Bennington County VT Homes for Sale

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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, Manchester Branch Office

  144 Taconic Rd, Manchester, VT 05255
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  /23

  $148,900

  • 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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /21

  $99,000

  • Land
  • 0.45 Acre
  • $220,000 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
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  /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
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  /55

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  935 Old Manchester Rd, Peru, VT 05152

  Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

  Margretta Fischer Wohler Realty Group

  935 Old Manchester Rd, Peru, VT 05152
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  /31

  $339,000

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

  103 Norton St, Bennington, VT 05201

  Beautifully Renovated 4-Bedroom Home with Modern Upgrades! Welcome to this stunning, move-in ready home that has been fully renovated with care and style. Offering 4 spacious bedrooms, 2 brand-new bathrooms, and 1,728 square feet of thoughtfully designed living space, this home is the perfect blend of comfort and modern living.Step inside to find gleaming hardwood floors that flow throughout

  Timothy Corcoran Mahar McCarthy Real Estate

  103 Norton St, Bennington, VT 05201
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  /27

  $319,000

  • 3 Beds
  • 1 Bath
  • 836 Sq Ft

  557 Beech St, Manchester Center, VT 05255

  Manchester. Let the sun shine in. Easy living on one level with 3 bedrooms. You'll enjoy sitting in the kitchen and gazing either at the mountain view or the flower garden in the backyard. Nice level area to plant a garden or play outdoor games in the yard. Detached 1 car garage, good storage and area for workbench. Quick drive into center of Manchester and minutes to the Manchester Country Club.

  Patti Trudel RE/MAX Four Seasons

  557 Beech St, Manchester Center, VT 05255
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  /31

  $495,000

  • 7 Beds
  • 4 Baths
  • 2,494 Sq Ft

  190 Cemetery Rd, Arlington, VT 05250

  This is a RARE two lot offering!! It is located on Cemetery Rd in Arlington,VT with quiet, secluded lots. Great opportunity for multi-generational living, guest house, rental income, air bnb, extra space or great resale opportunity. House #1 is a two story house on 2.29 surveyed acres with 4 bedrooms and 1 3⁄4 bathrooms. The living room features a cathedral ceiling with skylights and a wood

  

  Trent Stephens

  Wohler Realty Group

  (802) 200-2970

  190 Cemetery Rd, Arlington, VT 05250
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  /20

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  27 Owls Head Hill Ln, Dorset, VT 05251

  Charming Raised Ranch on 2 Acres – Dorset, VTWelcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space.3 Bedrooms | 2 Full Baths | 2-Car Attached GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  27 Owls Head Hill Ln, Dorset, VT 05251
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  /21

  $120,000

  • Land
  • 20 Acres
  • $6,000 per Acre

  1319 Vail Rd, Bennington, VT 05201

  Discover an exceptional opportunity to build your dream home on this prime 20-acre parcel located in the desirable west end of Bennington. This expansive property offers a perfect blend of privacy and convenience, ready for immediate development.Key features of this remarkable land include an established driveway providing easy access to your future homesite, and a completed perk test

  Lilli West Maple Leaf Realty

  1319 Vail Rd, Bennington, VT 05201
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  /56

  $2,300,000

  • 9 Beds
  • 8 Baths
  • 5,512 Sq Ft

  288 Cedar Ln, Peru, VT 05152

  Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

  Jessica Citera Cummings & Co

  288 Cedar Ln, Peru, VT 05152
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  /39

  $289,000

  • 2 Beds
  • 1.5 Baths
  • 1,417 Sq Ft

  51 Russell St Unit D, Arlington, VT 05250

  A Wonderful Townhouse in desirable Arlington Village. Welcome to this charming 2 bedroom 1 and a half bath nestled in the heart of Arlington, with a one car garage. This location offers the perfect blend of comfort and convenience. Inside you will find newly refinished hardwood floors, updated tiling at the entry, and stainless steel appliances. A sun drenched living room and dining area walks

