Windsor County VT Homes for Sale

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  /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
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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
• 

  

  

  /55

  $944,999

  • 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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  /32

  $275,000

  • 6 Beds
  • 2 Baths
  • 2,518 Sq Ft

  761 Main St, Cavendish, VT 05153

  Location, Location, Location...Large families and investors take note. This classic colonial located on the corner of Main Street and Twenty Mile Stream Road is ready for the next family to enjoy or use for rental income. This was the family's gathering house for 55 years, and now it could be yours. There are 6 bedrooms, a woodstove/fireplace, mudroom, 1 car garage/workshop, and bonus space on

  Kevin Barnes William Raveis Real Estate Vermont Properties

  761 Main St, Cavendish, VT 05153
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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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  /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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  /57

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  2475 Little Hollow Rd, Rochester, VT 05767

  Quintessential VT Mountain Location with privacy & seclusion galore! Surrounded by thousands of acres of locally owned timberland, many abundant recreational opportunities to Mount Cushman and the magnificent Little Hollow recreational area. Absolutely Gorgeous 3 bedroom, 3 bath Modified Cape on 7.1 acres of open and wooded land, that is located at the very end of a Class 3 town maintained road,

  Paul H Rea Rural Vermont Real Estate

  2475 Little Hollow Rd, Rochester, VT 05767
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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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  /44

  $475,000

  • 3 Beds
  • 3 Baths
  • 2,180 Sq Ft

  934 E Ash Rd Unit 14, Plymouth, VT 05056

  Charming Condominium Retreat!Welcome to your dream escape nestled amid breathtaking natural beauty in a 1,200-acre private resort community designed by the renowned architectural firm Robert Carl Williams Associates. This stunning condominium is one of only three duplex buildings and offers an ideal blend of modern comfort and serene surroundings. Step inside to an updated kitchen with

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

  934 E Ash Rd Unit 14, Plymouth, VT 05056
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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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  /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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  /6

  $289,000

  • Land
  • 116.2 Acres
  • $2,487 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

  John Napier TPW Real Estate

  00 Grout Rd, Weathersfield, VT 05153
• 

  

  /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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  /37

  $699,000

  • Land
  • 52.3 Acres
  • $13,365 per Acre

  00 Granite Ledge, Pomfret, VT 05059

  Pristine Pomfret land with view of Ascutney! Build your dream home on this unspoiled parcel in one of Pomfret's most beautifully preserved and scenic locales. Surrounded by large landholdings and conserved farmland, but only ten minutes from Woodstock and with excellent access to Route 4 and Quechee, this land comprises historic rock walls, mature hardwoods, a stream, and offers the potential for

  Keri Cole Williamson Group Sothebys Intl. Realty

  00 Granite Ledge, Pomfret, VT 05059
• 

  

  /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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  /48

  $4,900,000

  • 7 Beds
  • 9 Baths
  • 9,464 Sq Ft

  5893 Stage Rd, Barnard, VT 05031

  "LONG WAY HILL" - An elegant and beautifully constructed residence of the highest quality, privately situated on 54 acres with long-range views, lawns, gardens, fields and trails. Beautiful perennial and wildflower gardens offer charming, private views of woods and hills over a half-acre pond. Architect-designed in the style of a traditional New England country home, the main residence has 5

  John Snyder Snyder Donegan Real Estate Group

  5893 Stage Rd, Barnard, VT 05031
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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
• 

  

  /3

  $15,000

  • Land
  • 1.39 Acres
  • $10,791 per Acre

  00 Salt Ash Rd, Plymouth, VT 05056

  Escape to Serenity: Your Dream Vacant Land Awaits!Welcome to a slice of paradise where nature’s beauty meets boundless potential! Nestled in an excellent location, this 1.39-acre vacant land is your blank canvas, ready to become the sanctuary you’ve always envisioned. Imagine waking up surrounded by the whispers of nature, with the promise of stunning potential views waiting just beyond

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

  00 Salt Ash Rd, Plymouth, VT 05056
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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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  /55

  $649,000

  • 3 Beds
  • 3.5 Baths
  • 3,240 Sq Ft

  149 Arnold Rd, Bethel, VT 05032

  PRICE IMPROVEMENT-Motivated Seller!Charming Country Log Home on 35 Private AcresOffered for the first time on the market, this beautifully crafted 2012 log home offers the perfect blend of rustic charm and modern comfort. Thoughtfully designed, the home features 3 spacious bedrooms and 4 bathrooms, with flexible layout options to suit your lifestyle. Two generously sized bedrooms on the

  Eric Kenyon Rural Vermont Real Estate

  149 Arnold Rd, Bethel, VT 05032
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  /51

  $695,000

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

  35 Stevens Rd, Cavendish, VT 05142

  This is a dream come true for someone who is seeking a Vermont nature retreat in every season. 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 views of Mother Nature

  Betty McEnaney Diamond Realty

  35 Stevens Rd, Cavendish, VT 05142
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  /5

  $80,000

  • Land
  • 4.3 Acres
  • $18,605 per Acre

  00 N Hill Rd, Andover, VT 05143

  The first step in building your Vermont Dream home is finding the perfect piece of land. Look no further! Situated on quiet country road of North Hill this parcel offers great building site, quiet location, easy access to skiing at Vail/Okemo resort (only minutes away), VAST access, close to Weston village with the Vermont Country Store and the Weston Playhouse. Soil tests were conducted years

  Lisa Kelley Cummings & Co

  00 N Hill Rd, Andover, VT 05143
• 

  

  /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
• 

  

  /21

  $290,000

  • Land
  • 30.35 Acres
  • $9,555 per Acre

  00 Chapel Hill Rd, Sharon, VT 05065

  Located at the end of publicly maintained Chapel Hill Road, this lot consists of 20.85 acres in Sharon and 9.5 acres in Norwich. A woods road or future driveway leads to the height of land with unparalleled panoramic, southwesterly views of Mt. Ascutney, Killington, and beyond. There is no power on this section of Chapel Hill Rd., but the lot would be perfect for a solar home, camp, or just a

  Tami Sullivan Snyder Donegan Real Estate Group

  00 Chapel Hill Rd, Sharon, VT 05065
• 

  

  /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
• 

  

  /23

  $99,995

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  133 Willow Cir, White River Junction, VT 05001

  An affordable 3-bedroom 2-bath double-wide home in one of the Upper Valley’s most sought-after parks, Tall Timbers. One Car garage, lots of storage and more. This home offers laminate flooring, spacious kitchen and laundry area. One of the best lots available with plenty of space, you’ll feel like you live on your own land. The surrounding homes are in great condition and with a little TLC

  Richard Ballou RE/MAX Upper Valley

  133 Willow Cir, White River Junction, VT 05001
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  /46

  $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
• 

  

  /45

  $199,900

  • 2 Beds
  • 1 Bath
  • 2,250 Sq Ft

  5755 Us Route 5, Weathersfield, VT 05030

  New improved price for a Buyer $199,999 Ideal for conversion into a spacious single-family home or potentially a duplex.Open floor plan with soaring ceilings and wood flooring throughout. The structure includes a full bathroom, a partial kitchen, and the framework for two bedrooms— New hot air heating oil system install fall 2024 The building was officially approved for residential use in 2023.

  Deb Roberts RE/MAX Upper Valley

  5755 Us Route 5, Weathersfield, VT 05030
• 

  

  /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

Showing Results 361 - 400, Page 10 of 13