Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary suite on the main level provide convenience and flexibility. Upstairs, you’ll find two generous bedrooms, a full bath, and a cozy den area perfect for reading or quiet work. Step outside to enjoy the large slate patio framed by handsome stacked stone walls or unwind on the private Trex deck overlooking the .75-acre lot. A rare blend of charm and space just minutes from the historic village of Old Bennington.
Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized kitchen is perfection for entertaining and for spending time with family and friends. The living room invites a space for conversation, a cozy fire during the chilly Vermont evenings, or simply relaxing taking in the divine views at sunset. More casually, the family room offers exposed beams, vaulted ceilings and abundance of natural light. A formal dining room is strategic to the kitchen for holidays and family gatherings. The second floor boasts three bedrooms and two bathrooms, while the third bath is on the first level for convenience. And have I mentioned the renovated space above the garage? Wow! Breathe in the fresh air, take a walk up a country road and hunker down for the most genuine, spectacular sunsets. This is the type of special property that you will not want to miss.
If you’ve been searching for a home in Vermont and nothing has quite captured what you’re looking for, this is your chance to create it. Set on a quiet, paved road in one of Bennington’s most desirable neighborhoods, this property offers that rare balance: close to everything, yet removed enough to feel peaceful. Morning coffee with mountain views. Evening walks with direct access to the Bennington Area Trail System. A quick drive to SVMC, Bennington College, and downtown—yet home still feels like your own retreat. Albany International Airport is just an hour away when you need it. A thoughtfully designed single-level home is currently envisioned, centered around open, connected living spaces with easy access to the outdoors, a covered front porch, and an attached garage. But this is not a one-size-fits-all build—and that’s the point. This is your chance to shape how your home lives. Prefer a different layout? A more modern aesthetic? A classic Colonial with all the bedrooms upstairs? Need to reconfigure the garage—or expand the footprint? We can adjust, redesign, or start from scratch. Every decision, from the big picture to the smallest details, is an opportunity to create a home that reflects your lifestyle—not someone else’s. You’ll work directly with a trusted local builder with over 40 years of experience, guiding you through a process that is collaborative, thoughtful, and grounded in craftsmanship. The result isn’t just a new house—it’s a home designed with intention, built for how you actually want to live. Offered as a land and construction package. A rare opportunity to create something truly your own in a location that’s becoming harder to find. Seller is a Vermont licensed real estate broker.
Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque—yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great room anchored by an impressive floor-to-ceiling fireplace, with a loft above that overlooks the space and adds architectural interest. The thoughtfully designed layout includes three bedrooms, highlighted by an incredibly spacious primary suite featuring a walk-in closet and a luxurious en suite bath with soaking tub and double vanities. The main level also offers two additional bedrooms, a full bath, and convenient first-floor laundry. A bright breakfast nook provides the perfect spot to start your day, while the back deck overlooks the lush gardens, creating an ideal setting for outdoor entertaining or quiet relaxation. The inviting front sitting porch, complete with a charming fish pond, enhances the home's peaceful appeal. Additional features include an attached oversized two-car garage, a home office, large workshop and sweeping mountain views that complete this exceptional property. A rare opportunity to enjoy privacy, natural beauty, and timeless craftsmanship in one remarkable setting.
If you’ve been searching for a home in Vermont and nothing has quite captured what you’re looking for, this is your chance to create it. Set on a quiet, paved road in one of Bennington’s most desirable neighborhoods, this property offers that rare balance: close to everything, yet removed enough to feel peaceful. Morning coffee with mountain views. Evening walks with direct access to the Bennington Area Trail System. A quick drive to SVMC, Bennington College, and downtown—yet home still feels like your own retreat. Albany International Airport is just an hour away when you need it. A thoughtfully designed single-level home is currently envisioned, centered around open, connected living spaces with easy access to the outdoors and covered porches both front and rear. But this is not a one-size-fits-all build—and that’s the point. This is your chance to shape how your home lives. Prefer a different layout? A more modern aesthetic? A classic Colonial with all the bedrooms upstairs? Need an attached garage—or prefer to keep it simple, with the option to add one later? We can adjust, redesign, or start from scratch. Every decision, from the big picture to the smallest details, is an opportunity to create a home that reflects your lifestyle—not someone else’s. You’ll work directly with a trusted local builder with over 40 years of experience, guiding you through a process that is collaborative, thoughtful, and grounded in craftsmanship. The result isn’t just a new house—it’s a home designed with intention, built for how you actually want to live. Offered as a land and construction package. A rare opportunity to create something truly your own in a location that’s becoming harder to find. Seller is a Vermont licensed real estate broker.
Beautiful 3-bedroom, 3-bath home offering stunning views from a spacious two-tier deck-perfect for relaxing or entertaining. Designed for comfortable main-level living, the home features a generous primary suite and an open, light-filled living room with a dramatic wall of windows that captures the surrounding scenery. Warm and inviting, the home includes two gas fireplaces, gleaming wood floors, and a low-maintenance lifestyle ideal for year-round enjoyment. The kitchen is appointed with granite countertops and a convenient slider leading directly to the deck-perfect for easy outdoor grilling. The walk-out lower level offers exceptional flexibility, featuring a large family room, cozy library area, cedar closet, and an expansive craft room or office that could easily be converted into an additional bedroom. With its layout and private access, the lower level presents great potential for an in-law apartment. A standout feature is the 10x26 workshop, complete with a dust collection system already in place—ideal for woodworking or hobbyists. The home is equipped with central air, 200-amp electrical service and is wired for a generator, providing added convenience and peace of mind. Additional highlights include a partially fenced yard and an attached two-car garage, completing this well-rounded and inviting property.
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