21,114

Bennington County, VT Homes

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  • /20

    $524,900

    • 4 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    1180 North Rd, East Arlington, VT 05252

    Have your own slice of quintessential Vermont with this 3 acre property at the base of the Green Mountains. A lush, wooded, private property, you will love this 4 bed, 2.5 bath Sunderland home. The 1st floor is an open floor plan with plenty of natural light with a bonus recreational room/office and half bath. The kitchen has granite counters with an updated faucet and oven hood with a butcher

    Jason Saphire www.HomeZu.com

    1180 North Rd, East Arlington, VT 05252
  • /51

    $434,000 Sold Feb 27, 2026

    12 Stratton West Rd Unit 12, Winhall, VT 05340

    • 5 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1968

    Last Sold Summary

    • 1% Below List Price
    • $230/SF
    • 6 Days On Market

    Last Listing Agent Robert Sabol Wohler Realty Group

    12 Stratton West Rd Unit 12, Winhall, VT 05340
    • /29

      Est $478,424 Not Listed For Sale

      9378 Vt Route 9, Bennington, VT 05201

      • 4 Beds
      • 3 Baths
      • 1,752 Sq Ft
      • Built 1985
      9378 Vt Route 9, Bennington, VT 05201

      Last Sold Summary

      • 4% Above List Price
      • $261/SF
      • 6 Days On Market

      Last Sold Price $458,000

      Last Listing Agent Lisa Mirando Deerfield Valley Real Estate

  • /44

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    475 Sunrise Ln, Arlington, VT 05250

    Discover your private retreat on Beautiful Sunrise Lane! Welcome to "Pine Hollow". This comfortable and inviting home sits on over 6 acres of serene, peaceful landscape, for those seeking a quiet environment and space! Idyllic setting surrounded by pines with complete solitude at the end of a private rd. Enjoy the comfort of generous rooms filled with natural light, ideal for family living and

    Sunny Breen Josiah Allen Real Estate, Inc.

    475 Sunrise Ln, Arlington, VT 05250
  • /28

    $213,200 Sold May 30, 2025

    1004 Main St, Bennington, VT 05201

    • 5 Beds
    • 3 Baths
    • 1,872 Sq Ft
    • Built 1920

    Last Sold Summary

    • 2% Above List Price
    • $114/SF
    • 50 Days On Market

    Current Estimated Value $222,924

    Last Listing Agent Erica Hale Ridgeline Real Estate

    1004 Main St, Bennington, VT 05201
    • /16

      Est $235,491 Not Listed For Sale

      214 Hickory Rd, Bennington, VT 05201

      • 3 Beds
      • 1.5 Baths
      • 1,005 Sq Ft
      • Built 1960
      214 Hickory Rd, Bennington, VT 05201

      Last Sold Summary

      • 6% Below List Price
      • $249/SF
      • 14 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Lori Hurley Four Corner Properties LLC

  • /53

    $675,000

    • 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
  • /24

    $1,025,000 Sold Oct 10, 2025

    10 Middle Ridge Rd, Winhall, VT 05155

    • 4 Beds
    • 3.5 Baths
    • 2,160 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Above List Price
    • $475/SF
    • 5 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    10 Middle Ridge Rd, Winhall, VT 05155
    • /47

      Est $406,151 Not Listed For Sale

      201 Erbs Way, Bennington, VT 05201

      • 3 Beds
      • 3.5 Baths
      • 2,686 Sq Ft
      • Built 1974
      201 Erbs Way, Bennington, VT 05201

      Last Sold Summary

      • 4% Above List Price
      • $145/SF
      • 7 Days On Market

      Last Sold Price $389,000

      Last Listing Agent Vicki Wilson Maple Leaf Realty

  • /35

    $695,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 2,715 Sq Ft

    9 Old Route 30, Winhall, VT 05340

    Classic Vermont farmhouse set on over 18 private acres with Bromley Mountain views, offering timeless character, privacy, and mountain views. This four-bedroom, two-bath home features a striking stone fireplace anchoring the main living space, along with a dedicated library and office—ideal for reading, work, or creative pursuits. Outdoor living shines with a spacious patio and stone firepit,

