21,114

Bennington County, VT Homes

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  • /15

    $500,000

    • Land
    • 21.2 Acres
    • $23,585 per Acre

    56 Lower Taylor Hill Rd, Winhall, VT 05340

    A rare opportunity to create a private Vermont retreat on 21.2 +/- acres along Lower Taylor Hill Road in Winhall. The property is supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, offering flexibility to design a substantial home within permitted limits. Rolling terrain, natural clearings, and mature woodland provide multiple potential building sites,

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    56 Lower Taylor Hill Rd, Winhall, VT 05340
  • /22

    $175,000 Sold Sep 11, 2025

    6967 Main St, Readsboro, VT 05350

    • 6 Beds
    • 2 Baths
    • 2,116 Sq Ft
    • Built 1870

    Last Sold Summary

    • 22% Below List Price
    • $83/SF
    • 70 Days On Market

    Current Estimated Value $181,150

    Last Listing Agent Cassandra Ehrlich BHG Masiello Brattleboro

    6967 Main St, Readsboro, VT 05350
    • /43

      Est $539,692 Not Listed For Sale

      78 Stoney Fields Rd, Manchester Center, VT 05255

      • 4 Beds
      • 2.5 Baths
      • 1,710 Sq Ft
      • Built 1964
      78 Stoney Fields Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 15% Above List Price
      • $275/SF
      • 61 Days On Market

      Last Sold Price $470,000

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

  • /55

    $995,000

    • 5 Beds
    • 4.5 Baths
    • 2,321 Sq Ft

    24 N Branch Rd, Winhall, VT 05340

    Exceptional Renovation of a Stratton Resort Residence in the Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite- this mountain chalet has been updated

    Kim Morgan-Wohler Wohler Realty Group

    24 N Branch Rd, Winhall, VT 05340
  • /53

    $495,000 Sold Oct 17, 2025

    200 Applewood Ln, Manchester Center, VT 05255

    • 2,746 Sq Ft
    • Built 1986

    Last Sold Summary

    • $180/SF
    • 4 Days On Market

    Current Estimated Value $500,488

    Last Listing Agent Zachary Zupan EXP Realty

    200 Applewood Ln, Manchester Center, VT 05255
    • /31

      Est $456,894 Not Listed For Sale

      6344 Main St, Manchester Center, VT 05255

      • 2 Beds
      • 1 Bath
      • 1,244 Sq Ft
      • Built 1950
      6344 Main St, Manchester Center, VT 05255

      Last Sold Summary

      • 8% Above List Price
      • $342/SF
      • 4 Days On Market

      Last Sold Price $425,000

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /9

    $550,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,293 Sq Ft

    18 Jameson Flats Rd Unit 18, Manchester, VT 05255

    PUBLIC OPEN HOUSE: THIS SATURDAY OCTOBER 11th Noon-2pm THE PROGRAM: Purchase Price Assistance/ Mortgage Payment Reduction: Eligibility Requirements:* Vermont Residency or Residency at time ofPurchase* First Time Vermont Homebuyer* Household Income at or Below $178,735** Qualify for a Bank Mortgage* 10% Down PaymentThe developer will offer Gifted Equity andPaid

    Britt Wohler

    18 Jameson Flats Rd Unit 18, Manchester, VT 05255
  • /48

    $239,900 Sold Jun 06, 2025

    213 Maple St, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft
    • Built 1910

    Last Sold Summary

    • $166/SF
    • 2 Days On Market

    Current Estimated Value $242,298

    Last Listing Agent Matt Waddington Hoffman Real Estate

    213 Maple St, Bennington, VT 05201
    • /34

      Est $846,045 Not Listed For Sale

      50 Ways Ln, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 3,196 Sq Ft
      • Built 1970
      50 Ways Ln, Manchester Center, VT 05255

      Last Sold Summary

      • 12% Above List Price
      • $236/SF
      • 13 Days On Market

      Last Sold Price $755,000

      Last Listing Agent Tyler Hirchak Land Sea Air Space Auction Group Inc

  • /6

    $99,000

    • Land
    • 1 Acre
    • $99,000 per Acre

    88A Sylvan Ridge Rd, Winhall, VT 05340

    Wooded lot with hardwoods, evergreens and birch trees. Potential views of Bromley Mountain and beyond. Town maintained road. Close to VAST snowmobile trails. Build your dream home in the Golden Triangle of ski areas, Stratton, Bromley, and Magic Mountains. Only 10 minuets to Manchester. Available on request:Wastewater System and Potable Water Supply PermitSeptic Site PlanCovenants

