Vintage homes for sale & real estate in Bennington County, VT

Vintage Home for sale in Bennington County, VT:

Charming Antique Farmhouse on 10.9 acres with a large red barn on a quiet town-maintained road needs TLC and finish work. Featuring four bedrooms, one bath, an open kitchen/ dining with solid deck off kitchen. Large fireplace in living room. The current owners have worked hard to make needed updates, including a newer water heater, some new plumbing, removed old plaster and gutted all the interior walls. All the hard work is done, and the designing fun can begin. The current owners are including the new on-site building material. This home has a stone and concrete foundation with interior and exterior access. Needs a good coat of paint on classic exterior clapboards. This home has well-buil

Vintage Home for sale in Bennington County, VT:

Charming 3-bedroom, 1.5-bathroom home set on a generous . 34-acre lot on a quiet street! Recently updated kitchen and bathroom. A spacious mudroom welcomes you as you enter. All three bedrooms are located on the second floor, while the first floor includes the living room, dining room, kitchen, a 3/4 bathroom, and a laundry room. The basement features a dedicated office space along with a convenient half bath. Slider door off the dining room opens up to a large deck with above-ground pool. The backyard offers ample space for entertaining, gardening, BBQs, and play, and it’s partially fenced for added privacy. There’s also a one-car detached garage. This property is perfect as a

Vintage Home for sale in Bennington County, VT:

Completely renovated Cottage Style 3 bed 1 bath home at the edge of town. Located on the Roaring Branch of the Walloomsac river. New heating system, public water and sewer. All new appliances. Just a short walk to the Blue Trail, and the Bennington Recreation Center, All this near public transportation, Mt Anthony Schools. Nothing left to do but move in and enjoy this beautifully renovated home.

Vintage Home for sale in Bennington County, VT:

Welcome to this timeless Victorian gem, located in the heart of East Dorset Village. This elegant home combines historic charm with modern updates, including a fully renovated kitchen featuring stunning soapstone countertops and a luxurious ensuite bathroom off the primary bedroom. Set on a unique 0.57-acre triangle-shaped lot, the property offers a charming stone back patio ideal for outdoor entertaining, a spacious one-car garage with abundant storage, and the potential to create an in-law suite or apartment. The home’s marble foundation and original wood accents reflect its rich history, while newly installed updates like the Jotul wood-burning stove with a brick hearth and back wa

Vintage Home for sale in Bennington County, VT:

Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F. G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4 additional bedrooms, 3 1/2 baths, a formal dining room, large living room as well as front parlor. The large kitchen with a center island, 6 burner gas range opens to a deck patio on one side and the large garage on the other. Most of the wood floors are Brazilian cherry, combined with antique maple upst

Vintage Home for sale in Bennington County, VT:

Cozy 2 bedroom 1 bath just renovated on village lot close to downtown shopping. Hospital, BAT trails, Restaurants, Public transportation near by. This home has everything you need. Pellet stove for those chilly Vt nights. Open floor plan Great side yard and a deck in the back is a great spot for some deck chairs or make it a screen-in.

Vintage Home for sale in Bennington County, VT:

This antique charmer has so much to offer. As one of the oldest homes in Manchester, it is rich in history and character. Although classified as a "condo, " it truly feels like a standalone home. The main house features three bedrooms, two and a half baths, wide board floors, three working fireplaces, a marble patio, and a pleasant backyard with mountain views. Additionally, the attached apartment includes two bedrooms, a spacious kitchen, and a comfortable living room. You can live in one part and rent out the other, or enjoy the entire property as a single-family residence. The options are endless! Showings begin Sunday, 11/24

Vintage Home for sale in Bennington County, VT:

Situated in a lovely neighborhood on a nicely landscaped lot sits this 3 bedroom 2 bath home. 1 car garage under, two paved driveways, back deck and enclosed porch, lower level family room and more! Are you looking for a place to call home? This could be it!

Vintage Home for sale in Bennington County, VT:

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.

Vintage Home for sale in Bennington County, VT:

Farmhouse with ample acreage in the Vermont corner-town of Pownal! This well-maintained 1850 construction has old New England charm, while offering easy access to Bennington VT, North Adams MA, and Albany NY, well situated in its own quaint town. Take in mild Vermont summers and brilliantly colored autumn from the back deck, then curl up by the fireplace throughout the winter. Generously proportioned with four bedrooms, this is a cozy home from which to explore all that Vermont has to offer, not least of which the 59+ acres that you’ll own. Inquire today! Open House Sunday, November 24th 11AM-1PM.

