Windsor County VT Homes for Sale

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  /25

  $339,000

  • 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

  $985,000

  • 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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  /49

  $739,000

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  228 Leonard Rd, Sharon, VT 05065

  Welcome to your private Vermont retreat on nearly 24 acres of open meadows, woods, and a pristine spring-fed pond. Tucked away in complete seclusion and surrounded by 500 acres of undeveloped maple forest, this peaceful property offers unrivaled privacy and natural beauty. The charming 3-bedroom home features hardwood floors, a cozy wood stove, and a beautifully renovated kitchen with granite

  Mandolyn McIntyre Crow Real Broker LLC

  228 Leonard Rd, Sharon, VT 05065
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  /32

  $72,999

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  185 Riverbend Way, Woodstock, VT 05091

  Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

  Mendi Michael Engel & Völkers Okemo

  185 Riverbend Way, 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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  /58

  $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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  /37

  $439,000

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

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056

  PRICED TO SELL - Come take a look - the views are amazing! Time to get the Fireplace crackling at this Mountain Retreat in Plymouth before the snow flies... This spacious four-bedroom, three-bathroom condo is nestled in the scenic hills of Plymouth, perfectly located between Killington and Okemo for easy access to world-class skiing, snowboarding and year-round mountain and lake

  Katie McFadden RE/MAX North Professionals

  1226 E Ash Rd Unit L-34, Plymouth, VT 05056
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  /57

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 2,585 Sq Ft

  117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149

  Ledgewood on Okemo, a spacious condominium located in one of the most sought-after communities on Okemo Mountain. This property offers an abundance of space, featuring two en-suites and two additional bedrooms. The expansive great room opens to a large family kitchen with two breakfast bars, providing ample seating for the whole family. You'll also appreciate the private ski-in/ski-out access and

  Katherine Burns William Raveis Real Estate Vermont Properties

  117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149
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  /42

  $945,000

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft

  360 Okemo Trailside Extension Unit 37B, Ludlow, VT 05149

  It Truly is About Location! Sitting directly on the Sachem Trail this 3 bedroom townhome is one of the best locations on Okemo Mountain. You can access the trail either through the enlarged custom designed mudroom or step out onto the snow from the lower level sliding door. Either way this is the location that you are looking for! The kitchen is spacious, updated and open to the light-filled

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

  360 Okemo Trailside Extension Unit 37B, Ludlow, VT 05149
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  /34

  $240,000

  • 2 Beds
  • 1.5 Baths
  • 1,140 Sq Ft

  104 Deer Run Rd Unit C13, Brownsville, VT 05037

  Welcome to this nicely maintained 2-bedroom + loft condo offering direct access to the renowned Ascutney Trails—perfect for mountain biking, skiing, hiking, and trail running. Enjoy stunning mountain views from the spacious living room, which features two large sliding glass doors that flood the space with natural light. The open loft above the living area offers even more scenic vistas and

  Daniel Preston KW Vermont Woodstock

  104 Deer Run Rd Unit C13, Brownsville, VT 05037
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  /52

  $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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  /54

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 1,842 Sq Ft

  182 Okemo Trailside Extension Unit 42 D, Ludlow, VT 05149

  This nicely updated 3 bedroom plus family room townhome has stunning views to the east in a mid- mountain setting.Enjoy the large updated kitchen with wood cabinetry, stone countertops, and wood crafted breakfast bar. The open living area with cathedral ceiling centered by a woodburning fireplace, leads out to a covered deck and hot tub offering spectacular mountain views. The private primary

  Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  182 Okemo Trailside Extension Unit 42 D, Ludlow, VT 05149
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  /30

  $420,000

  • 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 solid-surface

  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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  /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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  /2

  $450,000

  • Land
  • 119 Acres
  • $3,782 per Acre

  00 Bradley Hill Rd, Norwich, VT 05055

  Unusually large parcel of land in Norwich. 119 +/- ac with over 2500' of road frontage on delightful Bradley Hill Road. Close to town yet calm and quiet.

