140

Bennington County VT Houses for Sale

Section Image
  • /38

    $525,000

    • 4 Beds
    • 3 Baths
    • 2,073 Sq Ft

    2588 Vermont 11, Peru, VT 05152

    PRICE ADJUSTMENT: On a gentle rise surrounded by 7.5 acres of meadows and woodland, this Vermont style ranch subtly blends an appealing rustic charm with contemporary features. The current owners purchased the property in 2021 for family and friends and installed a new wastewater system, new furnace, new roof section, new appliances. The rough sawn clapboard exterior delineates the enduring

    Diana Stugger Four Seasons Sotheby's Int'l Realty

    2588 Vermont 11, Peru, VT 05152
  • /34

    $269,900

    • 3 Beds
    • 2.5 Baths
    • 1,810 Sq Ft

    3530 Vt Route 346, Pownal, VT 05261

    This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially

    Matt Waddington Hoffman Real Estate

    3530 Vt Route 346, Pownal, VT 05261
  • /19

    $219,500

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft

    14 Robinson Ave, Bennington, VT 05201

    Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

    Timothy Corcoran Mahar McCarthy Real Estate

    14 Robinson Ave, Bennington, VT 05201
  • /38

    $1,200,000

    • 5 Beds
    • 1 Bath
    • 2,228 Sq Ft

    395 King Hill Rd, Readsboro, VT 05350

    Stunning Mountain & Meadow Views, 135 acres of pristine rolling meadows overlook the Harriman Reservoir, sits a meticulously maintained c. 1770 5 bedroom farmhouse. Welcome to King Hill Farm, this idyllic Vermont homestead has been in the King family for multiple generations. No restrictions, enjoy the peace and quiet of a slight breeze, blue skies and bird songs. Remarkable, one of a kind

    Margretta Fischer Wohler Realty Group

    395 King Hill Rd, Readsboro, VT 05350
  • /33

    $525,000

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    3 Strattonwald Rd, Winhall, VT 05340

    Lovingly renovated and move-in ready, this 3-bedroom chalet is your ideal mountain escape in the sought-after Strattonwald neighborhood. Take in beautiful views of Stratton Mountain from the comfort of your home while enjoying the warmth and character of this thoughtfully updated retreat. Inside, you’ll find a brand-new kitchen and updated bathroom, stone wood burning fireplace, gleaming hardwood

    Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Strattonwald Rd, Winhall, VT 05340
  • /22

    $950,000

    • 4 Beds
    • 3 Baths
    • 3,659 Sq Ft

    445 Canterbury Rd, Manchester Center, VT 05255

    Nestled in one of Vermonts most sought-after locations, this exceptional Colonial home boasts sweeping panoramic views of the Green Mountain National Forest and the picturesque Northshire Valley, offering a peaceful and private retreat just minutes from the vibrant town of Manchester. Perfectly oriented to capture stunning morning sunrises, this 2.8-acre property provides the ideal balance of

    Andy Reed Four Seasons Sotheby's Int'l Realty

    445 Canterbury Rd, Manchester Center, VT 05255
  • /45

    $350,000

    • 4 Beds
    • 1 Bath
    • 1,680 Sq Ft

    19 Royal St, North Bennington, VT 05257

    Charming North Bennington Home in a Desirable Neighborhood.Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College.Step inside to discover a freshly

    Lindsey Martin Maple Leaf Realty

    19 Royal St, North Bennington, VT 05257
  • /38

    $1,995,000

    • 5 Beds
    • 3 Baths
    • 6,323 Sq Ft

    2589 W Sandgate Rd, Arlington, VT 05250

    Two Pigs Farm is a hillside retreat in Southern Vermont's Taconic Range, where meadows are bound by ancient maple trees, stone walls and two clear brooks. The circa 1989 farmhouse and barns feel timeless—rooted, quietly graceful—designed for comfort, and connection. Inspired by childhood summers in Sandgate, the owner dreamed of a place where time stretches—mornings for berry picking, afternoons

    Dia Jenks LandVest, Inc/Woodstock

    2589 W Sandgate Rd, Arlington, VT 05250
  • /38

    $980,000

    • 4 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    25 Benson Fuller Dr, Jamaica, VT 05343

    Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Jamaica, VT 05343
  • /23

    $4,000,000

    • 5 Beds
    • 2 Baths
    • 3,347 Sq Ft

    15 Wind Hill Rd, Manchester Center, VT 05255

    At the heart of this remarkable 136-acre property in Manchester Center, Vermont, are two distinct historic homes, each telling a story of the land’s deep roots in the Beattie-Forrest family, who have stewarded it for over a century.The original farmhouse, built circa 1800, offers five bedrooms and two baths, with timeless details including a vintage kitchen and hand-hewn timber framing.

