELLET BOILER, ROOF TOP SOLAR SYSTEM, SMALL POND, BARN AND STORAGE BUILDINGS. THE LAND BOAST ONE OF THE MOST BEAUTIFUL AND PLENTIFUL SUGAR BUSH IN THE STATE THAT EASILY ACCOMADATES OVER 4500 TAPS. SEVERAL WELL-MAINTAINED WOOD-LAND TRAILS TRAVERSE THE ACREAGE AND THE

  Don Chabot Town and Country Realty

  1928 Vermont 131, Springfield, VT 05156
• 

  

  /45

  $675,000

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft

  598 E Woodstock Rd, Woodstock, VT 05091

  Historic Woodstock, Vermont – Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont’s most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local

  Erika Smith Coldwell Banker LIFESTYLES - Hanover

  598 E Woodstock Rd, 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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  /51

  $549,000

  • 5 Beds
  • 3 Baths
  • 2,704 Sq Ft

  37 Robinson Ave, Rochester, VT 05767

  This beautifully updated three-unit property in charming Rochester, VT offers exceptional flexibility for investors or owner-occupants. The mainresidence features three spacious bedrooms, complemented by two private one-bedroom units, each with its own separate entrance. All three units have been nicelyupdated throughout and are well-suited for short or long-term rental, with a strong STR

  Nathan Mastroeni

  37 Robinson Ave, Rochester, VT 05767
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  /29

  $530,000

  • 3 Beds
  • 2.5 Baths
  • 4,020 Sq Ft

  28 Fairview Terrace, Royalton, VT 05068

  This 3-bedroom, 2.5-bath home is full of potential, with the option to create an auxiliary dwelling for added flexibility. The current owner saw the promise in this gem and has already invested in the important updates: fresh exterior paint, a brand-new septic system, a new roof, upgraded electrical, and other quality improvements. With much of the essential work complete, the next owner has the

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  28 Fairview Terrace, Royalton, VT 05068
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  /31

  $299,000

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft

  29 Markham Ln, Weston, VT 05161

  This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

  Catherine Cairns Maple Leaf Realty

  29 Markham Ln, Weston, VT 05161
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  /48

  $2,500,000

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

  5518 Vermont 12, Barnard, VT 05031

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

  Laird Bradley Williamson Group Sothebys Intl. Realty

  5518 Vermont 12, Barnard, VT 05031
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  /58

  $485,000

  • 8 Beds
  • 1 Bath
  • 3,500 Sq Ft

  1254 U S 5, Springfield, VT 05156

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

  Glenn Olney Barrett and Valley Associates Inc.

  1254 U S 5, Springfield, VT 05156
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  /49

  $527,000

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

  88 Happy Valley Rd, Woodstock, VT 05091

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

  Julie Davis KW Vermont Woodstock

  88 Happy Valley Rd, Woodstock, VT 05091
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  /47

  $149,000

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft

  49 Clay Hill Rd, Hartland, VT 05048

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

  Steve Schoppmeyer BHG Masiello Brattleboro

  49 Clay Hill Rd, Hartland, VT 05048
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  /35

  $424,900

  • 1 Bed
  • 1.5 Baths
  • 1,255 Sq Ft

  71 Grouse Ln, Perkinsville, VT 05151

  This beautiful, expanded Cape is set in a quiet, peaceful location and is very well appointed throughout, offering a warm and welcoming place to call home. A charming covered front porch invites you to sit back and relax, while a thoughtfully designed entryway creates an easy and inviting transition into the living space. The interior has been extremely well maintained, blending modern comfort

  Thaddeus Abare Barrett and Valley Associates Inc.

  71 Grouse Ln, Perkinsville, VT 05151
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  /49

  $449,000

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

  339 Ranney Rd, Stockbridge, VT 05772

  EXTRA ACRE! EXTRA VALUE. PROPERTY NOW INCLUDES one more acre than previously listed. Take a look at this home in central Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 3 acre lot with plenty of sun and space for renovations, pets, gardens, greenhouses or farm animals. This Stockbridge home has an in-law apartment below- accessible by a separate driveway.

  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 New Hampshire, the Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The post and beam construction, gunstock corner posts, exposed beams, extraordinarily wide floor boards, 4

  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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  /60

  $420,000

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

  2451 Camp Brook Rd, Bethel, VT 05032

  This charming log home sits nestled off the main road, above the nearby Camp Brook, which meanders through the property. This home was thoughtfully built and lovingly cared for by it's current owner. The open living/dining room is light filled by skylights and sliding glass doors that lead to the back deck. Cozy up by the brick fireplace with stove insert. Sit and listen to the babbling brook on

  Suzi Lamson Vermont Heritage Real Estate

  2451 Camp Brook Rd, Bethel, VT 05032
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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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  /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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  /48

  $589,000

  • 3 Beds
  • 2 Baths
  • 1,908 Sq Ft

  530 West Rd, Barnard, VT 05031

  Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

  Dan Noble Snyder Donegan Real Estate Group

  530 West Rd, Barnard, VT 05031
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  /42

  $4,500,000

  • 4 Beds
  • 2 Baths
  • 3,150 Sq Ft

  85 Pallottas Hill Rd, Ludlow, VT 05149

  MAJOR 7 FIGURE PRICE REDUCTION! Your Vermont Mountain Retreat Awaits Discover 127 acres of pure Vermont beauty at the foot of Okemo Mountain, just 2 minutes from downtown Ludlow. This rare property offers expansive meadows, forested trails, and panoramic views of Okemo, Mount Ascutney and beyond. Enjoy direct access to cross country skiing, hiking, snowshoeing, the VAST trail system, and

  Frank Provance Diamond Realty

  85 Pallottas Hill Rd, Ludlow, VT 05149
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  /20

  $279,900 New Construction

  • 1,308 Sq Ft

  320 W Rowe Hill Rd, West Windsor, VT 05037

  Wonderful unfinished 24'x34' pole building, a rare opportunity to shape a home or getaway that fits your lifestyle perfectly on 9.4 tranquil acres on W Rowe Hill Rd. On VAST trail, great trail location for year round recreation. Close to GMHA & Ascutney Outdoors, ride your horse, bike or sled right from your door! A short drive to Okemo or Killington. Easy access to I91 and the Upper Valley.

