20,622

Bennington County, VT Homes

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  • /33

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,911 Sq Ft

    21 Russett Dr, Bennington, VT 05201

    Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character.Inside, the versatility of this home truly shines. The main level offers a comfortable living

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    21 Russett Dr, Bennington, VT 05201
  • /10

    $2,700 Per Month

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • House for Rent

    127 Mountain Ridge Rd, Peru, VT 05152

    If you're looking for a year-round rental in the Peru/Londonderry area, this contemporary mountain home has so much to offer. The inviting open-concept layout features a kitchen, living and dining space that extends out to a charming sun porch and back deck. Nestled close to Flood Brook, Bromley, and all that Londonderry and Peru have to offer, the location is convenient. And across the street

    Jamie Luke TPW Real Estate

    127 Mountain Ridge Rd, Peru, VT 05152
  • /31

    $895,000

    Sold Dec 12, 2025

    73 Cranberry Hill Rd, Winhall, VT 05340

    • 4 Beds
    • 4.5 Baths
    • 2,658 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $337/SF
    • 222 Days On Market

    Current Estimated Value $927,697

    Last Listing Agent Carrie Mathews Winhall Real Estate

    73 Cranberry Hill Rd, Winhall, VT 05340
    • /8

      Not Listed For Sale

      79 Heartwellville View Rd, Readsboro, VT 05350

      79 Heartwellville View Rd, Readsboro, VT 05350

      Last Sold Summary

      • 167 Days On Market

      Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

  • /56

    $1,200,000

    $1M PRICE DROP
    • 6 Beds
    • 3 Baths
    • 3,340 Sq Ft

    215 & 221 Vt Route 30, Dorset, VT 05251

    Two homes, multiple barns and outbuildings on 60 +/- incredible acres in Dorset, VT. Nestled in the Green Mountains, 215 Route 30 the 1780s farmhouse featuring 3 bedrooms, 2 baths with 1645 finished sqft. The second building, nestled away from the road is 221 Route 30 built in 1940 with 3 bedrooms and 2 baths. 1800 sqft. The property offers pastoral venues, mature forest, and scenic mountain

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    215 & 221 Vt Route 30, Dorset, VT 05251
  • /57

    $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: Available: April 15th, 2027 - October 30th, 2027. 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

    Laura Beckwith Josiah Allen Real Estate, Inc.

    397 Powderhorn Rd, Manchester Center, VT 05255
  • /60

    $530,000

    Sold Aug 15, 2025

    2354 Danby Mountain Rd, Dorset, VT 05251

    • 3 Beds
    • 2 Baths
    • 2,031 Sq Ft
    • Built 1968

    Last Sold Summary

    • 17% Below List Price
    • $261/SF
    • 244 Days On Market

    Last Listing Agent Margretta Fischer Wohler Realty Group

    2354 Danby Mountain Rd, Dorset, VT 05251
    • /39

      Est $382,887

      Not Listed For Sale

      744 Dunlap Farm Rd, Arlington, VT 05250

      • 3 Beds
      • 2 Baths
      • 1,306 Sq Ft
      • Built 1985
      744 Dunlap Farm Rd, Arlington, VT 05250

      Last Sold Summary

      • 89 Days On Market

      Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  • /29

    $255,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,458 Sq Ft

    2650 Rupert Rd, Arlington, VT 05250

    Mountain View Oasis – 17 Acres of Open & Wooded SerenityEscape to your own private retreat with this two-bedroom, one-bath home nestled on 17 acres of beautiful open and wooded forest land. Built in 1999, this solidly constructed home features a poured concrete foundation, underground power, conventional septic system, and durable metal roof — giving you peace of mind with all the major

    Agent Photo

    Margretta Fischer

    Wohler Realty Group

    2650 Rupert Rd, Arlington, VT 05250
  • /23

    $32,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • House for Rent

    65 Cranberry Hill Rd, Bondville, VT 05340

    Never before offered: This Strattonwald contemporary ski house is a well cared-for home base for all who love the mountain lifestyle, in a private woodland setting just 9 minutes to Stratton's Main Base. The expansive living room is the ultimate gathering spot from morning to night, with soaring cathedral ceilings, a super-cozy wood stove, and extraordinary windows looking out at the private

    Jamie Luke TPW Real Estate

    65 Cranberry Hill Rd, Bondville, VT 05340
  • /44

    $1,075,000

    Sold Jul 17, 2026

    5173 Route 30, Dorset, VT 05251

    • 4 Beds
    • 4.5 Baths
    • 3,584 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Above List Price
    • $300/SF
    • 2 Days On Market