    Carrie Mathews Winhall Real Estate

    9 Old Route 30, Winhall, VT 05340
  • /19

    $141,000 Sold Jun 03, 2025

    432 South St Unit C7, Bennington, VT 05201

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

    Last Sold Summary

    • 4% Below List Price
    • $172/SF
    • 46 Days On Market

    Current Estimated Value $148,142

    Last Listing Agent Abi Gregorio

    432 South St Unit C7, Bennington, VT 05201
    • /25

      Est $753,845 Not Listed For Sale

      110 Upper Taylor Hill Rd, Jamaica, VT 05343

      • 5 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1968
      110 Upper Taylor Hill Rd, Jamaica, VT 05343

      Last Sold Summary

      • 6% Above List Price
      • $445/SF
      • 15 Days On Market

      Last Sold Price $711,500

      Last Listing Agent Helen Nault

  • /60

    $995,000

    • 6 Beds
    • 7 Baths
    • 5,400 Sq Ft

    2001 Depot St, Manchester Center, VT 05255

    LOCATION, LOCATION: Just 8 minutes to Bromley and 20 minutes to Stratton, yet close to Manchester’s dining, shopping, fishing, golf, and the Horse Show. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bath retreat offers over 5,400 sq ft on 3.2 private acres—ideal as a primary home, vacation getaway, or rental investment. With a strong history as a

    Steven Bryant TPW Real Estate

    2001 Depot St, Manchester Center, VT 05255
  • /16

    $54,900 Sold Oct 24, 2025

    255 Vermont 8, Searsburg, VT 05363

    • Land
    • 0.83 Acre
    • $66,145 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Jacki Murano Southern Vermont Realty Group

    255 Vermont 8, Searsburg, VT 05363
    • /35

      Not Listed For Sale

      15 Stratton View Rd, Bondville, VT 05340

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1964
      15 Stratton View Rd, Bondville, VT 05340

      Last Sold Summary

      • 5% Below List Price
      • $250/SF
      • 1 Day On Market

      Last Sold Price $420,000

      Last Listing Agent Rachel Febbie EXP Realty

  • /13

    $649,900

    • 2 Beds
    • 2 Baths
    • 2,250 Sq Ft

    23 Stonewall Ln, Dorset, VT 05251

    Charming Colonial home set on 1.79 acres in the Vintage Village of Dorset. The home offers two bedrooms and one and three-quarters baths, a large living room, a fireplace, and centrally located kitchen. Easy access to downtown Manchester and surrounding ski areas and hiking trails.

    Diana Lynn Harvey Alison McCullough Real Estate

    23 Stonewall Ln, Dorset, VT 05251
  • /23

    $125,000 Sold Oct 07, 2025

    5089 Vt Route 7a, Arlington, VT 05250

    • 3 Beds
    • 3 Baths
    • 2,206 Sq Ft
    • Built 1976

    Last Sold Summary

    • 14% Above List Price
    • $57/SF
    • 6 Days On Market

    Current Estimated Value $204,000

    Last Listing Agent Susan Bellville Bellville Realty

    5089 Vt Route 7a, Arlington, VT 05250
    • /11

      Est $553,708 Not Listed For Sale

      1238 North Rd, East Arlington, VT 05252

      • 3 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 2003
      1238 North Rd, East Arlington, VT 05252

      Last Sold Summary

      • 20% Below List Price
      • $261/SF
      • 4 Days On Market

      Last Sold Price $690,000

      Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  • /27

    $675,000

    • 2 Beds
    • 2 Baths
    • 1,432 Sq Ft

    4928 Main St Unit 2, Manchester Center, VT 05255

    Fabulous two bedroom two bath condominium converted in 2017 in the heart of Manchester Center. Many fine features: Marvin windows, hardwood flooring, central air conditioning, forced hot air heat, private second floor sundeck, mountain views. This one level second floor unit is accessed by private elevator and offers pretty mountain views through the oversized 9 foot windows. The living room has

    David Halligan Four Seasons Sotheby's Int'l Realty

    4928 Main St Unit 2, Manchester Center, VT 05255
  • /40

    $595,000 Sold Nov 10, 2025

    4A Ridge, Winhall, VT 05340

    • 3 Beds
    • 3 Baths
    • 1,886 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $315/SF
    • 31 Days On Market

