Bennington County, VT Homes

• 

  

  

  /21

  $210,000

  Under Contract

  • Land
  • 4.51 Acres
  • $46,563 per Acre

  2740 Sandgate Rd, Arlington, VT 05250

  Set on 4.51 picturesque acres with an impressive 932 feet of frontage along the coveted Green River, this exceptional property is truly a fisherman's dream and a nature lover's paradise. Open meadows, mature trees, and beautifully maintained grounds create a peaceful setting that showcases the best of Vermont's natural beauty. A winding wooded walking path invites you to explore the landscape

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  2740 Sandgate Rd, Arlington, VT 05250
• 

  

  

  /45

  $405,000

  Sold Apr 20, 2026

  848 Coleville Rd, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $200/SF
  • 151 Days On Market

  Current Estimated Value $420,047

  Last Listing Agent Beatrice O'Connell Maple Leaf Real Estate

  848 Coleville Rd, Bennington, VT 05201
• 

  

  

  /38

  Est $394,575

  Not Listed For Sale

  218 Puddingstone Rd, Pownal, VT 05261

  • 3 Beds
  • 1.5 Baths
  • 1,936 Sq Ft
  • Built 1971

  218 Puddingstone Rd, Pownal, VT 05261

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  

  /32

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,878 Sq Ft

  32 Benson Fuller Dr, Bondville, VT 05340

  Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lot along a quiet road, this move-in-ready sanctuary offers effortless mountain comfort, high-end entertaining space, and practical updates throughout. Quality architectural details welcome you into a bright main level boasting a

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  32 Benson Fuller Dr, Bondville, VT 05340
• 

  

  

  /35

  $220,000

  Sold Sep 16, 2025

  115 Jefferson Ave, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft
  • Built 1930

  Last Sold Summary

  • 18% Below List Price
  • $142/SF
  • 83 Days On Market

  Current Estimated Value $233,375

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  115 Jefferson Ave, Bennington, VT 05201
• 

  

  /16

  Est $152,155

  Not Listed For Sale

  86 Floyds Way, Pownal, VT 05261

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1972

  86 Floyds Way, Pownal, VT 05261

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Jeffrey Dorman
• 

  

  /8

  $199,000

  $51K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  924 Vt Route 7a, Shaftsbury, VT 05262

  Full of character and opportunity, this charming 2-bedroom, 2-bath home in Shaftsbury offers an affordable entry into homeownership or a fantastic addition to an investment portfolio. Once serving as the local post office, the property has a unique history and a cozy footprint that makes it ideal as a starter home, downsizing option, or rental property. Recent improvements include a beautifully

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  924 Vt Route 7a, Shaftsbury, VT 05262
• 

  

  /59

  $1,082,500

  Sold Aug 29, 2025

  4 Garden Loop Rd, Winhall, VT 05340

  • 3 Beds
  • 3.5 Baths
  • 4,054 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Below List Price
  • $267/SF
  • 45 Days On Market

  Current Estimated Value $1,144,000

  Last Listing Agent Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

  4 Garden Loop Rd, Winhall, VT 05340
• 

  

  /40

  Est $806,234

  Not Listed For Sale

  718 Montgomery Rd, Pownal, VT 05261

  • 5 Beds
  • 4 Baths
  • 3,879 Sq Ft
  • Built 1800

  718 Montgomery Rd, Pownal, VT 05261

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty
• 

  

  /60

  $989,900

  • 4 Beds
  • 3 Baths
  • 5,697 Sq Ft

  66 Somerset Rd, Searsburg, VT 05363

  Six oversized garage bays across two multi-level outbuildings, direct access to Green Mountain National Forest, backyard waterfalls, and 5.4 private acres make this gated Southern Vermont retreat unlike anything else near Wilmington. Just five miles from downtown Wilmington and less than 12 miles from Mount Snow, the property combines substantial space for living and entertaining with exceptional

  Erica Reynolds Southern Vermont Realty Group

  66 Somerset Rd, Searsburg, VT 05363
• 

  

  /22

  $210,000

  Sold Jan 21, 2026

  52 Walker Meadow, Arlington, VT 05250

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1964

  Last Sold Summary

  • 9% Below List Price
  • $109/SF
  • 4 Days On Market

  Current Estimated Value $220,409

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

  52 Walker Meadow, Arlington, VT 05250
• 

  

