Properties Near 121 Fillmore Street Bennington, VT

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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!
Welcome to your ideal in-town residence! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of space, comfort, and convenience—located just a few blocks from downtown dining, shops and festivals. Step through the enclosed breezeway from your attached garage to find a bright and inviting floor plan featuring a generously sized living room and formal dining room with beautiful hardwood floors, the kitchen has easy access to a patio overlooking a nice backyard and the hardwood floors continue in not one, but two, first floor bedrooms. The first floor is rounded out with a full bathroom. Upstairs are another two spacious bedrooms with tons of closet space and another full bathroom. The partially finished basement is a true standout, boasting a large recreational space perfect for game nights, movie marathons, or home workouts. There's also a full bar—ideal for entertaining friends and family! Newer windows, boiler and hot water heater. Don’t miss your chance to own this versatile and well-appointed home in a great neighborhood!
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!
Welcome to this newly renovated Cape nestled in a desirable downtown Bennington neighborhood. This spacious home offers four bedrooms and two full bathrooms, including a first floor primary suite for added comfort and convenience. The brand new galley kitchen features gorgeous cabinetry, tile flooring, and energy efficient appliances perfect for modern living. A dedicated dining room provides a great space for family meals, and there's a flexible bonus room that can serve as a home office or even a fifth bedroom if needed. Outside, enjoy fresh landscaping, two paved parking spaces, and a backyard shed for all your storage needs. Located in a walkable neighborhood with easy access to grocery shops, restaurants, and commuter routes this home is perfect blend of charm, functionality, and location.
Enchanting, delightful, magical... this lovely c. 1920 village home is all of that and more! 3BR/2BA home has beautiful hardwood floors and a cook's kitchen with Corian countertops and not one but two pantries! Dining room, living room with electric fireplace, office/study that could also be a first floor bedroom and updated 3/4 bath round out the first floor. Upstairs there is the primary bedroom, two guest bedrooms and full bath with clawfoot tub. One car garage is accessed by a breezeway and the back yard is private and nicely landscaped! All within walking distance to all that downtown Bennington has to offer; shops, eateries, the library and more!
Motivated seller of this beautifully ranch home on a dead-end road boasts 4 Bedroom. Enjoy the warmth of the sunroom during the day. The living room centered in the middle of the house has plenty of space to spread out and enjoy the pellet stove insert with a brick hearth on those cool nights. Locally crafted Cushman Style cabinet in the dining area with delightful wood cabinets in the kitchen. Enjoy the views of Mount Anthony from the concrete stamped patio for outdoor dining and relaxing. The corner lot is located on a dead-end street, This home is located within walking distance to the hospital, the Bennington Area Trail System, Close to public transportation, Downtown shopping. Southwestern Supervisory Union show this as being part of the Monument Elementary School Assignment. New Boiler, Upgraded insulation, new plumbing, Too many improvement to mention here
Charming Two-Bedroom Home in Convenient Bennington Location Welcome to this inviting two-bedroom, one full bath home offering spacious and versatile living areas. The main floor features a large living room perfect for relaxing or entertaining, a formal dining room, and an eat-in kitchen with a door leading out to a generous deck-ideal for outdoor gatherings. The lower level boasts a large family room with a cozy spot ready for a woodstove, plus an additional room perfect for a home office, media room, or guest space. An oversized one-car garage provides ample storage space above, complementing the fenced backyard and handy storage shed. Conveniently located in Bennington, Vermont, this property offers both comfort and practicality with easy access to local amenities. Don't miss the opportunity to make this well-maintained home yours!
Charming and cozy 2-Bedroom, 2-Bath Ranch with expansion potential in a quiet, sought-after neighborhood just minutes from downtown and local amenities. With its inviting single-level layout, beautiful hardwood floors, and spacious great room, this home offers comfortable living with timeless appeal. The full walk-out basement adds incredible potential—already partially finished with a bathroom started, it's ready to be transformed into an in-law apartment, additional living space, or a custom retreat to suit your needs. Recent updates include a brand-new roof in 2024 and a high-efficiency Buderus boiler. Outside, enjoy a picturesque yard perfect for relaxing or entertaining, plus a convenient 1-car garage. A wonderful opportunity in a fantastic location—come see the potential for yourself!
2BR/2BA Mid Century Modern brick ranch is solidly built and cozy! Step into the large living room with hardwood floors and electric fireplace. Eat-in kitchen is bright and nostalgic with corner windows and sink and period appropriate cabinetry. Arched doorways lead throughout the home to the two bedrooms and the full bath with soaking tub. On the lower level, there is a carpeted family room and additional room for office, gym, etc. as well as a 3/4 bath and dedicated laundry space. One-car garage and nice level back yard. Located on the outskirts of town, you are just a stone's throw to stores, restaurants, schools and all things Bennington!
