Bennington County, VT Homes

• 

  

  

  /33

  Est $196,127 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft

  476 Tunnel St, Readsboro, VT 05350

  476 Tunnel St, Readsboro, VT 05350
• 

  

  

  /31

  $339,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  This inviting in-town home has been nearly completely renovated with only a few more touches to be brought by the new owner, blending fresh updates with classic comfort. Inside, you’ll find 3 bedrooms and a full bath, plus a bonus room that could serve as a 4th bedroom with a half-bath. An additional room with its own separate entrance is ideal for a small home business. The convenient attached

  Cassie Barbeau Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
• 

  

  

  /33

  $230,000 Sold Sep 30, 2025

  • 1,144 Sq Ft
  • $201/SF
  • 9 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1979

  5 Center St, Bennington, VT 05201

  Welcome to 5 Center Street in the heart of Bennington! This charming single level home offers 3 bedrooms and 1 full bath across a well designed 1,144 sq. ft. floor plan the perfect size for easy living and energy efficiency. Whether you’re looking to downsize, purchase your first home, or simply enjoy the convenience of one floor living, this home is a wonderful fit.Inside, you’ll find a

  Brooke Thomson Drew Mahar McCarthy Real Estate

  5 Center St, Bennington, VT 05201
• 

  

  

  /13

  Est $285,738 Not Listed For Sale

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

  390 Tunnel St, Readsboro, VT 05350

  390 Tunnel St, Readsboro, VT 05350
• 

  

  

  /21

  $105,000

  • Land
  • 0.45 Acre
  • $233,333 per Acre

  236-240 Grandview St, Bennington, VT 05201

  Call your builder! This double lot is ready to build on. Public water, sewer, and electricity are at the street on a town-maintained, paved village residential road. The lot is ideally situated close to essential amenities, including the hospital and a vibrant Main Street boasting diverse shops, restaurants, breweries, and groceries. Enjoy exceptional access to the outdoors with the nearby Green

  Lori Hurley Four Corner Properties LLC

  236-240 Grandview St, Bennington, VT 05201
• 

  

  /51

  $1,900,000 Sold Sep 29, 2025

  • 4,630 Sq Ft
  • $410/SF
  • 46 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1988

  3407 Main St, Manchester, VT 05254

  A rare offering in the heart of Manchester Village, 3407 Main Street is a distinguished Georgian-style estate that exemplifies timeless elegance and refined country living. Set on over three private acres of landscaped grounds, this grand residence is a harmonious blend of classic architectural beauty and modern sophistication. Built in 1988 with meticulous attention to scale and symmetry, the

  Christiane Carroccio TPW Real Estate

  3407 Main St, Manchester, VT 05254
• 

  

  /39

  Est $261,047 Not Listed For Sale

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

  93 Depot St, Readsboro, VT 05350

  93 Depot St, Readsboro, VT 05350
• 

  

  /60

  $5,250,000

  • 9 Beds
  • 10 Baths
  • 7,900 Sq Ft

  1184 E Manchester Rd, Manchester, VT 05255

  Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  1184 E Manchester Rd, Manchester, VT 05255
• 

  

  /41

  $335,000 Sold Sep 29, 2025

  • 1,682 Sq Ft
  • $199/SF
  • 35 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1928

  23 Robinson Ave, Bennington, VT 05201

  Nestled on a quiet street just moments from the golf course, this beautiful two-story brick home offers timeless charm and modern updates. The inviting front porch and lush perennial gardens set the tone for this well-loved property, which also features a fenced-in yard, a small outbuilding, a brand-new shed, and a peaceful backyard water feature. Inside, you'll find 3 bedrooms and 1.5 baths with

  Kelley Mccarthy Mahar McCarthy Real Estate

  23 Robinson Ave, Bennington, VT 05201
• 

  

  /18

  Est $155,354 Not Listed For Sale

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

  78 Canal Dr, Readsboro, VT 05350

  78 Canal Dr, Readsboro, VT 05350
• 

  

  /48

  $3,285,000

  • 5 Beds
  • 6 Baths
  • 6,900 Sq Ft

  68 Green Peak Orchard Rd N, Dorset, VT 05253

  Located in Green Peak Orchard, this custom Greek Revival home on 9.9 aces features wide-planked floors, custom moldings, hand-plastered walls and ceilings, historic reproduction lighting and custom wainscotting & cabinetry. Slate and copper roofs as well as Vermont marble and soapstone complete the authentic details of this striking residence. The home welcomes you through a brick-floored mudroom

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

  68 Green Peak Orchard Rd N, Dorset, VT 05253
• 

  

  /38

  $715,000 Sold Sep 29, 2025

  • 2,120 Sq Ft
  • $337/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  343 Kelleher Rd, Dorset, VT 05251

  This peaceful 3-bedroom Dorset cottage, situated on 1.75 acres, has undergone extensive renovation over the past four years, making it truly move-in ready. Just 2.7 miles to the Dorset Farmers Market and 4.4 miles to the Manchester roundabout, the location is ideal. Recent improvements include a new roof, windows, electrical system, water filtration, backup generator, new bathrooms, fresh

