Properties Near 1385 North Bennington Road Bennington, VT

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Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres. Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and rear parlors—ideal as a den, family room, or library. Rich in character, the home showcases gleaming hardwood floors, intricate pocket doors, custom built-ins, and exquisite architectural details throughout. The kitchen is perfectly positioned for gatherings and everyday living, while a large mudroom with laundry adds modern-day convenience. Two versatile bonus rooms provide options for office space, a hobby area, or additional guest accommodations. Outside, the 2.6-acre lot offers mature trees, a gracious sitting porch, and a classic New England barn—ideal for storage, a workshop, or future creative use. This is a rare opportunity to own a distinguished property with space, style, and substance. Schedule your private showing today—this is truly a must-see home!
Step into this beautiful 1930s classic home, filled with character and endless possibilities. This home offers three bedrooms, one bathroom, and a layout that seamlessly combines classic details with comfortable living spaces. The heart of the home is the large dining area, perfect for hosting gatherings or enjoying quiet family meals. Adjacent, you will find a spacious living room with a fireplace and abundant natural light. In addition, a sun-filled family room includes built-in bookshelves and cabinets. The kitchen features a convenient walk-in pantry, adding both practicality and storage to its charm. The primary bedroom is a standout feature, offering ample space and an alcove perfect for a home office, nursery, or private retreat. Beautiful hardwood floors run throughout, adding warmth and character. Located in a desirable Bennington neighborhood in close proximity to the downtown, this home is ideal for anyone seeking a convenient and vibrant location. Bring your vision and make this timeless home your own!
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!
Step into timeless charm with this beautifully maintained 1910 antique home offering 4 bedrooms and 2 full baths on a nearly a full acre. Enjoy the perfect blend of historic character and modern updates, including a great working kitchen that any chef would enjoy, plenty of counter space, efficient layout, and everything within easy reach, perfect for creating homemade meals. The original hardwood floors, and a welcoming mudroom that keeps the clutter at bay. The first floor bedroom has direct access to the a full bath ideal for guests or single level living. Upstairs, you'll find a bright office space and convenient laundry right outside the bedrooms. The home is filled with natural light and features multiple inviting spaces, including a cozy living room with a pellet stove and an additional family room for relaxed gatherings. Outdoor living is just as impressive with an above ground pool, fenced yard for your pets, and a custom built dog house. A charming enclosed porch adds year round entertaining space, and shed offers great storage. Located near shopping, scenic covered bridges, and all the best of Vermont living! OPEN HOUSE SUNDAY JUNE 1, 2025 12-2PM
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.
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.
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 beautifully maintained 3-bedroom, 1.25-bath home nestled on a corner lot in Bennington. This inviting property blends classic charm with thoughtful updates, offering comfort and style both inside and out. Step into the spacious kitchen featuring stunning wood cabinetry, granite countertops, and a functional island with a bar sink-perfect for entertaining or everyday living. The cozy living room offers a warm retreat with a fireplace and elegant French doors. Additional highlights include a convenient first-floor laundry area, a covered side porch ideal for relaxing, large deck with mountain views, and a layout designed for easy living. Enjoy year-round comfort with a newer furnace and added insulation throughout the home. Don't miss the opportunity to own this gem in the heart of Bennington!
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.
Welcome to the charming ranch home nestled in a desirable and quiet neighborhood! This beautifully maintained three bedroom home offers comfort, style, and fantastic features throughout. The recently renovated full bathroom is a true highlight, featuring a stunning fully tiled walk in shower complete with a built in bench. Enjoy the comfort and efficiency of a brand new mini split, and cook with ease in the spacious, updated kitchen perfectly designed with views of the backyard and pool area, making it a natural gathering space. The bright and welcoming living room features newly installed carpet, while additional gleaming hardwood floors add warmth and charm throughout the home. Each bedroom offers excellent closet space with beautiful natural light. This home is ideal for those seeking the ease of single living, with everything you need on the main floor. Or, if you're looking for more space, the partially finished basement offers incredible potential perfect for creating a family room, game room, home office, or entertainment space. Whether you want to enjoy the simplicity of one floor living or take advantage of the extra square footage downstairs, the choice is yours. Situated in a wonderful neighborhood known for its walkability and charm, this home also boasts a beautiful inground pool and a well maintained yard perfect for relaxing, entertaining, and enjoying time with family and friends.
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!
Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and modern feel to this central gathering space. The kitchen flows effortlessly into a large dining room or office and living room. Upstairs, you'll find two generously sized bedrooms, including a private primary suite with its own newly renovated bathroom. Both bathrooms have been thoughtfully updated for a more contemporary, stylish look. For year-round comfort, this home now boasts newly installed heat pumps, ensuring efficient heating and cooling no matter the season. Plus, there’s plenty of storage space, with room for your seasonal items in the back of the house, and even a dedicated workshop area to fuel your hobbies. The house is surrounded by beautifully landscaped garden beds that not only add curb appeal but also provide a peaceful, outdoor retreat. And for those who love a walkable lifestyle, you’re just a short stroll from the best of what Bennington has to offer. Showings start 5/17/25.
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!
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.
Energy efficient 3 Bed, 2 Bath with character and awesome updates in downtown Bennington. Wrap-around front porch welcomes you inside this classic New England Colonial. Highly sought after "first floor living" with a bedroom, full bath and laundry all on the main level... along with the living room, dining room and kitchen. Second floor has two bedrooms with walk-in closets and full bath with claw foot tub and hand shower. Under foot you'll be walking on new Pergo wood flooring in the front rooms, hexagon vinyl tiles in the kitchen, vinyl plank in laundry and bathrooms, and carpet upstairs. Kitchen has a walk-in pantry for tons of storage, island for prep with butcher block counters, open shelving with a beautiful arabesque backsplash, and Stainless Steel appliances. Three mini splits for central air in the summer and heat in the winter, plus an oil-fired boiler for primary or back-up heat. Seller is keeping the pellet stove, but you can BYO or install a wood stove or just enjoy more space in that room when it's gone. Spray foam insulation throughout basement makes it VERY cheap to heat, plus offers dry storage. No flood history; seller's flood insurance is only $500/yr. Step out to the fully fenced backyard with deck and gardens; enjoy the delightful sound of children playing at nearby elementary schools. Neighborhood grocery store just a few steps away for convenience... or walk a bit farther for Stewart's ice cream or downtown's fabulous restaurants and events.
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!
Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown! Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort. From the moment you arrive, you're greeted by the cobblestone driveway leading to the wraparound porch with pillars adorned with regal lion heads, perfect for tea, tales, and twilight daydreams. Inside you’ll find Dragons carved into the stair railings, an open living room, formal dining room, and a sunny breakfast nook tucked in the heart of the kitchen. The fireplace glows with Bennington pottery tiles around the hearth, and a vintage tub pours water from a sculpted fish faucet, offering a splash of whimsy. Discover a rare delight below: a basement projector booth and private children’s puppet theater waiting to be finished. Fantasy meets function in this home Whether you're sipping espresso in the garden or hosting dinner parties in the grand dining room, this home feels like a European escape — without ever leaving town.

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