Windsor County VT Homes for Sale

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  /11

  $249,000

  • Land
  • 57.2 Acres
  • $4,353 per Acre

  0 Masterson Unit 5080891, Barnard, VT 05031

  Discover 57.2 acres of exceptional forestland offering the perfect blend of privacy and convenience—tucked away yet less than half a mile from Vermont Route 12. This property provides an ideal setting for a private home or recreational retreat, with easy access to Barnard Village and Interstate 89. The recently cleared build site sits in a wonderful location above, yet not too far from Masterson

  Sophie Roya Berry Hill Real Estate

  0 Masterson Unit 5080891, Barnard, VT 05031
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  /19

  $27,500

  • Land
  • 1.98 Acres
  • $13,889 per Acre

  2-47 E Ash Rd, Plymouth, VT 05056

  Nice building lot within Hawk Resort. Some flat areas with potential westerly views. Electric and high speed internet is at street and there is the option to hook into community septic. Nestled in the scenic lakes region, halfway between Killington and Okemo, Hawk offers a prime location for outdoor enthusiasts. Whether you're hitting the slopes, exploring the trails, or simply enjoying the

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  2-47 E Ash Rd, Plymouth, VT 05056
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  /60

  $200,000

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

  00 Vermont 103, Andover, VT 05143

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

  Rachael Lange Lange & Lange

  00 Vermont 103, Andover, VT 05143
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  /23

  $750,000

  • Land
  • 2.07 Acres
  • $362,319 per Acre

  Lot 1 Timber Creek Rd, Ludlow, VT 05149

  Timber Creek on Okemo offers a rare opportunity to build in one of Okemo’s premier on-mountain communities. This residential lot is ideally located with easy access to SouthFace Village, giving owners the ability to enjoy the sunny side of the mountain with convenient slope access and year-round resort-style amenities.Ownership includes access to SouthFace Village amenities, including a ski

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  Lot 1 Timber Creek Rd, Ludlow, VT 05149
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  /18

  $299,900

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

  105 Williams Ln Unit C, Quechee, VT 05059

  Adorable and well maintained 2 bedroom with loft and 1.5 bathroom condo located on top of the Quechee Ski Hill. Very short walk to the ski trail from your front door. The condo is fully furnished and "turn key". The owners only plan to take some small personal belongings and some artwork. Recent improvements include new gas fireplace, new stackable washer/dryer, new hot water heater and new bed

  Shane Vahey New England Real Estate Advisors, LLC

  105 Williams Ln Unit C, Quechee, VT 05059
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  /48

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 1,558 Sq Ft

  501 Stoughton Pond Rd, Perkinsville, VT 05151

  Tucked into the charming village of Perkinsville on 3.8 acres, this unique residential and commercial property offers the perfect balance of opportunity, lifestyle, and connection. You will be moments away from Stoughton Pond, hiking trails, and within driving distance to some of Vermont’s most sought-after ski resorts. For years, this property has been a gathering place—Saturday nights around

  Marie Potter EXP Realty

  501 Stoughton Pond Rd, Perkinsville, 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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  /31

  $324,000

  • 1 Bed
  • 1 Bath
  • 599 Sq Ft

  350 Mountain Rd Unit B303, Ludlow, VT 05149

  Fabulous ski-in/ski-out opportunity at the base of Okemo Mountain! This top-floor (3rd level) one-bedroom, one-bath condominium offers unbeatable convenience and beautiful views overlooking the Okemo Base Lodge and the A-B chair lifts. With a sleeper sofa for additional guests, it’s the perfect Vermont retreat for weekend getaways or extended stays. A new electric fireplace provides ambiance and

  McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  350 Mountain Rd Unit B303, Ludlow, VT 05149
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  /39

  $849,000

  • 4 Beds
  • 4 Baths
  • 2,534 Sq Ft

  732 Bridgewater Center Rd, Bridgewater Corners, VT 05035

  Turn-key mountain retreat just minutes from Killington or Woodstock! Completely renovated 4-bedroom, 4-bath home blends modern updates with classic Vermont character - featuring an updated kitchen, new bathrooms, a large mudroom with built-in ski storage, and scenic mountain views showcased by oversized custom windows that fill the home with natural light. Multiple living spaces and the expansive