    Current Estimated Value $1,042,630

    Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

    5173 Route 30, Dorset, VT 05251
    • /27

      Est $197,550

      Not Listed For Sale

      731 Main St, Bennington, VT 05201

      • 2 Beds
      • 1.5 Baths
      • 1,155 Sq Ft
      • Built 1900
      731 Main St, Bennington, VT 05201

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Dana Haley Real Broker LLC

  • /60

    $1,650,000

    • 3 Beds
    • 4 Baths
    • 5,072 Sq Ft

    36 Beaver St, Bondville, VT 05340

    Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage,

    MaryKate Grey Stratton Real Estate

    36 Beaver St, Bondville, VT 05340
  • /56

    $6,250 Per Month

    • 5 Beds
    • 3.5 Baths
    • 4,352 Sq Ft
    • Townhouse for Rent

    764 Barnumville Rd Unit 4, Manchester Center, VT 05255

    Located on the ski side of Manchester Center, this unique 4,352 SF, 5 bedroom, 4 bath, town home is part of a 5 unit complex that was converted from a working Dairy Barn in 1976. Original post and beam throughout, this unit is turn-key and ready to rent for a 1 year lease. The home has very generous size rooms, lots of living space, large eat in kitchen and a finished lower level. The second

    Laura Beckwith Josiah Allen Real Estate, Inc.

    764 Barnumville Rd Unit 4, Manchester Center, VT 05255
  • /36

    $220,000

    Sold Aug 20, 2025

    1211 Carpenter Hill Rd, Bennington, VT 05201

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1930

    Last Sold Summary

    • 10% Above List Price
    • $157/SF
    • 4 Days On Market

    Last Listing Agent Peter West BISHOP WEST REAL ESTATE

    1211 Carpenter Hill Rd, Bennington, VT 05201
    • /40

      Not Listed For Sale

      740 Vt Route 9, Woodford, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,648 Sq Ft
      • Built 1993
      740 Vt Route 9, Woodford, VT 05201

      Last Sold Summary

      • 139 Days On Market

      Last Listing Agent Justine Curry Maple Leaf Real Estate

  • /21

    $314,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,337 Sq Ft

    78 Carbonti Cir, Arlington, VT 05250

    Enjoy effortless one-level living in this wonderful Arlington home, offering 3 bedrooms, 2 bathrooms, and a bright, modern layout. Set in a lovely neighborhood, the home welcomes you with a west-facing living room window that frames beautiful mountain views.Two bedrooms are tucked into the northeast corner of the home, while the spacious primary suite with its own full bathroom sits

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    78 Carbonti Cir, Arlington, VT 05250
  • /23

    $34,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,406 Sq Ft
    • House for Rent

    35 Strattonwald Rd, Winhall, VT 05340

    $28,000 Winter Rental Rate | Spend the winter in Vermont at this inviting 4-bedroom, 3-bath Strattonwald chalet, available mid-November through mid-April. Nestled among the woods yet just minutes from Stratton Mountain, this home offers a welcoming retreat and the perfect base for the ski season. The main living area features soaring vaulted ceilings and a pellet stove, creating a bright and cozy

    Cheyanne Pugliese

    35 Strattonwald Rd, Winhall, VT 05340
  • /31

    $77,000

    Sold Aug 04, 2026

    109 Evergreen Dr, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft
    • Built 1940

    Last Sold Summary

    • 38% Below List Price
    • $51/SF
    • 164 Days On Market

    Current Estimated Value $99,517

    Last Listing Agent Zachary Zupan EXP Realty

    109 Evergreen Dr, Bennington, VT 05201
    • /36

      Est $445,720

      Not Listed For Sale

      21 Birches Way, Peru, VT 05152

      • 3 Beds
      • 2 Baths
      • 1,275 Sq Ft
      • Built 1975
      21 Birches Way, Peru, VT 05152

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty

  • /16

    $1,050,000

    • 4 Beds
    • 3.5 Baths
    • 2,256 Sq Ft

    16 Middle Ridge Rd Unit 22, Winhall, VT 05155

    Unique four bedroom three and one half bath townhome, located directly across the street from the Stratton Village and ski area. Built in 1988, Fox Chapel is the second phase of the Village Chalet neighborhood. Only 27 of these properties exist. Although connected by a breezeway to the property next to it, feels very much like a stand alone home. Walking distance to shops, restaurants and all ski

