Windsor County VT Homes for Sale

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  /27

  $500,000

  • Land
  • 0.94 Acre
  • $531,915 per Acre

  M-17 Moonshadow Dr, Ludlow, VT 05149

  Solitude Village on Okemo Mountain - a fantastic building lot located on Okemo Mountain, within one of its most desirable communities. This is one of the last remaining lots available, offering the unique opportunity to build your dream home in the tranquil Solitude Village. The property boasts direct ski-to-door access, and you can easily walk down to the community pool. Rest assured, the

  Katherine Burns William Raveis Real Estate Vermont Properties

  M-17 Moonshadow Dr, Ludlow, VT 05149
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  /30

  $375,000

  • 1 Bed
  • 1 Bath
  • 884 Sq Ft

  162 Okemo Trailside Extension Unit 22C-L, Ludlow, VT 05149

  Okemo Trailside 22-CL is a spacious one-bedroom with a bunk room, ideally located just a minute's walk from the Upper Sachem Trail. This ski-in/ski-out condo, which has seen significant renovations, offers flat, easy access to the slopes and community amenities. Inside, you'll find an open 884-square-foot layout. The entry features a mudroom with rustic pine accents, perfect for storing gear. The

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

  162 Okemo Trailside Extension Unit 22C-L, Ludlow, VT 05149
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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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  /19

  $295,000

  • Land
  • 10.01 Acres
  • $29,471 per Acre

  713 S Hill Rd, Ludlow, VT 05149

  Dear future homeowner! Imagine your dream property just waiting for you and this 10-acre slice of paradise on South Hill Road is exactly that! This isn't just land; it's your blank canvas, totally prepped and ready to bring your vision to life.Critical infrastructure elements already done for you! We're talking a new fully installed 5-bedroom septic system that's good to go, an awesome

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

  713 S Hill Rd, Ludlow, VT 05149
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  /43

  $445,000

  • 3 Beds
  • 3 Baths
  • 1,918 Sq Ft

  11 Blueberry Ledge Ridge Unit L3, Plymouth, VT 05056

  Ledges 3--This updated 3-bedroom, 3-bath townhouse offers a welcoming retreat in the lakes region, midway between Killington and Okemo. Renovated in 2013, the home features a stylish kitchen with new cabinetry, quartz countertops, tiled backsplash, cork flooring, and quality appliances including a gas range. The main level is warm and inviting with random-width pine floors and a wood-burning

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  11 Blueberry Ledge Ridge Unit L3, Plymouth, VT 05056
• 

  

  /35

  $495,000

  • 4 Beds
  • 3 Baths
  • 2,470 Sq Ft

  3364 W Woodstock Rd, Woodstock, VT 05091

  Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway. Inside, you’ll find four comfortable bedrooms and a warm, inviting layout designed for making memories. Gather

  Keri Cole Williamson Group Sothebys Intl. Realty

  3364 W Woodstock Rd, Woodstock, VT 05091
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  /22

  $140,000

  • 3 Beds
  • 1 Bath
  • 1,368 Sq Ft

  56 Furnace St, Springfield, VT 05156

  Attention investors and renovators! This single-family home offers opportunity and potential. The previous owners began renovations, giving you a head start on transforming this property into a profitable project. With the heavy lifting already underway, it’s the perfect canvas for your vision. Features include a first floor mini-split, brand new HVAC system that provides heat and A/C (this still

  Chelsea Richardson Barrett and Valley Associates Inc.

  56 Furnace St, Springfield, VT 05156
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  /17

  $85,000

  • Land
  • 11.51 Acres
  • $7,385 per Acre

  00 Chaos Turnpike, Cavendish, VT 05142

  NOT QUITE off the Grid Hideaway (Verizon 1-4 G) Just down the country lane to Knapp Ponds/Knapp Brook Wildlife Management Area. Forgotten by the owners for the last 30 years, this lot has a mix of timber, stone wall & sloping mountain terrain. 475 feet frontage along the Class 3 road and only a short hike to the ponds. Boat ramps for fishing and hunting access.

  Alexandra Eatmon Kelley Real Estate, Inc.

