Bennington County VT Homes for Sale

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  /38

  $575,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14A Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here.Step inside and discover an open floor plan that feels both spacious and inviting

  Julie Citron RE/MAX Four Seasons

  14A Marisa Ln, Dorset, VT 05251
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  /29

  $250,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft

  103 Jennings Brook Dr, Bennington, VT 05201

  Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

  Kelley Mccarthy Mahar McCarthy Real Estate

  103 Jennings Brook Dr, Bennington, VT 05201
• 

  

  

  /46

  $1,275,000

  • 4 Beds
  • 2.5 Baths
  • 4,084 Sq Ft

  1677 Barnumville Rd, Manchester Center, VT 05255

  Imagine a time where taverns were the heart of the community, where laughter echoed off thick brick walls and stories were told by firelight. Now see yourself enjoying the ease of Single Floor Living that includes an enormous primary ensuite, with laundry! Start your day in the completely updated kitchen and move effortlessly into the dining area and living room with an easy to light cozy propane

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  1677 Barnumville Rd, Manchester Center, VT 05255
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  /11

  $169,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 848 Sq Ft

  302 U S 7 S, Woodford, VT 05201

  Over 3 acres, a brook and lots of woods for walking. Room for a terraced garden, tons of parking and minutes to Bennington! This 2 bedroom ranch style home has a huge eat in kitchen and a lovely big living room with lots of windows. There is a bonus sun room with laundry. Owners are using an attached shed as a chicken coop! Sweet find at this affordable price!

  Christine Lewis Brattleboro Area Realty

  302 U S 7 S, Woodford, VT 05201
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  /3

  $475,000

  • Land
  • 12.82 Acres
  • $37,051 per Acre

  22 Morse Rd, Bennington, VT 05201

  Positioned in the heart of Bennington’s commercial corridor on 12.82 open acres, 22 Morse Road present a prime development opportunity. Offering excellent visibility and accessibility along one of the area’s primary commercial arteries, the property is ideally situated for a variety of commercial, retail, service, mixed-use, or redevelopment possibilities. The location provides convenient access

  Paul Carroccio TPW Real Estate

  22 Morse Rd, Bennington, VT 05201
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  /33

  $265,000

  $34K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  8 West St, Bennington, VT 05201

  Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  8 West St, Bennington, VT 05201
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  /36

  $609,900

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  23 Stonewall Ln, Dorset, VT 05251

  Nestled in one of Vermont's most coveted villages, this three-bedroom, two-bathroom home is a canvas waiting for your creative vision. Priced well below assessed value, this property represents a rare opportunity to build equity from day one while enjoying the charm of quintessential New England living.The generous lot gives you room to breathe, garden, or simply watch the seasons paint

  Brian Hill Remax Summit

  23 Stonewall Ln, Dorset, VT 05251
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  /60

  $180,000

  $20K PRICE DROP

  • Land
  • 58.1 Acres
  • $3,098 per Acre

  1073 Chapel Rd, Bennington, VT 05201

  Unlock the potential of this spectacular 58.1 +/- acre woodland property in historic Bennington. The groundwork for your future home or getaway is already laid with a State-approved wastewater permit in place for a three-bedroom single-family residence, allowing you the flexibility to design your build. Further simplifying your plans, the property offers the rare advantage of connecting to the

  Curtis Trousdale Preferred Properties

  1073 Chapel Rd, Bennington, VT 05201
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  /41

  $299,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  509 Thompson Pond Rd, Pownal, VT 05261

  Discover Your Perfect Getaway at Verdmont If you're a nature enthusiast, a rare and exclusive opportunity awaits at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this gated community spans nearly 500 acres of unspoiled wilderness-a true haven for outdoor living.As a shareholder, you'll enjoy a wealth of amenities: Water & Land Privileges: Two stunning

  Kelley Mccarthy Mahar McCarthy Real Estate

  509 Thompson Pond Rd, Pownal, VT 05261
• 

  

  /20

  $475,000

  $24K PRICE DROP

  • 6 Beds
  • 6 Baths
  • 9,000 Sq Ft

  425 Main St, Bennington, VT 05201

  15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

  Chris Long BHG Masiello Brattleboro

  425 Main St, Bennington, VT 05201
• 

  

  /60

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,295 Sq Ft

  142 Schenkar Rd, Pownal, VT 05261

  Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

  Erin McCormick KW Vermont

  142 Schenkar Rd, Pownal, VT 05261
• 

  

  /23

  $219,000

  $16K PRICE DROP

  • 1,860 Sq Ft

  205 County St, Bennington, VT 05201

  This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family. use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 2-bedroom and 3-bedroom units, this property is designed to adapt to

  Dan Mason Perrott Realty

  205 County St, Bennington, VT 05201
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  /27

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,075 Sq Ft

  1083 Main St, Bennington, VT 05201

  Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  1083 Main St, Bennington, VT 05201
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  /7

  $55,000

  • Land
  • 22,215 Sq Ft
  • $107,843 per Acre

  24 Asa Way, Bennington, VT 05257

  Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience.Public water and sewer are available,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  24 Asa Way, Bennington, VT 05257
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  /5

  $55,000

  • Land
  • 20,908 Sq Ft
  • $114,583 per Acre

  29 Asa Way, Bennington, VT 05257

  Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home.Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process.