  Alex Shaffer Four Corner Properties LLC

  732 Bridgewater Center Rd, Bridgewater Corners, VT 05035
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  /47

  $550,000

  • 3 Beds
  • 4 Baths
  • 2,727 Sq Ft

  1787 Route 100 N, Ludlow, VT 05149

  From location to layout, this home offers the best of Vermont living. Set along scenic Route 100 in the heart of the lakes region, you’ll enjoy year-round recreation just minutes from Okemo Mountain Resort, Killington Resort, and Plymouth State Park. This thoughtfully remodeled farmhouse blends classic charm with modern updates. Offering 3 bedrooms and 4 bathrooms, the home features generous

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  1787 Route 100 N, Ludlow, VT 05149
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  /10

  $349,000

  • Land
  • 60 Acres
  • $5,817 per Acre

  911 Waterman Rd, Royalton, VT 05068

  Explore the opportunity of this 60 Acre parcel which is beautifully wooded with awesome mountain view potential. Extensive walking trails throughout the land. Possible development options here or build your private dream retreat. VAST Snowmobile Trails run through the property and the backside of the land abuts the Second Branch of the White River. The land has never been percd for septic. Come

  Marni Rieger KW Vermont-Killington

  911 Waterman Rd, Royalton, VT 05068
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  /35

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,312 Sq Ft

  33 Pleasant Street Extension, Ludlow, VT 05149

  Located in the Village Of Ludlow this turn key ranch has been a great second home/investment for the current owner. Situated on the the outskirts of town with a classic neighborhood feel and the comfort of locals nearby. Take in the Okemo views as soon as you set foot on the property with ample parking for guests in the circular driveway. Step into the recently renovated house to include windows,

  Frank Provance Diamond Realty

  33 Pleasant Street Extension, Ludlow, VT 05149
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  /52

  $499,000

  • 7 Beds
  • 4 Baths
  • 2,262 Sq Ft

  157 Summer St, Hartford, VT 05001

  Investors take notice! This is a newly vacant, turn-key, two-unit multifamily property that will be ready to rent on day one! The first floor unit boasts four bedrooms, two bathrooms, and plenty of space and storage to spread out. The upstairs unit has three bedrooms, two bathrooms, and comes with a walk-out balcony overlooking Summer Street. Each unit has its own access and will be easy to rent.

  Sal Cania BHHS Verani Upper Valley

  157 Summer St, Hartford, VT 05001
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  /43

  $699,000

  • 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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  /30

  $435,000

  • 3 Beds
  • 1.5 Baths
  • 1,494 Sq Ft

  44 Acorn St, White River Junction, VT 05001

  This 3 bedroom, 2 bath saltbox is located in a desirable neighborhood right near downtown White River Junction where there are many restaurants, stores, and the famous Northern Stage theater. This home features an open concept kitchen and living space with gas fireplace for chilly nights. Upstairs there are 3 bedrooms and 1 full bath with an open light filled hallway. In the basement there is a

  Heidi Reiss Coldwell Banker LIFESTYLES - Hanover

  44 Acorn St, White River Junction, VT 05001
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  /9

  $129,000

  • Land
  • 7.95 Acres
  • $16,226 per Acre

  0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

  Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

  Thaddeus Abare Barrett and Valley Associates Inc.

  0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
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  /20

  $169,000

  • 1 Bed
  • 1 Bath
  • 200 Sq Ft

  3019 Popple Dungeon Rd, Chester, VT 05143

  Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3019 Popple Dungeon Rd, Chester, VT 05143
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  /60

  $1,300,000

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft

  366 Knapp Pond Rd, Cavendish, VT 05142

  Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances,

  Franchesca Collins Hall Collins Real Estate Group

  366 Knapp Pond Rd, Cavendish, VT 05142
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  /19

  $95,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  1500 Brownsville-Hartland Rd, West Windsor, VT 05089

  Here's a chance to own your own property in West Windsor. This 3/4 +/- acre of land abuts one side up to Beaver Brook and you get views of Mt. Ascutney on the other side. This older mobile home with basement, offers the perfect opportunity for an investor. Restore the homes vintage charm or you could modernize the site with a new mobile unit. This was constructed as a 2-bedroom 1 bath home. One

  Ann Jacques Century 21 Highview Realty

  1500 Brownsville-Hartland Rd, West Windsor, VT 05089
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  /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
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  /60

  $115,000

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

  00 Vt Route 103 N, Chester, VT 05143

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

  Rachael Lange Lange & Lange

  00 Vt Route 103 N, Chester, VT 05143
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  /42

  $699,900

  • 3 Beds
  • 1.5 Baths
  • 1,938 Sq Ft

  4205 Vermont 131, Weathersfield, VT 05151

  Step into timeless New England charm with this historic circa-1760s expanded Cape, offering a wonderful blend of early craftsmanship, character, and modern-day livability. The home showcases classic timber frame construction with hand hewn beams, beautiful wide plank floors, and preserved period details that create warmth and authenticity throughout every room. With three bedrooms and two full

  Thaddeus Abare Barrett and Valley Associates Inc.