A unique South Street property offering income potential, located just outside the heart of downtown Bennington and Hospital. Three bedrooms, two bathrooms, including a first-floor bedroom with two additional bedrooms on the second floor. An attached oversized garage can accommodate four to five vehicles, and a separate three-bay garage currently generates $450 per month in rental income, an excellent opportunity to offset expenses. The seller is offering Sellers concession towards the buyer's closing costs! Don't miss this versatile property that has even more income potential.
Classic Bennington home on a quiet street with a beautiful yard and a detached barn/garage. First floor kitchen with dining area, laundry room, and a full bath, plus a living room and family room that could also be a first floor bedroom. Upstairs there are three bedrooms and a play room with a storage closet. Enjoy your morning coffee on the covered porch, and take a walk to downtown shops.
Step into timeless elegance with this charming 1940 American Foursquare home. Many gorgeous features have been preserved from the elegant crystal light fixture to the stunning original woodwork. Each detail speaks to the skilled artisanship of the era. The classic design offers spacious living and a welcoming atmosphere, perfect for both every day life and entertaining. The main floor boasts a spacious family room addition with ample windows and maple flooring, 3/4 bath, and first floor laundry. The formal dining room flows seamlessly into the living room with pellet stove. The interior was completely redone in the last decade with very recent renovations including old wallpaper removal and fresh paint in the living/dining areas and kitchen. The stunning entry way and staircase is everything you want from an antique home. There is even a fully enclosed front porch for enjoying the approaching warm weather. Upstairs you will find three bedrooms with original hardwood floors and a full bath. The basement is dry and has ample storage space. The lot is easy to maintain with a walkable location minutes away from local parks, shops, restaurants, and public transportation. Head a few minutes more up RT 9 and you’ll find all the outdoor recreation and beautiful scenery that Vermont is known for. This lovely home blends classic design with modern conveniences, making it a must-see for those who appreciate quality craftsmanship and historic charm. Don’t miss out on owning this gem!
NEW!NEW!NEW! This completely renovated Cozy 2 bedroom cottage was taken back to the studs and redone with New wiring, New plumbing, New heating system, New Bathroom. Everything here is new and ready to just move in and enjoy easy living. Located on village lot with a great side yard for family cook outs. There is a deck in the back ready to be transformed to a screened porch. Just a short walk to the Bennington Area Trail System is a short walk for mountain biking or just to hike Mount Anthony. Close local Restaurants, Public transportation, Hospital and downtown shopping.
Located in a sought-after area, this Tri-level townhouse style condo is situated close to Main Street shops, bars, and restaurants, as well as the hospital, rec center, neighborhood markets, and the bus station. The first floor boasts an open floor plan with a unique kitchen that retains its original charm. Highlights include a center brick chimney, island w/ breakfast bar, quartz and butcher block countertops, a tile backsplash, built-ins, and marble floors. The main living area also includes a large living room and dining room with engineered hardwood flooring throughout, an updated half bath, and a foyer. The upstairs has three bedrooms, an updated full bath, and engineered flooring throughout. A walk-up attic provides ample additional storage space. The partially finished lower level includes a rec room or office, a laundry room, and a utility room with a newer heating system (installed in 2020) and a newer oil tank (2022) and 200amp electric panel . Outside, you can enjoy relaxing on the front porch or in the cozy backyard. The property also includes a shared detached garage. Move in ready!
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.
Walking distance to Bennington College! Perfect for college housing. The property has a scenic path alongside the river so students can walk or bike to school without having to be on the road. Currently used as a single family home or can easily be converted to a duplex. This 3 bedroom North Bennington home is set in a quiet location with only ten homes in the little neighborhood with dead end street. Very convenient to town but feels like you are out in the country. The public water and sewer is a nice bonus. Boiler is just three months old and there is a gas line to the house. New roof in 2022. Kitchen has an antique wood stove. The property has lovely landscaping with plenty of space for gardens. Just a short 1.3 mile stroll to North Bennington restaurants, library, and post office and 4 miles to downtown Bennington with Albany Airport just under an hour away. Lake Paran is just 1.5 miles away for swimming, kayaking, or enjoying the beach.
Perched high on Imperial Avenue, this delightful Cape-style home is brimming with character, charm, and endless potential. Gorgeous wood floors and abundant natural light set the tone for a warm, inviting space that’s ready for your personal touch. The main level offers a comfortable flow between the living room, dining area, and kitchen—all boasting sweeping views of downtown Bennington and the surrounding hills. Upstairs, you’ll find three cozy bedrooms and a spacious full bathroom, perfect for restful nights and relaxed mornings. Ideal for low-maintenance living, the home also features a partially finished basement room which can be used as a home office, gym, or creative space, plus ample utility and storage areas. Enjoy the manageable yard with a quaint side patio space for outdoor dining, and take in the neighborhood from your impressive front porch, an ideal spot for morning coffee or evening sunsets. Located just a short walk from downtown shops, restaurants, and cafes, as well as scenic walking trails, this special home offers the perfect blend of convenience and tranquility.

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