582 properties for sale in Bennington town, Bennington County Vermont

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

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

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

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

Flexible In-Town Home with Business and investment Potential A rare in-town opportunity offering both comfortable living and adaptable space. This three-bedroom, two-bath home features a spacious eat-in kitchen, large dining/family room, and a flexible living room that can double as an office or additional bedroom. With a history as a combined home and professional office, the property is well-suited for a small home-based business, complete with ample parking and easy client access. Recent upgrades include a new boiler, hot water heater, and 2026 appliances, plus a brand-new roof on the rear portion of the home. First-floor laundry adds convenience. Live, work, or both-right in the heart of town. OPEN HOUSE - FRIDAY JUNE 26 4:00 p.m. - 5:30 p.m

Nestled in the heart of the Berkshires, this exceptional Williamstown residence offers more than 4,000 square feet of thoughtfully designed living space, featuring 4 spacious bedrooms and 3 bathrooms. Enjoy breathtaking mountain views from the expansive wrap-around deck-an ideal setting for morning coffee, outdoor entertaining, or simply taking in the beauty of every season. Inside, generous living spaces provide the perfect balance of comfort and elegance, making this home equally suited for everyday living or hosting family and friends. Ideally located just minutes from the cultural and recreational attractions that make Williamstown one of New England's most desirable destinations. Within 15 miles, you'll find world-renowned performances at the Clark Art Institute, Williams College, MASS MoCA, and the Williamstown Theatre Festival, along with year-round outdoor adventures including hiking at Mount Greylock, skiing at Jiminy Peak Mountain Resort, and miles of scenic trails, rivers, a

Welcome to the Fox Hill Community and a beautiful modern home tucked away on a private road in Shaftsbury, Vermont offering the perfect blend of privacy, comfort, and stunning Vermont scenery. The home offers 3 bedrooms and 3 bathrooms along with gorgeous mountain views. There is a cozy fireplace in the living room with ample space provided for a family, friends and entertaining. The landscaping is built around the property to accent the outdoors as a beautiful, serene retreat. Whether you're entertaining outdoors, unwinding by the fire, or taking in the breathtaking views, this home offers a lifestyle that's hard to match. Contact me today to schedule your private showing and experience this exceptional property for yourself!

Ideal for those seeking comfort, convenience, and low-maintenance living, this three-bedroom, two-bath condo in Greylock Village offers a thoughtfully designed layout featuring a primary bedroom on the main level. Manufactured wood floors flow throughout most of the home, and the attached garage provides easy, weather-free access. As an end-unit condo, enjoy exceptional privacy with no neighboring driveway, creating a peaceful, tucked-away setting. Central air conditioning and gas heat ensure year-round comfort. While cosmetic updates are needed, the home presents a wonderful opportunity to tailor the space to your taste in a sought-after community known for its ease of living and proximity to Williamstown amenities

Lovely Carriage House in splendid location. Just minutes from prestigious Clark Art Institute with its world-renowned collection of French Impressionist and American Art, and the numerous trails wandering through the meadows and woodlands of its 140 acre campus, and a stone's throw from the outstanding Taconic Golf Club, this charming residence, once part of the Cluett Estate, affords privacy with its 1.4 acres as well as proximity to all Williamstown has to offer. The four bedroom, three and one half bath home features a stellar and spacious living room with large woodburning fireplace, a formal dining room opening to a screened porch overlooking the pleasing grounds, a warm bookcase-lined den with another fireplace, a kitchen with breakfast nook. and stone terraces. With ample room for entertaining family and friends situated on a handsome, considerable parcel close to the center of town, this property offers the feel of country living, but with easy access to all the conveniences of

Set on 2.5 beautiful acres, this inviting Cape-style home offers a wonderful combination of comfortable living space, character, and versatile outbuildings. The primary suite is conveniently located on the main level, with two additional bedrooms and a full bath upstairs. An attached two-car garage provides convenient parking and additional storage. The spacious living room features wide pine floors, built-in cabinetry, a fireplace, and a slider leading to the deck. The dining room continues the charm with wide pine flooring, a large window, and a built-in corner cabinet. Outside, the property offers a large barn with two stalls and an expansive workshop, along with two additional sheds for plenty of storage. There is also the possibility of restoring the property's former pond, adding another attractive feature to the landscape. The kitchen is ready for renovation, offering an opportunity to create a space tailored to your own style and needs. With 2.5 acres, a barn, workshop, attache