    Paul Carroccio TPW Real Estate

    15 Wind Hill Rd, Manchester Center, VT 05255
  • /44

    $88,500

    • 5 Beds
    • 1 Bath
    • 1,952 Sq Ft

    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
  • /34

    $500,000

    • 1 Bed
    • 2 Baths
    • 300 Sq Ft

    417 Maple Hill Rd, Arlington, VT 05250

    Scandinavian Timber Frame Tiny House & Grindbygg! Over 10 acres of privacy and beautiful vistas. 360 degree mountain view from this custom heartfelt build. The property includes a one bedroom tiny house complete with kitchen, gas range, wood stove, movie projector, sleeping loft and so much more. A drilled well, on demand propane hot water heater and water shed for water storage. This cozy

    Margretta Fischer Wohler Realty Group

    417 Maple Hill Rd, Arlington, VT 05250
  • /30

    $1,300,000

    • 11 Beds
    • 9 Baths
    • 9,560 Sq Ft

    3309 3321 Main St, Manchester, VT 05254

    A Rare Opportunity! Introducing a historically significant gem, available for the first time in over 40 years. Set in the picturesque and highly sought after Manchester Village, this timeless estate includes a grand Main House and a charming Carriage House, each situated on its own adjoining 1.27-acre lot, totaling an expansive 2.54 park-like acres. Together, the residences offer 11 bedrooms, 6

    Gregory Cutler Four Seasons Sotheby's Int'l Realty

    3309 3321 Main St, Manchester, VT 05254
  • /31

    $150,000

    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft

    109 Evergreen Dr, Bennington, VT 05201

    House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front

    Zachary Zupan EXP Realty

    109 Evergreen Dr, Bennington, VT 05201
  • /41

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,116 Sq Ft

    245 Southshire Dr, Bennington, VT 05201

    Nestled in one of Bennington's most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm--all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System(BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious

    Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

    245 Southshire Dr, Bennington, VT 05201
  • /59

    $549,000

    • 4 Beds
    • 2 Baths
    • 1,828 Sq Ft

    69 Hillvale Dr, Manchester Center, VT 05255

    This is a wonderful craftsman style ranch in a great location right in the heart of Manchester, in the sunny Hillvale neighborhood. It offers views to Mt. Equinox and is walking access to all Manchester's amenities. Four bedrooms, two full baths, updated kitchen with stainless appliances and granite counter tops, the dining room's french door opens on to an expansive deck for BBQ's and

    Robert Sabol Wohler Realty Group

    69 Hillvale Dr, Manchester Center, VT 05255
  • /27

    $1,250,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    233 Squires Rd, Manchester Center, VT 05255

    Discover a rare opportunity to live and work amidst the serene beauty of Manchester, Vermont. This fully renovated 2-bedroom, 1-bath contemporary ranch, with leased solar array, is nestled on nearly 19 acres, offering a harmonious blend of modern comfort and entrepreneurial potential.The open-concept design features a spacious kitchen and living area, complemented by energy-efficient

    Mark Triller Real Broker LLC

    233 Squires Rd, Manchester Center, VT 05255
  • /49

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    93 Pace Rd, Bennington, VT 05201

    Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

    Harvey Roettinger RE/MAX North Professionals

    93 Pace Rd, Bennington, VT 05201
  • /34

    $499,000

    • 3 Beds
    • 3 Baths
    • 1,696 Sq Ft

    104 Johnny Cake Hill Ln, Readsboro, VT 05350

    If you've been dreaming of peaceful country living with stunning views, this one-of-a-kind home on approximately 22 private acres in the hills of Southern Vermont is calling your name. Greet each morning with an awe-inspiring easterly panorama that, on clear days, stretches all the way to Mount Monadnock.This serene retreat offers the best of nature — birdsong in the morning, occasional

    Monica Sumner BHG Masiello Brattleboro

    104 Johnny Cake Hill Ln, Readsboro, VT 05350
  • /31

    $1,495,000

    • 5 Beds
    • 5 Baths
    • 6,200 Sq Ft

    951 Rupert Rd, Arlington, VT 05250

    Discover this irresistible Vermont estate near the New York border. Tucked down a long private drive, the home evokes a Scottish countryside manor. The spacious layout features a first-floor primary suite with two walk-in closets and a spa-like bath with dual sinks and a Jacuzzi tub. The large kitchen, with fireplace and breakfast nook, opens to a formal dining room overlooking your own personal

    Kristin Pirie KW Vermont Woodstock

    951 Rupert Rd, Arlington, VT 05250
  • /11

    $179,900

    • 4 Beds
    • 2 Baths
    • 2,643 Sq Ft

    905 County St, Bennington, VT 05201

    Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    905 County St, Bennington, VT 05201
  • /7