  Dana Waters Dark Horse Realty

  320 W Rowe Hill Rd, West Windsor, VT 05037
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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
• 

  

  /19

  $525,000

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  175 Pleasant Valley Rd, Springfield, VT 05156

  Welcome to your own peaceful, private homestead. Set on 7.5 acres of wooded and open land this property is truly a respite from the stresses of the world. This multi-level 3-bedroom, 3 bath home offers convenience and options. The spacious living room with hardwood floors leads to a large eat-in kitchen with ample storage and room for an island if desired. Step into the Family room or a large

  Carol Cole BHG Masiello Brattleboro

  175 Pleasant Valley Rd, Springfield, VT 05156
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  /51

  $390,000

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

  663 Depot St, Chester, VT 05143

  Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates.

  Betsy Adamovich Real Broker LLC

  663 Depot St, Chester, VT 05143
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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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  /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
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  /41

  $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
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  /52

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,800 Sq Ft

  248 Gird Lot Rd, Weathersfield, VT 05151

  Perched above the Connecticut River Valley with sweeping views to the New Hampshire mountains, this meticulously maintained five bedroom, four and a half bath home offers a rare opportunity just 30 minutes to Hanover, NH, Dartmouth College, and Dartmouth Hitchcock Medical Center. For medical professionals relocating to the Upper Valley, this property provides privacy, acreage, and panoramic views

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
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  /60

  $3,100,000

  • 5 Beds
  • 4.5 Baths
  • 7,634 Sq Ft

  165 Moonshadow Dr Unit M-15, Ludlow, VT 05149

  Welcome to your mountain sanctuary in the heart of Solitude Village—Okemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great

  Joseph Karl William Raveis Real Estate Vermont Properties

  165 Moonshadow Dr Unit M-15, Ludlow, VT 05149
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  /26

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  160 Depot St, Chester, VT 05143

  Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

  Joshua Lemieux Remax Summit

  160 Depot St, Chester, VT 05143
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  /47

  $470,000

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  400 E Lake Rd, Ludlow, VT 05149

  Versatile Ludlow retreat on 9 acres with proven short-term rental history, offering flexible living options ideal for owner-occupants or investors seeking income near Okemo Mountain. This property is configured as a single-family residence with two distinct living levels, each featuring private entrances and amenities that allow for multiple use scenarios. The ground floor living area includes a

  Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

  400 E Lake Rd, Ludlow, VT 05149
• 

  

  /55

  $259,900

  • 4 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  22 Coolidge Rd, Springfield, VT 05156

  Room for everyone with 4 bedrooms and 2 and 1/4 baths! A large primary bedroom, a bathroom with walk in shower, full laundry and a 2nd 1/4 bath ALL on the 1st level! Affordable too! Comfort, Convenience & Timeless Functionality are All Here in One Address.This well-maintained 4-bedroom, 2 full bath home delivers. Includes a first-floor bedroom, full bath, and laundry, ideal for flexible

  Jen Baker Connecticut River Valley Realty

  22 Coolidge Rd, Springfield, VT 05156
• 

  

  /60

  $1,150,000

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  764 Upper Sparrow Hawk Rd, Rochester, VT 05767

  Where Mountain Living Meets Modern Design. Set on 7.3± private acres in the heart of Vermont’s premier ski country, this extraordinary retreat offers a rare blend of refined luxury and natural beauty. Thoughtfully renovated and expanded, the home showcases over 2,500 finished square feet of curated living space with sweeping views of Killington and Pico, and seasonal glimpses of Camel’s Hump and

  The Hammond Team KW Vermont

  764 Upper Sparrow Hawk Rd, Rochester, VT 05767
• 

  

  /51

  $1,359,000

  • 4 Beds
  • 3 Baths
  • 2,882 Sq Ft

  1355 Podunk Rd, White River Junction, VT 05001

  Perched in the hills of Norwich, Vermont, this curated "Scandinavian-esk" property offers exceptional contemporary living surrounded by nature's inspiring beauty. Architecturally redesigned by Smith and Vansant in 2010, this home offers an open floor plan with easy gathering spaces bathed in natural light and warmed by the Finnish Tulikivi soapstone stove. The French doors open to a patio, an

  Wynne Washburn Coldwell Banker LIFESTYLES - Hanover

  1355 Podunk Rd, White River Junction, VT 05001
• 

  

  /40

  $2,950,000

  • 6 Beds
  • 6 Baths
  • 5,433 Sq Ft

  61 Academy Cir, Woodstock, VT 05071

  Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

  Carol Wood Williamson Group Sothebys Intl. Realty

  61 Academy Cir, Woodstock, VT 05071
• 

  

  /37

  $435,000

  • 4 Beds
  • 2.5 Baths
  • 2,125 Sq Ft

  143 Okemo Acres, Ludlow, VT 05149

  Charming Fixer-Upper in a Dream Location – Your Canvas Awaits! Step into a world of endless possibilities with this house, nestled in the heart of a picturesque neighborhood just a mere 0.8 miles from the magnificent Okemo Mountain. This property is not just a house; it’s a golden opportunity for those with a vision, a passion for design, and a desire to create a home that reflects their unique

  Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

  143 Okemo Acres, Ludlow, VT 05149

Showing Results 41 - 80, Page 2 of 6