Windsor County VT Houses for Sale

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  /48

  $319,000

  • 3 Beds
  • 1.5 Baths
  • 1,813 Sq Ft

  4457 Vt Route 14, South Royalton, VT 05068

  A classic 1850 cape minutes from S. Royalton, home of VT Law & Graduate School, the well-stocked S. Royalton Market Food Coop, restaurants, and town center. A large ~1 acre lot with White River frontage. A wonderful aspect of this home is it has kept most of its original charm including wide pine plank floors, doors, and hardware. Enjoy spending time on the roomy, screened front porch just

  Lorraine Checchi Coldwell Banker Hickok & Boardman / E. Montpelier

  4457 Vt Route 14, South Royalton, VT 05068
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  /43

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft

  36 Graham St, Bethel, VT 05032

  Tucked away on a quiet street just off Route 107, this 3-bedroom, 2-bath home offers a great mix of privacy, practicality, and convenience in the heart of Bethel. Inside, you'll find a functional layout with a spacious laundry room, a recently installed dishwasher, and a pellet stove that efficiently heats the entire home, with oil radiator heat as a backup option. The detached two-car garage

  Jacob Barnes EXP Realty

  36 Graham St, Bethel, VT 05032
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  /40

  $219,000

  • 2 Beds
  • 2 Baths
  • 1,420 Sq Ft

  396 S Main St, Bethel, VT 05032

  Just minutes from downtown Bethel this home has everything you’re looking for! The sunny, gently sloping yard is ideal for gardening, or hosting gatherings.Inside, you'll find two bedrooms and two full bathrooms, a spacious living room, and a bright kitchen that opens to a large dining room with sliding doors leading to a private deck overlooking the backyard.Both bedrooms are

  Nathan Mastroeni

  396 S Main St, Bethel, VT 05032
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  /59

  $439,000

  • 4 Beds
  • 2 Baths
  • 2,264 Sq Ft

  264 Elm Hill St, Springfield, VT 05156

  No words describe this property better than a peaceful, bright, historic gentleman farm. This classic post and beam home, the third oldest in Springfield was built in the early 1790's by James Litchfield when he settled in Springfield to farm 64 acres atop of Elm Hill. Although the land was farmed, currently, the site has been reduced to a manageable 1.2 acres. The original axe-cut posts and

  Carol Cole BHG Masiello Brattleboro

  264 Elm Hill St, Springfield, VT 05156
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  /51

  $410,000

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

  663 Depot St, Chester, VT 05143

  Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

  Betsy Adamovich Real Broker LLC

  663 Depot St, Chester, VT 05143
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  /60

  $869,000

  • 4 Beds
  • 4.5 Baths
  • 4,088 Sq Ft

  1588 Austin Hill Rd, Rochester, VT 05767

  An iconic Robert Carl Williams design, completely reimagined by Robson Bilgen Architects in 1999, this one-of-a-kind masterpiece in Rochester’s Great Hawk community is a work of art inside and out. Perfectly sited on 2.7 acres of lush, landscaped grounds, it feels like a private sanctuary, with sweeping pagoda-inspired rooflines, recirculating ponds and waterfalls, dramatic stonework, and vibrant

  Kyle Kershner Killington Pico Realty

  1588 Austin Hill Rd, Rochester, VT 05767
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  /51

  $350,000

  • 5 Beds
  • 4 Baths
  • 2,963 Sq Ft

  513 Giddings St, Springfield, VT 05150

  Nestled on over an acre +/- of level land, this well-maintained home offers a wealth of space and potential for any lifestyle. With a large shed, a 3-car carport/workshop, and even a chicken coop, you'll have plenty of room to store, work, and play. The first floor features a generously-sized bedroom with bay windows, a beautifully refinished bathroom with a walk-in shower, a large kitchen,

  Chelsea Richardson Barrett and Valley Associates Inc.

  513 Giddings St, Springfield, VT 05150
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  /33

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  17 Vermont 12, Hartland, VT 05048

  1850 home re-furbished top to bottom for modern amenities with antique charm. New roof, floors, kitchen, bathrooms, windows, electrical, plumbing, and heating throughout. Very large flat yard located right downtown.

  Derek Eisenberg Continental Real Estate Group, Inc.

