23

Bennington County VT Homes under $300,000

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  • /47

    $275,000

    • 5 Beds
    • 2 Baths
    • 2,952 Sq Ft

    569 Buck Hill Rd, Arlington, VT 05250

    Amazing 1850s farmhouse rich in old-world charm and character. Gleaming hardwood floors, large sun-filled rooms, and timeless architectural details throughout. Distinctive features include an elegant arched doorway, a unique library with octagonal bookshelves, and a striking turret that enhances the home’s historic appeal. The spacious primary bedroom stretches 25 feet and offers two separate

    Lisa Friedman Great American Dream Realty

    569 Buck Hill Rd, Arlington, VT 05250
  • /6

    $249,900

    • 4 Beds
    • 2 Baths
    • 1,512 Sq Ft

    323 Weeks St, Bennington, VT 05201

    Fixer Upper - Good Location -Conveniently close to shopping, the hospital and downtown. Rehab financing with 203K loan.

    Susan Wylie Lions on Main Realty

    323 Weeks St, Bennington, VT 05201
  • /32

    $249,000

    • 2 Beds
    • 1 Bath
    • 944 Sq Ft

    364 Oberdorf Rd Unit 153, Readsboro, VT 05350

    Charming 2-Bedroom, 1-Bath home with 2 car garage in Alpenwald Village – Your Mountain Escape Awaits! Welcome to this cozy gem nestled in the heart of Alpenwald Village, offering a perfect blend of comfort and adventure. This home is ideal for those seeking privacy, outdoor fun, and a cozy retreat from everyday life. Some of the Key Features include:An oversized 25x26 two-car garage provides

    Monique White Deerfield Valley Real Estate

    364 Oberdorf Rd Unit 153, Readsboro, VT 05350
  • /36

    $269,900

    • 3 Beds
    • 1.5 Baths
    • 900 Sq Ft

    2092 N Bennington Rd, North Bennington, VT 05257

    Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front livingroom with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    2092 N Bennington Rd, North Bennington, VT 05257
  • /49

    $275,000

    • 2 Beds
    • 1 Bath
    • 1,124 Sq Ft

    42 Overlook Rd, Pownal, VT 05261

    Tucked away in a rural setting, this 2 bedroom, 1 bath, ranch style home offers spectacular views overlooking Barber Pond. Inside, you’ll find a warm and inviting cabin style interior, complete with natural wood accents and a Vermont Castings wood stove set on a stunning stone hearth for cozy ambiance during the colder seasons. The galley style, eat-in kitchen has rustic cabinetry, water views, a

    Casey Scott Southern Vermont Realty Group

    42 Overlook Rd, Pownal, VT 05261
  • /21

    $215,000

    • 2 Beds
    • 1 Bath
    • 938 Sq Ft

    55 Eden Way Unit 3, Bennington, VT 05201

    Move right in to this immaculate 2-bedroom condo in the highly desirable Apple Ridge community! Meticulously maintained and thoughtfully cared for, this home offers effortless one-level living with nothing left to do but unpack. Step inside to discover a freshly painted interior complemented by new flooring and carpeting throughout. The bright and inviting kitchen features beautiful cabinetry and

    Angela Bevin Maple Leaf Realty

    55 Eden Way Unit 3, Bennington, VT 05201
  • /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
  • /19

    $219,500

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft

    14 Robinson Ave, Bennington, VT 05201

    Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

    Timothy Corcoran Mahar McCarthy Real Estate

    14 Robinson Ave, Bennington, VT 05201
  • /9

    $295,000

    • 4 Beds
    • 2 Baths
    • 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
  • /13

    $295,000

    • 4 Beds
    • 2 Baths
    • 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. With