Vintage Home for sale in Bennington County, VT:

If you're looking to relocate to Southern Vermont and would enjoy a country setting with a spacious yard, this recently remodeled 2 bedroom home might be right for you! Close to town and to numerous attractions such as Mass Moca, the Clark Art and Williams College as well as dining and entertainment; outdoor activities such as skiing, snowmobiling, hiking, boating - are all nearby. This house was stripped to the frame and remodeled in 2022 so much of it is like new. Come on up and take a look - this may be what you're looking for!

Vintage Home for sale in Bennington County, VT:

In town, but tucked away on a 3.5 acre tree filled lot. A beautiful open yard with plenty of space for outdoor activities. This 1952 Center Hall Colonial is in excellent condition, loaded with charm. First floor encompasses a charming kitchen, dining room, living room, powder room, and study (or another overflow bedroom). Head to the 2nd floor to 4 corner bedrooms and a full bath. Outside you'll find a detached garage with room for one car parking. Don't hesitate on this well loved home. It won't last.

Vintage Home for sale in Bennington County, VT:

Almost there! This owner has taken a traditional farmhouse and transformed it into an amazing home full of style and grace. There are many ways to consider this home. .. over 3500 square feet of single family living with 4 bedrooms (or even 5) and 3 baths. .. live on one floor, AIR B & B all or part of the other floor. .. .rent both levels and use as a vacation home on off seasons. The kitchen is large enough for a bevy of cooks with an island for bread or candy making. The heart of the house, you can be a part of the party while you whip up some fab eats. Tile and glass and reactive bidets make the baths sparkle and inviting. The 2nd floor main bedroom sports a mini kitchen, balcony

Vintage Home for sale in Bennington County, VT:

Discover timeless charm blended with modern comfort in this enchanting 4-bedroom, 2-bath home nestled amidst Vermont's scenic beauty. This residence boasts a newly painted exterior with a classic wrap-around porch that invites you to enjoy leisurely moments soaking in East Dorset's small town lifestyle complete with restored marble sidewalks.   Step inside to a welcoming parlor where wood flooring adds warmth & character throughout. The heart of the home features an updated kitchen, perfect for culinary exploits while entertaining guests or preparing family meals. The living area with a stamped copper ceiling allows for generous seating, a formal dining room, and f

Vintage Home for sale in Bennington County, VT:

This historical Italianate two-story property, built in 1865 by the Bennington Manufacturing Company, offers a unique opportunity for both commercial and residential use. Originally constructed as the Bennington Mill's Company Store. The building has been zoned for two purposes. The first floor presents a prime commercial space, perfect for a variety of businesses. Upstairs, you'll find two potential residential units, offering a versatile living arrangement or additional income potential. The slate roof has been fully repaired and renovated, ensuring its durability and longevity. This architectural gem shares many historical similarities with the 1865 Mill Building at the Holden-Leonard Co

Vintage Home for sale in Bennington County, VT:

Charming 2-3 bedroom, 1-bath home nestled on a peaceful country lot just outside of town. First floor bedroom and bathroom, town water and sewer for convenience and versatility. Property has an oversized 2-car garage with unfinished bonus space upstairs ready to customize. This property features new flooring, updated structural repairs, and the serene beauty of a babbling brook across the street. A small but awesome enclosed front porch will become a favorite spot to sit out and enjoy the seasons or a place to leave your boots.

Vintage Home for sale in Bennington County, VT:

What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging? This amazing building has so many possibilities. With the exterior restoration just completed and some very attractive new interior spaces for living including the fully equipped kitchen, delightful bedroom, walk-in closet, and three quarter bath, and second floor bedroom suite, one can move right in while you imagine how you might like to ch

Vintage Home for sale in Bennington County, VT:

Location, location! Just two blocks from the SVMC healthcare campus, this spacious home is ideally situated on Putnam Street in a beloved Village Residential neighborhood. This four-bedroom, three-bath home is currently configured with an in-law suite/apartment on the second floor with exterior access. The permitted second-floor apartment offers versatility with one bathroom and a kitchen—currently leased and income-producing! The covered front Porch offers views of the setting sun. The paved driveway with ample off-street parking offers easy entry to the side door. A spacious, level backyard is partially fenced, offering privacy and a shed to hold your outdoor storage needs. Main flo

Vintage Home for sale in Bennington County, VT:

