Properties Near 82 Oakes Street Bennington, VT

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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!
Opportunity awaits with this well-built and meticulously maintained 3-bedroom, 2-bath home nestled on a rare and highly desirable 1.84-acre flat lot in the peaceful countryside—just a short drive to town amenities, shops, and schools, this property features town water, a new roof, nearly new boiler and an attached two-car garage. Set back from the road, this property offers space, privacy, and incredible potential for those looking to update or expand. Inside, the freshly painted main level of the home features a functional floor plan with living and dining rooms, three generous bedrooms, and a functional kitchen. The full bath on this main level connects to the primary bedroom. There is a partially finished walkout basement that could be used for a separate suite, home-based business (buyer to verify) or rec room. While the interior reflects a more vintage style, it’s well-maintained, and ready for your personal touch or full renovation. Outside, enjoy the wide-open space ideal for gardening and outdoor entertaining. The roof is just a year young, and the vinyl and brick exterior make for low maintenance. Whether you're a first-time buyer, investor, or someone looking for land to create your dream homestead, this property offers endless possibilities in a prime location. Don't miss your chance to own a country retreat with room to grow—schedule your showing today!
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.
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.
A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings. Chester Knoll provides an established, welcoming neighborhood where you can embrace a truly low-maintenance lifestyle. A low HOA fee covers essential services including plowing, landscaping, and trash removal. Residents also benefit from convenient access to a network of picturesque trails winding throughout the property, perfect for leisurely strolls or invigorating outdoor activity. Enjoy the serene ambiance from the enclosed porch, where the gentle flow of a nearby tributary provides a soothing soundtrack. Tucked away from bustling roads yet remarkably close to downtown Bennington and the hospital, this treasured spot offers the ideal blend of tranquility and accessibility.
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.
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!
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!
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.
Welcome to this adorable one-level 3-bedroom, 1-bath bungalow, perfect for comfortable and efficient living. This home offers a cozy and inviting atmosphere with all living spaces on a single level-ideal for anyone seeking ease and accessibility. Inside, enjoy the warmth and character of a woodstove, perfect for creating a cozy ambiance during cooler months while helping keep energy costs low. The open layout provides a seamless flow between rooms, with natural light brightening every corner. Step outside to find a detached, oversized 2-car garage- heated and ideal for vehicles, a workshop, or additional storage above. This charming home combines practical features with timeless appeal-don’t miss your chance to make it yours!
Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.
Welcome to Unit #1 at Norton Potters, a quaint and quiet townhouse community nestled in a lovely neighborhood setting. This end-unit two-bedroom home is full of character and natural light, offering a peaceful retreat with a deck that overlooks a serene stream. The main level features a spacious living room, dining area, kitchen with a generous pantry, a convenient half bath, and laundry area. Upstairs, you’ll find a bright guest bedroom, a full bathroom, and a primary bedroom with double closets. There’s also a bonus room ideal for a home office or nursery. Don’t miss this rare opportunity to own a delightful home in a peaceful, well-maintained community close to everything Bennington has to offer.

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