Windham County VT Houses for Sale

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  /55

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,512 Sq Ft

  40 Ellis Brook Rd, West Dover, VT 05356

  Welcome to the beloved "Papa's Blue House," a cherished family home since its construction in 1968. Nestled in the desirable Dover Hills section of Dover, VT, this property offers the perfect blend of charm and potential. With good bones and a generous layout, it’s an ideal canvas for creating your dream home. Featuring a spacious open-concept living room, dining room, and kitchen, perfect for

  Donna Brown Skihome Realty

  40 Ellis Brook Rd, West Dover, VT 05356
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  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
• 

  

  

  /41

  $799,000

  • 5 Beds
  • 3 Baths
  • 3,091 Sq Ft

  798 Vermont Route 100, Wilmington, VT 05363

  Multi-Family & Commercial Opportunity in Wilmington, VermontSet on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing.The main building features updated interiors with modern kitchens, stylish baths, and new

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  798 Vermont Route 100, Wilmington, VT 05363
• 

  

  

  /31

  $649,000

  • 5 Beds
  • 3.5 Baths
  • 2,706 Sq Ft

  916 Wiswall Hill Rd, Townshend, VT 05353

  Escape to the peace and beauty of Townshend, Vermont, where this spacious 5-bedroom home offers the perfect blend of privacy, comfort, and craftsmanship. Located on a publicly maintained dead-end road, the property enjoys a quiet, secluded country setting while still providing the reassurance of year-round access. Thoughtfully designed and well-built, the home welcomes you with warmth and

  Mike Masters Four Seasons Sotheby's Int'l Realty

  916 Wiswall Hill Rd, Townshend, VT 05353
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  /35

  $285,000

  • 3 Beds
  • 1.5 Baths
  • 3,096 Sq Ft

  11 Fornuto Rd, Wardsboro, VT 05355

  Opportunity awaits in this unique mixed-use property featuring a street-level restaurant space and a second-floor apartment. Located right in the heart of Wardsboro Village, once home to a local café, the main level still features brand-new commercial kitchen equipment ready for a fresh start. Convenient in-town location with good visibility, also within 10 minutes to Mt. Snow, 20 minutes to

  Jessica Samples BHG Masiello Keene

  11 Fornuto Rd, Wardsboro, VT 05355
• 

  

  /39

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft

  256 Potter Rd, Wardsboro, VT 05355

  Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  256 Potter Rd, Wardsboro, VT 05355
• 

  

  /12

  $399,000 New Construction

  • 4 Beds
  • 2 Baths
  • 3,700 Sq Ft

  442 Mcmillan Rd, Whitingham, VT 05342

  New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three levels.

  Mark Yule BHG Masiello Brattleboro

  442 Mcmillan Rd, Whitingham, VT 05342
• 

  

  /21

  $685,000

  • 4 Beds
  • 2.5 Baths
  • 5,646 Sq Ft

  311 Laurel Ledges, Vernon, VT 05354

  Private 4-bedroom country home on 10.5 acres at the end of the road, located just 10 minutes from Brattleboro. The home offers a spacious layout with a large kitchen featuring a granite island, multiple living areas including a great room with cathedral ceiling and woodstove, separate living room with fireplace, private office, mudroom, first-floor laundry, and an attached 2-car garage. The upper

  Derek Greene Derek Greene

  311 Laurel Ledges, Vernon, VT 05354
• 

  

  /32

  $559,000

  • 3 Beds
  • 3 Baths
  • 2,080 Sq Ft

  9 Greer Ct, Wilmington, VT 05363

  Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9 Greer Ct, Wilmington, VT 05363
• 

  

  /49

  $525,000

  • 4 Beds
  • 3.5 Baths
  • 1,913 Sq Ft

  35 Birch Rd, Londonderry, VT 05148

  Nestled in the heart of Vermont’s ski country, this architect-designed home is a striking blend of whimsical artistry and alpine living. A stones throw from Magic Mountains base lodge, skiing and four-season adventure await right outside your door. Designed by a visionary architect with a love for natural light, the residence offers both artistic flair and multiple finished spaces the whole

  Mendi Michael Engel & Völkers Okemo

  35 Birch Rd, Londonderry, VT 05148
• 

  

  /22

  $329,000

  • 4 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  696 S Wardsboro Rd, Wardsboro, VT 05355