  4205 Vermont 131, Weathersfield, VT 05151
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  /16

  $1,675,000 New Construction

  • 5 Beds
  • 3 Baths
  • 3,837 Sq Ft

  4071 Tichnor Rd Unit 4071, Hartford, VT 05001

  The Walnut at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Walnut offers 3,837 square feet of beautifully appointed living space across three levels, paired with a detached two-car garage. The main level centers on a great room that combines the kitchen, dining area, and living room into one expansive, light-filled space with soaring cathedral ceilings, a wood-burning

  Richard Higgerson Higgerson & Company

  4071 Tichnor Rd Unit 4071, Hartford, VT 05001
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  /60

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  547 Williams Rd, Chester, VT 05143

  Welcome to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, yet close to skiing, VAST and amenities. So many updates in the past two years, modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is

  Terri Edgerley Edge Realty Vermont

  547 Williams Rd, Chester, VT 05143
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  /19

  $284,500

  • Land
  • 10.01 Acres
  • $28,422 per Acre

  713 S Hill Rd, Ludlow, VT 05149

  This is not your typical 10 acre parcel! The critical infrastructure elements: a new fully installed 5-bedroom septic system, a drilled well and underground electricity already on the property. Plus, there's a gravel driveway that makes accessing your future home a breeze. This 10 acre parcel is just waiting for your home plans. Approx. 3 miles from Ludlow's Main St. via a year round maintained

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

  713 S Hill Rd, Ludlow, VT 05149
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  /49

  $63,000

  • 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
• 

  

  /23

  $125,000

  • Land
  • 10.3 Acres
  • $12,136 per Acre

  167 Leons Ln, Sharon, VT 05068

  Discover a rare development opportunity tucked away in the Vermont woods. Situated on a quiet, dead-end road, this stunning 10+ acre parcel offers the perfect canvas for your dream mountain sanctuary. The land features a serene mix of deciduous and evergreen trees and slopes upward, offering excellent potential for a home with a walk-out basement. While a rustic cabin shell currently sits on the

  Holly Hall Hall Collins Real Estate Group

  167 Leons Ln, Sharon, VT 05068
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  /13

  $749,000

  • 11 Beds
  • 6 Baths
  • 6,000 Sq Ft

  23-25 Depot, Ludlow, VT 05149

  Okemo-LudlowUnique commercial property in the center of Ludlow Village. Presently 6 apartment units, plus an 8-bay garage. This property has high visibility and plenty of off-street parking, offering many commercial opportunities. Trustee, seller is a Licensed Real Estate Broker. Siding is asbestos shingle.48 Hours advanced notice needed to show, best times late morning & early afternoon.

  Frank Ellison Ellison Real Estate, Inc.

  23-25 Depot, Ludlow, VT 05149
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  /18

  $74,500

  • Land
  • 16.24 Acres
  • $4,587 per Acre

  TBD Farrar Rd, Chester, VT 05143

  Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

  Erin Kendall EXP Realty

  TBD Farrar Rd, Chester, VT 05143
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  /48

  $769,000

  • 4 Beds
  • 3 Baths
  • 3,179 Sq Ft

  31 Plumley Ave, Ludlow, VT 05149

  Charming Country Retreat in Ludlow – Minutes from Okemo MountainDon’t miss this rare opportunity to enjoy the peace of country living in the heart of Ludlow, a quintessential Vermont ski town and home to Okemo Mountain Resort. This meticulously maintained home has been lovingly cared for by the same owner for over 30 years. Designed for easy living, this move-in-ready property features

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

  31 Plumley Ave, Ludlow, VT 05149
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  /35

  $350,000

  • 1 Bed
  • 1 Bath
  • 599 Sq Ft

  318 Mountain Rd Unit A-304, Ludlow, VT 05149

  Okemo Mountain Lodge, come experience unbeatable convenience, ideally located at the base of Okemo Mountain Resort. This one-bedroom residence offers the ease of ownership with true ski-in/ski-out access. Easy access to the main base area, where ski services, lifts, dining, and après-ski options are all right outside your door. The unit comfortably sleeps four, making it perfect for personal