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  29 Asa Way, Bennington, VT 05257
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  /24

  $215,000

  $20K PRICE DROP

  • 1,300 Sq Ft

  340 Pleasant St, Bennington, VT 05201

  Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

  Melissa Nebelski Real Broker LLC

  340 Pleasant St, Bennington, VT 05201
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  /37

  $575,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14 Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here.Step inside and discover an open floor plan that feels both spacious and inviting

  Julie Citron RE/MAX Four Seasons

  14 Marisa Ln, Dorset, VT 05251
• 

  

  /55

  $2,850,000

  New Construction $100K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,762 Sq Ft

  59 Garden Loop Rd, Winhall, VT 05340

  JULY 23 - Significant new price change today! - Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual laundry

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  59 Garden Loop Rd, Winhall, VT 05340
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  /12

  $64,000

  $11K PRICE DROP

  • Land
  • 13.01 Acres
  • $4,919 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
• 

  

  /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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  /14

  $104,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  347 Hickory Rd, Bennington, VT 05201

  Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

  William Paquin Maple Leaf Real Estate

  347 Hickory Rd, Bennington, VT 05201
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  /43

  $319,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  683 Water St, North Bennington, VT 05257

  Much larger than it looks and completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
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  /25

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  393 Morse Hill Rd, East Dorset, VT 05253

  This beautifully maintained Dorset home with views is ready for its new owners. The main level features a generously sized eat-in kitchen with granite countertops that opens into the dining room. This floor also includes a large living room, a bedroom, and French doors that lead to a spacious deck overlooking a private yard. The ground floor offers a primary bedroom, a bathroom, and a laundry

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  393 Morse Hill Rd, East Dorset, VT 05253
• 

  

  /45

  $269,000

  $26K PRICE DROP

  • 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
• 

  

  /15

  $85,000

  $15K PRICE DROP

  • Land
  • 1.2 Acres
  • $70,833 per Acre

  23 Moose Hollow Rd, Winhall, VT 05340

  Beautiful parcel located in a highly desirable Winhall neighborhood, just minutes to Bromley and Stratton Mountains, and a short drive to Manchester’s shops and dining. This property offers a State of Vermont potable water supply and wastewater permit in place for a 4-bedroom home. The lot is cleared and ready for construction; an ideal opportunity to build your Vermont retreat.

  Carrie Mathews Winhall Real Estate

  23 Moose Hollow Rd, Winhall, VT 05340
• 

  

  /43

  $1,250,000

  $245K PRICE DROP

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

  50 Grouse Ln, Dorset, VT 05251

  Custom built Dorset Hollow estate offered for the first time since 1998. Perfectly situated on 10 private acres abutting 3,200 acres of conservation land, this 5,100 sq ft residence combines timeless quality, fine finishes, and Vermont mountain charm. Designed for comfort and entertaining, the home features 4 bedrooms, 5 bathrooms, and an attached 2-car garage. Elegant details include four

  David Halligan Four Seasons Sotheby's Int'l Realty

  50 Grouse Ln, Dorset, VT 05251
• 

  

  /47

  $2,850,000

  $150K PRICE DROP

  • 2 Beds
  • 3.5 Baths
  • 5,731 Sq Ft

  2334 Morse Hill Rd, Dorset, VT 05251

  Beautiful Dorset Contemporary Offering Privacy, Comfort, and Easy Living. If you’ve been looking for a private Vermont retreat with room to relax, entertain, and enjoy the beauty of every season, this exceptional custom home may be the perfect fit. Built in 1996 by respected Dorset builder Keith Dodson, this thoughtfully designed 5,731 sq. ft. contemporary sits on 12.15 peaceful acres with a pond

  David Halligan Four Seasons Sotheby's Int'l Realty

  2334 Morse Hill Rd, Dorset, VT 05251
• 

  

  /47

  $845,000

  • 5 Beds
  • 5.5 Baths
  • 3,875 Sq Ft

  1629 Mann Hill Rd N, Pownal, VT 05261

  Facing west to capture breathtaking mountain views and unforgettable sunsets from nearly every room, this exceptional modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors, cozy alcoves, and original beams in the living room create a warm and inviting atmosphere throughout. The spacious floor plan features five generously sized bedrooms, each with its

  Kelley Mccarthy Mahar McCarthy Real Estate

  1629 Mann Hill Rd N, Pownal, VT 05261
• 

  

  /60

  $799,000

  $76K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,462 Sq Ft

  636 Dexter Rd, Shaftsbury, VT 05262

  The Dexter Road Farmhouse, Circa 1800In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write “Stopping by the Woods on a Snowy Evening." Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region.

