21,045

Bennington County, VT Homes

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  • /26

    $295,000 Pending

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

    235 Elm St Unit 3, Bennington, VT 05201

    This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

    Agent Photo

    Erica Hale

    Ridgeline Real Estate

    (802) 210-4437

    235 Elm St Unit 3, Bennington, VT 05201
  • /56

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft
    • House for Rent

    397 Powderhorn Rd, Manchester Center, VT 05255

    SPRING/SUMMER RENTAL: Charming newly renovated ranch with 3 bedrooms, 2 baths is the perfect summer rental, offering a cozy and inviting atmosphere! Conveniently located close to town for easy access to shops and dining. Enjoy a fenced-in backyard with a deck, perfect for grilling and outdoor relaxation. The kitchen and living room are located on the first floor, along with the spacious primary

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 729-7527

    397 Powderhorn Rd, Manchester Center, VT 05255
  • /29

    $535,000 Sold Nov 24, 2025

    • 1,850 Sq Ft
    • $289/SF
    • 72 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2002

    93 Mountain Ridge Rd, Peru, VT 05152

    Looking for a cozy Cape-style home near skiing, top-rated schools, and year-round outdoor activities? This charming yet modern residence, just minutes from Bromley, Magic, and Stratton Mountains and close to Londonderry and Manchester, offers the perfect blend of solid construction and timeless character. Built from the ground up in 2002, it features wide pine floors with radiant heat throughout,

    Andy Reed Four Seasons Sotheby's Int'l Realty

    93 Mountain Ridge Rd, Peru, VT 05152
    • /28

      Not Listed For Sale

      • 6 Beds
      • 6.5 Baths
      • 5,896 Sq Ft

      27 Mountain View Rd, Winhall, VT 05360

      27 Mountain View Rd, Winhall, VT 05360
  • /17

    $270,000 Pending

    • 6 Beds
    • 3 Baths
    • 2,900 Sq Ft

    239 - 241 Elm St, Bennington, VT 05201

    Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing

    Agent Photo

    Erica Hale

    Ridgeline Real Estate

    (802) 278-6021

    239 - 241 Elm St, Bennington, VT 05201
  • /9

    $1,350 per month

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    87 Cone Rd, Manchester Center, VT 05255

    Roomy 1 bedroom apartments located on a quiet dead end road near the center of town. Open living, dining and kitchen area, washer and dryer, air conditioning, patio. No pets, no smoking. $1,350.00/month plus utilities. One year lease, first, last and security due on signing.

    87 Cone Rd, Manchester Center, VT 05255
  • /38

    $635,000 Sold Nov 21, 2025

    • 2,499 Sq Ft
    • $254/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2006

    825 Case Ln, Readsboro, VT 05350

    We are currently accepting backup offers. This custom chalet on 52.7 private acres features a soaring cathedral ceiling with floor-to-ceiling windows framing a breathtaking view of the mountains, which rise behind the reservoir as a stunning natural backdrop. Monadnock Mountain in New Hampshire can be seen in the distance, adding to the picturesque setting that can be enjoyed from anywhere in the

    Melissa Nebelski Skihome Realty

    825 Case Ln, Readsboro, VT 05350
    • /24

      Est $320,000 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,200 Sq Ft

      1116 Old Rd W, Arlington, VT 05250

      1116 Old Rd W, Arlington, VT 05250
  • /33

    $239,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,120 Sq Ft

    2460 East Rd, Shaftsbury, VT 05262

    Well-maintained 3-bedroom, 2-bath ranch-style home on a 1-acre lot at the outskirts of town. Offering 1,120 square feet of single-level living space, this property features an efficient floor plan with an eat-in kitchen, comfortable living room, and three bedrooms including a primary with half bath. The home is clean and functional, with an opportunity for cosmetic updates to suit your style.