    Julie Glover Mahar McCarthy Real Estate

    124 S Branch St, Bennington, VT 05201
  • /23

    $249,000

    • Land
    • 17.6 Acres
    • $14,148 per Acre

    88 Cedar Ln, Peru, VT 05152

    Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

    Joe Castaluccio Winhall Real Estate

    88 Cedar Ln, Peru, VT 05152
  • /12

    $299,999

    • Land
    • 10.05 Acres
    • $29,851 per Acre

    00 Garden Loop Rd, Winhall, VT 05340

    The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

    David White OwnerEntry.com

    00 Garden Loop Rd, Winhall, VT 05340
  • /45

    $295,000

    • 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
  • /16

    $205,000

    • 1 Bed
    • 1 Bath
    • 784 Sq Ft

    40 Bourn Brook Rd Unit 50, Manchester, VT 05255

    Modern In-Town Living and Fully Renovated Bourn Brook Condo. Experience the best of Manchester Center in this meticulously renovated end-unit at Bourn Brook. Whether you are looking for an affordable primary residence or a sleek "lock-and-leave" weekend getaway, this condo delivers modern style in a prime, walkable location.Interior HighlightsNo detail was spared in this top-to-bottom

    Robin Apps Four Seasons Sotheby's Int'l Realty

    40 Bourn Brook Rd Unit 50, Manchester, VT 05255
  • /11

    $299,000

    • 4 Beds
    • 1 Bath
    • 2,156 Sq Ft

    558 Klondike Rd, Stamford, VT 05352

    This is a farmhouse that is currently under construction. Selling as is, with the remaining materials included. It is off grid and was lived in up until last year. Construction started in November 2025. Large barn that used to be a dairy farm. House has 3 woodstoves for heat. 10 cords of wood are included. Very nice setting along side a beautiful brook. 16.5 acres of open and wooded land that is

    Michael Jarvis United Country Real Estate Mike Jarvis Group Inc

    558 Klondike Rd, Stamford, VT 05352
  • /29

    $210,000

    • 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
  • /50

    $224,500

    • 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
  • /3

    $219,000

    • 2 Beds
    • 1 Bath
    • 1,872 Sq Ft

    17 Henry Hill, Stamford, VT 05352

    Sean Taylor Moresi Real Estate Partners

    17 Henry Hill, Stamford, VT 05352
  • /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 bedrooms.

    Cassie Barbeau Mahar McCarthy Real Estate

    254 Union St, Bennington, VT 05201
  • /2

    $249,000

    • Land
    • 29.9 Acres
    • $8,328 per Acre

    0 North Rd Unit 5079306, East Arlington, VT 05252

    Once you locate this quiet parcel there is a lovely wooded setting which offers a potential for a family compound or a possible subdivision. See Directions.There utilities along the extensive road frontage of North Road and Bacon Hollow Road which is a dead end... No soils or engineering value completed and must be processed with new zoning and state permitting.

    Charles Mauro Josiah Allen Real Estate, Inc.

    0 North Rd Unit 5079306, East Arlington, VT 05252
  • /14

    $234,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    240 Church St, Shaftsbury, VT 05262

    Ready for its next owner! This charming home offers a great opportunity for anyone looking to put their personal touch on a property with tons of potential. Sitting on an acre-sized lot, there’s plenty of room to expand. Inside, the home needs some TLC—but that’s where the value lies. With the right updates, you can truly bring your vision to life. The layout also provides potential for an in-law

    Derek Greene Derek Greene

    240 Church St, Shaftsbury, VT 05262
  • /32

    $275,000

    • 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
  • /21

    $249,000

    • Land
    • 3.42 Acres
    • $72,807 per Acre

    0 Havoc Hill Unit 29, Dorset, VT 05253

    Tranquility and Adventure Await on Havoc Hill. Discover 3.42 plus private, wooded acres nestled atop storied Havoc Hill in charming East Dorset, Vermont. Known for its beauty and historic ties to early Vermont logging and farming communities, Havoc Hill offers a rare opportunity to own land rich in character and natural serenity. Set off the picturesque Mad Tom Road, this secluded parcel is fully

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    0 Havoc Hill Unit 29, Dorset, VT 05253
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