  /19

  Est $247,263

  Not Listed For Sale

  169 Montgomery Rd, Pownal, VT 05261

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

  169 Montgomery Rd, Pownal, VT 05261

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Corey Bishop BISHOP WEST REAL ESTATE
• 

  

  /4

  $1,295,000

  • Land
  • 52.61 Acres
  • $24,615 per Acre

  00 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

  00 Montgomery Rd, Pownal, VT 05261
• 

  

  /10

  $18,500

  Sold Jan 09, 2026

  lot139&140 Bergrucken Ln, Readsboro, VT 05350

  • Land
  • 2.3 Acres
  • $8,043 per Acre

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Christine Girard Lamacchia Realty, Inc. - North Adams

  lot139&140 Bergrucken Ln, Readsboro, VT 05350
• 

  

  /59

  Est $244,173

  Not Listed For Sale

  663 Sweet Rd, Pownal, VT 05261

  • 2 Beds
  • 2 Baths
  • 3,024 Sq Ft
  • Built 2010

  663 Sweet Rd, Pownal, VT 05261

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Floyd Amidon Maple Leaf Real Estate
• 

  

  /28

  $120,500

  Pending

  • 4 Beds
  • 1 Bath
  • 1,368 Sq Ft

  113 Forgette Rd, Stamford, VT 05352

  Roll up your sleeves! This property needs complete rehab but will be well worth the effort. Private location set back from the road, large yard ready to enjoy. Short drive to North Adams for shopping. Don't hesitate to take a look this may be the one for you.

  Andrea Thackston R.H. Thackston & Company/Bellows Falls

  113 Forgette Rd, Stamford, VT 05352
• 

  

  /26

  $160,000

  Sold Jun 30, 2026

  00 Finbar's Forest Rd, Manchester, VT 05255

  • Land
  • 3.1 Acres
  • $51,613 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 17 Days On Market

  Last Listing Agent Patti Trudel RE/MAX Four Seasons

  00 Finbar's Forest Rd, Manchester, VT 05255
• 

  

  /52

  Est $260,884

  Not Listed For Sale

  351 Old Military Rd, Pownal, VT 05261

  • 4 Beds
  • 1 Bath
  • 1,378 Sq Ft
  • Built 1969

  351 Old Military Rd, Pownal, VT 05261

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Floyd Amidon Maple Leaf Real Estate
• 

  

  /42

  $180,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  105 Hicks Ave, Bennington, VT 05201

  Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn

  Angela Bevin Maple Leaf Real Estate

  105 Hicks Ave, Bennington, VT 05201
• 

  

  /60

  $245,000

  Sold Sep 22, 2025

  19 Robinson Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1954

  Last Sold Summary

  • 11% Below List Price
  • $186/SF
  • 3 Days On Market

  Current Estimated Value $261,243

  Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  19 Robinson Ave, Bennington, VT 05201
• 

  

  /40

  Est $368,562

  Not Listed For Sale

  505 Cross Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 2003

  505 Cross Rd, Bennington, VT 05201

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate
• 

  

  /16

  $520,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,847 Sq Ft

  36A Marisa Ln, Dorset, VT 05251

  Enjoy the ease of single-level living in this well-appointed three-bedroom condominium tucked away on Marissa Lane. Set back from the road in a quiet location, this home offers comfort, convenience, and a peaceful setting just minutes from the Dorset Green and all the shopping, dining, and recreational amenities of Manchester.Warm wood floors flow throughout the main living areas, while the

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  36A Marisa Ln, Dorset, VT 05251
• 

  

  /12

  $325,000

  Sold Jul 20, 2026

  343 Safford St, Bennington, VT 05201

  • 2,476 Sq Ft
  • Built 1900

  Last Sold Summary

  • $131/SF
  • 34 Days On Market

  Last Listing Agent Lori Hurley Four Corner Properties LLC

  343 Safford St, Bennington, VT 05201
• 

  

  /40

  Est $602,316

  Not Listed For Sale

  260 Tower Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 3,976 Sq Ft
  • Built 1981

  260 Tower Rd, Bennington, VT 05201

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent Allison Pacelli Pacelli Zepka Corporation
• 

  

