Bennington County VT Homes for Sale

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  /12

  $299,999

  • Land
  • 10.05 Acres
  • $29,851 per Acre

  00 Garden Loop Rd, Winhall, VT 05340

  The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

  David White OwnerEntry.com

  00 Garden Loop Rd, Winhall, VT 05340
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  /45

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  951 Gage St, Bennington, VT 05201

  This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

  Dan Mason Perrott Realty

  951 Gage St, Bennington, VT 05201
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  /29

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
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  /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, Inc.

  144 Taconic Rd, Manchester, VT 05255
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  /7

  $175,000

  • Land
  • 15.49 Acres
  • $11,298 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
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  /44

  $199,000

  • 2 Beds
  • 2.5 Baths
  • 1,156 Sq Ft

  106 Park St Unit 2, Bennington, VT 05201

  Freshly updated 2-story townhouse in a convenient downtown Bennington location! This 2BR home features brand new stainless steel appliances, new vinyl plank flooring, and a fresh interior paint palette throughout. The open-concept main level offers a bright kitchen, dining, and living area—perfect for everyday living and entertaining—along with a pantry, half bath, and dedicated laundry room for

  Vicki Wilson Maple Leaf Realty

  106 Park St Unit 2, Bennington, VT 05201
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  /46

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 6,129 Sq Ft

  1035 Holy Smoke Rd, Shaftsbury, VT 05262

  Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

  Lori Hurley Four Corner Properties LLC

  1035 Holy Smoke Rd, Shaftsbury, VT 05262
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  /12

  $865,000

  • 12 Beds
  • 8 Baths
  • 5,568 Sq Ft

  1931 Vermont Route 67 E, Shaftsbury, VT 05262

  Rare investment opportunity in one of the area’s most desirable neighborhoods! This unique offering includes two historic buildings set on a spacious 1-acre lot, featuring a total of 8 well-maintained units—comprised of (4) two-bedroom apartments and (4) one-bedroom apartments. Each building offers shared covered front porches, perfect for enjoying the charm of this pleasant street setting. The

  Julie Glover Mahar McCarthy Real Estate

  1931 Vermont Route 67 E, Shaftsbury, VT 05262
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  /39

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1153 King Hill Rd, Readsboro, VT 05350

  This recently updated 1920s Vermont farmhouse features 4 bedrooms, 2 full bathrooms, and a versatile loft space on just over 8 acres! Large, updated windows showcase mountain views and allow natural light to fill every room, highlighting the home's charming original details alongside modern updates. The first floor has two bedrooms, both full bathrooms, first floor laundry, as well as TWO

  Casey Scott Southern Vermont Realty Group

  1153 King Hill Rd, Readsboro, VT 05350
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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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  /21

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  367 Shady Pines, Arlington, VT 05250

  Vermont charm blends with modern comfort in this private, updated, 4-bedroom, 2-bathroom chalet with more than 1,600 square feet of living space on 1.2 acres in Sunderland, Vt. Its classic chalet design with soaring windows fill the space with natural light and showcase the surrounding landscape.The first floor includes three bedrooms, a full bathroom, and a versatile bonus space ideal for an

  Kim Meeker Southern Vermont Realty Group

  367 Shady Pines, Arlington, VT 05250
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  /40

  $179,000

  • Land
  • 8,712 Sq Ft
  • $895,000 per Acre

  10 Partridge Hill, Manchester, VT 05255

  One of the last remaining lots in the exceptional Partridge Hill Association. This beautiful lot is situated to capture wonderful views and abbuts common land and a huge undeveloped land parcel on it's boundaries- offering a private outdoor space. The building envelope benefits from the ability to approach the parcel through the adjacent common land. Underground power and cable at the lot.

  Kim Morgan-Wohler Wohler Realty Group

  10 Partridge Hill, Manchester, VT 05255
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  /34

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,343 Sq Ft

  760 W Mountain Rd, Shaftsbury, VT 05262

  Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

  Kelley Mccarthy Mahar McCarthy Real Estate

  760 W Mountain Rd, Shaftsbury, VT 05262
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  /16

  $205,000

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  40 Bourn Brook Rd Unit 50, Manchester, VT 05255

  Modern In-Town Living and Fully Renovated Bourn Brook Condo. Experience the best of Manchester Center in this meticulously renovated end-unit at Bourn Brook. Whether you are looking for an affordable primary residence or a sleek "lock-and-leave" weekend getaway, this condo delivers modern style in a prime, walkable location.Interior HighlightsNo detail was spared in this top-to-bottom

