Bennington County VT Homes for Sale

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  $219,000

  • 1,300 Sq Ft

  340 Pleasant St, Bennington, VT 05201

  Stop paying rent and start building equity! 340 Pleasant Street is a charming two-unit duplex located in the heart of Bennington, offering the perfect opportunity for an owner-occupant to live for less. The vacant lower unit is move-in ready, while the upstairs unit is occupied by a reliable, long-term tenant whose rent can significantly offset your mortgage payments. To make this deal even

  Lori Hurley Four Corner Properties LLC

  340 Pleasant St, Bennington, VT 05201
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  /5

  $575,000

  • 10 Beds
  • 8 Baths
  • 8,300 Sq Ft

  202-204 Beech St, Bennington, VT 05201

  Rare opportunity to own a high-performing multi-family portfolio on a spacious .75-acre lot in Bennington. This property features 9 total units spread across two well-maintained buildings. The primary 6-unit building has seen significant recent capital improvements, including a brand-new metal roof and five fully renovated apartments featuring modern finishes. The sixth unit remains occupied by a

  Lori Hurley Four Corner Properties LLC

  202-204 Beech St, Bennington, VT 05201
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  /15

  $324,950

  • 3 Beds
  • 2.5 Baths
  • 3,264 Sq Ft

  306 Sparrow Dr, Stamford, VT 05352

  Offering 3 bedroom 3 bath open concept with cathedral ceilings in dining area two bedrooms on 1st floor and master bedroom on second level .Full basement partially finished and in ground pool .

  April Shepard Twin State Realty LLC

  306 Sparrow Dr, Stamford, VT 05352
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  /25

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  2023 North Rd, Arlington, VT 05250

  This fully renovated home offers turnkey living just minutes to Manchester, Stratton, and Bromley. The main home was extensively renovated in Fall of 2025, inside & out. Exterior upgrades include new vinyl siding & trim, all new windows, upgraded insulation, a freshly stained deck, hot tub, custom dog fence, and selective tree clearing to expand lawn space, increase light, & enhance mountain

  Mandolyn McIntyre Crow Real Broker LLC

  2023 North Rd, Arlington, VT 05250
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  /15

  $640,000

  • 5 Beds
  • 4 Baths
  • 3,732 Sq Ft

  105 Elm St, Manchester, VT 05255

  This 4 unit multi family property located in Manchester's Depot district has been owned and managed by the same partnership group for over 30 years. The property is fully occupied with good tenants and is in excellent condition. There are two apartments on the first floor and two apartments on the second floor. There is ample of off street parking behind the building. There is coin operated

  David Citron RE/MAX Four Seasons

  105 Elm St, Manchester, VT 05255
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  /8

  $35,000

  • Land
  • 1 Acre
  • $35,000 per Acre

  0 Barber Pond Rd, Pownal, VT 05261

  Tucked into the scenic rural landscape of Pownal, Vermont, this approximate one-acre parcel of raw land offers a blend of natural privacy and water frontage on Barber Pond. Ideal for recreational use or future development, subject to local zoning and permitting. Enjoy the charm of the southern Vermont countryside while remaining within easy reach of nearby towns and outdoor amenities. Known for

  Vicki Wilson Maple Leaf Realty

  0 Barber Pond Rd, Pownal, VT 05261
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  /36

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  109 Watershed Rd, Woodford, VT 05201

  Well-maintained 1992 double-wide home with custom additions set on over 9 private acres. This spacious property offers 3 bedrooms and 2 full bathrooms, central air conditioning, a large living room and a separate family room, featuring its own fireplace—perfect for comfortable everyday living or gatherings. The home is in great condition throughout.A detached two-car garage, built in 2020,

  Faith Rhodes Maple Leaf Realty

  109 Watershed Rd, Woodford, VT 05201
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  /27

  $299,900

  • 1 Bed
  • 1 Bath
  • 1,085 Sq Ft

  2837 Main St, Manchester Center, VT 05255

  Located just off Route 7A near Hildene, The Lincoln Family Home, this charming bungalow offers the perfect balance of in town convenience and a private setting. Set on .82 acres, the home features one bedroom and one full bath with desirable first-floor living, making it ideal for a full time residence or an easy Vermont getaway.This home is filled with charming details and character,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 712-0520

  2837 Main St, Manchester Center, VT 05255
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  /25

  $1,425,000

  • 3 Beds
  • 2.5 Baths
  • 2,560 Sq Ft

  1058 Granger Hollow Rd, North Bennington, VT 05257

  A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room.Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  1058 Granger Hollow Rd, North Bennington, VT 05257
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  /60