  Priced to Sell. Fabulous Southern Vermont Estate nestled between Mount Snow and Stratton Ski areas! You'll have Wardsboro Brook in your back yard & Grout pond down the street as well as hiking trails, Vast Appalachian Trail (AT) and long Trails. Plenty of back country outdoor experiences available all year round. They say Location is everything, this property has everything and More. Family room

  Kimberly Dubois Matson Keller Williams Realty

  696 S Wardsboro Rd, Wardsboro, VT 05355
• 

  

  /44

  $599,000

  • 4 Beds
  • 4 Baths
  • 4,060 Sq Ft

  141 Piney Brook Way, Brattleboro, VT 05301

  Set on 12 acres of wooded privacy in desirable Marlboro, this spacious and versatile property offers comfort, flexibility, and stunning natural surroundings. The main home features 3 bedrooms, a large family room and first-floor laundry, offering plenty of room for a growing household, guests, or multi-generational living. Cozy up by the wood stove on chilly evenings, and enjoy the peace of mind

  Desiree Stango Berkley & Veller Greenwood Country

  141 Piney Brook Way, Brattleboro, VT 05301
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  /20

  $330,000

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  3730 Route 100, Wardsboro, VT 05355

  Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.Sellers have given permission to encourage all offers. Property was originally listed for $450,000 but the sellers have reduced the price to $350,000. The tax

  Ginny Read Read Realty LTD

  3730 Route 100, Wardsboro, VT 05355
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  /12

  $99,900

  • 3 Beds
  • 2 Baths
  • 2,098 Sq Ft

  843 Kentfield Rd, Whitingham, VT 05361

  Step back in time with this 1865 home, currently used as a two-family residence, which could easily be restored to its original layout. The ceiling beams have been exposed, allowing you to keep their rustic charm or cover them for a more traditional look. The attached barn would be ideal for a studio, workshop, or bonus room, offering numerous options to suit your needs. Many projects are left to

  Linda Benoit Highland Realty

  843 Kentfield Rd, Whitingham, VT 05361
• 

  /2

  $90,000

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft

  93 Clark St, Brattleboro, VT 05301

  An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please,

  Christine Lewis Brattleboro Area Realty

  93 Clark St, Brattleboro, VT 05301
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  /39

  $300,000

  • 4 Beds
  • 1 Bath
  • 1,248 Sq Ft

  552 - 554 Hinesburg Rd, Brattleboro, VT 05301

  Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

  Steve Schoppmeyer BHG Masiello Brattleboro

  552 - 554 Hinesburg Rd, Brattleboro, VT 05301
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  /48

  $644,000

  • 3 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  774 Stratton Arlington Rd, Stratton, VT 05360

  Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  774 Stratton Arlington Rd, Stratton, VT 05360
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  /38

  $520,000

  • 3 Beds
  • 3 Baths
  • 2,040 Sq Ft

  829 Pennel Hill Rd, Halifax, VT 05342

  Spacious cabin set on 16.4 acres with stream and pond. Open main living area features hardwood floors, vaulted ceilings with skylights, exposed beams, and an efficient wood stove. Updated kitchen includes stainless steel appliances and breakfast bar seating.Main level bedroom with shared en suite bathroom featuring claw foot tub and walk-in shower. Spiral staircase leads to primary suite with

  Megan Quinn Southern Vermont Realty Group

  829 Pennel Hill Rd, Halifax, VT 05342
• 

  /2

  $99,900

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft

  321 Williams St, Brattleboro, VT 05301

  Opportunity to live and invest in upgrades for your new home.

  Susan Bellville Bellville Realty

  321 Williams St, Brattleboro, VT 05301
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  /45

  $798,000

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft

  619 Stratton Arlington Rd, West Wardsboro, VT 05360

  Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  619 Stratton Arlington Rd, West Wardsboro, VT 05360
• 

  

  /23

  $3,500,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 7,000 Sq Ft

  29 Mountain Ridge Dr, Wilmington, VT 05363

  The Mountain Ridge community is newly developed and this is the first opportunity to enter this new prestigious location. 38 acres with 5 total lots, including a spectacular newly built luxury Timber Frame home being sold as-is near completion, with a builder on board ready to finish, plus 4 separate gorgeous mountain view building sites. Finish this home with the fixtures and finishes already

  Adam Palmiter Berkley & Veller Greenwood/Dover

  29 Mountain Ridge Dr, Wilmington, VT 05363
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  /36

  $382,000

  • 6 Beds
  • 2.5 Baths
  • 3,590 Sq Ft

  88 Westminster St, Town of Rockingham, VT 05101

  Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 15 rooms, 6 bedrooms and the potential for 4 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period