This home is steeped in history and the location is outstanding! Nestled on a quiet street within walking distance to Burr and Burton, golf, superb dining, Equinox Pond and area trails. Enjoy simple walks around the neighborhood. A small stream runs along the property for you to dip your feet in on hot summer days! Built as a Sears home that arrived via railroad with high ceilings and located in what was then known as the Orvis suburb. A large private deck for entertaining or simply relaxing with your morning coffee. This two-story expanded colonial offers spacious rooms with an interesting floor plan that can be adapted to suit different needs. There is ample storage and a detached two car

Vintage Home for sale in Bennington County, VT:

A Vermont home with a perfect blend and timeless appeal of a historic home and the conveniences of modern living. This charming home has endless possibilities, from restroration to a blank canvas to make it exactly the home you have always wanted. The home features a first-floor washer and dryer conveniently located in a spacious mudroom—perfect for keeping things tidy after spending time outdoors. Through the mudroom you will enter into the kitchen area and the large living room. There are two other large rooms downstairs along with an office and a full updated bathroom. There is a large bedroom upstairs and additional bedrooms, one with a direct access to the spacious storage area a

Vintage Home for sale in Bennington County, VT:

Welcome to Hidden Ponds Farm!!! Nestled amidst 40 sprawling acres, this historic early 1800's post and beam converted barn is a rare gem combining rustic charm with modern comforts. The property is highlighted by a stunning 1,000-foot hand-placed stone wall, two picturesque ponds, and two orchards offering seasonal beauty and fresh fruit. The expansive outdoor space also features a hot tub, propane fire-pit and an in-ground pool perfect for summer relaxation, along with a 90 foot deck complete with retractable awnings for shaded outdoor gatherings. For those seeking ample storage or hobby space, the property includes a separate 4-bay garage with a second-story loft for additional storage n

Vintage Home for sale in Bennington County, VT:

Experience the quintessential Vermont lifestyle at the historic Nickerson-Jewett farm. Only 5 minutes to Bennington attractions and amenities and 15 minutes to Williamstown, MA. This appealing country home is located on a town maintained dead-end road. Privately nestled on 134.46 acres of scenic beauty, the charming 4 bedroom, 2.5 bath mid nineteenth century farmstead includes a well-preserved vernacular farmhouse and agricultural outbuildings. The property boasts open fields, wooded areas, fruit trees, perennial gardens, a babbling brook, ponds, walking and riding trails. It is the perfect setting to observe nature as well as the glorious Vermont’s glorious changing of the seasons. T

Vintage Home for sale in Bennington County, VT:

Located on historic 7a in Shaftsbury, Vermont. House is listed as a 2 bedroom, but there is an office on the main floor should you need additional multi use space for guests. This property is ready for the next new owner to continue making the updates that have been started. Look at these beautiful, refinished hardwood floors! Don't miss an opportunity to own this solid home with large backyard, fenced in garden area, attached one car garage with additional separate detached two car garage for all your vehicles and toys! Situated on 6 acres of land, zoned for both commercial and residential use! Come take a look, don't let this one pass by you!

Vintage Home for sale in Bennington County, VT:

Nice quite in town location. Beautiful yard. House presently set up as a two family. Easily converted back to single family. Cross listed as a two family MLS #5008408

Vintage Home for sale in Bennington County, VT:

Manchester colonial on 0.22 acres located in close proximity to all downtown amenities. The property overall is very well maintained. Recent improvements include: (4) four new mini-splits, updated furnace with on demand hot water. Many fine features including: air conditioning, hardwood flooring, tile bathrooms, propane radiator heat. The property offers a gracious covered front porch, and an enclosed rear porch suitable for a mudroom in the winter months. The first floor consists of entry, half bath, living room, office, and bedroom. The second floor offers a combination living room/kitchen, two bedrooms, and a full bath. The kitchen is equipted with refrigerator, electric range, and micro

Vintage Home for sale in Bennington County, VT:

Discover the charm of this spacious Cape-style home nestled on a tranquil, town-maintained road. Conveniently close to North Adams for shopping and amenities, this 3-bedroom, 2-bath residence offers a host of appealing features. The large eat-in kitchen, accessed via a generous mudroom, is perfect for family meals and entertaining, with an adjacent dining room for added space. An ample-sized office/den on the first floor offers a great focus space, ideal for remote workers. The oversized living room will easily accommodate gatherings with family and friends. The center stairs lead to three bedrooms and a full bath. The large basement includes a workspace area, and a newer Buderus oil furnac

Vintage Home for sale in Bennington County, VT:

