Bennington County VT Homes for Sale

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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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  /25

  $350,000

  • Land
  • 26.5 Acres
  • $13,208 per Acre

  942 Rt 315 Route, Rupert, VT 05768

  26.5 acres offering all the sought after components and is conveniently located nearby the greater Dorset/Manchester amenities! The 26.5 acres is enrolled in the Current Use (Land Use) program however, is about to be removed. The acreage backs onto the 3000 acre Merck Forrest Foundation which offers tremendous hiking, snowshoe trekking, camping, farmstead activity, sugaring, and nature tracking.

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 347-9113

  942 Rt 315 Route, Rupert, VT 05768
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  /33

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 3,658 Sq Ft

  146 Ridges Way Unit 1200-1, Peru, VT 05152

  The Top of the World! Follow the road to the very top of Bromley Village where this secluded condo enjoys sweeping views of the surrounding Green Mountains. This three level, well appointed unit has four nice sized bedrooms, three and a half baths and is a short walk to the Plaza trail for mountain access. Long time owners added special features to this Ridges Townhouse, including hand wrought

  

  Christopher Cummings

  Cummings & Co

  (802) 481-3899

  146 Ridges Way Unit 1200-1, Peru, VT 05152
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  /36

  $699,000

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

  682 E Manchester Rd, Manchester Center, VT 05255

  Welcome to a private Vermont retreat that blends rustic post-and-beam charm with modern versatility. Nestled above the serene Bourne Brook, this property offers the perfect balance of privacy, natural beauty and convenience. The main house exudes warmth and craftmanship, and is complemented by an income producing apartment above the 2 car garage, adding flexibility for extra guests, long term

  

  Christopher Cummings

  Cummings & Co

  (802) 441-7038

  682 E Manchester Rd, Manchester Center, VT 05255
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  /60

  $629,000

  • 5 Beds
  • 3.5 Baths
  • 3,271 Sq Ft

  5408 Main St, Manchester Center, VT 05255

  A great in town location offering two Homes,#5406 and #5408. The Front house is a three bedroom, two full bath home with a great front covered porch with views of Mt. Equinox. You can easily walk to all of Manchester Center's amenities. The back Cottage has two bedrooms, one and a half baths with kitchen and living area. This property is zoned as multi use which provides the owners the ability to

  Robert Sabol Wohler Realty Group

  5408 Main St, Manchester Center, VT 05255
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  /40

  $1,150,000

  • 5 Beds
  • 3.5 Baths
  • 4,017 Sq Ft

  11 Founders Hill Rd, Winhall, VT 05360

  Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lot justdown the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  11 Founders Hill Rd, Winhall, VT 05360
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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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  /24

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 2,210 Sq Ft

  74 Eagle Nest Rd Unit 7, Manchester, VT 05255

  Eagle Nest in Manchester, The Only Available Unit in This Sought-After Community! Welcome to easy living at Eagle Nest, a popular cluster home development where opportunities like this are rare. This freestanding home (no shared walls, no shared noise!) is being offered for the first time and has been beautifully updated from top to bottom. Step inside to find fresh interior paint, new carpeting,

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

  74 Eagle Nest Rd Unit 7, Manchester, VT 05255
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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. 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
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  /4

  $14,000

  • Land
  • 1.2 Acres
  • $11,667 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1.2-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
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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. 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
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  /9

  $19,999

  • Land
  • 1.5 Acres
  • $13,333 per Acre

  0 Lebensdorf Ln, Readsboro, VT 05350

  Rectangular building lot in Alpenwald Village. The topography is slightly below road grade but generally flat. Electricity is available at the road. This is a very well maintained development and road system, with lots of privacy and neighbors widely spread out on their own acreage, yet there's still a friendly community feel.

  David White OwnerEntry.com

  0 Lebensdorf Ln, Readsboro, VT 05350
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  /50

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades.This beautifully updated 3-bedroom home is perfectly situated on a desirable corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, with a recent addition of a first-floor primary bedroom and new mudroom back entrance.Step inside to find gleaming hardwood floors and a warm, inviting layout. The dining

  Lindsey Martin Maple Leaf Realty

  113 Main St, Bennington, VT 05201
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  /54

  $235,000

  • 3 Beds
  • 3 Baths
  • 2,128 Sq Ft

  48 Canal Dr, Readsboro, VT 05350

  What an opportunity! This versatile property offers an affordable buy-in with multiple possibilities. Just removed from the heart of Readsboro, the home is privately tucked away with a peaceful yard perched above the Deerfield River.The upper level features an inviting open-concept living area filled with natural light. Sliding glass doors open to a spacious deck — the perfect spot to relax

