Old Bennington Village Town Page

Old Bennington is a unique village of historic homes from the Revolutionary, Antebellum and Victorian eras.  They remain the finest collection of these architectural styles in all of Vermont.  The dominant architectural style is Federal and homes built later, into the 20th century also favored this style. The village is one mile west of the town of Bennington and has its own governance.  It was designated a National Historic District in 1984. 

Directly across from the village green lies a remarkable cemetery of Revolutionary War heroes as well as other notables including Robert Frost and his immediate family. 

The Old First Church was restored in 1937 using the original plans of its master builder and architect, Lavius Fillmore. It was the first church in Vermont.  The first minister of this Congregational Church was Rev. Jedidiah Dewey and his home still remains in the village along with the homes of many other early settlers and leaders of this village.

Chartered in 1749 and settled in 1761, we owe a debt of gratitude to Captain Samuel Robinson who discovered Bennington.  Governor Benning Wentworth of New Hampshire had been charged by King George to settle this territory.  Mistaking the Hoosac River for the Hudson River, Robinson upon returning with his soldiers from his exploration of “The Wilderness” known today as Vermont secured the first grant given and named after the governor in 1749. Endowed with natural beauty, located on a wide plateau west of the town Bennington, Old Bennington has become a remarkable place to own a home.

When the post office officially moved in 1848 to what is now known as Bennington, the original settlement became Old Bennington.  Over time Old Bennington evolved into a residential village as businesses moved to the larger community of Bennington.  The village remains largely residential but three small businesses remain as well as an elementary school that is within the regional school system.  The Bennington Museum, also in the Village features a collection of Grandma Moses’s paintings and broad array of items significant to the local history. 

One outstanding example of bygone days is reflected in the Walloomsac Inn which was originally built by Jedidiah Dewey’s son Elijah in 1771 and still stands, though closed to the public.   Know originally as The Dewey Tavern until after Elijah’s death in 1818, guests before and after the republic was founded included Benjamin Franklin, Thomas Jefferson and James Madison among other notables of the time. The grandest feature in the village is The Bennington Battle Monument commemorating The Battle of Bennington, a significant turning point in The Revolutionary War.

There are some 82 residences mostly on 2+ acres of land with sidewalks shaded by tall trees. We highly encourage you to get a feel for the village and its history by walking from the Old First Church and cemetery up Monument Avenue, stopping to read the commemorative plaques recognizing our heroes in the Revolutionary War and ending at the Bennington Battle Monument.

We are close to the many cultural and year round recreational activities throughout the region.  If you cherish history and elegant historic and vintage homes you must put this village on your list of possibilities.

21 West Road Bennington VT 05201

MLS Number 4851427

  • Commercial
  • Village Old Bennington
  • Year Built 1913
  • Acreage 11.1

This landmark inn has a stellar reputation as a premier lodging and dining venue that spans 60 years. Each of the 11 guest rooms is creatively decorated and attractively furnished with an artistic flair for color and texture in fabrics and wall coatings. 7 of the guest rooms have gas or wood-burning fireplaces. The present owners have extensively renovated the inn over the past 16 years taking great care to maintain the integrity of the inn's historic architectural features. The result is an exceptional blending of vintage architectural features and contemporary guest room and bath design. Manager's apartment onsite. Owners' 7 bedroom Greek Revival home located across the road is available for purchase separately. This inn has a long, successful track record of being a reliably strong financial performer with an annualized occupancy rate over 60%. Currently operated as a high end Bed & Breakfast Inn, a successful, fine dining restaurant was operated onsite for decades. All licenses, fixtures and equipment are in place to reopen the restaurant should new owners choose to maximize the use of this superb facility.

Listed by Pamela Long of East Coast Inn Brokers

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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21 West Road Bennington VT 05201

Bennington, VT21 West Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4849646

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bedrooms 12
  • Bathroom 16

This exquisitely appointed circa 1913 mansion is privately situated in the prestigious Historic District of Old Bennington amidst 11 acres of parklike grounds. The mansion has been masterfully restored and updated with an eye to preserving its period architectural features. The first floor features an intimate living room with wet bar and wood-burning fireplace, a spacious formal dining room with wood-burning fireplace, a stunning conservatory with brick floor and two walls of divided glass windows and French doors. This property boasts a fully equipped commercial grade kitchen with a spacious footprint. A great space to create your dream kitchen. The 7 of the 12 bedrooms have gas or wood-burning fireplaces and individually controlled heat. En suite bathrooms are tastefully updated. An in-law apartment and 2 cottage suites offer the opportunity for multi-generational living. The property has operated as a highly successful inn for decades providing new owners the opportunity to continue the lucrative inn business or to rent the cottage suites and in-law apartment for supplemental income. Large out-building has possibility to be an oversized, two-car garage with structural upgrades. The stylish furnishings are included in the sale subject to a short list of exclusions. This property can also be purchased together with the Greek Revival home located directly across the road. See MLS #4840013.

Listed by Pamela Long of East Coast Inn Brokers

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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17 Fairview Street Bennington VT 05201

Bennington, VT17 Fairview Street

Price$695,000

Est. Mortgage: $/month

MLS Number 4854130

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

C. 1845 Greek Revival originally built by Deacon (of the Old First Church) John Robinson. This home is graciously appointed and meticulously cared for with views of the Monument and the mountains. The 7.2 acres include mature apple trees, stone walls, a small pond, a barn and gorgeous gardens. The home features a bright living room with a fireplace, wood floors and a wall of windows to take in the views. Down the hallway is a sizable dining room for entertaining with views to the south. The kitchen has updated appliances and has a great Butler's pantry for all the extras. Large mudroom off the kitchen which flows into the family room that has a wood stove insert. A private office to work from home and a half bath. Upstairs has five bedrooms and 3 baths including a private master suite. Attached two car garage, large screened in porch and deck. The carriage barn includes a workshop area, storage for the tractor and studio space above. This property is a must see!!!

Listed by Kelley McCarthy of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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88 Monument Avenue Bennington VT 05201

Bennington, VT88 Monument Avenue

Price$580,000

Est. Mortgage: $/month

MLS Number 4843499

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Built by Pliny Dewey in the early 1800's, the Son of the First Pastor of the Old First Church. This beautiful Center Hall Colonial has been tastefully restored retaining many original features including 4 fireplaces, one of which came from the State Arms Tavern once located on the site of The Bennington Monument. Stunning and tastefully appointed kitchen with soap stone countertops and Butler's pantry with prep sink. Dining room boasts beautiful wainscoting repurposed from the original pew doors of The Old First Church. Offering 4 large bedrooms (2 on-suite) and 4 baths (2 with original clawfoot tubs). Much to love with this Old Bennington home with handsome foyer, bright light filled library, and hardwood floors. Elegantly situated on 3 acres with mature landscaping. Beautiful walking trail behind the property owned by the Bennington Museum. A perfect location in the village with easy access to NY and MA.

Listed by Kelley McCarthy of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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34 West Road Bennington VT 05201

Bennington, VT34 West Road

Price$569,000

Est. Mortgage: $/month

MLS Number 4840013

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bedrooms 7
  • Bathroom 6

Large home in highly desirable historic neighborhood of Old Bennington. Was originally a single family home but currently is setup as a 4 unit. Would take a little work to convert back to a single family. Grand columns, lots of space, large porch and so much more. 7 total bedrooms, 5 and half bathrooms, many possible layouts. Offers 1.56 acres and 4 car detached garage.

Listed by Brenda Jones of KW Vermont - Brenda Jones Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated May 8, 2021.