Windsor County VT 2-Story Homes for Sale

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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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  /60

  $395,000

  • 6 Beds
  • 1 Bath
  • 2,308 Sq Ft

  525 Route 103 N, Chester, VT 05143

  A big price improvement! The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be

  Glenn Olney Barrett and Valley Associates Inc.

  525 Route 103 N, Chester, VT 05143
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  /56

  $594,000

  • 5 Beds
  • 3.5 Baths
  • 3,470 Sq Ft

  1057 Quarry Rd, Chester, VT 05143

  Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

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

  1057 Quarry Rd, Chester, VT 05143
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  /46

  $749,000

  • 4 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  36 Lower IV Unit 48A, Ludlow, VT 05149

  Beautifully Updated Okemo Trailside Townhome. This tri-level end unit has the feel of being in a country home surrounded by lush trees, however it is on the private shuttle route or a short walk to the trail. You enter the enlarged and spacious mudroom, then into the open kitchen/living/dining rooms with sliders to the wrap around deck. The wood burning fireplace warms this floor for a ski lodge

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

  36 Lower IV Unit 48A, Ludlow, VT 05149
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  /44

  $599,000

  • 1 Bed
  • 1.5 Baths
  • 1,044 Sq Ft

  144 Lodge Rd Unit 5, Ludlow, VT 05149

  Slopeside at SouthFace Village Okemo! This may be the nicest one-bedroom condominium currently available on Okemo Mountain. Immaculate and barely used, it comfortably sleeps six and is offered fully furnished, move-in ready for your mountain escape. The interior features stylish quartz countertops, hardwood flooring, built-in shelving, and energy-efficient appliances. Ductless mini-splits provide

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  144 Lodge Rd Unit 5, Ludlow, VT 05149
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  /35

  $614,000

  • 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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  /55

  $2,600,000

  • 4 Beds
  • 4.5 Baths
  • 6,548 Sq Ft

  657 Town Farm Rd, Ludlow, VT 05149

  61 Acre estate with sweeping views and open fields in Ludlow's prestigious South Hill area. Less than 10 minutes to the Okemo ski area and the Ludlow village amenities, this luxury home has received numerous updates in the last several years.Large updated eat-in country kitchen w/ wood cabinetry, stone countertops and updated stainless steel appliances. A gas fireplace with sitting room

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

  657 Town Farm Rd, Ludlow, VT 05149
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  /36

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,452 Sq Ft

  358 Us Route 5 S, Windsor, VT 05089

  Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

  Daniel Preston KW Vermont Woodstock

  358 Us Route 5 S, Windsor, VT 05089
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  /30

  $625,000

  • 3 Beds
  • 3 Baths
  • 4,324 Sq Ft

  3630 Vt Route 103 N, Chester, VT 05143

  Exceptional Investment Opportunity in Chester, VTDiscover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3630 Vt Route 103 N, Chester, VT 05143
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  /60

  $1,450,000

  • 6 Beds
  • 5.5 Baths
  • 4,225 Sq Ft

  515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062

  Nestled in the tranquil hills of West Windsor, Vermont, Rock Haven Estate is a remarkable 33.49-acre country sanctuary offering three separate luxury homes, set along a private drive & surrounded by nature’s beauty. Whether you're looking for a full-time residence with income-generating opportunities or a private family compound, Rock Haven Estate is a rare find! The Rock House - Hilltop Elegance

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062
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  /60

  $2,495,000

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

  248 Gird Lot Rd, Weathersfield, VT 05151

  This meticulously maintained five-bedroom, four-and-a-half-bath home offers sweeping views of the Connecticut River Valley and New Hampshire mountains. Thoughtfully designed for comfort and flexibility, the open-concept layout includes a main-level living option, hardwood floors, and tall ceilings with abundant and expansive windows that flood the home with natural light.The spacious

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
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  /33

  $4,490,000

  • 5 Beds
  • 5.5 Baths
  • 8,122 Sq Ft

  5685 Vermont 12, Barnard, VT 05031

  SEE PROPERTY-SPECIFIC WEBSITE FOR DETAILS, HIGH RESOLUTION PHOTOS, VIDEOS AND MORE. If you’ve been looking for the iconic Vermont home, rarely does an opportunity like this present itself. Welcome to HIGHLAND GLEN, an idyllic Vermont home situated on 12 picturesque acres in the quaint town of Barnard, VT. Upon arrival at Highland Glen, you'll immediately sense the special charm of this

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
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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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  /58