  Robin Apps Four Seasons Sotheby's Int'l Realty

  40 Bourn Brook Rd Unit 50, Manchester, VT 05255
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  /17

  $160,000

  • Land
  • 2.9 Acres
  • $55,172 per Acre

  Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250

  This scenic undeveloped lot in Sunderland, Vermont, offers an exceptional opportunity to build in a peaceful yet convenient location. Set along a picturesque bike route, the property features level terrain that makes it ideal for easy construction and design flexibility. The land is already cleared, opening up the possibility for lovely mountain views and allowing you to envision your home

  Andy Reed Four Seasons Sotheby's Int'l Realty

  Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250
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  /52

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 4,650 Sq Ft

  20 Blackberry Ln, Peru, VT 05152

  Welcome to Bromley Village. This spacious 5 bedroom, 5 bath house offers everything you need to ensure the comfort of your group whether it’s large or small. The heart of this home is the magnificent great room with 20 foot ceilings, wood burning fireplace, slate floors, dining area and corner bar. The gourmet kitchen with red cabinets, soapstone counters, and top of the line appliances (Sub

  David Citron RE/MAX Four Seasons

  20 Blackberry Ln, Peru, VT 05152
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  /11

  $299,000

  • 4 Beds
  • 1 Bath
  • 2,156 Sq Ft

  558 Klondike Rd, Stamford, VT 05352

  This is a farmhouse that is currently under construction. Selling as is, with the remaining materials included. It is off grid and was lived in up until last year. Construction started in November 2025. Large barn that used to be a dairy farm. House has 3 woodstoves for heat. 10 cords of wood are included. Very nice setting along side a beautiful brook. 16.5 acres of open and wooded land that is

  Michael Jarvis United Country Real Estate Mike Jarvis Group Inc

  558 Klondike Rd, Stamford, VT 05352
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  /8

  $150,000

  • Land
  • 2.26 Acres
  • $66,372 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-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

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

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
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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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  /29

  $210,000

  • 9 Beds
  • 5 Baths
  • 3,810 Sq Ft

  6982 Main St, Readsboro, VT 05350

  Prime location meets potential! Situated in the center of charming Readsboro, this 5-unit multi-family property offers a rare opportunity for investors and owner-occupants alike. Whether you're looking to expand your portfolio or live in one unit while generating rental income from the others, this property delivers. Some renovations needed – perfect for those looking to add value and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  6982 Main St, Readsboro, VT 05350
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  /50

  $224,500

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  3264 Route 153, West Rupert, VT 05776

  This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a

  Scott McChesney McChesney RE, Inc.

  3264 Route 153, West Rupert, VT 05776
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  /22

  $895,000

  • Land
  • 24.08 Acres
  • $37,168 per Acre

  A Windsor Rd, Manchester, VT 05255

  Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

  Kim Morgan-Wohler Wohler Realty Group

  A Windsor Rd, Manchester, VT 05255
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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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  /45

  $490,642

  • 4 Beds
  • 2 Baths
  • 1,708 Sq Ft

  145 Oberdorf Rd, Readsboro, VT 05350

  Welcome to Alpenwald Village, a peaceful mountain community in scenic Readsboro, Vermont. This charming 4-bedroom chalet sits on 2 private acres and offers the perfect blend of comfort, style, and access to Vermont’s four-season lifestyle. Whether you're searching for a full-time residence or the ideal vacation getaway, this beautifully updated home delivers. Step inside to discover thoughtful

  Evan Russell Real Broker LLC

  145 Oberdorf Rd, Readsboro, VT 05350
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  /26

  $199,000

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft

  210 Division St, Bennington, VT 05201

  Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location!This beautifully renovated duplex is perfect for a first-time investor or owner-occupant looking to build equity while generating income. The property features a two-bedroom unit and a one-bedroom unit, both thoughtfully updated and well maintained.The first-floor unit has been fully renovated, including an updated

  Lilli West Maple Leaf Realty

  210 Division St, Bennington, VT 05201
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  /4

  $28,000

  • Land
  • 2.3 Acres
  • $12,174 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own a

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /28

  $375,000

  • 2 Beds
  • 1 Bath
  • 1,256 Sq Ft

  3510 Rupert Rd, West Rupert, VT 05776

  Beautifully maintained and truly one-of-a-kind, this "Very Vermonty!" 2-bedroom residence offers the perfect blend of charm, comfort, and functionality. Set above a spacious garage, the home is in mint, immaculate condition and designed for easy living. Inside, you’ll find a warm and inviting interior complemented by mini-split systems for efficient heating and cooling. Every detail reflects

