92

Bennington County VT Homes for Sale with Garage

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  • /29

    $449,900

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    2121 North Rd, Arlington, VT 05250

    Beautifully maintained split-level home offering a wonderful combination of comfort, flexibility, and privacy! Situated on a large, one-acre private lot, the property features a circular driveway and loose-laid rock wall that frames the landscape with classic rural charm. The main level boasts an open-concept layout with gleaming hardwood floors throughout, a spacious living room, and a kitchen

    Matt Waddington Hoffman Real Estate

    2121 North Rd, Arlington, VT 05250
  • /6

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft

    2 Hamlin Ave, Bennington, VT 05201

    2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

    Lori Hurley Four Corner Properties LLC

    2 Hamlin Ave, Bennington, VT 05201
  • /20

    $649,000

    $46K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    27 Owls Head Hill Ln, Dorset, VT 05251

    Charming Raised Ranch on 2 Acres – Dorset, VTWelcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space.3 Bedrooms | 2 Full Baths | 2-Car Attached GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    27 Owls Head Hill Ln, Dorset, VT 05251
  • /30

    $649,900

    • 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 the

    Brian Hill Remax Summit

    23 Stonewall Ln, Dorset, VT 05251
  • /55

    $10,300,000

    New Construction
    • 6 Beds
    • 9 Baths
    • 10,993 Sq Ft

    551 West Fields, Manchester, VT 05254

    Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft

    Sunny Breen Josiah Allen Real Estate, Inc.

    551 West Fields, Manchester, VT 05254
  • /11

    $179,900

    • 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
  • /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
  • /45

    $365,000

    • 4 Beds
    • 1.5 Baths
    • 1,735 Sq Ft

    19 Royal St, North Bennington, VT 05257

    Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the

    Lindsey Martin Maple Leaf Realty

    19 Royal St, North Bennington, VT 05257
  • /45

    $299,900

    • 5 Beds
    • 2.5 Baths
    • 2,716 Sq Ft

    886 Hidden Valley Rd, Shaftsbury, VT 05262

    Escape to the rustic charm of this beautiful 5 bedroom, 2.5 bath log cabin nestled on 2 peaceful acres in the highly desirable town of Shaftsbury. From the moment you step inside, you’ll fall in love with the warm log features throughout, exposed beam ceilings, and the cozy fireplace that anchors the inviting living room. The charming country kitchen flows into a dedicated dining room, creating

    Julie Glover Mahar McCarthy Real Estate

    886 Hidden Valley Rd, Shaftsbury, VT 05262
  • /53

    $599,000

    $96K PRICE DROP
    • 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
  • /43

    $339,900

    • 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
  • /42

    $275,000

    $25K PRICE DROP
    • 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
  • /60

    $429,000

    • 3 Beds
    • 3 Baths
    • 2,119 Sq Ft

    131 Pine Cir, Bennington, VT 05201

    A must-see! Nestled in a quiet neighborhood just minutes from downtown dining and shopping, this beautifully maintained home offers comfort, flexibility, and thoughtful upgrades throughout. Completely renovated approximately 10 years ago, the home features a well-designed gourmet kitchen with granite countertops, a copper sink, soft-close cabinetry, and a custom built-in wine rack. French doors

    Thomas Martins Maple Leaf Realty

    131 Pine Cir, Bennington, VT 05201
  • /60

    $5,250,000

    • 9 Beds
    • 10 Baths
    • 7,900 Sq Ft

    1184 E Manchester Rd, Manchester, VT 05255

    Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    1184 E Manchester Rd, Manchester, VT 05255
  • /43

    $579,000

    • 3 Beds
    • 2 Baths
    • 2,501 Sq Ft

    856 Matteson Rd, North Bennington, VT 05257

    Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque—yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great

    Faith Rhodes Maple Leaf Realty

    856 Matteson Rd, North Bennington, VT 05257
  • /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
  • /42

    $345,000

    • 3 Beds
    • 1 Bath
    • 1,768 Sq Ft

    2154 U S 7, Pownal, VT 05261

    Charming antique Cape full of character and opportunity. This 3-bedroom, 1-bath home offers timeless New England charm with warm, inviting living spaces and a flexible layout ready for your personal touch. A first-floor bedroom and first-floor laundry provide the convenience of single-level living, while additional bedrooms upstairs offer flexibility for guests or office space. Original details

    Angela Bevin Maple Leaf Realty

    2154 U S 7, Pownal, VT 05261
  • /40

    $439,500

    $40K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,861 Sq Ft

    120 Village St, East Dorset, VT 05253

    Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

    Dana Kingsley Josiah Allen Real Estate, Inc.

    120 Village St, East Dorset, VT 05253
  • /37

    $584,900

    • 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 across

    Julie Citron RE/MAX Four Seasons

    14 Marisa Ln, Dorset, VT 05251
  • /26

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,688 Sq Ft

    67 Valley Pass, Manchester, VT 05255

    Welcome to 67 Valley Pass Road, where your new Vermont home awaits. This stylish split-level ranch has been meticulously maintained and is truly move in ready. The home features four bedrooms, highlighted by a spacious primary bedroom with an en suite bathroom.The upper level offers an updated open kitchen and dining area with an easy flowing layout. Just off the dining space is a cozy living

    Sara Buckley Josiah Allen Real Estate, Inc.