    Andrew King Stratton Real Estate

    88A Sylvan Ridge Rd, Winhall, VT 05340
  • /22

    $265,500 Sold Jul 15, 2025

    18 Stratton Ridge Rd, Winhall, VT 05340

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1970

    Last Sold Summary

    • 16% Below List Price
    • $199/SF
    • 72 Days On Market

    Last Listing Agent Derek Greene Derek Greene

    18 Stratton Ridge Rd, Winhall, VT 05340
    • /29

      Est $586,955 Not Listed For Sale

      271 Nottingham Park, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 1,422 Sq Ft
      • Built 1986
      271 Nottingham Park, Manchester Center, VT 05255

      Last Sold Summary

      • 7% Above List Price
      • $387/SF
      • 55 Days On Market

      Last Sold Price $550,000

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

  • /27

    $359,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    8 Winhall Woods Rd, Winhall, VT 05340

    Discover this quintessential Vermont ski chalet, perfectly set on a quiet dead-end road with views of Bromley Mountain from the property. Warm and inviting, the home is filled with natural wood throughout, creating the classic mountain-home atmosphere buyers love. Offering both charm and convenience, the location is ideal—just 2.5 miles to Bromley Mountain, 10 miles to Stratton, and only 8 miles

    Carrie Mathews Winhall Real Estate

    8 Winhall Woods Rd, Winhall, VT 05340
  • /48

    $306,250 Sold Dec 05, 2025

    4581 Main Rd, Stamford, VT 05352

    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft
    • Built 1967

    Last Sold Summary

    • 18% Above List Price
    • $149/SF
    • 21 Days On Market

    Current Estimated Value $300,160

    Last Listing Agent Susan Colvin MONARCH REALTY, INC.

    4581 Main Rd, Stamford, VT 05352
    • /21

      Est $358,294 Not Listed For Sale

      98 Highland Ave, Manchester Center, VT 05255

      • 3 Beds
      • 1 Bath
      • 1,824 Sq Ft
      • Built 1910
      98 Highland Ave, Manchester Center, VT 05255

      Last Sold Summary

      • 26% Above List Price
      • $156/SF
      • 124 Days On Market

      Last Sold Price $285,000

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

  • /56

    $2,300,000

    • 9 Beds
    • 8 Baths
    • 5,512 Sq Ft

    288 Cedar Ln, Peru, VT 05152

    Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

    Jessica Citera Cummings & Co

    288 Cedar Ln, Peru, VT 05152
  • /34

    $335,000 Sold Jun 09, 2025

    290 Springhill Rd, Bennington, VT 05201

    • 3 Beds
    • 2 Baths
    • 2,354 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $142/SF
    • 208 Days On Market

    Current Estimated Value $344,425

    Last Listing Agent Vicki Wilson Maple Leaf Realty

    290 Springhill Rd, Bennington, VT 05201
    • /6

      Est $379,809 Not Listed For Sale

      59 Bond St, Manchester Center, VT 05255

      • 3 Beds
      • 1.5 Baths
      • 1,536 Sq Ft
      • Built 1948
      59 Bond St, Manchester Center, VT 05255

      Last Sold Summary

      • 19% Above List Price
      • $208/SF
      • 6 Days On Market

      Last Sold Price $320,000

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

  • /34

    $270,000 Under Contract

    • 2,754 Sq Ft

    224 Union St, Bennington, VT 05201

    Well located three-unit property in downtown Bennington offering a strong opportunity for both investors and owner occupants. Two of the three units are currently occupied by long-term tenants in good standing, providing immediate and reliable income. The third and smallest unit has been intentionally left vacant for the past couple of months while the owner completed improvements, creating an

    Melissa Nebelski Real Broker LLC

    224 Union St, Bennington, VT 05201
  • /44

    $315,000 Sold Jun 20, 2025

    197 Crescent Blvd, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,248 Sq Ft
    • Built 1958

    Last Sold Summary

    • 7% Below List Price
    • $140/SF
    • 38 Days On Market

    Current Estimated Value $324,705

    Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

    197 Crescent Blvd, Bennington, VT 05201
    • /24

      Est $539,807 Not Listed For Sale

      159 Hillcrest Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 2,112 Sq Ft
      • Built 1972
      159 Hillcrest Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 11% Above List Price
      • $230/SF
      • 8 Days On Market

