Properties Near 321 Chester Knoll Drive Bennington, VT

Brand new construction, getting the finishing touches now, This three bedroom two bath cape style home is energy efficient and up to the newest Vermont energy codes. On demand hot water and efficient heat system. This home Has an under house heated garage plus a bonus walkout room in the lower level. Quote is available for buyers interested in finishing that. Not only do you get brand new construction, but you have an option for one level living with living room, kitchen, dining, laundry, bedroom, and full bath all on one level. Upstairs has two large bedrooms and another full bath as well as closet storage. Glass slider from the kitchen and dining area goes out to a brand new deck off the back of the home. Enjoy the convenience of living in the Chester Knoll neighborhood is that plowing, landscaping, and trash is all included in the HOA fees, as well as having access to Trails throughout the property. Tucked away from the busy roads, but close to downtown and the hospital, this is a treasured spot to call home. Be the first to live in this Vermont home!

Contemporary style 3BR/2BA home in a lovely residential neighborhood not far from downtown Bennington! Kitchen has been updated with granite counters and stainless appliances and opens onto sunny dining area. Living room includes brick hearth with woodstove and shiplap ceiling, there is first floor laundry and a three-quarter bath as well as an expansive family room with lots of natural light. Plus there is a fully screened porch of the living room that will allow you to enjoy the privacy of the back yard. Second level is newly carpeted and includes the primary bedroom (with direct access to the shared full bath with vinyl plank flooring) and two guest bedrooms. Propane heat, metal roof, electric hot water. Level 1.41 acre lot offers all kinds of outdoor opportunities from gardening to volleyball!

Struggling with housing affordability? This could be the solution! Originally built as a single family home in 1920, but currently arranged as 3 units, so you can take over all the space, or rent some and enjoy the cash flow! Two apartments have great tenants who are moving this summer, so both the upstairs and downstairs will be available soon. Third unit known as "The Octopus Garden" is an Airbnb guest favorite so you could ride the wave of this popular short-term rental. An easy conversion back to single family would literally mean opening a couple of doors... then the main level would have 3 bedrooms and 2 bathrooms, a mudroom, kitchen and living room... and upstairs would have a bright family room, larger kitchen, 1 bedroom and a full bathroom with claw foot tub and laundry. Don't need two kitchens? Remove one to create another bedroom, office or dining room. Need an in-law suite for guests or family? This has it. Work-from-home professional or small business owner? Zoning has many allowed uses, including office and retail. Recent energy audit + updated utilities: new 200 amp panel, new boiler, and central air on the first floor! Ask for the list of improvements, floor plans and videos. Beautifully renovated spaces, two new decks overlooking the deep backyard and gardens, plus a covered front porch. The 0.41 acre lot is very narrow, offering parking for 6+ cars with partial fences and a stone wall for boundaries. This is a rare and special opportunity!

Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find hardwood floors throughout and an inviting living room centered around a classic fireplace. The living space is bathed in natural light, thanks to five sets of French doors that create a beautiful flow between rooms and invite the outdoors in. The sunroom, located at the back of the home, offers a peaceful retreat year-round, while additional French doors open onto a screened porch-perfect for summer evenings and quiet mornings. Other highlights include a detached garage, automatic starting generator. and a manageable yet private lot just steps from the village center. With its graceful details and prime location, this home is a true Bennington treasure.

Charming renovated cape with mountain views! Perched high on Grandview Street on a spacious and level lot, this beautifully renovated Cape-style home offers comfort, style, and lovely views of Mount Anthony and beyond. Step inside to a bright and welcoming first floor, where an open-concept layout easily accommodates both living and dining areas, enhanced by large windows that fill the space with natural light. The fully updated kitchen is a true delight, featuring elegant porcelain tile flooring, rich cherry cabinetry, gleaming granite countertops, and brand-new stainless steel appliances. A convenient first-floor bedroom and full bath make single-level living an option. Upstairs you’ll find two additional bedrooms and a brand-new half bath, both enjoying panoramic views of Bennington and the surrounding landscape. The clean, dry basement provides ample storage or potential for additional finished space—ideal for a recreation room, home office, or studio. Outside, enjoy warm summer evenings on the rear deck overlooking the backyard—perfect for grilling, entertaining, or simply relaxing. With thoughtful updates throughout, this home offers truly turnkey living. Located within easy walking distance to downtown Bennington’s shops, restaurants, the hospital, library, and nearby walking trails, this is a rare find that blends convenience with quiet charm. Move right in and start living your best Vermont life!