Windsor County VT 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
• 

  

  

  /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
• 

  

  

  /44

  $549,000

  • 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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  /42

  $859,000

  • 5 Beds
  • 4 Baths
  • 4,925 Sq Ft

  1166 Rte 100, Weston, VT 05161

  Nearly 5,000 sq ft of flexible living space in one of Vermont’s most desirable towns—perfect for second-home buyers or investors. This unique property offers two distinct living areas under one roof: a beautifully designed walk-out lower level apartment ideal for rental income, in-law suite, or guest quarters, and an updated main level with style and comfort. The main level features a modern

  Carrie Mathews Winhall Real Estate

  1166 Rte 100, Weston, VT 05161
• 

  

  

  /35

  $998,000

  • Land
  • 9.01 Acres
  • $110,766 per Acre

  0 Newton Ln Unit 5045705, Norwich, VT 05055

  110 Acres of Pastoral Beauty with Mountain Views in Hartford and Norwich, Vermont. This rare 110-acre parcel, 101 acres in Hartford and nine in Norwich (see separate MLS listing 5045699), offers rolling meadows, mature hardwoods, and long mountain views in the heart of the Upper Valley. The elevated, west-facing setting is filled with natural light and classic Vermont charm, with open pastures

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  0 Newton Ln Unit 5045705, Norwich, VT 05055
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  /35

  $998,000

  • Land
  • 101 Acres
  • $9,881 per Acre

  0 Newton Ln Unit 3 5045699, Hartford, VT 05001

  110 Acres of Pastoral Beauty with Mountain Views in Hartford and Norwich, Vermont. This rare 110-acre parcel, 101 acres in Hartford and nine in Norwich (see separate MLS listing #5045705), offers rolling meadows, mature hardwoods, and long mountain views in the heart of the Upper Valley. The elevated, west-facing setting is filled with natural light and classic Vermont charm, with open pastures

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  0 Newton Ln Unit 3 5045699, Hartford, VT 05001
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  /41

  $845,000

  • 2 Beds
  • 1.5 Baths
  • 1,714 Sq Ft

  403 Horse Shoe Way, Woodstock, VT 05071

  Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  403 Horse Shoe Way, Woodstock, VT 05071
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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

  $2,495,000

  • 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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  /57

  $1,249,000

  • 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
• 

  

  /16

  $399,000

  • Land
  • 13.4 Acres
  • $29,776 per Acre

  00 N Hill Pent Rd, Ludlow, VT 05149

  Opportunity awaits with these two connected wooded building lots totaling 13.44 acres, offering easy access to the VAST snowmobile trail network. Located on a quiet, dead-end country road, this peaceful setting is ideal for those seeking a private getaway with four-season recreational opportunities right at your doorstep. Lot A is 4.67 acres and lot B is 8.77 acres. Both parcels include

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  00 N Hill Pent Rd, Ludlow, VT 05149
• 

  

  /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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  /55

  $915,000

  • 3 Beds
  • 3 Baths
  • 2,150 Sq Ft

  509 Church Hill Rd, Wood Stock, VT 05091

  Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

  Carol Wood Williamson Group Sothebys Intl. Realty

  509 Church Hill Rd, Wood Stock, VT 05091
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  /21

  $15,000

  • Land
  • 1.05 Acres
  • $14,286 per Acre

  0 Vermont Route 100, Plymouth, VT 05056

  Discover one of the most affordable ways to get into the Hawk Mountain Resort community. This parcel is located off scenic byway Route 100 and is 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 permits must be approved by the Hawk Architectural Review Board. No trailers, yurts, RV's

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Vermont Route 100, Plymouth, VT 05056
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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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  /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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  /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 65 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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  /59

  $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 kitchen is

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
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  /33

  $3,945,000

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

  5685 Vermont 12, Barnard, VT 05031

  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 property, from the red barn to the mature apple orchard and sugar maples - your eyes will be

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
• 

  

  /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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  /11

  $85,000

  • Land
  • 15.68 Acres
  • $5,421 per Acre

  00 E Hill Rd, Andover, VT 05143

  Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

  Daire Gibney Barrett and Valley Associates Inc.