  $635,000

  • 3 Beds
  • 3.5 Baths
  • 2,203 Sq Ft

  44 Freeman Rd Unit B2, Cavendish, VT 05153

  The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This ground floor 3br +loft & den features 3.5 baths. This townhouse condo has floor to ceiling windows that provide natural light throughout. The open living room, dining room, and kitchen offer an inviting atmosphere for gatherings. The ground floor patio offers outdoor seating and has

  Joseph Karl William Raveis Real Estate Vermont Properties

  44 Freeman Rd Unit B2, Cavendish, VT 05153
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  /39

  $450,000

  • 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
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  /48

  $575,000

  • 9 Beds
  • 6 Baths
  • 5,054 Sq Ft

  12 Commonwealth Ave, Ludlow, VT 05149

  A rare find in the heart of the Ludlow Village. This three-family property offers over 5,000 sq. ft. of income-generating space, just steps from the Okemo shuttle and downtown Ludlow! With a strong rental history this property offers both versatility and value. Two of the three units have been beautifully, recently updated and are turn key. One unit used by by the Seller, the second currently

  Frank Provance Diamond Realty

  12 Commonwealth Ave, Ludlow, VT 05149
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  /47

  $674,400

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

  82 Hiram Atkins Byway, Hartford, VT 05001

  Price Reduced! Wonderful colonial style home that has been beautifully maintained, updated and nestled on a semi private lot in Quechee Lakes. Membership gives access to one of Vermont's finest 36 hole golf courses, club house, pool, beach area at lake Pineo, quechee ski hill, pickleball, tennis and is a great spot for biking and hiking. Just a short drive to KILLINGTON, Pico, Saskadena Six Ski

  Alex DeFelice The Clerkin Agency, P.C.

  82 Hiram Atkins Byway, Hartford, VT 05001
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  /30

  $515,000

  • 4 Beds
  • 2.5 Baths
  • 2,238 Sq Ft

  141 N Runway Rd, Perkinsville, VT 05151

  Welcome to this beautifully maintained expanded Cape, perfectly positioned to capture stunning views of the Hartness runway—an aviation enthusiast's dream! Tucked away on a quiet dead-end road, the property offers just the right balance of privacy and convenience, located only 15 minutes from everyday essentials.The main level features a spacious open-concept living and dining area, a

  Allison Griep KW Vermont Woodstock

  141 N Runway Rd, Perkinsville, VT 05151
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  /27

  $539,000

  • 6 Beds
  • 2 Baths
  • 2,304 Sq Ft

  81 High St, Cavendish, VT 05142

  Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the

  Tyleen Murray Kelley Real Estate, Inc.

  81 High St, Cavendish, VT 05142
• 

  

  /25

  $539,000

  • 2,304 Sq Ft

  81 High St, Cavendish, VT 05142

  Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the

  Tyleen Murray Kelley Real Estate, Inc.

  81 High St, Cavendish, VT 05142
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  /57

  $739,000

  • 4 Beds
  • 4 Baths
  • 2,578 Sq Ft

  78 Coopers Trace, Plymouth, VT 05056

  Located in Hawk Resort, midway between Killington and Okemo, this well-maintained four-bedroom, four-bath home offers the ideal blend of privacy and convenience. The main level features an open layout with cathedral ceilings, wide pine floors, and abundant natural light from large windows and skylights. A renovated kitchen and fresh paint throughout add to the home’s bright, updated feel. The

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  78 Coopers Trace, Plymouth, VT 05056
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  /38

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,679 Sq Ft

  707 Skitchewaug Trail, Springfield, VT 05156

  Discover opportunity and flexibility at 707 Skitchewaug Trail in Springfield. This 3-bedroom, 1-bath home sits on 2.8 private acres, combining open yard space and wooded surroundings to create the perfect country setting. With a spacious kitchen and dining area, cozy wood stove in the living room, and first-floor bedroom, bath, and laundry, the layout supports a variety of living needs, from

  Nick Sicard EXP Realty

  707 Skitchewaug Trail, Springfield, VT 05156
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  /29

  $2,000,000

  • 4 Beds
  • 5 Baths
  • 2,887 Sq Ft

  1300 Mountain Rd, Ludlow, VT 05149

  One-of-a-kind location on Okemo Mountain. This property enjoys direct Slopeside access on Okemo's Mountain Road Trail. Land runs down adjacent to the Sidewinder Trail. Above Solitude Village. Northern boundary is the Coleman Brook. Fantastic views to the east with clearing. Current winter access is via ski lift only. Off season access is via the Mountain Road. If you have a vision, this

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  1300 Mountain Rd, Ludlow, VT 05149
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  /51