    John Sikes Stratton Real Estate

    16 Middle Ridge Rd Unit 22, Winhall, VT 05155
  • /35

    $7,250 Per Month

    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • House for Rent

    45 Benson Fuller Dr, Bondville, VT 05340

    THE ULTIMATE STRATTON MOUNTAIN RETREAT Experience the perfect Vermont winter getaway in this exceptional home ideally located directly off the prestigious Stratton Mountain access road. Boasting a premier location with effortless mountain access, this property is designed for those who want to maximize their time on the slopes and enjoy a seamless mountain lifestyle. Available for multiple

    David Powers 42 North LP

    45 Benson Fuller Dr, Bondville, VT 05340
  • /17

    $159,900

    Sold Jun 05, 2026

    432 South St Unit B2, Bennington, VT 05201

    • 2 Beds
    • 1.5 Baths
    • 852 Sq Ft
    • Built 1989

    Last Sold Summary

    • $188/SF
    • 40 Days On Market

    Current Estimated Value $162,187

    Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

    432 South St Unit B2, Bennington, VT 05201
    • /11

      Not Listed For Sale

      117 Elm St, Manchester Center, VT 05255

      • 12 Beds
      • 6 Baths
      • 3,682 Sq Ft
      • Built 1850
      117 Elm St, Manchester Center, VT 05255

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent David Citron RE/MAX Four Seasons

  • /32

    $1,150,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 1,775 Sq Ft

    43 Middle Ridge Rd Unit RBL 417, Winhall, VT 05155

    Welcome to this beautifully maintained top-floor Rising Bear condominium, where you’ll enjoy stunning views of Stratton Mountain and the Commons Pond from nearly every room. The soaring cathedral ceilings and abundant natural light create a bright, open feel, while the spacious loft overlooking the living area offers a great spot for relaxing, gathering, or extra sleeping space. The living room

    Jamie Wylie Stratton Real Estate

    43 Middle Ridge Rd Unit RBL 417, Winhall, VT 05155
  • /41

    $25,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,844 Sq Ft
    • House for Rent

    78 Stoney Fields Rd, Manchester Center, VT 05255

    Enjoy the perfect Vermont winter getaway in this spacious 4 bedroom, 3 bath, 2,844 SF ranch home set on 2.13 private acres, just steps from downtown Manchester Center. Recently refreshed with stylish wallpaper, modern wood floors, and brand new kitchen appliances, this home blends cozy charm with contemporary comfort. Relax on the new expansive deck offering sweeping mountain views, or unwind in

    Laura Beckwith Josiah Allen Real Estate, Inc.

    78 Stoney Fields Rd, Manchester Center, VT 05255
  • /36

    $435,000

    Sold Mar 24, 2026

    1061 Granger Hollow Rd, North Bennington, VT 05257

    • 3 Beds
    • 2 Baths
    • 2,108 Sq Ft
    • Built 1990

    Last Sold Summary

    • 13% Below List Price
    • $206/SF
    • 215 Days On Market

    Current Estimated Value $448,825

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    1061 Granger Hollow Rd, North Bennington, VT 05257
    • /23

      Not Listed For Sale

      53 Elm St, Manchester Center, VT 05255

      • 10 Beds
      • 7 Baths
      • 5,103 Sq Ft
      • Built 1850
      53 Elm St, Manchester Center, VT 05255

      Last Sold Summary

      • 183 Days On Market

      Last Listing Agent David Citron RE/MAX Four Seasons

  • /10

    $20,000

    • Land
    • 1.2 Acres
    • $16,667 per Acre

    379 Oberdorf Rd, Readsboro, VT 05350

    1.2 Acres of Scenic Land for Sale in Bennington County, VTEscape to the beauty of Bennington County, Vermont, with this stunning 1.2-acre parcel of vacant land. Offering 350 ft of road frontage on Oberdorf Rd, this lot provides easy access and is nestled within the private Alpenwald Village, a peaceful community ideal for your dream home or vacation retreat. Surrounded by nature, this

    Community Lands Community Lands

    379 Oberdorf Rd, Readsboro, VT 05350
  • /25

    $2,000 Per Month

    • 1 Bed
    • 1 Bath
    • 767 Sq Ft
    • Townhouse for Rent

    56 Cemetery Rd, Arlington, VT 05250

    Newly built in 2019, this 1 bed, 1 bath, duplex is located in Arlington, just off the highway for easy commuting and convenient access to local amenities. Perfect for a single professional or a couple seeking a comfortable, low-maintenance apartment in a convenient location. Seeking 1 year lease! All utilities included in the price except for trash, cable and internet. Apartment is being rented

    Laura Beckwith Josiah Allen Real Estate, Inc.