  

  Kristin Comeau

  TPW Real Estate

  636 Dexter Rd, Shaftsbury, VT 05262
• 

  

  /45

  $525,000

  $40K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,594 Sq Ft

  191 Pleasant Street Extension, East Dorset, VT 05253

  "COME TAKE A PEEK, IT'S JUST ACROSS THE CREEK.....Enjoy an inviting front porch to unwind and breathe in the serene surroundings! Unwind and take in the lovely mountain views, all set on the scenic Tom River in East Dorset! Charming saltbox style (1982 circa), the design is open living spaces with abundant light through out... As an added bonus this property boasts an over sized two car garage

  Sunny Breen Josiah Allen Real Estate, Inc.

  191 Pleasant Street Extension, East Dorset, VT 05253
• 

  

  /10

  $150,000

  • Land
  • 4 Acres
  • $37,500 per Acre

  0 Rocky Ln Unit 5082777, Dorset, VT 05253

  'THE GROUND BENEATH AN APRIL SNOWSTORM IS NOT DORMANT... IT IS AWAKENING!".... Come discover the perfect opportunity to craft the home of your dreams!! With Spring ready to bloom, this very special lot is vibrant and quite ready for your vision!Fully permitted for a five bedroom residence, this property combines privacy, natural beauty and convenience!Imagine waking up to serene views,

  Sunny Breen Josiah Allen Real Estate, Inc.

  0 Rocky Ln Unit 5082777, Dorset, VT 05253
• 

  

  /48

  $2,950,000

  $335K PRICE DROP

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

  68 Green Peak Orchard S, East Dorset, VT 05253

  Welcome to Green Peak Orchard in Dorset, Vermont, where timeless architecture and exceptional craftsmanship define this custom Greek Revival residence on 9.9 private acres. Surrounded by mature landscaping, stone walls, and slate terraces, this remarkable home blends classic New England elegance with modern comfort. Designed with meticulous attention to detail, the home features wide-plank

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

  68 Green Peak Orchard S, East Dorset, VT 05253
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  /32

  $265,000

  $10K PRICE DROP

  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
• 

  

  /31

  $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
• 

  

  /7

  $997,000

  • Land
  • 23,086 Sq Ft
  • $1,881,132 per Acre

  153 Northside Dr, Bennington, VT 05201

  Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

  Lori Hurley Four Corner Properties LLC

  153 Northside Dr, Bennington, VT 05201
• 

  

  /60

  $1,600,000

  • 5 Beds
  • 4.5 Baths
  • 4,243 Sq Ft

  397 Fern Hill, Dorset, VT 05251

  Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

  Laura Beckwith Josiah Allen Real Estate, Inc.

  397 Fern Hill, Dorset, VT 05251
• 

  

  /13

  $275,000

  $20K PRICE DROP

  • 2,022 Sq Ft

  124 S Branch St, Bennington, VT 05201

  Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street.

  Julie Glover Mahar McCarthy Real Estate

  124 S Branch St, Bennington, VT 05201
• 

  

  /9

  $269,000

  $26K PRICE DROP

  • 2,206 Sq Ft

  116 S Branch St Unit 118, Bennington, VT 05201

  Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

  Julie Glover Mahar McCarthy Real Estate

  116 S Branch St Unit 118, Bennington, VT 05201
• 

  

  /23

  $329,900

  $20K PRICE DROP

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

  773 Oberdorf Rd, Readsboro, VT 05350

  Discover cozy mountain living in this charming Alpenwald chalet, where rustic character meets thoughtful modern updates. Nestled among the trees, this inviting retreat offers a bright, open floor plan filled with natural light from expansive windows and sliding glass doors. Recently remodeled, the kitchen and both full bathrooms bring a fresh, updated feel, while a comfortable bar area adds the

  Sean Taylor Moresi Real Estate Partners

  773 Oberdorf Rd, Readsboro, VT 05350
• 

  

  /36

  $198,000

  $22K PRICE DROP

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

  399 Bard Rd, Bennington, VT 05201

  Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level

  Curtis Trousdale Preferred Properties

  399 Bard Rd, Bennington, VT 05201

Showing Results 161 - 200, Page 5 of 7