  $1,250,000

  • 6 Beds
  • 5.5 Baths
  • 5,790 Sq Ft

  49 Burton Rd, Weston, VT 05161

  Location, Views, and Room for Everyone – It’s All Here and Waiting for You! Offering maximum warmth, comfort, and charm, this beautifully-built and well-maintained home features traditional New England architecture on 7+ picturesque and tranquil acres just outside the delightful village of Weston. The inviting layout features classic design and rich architectural details with formal and informal

  Claudia Harris Mary Mitchell Miller Real Estate

  49 Burton Rd, Weston, VT 05161
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  /58

  $549,000

  • 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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  /59

  $410,000

  • 2 Beds
  • 2 Baths
  • 2,400 Sq Ft

  54 Twitchell Settlement, Rochester, VT 05767

  "Nestled on over three private acres, this Vermont retreat exudes rustic charm and modern comfort. The soaring cathedral ceilings and floor-to-ceiling arched windows in the great room flood the space with natural light, creating a warm and inviting atmosphere. The open-concept layout seamlessly connects the kitchen, dining, and living areas, ideal for gatherings or quiet moments by the pellet

  Nick Sicard EXP Realty

  54 Twitchell Settlement, Rochester, VT 05767
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  /60

  $529,000

  • 3 Beds
  • 3.5 Baths
  • 2,203 Sq Ft

  74 Spaulding Rd Unit I-4, Proctorsville, VT 05153

  Welcome to the Castle Hill Resort and Spa community! This well-maintained 3 bedroom plus loft upper-level end unit has over 2200 square feet of space and is just a short drive to skiing and Okemo Mountain Resort amenities. The tiled mudroom entry leads to bright open spaces including the kitchen with breakfast bar, as well as the dining and living areas accented by a cathedral ceiling and

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

  74 Spaulding Rd Unit I-4, Proctorsville, VT 05153
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  /58

  $595,000

  • 6 Beds
  • 3 Baths
  • 3,325 Sq Ft

  29-31 High St, Ludlow, VT 05149

  Location, Location, Location! In the heart of the village, on the coveted, much sought after, quiet High St. is this three family beautiful property. A short stroll to downtown Ludlow and all it has to offer. Two beautiful units in the main house with hardwood flooring, updated kitchens and both with 3 season sun porches. A cozy two bedroom apartment above the three car garage with a covered

  Frank Provance Diamond Realty

  29-31 High St, Ludlow, VT 05149
• 

  

  /19

  $359,000

  • 4 Beds
  • 3 Baths
  • 2,144 Sq Ft

  25 Independent Dr, Hartland, VT 05048

  Affordable, Large multi family building on 6.36+/- acres currently being used as 3 units but has a 4th unit which will need to be finished and updated. This property has lots of space and many options for rental revenue. Add this property to your rental portfolio and rent all four units or Live on site in one unit and have the other three units help pay for your living expenses. This property is

  Alex DeFelice The Clerkin Agency, P.C.

  25 Independent Dr, Hartland, VT 05048
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  /60

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,658 Sq Ft

  141 Upper Crossroad, Ludlow, VT 05149

  Welcome to Okemo's iconic roundhouse. While not completely round, this distinctive home is only about 1,200' from the main base area - an easy walk even in ski boots. It is all about location! You will find 3+ bedrooms, 2 full baths, a sauna, and hardwood floors in the common areas. The wrap-around deck provides views of Okemo ski trails and is great for outdoor entertaining. The mudroom has a

  Kevin Barnes William Raveis Real Estate Vermont Properties

  141 Upper Crossroad, Ludlow, VT 05149
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  /41

  $299,000

  • 4 Beds
  • 1 Bath
  • 1,554 Sq Ft

  2 Pond St, Ludlow, VT 05149

  This charming home, cherished by one family since the mid-1950s, presents a wonderful opportunity for renovation and personalization. This nine room home has 4 bedrooms, 1 bath, and an eat-in kitchen. The location is ideally situated within walking distance of Dorsey Park and Ludlow Village. Catch the shuttle bus to Okemo for a day of skiing or walk to the restaurants, grocery store and all the

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

  2 Pond St, Ludlow, VT 05149
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  /59

  $740,000

  • 6 Beds
  • 7 Baths
  • 3,880 Sq Ft

  815 Vermont Route 100, Weston, VT 05161

  Escape to this enchanting circa 1830 Colonial, a quintessential Vermont country retreat perfectly positioned at the edge of Weston Village with breathtaking Green Mountain views. Embrace the beauty of nature with nearby XC ski trails, snowmobiling, and snowshoeing, plus five renowned ski mountains just a short drive away. In summer, Weston comes alive with concerts on the village green, summer