    Last Listing Agent Christiane Carroccio TPW Real Estate

    4A Ridge, Winhall, VT 05340
    • /19

      Est $407,740 Not Listed For Sale

      367 Shady Pines, Arlington, VT 05250

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1976
      367 Shady Pines, Arlington, VT 05250

      Last Sold Summary

      • 16% Above List Price
      • $208/SF
      • 4 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Josh Wien Northshire Realty

  • /50

    $750,000

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

    57 Pearl Buck Dr Unit 33, Bondville, VT 05340

    WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    57 Pearl Buck Dr Unit 33, Bondville, VT 05340
  • /19

    $225,000 Sold Aug 29, 2025

    1801 S Stream Rd, Bennington, VT 05201

    • Land
    • 16.68 Acres
    • $13,489 per Acre

    Last Sold Summary

    • 34 Days On Market

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    1801 S Stream Rd, Bennington, VT 05201
    • /14

      Est $442,657 Not Listed For Sale

      535 Dunlap Farm Rd, Arlington, VT 05250

      • 2 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1986
      535 Dunlap Farm Rd, Arlington, VT 05250

      Last Sold Summary

      • 17% Above List Price
      • $272/SF
      • 55 Days On Market

      Last Sold Price $379,000

      Last Listing Agent Sean Dillon Real Broker LLC

  • /40

    $695,000

    • 3 Beds
    • 2.5 Baths
    • 2,868 Sq Ft

    134 Monument Ave, Bennington, VT 05201

    Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary

    Kelley Mccarthy Mahar McCarthy Real Estate

    134 Monument Ave, Bennington, VT 05201
  • /21

    $175,000 Sold Dec 23, 2025

    2591 Chapel Rd, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 11 Days On Market

    Current Estimated Value $183,317

    Last Listing Agent Susan Bellville Bellville Realty

    2591 Chapel Rd, Bennington, VT 05201
    • /40

      Est $122,103 Not Listed For Sale

      51 Chiselville Rd, Arlington, VT 05250

      • 2 Beds
      • 2 Baths
      • 540 Sq Ft
      • Built 1820
      51 Chiselville Rd, Arlington, VT 05250

      Last Sold Summary

      • 36% Above List Price
      • $167/SF
      • 6 Days On Market

      Last Sold Price $90,000

      Last Listing Agent Nicholas Charest Maple Leaf Realty

  • /27

    $549,000

    • 2 Beds
    • 2 Baths
    • 3,478 Sq Ft

    142 Mount Aeolus Rd, Manchester, VT 05255

    A Rare Investment Opportunity in Manchester! This versatile property offers the perfect blend of commercial and residential potential, making it an ideal choice for savvy investors or those seeking a live-work setup. The upstairs features a spacious residential rental, while the lower level was recently leased to a local daycare, providing immediate rental income.This well-maintained property

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    142 Mount Aeolus Rd, Manchester, VT 05255
  • /55

    $762,000 Sold Nov 03, 2025

    3221 Hapgood Pond Rd, Peru, VT 05152

    • 4 Beds
    • 4 Baths
    • 2,868 Sq Ft
    • Built 1950

    Last Sold Summary

    • 17% Above List Price
    • $266/SF
    • 6 Days On Market

    Current Estimated Value $743,612

    Last Listing Agent Jamie Wylie Stratton Real Estate

    3221 Hapgood Pond Rd, Peru, VT 05152
    • /18

      Est $582,176 Not Listed For Sale

      55 Wildflower Ln, Arlington, VT 05250

      • 3 Beds
      • 2.5 Baths
      • 2,514 Sq Ft
      • Built 1997
      55 Wildflower Ln, Arlington, VT 05250

      Last Sold Summary

      • 6% Above List Price
      • $219/SF
      • 46 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Sean Dillon Real Broker LLC

  • /43

    $540,000

    • 3 Beds
    • 2 Baths
    • 3,196 Sq Ft

    1858 King Hill Rd, Readsboro, VT 05350

    Come see this pristine, newly renovated 3 bedroom, 2 bath home set on 7.58 private acres. The current owner has thoughtfully enhanced the property with numerous upgrades, including fresh exterior paint, an oversized wraparound deck, a poured concrete garage floor, new high efficiency water heater, and wood stove inserts in both the main level and lower level fireplaces. Mini splits provide