  Christiane Carroccio TPW Real Estate

  343 Kelleher Rd, Dorset, VT 05251
• 

  

  /40

  Est $543,924 Not Listed For Sale

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

  1456 Branch Hill Rd, Readsboro, VT 05350

  1456 Branch Hill Rd, Readsboro, VT 05350
• 

  

  /44

  $365,000

  • 3 Beds
  • 1 Bath
  • 1,660 Sq Ft

  989 Carpenter Hill Rd, Bennington, VT 05201

  Country charm meets modern comfort... Welcome to your perfect slice of paradise! This lovingly updated ranch home is nestled on a peaceful country road and sits on a generous 2.6 acre lot, offering the ideal blend of privacy, space, and style. Step inside to discover a bright, refreshed interior featuring new vinyl plank flooring, freshly painted walls in a neutral palate, and updated lighting

  Angela Bevin Maple Leaf Realty

  989 Carpenter Hill Rd, Bennington, VT 05201
• 

  

  /38

  $595,000 Sold Sep 26, 2025

  • 2,184 Sq Ft
  • $272/SF
  • 71 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  359 Hickory Hill Rd, Bennington, VT 05201

  Welcome to 359 Hickory Hill! Tucked away at the end of a peaceful cul-de-sac on 2.58 acres, this beautifully updated Center Hall Colonial offers privacy, space, and convivence just minutes from downtown Bennington and major highways to New York City, Boston, and beyond.This three bedroom, two and a half bath home is truly turnkey and move in ready. Inside, you'll find gleaming hardwood and

  Brooke Thomson Drew Mahar McCarthy Real Estate

  359 Hickory Hill Rd, Bennington, VT 05201
• 

  

  /40

  Est $382,677 Not Listed For Sale

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

  1693 Branch Hill Rd, Readsboro, VT 05350

  1693 Branch Hill Rd, Readsboro, VT 05350
• 

  

  /27

  $319,000

  • 3 Beds
  • 1 Bath
  • 836 Sq Ft

  557 Beech St, Manchester Center, VT 05255

  Manchester. Let the sun shine in. Easy living on one level with 3 bedrooms. You'll enjoy sitting in the kitchen and gazing either at the mountain view or the flower garden in the backyard. Nice level area to plant a garden or play outdoor games in the yard. Detached 1 car garage, good storage and area for workbench. Quick drive into center of Manchester and minutes to the Manchester Country Club.

  Patti Trudel RE/MAX Four Seasons

  557 Beech St, Manchester Center, VT 05255
• 

  

  /15

  $795,000 Sold Sep 26, 2025

  • 4,972 Sq Ft
  • $160/SF

  • 4 Beds
  • 3.5 Baths
  • Built 1995

  200 Village at Ormsby Hill Rd Unit 4, Manchester, VT 05255

  VILLAGE AT ORMSBY HILL .. beautiful, spacious four bedroom, four and a half bath unit with detached one car garage. ...

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

  200 Village at Ormsby Hill Rd Unit 4, Manchester, VT 05255
• 

  

  /25

  Est $97,255 Not Listed For Sale

  • 1 Bed
  • 586 Sq Ft

  845 Bailey Hill Rd, Readsboro, VT 05350

  845 Bailey Hill Rd, Readsboro, VT 05350
• 

  

  /60

  $465,000

  • 5 Beds
  • 3 Baths
  • 2,622 Sq Ft

  1555 E Arlington Rd, Arlington, VT 05250

  Lovingly renovated by long-term owners, this spacious home beautifully blends small-town charm with modern comfort. Recent updates include a new roof, vinyl siding and windows, brand-new oil and hot water tanks, 200-amp electrical panel, gorgeous kitchen, and more. Featuring 5 bedrooms and 3 full baths in total, the main level offers desirable "one-floor living" with 3 beds, 2 baths, plus a large

  Jenifer Prouty Hoffman Hoffman Real Estate

  1555 E Arlington Rd, Arlington, VT 05250
• 

  

  /32

  $560,000 Sold Sep 26, 2025

  • 1,400 Sq Ft
  • $400/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  35 Glendon Hills Rd, Bondville, VT 05340

  Discover your dream home in Glendon Hills! A truly rare opportunity, this property is the first to become available in this coveted neighborhood in over a decade. Imagine owning a private 1-acre sanctuary with your own picturesque, thriving pond. Inside, experience the joy of cooking in a well-appointed chef's kitchen and the comfort of an open-concept design centered around a charming stacked

  Robin Apps Four Seasons Sotheby's Int'l Realty

  35 Glendon Hills Rd, Bondville, VT 05340
• 

  

  /15

  Est $467,733 Not Listed For Sale

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

  833 Freezing Hole Dr, Readsboro, VT 05350

  833 Freezing Hole Dr, Readsboro, VT 05350
• 

  

  /21

  $120,000

  • Land
  • 20 Acres
  • $6,000 per Acre

  1319 Vail Rd, Bennington, VT 05201

  Discover an exceptional opportunity to build your dream home on this prime 20-acre parcel located in the desirable west end of Bennington. This expansive property offers a perfect blend of privacy and convenience, ready for immediate development.Key features of this remarkable land include an established driveway providing easy access to your future homesite, and a completed perk test

  Lilli West Maple Leaf Realty

  1319 Vail Rd, Bennington, VT 05201
• 

  

  /39

  $2,250,000 Sold Sep 25, 2025

  • 6,471 Sq Ft
  • $348/SF
  • 88 Days On Market

  • 8 Beds
  • 8.5 Baths
  • Built 2009

  69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155

  This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit.The main level of the home features a Gourmet Kitchen, grand

  Sara Buckley Josiah Allen Real Estate, Inc.

