21,010

Bennington, VT Homes

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  • /28

    $1,700,000

    • 4 Beds
    • 3.5 Baths
    • 2,363 Sq Ft

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155

    Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

    Edwin Kevil Stratton Real Estate

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155
  • /57

    $800,000 Sold May 30, 2025

    • 3,390 Sq Ft
    • $236/SF
    • 77 Days On Market
    • 2 Beds
    • 4 Baths
    • Built 2005

    3149 Morse Hill Rd, Dorset, VT 05251

    Nestled in the scenic town of Dorset, this exquisite three-bedroom, four-bathroom home offers a perfect blend of comfort and sophistication. This latest addition to the market graces a generous 2,144 square feet of meticulously designed living space. Upon entry, you'll be greeted by an astonishingly modern sweet kitchen, boasting granite countertops, pretty white cupboards, a two tier bar and

    Nancy Greenwood Watson Realty & Associates

    3149 Morse Hill Rd, Dorset, VT 05251
    • /32

      Est $377,914 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 2,496 Sq Ft

      37 Glastenview Dr, Shaftsbury, VT 05262

      37 Glastenview Dr, Shaftsbury, VT 05262
  • /8

    $75,000

    • Land
    • 7 Acres
    • $10,534 per Acre

    272 Twenty Acre Wood Rd, Arlington, VT 05250

    Enjoy views all around on this ready to build on lot of over 7 acres. The views are 180 degrees , but you don't have to drive up a steep hill to get to them. Land has been surveyed house site cleared and septic permit in place.

    Andy Reed Four Seasons Sotheby's Int'l Realty

    272 Twenty Acre Wood Rd, Arlington, VT 05250
  • /22

    $289,000 Sold May 30, 2025

    • 1,833 Sq Ft
    • $158/SF
    • 93 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1920

    214 Prospect St, Bennington, VT 05201

    Beautiful in-town, 3-bedroom, 2-bathroom home is completely turn-key and ready to be your Vermont home! Perfectly situated in a sought-after neighborhood near the hospital, shops, and Bennington's many Main Street parades and festivals, it offers just the ideal blend of convenience and charm. So many recent upgrades and renovations, including a brand-new roof, furnace, significant tree removal

    Lori Hurley Four Corner Properties LLC

    214 Prospect St, Bennington, VT 05201
    • /39

      Est $463,212 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,136 Sq Ft

      20 Eastview Dr, Shaftsbury, VT 05262

      20 Eastview Dr, Shaftsbury, VT 05262
  • /25

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    393 Morse Hill Rd, East Dorset, VT 05253

    This beautifully maintained home is now available for the first time in 40 years.On the main level, you will find a generously sized eat-in kitchen with granite countertops that opens to a dining room. There are two additional rooms on the main level: a large living room and a bedroom. The main floor also boasts French door that leads out to a spacious deck, perfect for overlooking the

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    393 Morse Hill Rd, East Dorset, VT 05253
  • /27

    $262,000 Sold May 30, 2025

    • 1,200 Sq Ft
    • $218/SF
    • 173 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1972

    3623 Main Rd, Stamford, VT 05352

    Vermont fixer-upper home with ton of possibilities! Privacy, lots of land to have farm animals, 7.7 acres, close to North Adams, MA and its features like Mt. Greylock, Hoosac Tunnel and Mass MoCA, yet also close to Mt. Snow, VT for skiers, A lot of hiking trails all around this area, Appalachian Trail, Green Mountain National Forrest, VAST snowmobiling trail network, snowshoeing, endless fun!

    Michael Nuvallie NUVALLIE REALTY

    3623 Main Rd, Stamford, VT 05352
    • /29

      Est $464,291 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,272 Sq Ft

      106 Rollin Rd, North Bennington, VT 05257

      106 Rollin Rd, North Bennington, VT 05257
  • /24

    $42,000

    • Land
    • 0.48 Acre
    • $87,500 per Acre

    26 Asa's Way, Bennington, VT 05257

    Walking trails, a paved road, underground utilities, and water/sewer at the street, what more could you ask for? Situated high on Asa's Way, almost a half acre of slightly sloping and level lot is ready to build on. Over 200 feet of road frontage allows for many home designs; from a hillside house that maximizes the southerly sun, to a modern bungalow perched on a flat landing, bring your ideas!

