Bennington County VT Homes for Sale

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  /25

  $385,000

  • Land
  • 41.1 Acres
  • $9,367 per Acre

  00 Ross Rd, Winhall, VT 05340

  Welcome to 41.1 acres of quintessential Vermont beauty, ideally located between downtown Manchester (11 minutes), Bromley Mountain (6 minutes), and Stratton Mountain (15 mins). This property offers the best of both worlds—easy access to town, ski mountains, and year-round recreation, yet a peaceful and private setting surrounded by nature. The land features a meandering stream, a mix of mature

  David Shehadi Josiah Allen Real Estate, Inc.

  00 Ross Rd, Winhall, VT 05340
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• 

  

  

  /41

  $520,000

  • 4 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  87 Grinka Farm Dr, Readsboro, VT 05350

  Set above the heart of Readsboro Village, this inviting four+ bedroom, two-and-a-half-bath home combines classic Vermont character with a versatile and welcoming layout. The first floor offers a formal living room centered around a striking fieldstone fireplace with a cast-iron woodstove, a separate den/media room for relaxation or movie night, a first-floor bedroom, a tasteful full bath, an

  Casey Scott Southern Vermont Realty Group

  87 Grinka Farm Dr, Readsboro, VT 05350
• 

  

  

  /17

  $75,000

  • Land
  • 2.38 Acres
  • $31,513 per Acre

  0 Sunset Hill Rd Unit B, Pownal, VT 05261

  Welcome to this gorgeous 2.38+/- acre lot in Pownal, Vermont! Located on a dead end, private road, this lot is nestled on the right hand side when pulling into Sunset Hill Road. Recently flagged for easy access. Mostly level with some vegetation in a quiet neighborhood. Are you dreaming of building your own home or investing in VT real estate? You won’t want to miss this beautiful lot close to

  Terri Edgerley Edge Realty Vermont

  0 Sunset Hill Rd Unit B, Pownal, VT 05261
• 

  

  

  /22

  $249,900

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft

  107 Coolidge Ave, Bennington, VT 05201

  Discover this beautifully updated home set directly on the Walloomsac River, offering 123 feet of peaceful river frontage. Enjoy fishing right from your own backyard, hosting gatherings by the water, or simply relaxing to the soothing sounds of the flowing river. Ideally located within walking distance of Main Street, the Rec Center (featuring a gym, sauna, indoor pool, and tennis and basketball

  Matt Waddington Hoffman Real Estate

  107 Coolidge Ave, Bennington, VT 05201
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  /60

  $579,900

  • 1 Bed
  • 1 Bath
  • 2,529 Sq Ft

  126 Simeon Dean Rd, Shaftsbury, VT 05262

  Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete

  Denise Byers Green Mountain Premiere Properties

  126 Simeon Dean Rd, Shaftsbury, VT 05262
• 

  

  /54

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  58 Mount Anthony Rd, Bennington, VT 05201

  Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

  Monique Geannelis Mahar McCarthy Real Estate

  58 Mount Anthony Rd, Bennington, VT 05201
• 

  

  /26

  $165,000

  • Land
  • 10 Acres
  • $16,500 per Acre

  777 Butternut Gutter, Arlington, VT 05250

  ''DIVIDED SKY, A RIVER SIDE RETREAT WITH PREMIER BROWN TROUT FISHING''! Nestled in the heart of Arlington, this breathtaking 10 acre lot offers unparalleled natural beauty, complete with sweeping mountain views and pristine surroundings! Perfect for outdoor enthusiasts, the lot features access to exceptional Brown Trout fishing waters, making it an Angler's Paradise! Whether you are

  Sunny Breen Josiah Allen Real Estate, Inc.

