Bennington County, VT Homes

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  /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
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  /30

  $400,000 Sold Oct 15, 2025

  38 Spruce Ln, Arlington, VT 05250

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Below List Price
  • $248/SF
  • 0 Days On Market

  Current Estimated Value $379,173

  Last Listing Agent Lori Hurley Four Corner Properties LLC

  38 Spruce Ln, Arlington, VT 05250
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  /31

  Est $415,800 Not Listed For Sale

  1388 Pawlet Mountain Rd, Pawlet, VT 05761

  • 1 Bed
  • 1 Bath
  • 1,088 Sq Ft
  • Built 2004

  1388 Pawlet Mountain Rd, Pawlet, VT 05761

  Last Sold Summary

  • 7% Above List Price
  • $358/SF
  • 20 Days On Market

  Last Sold Price $390,000

  Last Listing Agent Suanne Ohl Northland Real Estate
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  /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
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  /38

  $635,000 Sold Nov 21, 2025

  825 Case Ln, Readsboro, VT 05350

  • 3 Beds
  • 2 Baths
  • 2,499 Sq Ft
  • Built 2006

  Last Sold Summary

  • 15% Above List Price
  • $254/SF
  • 7 Days On Market

  Current Estimated Value $592,762

  Last Listing Agent Melissa Nebelski Real Broker LLC

  825 Case Ln, Readsboro, VT 05350
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  /30

  Est $374,739 Not Listed For Sale

  513 Sykes Hollow Rd, Pawlet, VT 05761

  • 3 Beds
  • 1 Bath
  • 1,764 Sq Ft
  • Built 1930

  513 Sykes Hollow Rd, Pawlet, VT 05761

  Last Sold Summary

  • 11% Above List Price
  • $192/SF
  • 2 Days On Market

  Last Sold Price $338,500

  Last Listing Agent Donna Murray Varick Associates Ltd
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  /5

  $350,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  525 Jennings Brook Dr, Bennington, VT 05201

  Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

  Lilli West Maple Leaf Realty

  525 Jennings Brook Dr, Bennington, VT 05201
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  /44

  $275,000 Sold Jan 23, 2026

  211 Grandview St, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $149/SF
  • 21 Days On Market

  Current Estimated Value $281,222

  Last Listing Agent Colt Hazell Flex Realty

  211 Grandview St, North Bennington, VT 05257
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  /33

  Est $189,516 Not Listed For Sale

  476 Tunnel St, Readsboro, VT 05350

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1880

  476 Tunnel St, Readsboro, VT 05350

  Last Sold Summary

  • 5% Above List Price
  • $136/SF
  • 20 Days On Market

  Last Sold Price $180,000

  Last Listing Agent Jacki Murano Southern Vermont Realty Group
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  /21

  $125,000

  • Land
  • 4 Acres
  • $31,250 per Acre

  773 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

  Set on 4 scenic acres in Shaftsbury Hollow, this special property offers a rare blend of open pasture, mature woodland, and frontage along the Little White Creek. The setting is both peaceful and recreational—ideal for those seeking a true Vermont escape. Enjoy natural shade along the water’s edge, spend summer days swimming or casting for brook trout, and gather around the campfire under the

  Jenifer Prouty Hoffman Hoffman Real Estate

  773 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
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  /36

  $265,000 Sold Jun 25, 2025

  82 Oakes St, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,512 Sq Ft
  • Built 1991

  Last Sold Summary

  • $175/SF
  • 57 Days On Market

  Current Estimated Value $269,266

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  82 Oakes St, Bennington, VT 05201
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  /13

  Est $265,058 Not Listed For Sale

  390 Tunnel St, Readsboro, VT 05350

  • 4 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Built 1968

  390 Tunnel St, Readsboro, VT 05350

  Last Sold Summary

  • 27% Above List Price
  • $125/SF
  • 3 Days On Market

  Last Sold Price $209,000

  Last Listing Agent Derek Greene Derek Greene
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  /59

  $3,475,000

  • 5 Beds
  • 4.5 Baths
  • 5,905 Sq Ft

  220 Camptown Rd, Manchester Center, VT 05255

  Set high on a hillside overlooking a picturesque horse farm, this exceptional Manchester property captures far-reaching mountain views and covetous privacy. Nearly 39 acres of sweeping lawn and open meadow transition into wooded terrain, with direct access to over 1,000 acres of conserved land leading to Mount Equinox and Myrick Mountain in the Equinox Highlands. Trails on the property and

  Christiane Carroccio TPW Real Estate

  220 Camptown Rd, Manchester Center, VT 05255
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  /43

  $1,590,000 Sold Oct 23, 2025

  81 Pine Tree Ln, Manchester Center, VT 05255

  • 4 Beds
  • 3.5 Baths
  • 3,926 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $405/SF
  • 17 Days On Market

