Windsor County VT Homes for Sale

• 

  

  

  /11

  $87,826 New Construction

  • 1 Bed
  • 1 Bath
  • 643 Sq Ft

  23 Cubb Ct, Windsor, VT 05089

  Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

  Kate Barry EXP Realty

  23 Cubb Ct, Windsor, VT 05089
• 

  

  

  /11

  $98,995 New Construction

  • 3 Beds
  • 2 Baths
  • 880 Sq Ft

  84 Cubb Ct, Windsor, VT 05089

  Welcome to 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  84 Cubb Ct, Windsor, VT 05089
• 

  

  

  /15

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  108 Cubb Ct, Windsor, VT 05089

  Welcome to 132 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  108 Cubb Ct, Windsor, VT 05089
• 

  

  

  /16

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  11 Cubb Ct, Windsor, VT 05089

  Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

  Kate Barry EXP Realty

  11 Cubb Ct, Windsor, VT 05089
• 

  

  

  /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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  /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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  /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
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  /41

  $1,495,000

  • 4 Beds
  • 1.5 Baths

  7 Slayton Terrace, Woodstock, VT 05091

  A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

  Keri Cole Williamson Group Sotheby's International Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /49

  $68,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  418 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Top-Floor 1BR/2BA at Jackson Gore – Sleeps 6, Gorgeous Views, Premium Resort AccessExperience the best of slopeside living with this beautifully appointed 1-bedroom, 2-bathroom top-floor unit at Jackson Gore, Okemo Mountain Resort. Perfectly positioned with incredible valley views and a glimpse of the outdoor heated pool, this residence offers both comfort and convenience, just steps from the

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

  418 Qtr I Jackson Gore Inn, Ludlow, VT 05149
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  /39

  $650,000

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

  193 Jackson Gore Unit 840/842, Ludlow, VT 05149

  Discover the perfect balance of comfort, convenience, and stunning valley views in this beautifully appointed 2-bedroom, 3-bathroom residence located in the sought-after Bixby House at Jackson Gore, Okemo Mountain Resort. This spacious and well-designed unit offers an exceptional slopeside experience with direct ski access and all the amenities you need for a relaxing, four-season Vermont

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

  193 Jackson Gore Unit 840/842, Ludlow, VT 05149
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  /60

  $1,500,000

  • 10 Beds
  • 12 Baths
  • 7,153 Sq Ft

  1589 Main St, Cavendish, VT 05142

  Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

  Kevin Barnes William Raveis Real Estate Vermont Properties

  1589 Main St, Cavendish, VT 05142
• 

  

  /19

  $224,000

  • Land
  • 68.5 Acres
  • $3,270 per Acre

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156

  Behold this rare opportunity to own 68 acres of pristine Vermont land located on a quiet, town-maintained dirt road in the peaceful hills of Springfield. This expansive parcel is a dream for outdoor enthusiasts—offering direct access to nature with miles of established trails, a diverse and healthy forest, and abundant wildlife. Bordering the beloved Muckross State Park—over 200 acres of

  Daire Gibney Barrett and Valley Associates Inc.

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156
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  /45

  $739,000

  • 4 Beds
  • 2.5 Baths
  • 2,663 Sq Ft

  490 W Hill Rd, Ludlow, VT 05149

  From mountain views to après-ski soaks in the hot tub, this home delivers the full Vermont lifestyle with ease. Located on one of Ludlow’s most coveted roads, this custom-built mountain retreat offers the perfect blend of quality, comfort, and convenience. Skip the village traffic and drive straight to the base of Okemo in just minutes! Thoughtfully designed and with so much to love, this

  Frank Provance Diamond Realty

  490 W Hill Rd, Ludlow, VT 05149
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  /60

  $4,850,000

  • 5 Beds
  • 6 Baths
  • 9,153 Sq Ft

  476 Salt Ash Rd, Plymouth, VT 05056

  Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondacks, known as The Point, and thoughtfully designed to reflect its inviting look and warm, rustic elegance. This 9,000+ square foot residence sits atop a knoll beside a lively creek with small waterfalls, creating a peaceful, natural soundtrack.The Great Room is the centerpiece of the home, with a soaring