    Angela Bevin Maple Leaf Realty

    26 Asa's Way, Bennington, VT 05257
  • /29

    $495,000 Sold May 29, 2025

    • 1,728 Sq Ft
    • $286/SF
    • 42 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1972

    117 Nottingham Park, Manchester Center, VT 05255

    Modern Chalet Vibes | Stylish Retreat with Nature Views. Looking for your own peaceful escape without sacrificing style? This beautifully maintained chalet-style home is nestled on nearly an acre (.92) of land in a quiet neighborhood, offering the perfect blend of rustic charm and modern upgrades. With a detached two-car garage and an elevated wrap-around deck, this home is designed for both

    David Halligan Four Seasons Sotheby's Int'l Realty

    117 Nottingham Park, Manchester Center, VT 05255
    • /20

      Est $426,445 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 1,781 Sq Ft

      1995 Trumbull Hill Rd, Shaftsbury, VT 05262

      1995 Trumbull Hill Rd, Shaftsbury, VT 05262
  • /41

    $335,000

    • 3 Beds
    • 1.5 Baths
    • 1,682 Sq Ft

    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
  • /43

    $401,000 Sold May 23, 2025

    • 2,692 Sq Ft
    • $149/SF
    • 124 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1932

    515 Hillside Dr, Pownal, VT 05261

    Discover Your Perfect Getaway at Verdmont...If you're a nature enthusiast, an exclusive opportunity awaits you at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this prestigious gated club offers nearly 500 acres of pristine wilderness. As a shareholder, you'll have access to a variety of exceptional amenities. *Water and Land Privilege: Enjoy two beautiful

    Kelley Mccarthy Mahar McCarthy Real Estate

    515 Hillside Dr, Pownal, VT 05261
    • /33

      Est $710,054 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,145 Sq Ft

      2005 Trumbull Hill Rd, Shaftsbury, VT 05262

      2005 Trumbull Hill Rd, Shaftsbury, VT 05262
  • /36

    $498,000

    • 3 Beds
    • 2 Baths
    • 1,671 Sq Ft

    6 Dwyers Camp Rd, Shaftsbury, VT 05262

    Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

    Lori Hurley Four Corner Properties LLC

    6 Dwyers Camp Rd, Shaftsbury, VT 05262
  • /18

    $155,000 Sold May 23, 2025

    • 819 Sq Ft
    • $189/SF
    • 170 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1989

    432 South St Unit A11, Bennington, VT 05201

    This beautiful two-bedroom, one-and-a-half-bath condominium offers comfortable one-level living in the desirable Nathaniel Court community. With numerous updates, this home is move-in ready and perfect for anyone seeking modern amenities in a serene setting.Enjoy the convenience of being within walking distance to downtown Bennington, with its charming shops, restaurants, and cultural

    Kelley Mccarthy Mahar McCarthy Real Estate

    432 South St Unit A11, Bennington, VT 05201
    • /38

      Est $460,391 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,904 Sq Ft

      293 Fox Hill Rd Unit PVT, Shaftsbury, VT 05262

      293 Fox Hill Rd Unit PVT, Shaftsbury, VT 05262
  • /60

    $1,825,000 Open House 8/30

    • 3 Beds
    • 4 Baths
    • 2,872 Sq Ft

    36 Beaver St, Bondville, VT 05340

    Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

    MaryKate Grey Stratton Real Estate

    36 Beaver St, Bondville, VT 05340
  • /32

    $645,000 Sold May 22, 2025

    • 2,700 Sq Ft
    • $239/SF
    • 12 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1986

    409 Bromley Brook Rd, Manchester Center, VT 05255

    Discover the perfect blend of rustic charm and modern convenience in this stunning 4-bedroom, 2-bathroom Log home nestled in scenic Manchester Center. This residence boasts a breathtaking 18-foot stone fireplace that anchors the living room, creating a cozy atmosphere for relaxing evenings. The spacious deck offers awe-inspiring mountain views, setting the stage for unforgettable gatherings or