  Katherine Burns William Raveis Real Estate Vermont Properties

  318 Mountain Rd Unit A-304, Ludlow, VT 05149
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  /59

  $930,000

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  567 Churchill Rd, Brownsville, VT 05037

  Discover a truly rare opportunity to own an extraordinary piece of Vermont countryside. This 4-bedroom, 3-bath home is set on 80 acres of pristine woodland with nearly a full mile of road frontage for exceptional accessibility and future potential. Lovingly held by the same family for over 60 years, the property is rich in history, with classic stone wall boundary lines that echo its past. This

  Julie Davis KW Vermont Woodstock

  567 Churchill Rd, Brownsville, VT 05037
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  /47

  $539,000

  • 4 Beds
  • 3.5 Baths
  • 2,436 Sq Ft

  879 E Ash Rd Unit 5, Plymouth, VT 05056

  Rare opportunity to own one of the largest townhomes at Hawk Resort! This exceptional four-bedroom, 3.5-bath end unit at Hawk Ledges is perched atop East Ash Road, offering privacy, space, and a true Vermont retreat experience.Spanning four thoughtfully designed levels, the home provides wonderful separation of space for family and guests alike. Multiple cozy living and entertainment areas

  McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  879 E Ash Rd Unit 5, Plymouth, VT 05056
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  /32

  $279,000

  • Land
  • 10.2 Acres
  • $27,353 per Acre

  00 Parker Ln, Weston, VT 05161

  Morning light spills across the meadow, the pond reflects the changing sky, and the Green Mountains rise in the distance. Set on 10.2 acres along a quiet country road near Weston Village, this exceptional parcel offers the rare opportunity to create a Vermont home deeply connected to both landscape and lifestyle. Much of the groundwork has already been completed, including a state-approved

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  00 Parker Ln, Weston, VT 05161
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  /43

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,697 Sq Ft

  818 Main St, Cavendish, VT 05153

  Opportunity meets flexibility at this charming two-unit property in the heart of Proctorsville. Ideal for an owner who wants a vacation getaway with built-in income potential — or as an easy, turnkey investment — this well-kept duplex offers multiple paths to ownership. The downstairs unit features a three-season porch/mudroom entry, two bedrooms, an open-concept living, dining area, and kitchen,

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  818 Main St, Cavendish, VT 05153
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  /16

  $250,000

  • 5 Beds
  • 2 Baths
  • 1,728 Sq Ft

  101 Mount Vernon St, Springfield, VT 05156

  Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect one

  Christine Lewis Brattleboro Area Realty

  101 Mount Vernon St, Springfield, VT 05156
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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
• 

  

  /31

  $279,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  436 Mount View Loop, Rochester, VT 05767

  Tucked away in the peaceful woods of Rochester, this quaint three bedroom, one and a half bath home offers the perfect blend of privacy and outdoor adventure. Surrounded by nature, the property provides a true rural retreat while still being part of a vibrant, recreation-rich community. This home is a gateway to year-round recreation. Enjoy the tranquility of your wooded surroundings or take

  Lisa Marie Sargent Champlain Valley Properties

  436 Mount View Loop, Rochester, VT 05767
• 

  

  /41

  $4,250,000

  • 7 Beds
  • 9 Baths
  • 9,615 Sq Ft

  5893 Stage Rd, Barnard, VT 05031

  Set on 54 exceptionally private acres, Long Way Hill is a a quietly luxurious Vermont country retreat overlooking a half-acre pond, with sweeping lawns, gardens, fields, and woodland trails. It is located minutes from Silver Lake and Twin Farms, and 15 minutes from Woodstock. Designed by David Beilman and built by Savelberg Construction in 2006, the home is defined by its high

  Story Jenks LandVest, Inc/Woodstock

  5893 Stage Rd, Barnard, VT 05031
• 

  

  /31

  $646,500

  • Land
  • 37.85 Acres
  • $17,081 per Acre

  0 South Rd, Woodstock, VT 05071

  Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream.About two miles to GMHA and South Woodstock village, one mile to VAST trail.40 minutes to skiing at Killington, less to Okemos. Seven miles into Woodstock Village.

  Matthew Spittle Vermont Horse Country Real Estate

  0 South Rd, Woodstock, VT 05071

Showing Results 161 - 200, Page 5 of 11