  /60

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,295 Sq Ft

  142 Schenkar Rd, Pownal, VT 05261

  Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

  Erin McCormick KW Vermont

  142 Schenkar Rd, Pownal, VT 05261
• 

  

  /23

  $388,800

  Sold Jun 10, 2026

  317 Chester Knoll Dr, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2026

  Last Sold Summary

  • $240/SF

  Last Listing Agent Lilli West Maple Leaf Real Estate

  317 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /24

  Est $162,253

  Not Listed For Sale

  354 NW Hill Rd, Pownal, VT 05261

  • 1 Bed
  • 816 Sq Ft
  • Built 1900

  354 NW Hill Rd, Pownal, VT 05261

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Nicholas Charest Maple Leaf Real Estate
• 

  

  /60

  $574,900

  $5K PRICE DROP

  • 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
• 

  

  /50

  $4,150,000

  Sold Mar 18, 2026

  318 Spring Hill Ln, Dorset, VT 05251

  • 7 Beds
  • 10 Baths
  • 7,422 Sq Ft
  • Built 1941

  Last Sold Summary

  • 15% Below List Price
  • $559/SF
  • 181 Days On Market

  Current Estimated Value $4,209,873

  Last Listing Agent Richard Slocum Four Seasons Sotheby's Int'l Realty

  318 Spring Hill Ln, Dorset, VT 05251
• 

  

  /27

  Est $314,476

  Not Listed For Sale

  46 NW Hill Rd, Pownal, VT 05261

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft
  • Built 1900

  46 NW Hill Rd, Pownal, VT 05261

  Last Sold Summary

  • 193 Days On Market

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate
• 

  

  /27

  $645,000

  $30K PRICE DROP

  • 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
• 

  

  /33

  $740,000

  Sold Jan 02, 2026

  G12 Cobble Ridge Rd, Winhall, VT 05340

  • 4 Beds
  • 4 Baths
  • 2,764 Sq Ft
  • Built 1985

  Last Sold Summary

  • 5% Below List Price
  • $268/SF
  • 1 Day On Market

  Current Estimated Value $769,000

  Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

  G12 Cobble Ridge Rd, Winhall, VT 05340
• 

  

  /40

  Est $444,008

  Not Listed For Sale

  42 Maple Grove Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft
  • Built 1960

  42 Maple Grove Rd, Bennington, VT 05201

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate
• 

  

  /4

  $349,000

  • 3,637 Sq Ft

  710 Main St, Bennington, VT 05201

  Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental history and

  Dan Mason Perrott Realty

  710 Main St, Bennington, VT 05201
• 

  

  /59

  $408,000

  Sold Jul 27, 2026

  131 Pine Cir, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,119 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $193/SF
  • 48 Days On Market

  Current Estimated Value $421,104

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  131 Pine Cir, Bennington, VT 05201
• 

  

  /34

  Est $295,563

  Not Listed For Sale

  543 Middle Pownal Rd, Pownal, VT 05261

  • 3 Beds
  • 1 Bath
  • 1,288 Sq Ft
  • Built 1973

  543 Middle Pownal Rd, Pownal, VT 05261

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Lilli West Maple Leaf Real Estate
• 

  

  /52

  $179,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
• 

  

  /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 $391,752

  Last Listing Agent Lori Hurley Four Corner Properties LLC

  38 Spruce Ln, Arlington, VT 05250
• 

  

  /24

  Est $379,151

  Not Listed For Sale

  78 Middle Pownal Rd, Pownal, VT 05261

  • 3 Beds
  • 1.5 Baths
  • 1,624 Sq Ft
  • Built 1922

  78 Middle Pownal Rd, Pownal, VT 05261

  Last Sold Summary

  • 50 Days On Market

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

  

  /60

  $1,850,000

  • 4 Beds
  • 3.5 Baths
  • 3,828 Sq Ft

  400 Spring Brook Rd, Arlington, VT 05250

  A once-in-a-generation estate, this 125 acre property offers the rare combination that you almost never find: true privacy, two residences, forest trails, cultivated grounds, and river frontage on the Battenkill. Nestled at the base of Red Mountain on a private road, with the far shore protected by parkland, the property feels like its own secluded world while remaining minutes from Manchester

  Emily Heyer Hoffman Real Estate

  400 Spring Brook Rd, Arlington, VT 05250

Showing Results 441 - 480, Page 12 of 18