235

Bennington County VT Homes for Sale

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  • /43

    $2,100,000

    • 4 Beds
    • 3 Baths
    • 3,780 Sq Ft

    1228 Skiparee Rd, Pownal, VT 05260

    Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

    Christiane Carroccio TPW Real Estate

    1228 Skiparee Rd, Pownal, VT 05260
  • /12

    $399,500

    $11K PRICE DROP
    • Land
    • 2.7 Acres
    • $147,963 per Acre

    2937 Dorset Rd W, Dorset, VT 05251

    Prime Buildable Lot in Dorset! Embrace the Best of All Worlds! Discover a rare opportunity to own a ready-to-build lot in the heart of Dorset, perfectly positioned to offer unparalleled access to the town's finest attractions. Just moments from scenic hiking trails, the picturesque Dorset Green, and the esteemed Dorset Field Club, this property is your gateway to a lifestyle of outdoor adventure

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    2937 Dorset Rd W, Dorset, VT 05251
  • /49

    $2,200,000

    • 4 Beds
    • 3.5 Baths
    • 4,265 Sq Ft

    7537 Main St, Manchester Center, VT 05255

    Perched to capture sweeping easterly views of Vermont’s mountains, this re-imagined Manchester home lives large. Completely renovated and redesigned in 2022, the pristine property blends timeless materials with modern comforts and efficiency. Danby marble, light oak flooring, high-end fixtures, and antique barn beams anchor the Great Room, while expansive windows fill the home with natural light

    Elena Atwill Four Seasons Sotheby's Int'l Realty

    7537 Main St, Manchester Center, VT 05255
  • /23

    $252,500

    $7K PRICE DROP
    • Land
    • 17.6 Acres
    • $14,347 per Acre

    88 Cedar Ln, Peru, VT 05152

    Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

    Joe Castaluccio Winhall Real Estate

    88 Cedar Ln, Peru, VT 05152
  • /24

    $229,000

    $6K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    340 Pleasant St, Bennington, VT 05201

    Downtown Bennington duplex with income in place and upside potential. The lower unit has been completely renovated, featuring a new kitchen, updated bathroom, and new flooring throughout. Exterior and structural improvements include a repointed foundation, fully sided exterior, new roof, and a gravel driveway. Bennington continues to see investment, revitalization, and ongoing redevelopment in

    Melissa Nebelski Real Broker LLC

    340 Pleasant St, Bennington, VT 05201
  • /42

    $345,000

    • 3 Beds
    • 1 Bath
    • 1,768 Sq Ft

    2154 U S 7, Pownal, VT 05261

    Charming antique Cape full of character and opportunity. This 3-bedroom, 1-bath home offers timeless New England charm with warm, inviting living spaces and a flexible layout ready for your personal touch. A first-floor bedroom and first-floor laundry provide the convenience of single-level living, while additional bedrooms upstairs offer flexibility for guests or office space. Original details

    Angela Bevin Maple Leaf Realty

    2154 U S 7, Pownal, VT 05261
  • /14

    $2,500,000

    • Land
    • 227 Acres
    • $11,013 per Acre

    00 Vermont 11, Peru, VT 05152

    Bordering Green Mountain National Forest with sweeping views of Stratton, Bromley, and Magic Mountains, this 227 +/- acre offering in Peru, Vermont captures the scale, privacy, and natural beauty that define Southern Vermont mountain living.Spanning two distinct parcels, the offering includes 199 +/- acres bordering National Forest land and a separate 28 +/- acre parcel positioned to capture

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    00 Vermont 11, Peru, VT 05152
  • /40

    $439,500

    $40K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,861 Sq Ft

    120 Village St, East Dorset, VT 05253

    Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

    Dana Kingsley Josiah Allen Real Estate, Inc.

