390 houses for sale in Bennington town, Bennington County Vermont

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

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 four first-floor units each feature private back decks overlooking a beautiful, expansive backyard, adding to tenant appeal. With 12 off-street parking spaces, convenience is key. Ideally located within walking distance to the Village of North Bennington, residents can easily enjoy local restaurants, shops, and scenic walking trails. A truly rare opportunity for investors seeking both character and strong rental potential!

Opportunity meets lifestyle in this affordable ranch-style home perfectly positioned next to The Spruces-Williamstown's beloved off-leash dog park and walking trail. If you're looking for a budget-friendly entry into the highly desirable Williamstown market, a home within the school district, or a smart investment with strong community appeal, this is it. Just 2 minutes to Williams College and The Clark Art Institute, and 5 minutes to MASS MoCA, offering world-class art and culture nearby. Directly adjacent to The Spruces, enjoy immediate access to scenic trails and a vibrant community space loved by walkers, runners, dog owners, and families alike. Being sold as-is, the home features hardwood floors, high ceilings, and a functional layout. The family room is down to the studs and ready for your finishing touches following a resolved plumbing issue. Update - Brand new subfloor and flooring currently being installed in the sunroom! Bring your creativity, and vision to life-this is an ex

Welcome to 1111 Old Depot Road in Shaftsbury, Vermont, where country living and natural beauty come together on approximately four scenic acres. This inviting four-bedroom, two-full-bath ranch-style home offers a rare opportunity to enjoy privacy, natural beauty, and convenient access to one of Southern Vermont's most beloved recreational destinations. Set on a spacious parcel with room to relax, garden, and explore, the property provides a peaceful setting surrounded by mature trees and open space. The home's comfortable layout offers easy single-level living, making it ideal as a primary residence, vacation getaway, or investment property. A true highlight of the property is its proximity to the Lake Shaftsbury area, where residents can enjoy swimming, fishing, kayaking, paddleboarding, hiking, and year-round outdoor recreation just moments away. Whether you're enjoying a quiet morning surrounded by nature, spending the afternoon on the water, or gathering with family and friends aro

Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and welcoming space for relaxing or entertaining. The flexible floor plan provides three bedrooms plus an additional room that can easily serve as a fourth bedroom, home office, or hobby space. The walkout unfinished basement offers endless possibilities for future expansion, storage, or a workshop. Outside, you'll find an attached two-car garage along with a separate bonus garage, providing ample space for vehicles, recreational equipment, or additional storage. Set well back from the road, the property's 16.96 acres offer room to explore, garden, or simply enjoy the peace and beauty of Vermont. The home

If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the owners in the '80s. The 3300+ square feet of living area on the upper level and another 3300+ on the lower level ready to be finished. As you can see, the lower level has plenty of windows and will be very flexible space to use. The two-car garage is attached to the house. From there, into the mudroom. The kitchen is very generous. There's room for your breakfast table, a couple of easy chairs and a love seat, and the woodstove will make this a cozy country kitchen to be. This is a 'cooks dream'. The commercial range will make your friends jealous, as will the pantry and stained glass on the upper

Wonderful little getaway for some 'EZ' living-be one with nature with all the essentials in place! It's common to see wildlife in this rural setting, making it perfect to create your ideal Vermont retreat. Nestled among the trees, you'll relish the peaceful ambiance and natural beauty that surrounds you, offering a true sense of escape from the everyday hustle. A tidy, compact getaway with a propane stove and lighting adds both convenience and comfort, letting you unwind in rustic charm. The solar system provides extra illumination and powers a ceiling fan, ensuring the cabin stays bright and comfortable even on warmer days. The wood stove heats the cabin, you have everything you need for a comfortable stay, and there's an outhouse out back for added convenience. This property is perfectly positioned for Vermont country enjoyment. The shed has enough storage for those toys, making it easy to bring along your favorite outdoor gear. The queen-size Murphy bed in the front nook offers a co

Tucked into a private wooded setting on the outskirts of town, this distinctive 3-bedroom, 1.5-bath Adirondack-inspired chalet blends rustic character, flexible living space, and an exceptional connection to the outdoors. Its steep roofline, front balcony, exposed beams, and metal roof give the home memorable architectural presence, while the peaceful surroundings create a true retreat from the everyday. Inside, hardwood floors and dark ceiling beams add warmth and character to the main living and dining area, where a propane stove set against a brick hearth creates a cozy focal point. Brand-new windows throughout bring in abundant natural light, complemented by new French doors that open directly to the deck. The efficient kitchen offers generous cabinetry and slate-finish appliances, all included. An adjacent unfinished mudroom provides an opportunity to create a convenient entry and additional storage. A main-level bedroom and full bath offer the flexibility of one-floor living, com

