Bennington County, VT Homes

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  /4

  $35,000 Sold Jan 20, 2026

  0 Oberhugel Rd Unit 5059139, Stamford, VT 05352

  • Land
  • 2 Acres
  • $17,500 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 106 Days On Market

  Last Listing Agent Duncan Honig Maple Leaf Realty

  0 Oberhugel Rd Unit 5059139, Stamford, VT 05352
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  /29

  Est $1,267,379 Not Listed For Sale

  667 Canterbury Rd, Manchester Center, VT 05255

  • 5 Beds
  • 5 Baths
  • 4,016 Sq Ft
  • Built 1990

  667 Canterbury Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 69% Above List Price
  • $187/SF
  • 42 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Andy Reed Four Seasons Sotheby's Int'l Realty
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  /25

  $975,000

  • 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
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  /55

  $707,500 Sold Jul 17, 2025

  697 Hamilton Hollow Rd, Arlington, VT 05250

  • 3 Beds
  • 2.5 Baths
  • 2,944 Sq Ft
  • Built 1997

  Last Sold Summary

  • 2% Below List Price
  • $240/SF
  • 55 Days On Market

  Current Estimated Value $707,431

  Last Listing Agent Faith Rhodes Maple Leaf Realty

  697 Hamilton Hollow Rd, Arlington, VT 05250
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  /31

  Est $621,934 Not Listed For Sale

  350 Carlen St, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 2,177 Sq Ft
  • Built 1988

  350 Carlen St, Manchester Center, VT 05255

  Last Sold Summary

  • 15% Above List Price
  • $248/SF
  • 170 Days On Market

  Last Sold Price $539,000

  Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty
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  /2

  $2,190,000

  • Land
  • 1.16 Acres
  • $1,887,931 per Acre

  301 Northside Dr, Bennington, VT 05201

  Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

  Paul Carroccio TPW Real Estate

  301 Northside Dr, Bennington, VT 05201
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  /60

  $1,300,000 Sold Dec 10, 2025

  694 Sykes Hollow Rd, Rupert, VT 05776

  • 3 Beds
  • 2.5 Baths
  • 2,259 Sq Ft
  • Built 1789

  Last Sold Summary

  • 2% Above List Price
  • $575/SF
  • 15 Days On Market

  Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  694 Sykes Hollow Rd, Rupert, VT 05776
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  /40

  Est $701,024 Not Listed For Sale

  190 Meadow Ridge Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 2,564 Sq Ft
  • Built 1985

  190 Meadow Ridge Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 27% Above List Price
  • $215/SF
  • 59 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.
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  /29

  $250,000

  • 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
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  /26

  $193,500 Sold Aug 06, 2025

  305 Weeks St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft
  • Built 1937

  Last Sold Summary

  • 3% Below List Price
  • $119/SF
  • 17 Days On Market

  Current Estimated Value $200,911

  Last Listing Agent Matt Waddington Hoffman Real Estate

  305 Weeks St, Bennington, VT 05201
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  /26

  Est $728,457 Not Listed For Sale

  373 Hillcrest Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 2,124 Sq Ft
  • Built 1986

  373 Hillcrest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 9% Below List Price
  • $377/SF
  • 4 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home
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  /50

  $259,000

  • 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
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  /55

  $800,000 Sold Nov 17, 2025

  879 River Rd, Manchester, VT 05255

  • 3 Beds
  • 3.5 Baths
  • 2,340 Sq Ft
  • Built 1900

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 34 Days On Market

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

  879 River Rd, Manchester, VT 05255
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  /32

  Est $588,297 Not Listed For Sale

  251 Hillcrest Rd, Manchester Center, VT 05255

  • 3 Beds
  • 3.5 Baths
  • 2,084 Sq Ft
  • Built 1986

  251 Hillcrest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 12% Above List Price
  • $253/SF
  • 18 Days On Market

  Last Sold Price $526,500

  Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty
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  /22

  $895,000

  • Land
  • 24.08 Acres
  • $37,168 per Acre

  A Windsor Rd, Manchester, VT 05255

  Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

  Kim Morgan-Wohler Wohler Realty Group

  A Windsor Rd, Manchester, VT 05255
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  /15