    Agent Photo

    Vicki Wilson

    Maple Leaf Realty

    (802) 474-4448

    2460 East Rd, Shaftsbury, VT 05262
  • /17

    $2,000 per month

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft
    • House for Rent

    13 Winhall Hollow Rd, Winhall, VT 05340

    Amazing Location!! This recently renovated home (2023) offers modern comfort in a quiet, wooded setting just minutes to Stratton Mountain. With 2.5 bedrooms, a full kitchen, and living spaces on both floors, it's an ideal year-roundresidence or seasonal ski retreat.The main bedrooms are spacious and bright, while the additional "half" bedroom features built-in bunks andlaundry perfect

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    13 Winhall Hollow Rd, Winhall, VT 05340
  • /48

    $296,500 Sold Nov 21, 2025

    • 1,896 Sq Ft
    • $156/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1993

    4 Rockwood St, Bennington, VT 05201

    Found your new home! This well maintained and updated ranch on a lovely corner lot has all of the ease of one-level living with all of the space you need. Relax on the covered side porch next to the stamped concrete patio with privacy fence for outdoor entertaining. Enjoy the sights and sounds of the peaceful brook on the wooded edge of the property. Two driveways provide ample parking for you

    Justine Curry Maple Leaf Realty

    4 Rockwood St, Bennington, VT 05201
    • /40

      Est $248,576 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 960 Sq Ft

      112 County Rd, Stamford, VT 05352

      112 County Rd, Stamford, VT 05352
  • /36

    $275,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,169 Sq Ft

    61 Autumn Acres, Bennington, VT 05201

    Welcome home to this charming single level ranch in a peaceful, friendly neighborhood where neighbors still wave hello and lend a cup of sugar. This home offers easy single-level living with three bedrooms, one full bath, and first floor laundry.Step inside to discover beautiful hardwood floors throughout most of the home, currently covered with carpeting that can easily be removed no nails

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 802-8871

    61 Autumn Acres, Bennington, VT 05201
  • /9

    $1,350 per month

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    87 Cone Rd, Manchester Center, VT 05255

    Roomy 1 bedroom apartments located on a quiet dead end road near the center of town. Open living, dining and kitchen area, washer and dryer, air conditioning, patio. No pets, no smoking. $1,350.00/month plus utilities. One year lease, first, last and security due on signing.

    87 Cone Rd, Manchester Center, VT 05255
  • /29

    $367,000 Sold Nov 21, 2025

    • 1,937 Sq Ft
    • $189/SF
    • 54 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1945

    26 College Rd, North Bennington, VT 05257

    Here's the house you have been waiting for! An attractive 3-bedroom, 2-bath, brick-veneer cape, situated on a pretty corner lot, just a skip away from downtown North Bennington, with all its amenities, and next door to Bennington College. There's room for the family, with a flexible layout that offers lots of possibilities, including first-floor living, with a full bathroom on the first floor.

    Phil Lewis Mahar McCarthy Real Estate

    26 College Rd, North Bennington, VT 05257
    • /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft

      6 Black Birch Rd, Winhall, VT 05340

      6 Black Birch Rd, Winhall, VT 05340
  • /15

    $915,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,898 Sq Ft

    3343 Main St, Manchester, VT 05255

    Steps from the heart of Manchester Village private 5 pastoral acres offer an unique opportunity while enjoying exceptional privacy and sweeping views of Equinox Mountain to the west. The Village, with marble walkways, underground power and electrified gas lanterns, undeniably creates a peaceful approach from a lengthy driveway back to this special residence buffered from the busy world, yet

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 808-6127

    3343 Main St, Manchester, VT 05255
  • /49

    $10,000 per month

    • 4 Beds
    • 3 Baths
    • 5,624 Sq Ft
    • House for Rent

    37 Burnt Hill Rd, Winhall, VT 05340

    MARCH 2026 ONLY. Location, Stratton ski shuttle, style, and so much space: Welcome to your mountain home! This luxurious Strattonwald home offers bedrooms for the whole crew, plus loads of living space, light, a well-equipped, gourmet kitchen for cooking and entertaining, and a hot tub for après-ski memories. It is well-built, lovingly cared-for, and a rare opportunity to rent for just one month

    Jamie Luke TPW Real Estate

    37 Burnt Hill Rd, Winhall, VT 05340
  • /48

    $351,000 Sold Nov 21, 2025

    • 2,994 Sq Ft
    • $117/SF
    • 7 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1958

    165 Pippin Knoll, Bennington, VT 05201

    Set well back from the road, this mid-century modern home emphasizes simple lines, an indoor-outdoor connection, and panoramic views. The main level centers on an open living/dining/kitchen area anchored by a fireplace and oversized windows that overlook the pond and rolling landscape beyond. The primary suite on this level provides private comfort. A second-floor bedroom offers a rare

