Bennington County, VT Homes

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  /54

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  58 Mount Anthony Rd, Bennington, VT 05201

  Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

  Monique Geannelis Mahar McCarthy Real Estate

  58 Mount Anthony Rd, Bennington, VT 05201
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  /59

  $210,000 Sold Nov 03, 2025

  • 1,815 Sq Ft
  • $116/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  890 Vt Route 7a, Shaftsbury, VT 05262

  This 3-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and convenience. Set on a generous .35-acre lot, the property features a large living room ideal for gatherings, and a spacious kitchen with plenty of room for cooking and entertaining. Enjoy the convenience of a large detached garage, plus a private outdoor space that's perfect for gardening, playing, or relaxing

  Floyd Amidon Maple Leaf Realty

  890 Vt Route 7a, Shaftsbury, VT 05262
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  /35

  Est $397,000 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  15 Stratton View Rd, Bondville, VT 05340

  15 Stratton View Rd, Bondville, VT 05340
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  /30

  $629,000

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  115 Nottingham Park, Manchester Center, VT 05255

  This spacious raised ranch sits on 1.08 acres and offers seasonal western mountain views, with close proximity to both Bromley and Stratton.The home features a large, open-concept floor plan on the main level, including a living room and a combined dining/kitchen area with a cathedral ceiling and a wood-burning stove on a raised brick hearth. This floor also has three bedrooms and one full

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  115 Nottingham Park, Manchester Center, VT 05255
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  /44

  $40,000 Sold Oct 31, 2025

  • 1,952 Sq Ft
  • $20/SF
  • 108 Days On Market

  • 5 Beds
  • 1 Bath
  • Built 1910

  273 Union St, Bennington, VT 05201

  This village property has great bones and potential!! First floor includes generously sized kitchen, formal dining room and living room as well as a small office offering the opportunity to expand the full bath to include laundry. The second floor includes four bedrooms including a primary that has a sitting area/dressing room/nursery, whatever suits your needs. Separate barn that while

  Catherine Cairns Maple Leaf Realty

  273 Union St, Bennington, VT 05201
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  /11

  Est $567,651 Not Listed For Sale

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

  1238 North Rd, East Arlington, VT 05252

  1238 North Rd, East Arlington, VT 05252
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  /40

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft

  134 Monument Ave, Bennington, VT 05201

  Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary

  Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
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  /38

  $779,000 Sold Oct 31, 2025

  • 2,997 Sq Ft
  • $260/SF
  • 22 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1996

  44 Hilltop Rd, Winhall, VT 05340

  Four bedroom, four bathroom Intervale townhouse has all the space you need in a Stratton home. This is the largest Intervale floor plan, with a second living room and wet bar on the lower, walk out floor. The main floor has a mud room entry, living room with wood burning fireplace, and dining room open to kitchen. The primary suite is on the main floor, secondary suite is upstairs, and an

  Christiane Carroccio TPW Real Estate

  44 Hilltop Rd, Winhall, VT 05340
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  /19

  Est $373,908 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  367 Shady Pines, Arlington, VT 05250

  367 Shady Pines, Arlington, VT 05250
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  /55

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  935 Old Manchester Rd, Peru, VT 05152

  Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

  Margretta Fischer Wohler Realty Group

  935 Old Manchester Rd, Peru, VT 05152
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  /44

  $575,000 Sold Oct 31, 2025

  • 2,212 Sq Ft
  • $260/SF
  • 2 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1972

  1044 Berwall Rd, Arlington, VT 05250

  Mountain Views! Encompassing mountain views. Take in the natural surroundings while relaxing on expansive wrap around deck. Beautifully updated four bedroom, three bath home set on 3.70 Acres. The light filled main level features open kitchen, dining and living. The heated sunroom with a wall of new windows just enhances the views. Your choice of three main level bedrooms and two full baths. Or

  Margretta Fischer Wohler Realty Group

  1044 Berwall Rd, Arlington, VT 05250
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  /14

  Est $445,961 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  535 Dunlap Farm Rd, Arlington, VT 05250