  69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155
• 

  

  /40

  Est $423,374 Not Listed For Sale

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

  470 Freezing Hole Dr, Readsboro, VT 05350

  470 Freezing Hole Dr, Readsboro, VT 05350
• 

  

  /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
• 

  

  /41

  $370,000 Sold Sep 25, 2025

  • 1,761 Sq Ft
  • $210/SF
  • 12 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1957

  653 Skyboro Rd E, Pownal, VT 05261

  Pristine and perfect. This 2 bedroom, 3 bath home is situated on 2 acres in Pownal. Offering Eat-in Kitchen, living room with fireplace, primary bedroom with private bath, secondary bedroom with private bath, basement family room and laundry room and more. Outside a wonderful sitting deck and patio, a heated 2 car detached garage with shop space, well landscaped yard with garden space and shed.

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  653 Skyboro Rd E, Pownal, VT 05261
• 

  

  /19

  Est $450,872 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  1858 King Hill Rd, Readsboro, VT 05350

  1858 King Hill Rd, Readsboro, VT 05350
• 

  

  /39

  $289,000

  • 2 Beds
  • 1.5 Baths
  • 1,417 Sq Ft

  51 Russell St Unit D, Arlington, VT 05250

  A Wonderful Townhouse in desirable Arlington Village. Welcome to this charming 2 bedroom 1 and a half bath nestled in the heart of Arlington, with a one car garage. This location offers the perfect blend of comfort and convenience. Inside you will find newly refinished hardwood floors, updated tiling at the entry, and stainless steel appliances. A sun drenched living room and dining area walks

  Robert Sabol Wohler Realty Group

  51 Russell St Unit D, Arlington, VT 05250
• 

  

  /19

  $241,000 Sold Sep 25, 2025

  • 1,070 Sq Ft
  • $225/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1990

  20 Rockwood St, Bennington, VT 05201

  As sweet and tidy as can be, this 3BR/1BA home on a residential street offers one level living just outside of town. Gleaming wood floors in the living room and kitchen; kitchen is efficiently laid out and the dining area opens out to a deck overlooking the landscaped back yard and creates a private retreat for your morning coffee. Full basement has been partially finished with a room perfect

  Vicki Wilson Maple Leaf Realty

  20 Rockwood St, Bennington, VT 05201
• 

  

  /35

  Not Listed For Sale

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

  140 Odonnell Dr, Readsboro, VT 05350

  140 Odonnell Dr, Readsboro, VT 05350
• 

  

  /15

  $269,000

  • 2 Beds
  • 1 Bath
  • 2,500 Sq Ft

  624 Main St, Bennington, VT 05201

  Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

  Kelley Mccarthy Mahar McCarthy Real Estate

  624 Main St, Bennington, VT 05201
• 

  

  /20

  $89,499 Sold Sep 24, 2025

  • 825 Sq Ft
  • $108/SF
  • 120 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2024

  72 Ethans Way, Bennington, VT 05201

  Welcome to 72 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Lewis model manufactured home offers 2 bedrooms, 2 bathroom, and 825 sq. ft. (16 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  72 Ethans Way, Bennington, VT 05201
• 

  

  /20

  Est $371,874 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  603 Wiley Mountain Dr, Readsboro, VT 05350

  603 Wiley Mountain Dr, Readsboro, VT 05350
• 

  

  /43

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  683 Water St, North Bennington, VT 05257

  Completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
• 

  

  /47

  $240,000 Sold Sep 24, 2025

  • 2,404 Sq Ft
  • $100/SF
  • 114 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1895

  120 Imperial Ave, Bennington, VT 05201

  Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

  Kelley Mccarthy Mahar McCarthy Real Estate

  120 Imperial Ave, Bennington, VT 05201
• 

  

  /24

  Est $374,098 Not Listed For Sale

  • 4 Beds

  1680 W Hill Dr, Readsboro, VT 05350

  1680 W Hill Dr, Readsboro, VT 05350
• 

  

  /51

  $269,000

  • 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
• 

  

  /4

  $96,906 Sold Sep 24, 2025

  • 777 Sq Ft
  • $125/SF
  • 26 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2025

  29 Dustin Dr, Bennington, VT 05201

  Welcome to 29 Dustin Drive, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  29 Dustin Dr, Bennington, VT 05201
• 

  

  /58

  Est $316,706 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  1806 Bosley Hill Rd, Readsboro, VT 05350

  1806 Bosley Hill Rd, Readsboro, VT 05350

Showing Results 361 - 400, Page 10 of 18