Bennington County, VT Homes

• 

  

  

  /18

  Est $212,161 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,361 Sq Ft

  43 Buck Hill Rd, Shaftsbury, VT 05262

  43 Buck Hill Rd, Shaftsbury, VT 05262
• 

  

  

  /21

  $239,900

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  905 Vt Route 9, Woodford, VT 05201

  Just east of downtown Bennington, this well-maintained 3-bedroom, 1-bath ranch offers easy single-level living in a desirable Woodford location with quick access to nearby amenities, southern Vermont destinations, and major routes into neighboring states. Recent improvements over the past five years include newer windows, doors, roof, appliances, and a renovated kitchen and bath, making the home

  Jeffrey Dorman

  905 Vt Route 9, Woodford, VT 05201
• 

  

  

  /42

  $229,900 Sold Oct 20, 2025

  • 1,274 Sq Ft
  • $180/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1860

  414 Park St, Bennington, VT 05201

  Enjoy the beautiful gardens and yard of this 3 bedroom, 1 and a half bath home. Offering country kitchen, formal dining room with built-ins, living room and more. Outside the park like grounds and location make this a must see home. Across the road is the town duck pond and it's a short walk to the high school and ball parks.

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  414 Park St, Bennington, VT 05201
• 

  

  

  /12

  Est $331,105 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,123 Sq Ft

  140 Church St, Shaftsbury, VT 05262

  140 Church St, Shaftsbury, VT 05262
• 

  

  

  /18

  $300,000

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

  940 Gage St, Bennington, VT 05201

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

  Christine Lewis Brattleboro Area Realty

  940 Gage St, Bennington, VT 05201
• 

  

  /59

  $300,000 Sold Oct 20, 2025

  • 890 Sq Ft
  • $337/SF
  • 10 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1865

  3606 Kent Hollow Rd, Rupert, VT 05776

  The details, craftsmanship and enchanting +/-9 surveyed acre setting is right out of a fairy tale. A perfect Vermont getaway retreat with the sounds of Oven Brook at your door- complete with foot bridge to your own back meadow where you can take in the views overlooking the gorgeous Kent Hollow setting. The c1865 antique cabin is loaded with character – wide-plank “bow-tie” floors, log doors

  Scott McChesney McChesney RE, Inc.

  3606 Kent Hollow Rd, Rupert, VT 05776
• 

  

  /16

  Est $229,149 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  102 Meadow Ln, Shaftsbury, VT 05262

  102 Meadow Ln, Shaftsbury, VT 05262
• 

  

  /10

  $18,500

  • Land
  • 2.3 Acres
  • $8,043 per Acre

  lot139&140 Bergrucken Ln, Readsboro, VT 05350

  Discover your own piece of Vermont paradise in this picturesque double building lot. Surrounded by the scenic Green Mountains with stunning views, this peaceful setting is perfect for your dream home/getaway. Located near top ski areas and a short drive to North Adams MA, where you can enjoy easy access to cultural attractions like MASS MoCA. Embrace the tranquility of nature while staying close

  Christine Girard STEEPLEVIEW REALTY - N. ADAMS

  lot139&140 Bergrucken Ln, Readsboro, VT 05350
• 

  

  /41

  $410,000 Sold Oct 17, 2025

  • 1,792 Sq Ft
  • $229/SF
  • 14 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  882 East Rd, Bennington, VT 05201

  Welcome to 882 East Road! This spacious first-floor ranch, set on 1.97 acres, offers comfort, convenience, and room to grow. Built in 2002, the home features three bedrooms and two and half baths, all thoughtfully designed for easy single level living.The open kitchen provides plenty of working space, a beautiful pantry, and excellent flow into a large living room, perfect for gathering and

  Brooke Thomson Drew Mahar McCarthy Real Estate

  882 East Rd, Bennington, VT 05201
• 

  

  /24

  Est $252,239 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,188 Sq Ft

  855 Vt Route 7a, Shaftsbury, VT 05262

  855 Vt Route 7a, Shaftsbury, VT 05262
• 

  