    Kelley Mccarthy Mahar McCarthy Real Estate

    165 Pippin Knoll, Bennington, VT 05201
    • /40

      Est $498,491 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,010 Sq Ft

      68 Willows Way Unit 4, Peru, VT 05152

      68 Willows Way Unit 4, Peru, VT 05152
  • /60

    $985,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 3,215 Sq Ft

    92 Coventry Ln, Manchester Center, VT 05255

    Coventry House - Offered For The First Time! Built in 1972, the home was thoughtfully designed by local architect Charles "Bud" Lynch in collaboration with the owners. This custom-built home blends timeless design with natural surroundings. Offering a country kitchen, 4 bedrooms and 3+ vintage baths reflecting the 70’s era focus on color, natural materials, and open floor plans all on one level

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    (802) 424-8410

    92 Coventry Ln, Manchester Center, VT 05255
  • /2

    Call for Price

    Apartment for Rent

    1 Bed

    87 Cone Rd, Manchester Center, VT 05255

    87 Cone Rd, Manchester Center, VT 05255
  • /37

    $1,250,000 Sold Nov 21, 2025

    • 4,686 Sq Ft
    • $267/SF
    • 45 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2013

    7 Timberbrook N, Dorset, VT 05251

    Contemporary Luxury Farmhouse with two separate lots totaling 4.7 acres that combines amazing mountain views with the Modern Efficiency and Cost Savings of Geothermal Cooling & Heating and a Private Ground Mounted Tracking Solar Array! Natural light floods the entire home that includes a private primary suite, additional 4 bedrooms and 4 bathrooms. A large entry and foyer leads to the

    Gregory Cutler Four Seasons Sotheby's Int'l Realty

    7 Timberbrook N, Dorset, VT 05251
    • /4

      Not Listed For Sale

      AC Main St, Manchester, VT 05255

      AC Main St, Manchester, VT 05255
  • /28

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    72 Sawmill Rd, Pownal, VT 05261

    Experience the perfect blend of comfort and functionality in this modern doublewide, built in 2022, offering easy one-level living with upgraded insulation for energy efficiency. Features newer sitework with a drilled well and engineered septic system designed and permitted for 2 bedrooms, meaning 4-person occupancy. This spacious home features three bedrooms, allowing for versatile options using

    Agent Photo

    Gary Fuls Jr

    RE/MAX Transitions

    (802) 722-7730

    72 Sawmill Rd, Pownal, VT 05261
  • /19

    $4,000 per month

    • 4 Beds
    • 1.5 Baths
    • 1,404 Sq Ft
    • House for Rent

    937 Route 30, Dorset, VT 05251

    Welcome home! This beautiful and well maintained 4 bedroom, 1.5-bath home is in the charming town of Dorset. It offers over 1,404 sq feet of single-story living. This very well thought out and comfortable floor plan features a bright, large living and dining room and many windows throughout the entire house. A separate dining area perfect for gatherings. Enjoy the outdoors on the large back deck

    Martina Dvorak-Grattan Wohler Realty Group

    937 Route 30, Dorset, VT 05251
  • /37

    $950,000 Sold Nov 20, 2025

    • 3,697 Sq Ft
    • $257/SF
    • 91 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1850

    1589 Richville Rd, Manchester Center, VT 05255

    Welcome to your dream Vermont retreat. This classic 3 bedroom Colonial is gracefully set on 9.52 acres of open meadows with direct frontage on the Battenkill River, renowned worldwide for its exceptional trout fishing. With timeless architecture, peaceful privacy, and sweeping Mountain views, this property captures the essence of New England living. Inside, the home blends historic charm with

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

    1589 Richville Rd, Manchester Center, VT 05255
    • /35

      Est $609,475 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,577 Sq Ft

      10 Pond View Rd, Winhall, VT 05340

      10 Pond View Rd, Winhall, VT 05340
  • /58

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 3,284 Sq Ft

    1098 W Sandgate Rd, Arlington, VT 05250

    Private, Quiet, and Solidly built timeless Post & Beam 2,200 SF residence on 10.05 acres offering South and Westerly sunlight all day long ending with lovely sunsets! Overlooking a spring fed pond and a mix of open terrain and deciduous slope side forest with trails. The house offers main level all open 40' X 32' great room living / dining/ kitchen with a massive center 2.5 story stone fireplace.