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  476 Salt Ash Rd, Plymouth, VT 05056
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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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  /44

  $519,000

  • 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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  /41

  $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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  /60

  $2,295,000

  • 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
• 

  

  /57

  $1,199,000

  • 5 Beds
  • 4 Baths
  • 3,282 Sq Ft

  1873 North Rd, Bethel, VT 05032

  On the west-facing ridge of Barnard, Vermont’s fabled North Road, this ca. 1982 Cape enjoys panoramic long-range views of the Green Mountain Range to the west and North. With ten acres of fenced open pasture and a wood lot, a large, detached barn, and plenty of land to use, the property offers a range of possibilities. Expanded and improved by the current owners over the last 20 years, the house

  Richard Higgerson Higgerson & Company

  1873 North Rd, Bethel, VT 05032
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  /30

  $650,000

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

  3630 Vt Route 103 N, Chester, VT 05143

  Exceptional Investment Opportunity in Chester, VT Discover 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 meticulously

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3630 Vt Route 103 N, Chester, VT 05143
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  /18

  $50,000

  • Land
  • 2.07 Acres
  • $24,155 per Acre

  0 E Ash Rd, Plymouth, VT 05056

  Welcome to Hawk East lot 2-20. This 2.07 acres lot is one of the closest lots to the Hawk Mountain Resort. There is a nice level area in the middle of the property that would make a nice building site. Easy access to Route 100 and only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 E Ash Rd, Plymouth, VT 05056
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  /48

  $6,750,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 5,087 Sq Ft

  412 Skyland Ln, Woodstock, VT 05091

  Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

  Story Jenks LandVest, Inc/Woodstock

  412 Skyland Ln, Woodstock, VT 05091
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  /52

  $2,495,000

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

  248 Gird Lot Rd, Weathersfield, VT 05151

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

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
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  /60

  $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

  $625,000

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

  44 Freeman Rd Unit B2, Cavendish, VT 05153

  Your opportunity to own a coveted ground floor 3br plus loft /3.5ba unit of which only 4 were built out of 54 units. The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. 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

  Joseph Karl William Raveis Real Estate Vermont Properties

  44 Freeman Rd Unit B2, Cavendish, VT 05153
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  /6

  $299,000

  • Land
  • 116.2 Acres
  • $2,573 per Acre

  00 Grout Rd, Weathersfield, VT 05153

  A large private parcel of land located in Cavendish on the Weathersfield line. This 116+- acres is a mix of woods and cleared areas that has beautiful mountain views that can be accessed from Grout road. There is road frontage on scenic vermont route 131 that can access the land with grading. These 2 lot have been surveyed and there are multiple possible building sites. This property is close to

  John Napier TPW Real Estate

  00 Grout Rd, Weathersfield, VT 05153
• 

  

  /15

  $139,900

  • Land
  • 2.58 Acres
  • $54,225 per Acre

  0 Cedar Dr, Ludlow, VT 05149

  Discover the perfect canvas for your dream home on this serene 2.5+/-acre lot, ideally located at the end of a cul-de-sac on Cedar Drive in Ludlow, VT. Nestled in a peaceful subdivision, this wooded parcel offers the privacy, natural beauty, and tranquility that define Vermont living. With power conveniently available at the street, this property is ready for your vision—whether that’s a mountain

  Katherine Burns William Raveis Real Estate Vermont Properties

  0 Cedar Dr, Ludlow, VT 05149
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  /51

  $649,000

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  35 Stevens Rd, Cavendish, VT 05142

  Winter, Spring, Summer or Fall, this is a bit of heaven for the nature lover! Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The back yard has lawn area with room for

  Betty McEnaney Diamond Realty

  35 Stevens Rd, Cavendish, VT 05142
• 

  

  /17

  $825,000

  • Land
  • 150 Acres
  • $5,500 per Acre

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091

  150 acres of recreational paradise! Absolute and total privacy! Enjoy long views of mountain peaks showing criss crossed ski trails, pristine cascading streams with mesmerizing waterfalls over large rock outcroppings, mature woodland which hasn't been logged in over 50 years, a fully equipped camper trailer with propane fired generator for off grid living and even a 4 wheeler outfitted with

  John Wetmore Wetmore Real Estate

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091
• 

  

  /19

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  130 Pleasant St, Cavendish, VT 05142

  This home has served as a primary residence and also as an income-producing rental. While the upper level of this home has three bedrooms, the walk-out lower level of the home has such potential as well.It is currently partially finished and is being used as a family room and for storage. The large deck on the end of the house is perfect for taking in some fresh Vermont air or grilling for

  Tyleen Murray Kelley Real Estate, Inc.