  17 Vermont 12, Hartland, VT 05048
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  /32

  $2,300,000

  • 4 Beds
  • 4.5 Baths
  • 3,524 Sq Ft

  134 Chester Arthur Rd, Hartford, VT 05047

  A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

  John Wetmore Wetmore Real Estate

  134 Chester Arthur Rd, Hartford, VT 05047
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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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  /30

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  34 Fox Chair Terrace, Springfield, VT 05156

  Welcome to 34 Fox Chair Terrace, a peaceful, private three-bedroom, two-bath home set on a full acre just minutes from downtown Springfield and charming Chester, Vermont. Tucked away in a quiet rural setting, this spacious property offers the best of both worlds: privacy and nature, with easy access to shopping, schools, the local hospital, and other area amenities.Step inside to find a

  Patrick Kelley Four Seasons Sotheby's Int'l Realty

  34 Fox Chair Terrace, Springfield, VT 05156
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  /38

  $1,999,000

  • 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 of the well known amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round

  John Wetmore Wetmore Real Estate

  5518 Vt Route 12, Barnard, VT 05031
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  /25

  $359,000

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft

  78 Division St, Hartford, VT 05001

  This cozy, well cared for New Englander is move in ready. Enjoy the passive income as a two unit, or use it as a single family home. The choice is yours. The house has a nice boot room to organize all of those winter layers leading into a kitchen that flows into the living room. The first floor bedroom is a nice option. Public transportation is nearby and so are biking trails. Kilowatt field is a

  Josh Hunt Snyder Donegan Real Estate Group

  78 Division St, Hartford, VT 05001
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  /37

  $1,185,000

  • 4 Beds
  • 3 Baths
  • 2,785 Sq Ft

  1782 Randall Rd, Woodstock, VT 05091

  This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

  Wade Treadway Wade I Treadway Real Estate

  1782 Randall Rd, Woodstock, VT 05091
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  /29

  $169,500

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  1438 Gravelin Rd, Perkinsville, VT 05151

  Country Setting on a shared drive surrounded by 3 acres w/ a small pond. First floor has 1 BR, full bath, kitchen/dining area and living room. Lower level has 1 BR and laundry room. Heat is a propane Rannai direct vent, plus a lower-level pellet stove. Property is in need of repair but livable. This is an ideal candidate for a 203K loan.

  Don Chabot Town and Country Realty

  1438 Gravelin Rd, Perkinsville, VT 05151
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  /59

  $1,750,000

  • 5 Beds
  • 4 Baths
  • 3,862 Sq Ft

  699 Spear Cemetery Rd, Reading, VT 05062

  Situated amongst the finest equine estates in the region, Tuacknback Farm is an iconic landmark, best known as the most popular hold along the famed Vermont 100 ride. Located on a scenic country road, accessing the most extensive trail systems in New England, the entire property was impeccably orchestrated for ease with direct walk-in access to the connected stable and hay loft, and a wide

  Danny Kogut Williamson Group Sothebys Intl. Realty

  699 Spear Cemetery Rd, Reading, VT 05062
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  /60

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  442 Vermont 103, Chester, VT 05143

  Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

  Rachael Rogala Rachael Rogala Inc.

  442 Vermont 103, Chester, VT 05143
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  /26

  $194,500

  • 2 Beds
  • 1 Bath
  • 942 Sq Ft

  37 Coolidge Rd, Springfield, VT 05156

  Back on Market and now listed BELOW appraised value! Charming Dutch Colonial just moments from the hospital! This adorable 2-bedroom, 1-bath home is perfect for first-time buyers or those looking to downsize. Located on a quiet side street, you’ll enjoy the peaceful setting with the convenience of nearby amenities. The main level offers a cozy living room and a combined kitchen/dining area, while

  Betsy Adamovich Real Broker LLC

  37 Coolidge Rd, Springfield, VT 05156
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  /57

  $2,190,000

  • 4 Beds
  • 3.5 Baths
  • 4,313 Sq Ft

  7 Norman Dr, Ludlow, VT 05149

  This is a rare opportunity to own a stunning year-round residence on the shores of Lake Rescue, nestled within a sought-after community that includes Okemo Mountain Ski Resort—offering the ultimate four-season lifestyle. Ideally located on the coveted east side of the lake, the home is perfectly positioned to capture afternoon sun and dramatic sunsets over the water.Beautifully landscaped

  Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

  7 Norman Dr, Ludlow, VT 05149
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  /30

  $465,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  37 Atwood Ave, Woodstock, VT 05091

  Charming, updated, and perfectly located—this turnkey gem is your ticket to easy living in one of the area’s most adorable neighborhoods! With all the major systems recently upgraded - including a new furnace, hot water heater, Tesla Powerwall, and water purification system - this efficient home is move-in ready.Inside, you’ll love the fresh renovations: a modern kitchen with