Tucked away in a peaceful, private setting off scenic Oblong Rd and overlooking a meadow with limited distant views of Mt. Greylock, this converted barn redesigned in 1994 by local architect Anne Mccallum,offers an inviting year-round retreat. The cathedral ceiling greatroom showcases exposed, hand-pegged beams from the original 1948 barn structure, creating a warm and timeless gathering space. An expansive deck to the east extends the living area outdoors, ideal for relaxing or dining while taking in the surrounding landscape. The first floor is an open floor plan with kitchen, adjacent comfortable living room and dining area. This level includes 2 comfortably sized bedrooms and a full bath, while the entire upper level is devoted to the primary suite. A full walkout basement provides exceptional flexibilty-a studio, exercise room, workshop or simply generous storage. In addition is a detached garage with space for two cars and adequate storage on the second level.Set on 2.8 acres, th

Escape to the rustic charm of this beautiful 5 bedroom, 2.5 bath log cabin nestled on 2 peaceful acres in the highly desirable town of Shaftsbury. From the moment you step inside, you'll fall in love with the warm log features throughout, exposed beam ceilings, and the cozy fireplace that anchors the inviting living room. The charming country kitchen flows into a dedicated dining room, creating the perfect space for gatherings, holidays, and quiet evenings at home. A finished basement with spacious family room offers even more room to spread out, entertain, or relax. Outside, enjoy the privacy and tranquility of country living from your brand new deck while still being conveniently located just 15 minutes from downtown Bennington. Complete with a 2-car garage and surrounded by the beauty of nature, this property is the rustic retreat every log cabin lover dreams about

The Dexter Road Farmhouse, Circa 1800 In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write Stopping by the Woods on a Snowy Evening. Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region. Tucked away at the end of a peaceful, tree-lined town road, the property is ideally suited as a second home, creative retreat, or year-round residence. Lovingly cared for by the same family for over 70 years, the home retains much of its original character and craftsmanship. Wide pine floors, original moldings, classic woodwork, traditional wall and ceiling boards, and a gracious entrance hall create a warm and authentic farmhouse atmosphere. Set on approximately 40 acres with a picturesque skating pond, the property offers abundant space to explore, garden, walk, and enjoy the pastoral surroundings. Writer

This charming, beautifully updated Cape sits on a sprawling 2-acre lot in a highly sought-after section of Shaftsbury, offering breathtaking panoramic mountain views. Boasting character and gleaming hardwood floors throughout. The first floor features a large living room with built-in bookshelves and cozy wood stove, a primary bedroom, full bath, and spacious country kitchen with granite countertops, island with storage and seating, recessed lighting, and adjacent eat-in dining area. There's a practical mudroom off the main entrance, which leads to a bright 14' x 22' multi-purpose sunroom with cathedral ceilings, perfect for an office, crafting, home gym, or entertaining guests. Upstairs, you'll find two generously sized bedrooms with beautiful cherry and oak wood floors and an updated full bath. The full basement with concrete floors and insulated walls provides excellent storage space and utilities. Step outside and take in sweeping mountain views that frame the property in natural b

Wonderful little getaway for some 'EZ' living-be one with nature with all the essentials in place! It's common to see wildlife in this rural setting, making it perfect to create your ideal Vermont retreat. Nestled among the trees, you'll relish the peaceful ambiance and natural beauty that surrounds you, offering a true sense of escape from the everyday hustle. A tidy, compact getaway with a propane stove and lighting adds both convenience and comfort, letting you unwind in rustic charm. The solar system provides extra illumination and powers a ceiling fan, ensuring the cabin stays bright and comfortable even on warmer days. The wood stove heats the cabin, you have everything you need for a comfortable stay, and there's an outhouse out back for added convenience. This property is perfectly positioned for Vermont country enjoyment. The shed has enough storage for those toys, making it easy to bring along your favorite outdoor gear. The queen-size Murphy bed in the front nook offers a co

