Bennington, VT Homes

• 

  

  

  /20

  $90,000 Sold Apr 17, 2025

  • 1,520 Sq Ft
  • $59/SF
  • 4 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1903

  105 Spring St, Bennington, VT 05201

  Side-by-side duplex situated in the heart of Bennington. Great investment potential. Rent both units and generate a nice income flow, or occupy one side and rent the other to help cover the mortgage. Property could also be converted into a single-family residence. Unit 1 offers first floor living room, dining room and kitchen, bright sunroom off the back, with two bedrooms and a full bath

  Matt Waddington Hoffman Real Estate

  105 Spring St, Bennington, VT 05201
• 

  

  

  /40

  Est $289,093 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,000 Sq Ft

  38 Center St, Bennington, VT 05201

  38 Center St, Bennington, VT 05201
• 

  

  

  /22

  $139,000

  • 4 Beds
  • 1 Bath
  • 1,262 Sq Ft

  101 Morgan St, Bennington, VT 05201

  Motivated seller.!!! Move in asd add your finishing touches to this Antique House located in Downtown on a generous corner. This 2 story, 4 bedroom, 1 bath Bennington home has great character featuring a Dutch front door, enclosed front porch, and beautiful bay window. Property has an eat-in kitchen, dinning room, laundry room with washer and dryer, living room, basement, and den! Enjoy being

  Dan Mason Perrott Realty

  101 Morgan St, Bennington, VT 05201
• 

  

  

  /51

  $395,000 Sold Apr 03, 2025

  • 4,992 Sq Ft
  • $79/SF
  • 5 Days On Market

  • 8 Beds
  • 4 Baths
  • Built 1915

  301 North St Unit 3, Bennington, VT 05201

  Five unit investment property in great condition. All units are 2 bedrooms, 1 bath, include kitchen appliances, laundry hookups, heat, hot water, trash removal, lawn care, plowing and parking. Close to downtown Bennington, it's a short walk to numerous dining establishments, as well as prominent employers (Vermont Veterans Home, state office complex, and several schools). Apartments are rented

  Jenifer Prouty Hoffman Hoffman Real Estate

  301 North St Unit 3, Bennington, VT 05201
• 

  

  

  /31

  Est $279,256 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  43 Cyr Ct, Bennington, VT 05201

  43 Cyr Ct, Bennington, VT 05201
• 

  

  /54

  $215,000

  • 4 Beds
  • 3 Baths
  • 2,162 Sq Ft

  304 North St Unit 6, Bennington, VT 05201

  Great Investment Opportunity! This well-maintained 3-unit property is a fantastic opportunity for savvy investors. Two of the units are currently rented, providing immediate income potential. Situated just a short stroll from downtown, you'll find charming shops, popular restaurants, and close proximity to the Bennington trail system—perfect for outdoor enthusiasts. Just 1 hour from Albany and

  Thomas Martins Maple Leaf Realty

  304 North St Unit 6, Bennington, VT 05201
• 

  

  /33

  $200,000 Sold Mar 14, 2025

  • 1,788 Sq Ft
  • $112/SF
  • 291 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1890

  203 Scott St, Bennington, VT 05201

  PRICE IMPROVEMENT! Exterior improvements include new siding, windows, roof and inside, electrical, plumbing and new flooring! WOW! This 4 bedroom, 1 1/2 bath in-town gem is move-in ready with modern and efficient updates. Full bathroom and laundry room conveniently located on the first floor. Spacious layout with a first-floor bonus room which could serve as a main floor bedroom or home office.