  Robert Sabol Wohler Realty Group

  51 Russell St Unit D, Arlington, VT 05250
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  /15

  $269,000

  • 2 Beds
  • 1 Bath
  • 2,500 Sq Ft

  624 Main St, Bennington, VT 05201

  Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

  Kelley Mccarthy Mahar McCarthy Real Estate

  624 Main St, Bennington, VT 05201
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  /35

  $575,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  704 Fox Hill Rd, Bennington, VT 05201

  House hunting in Vermont and can't find what you want? Or it sold before you had time to tour or think it through? This brand new custom built home could be the answer. Desirable neighborhood with paved town roads, close to SVMC hospital, Bennington College, downtown restaurants and events, and one hour from Albany Int'l Airport. Nestled at the base of Mount Anthony, there's direct access to the

  Jenifer Prouty Hoffman Hoffman Real Estate

  704 Fox Hill Rd, Bennington, VT 05201
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  /47

  $625,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  682 Fox Hill Rd, Bennington, VT 05201

  Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct access

  Jenifer Prouty Hoffman Hoffman Real Estate

  682 Fox Hill Rd, Bennington, VT 05201
• 

  

  /22

  $575,000

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

  203 Northside Dr, Bennington, VT 05201

  Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 471-3591

  203 Northside Dr, Bennington, VT 05201
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  /30

  $550,000

  • 2 Beds
  • 2 Baths
  • 2,218 Sq Ft

  1439 Main St, Manchester Center, VT 05255

  Purdy School House, est. 1850 - Step into history with this lovingly preserved former schoolhouse, offering timeless character with modern comfort. Featuring 2 bedrooms, 2 baths, and a striking stone fireplace, this home blends warmth and charm. A full basement and attached one-car garage provide practical convenience. Set on 2.01 acres, the property includes a fenced dog yard and plenty of space

  Richard Slocum Four Seasons Sotheby's Int'l Realty

  1439 Main St, Manchester Center, VT 05255
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  /28

  $629,000

  • 3 Beds
  • 2 Baths
  • 1,958 Sq Ft

  550 Finbars Forest Rd, Manchester Center, VT 05255

  Priced to sell!!! This modern farmhouse brings easy winter living to the Green Mountains. Set on two private, wooded acres, it’s less than 8 miles to Bromley and under 30 minutes to Stratton, making it a great home base for skiers and riders. You’re also just minutes from downtown Manchester and within the Burr & Burton Academy school district. With modern systems and thoughtful upgrades, the

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  550 Finbars Forest Rd, Manchester Center, VT 05255
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  /52

  $259,000

  • 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
• 

  

  /22

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340

  Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

  Robin Apps Four Seasons Sotheby's Int'l Realty

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340
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  /40

  $1,525,000

  • 4 Beds
  • 3 Baths
  • 3,931 Sq Ft

  932 Mcnamara Rd, Dorset, VT 05251

  Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality

  Britt Wohler

  932 Mcnamara Rd, Dorset, VT 05251
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  /17

  $85,000

  • Land
  • 9.74 Acres
  • $8,727 per Acre

  1 & 2 Joy Ln, Arlington, VT 05250

  Two Perked and Permitted Building Lots tucked away in the village of Arlington. Survey and Waste Water Permit available for two lots totaling 9.74 acres. These two Joy Lane lots are ready for your vision and your dreams. Close to town and all amenities, however private. Opportunity awaits to build one house or two. Owners are selling both lots together. The next owner could build on one lot and

  Margretta Fischer Wohler Realty Group

  1 & 2 Joy Ln, Arlington, VT 05250
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  /29

  $250,000

  • 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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  /36

  $224,500

  • 5 Beds
  • 2 Baths
  • 2,212 Sq Ft

  1138 Main Rd, Stamford, VT 05352

  Stamford, VT - A country drive less than 10 minutes North Adams, MA- home of Mass MoCA. Dating back to 1850 this spacious home boasts 4 bedrooms & 2 baths. 1st floor bedroom, bath, laundry, kitchen, dining, living room, den & sunroom. Nestled on almost and acre of land and bordering a babbling brook this property offers a privacy sanctuary. Come take a look for yourself! Located close to

  Colleen Zajac MONARCH REALTY, INC.