    $350,000

    • 4 Beds
    • 2 Baths
    • 1,368 Sq Ft

    72 Mckee Rd, Arlington, VT 05250

    This charming 1985 Cape Cod style home, situated on 2.4 acres, is now available.The first floor features a kitchen with a cathedral ceiling, a comfortable living room, and two bedrooms. Upstairs, you will find an additional two bedrooms and a bathroom. The home also includes a full unfinished basement, offering potential for future expansion or storage. The barn could be used as a

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    72 Mckee Rd, Arlington, VT 05250
  • /50

    $1,499,000

    • 6 Beds
    • 7 Baths
    • 5,400 Sq Ft

    2001 Depot St, Manchester Center, VT 05255

    LOCATION, LOCATION: 8 minutes from Bromley, 20 minutes to Stratton, yet close to Manchester restaurants, shopping, fishing, Horse Show & golf. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bathroom retreat offers 5,400+ square feet of living space on 3.2 private acres—perfect for use as a primary residence, vacation getaway, or a return to its B&B roots.

    Steven Bryant TPW Real Estate

    2001 Depot St, Manchester Center, VT 05255
  • /50

    $374,900

    • 5 Beds
    • 4 Baths
    • 3,400 Sq Ft

    927 Water St, North Bennington, VT 05257

    Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres.Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and

    Brenda Jones KW Vermont - Brenda Jones Real Estate Group

    927 Water St, North Bennington, VT 05257
  • /42

    $1,950,000

    • 9 Beds
    • 7 Baths
    • 6,956 Sq Ft

    1086 West Rd, Bennington, VT 05201

    Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

    Chris DeFelice Four Seasons Sotheby's Int'l Realty

    1086 West Rd, Bennington, VT 05201
  • /50

    $4,875,000

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

    318 Spring Hill Ln, Dorset, VT 05251

    Welcome to a truly exceptional estate where classic charm and modern craftsmanship unite on 9 secluded acres in the heart of coveted Dorset, Vermont. Meticulously curated with no detail overlooked and no expense spared, this remarkable property features a beautifully renovated 1941 Colonial residence, complemented by a collection of newer luxury companion buildings that together create a one of a

    Richard Slocum Four Seasons Sotheby's Int'l Realty

    318 Spring Hill Ln, Dorset, VT 05251
  • /48

    $599,900

    • 4 Beds
    • 3.5 Baths
    • 3,742 Sq Ft

    34 Southshire Dr, Bennington, VT 05201

    Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

    Kelley Mccarthy Mahar McCarthy Real Estate

    34 Southshire Dr, Bennington, VT 05201
  • /37

    $1,275,000

    • 4 Beds
    • 4 Baths
    • 4,266 Sq Ft

    693 Longview Dr, Manchester, VT 05255

    This four-bedroom, four-bath home offers not only exceptional views and privacy but also the convenience of an in-town location. It's ideally situated in Manchester Village, set on three landscaped acres featuring mature trees, custom stonework, level lawns, and active brook.The interior of the home provides a comfortable living space. On the Main Level, you'll find a spacious living room

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    693 Longview Dr, Manchester, VT 05255
  • /33

    $1,274,999

    • 4 Beds
    • 2.5 Baths
    • 4,620 Sq Ft

    139 Village View Rd, Manchester, VT 05255

    From morning coffee on the deck to cozy evenings by the fire, this Manchester home is designed for comfort, flexibility, and four-season living. The main level features a bright great room, an eat-in kitchen with an adjacent covered porch, a formal dining room, a den with a fireplace, two bedrooms, a full bath, and a primary suite with a walk-in shower and a jetted tub.The finished lower

    Marek Kovac TPW Real Estate

    139 Village View Rd, Manchester, VT 05255
  • /21

    $895,000

    • 4 Beds
    • 5.5 Baths
    • 4,213 Sq Ft

    262 Powderhorn Rd, Manchester Center, VT 05255

    Stunning Contemporary Retreat with Indoor Pool on Nearly 2 AcresWelcome to this beautiful 5-bedroom, 5-bath contemporary home nestled on a sunny 1.9+/- acre lot. Designed for both comfort and style, this expansive residence features a 16' x 32' heated indoor swimming pool, perfect for year-round enjoyment.Originally built in 1973 and extensively renovated in 2000, the home blends timeless

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    262 Powderhorn Rd, Manchester Center, VT 05255
  • /52

    $199,000

    • 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.