  Lee Brown Four Seasons Sotheby's Int'l Realty

  815 Vermont Route 100, Weston, VT 05161
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  /53

  $849,000

  • 5 Beds
  • 3.5 Baths
  • 2,890 Sq Ft

  222 Andover Rd, Ludlow, VT 05149

  Stunning Dream Retreat on 11 Acres Awaits. Welcome to your private oasis nestled on a serene property, just 9 minutes from the Okemo Base Lodge. This exquisite home seamlessly blends modern comfort with rustic charm, offering a spacious layout perfect for families and outdoor enthusiasts alike. As you arrive via the paved driveway, you will immediately appreciate the tranquility this property

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

  222 Andover Rd, Ludlow, VT 05149
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  /41

  $6,950,000

  • 8 Beds
  • 7.5 Baths
  • 10,062 Sq Ft

  3800 Weston-Andover Rd, Andover, VT 05143

  Escape to Moosewalk Lane, a fully furnished and equipped luxury estate in Andover, Vermont, set on 384 acres in the iconic Green Mountains. This one of a kind property offers a rare blend of seclusion, natural beauty, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame construction, the

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  3800 Weston-Andover Rd, Andover, VT 05143
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  /38

  $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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  /60

  $3,350,000

  • 6 Beds
  • 4.5 Baths
  • 5,657 Sq Ft

  400 Ruusunen Rd, Springfield, VT 05156

  Wild Trails Farm offers unparalleled privacy, encompassing 436 acres of natural splendor. At the heart of this retreat is a 5,600+ sq ft lodge that is both luxurious and eco-friendly, powered by solar and geothermal. It features 6 spacious bedrooms, 4.5 bathrooms, a gourmet kitchen with dual dining areas, common rooms, and sauna. The 2-car garage is currently utilized as a yoga studio, but could

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  400 Ruusunen Rd, Springfield, VT 05156
• 

  

  /40

  $1,600,000

  • 3 Beds
  • 2 Baths
  • 3,291 Sq Ft

  265 Depot St, Proctorsville, VT 05153

  Welcome to your new home and business headquarters in Cavendish, Vermont. This expansive property near Okemo Mountain Resort blends residential comfort and commercial opportunity. Imagine a chef’s dream kitchen with double ovens, refrigerators, and cooktops, perfect for culinary creativity. The home features three large bedrooms, spacious living areas, and a large deck for relaxation and

  Daire Gibney Barrett and Valley Associates Inc.

  265 Depot St, Proctorsville, VT 05153
• 

  

  /36

  $846,000

  • 3 Beds
  • 3.5 Baths
  • 1,840 Sq Ft

  49 Vt Rt 12, Pomfret, VT 05053

  Discover the possibilities with this beautifully crafted three bedroom, three and one half bath home and versatile Post and Beam barn/studio, set between Woodstock and Silver Lake in scenic Barnard. The main residence features an airy great room with vaulted ceilings, warm wood accents, and expansive windows that invite natural light and frame peaceful views. Thoughtful design and quality

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  49 Vt Rt 12, Pomfret, VT 05053
• 

  

  /37

  $739,000

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

  224 Okemo Trailside Extension Unit 46 C, Ludlow, VT 05149

  Sitting atop the Okemo Trailside community just below the Catnap ski trail and abutting the Okemo State Forest. Three bedroom plus family room townhome offering magnificent panoramic mountain views to the east. Large and well equipped kitchen with vaulted ceiling and breakfast bar. Open dining and living areas centered by a woodburning fireplace with cathedral ceilings leading out to a large

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

  224 Okemo Trailside Extension Unit 46 C, Ludlow, VT 05149
• 

  

  /21

  $480,000

  • 2 Beds
  • 2 Baths
  • 1,178 Sq Ft

  145 Okemo Trailside Extension Unit 23C, upper, Ludlow, VT 05149

  Walk to the Sachem Trail from this recently remodeled, warm and charming, 2 bedroom, 2 bath, 2 level condominium. Easy maintenance with an open floor plan (kitchen, dining and living room with wood burning fireplace and slider to the deck). Updates include: new kitchen cabinets, granite countertops, wood plank flooring, carpet, and paint. The new bathrooms have large format tiling and frameless

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

  145 Okemo Trailside Extension Unit 23C, upper, Ludlow, VT 05149

Showing Results 121 - 160, Page 4 of 5