  Flex Realty Group Flex Realty

  48 Canal Dr, Readsboro, VT 05350
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  /4

  $400,000

  • Land
  • 8.01 Acres
  • $49,938 per Acre

  248 French Hollow Rd, Winhall, VT 05340

  Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

  Kim Morgan-Wohler Wohler Realty Group

  248 French Hollow Rd, Winhall, VT 05340
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  /40

  $1,025,000

  • 4 Beds
  • 2.5 Baths
  • 3,086 Sq Ft

  19 Roundtree Rd, Bondville, VT 05340

  This rare offering, located in the North Brookwood neighborhood at the Stratton Mountain Resort, presents an opportunity to secure your legacy winter home and enjoy the revenue of a $38,000 seasonal tenant and also benefit from a tax adjustment at closing. Don't overlook the benefits this property offers. Located on Stratton Mountain Resort with shuttle and near the ski trails, this four-bedroom,

  Kim Morgan-Wohler Wohler Realty Group

  19 Roundtree Rd, Bondville, VT 05340
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  /3

  $109,000

  • Land
  • 17 Acres
  • $6,412 per Acre

  00 Bill T Dr, Readsboro, VT 05350

  Escape to the Green Mountains with this beautiful 17-acre parcel located at the end of a town-maintained road in scenic Readsboro, Vermont. This private property offers the perfect mix of seclusion and convenience, surrounded by nature and outdoor recreation opportunities. At the rear of the property, you’ll find a serene beaver pond that attracts moose, birds, and other local wildlife—an ideal

  Samantha Decker Deerfield Valley Real Estate

  00 Bill T Dr, Readsboro, VT 05350
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  /24

  $471,000

  • 3 Beds
  • 2 Baths
  • 1,357 Sq Ft

  102 Mccormick Ln, Sunderland, VT 05250

  Built in 2003, the home's open-concept design is highlighted by a bright and airy living/dining/kitchen area, where large windows flood the space with abundant natural light. A cozy pellet stove provides warmth and ambiance for those crisp Vermont evenings. The functional layout features two comfortable bedrooms and a full bathroom on the main level, while the private primary ensuite bedroom

  Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

  102 Mccormick Ln, Sunderland, VT 05250
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  /9

  $60,000

  536 Mill Rd, Stamford, VT 05352

  This house had a house fire a little less than 2 years ago. The structure there can possibly be rebuilt. Buyer would need to check with the town of Stamford about a new build. Buyers agent to verify all information. The barn is still standing and there is a shed across the street.

  Regina Perrotto Skihome Realty

  536 Mill Rd, Stamford, VT 05352
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  /10

  $14,999

  • Land
  • 1 Acre
  • $14,999 per Acre

  0 Oberhugel Rd, Readsboro, VT 05350

  1-acre generally flat and densely wooded building lot in Alpenwald Village in Stamford, VT. This is a very well maintained district with lots of privacy and the neighbors widely spread out on their own acreage, yet there's still a friendly neighborhood feel. Speaking of privacy, the rear boundary is the large southern portion of the 420,000-acre Green Mountain National Forest. Stare off your back

  David White OwnerEntry.com

  0 Oberhugel Rd, Readsboro, VT 05350
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  /2

  $425,000

  • Land
  • 3 Acres
  • $141,667 per Acre

  lot A Forest Pond Rd, Dorset, VT 05251

  Private Dorset West Road Location... private road... nearby Manchester and Dorset. Ready to build. Waste Water permit in place for 5 BR, 8 person occupancy.

  Charles Mauro Josiah Allen Real Estate, Inc.

  lot A Forest Pond Rd, Dorset, VT 05251
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  /2

  $425,000

  • Land
  • 3 Acres
  • $141,667 per Acre

  lot B Frost Pond Rd, Dorset, VT 05251

  Private but not remote. Dorset West Road Location nearby Dorset and Manchester. Nice mountain views.Waste water permit in place for 5 BR, 8 person occupancy.

  Charles Mauro Josiah Allen Real Estate, Inc.

  lot B Frost Pond Rd, Dorset, VT 05251
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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
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  /17

  $65,000

  • Land
  • 2.38 Acres
  • $27,311 per Acre

  0 Sunset Hill Rd Unit B, Pownal, VT 05261

  Motivated sellers welcome you 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

  Terri Edgerley Edge Realty Vermont

  0 Sunset Hill Rd Unit B, Pownal, VT 05261
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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
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  /54

  $675,000

  • 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
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  /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
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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
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  /6

  $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
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  /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
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  /30

  $599,000

  • 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
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  /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
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  /40

  $198,000

  • 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). Unit 1 on the

  Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
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  /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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  /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
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  /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
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  /40

  $825,000

  • 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 floor

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  2677 Route 30, Dorset, VT 05251
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  /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

  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

Showing Results 41 - 80, Page 2 of 5