  Jane Darrach Martha E. Diebold/Hanover

  00 Bradley Hill Rd, Norwich, VT 05055
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  /14

  $199,000

  • Land
  • 27.1 Acres
  • $7,343 per Acre

  00 Albin Hill Rd, Braintree, VT 05060

  Imagine waking up to sweeping vistas of Vermont’s Green Mountains, surrounded by 27.1 acres of pure tranquility. This rare parcel offers the perfect canvas for your dream estate, luxury retreat, or off-the-grid sanctuary. Perched at an impressive 1,800 feet in elevation, the property offers stunning panoramic views and unparalleled privacy, while still being just minutes from amenities, shopping

  Will Spanos KW Vermont-Killington

  00 Albin Hill Rd, Braintree, VT 05060
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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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  /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

  $550,000

  • 1 Bed
  • 2 Baths
  • 1,112 Sq Ft

  193 Jackson Gore Unit 639/641, Ludlow, VT 05149

  Escape to mountain luxury with this fully furnished 1-bedroom, 2-bathroom condo located in the heart of the premier Okemo ski resort at Jackson Gore. Perfectly positioned just steps from the slopes, this stylish retreat offers the ultimate blend of comfort, convenience and year round adventure. The open-concept living space features a cozy gas fireplace and large windows with mountains views.

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

  193 Jackson Gore Unit 639/641, Ludlow, VT 05149
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  /19

  $325,000

  • Land
  • 18 Acres
  • $18,056 per Acre

  00 Turtle Hill Rd, Ludlow, VT 05149

  Build Your Dream Home on a Private 18-Acre Estate in South HillDiscover the perfect setting for your custom-designed residence on this expansive 18-acre parcel, ideally situated at the secluded end of a cul-de-sac within South Hill's exclusive community. This exceptional property offers a rare blend of privacy and convenience, surrounded by other custom-built homes. Imagine your new home

  Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

  00 Turtle Hill Rd, Ludlow, VT 05149
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  /36

  $699,900

  • 4 Beds
  • 4 Baths
  • 3,780 Sq Ft

  5 Malagash Rd, South Reading, VT 05153

  Set on a spacious and level lot in the scenic countryside of Reading, Vermont, this raised ranch offers room to spread out both inside and out. With 4 bedrooms and 4 bathrooms, the home provides flexible living options across two levels—perfect for larger households, multi-generational living, or hosting guests. The bright main floor features an open layout with a comfortable living area, an

  Katie Ladue Gilbert KW Vermont Woodstock

  5 Malagash Rd, South Reading, VT 05153
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  /34

  $289,000

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

  842 Main St, Proctorsville, VT 05153

  Priced to sell! Discover your Vermont getaway with this charming 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on .26± acres combines comfort and convenience in one of the most desirable areas of the Okemo Valley. Enjoy a spacious living room and bright eat-in kitchen

  Geralyn Donohue Engel & Völkers Okemo

  842 Main St, Proctorsville, VT 05153
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  /42

  $389,900

  • 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

  $1,490,000

  • 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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  /49

  $675,000

  • 3 Beds
  • 3 Baths
  • 1,376 Sq Ft

  97 Okemo Trailside Extension Unit 15 C, Ludlow, VT 05149

  Welcome to Trailside 15-C. This recently renovated condo is ready for the next loving family. The natural light filled well appointed condo is turn key and just steps from the slopes. Step into the spacious mudroom with ample hooks, and cubbies to store your gear neatly and a live edge bench to put on your boots. You'll feel right at home when you walk into the light filled open living

  Frank Provance Diamond Realty

  97 Okemo Trailside Extension Unit 15 C, Ludlow, VT 05149
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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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  /26

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,349 Sq Ft

  19 Kettlebrook Rd Unit D-5, Ludlow, VT 05149

  Direct ski-on, ski-off two-bedroom top-floor unit in the Kettlebrook community. Nicely updated throughout. Enclosed mudroom entrance with built-ins, laundry, and exterior ski closet. The main level includes a well-designed kitchen and a separate dining area with a newly installed slider leading out to the deck, which looks out to the slopes; a living room with a wood burning fireplace and

  Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  19 Kettlebrook Rd Unit D-5, Ludlow, VT 05149
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  /16

  $400,000

  • Land
  • 13.94 Acres
  • $28,694 per Acre

  0 Gill Terrace Unit 5050286, Ludlow, VT 05149

  In Ludlow Village! 13+ acre wooded lot boasts a direct view of Okemo Mountain! Power and shared driveway on the lot. Old ATV trails run through. Some seasonal drainages but mostly rolling, walkable terrain. It drops off severely on the west side above the cemmetary. A simple WALKING TRAIL FROM the DRIVEWAY on the right follows "dotted flagging" and gets one into the best areas of the land. The

  Don Eatmon Kelley Real Estate, Inc.