  Cassie Barbeau Mahar McCarthy Real Estate

  203 Scott St, Bennington, VT 05201
• 

  

  /18

  Est $239,953 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  118 Tel Rd, Bennington, VT 05201

  118 Tel Rd, Bennington, VT 05201
• 

  

  /58

  $269,000

  • 7 Beds
  • 4 Baths
  • 4,417 Sq Ft

  200 Depot St, Bennington, VT 05201

  Own a piece of Bennington history! Alex Drysdale House, c. 1850. The grocery store (formerly 138 River Street) operated under the name "A. Drysdale & Son" and was built in 1876. Today this historic property is set up as a four-unit with great income potential. It currently houses three apartments: a freshly renovated four bedroom (used as an Airbnb), three bedroom, and efficiency, along with the

  Justine Curry Maple Leaf Realty

  200 Depot St, Bennington, VT 05201
• 

  

  /30

  $270,000 Sold Mar 07, 2025

  • 1,712 Sq Ft
  • $158/SF
  • 72 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  402 Jefferson Heights, Bennington, VT 05201

  Situated in a lovely neighborhood on a nicely landscaped lot sits this 3 bedroom 2 bath home. 1 car garage under, two paved driveways, back deck and enclosed porch, lower level family room and more! Are you looking for a place to call home? This could be it!

  Dick Thackston R.H. Thackston & Company

  402 Jefferson Heights, Bennington, VT 05201
• 

  

  /38

  Est $278,876 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,802 Sq Ft

  116 Rutter Rd, Bennington, VT 05201

  116 Rutter Rd, Bennington, VT 05201
• 

  

  /42

  $1,950,000

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

  Chris DeFelice Four Seasons Sotheby's Int'l Realty

  1086 West Rd, Bennington, VT 05201
• 

  

  /19

  $285,000 Sold Feb 21, 2025

  • 3,960 Sq Ft
  • $72/SF
  • 191 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1880

  119 Dewey St, Bennington, VT 05201

  Discover this beautifully updated three-unit property, originally built in 1880. Featuring gorgeous hardwood floors throughout, this well-maintained building offers two units with newly renovated kitchens and one unit with an updated bathroom, providing a perfect blend of classic charm and modern convenience.Conveniently located close to downtown, you'll enjoy easy access to a variety of

  Brooke Thomson Drew Mahar McCarthy Real Estate

  119 Dewey St, Bennington, VT 05201
• 

  

  /26

  Est $237,369 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,760 Sq Ft

  107 Rutter Rd, Bennington, VT 05201

  107 Rutter Rd, Bennington, VT 05201
• 

  

  /48

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 3,742 Sq Ft

  34 Southshire Dr, Bennington, VT 05201

  Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all enhanced by

  Kelley Mccarthy Mahar McCarthy Real Estate

  34 Southshire Dr, Bennington, VT 05201
• 

  

  /39

  $299,000 Sold Feb 13, 2025

  • 2,824 Sq Ft
  • $106/SF
  • 101 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1977

  152 Apple Hill Rd, Bennington, VT 05201

  This contemporary style home sits on 1.21 acres in a desirable Bennington neighborhood. Close to town yet far enough away to be out of the hustle and bustle. This home could welcome mutli-generational living as well as anyone looking for extra space. The first floor has 3 bedrooms, two of which have their own half bath. This level also has a full handi-cap accessible bathroom as well as a

  Catherine Cairns Maple Leaf Realty

  152 Apple Hill Rd, Bennington, VT 05201
• 

  

  /38

  Est $224,282 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  5 Tel Rd, Bennington, VT 05201

  5 Tel Rd, Bennington, VT 05201
• 

  

  /7

  $175,000

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

  00 Silk Rd, Bennington, VT 05201

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

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
• 

  

  /40

  $250,000 Sold Feb 11, 2025

  • 900 Sq Ft
  • $278/SF
  • 45 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  1016 County St, Bennington, VT 05201

  Completely renovated Cottage Style 3 bed 1 bath home at the edge of town. Located on the Roaring Branch of the Walloomsac river. New heating system, public water and sewer. All new appliances. Just a short walk to the Blue Trail, and the Bennington Recreation Center, All this near public transportation, Mt Anthony Schools. Nothing left to do but move in and enjoy this beautifully renovated home.