  Jamie Watson BHG Masiello Keene

  88 Westminster St, Town of Rockingham, VT 05101
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  /34

  $389,900

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft

  295 Stratton Arlington Rd, West Wardsboro, VT 05360

  Beautifully renovated 2-bedroom, 2-bath cottage on 1.9 acres in Stratton. Ideally located just minutes from both Mount Snow and Stratton ski areas, with the Stratton Recreation Center conveniently down the road. Enter through the mudroom into a bright, open-concept kitchen and dining space featuring a cozy woodstove and 4 skylights. The living room is spacious with a mini split and also includes

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  295 Stratton Arlington Rd, West Wardsboro, VT 05360
• 

  

  /44

  $289,900

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  10 King St, Bellows Falls, VT 05101

  Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With

  Floyd Amidon Maple Leaf Realty

  10 King St, Bellows Falls, VT 05101
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  /48

  $380,000

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  183 Bear Hill Rd, Dummerston, VT 05301

  Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency. This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

  Kate Barry EXP Realty

  183 Bear Hill Rd, Dummerston, VT 05301
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  /45

  $1,470,000

  • 5 Beds
  • 4.5 Baths
  • 5,160 Sq Ft

  224 Cobble Ridge Rd, Londonderry, VT 05148

  Perched on scenic Cobble Ridge, this custom five-bedroom, four-and-a-half-bath retreat embodies balance, light, and renewal in the heart of Southern Vermont. Set on seven private, fenced acres framed by stone walls and dual gated entries, the property enjoys southwest exposure with soft, filtered ridgeline views that evolve beautifully through the seasons. Inside, a brick fireplace anchors the

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  224 Cobble Ridge Rd, Londonderry, VT 05148
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  /60

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,782 Sq Ft

  628 Townshend Rd, Grafton, VT 05146

  One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

  Jessica Landers Barrett and Valley Associates Inc.

  628 Townshend Rd, Grafton, VT 05146
• 

  

  /51

  $895,000

  • 3 Beds
  • 4.5 Baths
  • 3,318 Sq Ft

  42 Sugar House Rd, West Dover, VT 05356

  Tucked into the serene hills of Dover, Vermont, this custom crafted mountain home offers the ideal blend of rustic charm and modern comfort just minutes from Mount Snow and The Hermitage Club. Set on a private lot with winter views of both ski mountains, this 3-bedroom(+bonus bedroom), 4.5-bath home features an open-concept layout with soaring cathedral ceilings, exposed beams, and a stunning

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  42 Sugar House Rd, West Dover, VT 05356
• 

  

  /33

  $295,000

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

  70 Overlook Dr, Londonderry, VT 05148

  Located close to town but in a private and quiet area, this property offers an affordable option for locals and first-time homebuyers who want to be in one of Vermont’s best little communities and are willing to make the time and investment to turn this house into a home. The house is solid and has been well-maintained, and there are three bedrooms and 1.5 bathrooms and a nice one-level layout

  Claudia Harris Mary Mitchell Miller Real Estate

  70 Overlook Dr, Londonderry, VT 05148
• 

  

  /3

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  2173 Vermont 8a, Whitingham, VT 05361

  4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

  Mark Yule BHG Masiello Brattleboro

  2173 Vermont 8a, Whitingham, VT 05361
• 

  

  /60

  $1,345,000

  • 3 Beds
  • 3 Baths
  • 2,824 Sq Ft

  135 Fred Houghton Rd, Putney, VT 05346

  This one-of-a-kind Vermont property offers three dwellings on 5.68 acres - each blending elevated aesthetics, thoughtful design, and a true connection to nature. The 2011 main house features an open layout and handcrafted finishes throughout. The kitchen boasts soapstone countertops and custom cherry cabinetry. A very special wood-fired masonry heater anchors the living space and a spacious

  Claire Renaud Berkley & Veller Greenwood Country

  135 Fred Houghton Rd, Putney, VT 05346
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  /34

  $389,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  137 Pleasant Valley Rd, Brattleboro, VT 05301

  This is a rare opportunity to own a piece of Pleasant Valley road in west Brattleboro Vermont. A solid Timberframe, designed and built in 2019 with sustainability and long term affordability as the guiding factors. This 650 square foot home is just enough to provide comfortable living with its high ceiling and extravagant windows, without having to heat and maintain extraneous space. With its