  $2,750,000

  • 4 Beds
  • 7.5 Baths
  • 8,586 Sq Ft

  384 Riverbend Dr, Manchestr Ctr, VT 05255

  Exceptionally furnished, this residence is a "Stand Out" Ramsey Gourd, architect designed, coveted River Road Colonial accommodating 4,450 SF main level (8,585 SF on three floors) drenched in south facing light tying indoor - outdoor living to ideal mountain view perspectives. The East Mountains create the back drop for the elegantly laid out open concept that seamlessly transitions from area to

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 214-8628

  384 Riverbend Dr, Manchestr Ctr, VT 05255
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  /11

  $2,500,000

  • Land
  • 227 Acres
  • $11,013 per Acre

  00 Vermont 11, Peru, VT 05152

  Once-in-a-Lifetime 227+ Acre Legacy Property Bordering National Forest & Bromley Mountain Discover a rare opportunity to own 227+ acres of pristine Vermont land, directly abutting the National Forest and the slopes of Bromley Mountain. With breathtaking views of Stratton Mountain and the Green Mountains, this expansive property offers an unmatched canvas for your dream retreat-whether it's a

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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  /2

  $175,000

  • Land
  • 2.26 Acres
  • $77,434 per Acre

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

  Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Shuttle service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water permit in place for a 4 bedroom home.

  Tara van de Velde Four Seasons Sotheby's Int'l Realty

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
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  $1,399,000

  • 4 Beds
  • 3.5 Baths
  • 5,397 Sq Ft

  12 Sunny Hill Rd, Manchester Center, VT 05255

  One-of-a-kind, craftsman-built Vermont log home set on over 26 private acres with breathtaking, long-range mountain views. Tucked away at the dead end of the road, this exceptional property offers rare privacy while remaining close to premier ski mountains and all the dining, shopping, and cultural attractions of Manchester, VT. The land features two picturesque waterfalls and a serene natural

  Carrie Mathews Winhall Real Estate

  12 Sunny Hill Rd, Manchester Center, VT 05255
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  /28

  $425,000

  • 3 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  2023 North Rd, Arlington, VT 05250

  Rare opportunity to own a fully renovated home plus a subdivided, buildable lot with Mount Equinox views. 2023 North Rd offers turnkey living with exceptional future potential, just minutes to Manchester, Stratton, and Bromley. The main home was extensively renovated in Fall of 2025, inside & out. Exterior upgrades include new vinyl siding & trim, all new windows, upgraded insulation, a freshly

  Mandolyn McIntyre Crow Real Broker LLC

  2023 North Rd, Arlington, VT 05250
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  /2

  $2,190,000

  • Land
  • 1.16 Acres
  • $1,887,931 per Acre

  301 Northside Dr, Bennington, VT 05201

  Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

  Paul Carroccio TPW Real Estate

  301 Northside Dr, Bennington, VT 05201
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  $245,000

  • 2 Beds
  • 2 Baths
  • 911 Sq Ft

  726 Rice Ln, Bennington, VT 05201

  Welcome to this charming Cape-style home, nestled in a peaceful country setting just moments from Bennington College and scenic walking and hiking trails. This inviting property offers the perfect blend of rural tranquility and convenient access to town. Located just 10 minutes from downtown Bennington, you’ll have quick access to local shops, restaurants, cultural attractions, and everyday

  Thomas Martins Maple Leaf Realty

  726 Rice Ln, Bennington, VT 05201
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  /44

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,816 Sq Ft

  281 Old County Ln, Readsboro, VT 05350

  Nestled on more than two acres of beautifully maintained countryside and mature forest, this renovated 1892 farmhouse blends New England charm with peaceful seclusion and easy access to local attractions. Just 15 minutes from Mass MoCA, 25 minutes from Mount Snow, and close to hiking and ATV trails, it’s perfect for outdoor enthusiasts. Inside, you’ll find a warm and thoughtfully updated home

  Melissa Nebelski Real Broker LLC

  281 Old County Ln, Readsboro, VT 05350
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  /28

  $479,000

  • 3 Beds
  • 2.5 Baths
  • 1,392 Sq Ft

  354 New Ireland Rd, Manchester Center, VT 05255

  Cozy Country Getaway Close to It All, Tucked away on 2 private acres and bordered by Bromley Brook, this inviting 3-bedroom, 2.5-bath home offers the perfect balance of quiet country living and easy access to skiing (Bromley 5 miles, Stratton 14 miles) and town. Inside, you will find a spacious living and dining area, and fireplace with a woodstove insert, just right for curling up after a day on

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

  354 New Ireland Rd, Manchester Center, VT 05255
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  /16

  $139,000

  • Land
  • 1.62 Acres
  • $85,802 per Acre

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340

  wooded slightly elevated parcel. With clearing there should be some across valley views. Past soil test indicates proposed septic locations.Five-minute walk to Stratton snowmaking pond.