  Faith Rhodes Maple Leaf Realty

  3510 Rupert Rd, West Rupert, VT 05776
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  /48

  $3,285,000

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

  68 Green Peak Orchard S, East Dorset, VT 05253

  Located in the desirable Green Peak Orchard, this exceptional custom Greek Revival residence is set on 9.9 private acres surrounded by mature landscaping, stone walls, and terraces. Thoughtfully designed with timeless craftsmanship, the home features wide-plank floors, hand-plastered walls and ceilings, custom moldings, historic reproduction lighting, and finely crafted wainscoting and cabinetry.

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

  68 Green Peak Orchard S, East Dorset, VT 05253
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  /15

  $825,000

  • Land
  • 77.6 Acres
  • $10,631 per Acre

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

  Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

  Trent Stephens Wohler Realty Group

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
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  /12

  $75,000

  • Land
  • 13.01 Acres
  • $5,765 per Acre

  3 W Hill Dr, Readsboro, VT 05350

  Discover the potential of this 13-acre parcel in scenic Readsboro offering RR (Rural Residential) zoning and endless possibilities. With gently rolling terrain and potential for views, this property is ideal for a private home or possible subdivision. Aerial photos and videos available! Enjoy a true outdoor lifestyle with nearby access to skiing, hiking, fishing, boating, snowmobile trails, and

  Derek Greene Derek Greene

  3 W Hill Dr, Readsboro, VT 05350
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  /8

  $65,000

  • Land
  • 1.24 Acres
  • $52,419 per Acre

  2041 East Rd, Bennington, VT 05201

  Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life.

  Dan Mason Perrott Realty

  2041 East Rd, Bennington, VT 05201
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  /60

  $1,900,000

  • 6 Beds
  • 6 Baths
  • 5,704 Sq Ft

  751 Main Rd, Stamford, VT 05352

  Step into the most amazing Victorian house you will ever see! Built in 1880, you will feel like you've walked back in time. Beautiful architecture and woodwork. The house was built by John Tudor, a Welsh immigrant who had made a fortune as a mill owner in northern Vermont and settled in Stamford. There is a stunning 3 floor Post & Beam Barn built in 2000 with a 2 car garage built-in. Barn also

  Michael Jarvis United Country Real Estate Mike Jarvis Group Inc

  751 Main Rd, Stamford, VT 05352
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  /60

  $1,595,000

  • 17 Beds
  • 20 Baths
  • 14,861 Sq Ft

  3888 Vermont Route 7a, Shaftsbury, VT 05262

  The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

  Vicki Wilson Maple Leaf Realty

  3888 Vermont Route 7a, Shaftsbury, VT 05262
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  /4

  $27,999

  • Land
  • 2.4 Acres
  • $11,666 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2.4-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /27

  $609,000

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

  60 Hilltop Rd Unit 60, Winhall, VT 05340

  Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  60 Hilltop Rd Unit 60, Winhall, VT 05340
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  /23

  $340,000

  • 3 Beds
  • 2 Baths
  • 1,590 Sq Ft

  22 Carlen St, Manchester Center, VT 05255

  Live in one and rent the other. Discover the charm and value of this affordable starter home with rental option. Located in a quiet, residential area of Manchester. This spacious ranch-style property offers a rare combination of flexibility, space, and opportunity, perfect for first-time buyers, investors, or anyone looking to create their dream home with a few finishing touches. The main level

  Andy Reed Four Seasons Sotheby's Int'l Realty

  22 Carlen St, Manchester Center, VT 05255
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  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms.

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
• 

  

  /15

  $500,000

  • Land
  • 21.2 Acres
  • $23,585 per Acre

  56 Lower Taylor Hill Rd, Winhall, VT 05340

  A rare opportunity to create a private Vermont retreat on 21.2 +/- acres along Lower Taylor Hill Road in Winhall. The property is supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, offering flexibility to design a substantial home within permitted limits. Rolling terrain, natural clearings, and mature woodland provide multiple potential building sites,

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  56 Lower Taylor Hill Rd, Winhall, VT 05340
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  /55

  $950,000

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

  24 N Branch Rd, Winhall, VT 05340

  Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.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-

  Kim Morgan-Wohler Wohler Realty Group

  24 N Branch Rd, Winhall, VT 05340

Showing Results 121 - 160, Page 4 of 6