Tucked away on a peaceful country road in Shaftsbury, this 2-bedroom, 2-bath contemporary ranch offers the perfect balance of privacy and convenience; just 10 minutes to Bennington. Set on 1.5 acres, the home features easy one-level living with an open, light-filled layout. The heart of the home is the bright, sunny kitchen with ample workspace and modern finishes. The spacious primary suite includes a private ensuite bath and a generous walk-in closet, while a comfortable guest bedroom is paired with a full bath, ideal for visitors or flexible use. Enjoy indoor/outdoor living with a wrap-around deck that is perfect for relaxing or entertaining. A versatile entry space, currently used as a mudroom, offers excellent potential to be converted into a charming 3-season porch. Additional highlights include a dedicated laundry room and an oversized detached two-car garage that is fully heated for year-round use allowing space for hobbies, or extra storage. Surrounded by a tranquil country se

Own a piece of Williamstown history with this beautifully preserved Greek Revival modern farmhouse, set along the Green River on just under 20 picturesque acres. This exceptional property offers a rare combination of historic charm and modern comfort, with ample acreage for farming or livestock, ponds, barns, an in-ground pool, and more. The main residence features 5 bedrooms and 4 bathrooms, while the attached guest house offers 2 bedrooms and 2 bathrooms, providing flexibility for extended family, guests, or multi-generational living. Step inside this timeless home to discover thoughtful modern upgrades designed for everyday living. A spacious mudroom at the rear entrance keeps daily life organized, while the stunning kitchen-complete with stainless steel appliances, granite countertop and cozy fireplace overlooks the side porch, screened room, and sweeping pastoral views. The first floor offers two additional living spaces, each with its own fireplace and French doors that open dire

Gorgeous, renovated Colonial offering exceptional flexibility, thoughtful design, and timeless charm. This beautifully updated property features a spacious main residence along with a stunning addition that includes a full in-law suite and a private studio above ideal for guests, extended family, a home office, or potential rental income. Solar panels installed above the garage power efficient mini-split systems, and a Tesla Powerwall provides added energy independence and peace of mind. The main house offers four bedrooms, a fabulous chef's kitchen with quality finishes and generous workspace, and warm, inviting living areas filled with abundant natural light. Magnificent views of Mount Anthony and the sweeping five-acre meadow below can be enjoyed from the kitchen, dining room, living room, and screened porch-where wildlife is often part of the daily landscape. A new large enclosed porch further expands the living space, creating the perfect setting to relax or entertain year-round.

Barns, Brook and Beautiful Living Uniquely spanning the Williamstown, MA and Pownal, VT state line, this inviting property combines New England charm with exceptional flexibility. The expanded 3,500 sq ft home offers 4 bedrooms and 2 full baths, including an option for a first-floor bedroom. Warm, connected living spaces include a stone-fireplaced family room, open kitchen and dining area, a cozy tavern room with wet bar, and a shaded patio for summer enjoyment. The 3.4-acre Vermont parcel features Broad Brook along its boundary plus two outstanding outbuildings: a 30'*40' insulated and finished barn with office and 12' ceilings, and a 30'*50' three-bay garage with 12' rafter clearance-ideal for vehicles, equipment, hobbies, or future conversion. With the house on 0.6 acres in MA and t

Welcome to 1111 Old Depot Road in Shaftsbury, Vermont, where country living and natural beauty come together on approximately four scenic acres. This inviting four-bedroom, two-full-bath ranch-style home offers a rare opportunity to enjoy privacy, natural beauty, and convenient access to one of Southern Vermont's most beloved recreational destinations. Set on a spacious parcel with room to relax, garden, and explore, the property provides a peaceful setting surrounded by mature trees and open space. The home's comfortable layout offers easy single-level living, making it ideal as a primary residence, vacation getaway, or investment property. A true highlight of the property is its proximity to the Lake Shaftsbury area, where residents can enjoy swimming, fishing, kayaking, paddleboarding, hiking, and year-round outdoor recreation just moments away. Whether you're enjoying a quiet morning surrounded by nature, spending the afternoon on the water, or gathering with family and friends aro

This charming, beautifully updated Cape sits on a sprawling 2-acre lot in a highly sought-after section of Shaftsbury, offering breathtaking panoramic mountain views. Boasting character and gleaming hardwood floors throughout. The first floor features a large living room with built-in bookshelves and cozy wood stove, a primary bedroom, full bath, and spacious country kitchen with granite countertops, island with storage and seating, recessed lighting, and adjacent eat-in dining area. There's a practical mudroom off the main entrance, which leads to a bright 14' x 22' multi-purpose sunroom with cathedral ceilings, perfect for an office, crafting, home gym, or entertaining guests. Upstairs, you'll find two generously sized bedrooms with beautiful cherry and oak wood floors and an updated full bath. The full basement with concrete floors and insulated walls provides excellent storage space and utilities. Step outside and take in sweeping mountain views that frame the property in natural b