  00 Chaos Turnpike, Cavendish, VT 05142
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  /59

  $99,000

  • 2 Beds
  • 3 Baths
  • 1,369 Sq Ft

  510/512 Qiii Jackson Gore Adams House Unit 510/512 QIII, Ludlow, VT 05149

  Jackson Gore Village at Okemo – Adams House Condominium. Welcome to slopeside living at its finest in the Adams House at Jackson Gore Village, located at the heart of Okemo Mountain Resort. This spacious and beautifully appointed condominium offers effortless access to the slopes and a full suite of resort amenities. The open-concept living area features a comfortable space to gather, complete

  Joseph Karl William Raveis Real Estate Vermont Properties

  510/512 Qiii Jackson Gore Adams House Unit 510/512 QIII, Ludlow, VT 05149
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  /45

  $795,000

  • 2 Beds
  • 2.5 Baths
  • 1,248 Sq Ft

  144 Lodge Rd Unit 6, Ludlow, VT 05149

  SouthFace Village Tamarack #6Ski-on, ski-off access, luxury amenities, and stunning views await at this beautiful, two-level condominium. This two-bedroom, three-bath unit is steps away from the brand-new recreation building, making it the perfect spot for après-ski relaxation.Inside, you'll find a bright and sunny open-concept living space. A gas fireplace creates a cozy ambiance, while

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

  144 Lodge Rd Unit 6, Ludlow, VT 05149
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  /58

  $495,000

  • 4 Beds
  • 5 Baths
  • 3,350 Sq Ft

  7868 Pomfret Rd, North Pomfret, VT 05053

  A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 3.25 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office space, and the historic U.S. Post Office

  John Bassette Bassette Real Estate Group

  7868 Pomfret Rd, North Pomfret, VT 05053
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  /42

  $3,500,000

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

  18 The Green, Woodstock, VT 05091

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

  Danny Kogut Williamson Group Sothebys Intl. Realty

  18 The Green, Woodstock, VT 05091
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  /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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  /18

  $235,995

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

  2359 Vermont 107, Bethel, VT 05032

  Charming 2-Bedroom, 1 - "Office" VT Route 107 Home — High Ceilings, Hardwood Floors, Garage with Office, and Prime Location Just minutes from Exit 3, this versatile Royalton property blends comfort, convenience, and flexibility—perfect for home living, a small business, or both. Bright, Spacious Living – Soaring high ceilings and beautiful hardwood floors create a warm, open, and inviting

  Nathan Wright Century 21 The One

  2359 Vermont 107, Bethel, VT 05032
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  /10

  $388,888

  • 1 Bed
  • 2 Baths
  • 884 Sq Ft

  807 Murphys Rd Unit 7D, Quechee, VT 05059

  Beautifully updated one-bedroom plus loft condo located in Fairway Village. Recent improvements include new AC mini-splits, updated bathrooms, new flooring, a redesigned staircase with banister, loft safety windows, wood shelving, new shades, and toilets. The condo is part of the Quechee Club, which offers a wide range of amenities (additional club fee applies along with HOA dues). Fairway

  Kris Lippi Get Listed Realty

  807 Murphys Rd Unit 7D, Quechee, VT 05059
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  /50

  $100,000

  • 2 Beds
  • 3 Baths
  • 1,367 Sq Ft

  606/608 QII Jackson Gore Adams House Unit 606/608 QII, Ludlow, VT 05149

  Jackson Gore Village at Okemo Mountain Resort - Welcome to the Adams House at Jackson Gore, where mountainside living meets year-round adventure. This spacious, well-appointed condominium offers comfort and convenience in one of Okemo’s most sought-after slopeside communities. Step inside to find a generous open-concept living space with a cozy gas fireplace, ideal for relaxing after a day on the

  Katherine Burns William Raveis Real Estate Vermont Properties

  606/608 QII Jackson Gore Adams House Unit 606/608 QII, Ludlow, VT 05149
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  /29

  $875,000

  • Land
  • 67.4 Acres
  • $12,982 per Acre

  00 Markham Ln, Weston, VT 05161

  An exceptional Weston land parcel with panoramic views, this property has been family land for generations and is now being offered for sale. A long tree-lined private drive slopes through forest to a cleared, sunny 4-acre field prepared for a house site. The site's elevation at almost 1800 feet backs onto forest and reveals stunning four-season views of the Green Mountain range, rolling hills,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  00 Markham Ln, Weston, VT 05161
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  /35

  $69,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  416 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn, Unit 416 Qtr. I Quarter Ownership - thirteen deeded weeks per year. This one-bedroom, top-floor location is awaiting your family! Its location faces east where you will watch spectacular morning sunrises while sipping on coffee from either your bedroom or living room. There are both hillside and valley views which lend to a peaceful and tranquil environment. With a sleeper sofa

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  416 Qtr I Jackson Gore Inn, Ludlow, VT 05149
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  /17

  $150,000

  • Land
  • 1.04 Acres
  • $144,231 per Acre

  00 Partridge Rd, Ludlow, VT 05149

  A great spot to build a home in the small subdivision of Partridge Road. Close to the Village of Ludlow with access to town sewer. Surrounded by fine properties on South Hill. Covenants and restrictions in place to protect your investment. Quiet and private location yet only minutes to Okemo Mountain Resort and the Village of Ludlow. Come build your dream home!