  0 Gill Terrace Unit 5050286, Ludlow, VT 05149
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  /18

  $199,000

  • Land
  • 18.78 Acres
  • $10,596 per Acre

  00 Boynton Rd, Londonderry, VT 05148

  Located off quiet, town-maintained Boynton Road in Londonderry, this nearly 20-acre wooded parcel offers the perfect opportunity to build your dream home in the heart of southern Vermont. With power and fiber optic internet available at the street and a state-issued wastewater permit in place for a five-bedroom residence, this raw land is ready for your vision. A small stream runs parallel to the

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  00 Boynton Rd, Londonderry, VT 05148
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  /4

  $125,000

  • Land
  • 11.63 Acres
  • $10,748 per Acre

  0 Goulden Ridge Rd Unit 5050178, Weathersfield, VT 05151

  Beautiful and very accessible wooded lot, mere minutes to Exit 8 off Route 91, and all that the Upper Valley has to offer. 25 minutes to Hanover, New Hampshire or Woodstock, Vermont. Has potential lovely views of Mt. Ascutney and east to the distant hills of New Hampshire. This beautiful parcel offers a unique opportunity to own property in Vermont that has many practical values. Turn your vision

  John MacGovern Dark Horse Realty

  0 Goulden Ridge Rd Unit 5050178, Weathersfield, VT 05151
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  /2

  $175,000

  • Land
  • 17 Acres
  • $10,294 per Acre

  tbd Quarry Hill Rd, Rochester, VT 05767

  North Hollow offers the beauty and country setting you expect from Vermont. This land parcel is subdivided off a homesite with an added parcel to complete the 17 acres. Situated off the roadside, you will enjoy privacy and mountain views. Perfect for a solar installation with southwest exposure. Better yet, this parcel is across the street from access to the ROC Mt bike trail system. Only 30

  Patricia Harvey Xsell Realty LLC

  tbd Quarry Hill Rd, Rochester, VT 05767
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  /15

  $85,000

  • Land
  • 4.05 Acres
  • $20,988 per Acre

  00 Hillcrest Dr, Andover, VT 05143

  Ready to Build in Southern Vermont! Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for remote work

  Daire Gibney Barrett and Valley Associates Inc.

  00 Hillcrest Dr, Andover, VT 05143
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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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  /21

  $55,000

  • Land
  • 1.52 Acres
  • $36,184 per Acre

  0 Remington Rd Unit 5049900, Chester, VT 05143

  If you're dreaming of open skies, peaceful surroundings, and your own slice of Vermont, this property delivers. Just minutes from the charming Chester village green, this land offers the best of both worlds—seclusion and convenience. Step onto the property and take in the wide-open space surrounded by mature trees, offering privacy and natural beauty in every season. Whether you're envisioning

  Frank Provance Diamond Realty

  0 Remington Rd Unit 5049900, Chester, VT 05143
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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

  $425,000

  • 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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  /32

  $1,995,000

  • 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
• 

  

  /38

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 1,974 Sq Ft

  85 Rimrock Rd Unit 13A, Ludlow, VT 05149

  Excellent value priced to sell - Prime location, ski-on, ski-off with direct access to Sachem Trail, with just a few steps from your door, and you'll be on the slopes! This is a bright and sunny condo featuring 3 bedrooms, 2.5 bathrooms, and a loft. The living and dining area features a cathedral ceiling, a wood-burning fireplace, and a deck offering a long-distance view. Recent updates include

  Karen Wilson TPW Real Estate

  85 Rimrock Rd Unit 13A, Ludlow, VT 05149
• 

  

  /19

  $825,000

  • Land
  • 0.9 Acre
  • $916,667 per Acre

  1049 N Main St, Hartford, VT 05001

  Among last of retail sites at this high demand and very limited commercial zoned properties at this intersection of I-89 and I-91. Just off ramp, visible to travelers at exit. Adjacent to new roundabout. Frontage on I-91 northbound. (sign restrictions to 25ft height, 150 sf). Underserved market for highway travelers into VT & NH. 40,000 VPD combined for I-89 and I-91. 10,000 VPD curbside. Lack of

  James Ward GRI Equity Group Real Estate Broker Inc.

  1049 N Main St, Hartford, VT 05001

Showing Results 281 - 320, Page 8 of 13