    Brian Hill Remax Summit

    409 Bromley Brook Rd, Manchester Center, VT 05255
    • /32

      Est $343,610 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 1,928 Sq Ft

      317 Trumbull Hill Rd, Shaftsbury, VT 05262

      317 Trumbull Hill Rd, Shaftsbury, VT 05262
  • /42

    $439,000

    • 4 Beds
    • 1.5 Baths
    • 1,728 Sq Ft

    639 Wiley Mountain Rd, Readsboro, VT 05350

    Updated mountain home on 13.63 flat, usable acres bordering the Green Mountain National Forest and offering an outdoor paradise in every season. Tucked at the top of a quiet road, this property blends comfort, space, and access to Vermont’s best year-round recreation.Inside, you’ll find new hardwood floors, a renovated kitchen and bathrooms, a main-level bedroom, a full bath, main-level

    Melissa Nebelski Skihome Realty

    639 Wiley Mountain Rd, Readsboro, VT 05350
  • /46

    $800,000 Sold May 21, 2025

    • 3,560 Sq Ft
    • $225/SF
    • 34 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1790

    1 Monument Ave, Bennington, VT 05201

    This beautifully restored Old Bennington 4-bedroom Colonial, originally built in 1790 by Captain David Robinson, Jr., grandson of the founder of Bennington, seamlessly blends rich history with modern luxury. Located in the heart of the historic district, the home boasts breathtaking views of the Bennington Battle Monument, Mount Anthony, and the surrounding mountains. Meticulously updated, the

    Kelley Mccarthy Mahar McCarthy Real Estate

    1 Monument Ave, Bennington, VT 05201
    • /40

      Est $406,094 Not Listed For Sale

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

      1165 Hidden Valley Rd, Shaftsbury, VT 05262

      1165 Hidden Valley Rd, Shaftsbury, VT 05262
  • /55

    $2,225,000

    • 4 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    16 Hunter Ridge Rd, Bondville, VT 05340

    Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    16 Hunter Ridge Rd, Bondville, VT 05340
  • /60

    $235,000 Sold May 20, 2025

    • Land
    • 5.00 Acres
    • $47,000 per Acre
    • 88 Days On Market

    1304 Vermont Route 100, Readsboro, VT 05350

    Spectacular hillside lot with expansive 180 degree mountain views bordering the Green Mountain National Forest! Enjoy direct access to the VAST and VASA trail networks to horseback ride, snowmobile, ATV, snowshoe, cross country ski, mountain bike, and hike. There are seemingly endless trails to explore and wildlife galore! This 5 acre lot is build ready. All of the major legwork has been done. 3

    Lisa Friedman Great American Dream Realty

    1304 Vermont Route 100, Readsboro, VT 05350
    • /40

      Est $554,365 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,464 Sq Ft

      84 Marshall Dr Unit PVT, Shaftsbury, VT 05262

      84 Marshall Dr Unit PVT, Shaftsbury, VT 05262
  • /48

    $2,095,000

    • 5 Beds
    • 4.5 Baths
    • 3,218 Sq Ft

    5491 Vt Route 315, Rupert, VT 05776

    Set on 5+ peaceful acres with stream frontage and panoramic mountain views, this fully renovated 1909 Federal offers timeless character with a like-new feel—just 2.5 miles from the Dorset Green and dining but away from the bustle. Every inch of the main home has been meticulously updated with premium materials and workmanship. A custom walnut kitchen with high-end built in appliances with island

    Annette Gallo Real Broker LLC

    5491 Vt Route 315, Rupert, VT 05776
  • /7

    $75,000 Sold May 20, 2025

    • Land
    • 31 Acres
    • $2,419 per Acre
    • 261 Days On Market

    00 Vermont 8, Readsboro, VT 05350

    Discover 31 stunning acres in Southern Vermont, ideally situated just 10 minutes from the Massachusetts border. Enjoy the convenience to Williams College, MASS MoCA in North Adams, and Berkshire East Mountain Resort all less than 30 minutes away. For outdoor enthusiasts, Harriman Reservoir in Wilmington, VT, is just down the road, offering endless opportunities for boating, kayaking, and fishing.

    Kim Meeker Southern Vermont Realty Group

    00 Vermont 8, Readsboro, VT 05350
    • /39

      Est $1,576,539 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,433 Sq Ft

      1036 Myers Rd, Shaftsbury, VT 05262

      1036 Myers Rd, Shaftsbury, VT 05262
  • /22

    $895,000

    • Land
    • 24 Acres
    • $37,168 per Acre

    A Windsor Rd, Manchester, VT 05255

    Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

    Kim Morgan-Wohler Wohler Realty Group

    A Windsor Rd, Manchester, VT 05255
  • /45

    $750,500 Sold May 20, 2025

    • 2,576 Sq Ft
    • $291/SF
    • 27 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2015

    688 Rice Ln, Bennington, VT 05201

    Imagine sitting on your wraparound porch or second story deck looking out over 16 protected acres, your own pond and a view of the White Rocks. Now, imagine going inside to your custom kitchen with cherry cabinets, granite counters and a large butcher block island. The open plan continues throughout the first floor living area with one of two fireplaces, half bath, laundry and a tiled mudroom.