    120 Village St, East Dorset, VT 05253
  • /3

    $109,000

    • Land
    • 17 Acres
    • $6,412 per Acre

    00 Bill T Dr, Readsboro, VT 05350

    Escape to the Green Mountains with this beautiful 17-acre parcel located at the end of a town-maintained road in scenic Readsboro, Vermont. This private property offers the perfect mix of seclusion and convenience, surrounded by nature and outdoor recreation opportunities. At the rear of the property, you’ll find a serene beaver pond that attracts moose, birds, and other local wildlife—an ideal

    Samantha Decker Deerfield Valley Real Estate

    00 Bill T Dr, Readsboro, VT 05350
  • /52

    $895,000

    $75K PRICE DROP
    • 6 Beds
    • 8 Baths
    • 5,764 Sq Ft

    24 Vt Route 11, Londonderry, VT 05148

    Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection. Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chef’s kitchen, sun-filled all-season

    Nancy Jensen Four Seasons Sotheby's Int'l Realty

    24 Vt Route 11, Londonderry, VT 05148
  • /26

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,688 Sq Ft

    67 Valley Pass, Manchester, VT 05255

    Welcome to 67 Valley Pass Road, where your new Vermont home awaits. This stylish split-level ranch has been meticulously maintained and is truly move in ready. The home features four bedrooms, highlighted by a spacious primary bedroom with an en suite bathroom.The upper level offers an updated open kitchen and dining area with an easy flowing layout. Just off the dining space is a cozy living

    Sara Buckley Josiah Allen Real Estate, Inc.

    67 Valley Pass, Manchester, VT 05255
  • /38

    $860,000

    $120K PRICE DROP
    • 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 chilly

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Jamaica, VT 05343
  • /32

    $449,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    32 Aspen Ln, Winhall, VT 05340

    A Sanctuary for Every Season:Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you’re here to chase the morning light on the slopes of nearby Stratton Resort or to spend a

    Robin Apps Four Seasons Sotheby's Int'l Realty

    32 Aspen Ln, Winhall, VT 05340
  • /18

    $195,000

    • 3 Beds
    • 1 Bath
    • 1,590 Sq Ft

    176 Glen Ave, Readsboro, VT 05350

    Charming and spacious 3-bedroom, 1-bath home situated on approximately 1.90 acres, offering warm character and generous living space. Beautiful wood floors flow throughout the home, complemented by fresh paint, making this property truly move-in ready.The expansive wrap-around porch is a standout feature, perfect for enjoying quiet mornings, relaxing afternoons, or entertaining family and

    Cassandra Ehrlich BHG Masiello Brattleboro

    176 Glen Ave, Readsboro, VT 05350
  • /16

    $495,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255

    Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace.The

    Northshire Sales Group Real Broker LLC

    14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255
  • /37

    $584,900

    • 3 Beds
    • 2.5 Baths
    • 1,786 Sq Ft

    14A Marisa Ln, Dorset, VT 05251

    Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

    Julie Citron RE/MAX Four Seasons

    14A Marisa Ln, Dorset, VT 05251
  • /41

    $1,425,000

    Open Sun 2PM - 4PM $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,931 Sq Ft

    932 Mcnamara Rd, Dorset, VT 05251

    Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality throughout. Soaring

    Britt Wohler

    932 Mcnamara Rd, Dorset, VT 05251
  • /15

    $299,000

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

    1803 Harwood Hill Rd, Bennington, VT 05201

    Set on a spacious lot and move-in ready raised ranch offers major updates, flexible living space, and excellent value. Recent improvements include a brand-new septic system, new roof, beautifully renovated kitchen, and new deck — giving buyers peace of mind and modern comfort from day one.The versatile lower level provides additional finished space ideal for a home office, family room, guest

    Lori Hurley Four Corner Properties LLC

    1803 Harwood Hill Rd, Bennington, VT 05201
  • /6

    $145,000

    • Land
    • 3 Acres
    • $48,333 per Acre

    530 Finbars Forest Rd, Manchester Center, VT 05255

    This building lot borders the Manchester Country Club and, with tree clearing, would offer amazing views of the golf course and the Manchester mountains. The location provides easy access to town and everything the area has to offer. This private wooded lot is just minutes away from local highlights, including golf, skiing, hiking, and shopping. Septic permit and design available.