    Dan Mason Perrott Realty

    130 Morgan St, Bennington, VT 05201
  • /21

    $370,000

    • 3 Beds
    • 1.5 Baths
    • 1,116 Sq Ft

    6 Deep Woods Rd, Winhall, VT 05255

    Escape to your cozy log ski chalet nestled on a private acre in the charming town of Winhall, Vermont! This delightful 3-bedroom, 1.5-bath home offers 1116 square feet of rustic charm and modern comfort. Imagine returning from a thrilling day on the slopes of nearby Stratton or Bromley, just a short drive away, and unwinding by the crackling outdoor fireplace on your spacious patio, with festive

    Robin Apps Four Seasons Sotheby's Int'l Realty

    6 Deep Woods Rd, Winhall, VT 05255
  • /51

    $970,000

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

    24 Vt Route 11, Londonderry, VT 05148

    Step into a world of potential with this beautiful country retreat, set on the edge of pristine Green Mountain National Forest. Adventure truly begins here, with nearby access to the Catamount Trail and four renowned ski areas just minutes away. Once home to the beloved Nordic Inn, this versatile property carries a rich legacy of hospitality, having once hosted a restaurant and cross-country ski

    Nancy Jensen Four Seasons Sotheby's Int'l Realty

    24 Vt Route 11, Londonderry, VT 05148
  • /54

    $1,875,000

    • 3 Beds
    • 3 Baths
    • 5,228 Sq Ft

    2167 Myers Rd, Shaftsbury, VT 05262

    Welcome to Hidden Ponds Farm!!! Nestled amidst 40 sprawling acres, this historic early 1800's post and beam converted barn is a rare gem combining rustic charm with modern comforts. The property is highlighted by a stunning 1,000-foot hand-placed stone wall, two picturesque ponds, and two orchards offering seasonal beauty and fresh fruit. The expansive outdoor space also features a hot tub,

    Kelley Mccarthy Mahar McCarthy Real Estate

    2167 Myers Rd, Shaftsbury, VT 05262
  • /42

    $299,000

    • 2 Beds
    • 2 Baths
    • 1,624 Sq Ft

    516 Oberdorf Rd, Readsboro, VT 05350

    Outdoor lover’s paradise in Alpenwald Village! This beautifully updated 2-bedroom, 2-bath home sits on an ample 2.5 acres and abuts National Forest land—perfect for year-round adventure. Step inside to your open kitchen and a bright family room with cathedral ceilings and a sliding door that opens to a peaceful back porch with stunning mountain views. The spacious mudroom offers plenty of room

    Lindsey Martin Maple Leaf Realty

    516 Oberdorf Rd, Readsboro, VT 05350
  • /27

    $595,000

    • 2 Beds
    • 2 Baths
    • 3,478 Sq Ft

    142 Mount Aeolus Rd, Manchester, VT 05255

    A Rare Investment Opportunity in Manchester! This versatile property offers the perfect blend of commercial and residential potential, making it an ideal choice for savvy investors or those seeking a live-work setup. The upstairs features a spacious residential rental, while the lower level was recently leased to a local daycare, providing immediate rental income.This well-maintained property

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    142 Mount Aeolus Rd, Manchester, VT 05255
  • /12

    $499,000

    • 6 Beds
    • 4 Baths
    • 15,179 Sq Ft

    423 Main St, Bennington, VT 05201

    Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor

    Chris Long BHG Masiello Brattleboro

    423 Main St, Bennington, VT 05201
  • /34

    $1,350,000

    • 4 Beds
    • 2.5 Baths
    • 4,634 Sq Ft

    1677 Barnumville Rd, Manchester Center, VT 05255

    This historic 19th century two-story brick Federal house was originally a popular tavern. It has been completely renovated/updated to serve today's relaxed living while retaining all classic features. A bright kitchen/dining/living great room w/fireplace is the heart of the home. A first-floor master suite includes a spa-like bath w/fireplace. There is an adjacent mudroom entrance with 1/2 bath

    R. Diedrich August Wohler Realty Group

    1677 Barnumville Rd, Manchester Center, VT 05255
  • /31

    $949,000

    • 4 Beds
    • 4.5 Baths
    • 2,658 Sq Ft

    73 Cranberry Hill Rd, Winhall, VT 05340

    Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

    Carrie Mathews Winhall Real Estate

    73 Cranberry Hill Rd, Winhall, VT 05340
  • /44

    $2,500,000

    • 5 Beds
    • 7 Baths
    • 7,625 Sq Ft

    19 Old Town Rd, Bondville, VT 05340

    Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

    Christiane Carroccio TPW Real Estate

    19 Old Town Rd, Bondville, VT 05340

Showing Results 81 - 120, Page 3 of 4

How to Buy a Home How to Finance a Home How to Sell a Home