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  00 Partridge Rd, Ludlow, VT 05149
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  /60

  $1,499,000

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

  652 Tierney Rd, Cavendish, VT 05142

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

  Carol Wood Williamson Group Sothebys Intl. Realty

  652 Tierney Rd, Cavendish, VT 05142
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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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  /44

  $79,500

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

  368/370 Qtr. IV~Enjoy two coveted winter weeks —including Christmas and New Year’s(2025-26)—at this spacious 1-bedroom, 2-bathroom lockout unit at the Jackson Gore Inn at Okemo. Located on the third floor and just steps from the Round House, this unit offers beautiful valley views and ideal proximity to lifts, pools, and dining. Unit C Features: 1 bedroom, sleeps eight, lock-out capabilities, 2

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
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  /29

  $179,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  9 Stryhas Trailer Ct, Ludlow, VT 05149

  Charming and well-maintained 3-bedroom, 2-bathroom manufactured home on leased lot in a peaceful 55+ community. This inviting home features an open concept layout, high ceilings, and is filled with natural light pouring in through multiple skylights, creating a bright and airy atmosphere. Step outside to a new deck with an awning—perfect for enjoying warm summer days. The fenced yard is great for

  Gabrielle Turco Kelley Real Estate, Inc.

  9 Stryhas Trailer Ct, Ludlow, VT 05149
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  /52

  $325,000

  • 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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  /55

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 1,938 Sq Ft

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

  Exceptional Slopeside Living at Okemo. This premier 4-bedroom end unit in Okemo’s coveted Trailside community offers some of the best ski-on/ski-off access on the mountain. Step out your door and ski straight to the high-speed Sunburst Six bubble chair— or walk directly to the Glades Peak Quad, then return home to stunning, unobstructed mountain views.Fully reimagined with a focus on luxury,

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

  360 Okemo Trailside Extension Unit 37E, Ludlow, VT 05149
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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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  /60

  $200,000

  • Land
  • 6.63 Acres
  • $30,166 per Acre

  00 Vermont 103, Andover, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

  Rachael Rogala Lange & Lange

  00 Vermont 103, Andover, VT 05143
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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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  /60

  $115,000

  • Land
  • 3.28 Acres
  • $35,061 per Acre

  00 Vt Route 103 N, Chester, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life.The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing.

  Rachael Rogala Lange & Lange

  00 Vt Route 103 N, Chester, VT 05143
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  /2

  $475,000

  2577 Hartford Ave, Hartford, VT 05001

  Commercial lot - Approximately 1⁄2 acre lot that borders the I-91 highway between the Wilder, VT exit and the Hanover NH/Norwich VT exit. Located on route 5 approximately a quarter mile from Dothan Brook School and 3-4 miles from the Dartmouth green. Property is across the street from walking and biking path, and there is an Advanced Transit bus stop close by as well. There is a separate listing

  Jason Saphire www.HomeZu.com

  2577 Hartford Ave, 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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  /17

  $12,500

  • Land
  • 0.18 Acre
  • $69,444 per Acre

  113 Waterford Ln, Springfield, VT 05150

  Discover the perfect opportunity to build your dream home on this great little lot in a well-maintained & desirable subdivision. Bring your vision with your dream home or use the previously approved permits from the Town of Springfield and the Association, the path to your new home is now clear! Enjoy the convenience of a virtually maintenance-free lifestyle with a low monthly cost of $133,

  

  Ross Doody

  Century 21 Highview Realty

  (802) 230-1798

  113 Waterford Ln, Springfield, VT 05150
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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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  /37

  $419,000

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

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

  SELLERS INCENTIVE - Sellers are willing to pay for Jan and April's 2026 Quarterly HOA Dues if purchase takes place in the next 60 days! Come take a look - the views are amazing! Time to get the Fireplace crackling at this Mountain Retreat in Plymouth now that skiing has begun... This spacious four-bedroom, three-bathroom condo is nestled in the scenic hills of Plymouth, perfectly located between

  Katie McFadden RE/MAX North Professionals

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

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

Showing Results 241 - 280, Page 7 of 11