      Last Sold Price $485,000

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

  • /56

    $3,350,000

    • 3 Beds
    • 4.5 Baths
    • 3,059 Sq Ft

    466 3 Maple Dr, Manchester, VT 05254

    Welcome to Three Maple Drive, a beautifully crafted, brand-new single-family home nestled in a quiet and scenic location in Manchester, Vermont. Built in 2023 with impeccable attention to detail, this 3,059 sq ft modern farmhouse seamlessly blends luxury, comfort, and timeless design—all set on a private 3.85-acre lot with gorgeous mountain views.This home features three spacious bedroom

    David Shehadi Josiah Allen Real Estate, Inc.

    466 3 Maple Dr, Manchester, VT 05254
  • /32

    $645,000 Sold May 22, 2025

    409 Bromley Brook Rd, Manchester Center, VT 05255

    • 4 Beds
    • 2 Baths
    • 2,700 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Below List Price
    • $239/SF
    • 12 Days On Market

    Current Estimated Value $646,725

    Last Listing Agent Brian Hill Remax Summit

    409 Bromley Brook Rd, Manchester Center, VT 05255
    • /27

      Est $677,967 Not Listed For Sale

      211 Little John Dr, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,362 Sq Ft
      • Built 1980
      211 Little John Dr, Manchester Center, VT 05255

      Last Sold Summary

      • 2% Above List Price
      • $490/SF
      • 68 Days On Market

      Last Sold Price $667,500

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

  • /33

    $575,000 Under Contract

    • Land
    • 99.31 Acres
    • $5,790 per Acre

    000 Vermont 11, Peru, VT 05152

    Embrace the timeless beauty of Vermont with this exceptional 99.31-acre retreat. Nestled in the heart of picturesque Peru, Vermont, this expansive land parcel offers an extraordinary opportunity to own a slice of New England’s breathtaking landscapes. Surrounded by lush forests and bordering pristine national forest land, this property boasts timeless views of neighboring fields and the Green

    Kim Prins Four Seasons Sotheby's Int'l Realty

    000 Vermont 11, Peru, VT 05152
  • /16

    $25,000 Sold Jul 16, 2025

    0 Hawley Mountain Rd, Arlington, VT 05250

    • Land
    • 7 Acres
    • $3,571 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 15 Days On Market

    Last Listing Agent Faith Rhodes Maple Leaf Realty

    0 Hawley Mountain Rd, Arlington, VT 05250
    • /26

      Est $429,380 Not Listed For Sale

      37 Brookside Rd, Manchester Center, VT 05255

      • 3 Beds
      • 2 Baths
      • 1,268 Sq Ft
      • Built 1968
      37 Brookside Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 5% Above List Price
      • $323/SF
      • 26 Days On Market

      Last Sold Price $410,000

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

  • /37

    $585,000

    • 3 Beds
    • 2 Baths
    • 2,070 Sq Ft

    68 Owls Nest Cir Unit B-7, Manchester, VT 05254

    Special Price!! EOB Unit B-7!!! Equinox on the Battenkill, one of Southern Vermont’s premier condo/resort communities located in the historic village of scenic Manchester. This charming 3 bed 2 bath luxury town home, one of the select few with attached garages, offers the privacy of a quiet cul de sac, beautifully landscaped. Four seasons living in sought out neighborhood, Owls Nest! Management

    Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

    68 Owls Nest Cir Unit B-7, Manchester, VT 05254
  • /27

    $300,000 Sold Dec 11, 2025

    0 Rock Bottom Ln, Peru, VT 05152

    • Land
    • 53 Acres
    • $5,660 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 156 Days On Market

    Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

    0 Rock Bottom Ln, Peru, VT 05152
    • /31

      Est $544,165 Not Listed For Sale

      1 Cass Terrace, Manchester Center, VT 05255

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft
      • Built 1913
      1 Cass Terrace, Manchester Center, VT 05255