  Mike England Michael England Real Estate

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340
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  /35

  $699,000

  • 3 Beds
  • 2.5 Baths
  • 2,370 Sq Ft

  5 Linscott Rd Unit 56, Jamaica, VT 05343

  PRICE ADJUSTMENT This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright kitchen with

  Diana Stugger Four Seasons Sotheby's Int'l Realty

  5 Linscott Rd Unit 56, Jamaica, VT 05343
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  /25

  $975,000

  • 8,888 Sq Ft

  124 Elm St, Bennington, VT 05201

  An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

  Marek Kovac TPW Real Estate

  124 Elm St, Bennington, VT 05201
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  /3

  $219,000

  • 2 Beds
  • 1 Bath
  • 1,872 Sq Ft

  17 Henry Hill, Stamford, VT 05352

  Sean Taylor Moresi Real Estate Partners

  17 Henry Hill, Stamford, VT 05352
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  /41

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  7 Roundtree Rd, Winhall, VT 05340

  Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  7 Roundtree Rd, Winhall, VT 05340
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  $295,000

  • 1 Bed
  • 1.5 Baths
  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
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  /32

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft

  8 Silver Birch Rd Unit 8, Winhall, VT 05340

  Remarkable 3BR Birch Hill Value!Exceptional three-bedroom, two-bath end unit at Birch Hill! This well-thought-out floor plan is a true standout, providing two distinct living areas ideal for entertaining guests or relaxing after a day on the slopes. Features include an updated kitchen and dining space, two modernized baths, and a practical, renovated mudroom—essential for storing all your

  Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  8 Silver Birch Rd Unit 8, Winhall, VT 05340
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  /46

  $660,000

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft

  9 Pond View Rd Unit 9, Winhall, VT 05340

  Exceptional Renovation and Prime Intervale Location on the Pond . Beautiful upscale kitchen that opens to a wonderful great room with wood burning fireplace, cathedral ceiling, a spacious dining area and new deck with steps to the outdoors and pond. Tasteful details of this highly desirable floor plan with three bedrooms/3 baths that includes two bedrooms ensuite and a loft. The loft features

  Kim Morgan-Wohler Wohler Realty Group

  9 Pond View Rd Unit 9, Winhall, VT 05340
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  /27

  $310,000

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  196 Granger Hollow Rd, North Bennington, VT 05257

  This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large living room. 3 bedrooms, including an addition with a large primary with 2 closets inlcuding one whick is a large walk-in closet. A large full bath with washer/dryer hookups completes the living area. The house has a partial concrete basement

  Steve Schoppmeyer BHG Masiello Brattleboro

  196 Granger Hollow Rd, North Bennington, VT 05257
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  /52

  $725,000

  • 3 Beds
  • 4 Baths
  • 2,274 Sq Ft

  490 Barnumville Rd, Manchester Center, VT 05255

  490 Barnumville Road is a beautifully sited Manchester, Vermont home offering comfort, convenience, and classic Vermont charm on 1.78 flat, usable acres. Surrounded by peaceful views and just minutes from downtown Manchester, this property combines tranquil living with unbeatable access to everything the area has to offer — from ski and snowboard mountains to hiking trails, shopping, groceries,

  David Shehadi Josiah Allen Real Estate, Inc.

  490 Barnumville Rd, Manchester Center, VT 05255
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  /29

  $729,000

  • 3 Beds
  • 3.5 Baths
  • 2,262 Sq Ft

  253 Owls Head Hill Ln S, Dorset, VT 05251

  Welcome to this beautifully maintained Cape-style home tucked away on peaceful cul-de-sac with stunning mountain views. Enjoy your morning coffee on the front porch and relaxing evenings on the spacious back deck. Inside, you will find a warm and inviting layout featuring a gorgeous newer kitchen with modern finishes and ample space for cooking, gathering, and entertaining. The thoughtful floor

  Annette Gallo Real Broker LLC

  253 Owls Head Hill Ln S, Dorset, VT 05251
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  /58

  $299,000

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

  207 Silver St, Bennington, VT 05201

  Tastefully renovated antique home that retained it character 4 bed 2 bath home with gleaming hardwood floor in through out with Vinyl plank in the bathrooms and Laundry room. The downstairs Ensuite is currently being used as an in home office with private entrance. This would make a great room for a in-law space with private bath and the 3 season sunroom could easily be converted into a

  Dan Mason Perrott Realty

  207 Silver St, Bennington, VT 05201
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  /37

  $995,000

  • 4,724 Sq Ft

  1594 Vermont Route 7a, Shaftsbury, VT 05262

  Welcome to a truly unique and versatile property situated on 5 beautiful acres, offering a rare combination of residential comfort, business potential, and rental income. The main residence is a spacious 2,100 square foot home seamlessly connected to a large, fully equipped garage. This garage is a dream for automotive professionals or hobbyists, featuring two vehicle lifts, a high-ceilinged

