Bennington County, VT Homes

• 

  

  

  /14

  $2,500,000

  • Land
  • 227 Acres
  • $11,013 per Acre

  00 Vermont 11, Peru, VT 05152

  Bordering Green Mountain National Forest with sweeping views of Stratton, Bromley, and Magic Mountains, this 227 +/- acre offering in Peru, Vermont captures the scale, privacy, and natural beauty that define Southern Vermont mountain living.Spanning two distinct parcels, the offering includes 199 +/- acres bordering National Forest land and a separate 28 +/- acre parcel positioned to capture

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
• 

  

  

  /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 Real Estate

  0 Oberhugel Rd Unit 5059139, Stamford, VT 05352
• 

  

  

  /26

  Est $731,227

  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

  • 4 Days On Market
• 

  

  

  /40

  $419,000

  $60K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,861 Sq Ft

  120 Village St, East Dorset, VT 05253

  Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

  Dana Kingsley Josiah Allen Real Estate, Inc.

  120 Village St, East Dorset, VT 05253
• 

  

  

  /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 $673,317

  Last Listing Agent Faith Rhodes Maple Leaf Real Estate

  697 Hamilton Hollow Rd, Arlington, VT 05250
• 

  

  /32

  Est $607,294

  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

  • 18 Days On Market
• 

  

  /35

  $799,000

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,078 Sq Ft

  63 Raspberry Hill Rd, Winhall, VT 05340

  Spacious and light-filled four-bedroom home ideally located in desirable Strattonwald, offering both winter and summer enjoyment in a private, peaceful setting. Enjoy convenient access to the Stratton winter shuttle, as well as summer amenities including a private pond and tennis courts. The home features generous living spaces perfect for gathering and entertaining, including a cozy fireplace

  Carrie Mathews Winhall Real Estate

  63 Raspberry Hill Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /32

  Est $666,743

  Not Listed For Sale

  409 Bromley Brook Rd, Manchester Center, VT 05255

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

  409 Bromley Brook Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 12 Days On Market
• 

  

  /18

  $79,000

  $30K PRICE DROP

  • Land
  • 17 Acres
  • $4,647 per Acre

  00 Bill T Dr, Readsboro, VT 05350

  Significant price reduction! This gently sloping 17-acre parcel should not be overlooked. This property offers a dead-end location on a town-maintained road, providing you with privacy and convenience. Nestled in the charming town of Readsboro and surrounded by the beautiful Green Mountains, you will have easy access to VAST snowmobile trails and VASA ATV trails. Plus, you are just a stone's

  Michelle O'Neil Deerfield Valley Real Estate

  00 Bill T Dr, Readsboro, VT 05350
• 

  

  /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 $196,104

  Last Listing Agent Matt Waddington Hoffman Real Estate

  305 Weeks St, Bennington, VT 05201
• 

  

  /36

  Est $602,900

  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

  • 5 Days On Market
• 

  

  /12

  $1,295,000

  • Land
  • 52 Acres
  • $24,904 per Acre

  0 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  0 Montgomery Rd, Pownal, VT 05261
• 

  

  /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
• 

  

  /26

  Est $587,190

  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

  • 15 Days On Market
• 

  

  /4

  $350,000

  New Construction Pending

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

  526 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 Real Estate

  526 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /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
• 

  

  /23

  Est $536,770

  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

  • 4 Days On Market
• 

  

  /10

  $125,000

  • Land
  • 5.77 Acres
  • $21,664 per Acre

  0 East Rd, Shaftsbury, VT 05262

  Set along scenic East Road in Shaftsbury, this 5.77-acre wooded parcel offers a beautiful opportunity to create a private Vermont homesite in one of the area’s most appealing rural settings. The land is currently wooded, allowing the next owner to decide how much to clear for a driveway, yard, gardens, or building site, with potential for a mountain view to the north with selective clearing.

  Jenifer Prouty Hoffman Hoffman Real Estate

  0 East Rd, Shaftsbury, VT 05262
• 

  

  /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 $295,111

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  121 Fillmore St, Bennington, VT 05201
• 

  

  /35

  Est $807,961

  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

  • 9 Days On Market
• 

  

  /21

  $549,000

  • 2 Beds
  • 2.5 Baths
  • 1,596 Sq Ft

  43 Murray Hill Heights Rd Unit 37, Manchester, VT 05255

  CENTRAL A/C, GARAGE! VIEWS! Beautiful in-town condominium offering exceptional custom upgrades and distinctive craftsmanship throughout. This thoughtfully designed home features central air conditioning, mahogany-encased sliding glass doors and windows, stunning mahogany staircases, and rich wood flooring throughout the main living area and loft. Enhanced insulation provides superior comfort,

  Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  43 Murray Hill Heights Rd Unit 37, Manchester, VT 05255
• 

  

  /33

  $685,000

  Sold Apr 16, 2026

  158 Upland Downs Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft
  • Built 1983

  Last Sold Summary

  • 16% Below List Price
  • $393/SF
  • 147 Days On Market

  Current Estimated Value $689,346

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

  158 Upland Downs Rd, Manchester Center, VT 05255
• 

  

  /21

  Est $495,699

  Not Listed For Sale

  172 Carlen St, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1984

  172 Carlen St, Manchester Center, VT 05255

  Last Sold Summary

  • 21 Days On Market
• 

  

  /49

  $650,000

  • 5 Beds
  • 3 Baths
  • 5,524 Sq Ft

  81 Honeysuckle Ln, North Bennington, VT 05257

  Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space

  Kelley Mccarthy Mahar McCarthy Real Estate

  81 Honeysuckle Ln, North Bennington, VT 05257
• 

  

  /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
• 

  

  /41

  Est $579,400

  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

  • 5 Days On Market
• 

  

  /46

  $195,000

  $30K PRICE DROP Pending

  • 5 Beds
  • 2 Baths
  • 2,212 Sq Ft

  1138 Main Rd, Stamford, VT 05352

  Stamford, VT - A country drive less than 10 minutes North Adams, MA- home of Mass MoCA. Dating back to 1850 this spacious home boasts 4 bedrooms & 2 baths. 1st floor bedroom, bath, laundry, kitchen, dining, living room, den & sunroom. Nestled on almost and acre of land and bordering a babbling brook this property offers a privacy sanctuary. Come take a look for yourself! Located close to museums

  Colleen Zajac MONARCH REALTY, INC.

  1138 Main Rd, Stamford, VT 05352
• 

  

  /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 $941,049

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

  2844 Main St, Manchester, VT 05254
• 

  

  /11

  Est $621,027

  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

  • 41 Days On Market
• 

  

  /52

  $850,000

  $120K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 5,764 Sq Ft

  24 Vt Route 11, Londonderry, VT 05148

  Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection. Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chef’s kitchen, sun-filled all-season

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  24 Vt Route 11, Londonderry, VT 05148
• 

  

  /23

  $259,000

  Sold Jun 04, 2026

  214 Hickory Rd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 816 Sq Ft
  • Built 1960

  Last Sold Summary

  • $317/SF
  • 2 Days On Market

  Current Estimated Value $231,145

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  214 Hickory Rd, Bennington, VT 05201
• 

  

  /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

  • 5 Days On Market
• 

  

  /37

  $584,900

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14 Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

  Julie Citron RE/MAX Four Seasons

  14 Marisa Ln, Dorset, VT 05251
• 

  /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 $206,029

  Last Listing Agent Cheyanne Pugliese

  24 Stratton Rd W, Winhall, VT 05340
• 

  

  /32

  Est $1,000,117

  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

  • 109 Days On Market
• 

  

  /26

  $479,000

  $70K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  67 Valley Pass, Manchester, VT 05255

  Welcome to 67 Valley Pass Road, where your new Vermont home awaits. This stylish split-level ranch has been meticulously maintained and is truly move in ready. The home features four bedrooms, highlighted by a spacious primary bedroom with an en suite bathroom.The upper level offers an updated open kitchen and dining area with an easy flowing layout. Just off the dining space is a cozy living

  Sara Buckley Josiah Allen Real Estate, Inc.

  67 Valley Pass, Manchester, VT 05255
• 

  

  /47

  $918,000

  Sold Apr 07, 2026

  255 Hemlock Ridge Rd, Manchester Center, VT 05255

  • 3 Beds
  • 3 Baths
  • 4,000 Sq Ft
  • Built 1996

  Last Sold Summary

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

  Current Estimated Value $902,398

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

  255 Hemlock Ridge Rd, Manchester Center, VT 05255
• 

  

  /31

  Est $520,841

  Not Listed For Sale

  109 Hillcrest Rd, Manchester Center, VT 05255

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1969

  109 Hillcrest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 10 Days On Market
• 

  

  /32

  $449,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  32 Aspen Ln, Winhall, VT 05340

  A Sanctuary for Every Season:Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you’re here to chase the morning light on the slopes of nearby Stratton Resort or to spend a

  Robin Apps Four Seasons Sotheby's Int'l Realty

  32 Aspen Ln, Winhall, VT 05340

Showing Results 561 - 600, Page 15 of 18