  Keri Cole Williamson Group Sothebys Intl. Realty

  37 Atwood Ave, Woodstock, VT 05091
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  /36

  $895,000

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

  1104 Main St, Cavendish, VT 05142

  Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuite, 5 bath log home. The Great Room boasts a floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is

  Frank Provance Diamond Realty

  1104 Main St, Cavendish, VT 05142
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  /48

  $1,275,000

  • 4 Beds
  • 3 Baths
  • 3,796 Sq Ft

  204 High Ridge Rd, Brownsville, VT 05037

  This hidden gem is one of the best kept secrets in West Windsor. Sited at the end of a private road with rolling green lawns, and a tree top view of Mount Ascutney, this lovingly stewarded home was impeccably constructed and orchestrated with flowing wide open, bright spaces. The perfect home for full or part time living, and entertaining. The living room is anchored by a painted brick Rumford

  Danny Kogut Williamson Group Sothebys Intl. Realty

  204 High Ridge Rd, Brownsville, VT 05037
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  /16

  $250,000

  • 5 Beds
  • 2 Baths
  • 1,728 Sq Ft

  101 Mount Vernon St, Springfield, VT 05156

  Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect

  Christine Lewis Brattleboro Area Realty

  101 Mount Vernon St, Springfield, VT 05156
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  /32

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 3,592 Sq Ft

  233 Brothers Rd, Hartland, VT 05048

  The idyllic Hartland countryside is the setting for this handsome cape. A delightful three season porch is entered by way of the attached two car garage or directly by a lovely landscaped pathway. Once inside you will be greeted by a warm and inviting kitchen detailed with cherry cabinetry, the dining room with a bay window view of the gardens,a living room with fireplace, and a spacious

  Mary Mayhew Snyder Donegan Real Estate Group

  233 Brothers Rd, Hartland, VT 05048
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  /19

  $359,900

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  302 Davidson Hill Rd, Chester, VT 05143

  This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity

  Thaddeus Abare Barrett and Valley Associates Inc.

  302 Davidson Hill Rd, Chester, VT 05143
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  /56

  $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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  /34

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  842 Main St, Proctorsville, VT 05153

  Cared for by one owner for many years, this two-story 3 bedroom, 2 bath home on .26 +/- acres was built in 1977 and would make a very cute ski house or full-time home. Enter through the enclosed breezeway, a great space for entertaining and relaxing. The eat-in kitchen includes a breakfast/dining nook and excellent counter space. The living room is spacious and has plenty of natural light. A

  Geralyn Donohue Engel & Völkers Okemo

  842 Main St, Proctorsville, VT 05153
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  /42

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,776 Sq Ft

  64 Summer Hill St, Springfield, VT 05156

  Tucked in one of Springfield’s most sought-after neighborhoods, 64 Summer Hill St offers the perfect blend of comfort, charm, and convenience. This beautifully maintained 3-bedroom, 2-bath home nestled in one of Springfield’s most desirable neighborhoods. Located on a peaceful .28acre lot in the Cherry Hill district, this inviting property offers the perfect balance of comfort and convenience.

  Jamie Watson BHG Masiello Keene

  64 Summer Hill St, Springfield, VT 05156
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  /60

  $1,795,000

  • 4 Beds
  • 6.5 Baths
  • 6,269 Sq Ft

  73 Laber Rd, Bridgewater Corners, VT 05035

  Experience elevated Vermont living with this exceptional mountaintop estate, thoughtfully designed for both comfort and flexibility. Set on nearly 30 private acres, the residence combines timeless architectural style with expansive interiors and truly breathtaking panoramic views—including sightlines to 4,000-foot peaks and Killington’s ski trails.Inside, you’ll find a rare level of

  Keri Cole Williamson Group Sothebys Intl. Realty

  73 Laber Rd, Bridgewater Corners, VT 05035
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  /30

  $434,500

  • 3 Beds
  • 1.5 Baths
  • 1,582 Sq Ft

  7873 Pomfret Rd, North Pomfret, VT 05053

  Great location to both historic Woodstock and the Upper Valley. This charming cape has lots of antique characteristics with original wood floors and accented with hand hewn beams. The second floor was expanded with taller ceiling height, new windows and insulation. Kitchen flows to a large dining room with half bath and laundry on first floor. Large sunlit living room off the North end of the

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  7873 Pomfret Rd, North Pomfret, VT 05053
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  /25

