Properties Near 61 Autumn Acres Road Bennington, VT

Charming Historic Home with Garden, Barn & Flexible Living Spaces This beautiful 100+ year-old home offers over 3,400 sq. ft. of warmth, character, and room to grow. Flooded with natural light, this home on 2+ acres has three sunny upstairs bedrooms and three baths. In addition to a large living room and full dining room, the main floor has a laundry/mudroom and front and rear parlors that can serve as additional bedrooms, guest rooms, or cozy living spaces. The second floor features its own 2-bedroom, 1-bath apartment—perfect for multi-generational living, hosting guests, or generating extra income. Mature trees, wrap-around porches, a sunny lawn, and an ample garden offer space for planting, play, and relaxation, while a sturdy two-story barn provides endless possibilities—storage, workshop, studio, or hobby space. There is also separately entranced area at the back of the house that can provide office space. The house has many original details, including pocket doors, hardware, and woodwork, as well as double-pane windows throughout. This exceptional property, located in the North Bennington school district, offers a rare combination of history, space, and flexibility. Come and experience the warmth and potential of this one-of-a-kind home.

Completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an additional bedroom. Outside you'll find a large front yard that has been partially fenced, a large covered, wrapping deck for entertaining and outdoor dining and a dog fenced area. Great location across the road from a calm river. This home is larger than it appears from the road. A must see home.

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 renovated kitchen and bathroom, complemented by new flooring throughout the home. The dining room features a sliding glass door that opens to a spacious back deck, perfect for outdoor dining and relaxing. A covered front porch adds classic New England charm and a welcoming touch. With a large attached garage offering plenty of storage and workspace, this home is as practical as it is inviting. Whether you're enjoying the peaceful surroundings or entertaining guests, this home provides comfort, style, and a true sense of place in a friendly, walkable neighborhood. Don’t miss this North Bennington gem—schedule your showing today!

Set well back from the road, this mid-century modern home emphasizes simple lines, an indoor-outdoor connection, and panoramic views. The main level centers on an open living/dining/kitchen area anchored by a fireplace and oversized windows that overlook the pond and rolling landscape beyond. The primary suite on this level provides private comfort. A second-floor bedroom offers a rare upper-level retreat complete with a private bath - perfect for guests, teenagers, or a dedicated workspace. Though the home’s layout and setting are outstanding, it needs thoughtful updating: kitchens and baths could be refreshed, finishes modernized, and mechanicals upgraded to improve energy efficiency. With cosmetic work and systems improvements, this property will be transformed into a stylish, comfortable showpiece that honors its mid-century heritage. This property delivers the best of both worlds - architectural interest and a peaceful natural setting. The pond and views create an immediate sense of escape, while the four-bedroom layout and three baths make it practical for full-time living or a vacation retreat. For buyers who appreciate mid-century lines and want to add modern amenities, this is an inspired canvas.

This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level features a newly renovated kitchen and bathroom, adding modern comfort to this historic property. With five bedrooms throughout, there's more than enough space to accommodate guests or create your ideal home layout. Keep it as a turnkey short-term rental, or easily convert it into a large single family residence with plenty of room to spread out. The property sits on a lovely lot with a private yard, perfect for outdoor entertaining, plus a one car garage that could be brought back to full use with some TLC. Located near Bennington's local events, shops, and attractions, this home is a smart opportunity whether you're investing, relocating, or dreaming of a versatile live/work space. Opportunities like this don't come along often. Call today to schedule a private showing and explore the potential.

WOW CHECK OUT THIS Country Cutie on the edge of town. The home has been updated while keeping the period Charm. Large level nicely landscaped yard enclosed by hedges. The lager living room has a fireplace with insert and lots of built-ins. The walkout basement has a large room that has been used as a bedroom with a stone fireplace and a half bath in the heated workshop area.

Welcome home to this charming single level ranch in a peaceful, friendly neighborhood where neighbors still wave hello and lend a cup of sugar. This home offers easy single-level living with three bedrooms, one full bath, and first floor laundry. Step inside to discover beautiful hardwood floors throughout most of the home, currently covered with carpeting that can easily be removed no nails or tack strips to worry about. The layout provides a warm, inviting flow from room to room, perfect for everyday living or entertaining. You'll love cozying up by the working wood stove on a chilly Vermont evenings, and the best part the wood for this winter is already stacked and ready to go! Enjoy mountain views from the property, giving you a daily reminder of Vermont’s natural beauty. Relax on the enclosed porch or the covered front porch, both ideal spots to unwind and take in the scenery. Outside, the fully fenced-in yard, detached two-car garage, and additional shed offer space for storage, projects, or play. Nestled in a desirable, well-kept neighborhood, this home combines comfort, convenience, and that true Vermont charm everyone is looking for.

Cute as a button! This charming one-owner home is the perfect opportunity for a first-time homebuyer or for those looking to downsize! The main level features a welcoming layout with bright living spaces and plenty of natural light. The eat-in kitchen flows seamlessly into the living area. There are two spacious bedrooms, lots of closet space and a full bathroom. The basement level features a two-car garage and incredible potential for a bonus space with plumbing available for a second bathroom. Enjoy the back deck overlooking the private backyard, all in a quiet, established neighborhood just a few moments from downtown. Why pay rent?!