    56 Cemetery Rd, Arlington, VT 05250
  • /60

    $899,000

    Sold Dec 12, 2025

    92 Coventry Ln, Manchester Center, VT 05255

    • 4 Beds
    • 2.5 Baths
    • 3,215 Sq Ft
    • Built 1972

    Last Sold Summary

    • 18% Below List Price
    • $280/SF
    • 101 Days On Market

    Current Estimated Value $860,541

    Last Listing Agent Kristin Comeau TPW Real Estate

    92 Coventry Ln, Manchester Center, VT 05255
    • /60

      Est $315,800

      Not Listed For Sale

      818 Main St, Bennington, VT 05201

      • 4 Beds
      • 3 Baths
      • 1,969 Sq Ft
      • Built 1920
      818 Main St, Bennington, VT 05201

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /27

    $209,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,075 Sq Ft

    1083 Main St, Bennington, VT 05201

    Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    1083 Main St, Bennington, VT 05201
  • /52

    $4,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,547 Sq Ft
    • Townhouse for Rent

    80 Murray Hill South Rd Unit 10, Manchester, VT 05255

    Winter Seasonal Rental – Downtown Manchester Center. Enjoy the best of Vermont this ski season in this beautiful 3 bedroom, 3 bath end unit offering breathtaking mountain views and an unbeatable location in the heart of downtown Manchester Center. With 1,567 square feet of comfortable living space, this bright and spacious condo features an open floor plan, abundant natural light, and a large

    Laura Beckwith Josiah Allen Real Estate, Inc.

    80 Murray Hill South Rd Unit 10, Manchester, VT 05255
  • /57

    $1,575,000

    Sold Oct 21, 2025

    671 West Rd, Manchester Center, VT 05255

    • 5 Beds
    • 3.5 Baths
    • 4,785 Sq Ft
    • Built 1790

    Last Sold Summary

    • $329/SF
    • 8 Days On Market

    Current Estimated Value $1,805,735

    Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

    671 West Rd, Manchester Center, VT 05255
    • /18

      Est $220,218

      Not Listed For Sale

      9 Palmer Dr, Pownal, VT 05261

      • 1 Bed
      • 1 Bath
      • 1,012 Sq Ft
      • Built 1850
      9 Palmer Dr, Pownal, VT 05261

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Melissa Nebelski Real Broker LLC

  • /11

    $155,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,643 Sq Ft

    905 County St, Bennington, VT 05201

    Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property with a lot of square footage.

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    905 County St, Bennington, VT 05201
  • /60

    $12,500 Per Month

    • 4 Beds
    • 4.5 Baths
    • 4,393 Sq Ft
    • House for Rent

    163 Taconic Rd, Manchester, VT 05255

    Exclusive Taconic Avenue walk to Village Location... Rarely found, Recently Constructed in 2002 this High Country Colonial is on one acre seamlessly blending within the historic district. Aesthetically pleasing among the area's recently restored Houses of the Hildene era, this residence meets all expectations! Deep front porch entry to soaring foyer flanked with formal rooms while the family

    Laura Beckwith Josiah Allen Real Estate, Inc.

    163 Taconic Rd, Manchester, VT 05255
  • /41

    $248,000

    Sold Mar 06, 2026

    1160 Bergrucken Ln, Readsboro, VT 05350

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft
    • Built 1978

    Last Sold Summary

    • 4% Below List Price
    • $304/SF
    • 11 Days On Market

    Current Estimated Value $246,108

    Last Listing Agent Morriah Adams BHG Masiello Brattleboro

    1160 Bergrucken Ln, Readsboro, VT 05350
    • /79

      Est $435,370

      Not Listed For Sale

      460 Sparrow Dr, Stamford, VT 05352

      • 4 Beds
      • 3 Baths
      • 3,721 Sq Ft
      • Built 1988
      460 Sparrow Dr, Stamford, VT 05352

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Colleen Zajac MONARCH REALTY, INC.

Showing Results 121 - 160, Page 4 of 18

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