  Current Estimated Value $1,526,025

  Last Listing Agent Roger Danyew Diamond Realty

  81 Pine Tree Ln, Manchester Center, VT 05255
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  /39

  Est $264,574 Not Listed For Sale

  93 Depot St, Readsboro, VT 05350

  • 4 Beds
  • 2 Baths
  • 1,837 Sq Ft
  • Built 1800

  93 Depot St, Readsboro, VT 05350

  Last Sold Summary

  • 18% Above List Price
  • $122/SF
  • 1 Day On Market

  Last Sold Price $225,000

  Last Listing Agent Melissa Nebelski Real Broker LLC
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  /9

  $27,500

  • Land
  • 1.2 Acres
  • $22,917 per Acre

  0 Bergrucken Ln Unit 5044034, Stamford, VT 05352

  Trade city sirens for wind-rustled maples on this gently wooded 1.2-acre lot tucked inside Alpenwald Village. Alpenwald, although deed restricted, the light protective covenants keep the area tidy without cramping your architectural imagination. Think A-Frame, modern farmhouse, or a passive solar cottage. Beyond the lot is access to trails that lace through the Green Mountain National Forest.

  Kelly Agrillo Southern Vermont Realty Group

  0 Bergrucken Ln Unit 5044034, Stamford, VT 05352
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  /16

  $130,000 Sold Jan 28, 2026

  755 Main St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft
  • Built 1890

  Last Sold Summary

  • 10% Below List Price
  • $88/SF
  • 141 Days On Market

  Current Estimated Value $171,656

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

  755 Main St, Bennington, VT 05201
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  /18

  Est $152,006 Not Listed For Sale

  78 Canal Dr, Readsboro, VT 05350

  • 3 Beds
  • 2 Baths
  • 1,024 Sq Ft
  • Built 1880

  78 Canal Dr, Readsboro, VT 05350

  Last Sold Summary

  • 134% Above List Price
  • $63/SF
  • 178 Days On Market

  Last Sold Price $65,000

  Last Listing Agent Duncan Honig Maple Leaf Realty
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  /43

  $2,100,000

  • 4 Beds
  • 3 Baths
  • 3,780 Sq Ft

  1228 Skiparee Rd, Pownal, VT 05260

  Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

  Christiane Carroccio TPW Real Estate

  1228 Skiparee Rd, Pownal, VT 05260
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  /11

  $780,000 Sold Mar 23, 2026

  0 W Sandgate Rd, Sandgate, VT 05250

  • Land
  • 663.95 Acres
  • $1,175 per Acre

  Last Sold Summary

  • 110 Days On Market

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

  0 W Sandgate Rd, Sandgate, VT 05250
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  /40

  Est $563,463 Not Listed For Sale

  1456 Branch Hill Rd, Readsboro, VT 05350

  • 3 Beds
  • 2 Baths
  • 3,263 Sq Ft
  • Built 1991

  1456 Branch Hill Rd, Readsboro, VT 05350

  Last Sold Summary

  • 16% Above List Price
  • $149/SF
  • 856 Days On Market

  Last Sold Price $487,000

  Last Listing Agent Christine Lewis Brattleboro Area Realty
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  /60

  $579,900

  • 1 Bed
  • 1 Bath
  • 2,529 Sq Ft

  126 Simeon Dean Rd, Shaftsbury, VT 05262

  Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete

  Denise Byers Green Mountain Premiere Properties

  126 Simeon Dean Rd, Shaftsbury, VT 05262
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  /23

  $110,000 Sold Mar 26, 2026

  4697 Main Rd, Stamford, VT 05352

  • 4 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • Built 1940

  Last Sold Summary

  • 35% Below List Price
  • $69/SF
  • 161 Days On Market

  Current Estimated Value $239,333

  Last Listing Agent Dick Thackston R.H. Thackston & Company

  4697 Main Rd, Stamford, VT 05352
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  /40

  Est $379,953 Not Listed For Sale

  1693 Branch Hill Rd, Readsboro, VT 05350

  • 3 Beds
  • 3 Baths
  • 2,259 Sq Ft
  • Built 1848

  1693 Branch Hill Rd, Readsboro, VT 05350

  Last Sold Summary

  • 9% Above List Price
  • $155/SF
  • 14 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Monique White Deerfield Valley Real Estate
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  /27

  $645,000

  • 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
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  /38

  $215,000 Sold Jun 06, 2025

  230 Beech St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1880

  Last Sold Summary

  • 4% Below List Price
  • $169/SF
  • 81 Days On Market

  Current Estimated Value $218,908

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  230 Beech St, Bennington, VT 05201
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  /15

  Est $441,522 Not Listed For Sale

  833 Freezing Hole Dr, Readsboro, VT 05350

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft
  • Built 1997

  833 Freezing Hole Dr, Readsboro, VT 05350

  Last Sold Summary

  • 2% Above List Price
  • $254/SF
  • 9 Days On Market

  Last Sold Price $432,500

  Last Listing Agent Kristen Breeden Southern Vermont Realty Group
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  /20