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 spacious living rooms! One living room showcases exposed beams, a vaulted wood ceiling, a cozy wood stove, and loft space above which could be perfect for a reading nook, office, or additional guest area. Updates in this home are tasteful, modern and add substantial rustic character. Furnishings are included in the. With two convenient points of entry, the home easily accommodates a dedicated mudroom or simple access directly through the kitchen. This versatile layout allows for one floor living with the expansive space of two bedrooms on the second floor! The property includes a spacious 52' x 35' ba

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, particularly in the two full bathrooms, which now showcase exquisite glazed Italian subway tiles, natural river stones, and other elegant natural surfaces, creating spa-like environments. A recently added Danish wood stove promises cozy evenings and efficient heating, adding to the homes inviting ambiance. One of the three bedrooms has been artfully transformed into a versatile library/office. This beautiful space is perfect for quiet contemplation or remote work, and is designed to gracefully accommodate overnight guests, offering both comfort and privacy. Enjoy the expansive Vermont outdoors fro

Ideal for those seeking comfort, convenience, and low-maintenance living, this three-bedroom, two-bath condo in Greylock Village offers a thoughtfully designed layout featuring a primary bedroom on the main level. Manufactured wood floors flow throughout most of the home, and the attached garage provides easy, weather-free access. As an end-unit condo, enjoy exceptional privacy with no neighboring driveway, creating a peaceful, tucked-away setting. Central air conditioning and gas heat ensure year-round comfort. While cosmetic updates are needed, the home presents a wonderful opportunity to tailor the space to your taste in a sought-after community known for its ease of living and proximity to Williamstown amenities

Discover the charm of this traditional Vermont Camp. Bring your ATV and explore the trails right from your own property. Equipped with a generator and a 300-gallon water holding tank, you'll have access to running water for the kitchen sink and an outdoor shower. Cooking is made easy with a propane stove and lights powered by propane. Rooftop solar panels charge four batteries, which operate the refrigerator, additional lighting, and fans. An outdoor privy is conveniently located just a few steps away. The mudroom provides ample space for drying firewood, organizing supplies, and maintaining the cabin's tidiness. The kitchen boasts generous cabinet storage, a propane/wood stove for cooking, and a large table perfect for sharing meals and stories. The living area is warm and welcoming, featuring a couch, two chairs, and a wood stove for added comfort. There is a queen-sized bed nestled in the front nook, perfect for cozying up with a book or stargazing through the window. There's also a

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.

Welcome to easy Vermont living in this beautifully maintained ranch-style home offering more than 2,000 finished square feet in one of North Bennington's most desirable neighborhoods. Set on a quiet cul-de-sac with lovely mountain views, Harvest Hills offers a wonderful sense of community, including a large neighborhood pond for residents to enjoy. The location is equally appealing; close to the village school, market, restaurants, and the popular Mile Around Woods trail. Inside, a spacious living room with a traditional brick fireplace flows into the bright, open dining and kitchen areas, creating an inviting layout for everyday living and entertaining. The charming kitchen features a breakfast bar, pantry, stainless steel appliances, and abundant natural light. Three comfortable bedrooms and two full baths include a primary bedroom with its own en suite bath. The finished lower level adds valuable flexibility with a generous family room, recreation space, or home office, complemented

Discover the charm of this traditional Vermont Camp. Bring your ATV and explore the trails right from your own property. Equipped with a generator and a 300-gallon water holding tank, you'll have access to running water for the kitchen sink and an outdoor shower. Cooking is made easy with a propane stove and lights powered by propane. Rooftop solar panels charge four batteries, which operate the refrigerator, additional lighting, and fans. An outdoor privy is conveniently located just a few steps away. The mudroom provides ample space for drying firewood, organizing supplies, and maintaining the cabin's tidiness. The kitchen boasts generous cabinet storage, a propane/wood stove for cooking, and a large table perfect for sharing meals and stories. The living area is warm and welcoming, featuring a couch, two chairs, and a wood stove for added comfort. There is a queen-sized bed nestled in the front nook, perfect for cozying up with a book or stargazing through the window. There's also a

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

Discover quintessential Vermont along this idyllic country road embodying peace and serenity. The property features mature trees and a peaceful, quiet location. Close to Lake Shaftsbury State Park and Lake Paran as well as many hiking trails and ski areas. This would make a perfect weekend getaway,, or full-time home. New vinyl siding, a recent metal roof, and newer furnace. Enjoy the convenience of a drive through garage and circular driveway which can easily fit five or six cars when hosting picnics in the large backyard. With high speed internet, working from home is a breeze. The flexible bonus room would make an ideal home office, playroom, guest room, or a future bedroom by adding insulation and a heat source. Wonderful neighborhood full of friendly folk. The tree lined road is perfect for walking, running, biking, and dog walking. Conveniently located halfway between Manchester and Bennington for food, friends, and shopping. It may be small, but it's full of potential!