  00 E Hill Rd, Andover, VT 05143
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  /20

  $250,000

  • Land
  • 28.5 Acres
  • $8,772 per Acre

  00 Chapel Hill Rd, Sharon, VT 05065

  Located on a class IV road, right after the end of the publicly maintained section of Chapel Hill Road, this 28.5 acre parcel has potential for a camp, off-grid home, or as a recreational getaway. The Seller has roughed in a driveway to a level spot about 600 feet from the town maintained road. Build here or clear at the top of the land for incredible views of Mt. Ascutney, Killington, and

  Tami Sullivan Snyder Donegan Real Estate Group

  00 Chapel Hill Rd, Sharon, VT 05065
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  /19

  $695,000

  • Land
  • 60.57 Acres
  • $11,474 per Acre

  0 Noah Wood Rd, Woodstock, VT 05071

  Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

  Dan Noble Snyder Donegan Real Estate Group

  0 Noah Wood Rd, Woodstock, VT 05071
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  /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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  /43

  $750,000

  • 2 Beds
  • 3 Baths
  • 1,364 Sq Ft

  193 Jackson Gore Unit 739/741, Ludlow, VT 05149

  Come and experience Vermont at its best! This condo is located in Jackson Gore on Okemo Mountain in Ludlow. This slope side condo unit has stunning views of the mountain and trails. This unit would serve well as a family retreat or rental investment property. It boasts a gas fireplace for cold winter nights. It has 2 bedrooms and 3 bathrooms and offers lock-out capability for separate rental

  John Napier TPW Real Estate

  193 Jackson Gore Unit 739/741, Ludlow, VT 05149
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  /51

  $674,000

  • 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

  $835,000

  • Land
  • 150 Acres
  • $5,567 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
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  /47

  $8,000,000

  • 3 Beds
  • 3.5 Baths
  • 5,384 Sq Ft

  115 Eastman Rd, Woodstock, VT 05091

  Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

  Keri Cole Williamson Group Sothebys Intl. Realty

  115 Eastman Rd, Woodstock, VT 05091
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  /46

  $1,325,000

  • 4 Beds
  • 2 Baths
  • 2,554 Sq Ft

  325 Cemetery Rd, West Windsor, VT 05089

  Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide

  Story Jenks LandVest, Inc/Woodstock

  325 Cemetery Rd, West Windsor, VT 05089
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  /47

  $625,000

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

  193 Jackson Gore Unit 640/642, Ludlow, VT 05149

  Bixby House 640/642 Whole Ownership. This luxury two-bedroom, valley side home features fully-equipped kitchen with stainless steel appliances, tiled back splash, farm sink and granite counters. The cozy living room includes a dining area and gas fireplace. The tiled foyer entry provides storage for outdoor gear. Primary bedroom has a king bed and a spacious master bath with his and her sinks.

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

  193 Jackson Gore Unit 640/642, Ludlow, VT 05149
• 

  

  /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
• 

  

  /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
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  /49

  $319,000

  • 3 Beds
  • 3 Baths
  • 1,932 Sq Ft

  5 Church St, North Springfield, VT 05150

  Nicely maintained 3BR/3BA ranch home just waiting for a new family. This home features large, updated eat-in kitchen with sliders to a deck, main floor laundry, gas fireplace, home office/den, partially finished basement has a 3/4 bath, workshop area, partially finished rooms that could be additional bedrooms and a large partially finished area for family room. Primary bedroom with bath and lots

  

  Julie Buffum

  Buffum Realty

  (802) 520-0294

  5 Church St, North Springfield, VT 05150
• 

  

  /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
• 

  

  /7

  $84,900

  • Land
  • 1.9 Acres
  • $44,684 per Acre

  276 Dutton District Rd, Springfield, VT 05156

  Idyllic Vermont Land for Sale. Discover the perfect blend of privacy and potential on this serene Vermont parcel, offering a rare opportunity to build your dream home or retreat in the heart of New England. Nestled on a mostly wooded parcel, this lot features a cleared build site, making it ready for immediate development. Infrastructure is already in place with a septic system and a private well

  Chris Benoit Highland Realty

  276 Dutton District Rd, Springfield, VT 05156
• 

  

  /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. Imagine waking up to panoramic, long-range mountain views in every direction—serenity, space, and stunning scenery, all wrapped into one unbeatable location with 10.56 acres. You're just a

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  0 Valley View Dr, Ludlow, VT 05149
• 

  

  /37

  $74,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  228/230 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Great location! This one bedroom lockout unit with a deck is looking right over the outdoor pool and hot tubs with a beautiful valley view! Direct access to the elevator/stairs to the private owner's locker room where you store your skis in your personal locker. Unit C Features: 1 bedroom, sleeps eight, lock-out capabilities, 2 fixed Queen beds, Queen sleep sofa, Queen wall bed, full kitchen, 2

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

  228/230 Qtr I Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /27

  $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 could be

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  1300 Mountain Rd, Ludlow, VT 05149

Showing Results 321 - 360, Page 9 of 11