  535 Dunlap Farm Rd, Arlington, VT 05250
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  /20

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  27 Owls Head Hill Ln, Dorset, VT 05251

  Charming Raised Ranch on 2 Acres – Dorset, VTWelcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space.3 Bedrooms | 2 Full Baths | 2-Car Attached GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  27 Owls Head Hill Ln, Dorset, VT 05251
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  /33

  $150,000 Sold Oct 31, 2025

  • 1,104 Sq Ft
  • $136/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1880

  229 Division St, Bennington, VT 05201

  Welcome to this charming 1900's cottage, ideally situated in the heart of Bennington Village! This delightful home offers the perfect blend of historic charm and modern convenience, though it is well-loved and awaits your personal touch and some TLC to truly shine. Enjoy easy access to local shopping and schools, making daily errands and commutes a breeze. For outdoor enthusiasts, nearby trails

  Lilli West Maple Leaf Realty

  229 Division St, Bennington, VT 05201
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  /40

  Est $103,004 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 540 Sq Ft

  51 Chiselville Rd, Arlington, VT 05250

  51 Chiselville Rd, Arlington, VT 05250
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  /39

  $599,000

  • 5 Beds
  • 3.5 Baths
  • 2,468 Sq Ft

  17 Signal Hill Rd, Winhall, VT 05340

  17 Signal Hill Road offers Vermont charm in a secluded mountain setting. With over 2,400 square feet of living space, this five-bedroom, three-and-a-half-bath home has been thoughtfully maintained and move-in ready. The main level features a spacious living room with a dramatic fieldstone fireplace, vaulted ceilings, and skylights that fill the home with natural light. A loft overlooking

  Christiane Carroccio TPW Real Estate

  17 Signal Hill Rd, Winhall, VT 05340
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  /14

  $20,000 Sold Oct 30, 2025

  • 561 Sq Ft
  • $36/SF
  • 0 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1950

  79 Skytop Dr Unit 6, Bennington, VT 05201

  End unit condo in the Skytop Condominium Association. Needs total rehab, including structural repairs; might be best to teardown and rebuild. Power is on, but water and heat are shut off. Recently connected to town water. There are 8 units in the association that share 3 acres of common land and a paved road. Would make a great long term rental/investment property!

  Jenifer Prouty Hoffman Hoffman Real Estate

  79 Skytop Dr Unit 6, Bennington, VT 05201
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  /18

  Est $583,326 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft

  55 Wildflower Ln, Arlington, VT 05250

  55 Wildflower Ln, Arlington, VT 05250
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  /30

  $550,000

  • 2 Beds
  • 2 Baths
  • 2,218 Sq Ft

  1439 Main St, Manchester Center, VT 05255

  Purdy School House, est. 1850 - Step into history with this lovingly preserved former schoolhouse, offering timeless character with modern comfort. Featuring 2 bedrooms, 2 baths, and a striking stone fireplace, this home blends warmth and charm. A full basement and attached one-car garage provide practical convenience. Set on 2.01 acres, the property includes a fenced dog yard and plenty of space

  Richard Slocum Four Seasons Sotheby's Int'l Realty

  1439 Main St, Manchester Center, VT 05255
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  /51

  $205,000 Sold Oct 30, 2025

  • 2,735 Sq Ft
  • $75/SF
  • 134 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1811

  30 River Rd, Arlington, VT 05250

  300 feet of Batthenkill River front this 3 bedroom 2 bath Colonial with a 2 bed 1 bath in-law wing with an idyllic sound of the River. Enjoy the custom built fire pit to the sound of the river in the evenings and kayaking by day. The 1.5 acre lot has plenty room for gardening or just to spread out a bit. Come see what Southern VT Battenkill River has to offer.

