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.

11 Monument Avenue Bennington VT 05201

Bennington, VT11 Monument Avenue

Price$695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4864908

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

Exceptional historic residence in the heart of Old Bennington! This stately home has been beautifully maintained and is rich in architectural detail including original floor boards, three large fireplaces and exposed beams. Enormous gourmet kitchen with high end appliances, soap stone countertops, a large island, butler's pantry with a second refrigerator and a large seating area. The large living room features a central fireplace, looks onto beautiful Monument Avenue and leads to a large sun porch filled with natural light. The dining room is full of colonial charm and features a huge, original fireplace and is large enough for a banquet size table. This large home has been thoughtfully upgraded throughout the years and has wonderful practical aspects such as full insulation, a large laundry room, walk in coat closet, ample storage throughout and a cavernous basement featuring original stonework. Five bedrooms (two en suite) with beautiful wooden floors and moldings, three and a half baths (all updated) and a large parlor with a wood stove complete this amazing home. The park-like grounds are approximately 2 acres and feature a large two car garage. This is the best of both worlds - living on the most desirable street in southern Vermont with bucolic views to the west and amazing sunsets all year long. Quick trip to train and airport make this an ideal residence for those that require proximity to New York or travel extensively.

Listed by Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

Active With Contract

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 Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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: 2.78% last updated on Jul 22, 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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230 Walloomsac Road Bennington VT 05201

Bennington, VT230 Walloomsac Road

Price$499,000

Est. Mortgage: $/month

MLS Number 4869951

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1

This 1901 Carriage House estate is tucked away waiting for someone to restore it to better than it's original glory! Rare to see this much acreage! Set on almost nine acres of stunning grounds and woods/trails with a view of Mount Anthony, the property sits partially in Old Bennington. Minutes walk to Monument or stroll downtown to shops and restaurants. Inside you'll see gorgeous beadboard walls, stone fireplace, one bedroom/bath existing, sunroom facing Mt Anthony! Comes with new furnace, new windows, and new oil tank. This project is not for the faint at heart but your results will bring you a once in a lifetime home.

Listed by Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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2 Church Lane Bennington VT 05201

Bennington, VT2 Church Lane

Price$360,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4867638

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4

*Highest and best offers by 5pm on 6/24* Own a piece of the past in Old Bennington! This unique and utterly charming property built in 1825 is thought to be a carriage barn conversion and sits directly behind the Old First Church. Sure to delight any lover of history and literature, the final resting place of famed poet Robert Frost is just steps away. There is even an old repurposed horse trough outside! Original beams adorn much of the home and the open layout is refreshing. The warm kitchen boasts many updates including soap stone countertops, a large island with plenty of storage, and a brand new refrigerator. Entertain by the fireplace in the gorgeous formal living room or relax by the wood stove in the cozy den. There is a first floor master bedroom with ensuite bath as well as a powder room and utility room that houses the laundry station. Upstairs there is a spacious bedroom with stunning mountain views and plenty of storage with attached bonus room... an office, gym, hobby room, you name it! The large walk-in attic space is impressive. You will also find a full bathroom with claw foot tub and slate floor. If all of this wasn't enough, there is a one bedroom apartment with a separate entrance that could be added income for the new owner or space for whatever their heart desires! An attached two car garage, newer Buderus furnace, porch, patio, and low maintenance yard round out a truly extraordinary property.

Listed by Justine Curry of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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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 July 23, 2021.