  130 Pleasant St, Cavendish, VT 05142
• 

  

  /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
• 

  

  /36

  $349,000

  • Land
  • 10.56 Acres
  • $33,049 per Acre

  0 Valley View Dr, Ludlow, VT 05149

  Elevate Your Lifestyle at Summit Ridge - Tucked away in a private, gated community just minutes from the slopes of Okemo and our Lakes Region, this homesite is the perfect canvas for your mountain dream home. State wastewater permit for a four-bedroom home is in place. Imagine waking up to panoramic, long-range mountain views in every direction—serenity, space, and stunning scenery, all wrapped

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  0 Valley View Dr, Ludlow, VT 05149
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  /60

  $1,250,000

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

  49 Burton Rd, Weston, VT 05161

  “Meadow & Mountain View” is the Vermont home you’ve been waiting for! Situated just outside of the charming village of Weston, this impressive property offers one of the area’s most delightful and picturesque locations with fantastic views, beautiful grounds, and a warm and welcoming house designed so that you can relax and truly enjoy your Vermont Life. The inviting layout features classic New

  Claudia Harris Mary Mitchell Miller Real Estate

  49 Burton Rd, Weston, VT 05161
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  /60

  $899,000

  • 6 Beds
  • 6 Baths
  • 5,497 Sq Ft

  31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767

  Charming 1900s Village Building, Three Condo Units, One Incredible Opportunity! In the heart of Rochesters picturesque village, this beautifully restored early 1900s building is a rare investment opportunity, offered as a single property with three fully furnished condo units. Perfect for an owner-occupant, a multi-generational retreat, or a savvy investor, this historic gem blends classic New

  Kate Cassidy Four Seasons Sotheby's Int'l Realty

  31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767
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  /60

  $549,000

  • Land
  • 20.2 Acres
  • $27,178 per Acre

  00 Long Hill Rd, Woodstock, VT 05071

  Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west. Located just minutes from South

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  00 Long Hill Rd, Woodstock, VT 05071
• 

  

  /11

  $135,000

  • Land
  • 1.19 Acres
  • $113,445 per Acre

  5417 Fletcher Ln, Hartford, VT 05059

  Located in the highly desirable Upper Willard Road neighborhood of Quechee Lakes, this 1.19-acre parcel offers an excellent opportunity to build your Vermont retreat in one of the region’s premier four-season communities. The gently sloping terrain provides flexibility for a homesite, either closer to Fletcher Lane or further back at a higher elevation toward the west end of the property. Recent

  Richard Higgerson Higgerson & Company

  5417 Fletcher Ln, Hartford, VT 05059
• 

  

  /41

  $269,000

  • 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
• 

  

  /25

  $115,000

  • Land
  • 10 Acres
  • $11,500 per Acre

  S-1C Great Roaring Brook Rd, Plymouth, VT 05056

  Ten-acre wooded parcel with potential views located near the top of Great Roaring Brook Rd. The topography is rolling too steep with multiple buildings sites, rock crop outs, and streams throughout. A wonderful opportunity to design and build your Vermont dream home. Located between Ludlow and Woodstock with equal distance to Killington and Okemo Ski areas. Close to Lake Rescue and Echo Lake for

  Terry Davis Williamson Group Sothebys Intl. Realty

  S-1C Great Roaring Brook Rd, Plymouth, VT 05056
• 

  

  /6

  $195,000

  • Land
  • 1 Acre
  • $195,000 per Acre

  Lot 48 Partridge Rd, Ludlow, VT 05149

  1.01+/- acres. Lot 48. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

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

  Lot 48 Partridge Rd, Ludlow, VT 05149

Showing Results 321 - 360, Page 9 of 10