  Dan Mason Perrott Realty

  30 River Rd, Arlington, VT 05250
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  /37

  Est $444,198 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,718 Sq Ft

  127 Flynn Hollow Rd, Sunderland, VT 05250

  127 Flynn Hollow Rd, Sunderland, VT 05250
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  /27

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,958 Sq Ft

  550 Finbars Forest Rd, Manchester Center, VT 05255

  Tucked away on a private two-acre lot in the heart of the Green Mountains and within the Burr & Burton Academy school district, this modern farmhouse offers a peaceful setting minutes from downtown Manchester and adjacent to Manchester Country Club. The main level features an open-concept layout with a beautifully designed kitchen at its center - rich dark cabinetry, Caesarstone quartz

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  550 Finbars Forest Rd, Manchester Center, VT 05255
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  /27

  $218,000 Sold Oct 30, 2025

  • 1,959 Sq Ft
  • $111/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  198 Twitchell Hill Rd, Shaftsbury, VT 05262

  Discover the potential in this spacious 3-bedroom home, nestled in a beautiful setting with room to make it your own. Offering a flexible floor plan, the home includes two primary bedrooms that share a full bathroom, plus an additional guest bedroom and bath, making it ideal for multi-generational living or visiting guests. Inside, you’ll find a sunken living room that adds character and charm,

  Faith Rhodes Maple Leaf Realty

  198 Twitchell Hill Rd, Shaftsbury, VT 05262
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  /34

  Est $213,460 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  925 South Rd, East Arlington, VT 05252

  925 South Rd, East Arlington, VT 05252
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  /44

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  475 Sunrise Ln, Arlington, VT 05250

  Discover your private retreat on Beautiful Sunrise Lane! Welcome to "Pine Hollow". This comfortable and inviting home sits on over 6 acres of serene, peaceful landscape, for those seeking a quiet environment and space! Idyllic setting surrounded by pines with complete solitude at the end of a private rd. Enjoy the comfort of generous rooms filled with natural light, ideal for family living and

  Sunny Breen Josiah Allen Real Estate, Inc.

  475 Sunrise Ln, Arlington, VT 05250
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  /37

  $625,000 Sold Oct 29, 2025

  • 2,355 Sq Ft
  • $265/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1991

  790 Maple Hill Rd, Arlington, VT 05250

  Experience the perfect Vermont country home - whether as a peaceful retreat or full-time residence - nestled on 13 private acres of open fields and woods with breathtaking mountain views. Thoughtfully updated, this inviting property features a brand-new modern kitchen with quartz countertops, a Bosch refrigerator and dishwasher, a Cafe induction stove, and a new chimney, blending elegance with

  Andy Reed Four Seasons Sotheby's Int'l Realty

  790 Maple Hill Rd, Arlington, VT 05250
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  /25

  Est $420,806 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,593 Sq Ft

  125 Chiselville Rd, Arlington, VT 05250

  125 Chiselville Rd, Arlington, VT 05250
• 

  

  /40

  $549,000

  • 2 Beds
  • 2 Baths
  • 4,044 Sq Ft

  5515 Main St, Manchester, VT 05255

  Own a piece of Vermont history with this charming 1830s home, perfectly situated on Main Street in downtown. Zoned for mixed use (MU2), this versatile property offers endless possibilities-live, work, or do both in one inspiring space. The 2-bedroom, 2-bath home blends vintage Vermont character with modern comfort, featuring mini-splits for heating and cooling, a propane stove, fiber optic

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  5515 Main St, Manchester, VT 05255
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  /43

  $451,500 Sold Oct 28, 2025

  • 2,374 Sq Ft
  • $190/SF
  • 28 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1981

  464 Forest Mountain Rd, Peru, VT 05152

  Tucked within a serene wooded community, this home enjoys an intimate setting alongside a mountain brook. Outdoor adventure is at your doorstep - ski at Bromley, Stratton, or Magic, explore Wild Wings cross-country center, or wander countless hiking trails. An association trail just across from the driveway meanders alongside the brook for instant nature mindfullness time. Inside, warm knotty

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  464 Forest Mountain Rd, Peru, VT 05152
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  /32

  Est $464,452 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  2128 North Rd, Arlington, VT 05250