  $359,000

  • 3 Beds
  • 1,504 Sq Ft

  1749 Middletown Rd, Andover, VT 05143

  Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the

  Gary Coger Four Seasons Sotheby's Int'l Realty

  1749 Middletown Rd, Andover, VT 05143
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  /24

  $550,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  2179 U S 4, Bridgewater, VT 05035

  Looking for the tranquility of rural life? Charming, well built, vacation cabin, off the grid, on 30+ acres, with stunning views of Killington. Cabin has 2 bedrooms, 1 bath and a loft, 80% finished including roughed-in bath. Perfect get away from the bothers and troubles of the world, high above the valley with great views of the nearby mountains. Beautiful wood floors, full kitchen and lovely

  John MacGovern Dark Horse Realty

  2179 U S 4, Bridgewater, VT 05035
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  /57

  $877,000

  • 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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  /60

  $875,000

  • 6 Beds
  • 5 Baths
  • 3,192 Sq Ft

  65 Andover St, Ludlow, VT 05149

  This stunning, turnkey three-unit property is perfect as a family compound, investment opportunity, or live/rent scenario. The main home features two updated units: a 3-bedroom, 2-bath lower-level apartment with a beautiful covered porch, and a 3-bedroom, 2-bath upper-level apartment with its own smaller porch. Behind the main home sits a two-story 1-bedroom carriage house with radiant electric

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  65 Andover St, Ludlow, VT 05149
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  /51

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft

  162 Bear Hill Rd, Plymouth, VT 05056

  Beautifully renovated 3-bedroom, 2.5-bath chalet perched on the slope of the former Plymouth Notch Ski Area. This move-in-ready home combines mountain charm with modern comfort. Interior upgrades include new flooring, fully renovated bathrooms, stylish lighting, and a refreshed kitchen with granite countertops, tile backsplash, pot filler, and all-new stainless steel appliances. The open-concept

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  162 Bear Hill Rd, Plymouth, VT 05056
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  /25

  $495,000

  • 3 Beds
  • 1 Bath
  • 895 Sq Ft

  121 E Lake Rd, Ludlow, VT 05149

  Charming Lake Cottage with Over 113 +/-Feet of Waterfront on Lake Pauline.Lovingly maintained by the same family since the 1940s, this delightful lakefront cottage is a rare find. Step inside to discover original touches like tongue-and-groove paneling and vintage details that evoke a simpler time, all thoughtfully preserved. Modern updates blend seamlessly with its nostalgic charm and

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

  121 E Lake Rd, Ludlow, VT 05149
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  /39

  $875,000

  • 3 Beds
  • 5 Baths
  • 4,532 Sq Ft

  151 Smokerise, Ludlow, VT 05149

  Entertain in Style in this VERY spacious home on 3.52 acres of paradise. Make memories and invite all of your friends and family to this tasteful home with room for everyone and more. Large living room, with wood burning stone fireplace, lovely views and a slider to the wrap around expanded deck. Inviting custom country kitchen with island and granite countertops along with 2 bedrooms and a full

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  151 Smokerise, Ludlow, VT 05149
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  /32

  $2,250,000

  • 2 Beds
  • 4 Baths
  • 3,514 Sq Ft

  611 Simmons Rd, Chester, VT 05143

  Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

  Dia Jenks LandVest, Inc/Woodstock

  611 Simmons Rd, Chester, VT 05143
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  /60

  $549,000

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft

  352 Edwins Pond Rd, Rochester, VT 05767

  Welcome to Tranquility in Vermont.This charming three-bedroom, two-bath home invites you to unwind and enjoy the peaceful beauty of Vermont living. With both a spacious great room and a cozy living room—each warmed by its own wood stove—you’ll always have the perfect place to relax.The home features wide plank wood floors throughout, a brand-new heating system with on-demand hot

  Katie McFadden RE/MAX North Professionals

  352 Edwins Pond Rd, Rochester, VT 05767
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  /60

  $3,650,000

  • 5 Beds
  • 4 Baths
  • 5,181 Sq Ft

  348 Turtle Hill Rd, Ludlow, VT 05149

  Built over the course of two years and completed in 2023, this nearly new custom timberframe home showcases exceptional craftsmanship and fine attention to detail. Privately sited on over 13 acres, the property offers sweeping, panoramic views of southern Vermont's mountains and valleys; vistas that are truly second to none. The home's architectural highlights include hand-hewn Douglas fir beams

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  348 Turtle Hill Rd, Ludlow, VT 05149

Showing Results 121 - 160, Page 4 of 8