  Edward Jones Josiah Allen Real Estate, Manchester Branch Office

  1016 County St, Bennington, VT 05201
• 

  

  /40

  Est $233,016 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  316 Beech St, Bennington, VT 05201

  316 Beech St, Bennington, VT 05201
• 

  

  /52

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities.

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
• 

  

  /35

  $252,600 Sold Feb 10, 2025

  • 1,756 Sq Ft
  • $144/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1890

  222 Bradford St, Bennington, VT 05201

  Welcome home and let your home work for you! This in-town, cozy New Englander is currently set up as a single family home with 4-5 bedrooms but could be easily converted back to a 2, 2 bedroom, multi-family as an income generating property or owner occupied residence with a rental to help with your mortgage! The property boasts a 4 car garage, which is partially rented out and also generates

  Abi Gregorio

  222 Bradford St, Bennington, VT 05201
• 

  

  /17

  Est $119,976 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,709 Sq Ft

  224 Beech St, Bennington, VT 05201

  224 Beech St, Bennington, VT 05201
• 

  

  /39

  $297,500

  • 5 Beds
  • 2 Baths
  • 2,294 Sq Ft

  218 Union St, Bennington, VT 05201

  Charming Downtown Victorian - Income Opportunity Meets Timeless StyleTucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each

  Kelley Mccarthy Mahar McCarthy Real Estate

  218 Union St, Bennington, VT 05201
• 

  

  /40

  $409,900 Sold Feb 04, 2025

  • 2,905 Sq Ft
  • $141/SF
  • 49 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1978

  9 Stonehedge Dr, Bennington, VT 05201

  Experience the tranquility of a quiet residential street, yet just a short stroll to downtown shops and restaurants. Available for the first time on the market, this elegant English Tudor is a standout amongst the coveted Stonehedge neighborhood. Boasting a 40 foot chimney and extraordinary architecture, this spacious home has all you could ever want and more! Featuring a newly renovated kitchen,

  Angela Bevin Maple Leaf Realty

  9 Stonehedge Dr, Bennington, VT 05201
• 

  

  /35

  Est $208,887 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft

  218 Beech St, Bennington, VT 05201

  218 Beech St, Bennington, VT 05201
• 

  

  /12

  $575,000

  • 6 Beds
  • 4 Baths
  • 15,179 Sq Ft

  423 Main St, Bennington, VT 05201

  Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor

  Chris Long BHG Masiello Brattleboro

  423 Main St, Bennington, VT 05201
• 

  

  /32

  $195,000 Sold Jan 31, 2025

  • 1,401 Sq Ft
  • $139/SF
  • 15 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1945

  103 Evergreen Dr, Bennington, VT 05201

  Charming 3-bedroom, 1.5-bathroom home set on a generous .34-acre lot on a quiet street! Recently updated kitchen and bathroom. A spacious mudroom welcomes you as you enter. All three bedrooms are located on the second floor, while the first floor includes the living room, dining room, kitchen, a 3/4 bathroom, and a laundry room. The basement features a dedicated office space along with a

  Gabrielle Burdge Hoffman Real Estate

  103 Evergreen Dr, Bennington, VT 05201
• 

  

  /40

  Est $150,521 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 989 Sq Ft

  239 Beech St, Bennington, VT 05201

  239 Beech St, Bennington, VT 05201
• 

  

  /30

  $1,250,000

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

  77 Fuller Rd W, Bennington, VT 05201

  Experience the quintessential Vermont lifestyle at the historic Nickerson-Jewett farm. Only 5 minutes to Bennington attractions and amenities and 15 minutes to Williamstown, MA. This appealing country home is located on a town maintained dead-end road. Privately nestled on 134.46 acres of scenic beauty, the charming 4 bedroom, 2.5 bath mid nineteenth century farmstead includes a well-preserved

  Jason Saphire www.HomeZu.com

  77 Fuller Rd W, Bennington, VT 05201
• 

  