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    530 Finbars Forest Rd, Manchester Center, VT 05255
  • /28

    $159,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 760 Sq Ft

    1675 Vermont 9, Searsburg, VT 05363

    Welcome to Peaceful Pines, your cottage in the woods near the entrance to the Green Mountain National Forest. The charming two-bedroom cottage/camp was lovingly maintained. Key updates include a completely rebuilt chimney and masonry work, a wood stove ( in addition to baseboard heat) to take the chill out of those fall and winter evenings, T11 siding, a newer roof, and a private back deck with

    Jacki Murano Southern Vermont Realty Group

    1675 Vermont 9, Searsburg, VT 05363
  • /38

    $324,900

    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    2 Pine Rd, Bennington, VT 05201

    Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

    Brenda Jones KW Vermont - Brenda Jones Real Estate Group

    2 Pine Rd, Bennington, VT 05201
  • /23

    $329,900

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,030 Sq Ft

    773 Oberdorf Rd, Readsboro, VT 05350

    Discover cozy mountain living in this charming Alpenwald chalet, where rustic character meets thoughtful modern updates. Nestled among the trees, this inviting retreat offers a bright, open floor plan filled with natural light from expansive windows and sliding glass doors. Recently remodeled, the kitchen and both full bathrooms bring a fresh, updated feel, while a comfortable bar area adds the

    Sean Taylor Moresi Real Estate Partners

    773 Oberdorf Rd, Readsboro, VT 05350
  • /40

    $5,900,000

    $1M PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    515 W Fields Rd, Manchester, VT 05254

    Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rareand exceptional 5-bedroom, 6-bathroom home....The creative design of Architect Ramsey Gourd and Master Builder Mark Breen, well knownas two of Southern Vermont's

    Sunny Breen Josiah Allen Real Estate, Inc.

    515 W Fields Rd, Manchester, VT 05254
  • /10

    $245,000

    $97K PRICE DROP
    • Land
    • 28.5 Acres
    • $8,596 per Acre

    11 Old County Rd E, Londonderry, VT 05148

    A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    11 Old County Rd E, Londonderry, VT 05148
  • /47

    $845,000

    • 5 Beds
    • 5.5 Baths
    • 3,875 Sq Ft

    1629 Mann Hill Rd N, Pownal, VT 05261

    Facing west to capture breathtaking mountain views and unforgettable sunsets from nearly every room, this stunning modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors and cozy alcoves create warmth and charm throughout, while original beams in the living room add a touch of history and authenticity. The spacious layout offers 5 bedrooms, each with

    Kelley Mccarthy Mahar McCarthy Real Estate

    1629 Mann Hill Rd N, Pownal, VT 05261
  • /12

    $299,999

    • Land
    • 10.05 Acres
    • $29,851 per Acre

    00 Garden Loop Rd, Winhall, VT 05340

    The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

    David White OwnerEntry.com

    00 Garden Loop Rd, Winhall, VT 05340
  • /45

    $275,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    951 Gage St, Bennington, VT 05201

    This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

    Dan Mason Perrott Realty

    951 Gage St, Bennington, VT 05201
  • /31

    $1,200,000

    • 1 Bath
    • 950 Sq Ft

    109 Winhall Hollow Rd, Winhall, VT 05340

    Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    109 Winhall Hollow Rd, Winhall, VT 05340
  • /7

    $145,000

    $30K PRICE DROP
    • Land
    • 15.49 Acres
    • $9,361 per Acre

    00 Silk Rd, Bennington, VT 05201

    Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

    David White OwnerEntry.com

    00 Silk Rd, Bennington, VT 05201
  • /46

    $1,550,000

    • 5 Beds
    • 5 Baths
    • 6,129 Sq Ft

    1035 Holy Smoke Rd, Shaftsbury, VT 05262

    Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

    Lori Hurley Four Corner Properties LLC

    1035 Holy Smoke Rd, Shaftsbury, VT 05262
  • /12

    $865,000

    • 12 Beds
    • 8 Baths
    • 5,568 Sq Ft

    1931 Vermont Route 67 E, Shaftsbury, VT 05262

    Rare investment opportunity in one of the area’s most desirable neighborhoods! This unique offering includes two historic buildings set on a spacious 1-acre lot, featuring a total of 8 well-maintained units—comprised of (4) two-bedroom apartments and (4) one-bedroom apartments. Each building offers shared covered front porches, perfect for enjoying the charm of this pleasant street setting. The