    Prema Fitzpatrick Real Broker LLC

    1858 King Hill Rd, Readsboro, VT 05350
  • /45

    $593,000 Sold Mar 18, 2025

    109 Mad Tom Rd, East Dorset, VT 05253

    • 4 Beds
    • 2 Baths
    • 2,986 Sq Ft
    • Built 1860

    Last Sold Summary

    • 15% Below List Price
    • $199/SF
    • 99 Days On Market

    Current Estimated Value $597,384

    Last Listing Agent Julie Citron RE/MAX Four Seasons

    109 Mad Tom Rd, East Dorset, VT 05253
    • /37

      Est $464,298 Not Listed For Sale

      127 Flynn Hollow Rd, Sunderland, VT 05250

      • 3 Beds
      • 1.5 Baths
      • 1,718 Sq Ft
      • Built 1989
      127 Flynn Hollow Rd, Sunderland, VT 05250

      Last Sold Summary

      • 23% Below List Price
      • $352/SF
      • 3 Days On Market

      Last Sold Price $605,000

      Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  • /40

    $549,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 4,044 Sq Ft

    5515 Main St, Manchester, VT 05255

    Own a piece of Vermont history with this charming 1830s home, perfectly situated on Main Street in downtown. Zoned for mixed use (MU2), this versatile property offers endless possibilities-live, work, or do both in one inspiring space. The 2-bedroom, 2-bath home blends vintage Vermont character with modern comfort, featuring mini-splits for heating and cooling, a propane stove, fiber optic

    Katherine Zilkha Four Seasons Sotheby's Int'l Realty

    5515 Main St, Manchester, VT 05255
  • /11

    $163,000 Sold Jul 18, 2025

    237 Church St, Pownal, VT 05261

    • 2 Beds
    • 1 Bath
    • 780 Sq Ft
    • Built 1937

    Last Sold Summary

    • 2% Above List Price
    • $209/SF
    • 70 Days On Market

    Current Estimated Value $186,711

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

    237 Church St, Pownal, VT 05261
    • /34

      Est $207,626 Not Listed For Sale

      925 South Rd, East Arlington, VT 05252

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1972
      925 South Rd, East Arlington, VT 05252

      Last Sold Summary

      • 43% Above List Price
      • $108/SF
      • 6 Days On Market

      Last Sold Price $145,000

      Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  • /47

    $525,000

    • 5 Beds
    • 4 Baths
    • 2,244 Sq Ft

    706 Jefferson Heights, Bennington, VT 05201

    Mountain views, walkable access to downtown Bennington, and a complete 2023 renovation make this beautifully reimagined home a rare turnkey opportunity in one of the area’s most desirable neighborhoods. Smartly redesigned from the inside out with an emphasis on quality, comfort, and long-term efficiency, resulting in a fully refreshed interior with modern systems and an effortless flow throughout

    Jenifer Prouty Hoffman Hoffman Real Estate

    706 Jefferson Heights, Bennington, VT 05201
  • /34

    $725,000 Sold Apr 01, 2025

    235 Kestrel Ct Unit F-14, Manchester, VT 05254

    • 3 Beds
    • 3 Baths
    • 2,924 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $248/SF
    • 130 Days On Market

    Last Listing Agent Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    235 Kestrel Ct Unit F-14, Manchester, VT 05254
    • /25

      Est $438,448 Not Listed For Sale

      125 Chiselville Rd, Arlington, VT 05250

      • 4 Beds
      • 4 Baths
      • 1,593 Sq Ft
      • Built 1880
      125 Chiselville Rd, Arlington, VT 05250

      Last Sold Summary

      • 3% Below List Price
      • $282/SF
      • 31 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

  • /37

    $995,000

    • 4,724 Sq Ft

    1594 Vermont Route 7a, Shaftsbury, VT 05262

    Welcome to a truly unique and versatile property situated on 5 beautiful acres, offering a rare combination of residential comfort, business potential, and rental income. The main residence is a spacious 2,100 square foot home seamlessly connected to a large, fully equipped garage. This garage is a dream for automotive professionals or hobbyists, featuring two vehicle lifts, a high-ceilinged

    Kelley Mccarthy Mahar McCarthy Real Estate

    1594 Vermont Route 7a, Shaftsbury, VT 05262

Showing Results 161 - 200, Page 5 of 18

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