RARE Vermont Live & Work opportunity to become the third owner in nearly 50 years of the chocolate barn, a local landmark known for its commitment to high-quality ingredients and exceptional customer service. Fully turnkey with proven track records of success and growth provides fantastic opportunities for new ownership stepping in to continue the momentum. Strategically positioned along Historic Route 7a, the business attracts steady streams of locals and tourists year-round. Years of commitment results in premium products sold in-house retail and numerous high-profile wholesale accounts (restaurants, inns, country stores). Sale includes fully operational retail chocolate/ice-cream/

Vintage Home for sale in Bennington County, VT:

Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould Pleissner lived at the Plaza in New York City and summered here while her husband, celebrated artist Ogden Pleissner, used the barn as his studio—his works now hang at the Met, Shelburne Museum and in private collections. The 1790s farmhouse and 1820s barn underwent extensive renovations by Boston ar

Vintage Home for sale in Bennington County, VT:

This unique property offers an excellent investment opportunity with two separate buildings on-site. The front building hosts a well-established H & R Block commercial space, providing a steady and reliable stream of income. Additionally, there are two residential units, both of which are currently rented, ensuring immediate cash flow. Behind the front building, a full-sized house exists! It currently occupied by long-term tenants. Enjoy stable, long-term rental income with minimal turnover history. The property is just a couple of blocks from the heart of Bennington in a section great for foot traffic and conveniently located within walking distance from many restaurants, stores and m

Vintage Home for sale in Bennington County, VT:

* * IDEAL FOR A LIVE-IN INVESTOR OR DEVELOPERS LOOKING TO GROW THEIR INVESTMENT * * Take advantage of this huge multifamily development opportunity in the heart of Manchester! There is an existing triplex on the property with beautiful mountain views. This building consists of basement with coin op laundry and individual storage locations for tenants and owner. 1st floor consists of a 3 bedroom/1 bath unit with a front & side deck. 2nd floor has 2: 1 bed/ 1 bath units. Separate entrances for each unit. Mountain view from each unit. The property is zoned for 8 units total, and we have plans for an additional 5-unit build. Everything is on Town water/sewer - reach out for SPIR and Y

Vintage Home for sale in Bennington County, VT:

101 Morgan Street is a historic home located on a corner lot with good size side yard. This 2 story, 4 bedroom, 1 bath Bennington home has great character featuring a Dutch front door, enclosed front porch, and beautiful bay window. Property has an eat-in kitchen, dinning room, laundry room with washer and dryer, living room, basement, and den! Enjoy being conveniently located downtown near great dining and shopping. This home’s forced hot air heating and metal roof was redone in 2020.

Vintage Home for sale in Bennington County, VT:

Beautiful in-town, 3-bedroom, 2-bathroom home is completely turn-key and ready to be your Vermont home! Perfectly situated in a sought-after neighborhood near the hospital, shops, and Bennington's many Main Street parades and festivals, it offers just the ideal blend of convenience and charm. So many recent upgrades and renovations, including a brand-new roof, furnace, significant tree removal for an improved mountain view, and the added convenience of a larger kitchen and main-floor laundry. Several options for home office space if needed, including a charming second-floor enclosed balcony or beautiful first floor sun-room.  But the true showstopper is the incredible 3rd-floor attic,

Vintage Home for sale in Bennington County, VT:

Welcome to Peaceful Pines, your cottage in the woods near the entrance to the Green Mountain National Forest. Charming two-bedroom cottage/camp was lovingly maintained, updated and used year round over the years. Key updates include a completely rebuilt chimney and masonry work, a wood stove ( fill baseboard heat too) to take the chill out of those fall and winter evenings, new T11 siding, a newer roof, and a private back deck with potential views of Glastonbury Mountain and beyond. The property also features an outdoor shower, a large shed, a drilled well, and a concrete block foundation. The lot offers plenty of space for outdoor activities and relaxation on +/- . 8 acres. Inside, the coz

Vintage Home for sale in Bennington County, VT:

Nestled on a nearly one-acre lot near the heart of Bennington you'll find this secluded property. This home has great potential with its layout and versatile spaces, with the benefit of first floor living if desired. The home features three bedrooms, one and a half baths. Additional rooms could transform this to a six bedroom. Under the home are two garage spaces, and plently of storage room. Selling the home as-is so that you can transform into your own personalized haven. This property provides a comfortable space that can allow you the freedom to unleash your creativity and customize to your unique tastes and preferences. With cosmetic updates, you can build equity over time as you trans