  1138 Main Rd, Stamford, VT 05352
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  /37

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  17 Roundtree Rd, Winhall, VT 05340

  Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

  Sarah Nichols Winhall Real Estate

  17 Roundtree Rd, Winhall, VT 05340
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  /38

  $749,000

  • 3 Beds
  • 2.5 Baths
  • 4,683 Sq Ft

  2744 Danby Mountain Rd, Dorset, VT 05251

  This classic Vermont mountain retreat offers the perfect blend of comfort, privacy, and year-round recreation. Located just minutes from Dorset Village and Manchester, the property is surrounded by adventure—ski touring, snowshoeing, and hiking are all available right from your yard. A new wrap-around Trex deck invites you to unwind or dine outdoors while taking in views of the gardens and

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  2744 Danby Mountain Rd, Dorset, VT 05251
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  /8

  $59,000

  • Land
  • 0.29 Acre
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
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  /43

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  100 Walsh Rd, Arlington, VT 05250

  Tucked away in the picturesque Vermont Hamlet of Sandgate, home to just 480 residents, this property provides the perfect escape from the bustle of city life. Here, you can enjoy the warmth of a close-knit community, stunning natural surroundings, and easy access to local amenities. Sitting on a generous 1.5-acre lot, the property offers ample space for outdoor recreation and the peaceful

  

  Kristin Comeau

  TPW Real Estate

  (802) 521-2780

  100 Walsh Rd, Arlington, VT 05250
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  /43

  $2,300,000

  • Land
  • 67 Acres
  • $34,328 per Acre

  215 Vermont 30, Dorset, VT 05251

  Opportunities are Knocking! Welcome to an extraordinary 67-acre estate parcel in Dorset, perfectly positioned along Route 30. This remarkable property offers the ultimate trifecta—location, natural beauty, and limitless potential. Bordering a gentle brook and featuring a mix of rolling meadows and scenic mountain logging trails, this raw, untouched farmland is a rare find in one of Vermont’s most

  Margretta Fischer Wohler Realty Group

  215 Vermont 30, Dorset, VT 05251
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  /44

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  475 Sunrise Ln, Arlington, VT 05250

  Discover your private retreat on Beautiful Sunrise Lane! Welcome to "Pine Hollow". This comfortable and inviting home sits on over 6 acres of serene, peaceful landscape, for those seeking a quiet environment and space! Idyllic setting surrounded by pines with complete solitude at the end of a private rd. Enjoy the comfort of generous rooms filled with natural light, ideal for family living and

  Sunny Breen Josiah Allen Real Estate, Inc.

  475 Sunrise Ln, Arlington, VT 05250
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  /2

  $65,000

  • Land
  • 17.3 Acres
  • $3,757 per Acre

  0 Hidden Valley Rd Unit 5055076, Shaftsbury, VT 05262

  Ready to build 17 acer lot with wastewater permit for a 4 bedroom single family residence. Great potential for a pond site, the trail on the lot make it a great opportunity for a horse paddock.

  Dan Mason Perrott Realty

  0 Hidden Valley Rd Unit 5055076, Shaftsbury, VT 05262
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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

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
• 

  

  /23

  $360,000

  • 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
• 

  

  /28

  $414,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  139 Bergwelt Ln, Readsboro, VT 05350

  Charming Country Retreat with Scenic Views and Timeless Character.Welcome to your dream country escape! Nestled on a peaceful, tree-lined lane, this beautifully maintained 3-bedroom, 2-bathroom home offers the perfect blend of rustic charm and modern comfort. Set on a spacious 3.6 acre lot, the property boasts serene views, mature gardens, and ample privacy — ideal for relaxing weekends or

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  139 Bergwelt Ln, Readsboro, VT 05350
• 

  

  /59

  $2,800,000

  • 3 Beds
  • 3.5 Baths
  • 3,938 Sq Ft

  23 Valley View Rd, Winhall, VT 05340

  Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

  Kim Morgan-Wohler Wohler Realty Group

  23 Valley View Rd, Winhall, VT 05340

Showing Results 81 - 120, Page 3 of 5