  $640,000 Sold Feb 26, 2026

  105 Elm St, Manchester, VT 05255

  • 5 Beds
  • 4 Baths
  • 3,732 Sq Ft
  • Built 1850

  Last Sold Summary

  • $171/SF
  • 2 Days On Market

  Last Listing Agent David Citron RE/MAX Four Seasons

  105 Elm St, Manchester, VT 05255
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  /36

  Est $612,344 Not Listed For Sale

  64 Mears Ln, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 1988

  64 Mears Ln, Manchester Center, VT 05255

  Last Sold Summary

  • 17% Above List Price
  • $394/SF
  • 5 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.
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  /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
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  /38

  $291,065 Sold Jul 11, 2025

  121 Fillmore St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1946

  Last Sold Summary

  • 1% Above List Price
  • $168/SF
  • 66 Days On Market

  Current Estimated Value $292,007

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  121 Fillmore St, Bennington, VT 05201
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  /26

  Est $587,948 Not Listed For Sale

  84 Green Mountain Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 2,182 Sq Ft
  • Built 1992

  84 Green Mountain Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 16% Above List Price
  • $231/SF
  • 15 Days On Market

  Last Sold Price $505,000

  Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty
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  /17

  $79,900

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  108 Baker Dr, Bennington, VT 01237

  Built in 2000 this charming home is located in Catamount Mobile Home Park, a community with no age restrictions in beautiful Bennington, Vermont. Situated on a large corner lot with front and back decks offering mountain views. Open, light-filled floor plan with bright kitchen, living room, primary suite, second bedroom, full bath, and laundry. Features include anewer shed (1 year old) and

  Colleen Zajac MONARCH REALTY, INC.

  108 Baker Dr, Bennington, VT 01237
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  /60

  $235,000 Sold May 20, 2025

  1304 Vermont Route 100, Readsboro, VT 05350

  • Land
  • 5 Acres
  • $47,000 per Acre

  Last Sold Summary

  • 88 Days On Market

  Last Listing Agent Lisa Friedman Great American Dream Realty

  1304 Vermont Route 100, Readsboro, VT 05350
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  /23

  Est $554,826 Not Listed For Sale

  70 Hillcrest Rd, Manchester Center, VT 05255

  • 4 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1978

  70 Hillcrest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 30% Above List Price
  • $257/SF
  • 4 Days On Market

  Last Sold Price $427,500

  Last Listing Agent Charles Mauro Josiah Allen Real Estate, Inc.
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  /41

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  7 Roundtree Rd, Winhall, VT 05340

  Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  7 Roundtree Rd, Winhall, VT 05340
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  /14

  $20,000 Sold Oct 30, 2025

  79 Skytop Dr Unit 6, Bennington, VT 05201

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft
  • Built 1950

  Last Sold Summary

  • 27% Below List Price
  • $36/SF
  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  79 Skytop Dr Unit 6, Bennington, VT 05201
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  /35

  Est $771,447 Not Listed For Sale

  2529 Main St, Manchester Center, VT 05255

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft
  • Built 1780

  2529 Main St, Manchester Center, VT 05255

  Last Sold Summary

  • 6% Above List Price
  • $290/SF
  • 9 Days On Market

  Last Sold Price $731,000

  Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty
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  /4

  $28,000

  • Land
  • 2.3 Acres
  • $12,174 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own a

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /39

  $615,000 Sold Mar 12, 2025

  81 Pond View Rd Unit 81, Winhall, VT 05340

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $373/SF
  • 32 Days On Market

  Current Estimated Value $617,341

  Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  81 Pond View Rd Unit 81, Winhall, VT 05340
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  /41

  Est $575,147 Not Listed For Sale

  1565 E Manchester Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • Built 1967

  1565 E Manchester Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 7% Above List Price
  • $259/SF
  • 5 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Jessica Citera Cummings & Co
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  /24

  $471,000

  • 3 Beds
  • 2 Baths
  • 1,357 Sq Ft

  102 Mccormick Ln, Sunderland, VT 05250

  Built in 2003, the home's open-concept design is highlighted by a bright and airy living/dining/kitchen area, where large windows flood the space with abundant natural light. A cozy pellet stove provides warmth and ambiance for those crisp Vermont evenings. The functional layout features two comfortable bedrooms and a full bathroom on the main level, while the private primary ensuite bedroom

  Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

  102 Mccormick Ln, Sunderland, VT 05250
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  /39

  $825,000 Sold Jul 11, 2025

  2844 Main St, Manchester, VT 05254

  • 4 Beds
  • 3.5 Baths
  • 3,002 Sq Ft
  • Built 1958

  Last Sold Summary

  • 6% Below List Price
  • $275/SF
  • 63 Days On Market

  Current Estimated Value $853,009

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

  2844 Main St, Manchester, VT 05254
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  /11

  Est $591,342 Not Listed For Sale

  470 Johnnycake St, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Built 1950

  470 Johnnycake St, Manchester Center, VT 05255

  Last Sold Summary

  • 6% Above List Price
  • $354/SF
  • 41 Days On Market

  Last Sold Price $557,500

  Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty
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  /34

  $249,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,810 Sq Ft

  3530 Vt Route 346, Pownal, VT 05261

  This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially

  Matt Waddington Hoffman Real Estate

  3530 Vt Route 346, Pownal, VT 05261
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  /35

  $662,500 Sold Apr 29, 2025

  139 Franklin Ave, Manchestr Ctr, VT 05255

  • 4 Beds
  • 3 Baths
  • 3,222 Sq Ft
  • Built 1910

  Last Sold Summary

  • 22% Below List Price
  • $206/SF
  • 210 Days On Market

  Last Listing Agent Peter Pierce EXP Realty

  139 Franklin Ave, Manchestr Ctr, VT 05255
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  /40

  Not Listed For Sale

  658 Finbars Forest Rd, Manchester Center, VT 05255

  • 5 Beds
  • 4 Baths
  • 2,602 Sq Ft
  • Built 1989

  658 Finbars Forest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • $250/SF
  • 5 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Lindsey Pinder Josiah Allen Real Estate, Inc.
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  /36

  $355,000

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft

  149 Jewett Dr, Bennington, VT 05201

  Tucked just outside of town with sweeping views in every direction, this 4-bedroom, 2-bath raised ranch offers the space and setting you're looking for. Hardwood floors run throughout the main level, where the sun-filled living room features a cozy wood-burning fireplace—perfect for gathering on chilly evenings. The finished lower level provides flexible space to grow, including the third and

  Faith Rhodes Maple Leaf Realty

  149 Jewett Dr, Bennington, VT 05201
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  /2

  $205,000 Sold Sep 15, 2025

  24 Stratton Rd W, Winhall, VT 05340

  • 2 Beds
  • 1 Bath
  • 665 Sq Ft
  • Built 1970

  Last Sold Summary

  • $308/SF
  • 0 Days On Market

  Current Estimated Value $207,165

  Last Listing Agent Cheyanne Pugliese

  24 Stratton Rd W, Winhall, VT 05340
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  /32

  Est $952,117 Not Listed For Sale

  1145 Powderhorn Rd, Manchester Center, VT 05255

  • 4 Beds
  • 3.5 Baths
  • 3,728 Sq Ft
  • Built 1983

  1145 Powderhorn Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 18% Above List Price
  • $216/SF
  • 109 Days On Market

  Last Sold Price $806,250

  Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty
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  /28

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,610 Sq Ft

  3622 Dorset West Rd, Dorset, VT 05251

  Unique Dorset West Road offering....This rare opportunity beckons creativity,craft, and charm! Begs all those ready, willing and able to renovate, keeping the existing home, whilst enjoying life in an extremely beautiful and desirable location. Enjoy the beautiful framed in mountain views from most interior living spaces and from the back patio/yard. This 6.6 acre rolling property boasts

  Sunny Breen Josiah Allen Real Estate, Inc.

  3622 Dorset West Rd, Dorset, VT 05251
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  /54

  $80,000 Sold Dec 09, 2025

  889 Overlea Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $87/SF
  • 4 Days On Market

  Last Listing Agent Catherine Cairns Maple Leaf Realty

  889 Overlea Rd, Bennington, VT 05201

Showing Results 521 - 560, Page 14 of 18