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 992-1723

    1098 W Sandgate Rd, Arlington, VT 05250
  • /2

    $1,100 per month

    • 1 Bed
    • 1 Bath
    • House for Rent

    165 Benmont Ave, Bennington, VT 05201

    Property Id: 1488761I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

    165 Benmont Ave, Bennington, VT 05201
  • /54

    $660,000 Sold Nov 19, 2025

    • 2,208 Sq Ft
    • $299/SF
    • 40 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    1148 Kent Hollow Rd, West Rupert, VT 05776

    Country charm at the foot of Shatterack Mountain. Nestled in a classic Currier & Ives setting, this exceptional Cape Cod style home and barn sit on over 37 private acres, accessed by a a picturesque bridge over White Creek. Built by craftsman Mark Breen and inspired by a 300 year old Connecticut Cape, this home showcases timeless period detailing with crown molding and picture windows.

    Margretta Fischer Wohler Realty Group

    1148 Kent Hollow Rd, West Rupert, VT 05776
    • /40

      Est $334,000 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,890 Sq Ft

      214 Pleasant St, Arlington, VT 05250

      214 Pleasant St, Arlington, VT 05250
  • /25

    $350,000

    • Land
    • 26.5 Acres
    • $13,208 per Acre

    942 Rt 315 Route, Rupert, VT 05768

    26.5 acres offering all the sought after components and is conveniently located nearby the greater Dorset/Manchester amenities! The 26.5 acres is enrolled in the Current Use (Land Use) program however, is about to be removed. The acreage backs onto the 3000 acre Merck Forrest Foundation which offers tremendous hiking, snowshoe trekking, camping, farmstead activity, sugaring, and nature tracking.

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 347-9113

    942 Rt 315 Route, Rupert, VT 05768
  • /19

    $35,000 per month

    • 3 Beds
    • 3 Baths
    • 2,920 Sq Ft
    • House for Rent

    2 Aspen Ln, Winhall, VT 05340

    Stratton views, sunlight, space, and location: this ski chalet has it all! The open floor plan of the main level brings everyone together around the spacious kitchen, dining area, and living room, under a vaulted cathedral ceiling and with a wall of windows overlooking the forest below and Stratton's peak ahead. Front deck offers dining area and a grill for the most outdoorsy of chefs! Two

    Jamie Luke TPW Real Estate

    2 Aspen Ln, Winhall, VT 05340
  • /33

    $820,000 Sold Nov 18, 2025

    • 3,037 Sq Ft
    • $270/SF
    • 89 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1980

    725 Wideawake Rd, Manchester Center, VT 05255

    This home offers approximately 3,000 square feet of living space, including three bedrooms plus an additional room for guests, and three bathrooms. The first floor features a spacious master en suite with a walk-in closet, French doors leading to a patio, and a beautifully updated bathroom with radiant flooring and a marble shower. Also on the first floor, you'll find a bright and airy kitchen

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    725 Wideawake Rd, Manchester Center, VT 05255
    • /27

      Est $183,154 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,155 Sq Ft

      731 Main St, Bennington, VT 05201

      731 Main St, Bennington, VT 05201
  • /33

    $850,000

    • 4 Beds
    • 3.5 Baths
    • 3,658 Sq Ft

    146 Ridges Way Unit 1200-1, Peru, VT 05152

    The Top of the World! Follow the road to the very top of Bromley Village where this secluded condo enjoys sweeping views of the surrounding Green Mountains. This three level, well appointed unit has four nice sized bedrooms, three and a half baths and is a short walk to the Plaza trail for mountain access. Long time owners added special features to this Ridges Townhouse, including hand wrought

    Agent Photo

    Christopher Cummings

    Cummings & Co

    (802) 481-3899

    146 Ridges Way Unit 1200-1, Peru, VT 05152
  • /15

    $1,225 per month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    938 Vt-7a Unit 4, Shaftsbury, VT 05262

    Lovely 2 bedroom apartment available in Shaftsbury Vermont. Rent includes water and sewer, snow plowing, and lawn maintenance. One year lease required with first and last month's rent and security deposit.

    938 Vt-7a Unit 4, Shaftsbury, VT 05262
  • /3

    $110,000 Sold Nov 17, 2025

    • Land
    • 11.5 Acres
    • $9,565 per Acre
    • 0 Days On Market

    0 Maple Hill Rd, Shaftsbury, VT 05262

    Listed off MLS and sold direct to sellers contact.

    Lilli West Maple Leaf Realty

    0 Maple Hill Rd, Shaftsbury, VT 05262
    • /40

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,648 Sq Ft

      740 Vt Route 9, Woodford, VT 05201

      740 Vt Route 9, Woodford, VT 05201

Showing Results 41 - 80, Page 2 of 18

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