  $179,900 Pending

  • 4 Beds
  • 1.5 Baths
  • 2,082 Sq Ft

  266 Robillard Rd, Stamford, VT 05352

  SOUTHERN VERMONT!~ PRICE DROP $45,000!! Great country location with over a 1/2 acre of beautiful lawns & perennial flower. Sitting porch, large kitchen with pantry opens to dining & living room. Oak hardwood floors on 1st floor. 2nd level has 4 good sized bedrooms & 3rd level has a private loft area with 2 very nice rooms & a 1/2 bath - great office space, laundry room or meditation room. Laundry

  Colleen Zajac Monarch Realty

  266 Robillard Rd, Stamford, VT 05352
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  /29

  $350,000 Sold Jun 10, 2025

  297 Mad Tom Rd, East Dorset, VT 05253

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Above List Price
  • $257/SF
  • 46 Days On Market

  Current Estimated Value $346,431

  Last Listing Agent Sandy Reavill

  297 Mad Tom Rd, East Dorset, VT 05253
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  /40

  Est $397,102 Not Listed For Sale

  470 Freezing Hole Dr, Readsboro, VT 05350

  • 3 Beds
  • 1.5 Baths
  • 1,064 Sq Ft
  • Built 1964

  470 Freezing Hole Dr, Readsboro, VT 05350

  Last Sold Summary

  • 1% Below List Price
  • $376/SF
  • 8 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Monique White Deerfield Valley Real Estate
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  /12

  $399,500

  • Land
  • 2.7 Acres
  • $147,963 per Acre

  2937 Dorset Rd W, Dorset, VT 05251

  Prime Buildable Lot in Dorset! Embrace the Best of All Worlds! Discover a rare opportunity to own a ready-to-build lot in the heart of Dorset, perfectly positioned to offer unparalleled access to the town's finest attractions. Just moments from scenic hiking trails, the picturesque Dorset Green, and the esteemed Dorset Field Club, this property is your gateway to a lifestyle of outdoor adventure

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  2937 Dorset Rd W, Dorset, VT 05251
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  /2

  $450,000 Sold May 23, 2025

  20 Harvest Hills Dr, North Bennington, VT 05257

  • 4 Beds
  • 2.5 Baths
  • 1,660 Sq Ft
  • Built 1972

  Last Sold Summary

  • $271/SF
  • 0 Days On Market

  Current Estimated Value $430,419

  Last Listing Agent Floyd Amidon Maple Leaf Realty

  20 Harvest Hills Dr, North Bennington, VT 05257
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  /35

  Not Listed For Sale

  140 Odonnell Dr, Readsboro, VT 05350

  • 4 Beds
  • 3 Baths
  • 2,560 Sq Ft
  • Built 2000

  140 Odonnell Dr, Readsboro, VT 05350

  Last Sold Summary

  • $217/SF
  • 6 Days On Market

  Last Sold Price $555,000

  Last Listing Agent Monica Sumner BHG Masiello Brattleboro
• 

  

  /23

  $249,000

  • Land
  • 17.6 Acres
  • $14,148 per Acre

  88 Cedar Ln, Peru, VT 05152

  Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

  Joe Castaluccio Winhall Real Estate

  88 Cedar Ln, Peru, VT 05152
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  /8

  $71,200 Sold Oct 09, 2025

  272 Twenty Acre Wood Rd, Arlington, VT 05250

  • Land
  • 7.12 Acres
  • $10,000 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 58 Days On Market

  Current Estimated Value $69,825

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

  272 Twenty Acre Wood Rd, Arlington, VT 05250
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  /20

  Est $372,030 Not Listed For Sale

  603 Wiley Mountain Dr, Readsboro, VT 05350

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 2005

  603 Wiley Mountain Dr, Readsboro, VT 05350

  Last Sold Summary

  • 3% Below List Price
  • $401/SF
  • 160 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Melissa Nebelski Real Broker LLC
• 

  

  /40

  $198,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,201 Sq Ft

  317 Pleasant St, Bennington, VT 05201

  Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400). Unit 1 on the

  Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
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  /35

  $279,000 Sold Aug 07, 2025

  65 Mountain View Dr, Shaftsbury, VT 05262

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $160/SF
  • 30 Days On Market

  Last Listing Agent Dan Mason Perrott Realty

  65 Mountain View Dr, Shaftsbury, VT 05262
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  /24

  Est $347,654 Not Listed For Sale

  1680 W Hill Dr, Readsboro, VT 05350

  • 4 Beds
  • Built 1980

  1680 W Hill Dr, Readsboro, VT 05350

  Last Sold Summary

  • 39% Above List Price
  • $116/SF
  • 409 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Christine Lewis Brattleboro Area Realty
• 

  

  /27

  $290,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,190 Sq Ft

  196 Granger Hollow Rd, North Bennington, VT 05257

  Currently being used as a primary home with in-law rental 2nd home, this property could easily transition into a 2 unit multifamily with 2 separate houses with your tenants paying all utilities responsible for their own plowing and yard upkeep. This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large

  Steve Schoppmeyer BHG Masiello Brattleboro

  196 Granger Hollow Rd, North Bennington, VT 05257

Showing Results 401 - 440, Page 11 of 18