    Julie Glover Mahar McCarthy Real Estate

    1931 Vermont Route 67 E, Shaftsbury, VT 05262
  • /39

    $349,000

    • 4 Beds
    • 2 Baths
    • 1,814 Sq Ft

    1153 King Hill Rd, Readsboro, VT 05350

    This recently updated 1920s Vermont farmhouse features 4 bedrooms, 2 full bathrooms, and a versatile loft space on just over 8 acres! Large, updated windows showcase mountain views and allow natural light to fill every room, highlighting the home's charming original details alongside modern updates. The first floor has two bedrooms, both full bathrooms, first floor laundry, as well as TWO

    Casey Scott Southern Vermont Realty Group

    1153 King Hill Rd, Readsboro, VT 05350
  • /40

    $179,000

    • Land
    • 8,712 Sq Ft
    • $895,000 per Acre

    10 Partridge Hill, Manchester, VT 05255

    One of the last remaining lots in the exceptional Partridge Hill Association. This beautiful lot is situated to capture wonderful views and abbuts common land and a huge undeveloped land parcel on it's boundaries- offering a private outdoor space. The building envelope benefits from the ability to approach the parcel through the adjacent common land. Underground power and cable at the lot.

    Kim Morgan-Wohler Wohler Realty Group

    10 Partridge Hill, Manchester, VT 05255
  • /34

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,343 Sq Ft

    760 W Mountain Rd, Shaftsbury, VT 05262

    Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

    Kelley Mccarthy Mahar McCarthy Real Estate

    760 W Mountain Rd, Shaftsbury, VT 05262
  • /17

    $160,000

    • Land
    • 2.9 Acres
    • $55,172 per Acre

    Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250

    This scenic undeveloped lot in Sunderland, Vermont, offers an exceptional opportunity to build in a peaceful yet convenient location. Set along a picturesque bike route, the property features level terrain that makes it ideal for easy construction and design flexibility. The land is already cleared, opening up the possibility for lovely mountain views and allowing you to envision your home

    Andy Reed Four Seasons Sotheby's Int'l Realty

    Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250
  • /11

    $299,000

    • 4 Beds
    • 1 Bath
    • 2,156 Sq Ft

    558 Klondike Rd, Stamford, VT 05352

    This is a farmhouse that is currently under construction. Selling as is, with the remaining materials included. It is off grid and was lived in up until last year. Construction started in November 2025. Large barn that used to be a dairy farm. House has 3 woodstoves for heat. 10 cords of wood are included. Very nice setting along side a beautiful brook. 16.5 acres of open and wooded land that is

    Michael Jarvis United Country Real Estate Mike Jarvis Group Inc

    558 Klondike Rd, Stamford, VT 05352
  • /43

    $2,495,000

    Coming Soon
    • 4 Beds
    • 5.5 Baths
    • 4,506 Sq Ft

    3039 Vermont 30, Pawlet, VT 05761

    Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels—over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making

    Carrie Mathews Winhall Real Estate

    3039 Vermont 30, Pawlet, VT 05761
  • /8

    $150,000

    $25K PRICE DROP
    • Land
    • 2.26 Acres
    • $66,372 per Acre

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

    Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

    Tara van de Velde Four Seasons Sotheby's Int'l Realty

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
  • /25

    $975,000

    $275K PRICE DROP
    • 8,888 Sq Ft

    124 Elm St, Bennington, VT 05201

    An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

    Marek Kovac TPW Real Estate

    124 Elm St, Bennington, VT 05201
  • /2

    $2,190,000

    • Land
    • 1.16 Acres
    • $1,887,931 per Acre

    301 Northside Dr, Bennington, VT 05201

    Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

    Paul Carroccio TPW Real Estate

    301 Northside Dr, Bennington, VT 05201

Showing Results 121 - 160, Page 4 of 6

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