  777 Butternut Gutter, Arlington, VT 05250
• 

  

  /6

  $175,000

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  4677 Vt Route 100, Readsboro, VT 05350

  A great getaway or starter home tucked away in the Vermont woods. Up on a hill, there are partial mountain views, privacy and a fenced in area for animals and chickens. Close to VAST and VASA trail systems, hiking, hunting, backcountry skiing and lakes. Downhill skiing - multiple areas less than an hour away. Country living not too far from the city! Come check it out.

  Duncan Honig Maple Leaf Realty

  4677 Vt Route 100, Readsboro, VT 05350
• 

  

  /27

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,432 Sq Ft

  4928 Main St Unit 2, Manchester Center, VT 05255

  Fabulous two bedroom two bath condominium converted in 2017 in the heart of Manchester Center. Many fine features: Marvin windows, hardwood flooring, central air conditioning, forced hot air heat, private second floor sundeck, mountain views. This one level second floor unit is accessed by private elevator and offers pretty mountain views through the oversized 9 foot windows. The living room has

  David Halligan Four Seasons Sotheby's Int'l Realty

  4928 Main St Unit 2, Manchester Center, VT 05255
• 

  

  /30

  $735,000

  • 3 Beds
  • 3 Baths
  • 2,317 Sq Ft

  32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

  This gorgeous Stratton area townhome is designed for comfort and style, featuring three spacious bedrooms, three baths plus an open loft. Being a Highgate model, it offers a second family room with ample space for relaxation and entertainment, making it perfect for holiday gatherings. The interior of this special home has been freshly painted in October '25 and stunning wide-board pine floors

  Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
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  /34

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  114 Colebrook Rd, East Arlington, VT 05252

  This is an unfinished home that needs the right owner to complete it to its fullcapacity.Set off on a private road this home is set on a beautiful, secluded, wooded lot.Access to major highways and schools

  David White OwnerEntry.com

  114 Colebrook Rd, East Arlington, VT 05252
• 

  /2

  $74,900

  • Land
  • 5.3 Acres
  • $14,132 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 5-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
• 

  

  /9

  $1,350,000 New Construction

  • 3 Beds
  • 4.5 Baths
  • 3,415 Sq Ft

  3746 Main St Unit A, Manchester, VT 05255

  Last Available Unit– This final Monarch on Main townhome is Luxury Living in Historic Manchester Village at its finest. Available Winter 2026, this premier Monarch on Main property offers the rare opportunity to own a thoughtfully designed townhome- front unit- in the heart of Manchester Village. Imagine an easy stroll to fine dinning, shopping and evening events. This three-level residence

  Britt Wohler

  3746 Main St Unit A, Manchester, VT 05255
• 

  

  /45

  $895,000

  • 8 Beds
  • 6 Baths
  • 4,326 Sq Ft

  143 Nichols Rd, Peru, VT 05152

  This is remarkable property in Peru, Vermont, that offers year-round enjoyment.This sun-filled home is situated on 10 acres of land, boasting beautiful mountain views and a private pond complete with a beach, deck, above-ground pool, and a sauna. Imagine swimming, fishing, and hiking in the warmer months, and ice-skating, snowmobiling, and cross-country skiing in the winter—all on your

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  143 Nichols Rd, Peru, VT 05152
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  /30

  $629,000

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  115 Nottingham Park, Manchester Center, VT 05255

  This spacious raised ranch sits on 1.08 acres and offers seasonal western mountain views, with close proximity to both Bromley and Stratton.The home features a large, open-concept floor plan on the main level, including a living room and a combined dining/kitchen area with a cathedral ceiling and a wood-burning stove on a raised brick hearth. This floor also has three bedrooms and one full

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  115 Nottingham Park, Manchester Center, VT 05255
• 

  

  /40

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft

  134 Monument Ave, Bennington, VT 05201

  Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary

  Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
• 

  

  /40

  $215,000

  • 5 Beds
  • 2 Baths
  • 2,201 Sq Ft

  317 Pleasant St, Bennington, VT 05201

  Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400).

  Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
• 

  

  /45

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  9 Lower Taylor Hill Rd, Winhall, VT 05340

  Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

  Timothy Mich Doddridge Stratton Real Estate

  9 Lower Taylor Hill Rd, Winhall, VT 05340
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  /58

  $295,000

  • 3 Beds
  • 1.5 Baths
  • 1,934 Sq Ft

  508 Barney Rd, Bennington, VT 05201

  WOW CHECK OUT THIS Country Cutie on the edge of town. The home has been updated while keeping the period Charm. Large level nicely landscaped yard enclosed by hedges. The lager living room has a fireplace with insert and lots of built-ins. The walkout basement has a large room that has been used as a bedroom with a stone fireplace and a half bath in the heated workshop area.

  Dan Mason Perrott Realty

  508 Barney Rd, Bennington, VT 05201
• 

  

  /56

  $3,350,000

  • 3 Beds
  • 4.5 Baths
  • 3,059 Sq Ft

  466 3 Maple Dr, Manchester, VT 05254

  Welcome to Three Maple Drive, a beautifully crafted, brand-new single-family home nestled in a quiet and scenic location in Manchester, Vermont. Built in 2023 with impeccable attention to detail, this 3,059 sq ft modern farmhouse seamlessly blends luxury, comfort, and timeless design—all set on a private 3.85-acre lot with gorgeous mountain views.This home features three spacious bedroom

  David Shehadi Josiah Allen Real Estate, Inc.

  466 3 Maple Dr, Manchester, VT 05254
• 

  

  /45

  $450,000

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft

  848 Coleville Rd, Bennington, VT 05201

  The House that Love Built-Multigenerational Comfort &Thoughtful Design Tucked away in a peaceful neighborhood, set back from a well maintained town road. This beautifully maintained home is perfect for wildlife watching and enjoying serene solitude.Designed with multigenerational or accessible living in mind, the home features a private in-law suite with it's own ramp entry, wide doorways,

  Beatrice O'Connell Maple Leaf Realty

  848 Coleville Rd, Bennington, VT 05201
• 

  

  /33

  $815,000

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  158 Upland Downs Rd, Manchester Center, VT 05255

  This well-maintained home is nestled on an open, sunny lot with mountain views, offering a serene and picturesque setting. The property is in move-in condition and boasts one of Manchester's best locations, providing convenient access to the town, schools, and shops, all just minutes away. It is set back from the road, surrounded by beautifully landscaped lawn, gardens, and a spacious

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  158 Upland Downs Rd, Manchester Center, VT 05255
• 

  

  /40

  $875,000

  • 6 Beds
  • 5 Baths
  • 5,689 Sq Ft

  2677 Route 30, Dorset, VT 05251

  Dorset Historic six-bedroom farmhouse with an apartment above a garage on 1.79 acres with view. This charming home blends Vermont rustic appeal with modern family living.Upon entering, you'll find a brightly lit mudroom with wide board flooring, built-in shelving, and ample space for all seasons. This leads into a large breakfast room that adjoins the kitchen and family rooms. The first

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  2677 Route 30, Dorset, VT 05251
• 

  

  /29

  $415,000

  • 6 Beds
  • 3 Baths
  • 5,208 Sq Ft

  126 Washington Ave, Bennington, VT 05201

  Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 266-4364

  126 Washington Ave, Bennington, VT 05201
• 

  

  /7

  $29,000

  • Land
  • 1.2 Acres
  • $24,167 per Acre

  00 Oberdorf Rd, Stamford, VT 05350

  This 1.2 acre rectangular lot is located in Alpenwald Village! The village roads are community-maintained, have electricity service through Green Mountain Power Company and is loaded with recreational perks! 1.4 miles to hiking/ biking trails on the Dutch Hill Backcountry Area of the Green Mountain National Forest. 1.9 miles to an ATV & snowmobile trailhead in Heartwellville. Situated in the town