  Christine Lewis Brattleboro Area Realty

  137 Pleasant Valley Rd, Brattleboro, VT 05301
• 

  

  /51

  $879,900

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  7 Yodeling Ln, West Dover, VT 05356

  Charming Log Home with Modern Comfort and Prime Location. This warm and inviting log home offers the perfect blend of rustic charm and modern style. Nestled on a level lot with ample parking, it features a large covered front porch and a spacious rear deck, ideal for enjoying the beautiful outdoors. Step inside to the main level, where you'll find a welcoming living room anchored by a stunning

  Rich Caplan Deerfield Valley Real Estate

  7 Yodeling Ln, West Dover, VT 05356
• 

  

  /40

  $849,000

  • 5 Beds
  • 3.5 Baths
  • 3,436 Sq Ft

  67 Castle Hill Rd, Wilmington, VT 05363

  Rare opportunity to own a meticulous 1830s vintage farmhouse, completely turn-key with extensive updates, renovations, and modern amenities. Conveniently located just outside the country village of Wilmington for shopping and great dining options, a short drive to the Mount Snow ski resort, and just up the street from the Lake Whitingham boat launch and beach areas, for true four season

  Adam Palmiter Berkley & Veller Greenwood/Dover

  67 Castle Hill Rd, Wilmington, VT 05363
• 

  

  /21

  $205,000

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  12 Laurel Ave, Bellows Falls, VT 05101

  Move-in ready and full of charm! This well-maintained, beautifully decorated home offers both comfort and convenience in the heart of Bellows Falls. Set on a corner lot within walking distance to town amenities, it features a generously sized kitchen complete with a beverage station and three upstairs bedrooms, providing plenty of space to fit your needs. The manageable lot requires very little

  Linda Benoit Highland Realty

  12 Laurel Ave, Bellows Falls, VT 05101
• 

  /2

  $325,000

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  292 Deer Hill Rd, Whitingham, VT 05361

  Tucked amongst trees with a great deck. This rural location is not far from great skiing, shopping and all kinds of great dining and entertainment. Over an acre of mostly wooded lot. Property is occupied. No drive by's please..

  Susan Bellville Bellville Realty

  292 Deer Hill Rd, Whitingham, VT 05361
• 

  

  /34

  $699,000

  • 3 Beds
  • 4 Baths
  • 3,796 Sq Ft

  233 Poverty Row, Whitingham, VT 05361

  What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, beautiful

  Adam Palmiter Berkley & Veller Greenwood/Dover

  233 Poverty Row, Whitingham, VT 05361
• 

  

  /45

  $274,900

  • 4 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  49 Clark Ave, Brattleboro, VT 05301

  Set in a fantastic, highly sought-after neighborhood, this home is ideally located directly across from Oak Grove School, just around the corner from the Little League field, and within one mile of the hospital, middle and high schools, Interstate 91, and Brattleboro’s vibrant downtown shops and restaurants.This 4-bedroom, 1.5-bath Cape Cod–style home offers a quick closing opportunity and

  Lisa Friedman Great American Dream Realty

  49 Clark Ave, Brattleboro, VT 05301
• 

  

  /24

  $499,000

  • 7 Beds
  • 2 Baths
  • 2,038 Sq Ft

  45 Blue Brook Rd, Dover, VT 05356

  A truly unique and eclectic ski chalet. The current owner has tastefully updated this home in order to foster a tremendous rental investment, but it could also work great for anyone looking for a spacious ski home with great access off a paved town road and tremendous mountain proximity. Easily accessible off a paved road, not far from shuttle service, and only a couple miles to the Mount Snow

  Adam Palmiter Berkley & Veller Greenwood/Dover

  45 Blue Brook Rd, Dover, VT 05356
• 

  

  /18

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  5362 Us Route 5, Westminster, VT 05158

  BRAND NEW SEPTIC TO BE INSTALLED PRIOR TO CLOSING. Move-in ready home, ideally situated in the heart of picturesque Westminster. This 3-bedroom, 1-bath home offers the perfect blend of charm, comfort and convenience. Step inside from the sunny, porch into a bright and functional kitchen featuring new countertops and easy access to the first-floor laundry area and recently renovated full bath. The

  Karen Hoppe Berkley & Veller Greenwood Country

  5362 Us Route 5, Westminster, VT 05158

Showing Results 121 - 160, Page 4 of 5