  /29

  $232,500 Sold Jan 29, 2025

  • 2,432 Sq Ft
  • $96/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1900

  649 N Branch St, Bennington, VT 05201

  Discover the perfect blend of comfort, versatility, and potential in this 3-bedroom, 2-bath home, featuring an in-law suite that can easily convert into a one-bedroom rental for added income. Set on 1.21 acres with a pond. A spacious family room and primary bedroom addition bring extra comfort and space, perfect for both relaxation and entertaining. Car enthusiasts or DIY lovers will find their

  Kelley Mccarthy Mahar McCarthy Real Estate

  649 N Branch St, Bennington, VT 05201
• 

  

  /19

  Est $116,655 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,062 Sq Ft

  235 Beech St, Bennington, VT 05201

  235 Beech St, Bennington, VT 05201
• 

  

  /5

  $2,500,000

  • Land
  • 0.88 Acre
  • $2,840,909 per Acre

  113 Depot St, Bennington, VT 05201

  Mixed use development site in the heart of Downtown Bennington. .88 acre site with Zoning, Preservation and Stormwater approvals for a 60,000 sq ft mixed use building with planned commercial occupancy on the first floor and three stories of residential occupancy above - 60 units total with 12 units of workforce housing.

  Paul Carroccio TPW Real Estate

  113 Depot St, Bennington, VT 05201
• 

  

  /26

  $160,000 Sold Jan 21, 2025

  • 948 Sq Ft
  • $169/SF
  • 142 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  432 South St Unit A2, Bennington, VT 05201

  Enjoy low maintenance living and walkability to all that downtown offers. This lovely condo that has been freshly updated within the last couple of years. There is a new carpet in the living room and mostly new appliances, including the washer and dryer in upstairs bathroom. Fresh paint throughout and custom shelving in one of the bedrooms. Efficient and comfortable condo unit ready to move right

  Lilli West Maple Leaf Realty

  432 South St Unit A2, Bennington, VT 05201
• 

  

  /37

  Est $343,272 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  163 Morgan St, Bennington, VT 05201

  163 Morgan St, Bennington, VT 05201
• 

  

  /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
• 

  

  /50

  $530,000 Sold Jan 16, 2025

  • 3,782 Sq Ft
  • $140/SF
  • 86 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1829

  3 Seminary Ln, Bennington, VT 05201

  Coveted Three Seminary Lane | Old Bennington Originally established in 1829 as Mount Anthony Seminary, this remarkable property first served as a boys' boarding school. In 1897, it transitioned to become the clubhouse of the Mount Anthony Country Club, a role it maintained well into the early 20th century. Now situated on 2.5 acres, this charming Colonial-style home exudes character and grace,

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  3 Seminary Ln, Bennington, VT 05201
• 

  

  /30

  Est $196,976 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  101 Coulter St, Bennington, VT 05201

  101 Coulter St, Bennington, VT 05201
• 

  /2

  $49,900

  • Land
  • 11 Acres
  • $4,455 per Acre

  0 Mount Anthony Rd, Bennington, VT 05201

  A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont—11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds.Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building

  Kelley Mccarthy Mahar McCarthy Real Estate

  0 Mount Anthony Rd, Bennington, VT 05201
• 

  

  /9

  $220,000 Sold Jan 10, 2025

  • 2,894 Sq Ft
  • $76/SF
  • 135 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1800

  545 Niles Rd, Bennington, VT 05201

  Located within the picturesque landscape of Southern Vermont, this extraordinary heirloom property offers a once-in-a-generation opportunity for a discerning new owner. Surrounded by a tapestry of verdant farmland, this majestic residence rests upon nearly two acres of land, providing the perfect canvas for crafting your own masterpiece in one of the region's most idyllic settings. After years of

  William Paquin Maple Leaf Realty

  545 Niles Rd, Bennington, VT 05201

Showing Results 81 - 120, Page 3 of 18