  /3

  $329,000

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

  1347 Morse Hill Rd, Dorset, VT 05251

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

  Deborah Hanst

  1347 Morse Hill Rd, Dorset, VT 05251
• 

  

  /53

  $495,000 Sold Oct 17, 2025

  • 2,746 Sq Ft
  • $180/SF
  • 4 Days On Market

  • Built 1986

  200 Applewood Ln, Manchester Center, VT 05255

  TWO UNITS: ESTIMATED GROSS REVENUE: $60,000! Live in this sweet and tidy Manchester home and let the private duplex apartment with its own private porch pay your mortgage. Enjoy this carefree living in the main body of the house, with a beautiful peaked ceiling parlor with light on three sides, opening onto the garden deck. Enjoy the adjoining living room and nicely proportioned dining room off

  Zachary Zupan EXP Realty

  200 Applewood Ln, Manchester Center, VT 05255
• 

  

  /17

  Est $241,181 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  591 Vt Route 67 E, Shaftsbury, VT 05262

  591 Vt Route 67 E, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /30

  $171,000 Sold Oct 17, 2025

  • 1,724 Sq Ft
  • $99/SF
  • 177 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1979

  14 Pace Rd, Bennington, VT 05201

  One level living on a 1.1 acre level lot. Adequately sized with functional layout, this ranch style home features 3 bedrooms, 1 full bathroom, spacious living area and a full basement!The seller does not accept blind offers or escalation clauses.Cash offers require 10% EMD or $1,000 minimum, whichever is greater, and all financed offers require 1% EMD or $1,000 minimum, whichever is

  Dick Thackston R.H. Thackston & Company

  14 Pace Rd, Bennington, VT 05201
• 

  

  /34

  Est $371,980 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,771 Sq Ft

  191 Grove Rd, Shaftsbury, VT 05262

  191 Grove Rd, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /43

  $360,000 Sold Oct 17, 2025

  • 3,924 Sq Ft
  • $92/SF
  • 89 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2001

  410 Tudor Rd, Arlington, VT 05250

  Triple Mountain Views! The wrap-around decks and expansive views will impress any nature lover. This home offers hardwood floors, Vermont marble countertops, and an abundance of windows and light paired with interesting architectural design. Around every turn, you will be surprised by space and contemporary architecture. Re-built in 2011, offering two bedrooms and three baths with a walk-out

  Margretta Fischer Wohler Realty Group

  410 Tudor Rd, Arlington, VT 05250
• 

  

  /39

  Est $238,812 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,146 Sq Ft

  192 Grove Rd, Shaftsbury, VT 05262

  192 Grove Rd, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /53

  $345,000 Sold Oct 16, 2025

  • 1,708 Sq Ft
  • $202/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1963

  14 Crescent Ln, Bennington, VT 05201

  An Idyllic Ranch Retreat with 235 Feet of beautiful shoreline totaling 1.3 Acres . This 2 bedroom ranch home has great water views from every room. . The large, bright primary bedroom is a sanctuary unto itself. Imagine waking each morning to the tranquil sight of lake waters stretching beyond the window, or slipping into the adjoining hot tub room for a restorative soak. This unique space leads

  Dan Mason Perrott Realty

  14 Crescent Ln, Bennington, VT 05201
• 

  

  /20

  Est $380,810 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  136 Grove Rd, Shaftsbury, VT 05262

  136 Grove Rd, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /50

  $419,000 Sold Oct 16, 2025

  • 1,941 Sq Ft
  • $216/SF
  • 85 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1872

  97 Buck Hill Rd, Shaftsbury, VT 05262

  Two homes on 4.67 acres in Shaftsbury, VT! This village home offers a rare opportunity indeed by including a separate 2 bedroom ranch home as well. The main home is a charming New England farmhouse with 3 bedrooms and 2 bathrooms, living room, formal dining room, kitchen, main level laundry and so much more. The accessory dwelling unit offers 2 bedrooms, 1 bathroom, eat-in kitchen and living