      Last Sold Summary

      • 6% Below List Price
      • $385/SF
      • 7 Days On Market

      Last Sold Price $577,000

      Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  • /47

    $245,000

    • 2 Beds
    • 2 Baths
    • 911 Sq Ft

    726 Rice Ln, Bennington, VT 05201

    Welcome to this charming Cape-style home, nestled in a peaceful country setting just moments from Bennington College and scenic walking and hiking trails. This inviting property offers the perfect blend of rural tranquility and convenient access to town. Located just 10 minutes from downtown Bennington, you’ll have quick access to local shops, restaurants, cultural attractions, and everyday

    Thomas Martins Maple Leaf Realty

    726 Rice Ln, Bennington, VT 05201
  • /47

    $240,000 Sold Sep 24, 2025

    120 Imperial Ave, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft
    • Built 1895

    Last Sold Summary

    • 20% Below List Price
    • $100/SF
    • 114 Days On Market

    Current Estimated Value $263,141

    Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

    120 Imperial Ave, Bennington, VT 05201
    • /40

      Est $1,053,576 Not Listed For Sale

      292 Johnnycake St, Manchester Center, VT 05255

      • 4 Beds
      • 3 Baths
      • 3,228 Sq Ft
      • Built 1984
      292 Johnnycake St, Manchester Center, VT 05255

      Last Sold Summary

      • 12% Above List Price
      • $293/SF
      • 100 Days On Market

      Last Sold Price $944,500

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

  • /30

    $349,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,845 Sq Ft

    1450 Vermont 8, Readsboro, VT 05350

    Charming Adirondack-style home set on 2.5 private acres, offering a warm, rustic aesthetic with thoughtful updates throughout. The main level features wood floors, an open cathedral ceiling with exposed beams, and a cozy woodstove anchoring the living space. The kitchen is ideal for entertaining with a large bar area, live-edge countertops, and an inviting open layout. An updated bathroom with a

    Kelley Mccarthy Mahar McCarthy Real Estate

    1450 Vermont 8, Readsboro, VT 05350
  • /29

    $350,000 Sold Apr 16, 2025

    202 Cedar Cir, Shaftsbury, VT 05262

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Above List Price
    • $185/SF
    • 3 Days On Market

    Current Estimated Value $351,653

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

    202 Cedar Cir, Shaftsbury, VT 05262
    • /24

      Est $570,225 Not Listed For Sale

      2071 Barnumville Rd, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 1,792 Sq Ft
      • Built 1980
      2071 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 14% Above List Price
      • $279/SF
      • 47 Days On Market

      Last Sold Price $500,000

      Last Listing Agent Robert Sabol Wohler Realty Group

  • /20

    $215,000

    • Land
    • 4.46 Acres
    • $48,206 per Acre

    OA E Manchester Rd, Manchester, VT 05255

    Very desirable lot off East Manchester Road with several building possibilities. Gently sloping, preliminary septic permit in place and access to all Manchester has to offer.

    Peter Pierce EXP Realty

    OA E Manchester Rd, Manchester, VT 05255
  • /50

    $675,000 Sold Nov 03, 2025

    7 Landgrove Rd, Landgrove, VT 05148

    • 4 Beds
    • 3 Baths
    • 2,570 Sq Ft
    • Built 1925

    Last Sold Summary

    • 12% Above List Price
    • $263/SF
    • 1 Day On Market

    Current Estimated Value $647,272

    Last Listing Agent Claudia Harris Mary Mitchell Miller Real Estate

    7 Landgrove Rd, Landgrove, VT 05148
    • /40

      Est $854,823 Not Listed For Sale

      2313 Barnumville Rd, Manchester Center, VT 05255

      • 3 Beds
      • 3 Baths
      • 3,891 Sq Ft
      • Built 1983
      2313 Barnumville Rd, Manchester Center, VT 05255

      Last Sold Summary

      • 143% Above List Price
      • $90/SF
      • 3 Days On Market

      Last Sold Price $352,000

      Last Listing Agent Patti Trudel RE/MAX

  • /38

    $502,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 2,400 Sq Ft

    1059 Bailey Hill Rd, Readsboro, VT 05350

    Welcome to Bailey Hill Road in Readsboro, Vermont. This farmhouse architecture style home with wood siding has 2400 squarefeet of finished living space. The interior features warm wood accentsthroughout, including exposed beams, wide plank and oak floors, and evena stained glass window created by a Vermont artisan. This home sits on a beautiful, private parcel of land that offers

    The Hammond Team KW Vermont

    1059 Bailey Hill Rd, Readsboro, VT 05350

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