Discover this beautifully updated home set directly on the Walloomsac River, offering 123 feet of peaceful river frontage. Enjoy fishing right from your own backyard, hosting gatherings by the water, or simply relaxing to the soothing sounds of the flowing river. Ideally located within walking distance of Main Street, the Rec Center (featuring a gym, sauna, indoor pool, and tennis and basketball courts), and the local bus station, this home combines in-town convenience with tranquil riverside living.  Originally designed as a two-family house, it has been thoughtfully converted into a spacious single-family residence. The main level features a kitchen with built-ins and new flooring, a large living room, an additional Family room, an updated full bath, a first-floor bedroom with a double closet, and two mudrooms. New vinyl plank flooring extends throughout the main level. Upstairs, you’ll find a generous primary bedroom with a walk-in closet, two additional bedrooms with one having a private staircase leading outdoors. The upper level showcases warm wood floors throughout and an updated bathroom. The large, clean basement offers two heating systems and two oil tanks—ideal for stocking up when fuel prices drop. Additional highlights include low-maintenance vinyl siding, replacement windows, town water and sewer, and fresh professional paint throughout.  This house is truly move in condition!

This 4 bedroom cape is located on a dead end street in a desirable neighborhood within the village of Shaftsbury. The updated kitchen has a small island and is open to the dining area. The living room has hardwood floors, gas fire place and built-ins along one wall. There is a washer and dryer located on the first floor in the entry hall and a full bath also on this level. There are two bedrooms on the first floor, one of which could be used as an office or den space. One bedroom on the second floor has built in dresser and both bedrooms have access to under eave storage. There is also a 3/4 bath on the second floor. The yard is fenced in and not only level lot but has raised beds for gardening. The 1-car garage is attached with a breezeway to the house as well as a separate area for a workshop. The basement is partially finished with two bonus rooms.

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, Downtown Bennington.

Welcome to 50 Ledgely Drive, a charming and well-cared-for home located in one of Shaftsbury’s smaller neighborhoods. This 2 bedroom, 1 bath home is ideal for first-time buyers, downsizers, or anyone looking for a more manageable space with potential to grow. Solidly built and lovingly maintained over the years, this home offers great bones and a warm, inviting feel throughout. The efficient floor plan provides comfortable living and dining areas, a functional kitchen, and 2 bedrooms with abundant natural light. Breezeway connects the house to the attached 3-car garage. With a few timely updates and a bit of TLC, you can easily make this home your own while building equity over time. Set on a corner lot, the property offers added privacy, extra yard space, and plenty of potential for gardening, outdoor entertaining, or simply enjoying the quiet surroundings. The neighborhood is known for its close proximity to the village and community feel. Just a short distance from Shaftsbury Elementary School and the country store, providing convenience and Vermont charm for daily essentials with a friendly, small-town vibe. All offers must be submitted by 4pm 9/22.

Huge Price Reduction. Enjoy the charm and comfort of this beautifully renovated home, ideally nestled in the heart of Bennington. As you arrive, you'll be greeted by a spacious front porch, perfect for relaxation, entertaining, and enjoying cool breezes. This property has undergone a complete transformation from a two-family to a stunning single-family home. It now offers convenient one-floor living. The first floor boasts a brand-new kitchen with butcher block countertops, first-floor laundry, and new, gleaming hardwood floors throughout. You'll find a large first-floor bedroom and a second bedroom, which would also make a great office space, along with an updated bathroom. The second floor offers two additional bedrooms, including a large master suite with an oversized walk-in closet/sitting room, and an updated bath. The home also features a 3-year-old high-efficiency on demand tankless boiler/water heater, Electrical updated with new panel, new plumbing, an oversized garage/barn attached in the rear, and a side porch for easy access. Situated close to Main Street shops and restaurants, offering exceptional convenience. The property is also serviced by town water and town sewer. It's only a few minutes' stroll to the Elementary and High schools, the Rec Center with a full gym and pool, and the bus station, adding further convenience for commuters. Truly move in condition!

This 3-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and convenience. Set on a generous .35-acre lot, the property features a large living room ideal for gatherings, and a spacious kitchen with plenty of room for cooking and entertaining. Enjoy the convenience of a large detached garage, plus a private outdoor space that's perfect for gardening, playing, or relaxing evenings. Located just a short walk to the local country store and from Shaftsbury Elementary School, this home is perfectly situated for everyday convenience in a peaceful setting. Whether you're starting a family, downsizing, or just looking for more room to breathe, this property offers a fantastic opportunity to enjoy small-town living with all the right features.

A classic Victorian home in the village of Shaftsbury is waiting for your imagination and perseverance to bring this once charming residence back to its original luster. Each room has its own character from dining room built-ins, shelving throughout the entire house to display your precious treasures, living room fireplace for those cozy winter nights, exposed brick and extra large eat-in kitchen. There are four bedrooms on the second floor, one is an office. The back entrance brings you into a very spacious mudroom, always a plus for Vermont's ever changing seasons. A stairway that leads to the cellar from the back entrance was once an apartment with a kitchenette and full bathroom.There are two sources of heat, an oil furnace and a wood furnace. The grounds need some reshaping and in-ground pool could be a plus for the hot summer days and entertaining. Sidewalks for safe walking, close to the post office, Shaftsbury Elementary School and the Shaftsbury Country Store. Easy drive to shopping and restaurants in either Bennington, or Manchester. Three hours to NYC and Boston, one hour to Albany International airport for travel. Come and take a look, I'd love to show you! House is being sold "AS IS"

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.

Lovely ranch home with 2 bedrooms on a great level lot. Come see all the improvements including but not limited to, new flooring, new kitchen counter, new stove, new dishwasher, fresh paint throughout, new boiler, new oil tank, and new light fixtures. Come see what else this home has to offer.