  Casey Scott Southern Vermont Realty Group

  00 Oberdorf Rd, Stamford, VT 05350
• 

  

  /33

  $2,295,000

  • 4 Beds
  • 5.5 Baths
  • 4,506 Sq Ft

  3039 Vermont 30, Pawlet, VT 05761

  Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels—over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making

  Carrie Mathews Winhall Real Estate

  3039 Vermont 30, Pawlet, VT 05761
• 

  

  /46

  $1,495,000

  • 4 Beds
  • 4.5 Baths
  • 5,170 Sq Ft

  50 Grouse Ln, Dorset, VT 05251

  Custom built Dorset Hollow estate offered for the first time since 1998. Located on 10 extremely private acres, this 5,100 sqft home offers 4 bedrooms and five bathrooms, plus a two car attached garage. Many fine features including: four fireplaces, verdi marble flooring, marvin windows, slate roof, viessmann boiler - all top of the line. The living room is exceptional w large wood burning

  David Halligan Four Seasons Sotheby's Int'l Realty

  50 Grouse Ln, Dorset, VT 05251
• 

  

  /43

  $1,895,000

  • 6 Beds
  • 5.5 Baths
  • 5,178 Sq Ft

  144 Taconic Rd, Manchester, VT 05255

  “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

  Tom Deck Josiah Allen Real Estate, Manchester Branch Office

  144 Taconic Rd, Manchester, VT 05255
• 

  

  /23

  $159,900

  • 4 Beds
  • 2 Baths
  • 1,596 Sq Ft

  4697 Main Rd, Stamford, VT 05352

  Situated on a large 4+acre lot sits this adequately sized home!! 3-4 bedrooms with 1 3/4 bathrooms this home awaits your visions and ideas. With spacious rooms and a functional layout this home has many options. 1 car detached garage and vinyl siding are a plus!

  Dick Thackston R.H. Thackston & Company

  4697 Main Rd, Stamford, VT 05352
• 

  

  /60

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,975 Sq Ft

  58 Hicks Ln, Manchester Center, VT 05255

  OPEN HOUSE SATURDAY 10/25 11AM - 1PM ~ Manchester Center VT home for sale. Classic single family Colonial on a rare in town 0.70 acre lot. Quiet dead end lane near downtown. This 4 bedroom 3 bath property offers about 3,000 SF of finished living area plus flexible bonus space. The floor plan supports daily living and weekend guests with ease for the Manchester Center lifestyle in Bennington

  Nick Sicard EXP Realty

  58 Hicks Ln, Manchester Center, VT 05255
• 

  

  /43

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,884 Sq Ft

  21 County Rd, Pownal, VT 05261

  Step into the warmth and character of this spacious 4-bedroom, 2-bath farmhouse set on 16 picturesque acres. A classic center hall with a beautiful wooden staircase welcomes you inside, where hardwood floors, exposed beams, and three cozy wood stoves create a timeless, inviting feel throughout.The large country kitchen opens directly to a fenced-in backyard, perfect for pets or simply

  Julie Glover Mahar McCarthy Real Estate

  21 County Rd, Pownal, VT 05261
• 

  

  /52

  $2,300,000

  • 6 Beds
  • 3 Baths
  • 3,340 Sq Ft

  215 & 221 Vt Route 30, Dorset, VT 05251

  Two homes, multiple barns and outbuildings on 69 incredible acres in Dorset, VT. Nestled in the Green Mountains, 215 Route 30 the 1780s farmhouse featuring 3 bedrooms, 2 baths with 1645 finished sqft. The second building, nestled away from the road is 221 Route 30 built in 1940 with 3 bedrooms and 2 baths. 1800 sqft. The property offers pastoral venues, mature forest, and scenic mountain views. A

  Margretta Fischer Wohler Realty Group

  215 & 221 Vt Route 30, Dorset, VT 05251
• 

  

  /12

  $37,100

  • 2 Beds
  • 1 Bath
  • 1,302 Sq Ft

  933 East Rd, Bennington, VT 05201

  Built in 1965, this one level home offers approximately 1302 finished square feet, two bedrooms and one full bath, fireplace, unfinished basement and deck. This home sits on an approximate 44867 sqft lot. This property is in uninhabitable condition and boarded up. UNSAFE TO ENTER, foundation cracked, fallen and caved in.