Discover townhome living in 160 Water St U:24, Williamstown, MA. Cable Mills consists of three former industrial mill buildings restored into beautiful homes featuring 12ft to 16ft tall ceilings, massive windows, and exposed brick and beam, steel and timber throughout, stainless steel appliances, granite countertops, gas-fired ranges, generous closets and in home laundry. Cable Mills offers stunning views of the famed 'Purple Mountains' and the rolling Green River. Homes are one, two or three bedrooms in single level flats, lofts and townhome styles totaling 61 residences. Outdoor spaces including the Outdoor Living Room with a fire pit, grills and seating along the river walk. The main building offers a community lounge, fitness center, interior bike storage, package delivery room, dog wash and on-site professional management. #TownhomesWilliamstownMA #MillBuildingCondo

Set privately on 25.34 acres, this 3BR/2BA contemporary-style home offers expansive views and a peaceful setting just 15 minutes from Bennington. Kitchen with breakfast nook opens out onto a back deck and the spacious living room features a cathedral ceiling and dramatic floor-to-ceiling fieldstone fireplace, creating an impressive focal point and inviting gathering space. First floor also includes a formal dining room and first floor bedroom or office as well as a full bath. On the second floor, the primary suite includes a large bathroom with a walk-in shower and tub, with a layout that may accommodate accessibility needs and a second guest bedroom includes a half bath. Basement-level 2-car garage provides workspace and a dedicated laundry area. The property offers a wonderful combination of privacy, acreage, and convenience, with plenty of room to enjoy nature and and the surrounding landscape. There is ample room for gardening and play! The home needs some repairs and updating, pro

Located a half-mile west of the Williams College campus, this beautifully renovated and meticulously maintained home sits on 0.77 acres overlooking the Village Green and is designed for effortless one-level living. The heart of the home is a spacious, welcoming kitchen featuring a sun filled bay window that allows for plenty of natural light. The living room, anchored by a fireplace, enjoys sweeping views. The formal dining room and flexible den/office provide comfortable spaces for gathering or working from home. Right down the hall you will find 4 bedrooms, 3.5 baths including a large primary bedroom with a full bath. Additional highlights include a two-car garage, a brand-new central air system, a spacious level backyard, with a new back deck, a gorgeous stone front front walkway with a patio, and picturesque views that complete this exceptional property

Enjoy easy Berkshire living in this spacious end-unit condo at Greylock Village! Offering nearly 2,000 sq. ft this 3-bedroom, 2-bath home features soaring ceilings, abundant natural light, a cozy fireplace, first-floor primary bedroom, attached garage, and a functional layout ideal for year-round living or a weekend retreat. Community amenities include a pool, tennis courts, and beautifully maintained grounds. Just minutes from Williams College, The Clark, Williamstown Theatre Festival, MASS MoCA, Mount Greylock, and some of the Berkshires' best hiking, skiing, dining, and cultural attractions. Low-maintenance living in one of Williamstown's most desirable communities!

Set on 2.5 beautiful acres, this inviting Cape-style home offers a wonderful combination of comfortable living space, character, and versatile outbuildings. The primary suite is conveniently located on the main level, with two additional bedrooms and a full bath upstairs. An attached two-car garage provides convenient parking and additional storage. The spacious living room features wide pine floors, built-in cabinetry, a fireplace, and a slider leading to the deck. The dining room continues the charm with wide pine flooring, a large window, and a built-in corner cabinet. Outside, the property offers a large barn with two stalls and an expansive workshop, along with two additional sheds for plenty of storage. There is also the possibility of restoring the property's former pond, adding another attractive feature to the landscape. The kitchen is ready for renovation, offering an opportunity to create a space tailored to your own style and needs. With 2.5 acres, a barn, workshop, attache

Nestled in the center of Williamstown, just steps from Williams College, this stunning two-story Colonial stucco home offers timeless charm and modern comfort. Built in 1907, this 4,100 sq. ft. residence features five spacious bedrooms, three full baths, and one half bath. Set on 1.35 picturesque acres, the property boasts a large post-and-beam barn, a beautifully covered stone patio, and breathtaking western views of the Taconic Mountains. The expansive, level backyard is adorned with mature gardens and majestic old-growth trees, creating a serene and private retreat. Don't miss this rare opportunity-call today for your private showing!