  Kelley Mccarthy Mahar McCarthy Real Estate

  1594 Vermont Route 7a, Shaftsbury, VT 05262
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  /11

  $79,000

  • Land
  • 8 Acres
  • $9,875 per Acre

  1337 Chunks Brook Rd, Arlington, VT 05250

  Escape to the scenic beauty of Sandgate, VT with this 8-acre parcel on Chunks Brook Rd (House burnt down). Nestled in a country setting with wooded areas, rolling terrain, and mountain views, offering privacy and seclusion while remaining accessible. Enjoy streamside views, abundant wildlife, and the tranquility of nature while still within reach of local amenities. Sold As Is. The sale of this

  Derek Greene Derek Greene

  1337 Chunks Brook Rd, Arlington, VT 05250
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  /17

  $82,900

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  108 Baker Dr, Bennington, VT 01237

  Built in 2000 this charming home is located in Catamount Mobile Home Park, a community with no age restrictions in beautiful Bennington, Vermont. Situated on a large corner lot with front and back decks offering mountain views. Open, light-filled floor plan with bright kitchen, living room, primary suite, second bedroom, full bath, and laundry. Features include a newer shed (1 year old) and

  Colleen Zajac Monarch Realty

  108 Baker Dr, Bennington, VT 01237
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  /18

  $125,000

  • Land
  • 2.9 Acres
  • $43,103 per Acre

  311 Beechwood Ln, Peru, VT 05152

  This lovely, nearly 3 acre parcel of land is located on Beechwood Lane, about 1 mile from the Town center of Peru. There is approximately 353' frontage on Beechwood Lane and approximately 271' frontage on Beechnut Drive. The land is gently sloped and nicely wooded for privacy. Xfinity high speed internet available. Peru features the J.J. Hapgood General store, Peru Congregational Church, Hapgood

  Dylan Gage Bromley Real Estate

  311 Beechwood Ln, Peru, VT 05152
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  /18

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  940 Gage St, Bennington, VT 05201

  Classic cape with a twist! The eat-in kitchen has plenty of cooking area plus an eat-in area in a windowed alcove. The dining room is large enough for sit downs and the living room is the whole length of the house so movie nights are a go! In the entry side of the house you have a wonderful enclosed porch to serve as a mud room and a sweet sitting porch out front. AND!!!!... there is a fenced in

  Christine Lewis Brattleboro Area Realty

  940 Gage St, Bennington, VT 05201
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  /3

  $329,000

  • Land
  • 9.3 Acres
  • $35,376 per Acre

  1347 Morse Hill Rd, Dorset, VT 05251

  Discover the perfect blend of privacy and convenience with this 9.3 acre parcel nestled in one of Southern Vermont's most desirable locations. Enjoy sweeping mountain views and peaceful surroundings just minutes from the charming and historic towns of Dorset and Manchester, known for boutique shopping, fine dining, and year-round cultural attractions. It's a short drive to skiing and many other

  Deborah Hanst

  1347 Morse Hill Rd, Dorset, VT 05251
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  /20

  $534,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  1180 North Rd, East Arlington, VT 05252

  Have your own slice of quintessential Vermont with this 3 acre property at the base of the Green Mountains. A lush, wooded, private property, you will love this 4 bed, 2.5 bath Sunderland home. The 1st floor is an open floor plan with plenty of natural light with a bonus recreational room/office and half bath. The kitchen has granite counters with an updated faucet and oven hood with a butcher

  Jason Saphire www.HomeZu.com

  1180 North Rd, East Arlington, VT 05252
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  /60

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  150 Fillmore St, Bennington, VT 05201

  Location, location, location! Own your own private oasis on a dead-end road with nearly 7 acres - only minutes from downtown shopping and dining. Enjoy seasonal mountain views from the deck with sliding doors to the open concept living/dining room with vaulted ceiling. The propane fireplace with gorgeous wood mantle keeps things toasty while providing cozy ambiance. The spacious kitchen has

  Justine Curry Maple Leaf Realty

  150 Fillmore St, Bennington, VT 05201
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  /42

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262

  Welcome to Rod and Gun Club Rd. Offering 1748 sq ft, with a full useable basement, sitting on 4.43 acres of land, with a 3-bay garage with carport as well as, an attached 2-car garage, a barn with stalls if you want to have some animals. This newly renovated ranch style home with thoughtful design offers 3B,2Bath, with a spacious and flexible layout with a fireplace with a gas insert in the

  Wendy Larson Hooscik Realty

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262
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  /55

  $995,000

  • 5 Beds
  • 4.5 Baths
  • 2,321 Sq Ft

  24 N Branch Rd, Winhall, VT 05340

  Exceptional Renovation of a Stratton Resort Residence in the Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite- this mountain chalet has been updated

  Kim Morgan-Wohler Wohler Realty Group

  24 N Branch Rd, Winhall, VT 05340

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