  Sherry Price REALHome Services and Solutions, Inc.

  933 East Rd, Bennington, VT 05201
• 

  

  /44

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,661 Sq Ft

  2842 Vermont Route 7a, Shaftsbury, VT 05262

  Spacious split level on 1.16 acres with spectacular views. Surrounded by Grateful Morning Farm, the simple beauty and peaceful landscape is breathtaking. Enjoy your coffee while watching sunrises from the rear stone patio or breakfast nook, both overlooking the big backyard with mountain backdrop. In summertime, the mini split and ceiling fans will keep you cool, and in Vermont's magical winter

  Jenifer Prouty Hoffman Hoffman Real Estate

  2842 Vermont Route 7a, Shaftsbury, VT 05262
• 

  

  /32

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,696 Sq Ft

  130 Ipan Rd, North Bennington, VT 05257

  Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty

  Kelley Mccarthy Mahar McCarthy Real Estate

  130 Ipan Rd, North Bennington, VT 05257
• 

  

  /31

  $339,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  This inviting in-town home has been nearly completely renovated with only a few more touches to be brought by the new owner, blending fresh updates with classic comfort. Inside, you’ll find 3 bedrooms and a full bath, plus a bonus room that could serve as a 4th bedroom with a half-bath. An additional room with its own separate entrance is ideal for a small home business. The convenient attached

  Cassie Barbeau Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
• 

  

  /21

  $105,000

  • Land
  • 0.45 Acre
  • $233,333 per Acre

  236-240 Grandview St, Bennington, VT 05201

  Call your builder! This double lot is ready to build on. Public water, sewer, and electricity are at the street on a town-maintained, paved village residential road. The lot is ideally situated close to essential amenities, including the hospital and a vibrant Main Street boasting diverse shops, restaurants, breweries, and groceries. Enjoy exceptional access to the outdoors with the nearby Green

  Lori Hurley Four Corner Properties LLC

  236-240 Grandview St, Bennington, VT 05201
• 

  

  /60

  $5,250,000

  • 9 Beds
  • 10 Baths
  • 7,900 Sq Ft

  1184 E Manchester Rd, Manchester, VT 05255

  Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  1184 E Manchester Rd, Manchester, VT 05255
• 

  

  /43

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 4,788 Sq Ft

  6 Chad Cir, Winhall, VT 05340

  Tucked away at the end of a private cul-de-sac and just minutes from Stratton's slopes, this beautifully designed mountain home offers the perfect blend of comfort and luxury. The open-concept floor plan features a chef’s kitchen with granite countertops, a 6-burner professional gas stove, double ovens, a farm sink, and a wet bar with ice maker—ideal for entertaining. Wide pine floors and a

  Carrie Mathews Winhall Real Estate

  6 Chad Cir, Winhall, VT 05340
• 

  

  /48

  $3,285,000

  • 5 Beds
  • 6 Baths
  • 6,900 Sq Ft

  68 Green Peak Orchard Rd N, Dorset, VT 05253

  Located in Green Peak Orchard, this custom Greek Revival home on 9.9 aces features wide-planked floors, custom moldings, hand-plastered walls and ceilings, historic reproduction lighting and custom wainscotting & cabinetry. Slate and copper roofs as well as Vermont marble and soapstone complete the authentic details of this striking residence. The home welcomes you through a brick-floored mudroom

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  68 Green Peak Orchard Rd N, Dorset, VT 05253

Showing Results 41 - 80, Page 2 of 6