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  97 Buck Hill Rd, Shaftsbury, VT 05262
• 

  

  /36

  Est $369,829 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  374 North Rd, Shaftsbury, VT 05262

  374 North Rd, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /21

  $300,000 Sold Oct 16, 2025

  • 1,365 Sq Ft
  • $220/SF
  • 77 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1988

  339 Chester Knoll Dr, Bennington, VT 05201

  A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings.Chester Knoll provides an

  Lori Hurley Four Corner Properties LLC

  339 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /27

  Est $263,308 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  338 Twitchell Hill Rd, Shaftsbury, VT 05262

  338 Twitchell Hill Rd, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /15

  $380,000 Sold Oct 15, 2025

  • Land
  • 16 Acres
  • $23,750 per Acre

  • 0 Days On Market

  0 Tower Rd Unit 28, Dorset, VT 05251

  Very Private Wooded Parcel off of Tower Road sharing a drive with the neighbor... Mountain Views... borders Green Mountain National Forrest...a great 16 acre residential parcel that supports quiet enjoyment of Dorset's quiet end of the Dorset Hollow Location. The 4 BR VT WW permit is in place. A well exists on the property... rough drive in place. Woods roads and an easement exists on

  Laura Beckwith Josiah Allen Real Estate, Inc.

  0 Tower Rd Unit 28, Dorset, VT 05251
• 

  

  /39

  Est $570,070 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,892 Sq Ft

  553 Daniels Rd, Shaftsbury, VT 05262

  553 Daniels Rd, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /30

  $400,000 Sold Oct 15, 2025

  • 1,616 Sq Ft
  • $248/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  38 Spruce Ln, Arlington, VT 05250

  Discover this updated 3-bedroom, 2-bath home in the heart of Arlington, Vermont. The main level features a newly added primary suite with its own full bath. Recent upgrades include new windows in all three bedrooms, living room, and dining room, enhancing both comfort and energy efficiency.Outside, a brand-new 24x24 two-car garage provides ample space for vehicles and features a second-story

  Lori Hurley Four Corner Properties LLC

  38 Spruce Ln, Arlington, VT 05250
• 

  

  /39

  Est $400,237 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,586 Sq Ft

  20 Eastview Dr, Shaftsbury, VT 05262

  20 Eastview Dr, Shaftsbury, VT 05262
• 

  

  /54

  $245,000

  • 3 Beds
  • 1 Bath
  • 1,064 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
• 

  

  /47

  $455,555 Sold Oct 15, 2025

  • 3,024 Sq Ft
  • $151/SF
  • 9 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  380 Suncrest Rd, Rupert, VT 05776

  Property is HUD owned. CASE# 531-029113. Located in a picturesque yet rural location sits this large home on large 10 acre lot with barns and detached garage. Room to roam, have animals, a garden; so many possibilities. 3+ bedroom, 3 bathroom 2 story home!

  Dick Thackston R.H. Thackston & Company

  380 Suncrest Rd, Rupert, VT 05776
• 

  

  /36

  Est $493,768 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,116 Sq Ft

  1530 Trumbull Hill Rd, Shaftsbury, VT 05262

  1530 Trumbull Hill Rd, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /49

  $929,500 Sold Oct 15, 2025

  • 3,400 Sq Ft
  • $273/SF
  • 14 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1995

  681 Powderhorn Rd, Manchester Center, VT 05255

  Enjoy privacy and convenience in this charming New England country home, just minutes from town. An open floor plan connects the updated country kitchen to the dining area and living room which features a fireplace and beamed cathedral ceiling. A large mud room with built in storage benches and a farmhouse sink has doors to the stone patio. In the living room, french doors open to a screened

  Christiane Carroccio TPW Real Estate

  681 Powderhorn Rd, Manchester Center, VT 05255
• 

  

  /33

  Est $667,922 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,145 Sq Ft

  2005 Trumbull Hill Rd, Shaftsbury, VT 05262

  2005 Trumbull Hill Rd, Shaftsbury, VT 05262

Showing Results 241 - 280, Page 7 of 18