    67 Valley Pass, Manchester, VT 05255
  • /32

    $350,000

    • 2 Beds
    • 2 Baths
    • 1,196 Sq Ft

    10 Cass Terrace, Manchester Center, VT 05255

    Charming and beautifully updated, this 1920’s home blends timeless character with modern comfort in a desirable Manchester, Vermont setting. Offering 2 bedrooms and 2 baths within 1,200 square feet, this inviting home features an open kitchen flowing seamlessly into the dining area, highlighted by hardwood floors throughout and abundant natural light. A beautiful sunroom off the back of the home

    Kelley Mccarthy Mahar McCarthy Real Estate

    10 Cass Terrace, Manchester Center, VT 05255
  • /37

    $584,900

    • 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 across

    Julie Citron RE/MAX Four Seasons

    14A Marisa Ln, Dorset, VT 05251
  • /15

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,496 Sq Ft

    1803 Harwood Hill Rd, Bennington, VT 05201

    Set on a spacious lot and move-in ready raised ranch offers major updates, flexible living space, and excellent value. Recent improvements include a brand-new septic system, new roof, beautifully renovated kitchen, and new deck — giving buyers peace of mind and modern comfort from day one.The versatile lower level provides additional finished space ideal for a home office, family room, guest

    Lori Hurley Four Corner Properties LLC

    1803 Harwood Hill Rd, Bennington, VT 05201
  • /38

    $324,900

    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    2 Pine Rd, Bennington, VT 05201

    Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

    Brenda Jones KW Vermont - Brenda Jones Real Estate Group

    2 Pine Rd, Bennington, VT 05201
  • /40

    $5,900,000

    $1M PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    515 W Fields Rd, Manchester, VT 05254

    Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rareand exceptional 5-bedroom, 6-bathroom home....The creative design of Architect Ramsey Gourd and Master Builder Mark Breen, well knownas two of Southern Vermont's

    Sunny Breen Josiah Allen Real Estate, Inc.

    515 W Fields Rd, Manchester, VT 05254
  • /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
  • /46

    $1,550,000

    • 5 Beds
    • 5 Baths
    • 6,129 Sq Ft

    1035 Holy Smoke Rd, Shaftsbury, VT 05262

    Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

    Lori Hurley Four Corner Properties LLC

    1035 Holy Smoke Rd, Shaftsbury, VT 05262
  • /17

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 1,368 Sq Ft

    21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255

    THE PROGRAM: Purchase Price Assistance/ Mortgage Payment Reduction:Eligibility Requirements: * Vermont Residency or Residency at time of Purchase * First Time Vermont Homebuyer * Household Income at or Below $178,735* * Qualify for a Bank Mortgage * 10% Down Payment The developer will offer Gifted Equity and Paid Points at closing that will reduce the purchase price of the real estate and

    Britt Wohler

    21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255
  • /34

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,343 Sq Ft

    760 W Mountain Rd, Shaftsbury, VT 05262

    Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

    Kelley Mccarthy Mahar McCarthy Real Estate

    760 W Mountain Rd, Shaftsbury, VT 05262
  • /25

    $975,000

    $275K PRICE DROP
    • 8,888 Sq Ft

    124 Elm St, Bennington, VT 05201

    An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

    Marek Kovac TPW Real Estate

    124 Elm St, Bennington, VT 05201
  • /45

    $490,642

    $8K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,708 Sq Ft

    145 Oberdorf Rd, Readsboro, VT 05350

    Welcome to Alpenwald Village, a peaceful mountain community in scenic Readsboro, Vermont. This charming 4-bedroom chalet sits on 2 private acres and offers the perfect blend of comfort, style, and access to Vermont’s four-season lifestyle. Whether you're searching for a full-time residence or the ideal vacation getaway, this beautifully updated home delivers. Step inside to discover thoughtful

    Evan Russell Real Broker LLC

    145 Oberdorf Rd, Readsboro, VT 05350
  • /28

    $375,000

    • 2 Beds
    • 1 Bath
    • 1,256 Sq Ft

    3510 Rupert Rd, West Rupert, VT 05776

    Beautifully maintained and truly one-of-a-kind, this "Very Vermonty!" 2-bedroom residence offers the perfect blend of charm, comfort, and functionality. Set above a spacious garage, the home is in mint, immaculate condition and designed for easy living. Inside, you’ll find a warm and inviting interior complemented by mini-split systems for efficient heating and cooling. Every detail reflects

    Faith Rhodes Maple Leaf Realty

    3510 Rupert Rd, West Rupert, VT 05776
  • /48

    $3,285,000

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

    68 Green Peak Orchard S, East Dorset, VT 05253

    Located in the desirable Green Peak Orchard, this exceptional custom Greek Revival residence is set on 9.9 private acres surrounded by mature landscaping, stone walls, and terraces. Thoughtfully designed with timeless craftsmanship, the home features wide-plank floors, hand-plastered walls and ceilings, custom moldings, historic reproduction lighting, and finely crafted wainscoting and cabinetry.

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

    68 Green Peak Orchard S, East Dorset, VT 05253
  • /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
  • /60

    $1,495,000

    $300K PRICE DROP
    • 17 Beds
    • 20 Baths
    • 14,861 Sq Ft

    3888 Vermont Route 7a, Shaftsbury, VT 05262

    The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

    Vicki Wilson Maple Leaf Realty

    3888 Vermont Route 7a, Shaftsbury, VT 05262
  • /27

    $609,000

    • 4 Beds
    • 3 Baths
    • 1,650 Sq Ft

    60 Hilltop Rd Unit 60, Winhall, VT 05340

    Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    60 Hilltop Rd Unit 60, Winhall, VT 05340
  • /19

    $499,000

    • 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
  • /57

    $2,275,000

    $25K PRICE DROP
    • 9 Beds
    • 8 Baths
    • 5,512 Sq Ft

    288 Cedar Ln, Peru, VT 05152

    Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

    Jessica Citera Cummings & Co

    288 Cedar Ln, Peru, VT 05152
  • /56

    $2,875,000

    $475K PRICE DROP
    • 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 suites,

    David Shehadi Josiah Allen Real Estate, Inc.

    466 3 Maple Dr, Manchester, VT 05254

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