  2128 North Rd, Arlington, VT 05250
• 

  

  /53

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,894 Sq Ft

  190 Vt Route 11 Unit 1, Peru, VT 05152

  Don't miss the opportunity to own this renovated 4 bedroom/ 2 full bath townhouse in Peru, VT. This tasteful and high end renovation will wow you. Combining the ambiance and character of a European mountain Chalet with the amenities and style of a contemporary mountain residence, this offers beautiful tiled luxury bathrooms and gourmet kitchen. The great room has vaulted wood beamed ceilings,

  Robert Sabol Wohler Realty Group

  190 Vt Route 11 Unit 1, Peru, VT 05152
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  /28

  $815,000 Sold Oct 28, 2025

  • 1,908 Sq Ft
  • $427/SF
  • 93 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1971

  6 Roundtree Rd, Winhall, VT 05340

  Prime Stratton location! This charming 4-bedroom, 2-bathroom retreat offers vaulted ceilings, an open-concept living area with a wood burning fireplace, and a private deck and backyard for relaxing after a day on the slopes. With weekend and holiday shuttle service during ski season, plus easy access to Stratton Village’s shops, dining, and year-round activities, it’s the ideal spot to recharge

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  6 Roundtree Rd, Winhall, VT 05340
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  /38

  Est $308,641 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,268 Sq Ft

  1469 Sunderland Hill Rd, Arlington, VT 05250

  1469 Sunderland Hill Rd, Arlington, VT 05250
• 

  

  /34

  $565,000

  • 4 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  22 Bromley Forest Rd, Bondville, VT 05340

  Welcome to your ideal Vermont retreat where comfort, style, and location converge! This upgraded 4-bedroom home, complete with a versatile bonus room, has been meticulously maintained and offers an open floor plan perfect for gathering and everyday living. The kitchen shines with stainless steel appliances and a new professional grade dual-fuel convection range. East and south facing windows

  Carrie Mathews Winhall Real Estate

  22 Bromley Forest Rd, Bondville, VT 05340
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  /30

  $361,500 Sold Oct 27, 2025

  • 2,162 Sq Ft
  • $167/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2007

  64 Bergblume Cir, Stamford, VT 05352

  Priced to Sell - Includes Additional Building Lot!This charming 3-bedroom, 3-bath home built in 2007 offers peace, privacy, and natural surroundings. Included in the sale is a second adjoining building lot, adding value and future potential.This home is perfect for those seeking a four-season retreat. The home features abundant natural light through oversized vinyl windows and a cozy wood-burning

  Pam Tworig BISHOP WEST REAL ESTATE

  64 Bergblume Cir, Stamford, VT 05352
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  /29

  Est $513,035 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  2353 North Rd, Arlington, VT 05250

  2353 North Rd, Arlington, VT 05250
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  /33

  $775,000

  • 4 Beds
  • 3 Baths
  • 2,317 Sq Ft

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

  Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s

  Carrie Mathews Winhall Real Estate

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
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  /46

  $645,000 Sold Oct 27, 2025

  • 1,945 Sq Ft
  • $332/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  197 N Ridge Run, Manchester Center, VT 05255

  Set on 1.2 acres, this pristine home feels like it’s straight from the pages of a picture book. Perched atop a gentle rise near the end of a quiet cul-de-sac, it offers privacy, seasonal winter views, and a peaceful setting just one mile from downtown Manchester. From the attached garage, enter through a well-appointed mudroom into the kitchen, which features classic white shaker cabinets,

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  197 N Ridge Run, Manchester Center, VT 05255
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  /40

  Est $504,769 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,560 Sq Ft

  466 Laver Rd, Arlington, VT 05250

  466 Laver Rd, Arlington, VT 05250
• 

  

  /31

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,317 Sq Ft

  9 F Cobble Ridge Rd, Winhall, VT 05340

  Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

  Carrie Mathews Winhall Real Estate

  9 F Cobble Ridge Rd, Winhall, VT 05340

Showing Results 161 - 200, Page 5 of 18