    Cassie Barbeau Mahar McCarthy Real Estate

    688 Rice Ln, Bennington, VT 05201
    • /35

      Est $625,888 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,078 Sq Ft

      1425 W Mountain Rd, Shaftsbury, VT 05262

      1425 W Mountain Rd, Shaftsbury, VT 05262
  • /31

    $259,000

    • 2 Beds
    • 1 Bath
    • 836 Sq Ft

    473 South Rd, East Arlington, VT 05252

    This is an exceptional opportunity at this price point as a starter home for individuals or young families. This quaint craftsman home sits in the town of Sunderland and is the ideal location situated between Manchester and Bennington, Vermont. It is a 2.5 mile drive to the village of Arlington. This location boasts School Choice for families, to include Burr and Burton Academy. A mudroom

    Robert Sabol Wohler Realty Group

    473 South Rd, East Arlington, VT 05252
  • /34

    $175,000 Sold May 16, 2025

    • 1,056 Sq Ft
    • $166/SF
    • 9 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1993

    106 Park St Unit 8, Bennington, VT 05201

    Bright and sunny with gleaming floors, this second floor flat is absolutely turnkey! 2BR/2BA with dedicated laundry room, open kitchen/living/dining opens onto a covered balcony with room for outdoor seating and taking in the mountain views. Brand new boiler, assigned parking. Walking distance to all things downtown Bennington. Well managed COA offers peace of mind, this is a great

    Vicki Wilson Maple Leaf Realty

    106 Park St Unit 8, Bennington, VT 05201
    • /39

      Est $453,056 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,716 Sq Ft

      235 Blueberry Hill Rd, Shaftsbury, VT 05262

      235 Blueberry Hill Rd, Shaftsbury, VT 05262
  • /36

    $1,790,000

    • 4 Beds
    • 3 Baths
    • 2,139 Sq Ft

    1949 South Rd, Peru, VT 05152

    Nestled in a serene and picturesque setting, Berry Hill Farm offers a rare opportunity to own an exceptional Vermont estate blending charm, versatility, and natural beauty. Spanning 15.52 acres across two separately deeded lots, the property combines inspired design with modern comfort. At its heart is a beautifully crafted contemporary home featuring three spacious bedrooms, sunlit living

    Kim Morgan-Wohler Wohler Realty Group

    1949 South Rd, Peru, VT 05152
  • /51

    $905,000 Sold May 16, 2025

    • 3,800 Sq Ft
    • $238/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2004

    255 Mending Walls Rd, Manchester Center, VT 05255

    Looking for the perfect mix of charm, warmth, and modern convenience? This Manchester farmhouse has it all! With 4 bedrooms, 4 baths, and 3800 sq. ft. of beautifully designed living space, there’s room for everyone. Step inside to find a charming entry, dining room with fireplace, sun-filled family room, an eat-in kitchen with chef’s appliances and granite counters, and a first-floor primary

    David Citron RE/MAX Four Seasons

    255 Mending Walls Rd, Manchester Center, VT 05255
    • /40

      Est $602,796 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,396 Sq Ft

      349 Blueberry Hill Rd, Shaftsbury, VT 05262

      349 Blueberry Hill Rd, Shaftsbury, VT 05262
  • /45

    $3,600,000

    • 4 Beds
    • 3.5 Baths
    • 2,338 Sq Ft

    198 Church St, Dorset, VT 05251

    Nestled in the heart of the iconic Dorset village, just steps from the Dorset Field Club and the beloved local theater, this enchanting historic home has been meticulously renovated, rejuvenated, and reimagined with no expense spared. From the moment you arrive, the home's timeless charm and thoughtful updates are evident. A complete reengineering of the roof and replacement of all major systems

    Adrienne Sherwood Four Seasons Sotheby's Int'l Realty

    198 Church St, Dorset, VT 05251

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