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.

Old Bennington

11 West Road Bennington VT 05201

Bennington, VT11 West Road

Price$875,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4701683

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6

The historic importance of Tichenor Place, constructed by Isaac Tichenor in 1788, cannot be overstated as on the wall in the second floor hall is a section of the original wallpaper dating from 1800 that commemorates the passing of the nation's first president, George Washington. George Washington knew Isaac Tichenor well as Tichenor was his assistant Deputy Commissary for the Northern District during the Revolutionary War. When President Washington passed away in 1799 the Boston Paper Staining Manufactury created a commemorative wallpaper "Sacred to Washington", that was sent to the Governors of the then 16 states. The paper is divided into sections by Doric columns topped with classical arches. A funeral monument in the shape of a large urn is the central motif surmounted by an eagle shielding his head under his wing. Justice and Liberty stand leaning on the monument. Justice is blindfolded and Liberty lifts her hand to her face as though mourning the death of the great leader. The Governor Isaac Tichenor House is a masterpiece of elegant historical Federal design with the finest of modernizations. 12 main rooms including library, 6 bedrooms, 5 baths, 6 fireplaces. An attached three car heated garage plus 5.7 acres with an active pond and prominent view of the Bennington Battle Monument. If you are passionate about our country and Vermont, you will be passionate about this house and the story that goes with it.

Listed by Kathleen Hoisington of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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Old Bennington

33 Monument Avenue Bennington VT 05201

Bennington, VT33 Monument Avenue

Price$560,000

Est. Mortgage: $/month

MLS Number 4716607

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bedrooms 3
  • Bathroom 5

Presenting for the first time this grand Old Bennington residence built in 1930 with architectural detail honoring classic historic Colonial home appointments. This home is immensely comfortable, elegant and easy to take care of due to its premier construction, new kitchen, oak hardwood floors, newer furnace and numerous Anderson replacement windows with e glass. First and second floor sunrooms frame Mount Anthony while stonewalls, gardens and white picket fencing define the property. Traditional floor plan with entry hall; open stairway with oval frosted glass window, soapstone faced fireplace in the formal living room, formal dining room, den, cherry cabineted kitchen with views and French doors to deck. Three second floor bedrooms, each with full bath, additional full bath on the main level and ground level billiard room updated with work and study areas. Slate roof. New 2-car garage, 1.10 acres.

Listed by Kathleen Hoisington of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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57 Monument Avenue Bennington VT 05201

Bennington, VT57 Monument Avenue

Price$499,000

Est. Mortgage: $/month

MLS Number 4788077

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

Exquisite Center Hall Colonial on the Village Green in Old Bennington. A true show stopper of a home featuring 5 bedrooms and 4 bathrooms. Large and inviting, the Dr. Noadiah Swift House has seen many renovations without compromising the gorgeous original details that abound in the home. Formal living room with gas fireplace, renovated kitchen, breakfast nook, and a large formal dining room all with plentiful windows which allow the rooms to be flooded with natural light. The true heart of the home is the amazing attached carriage barn with huge soapstone fireplace, rustic beams, and vaulted ceilings. The second floor features a master bedroom with walk-in California Closets and a master bathroom reminiscent of old Hollywood glam! Not to be overlooked is the recent renovation of the guest bathroom with geometric black and white tile and luxurious finishes. This grand home sits on a generous lot with a lovely stone patio for al-fresco dining in the summer. The thoughtfully designed gardens are lush and include mature plantings, landscape lighting and stone walls. Fall in love with this gracious home and enjoy the beauty of quintessential Vermont! A perfect location in the village with easy access to NY and MA.

Listed by Angela Bevin of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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10 West Road Bennington VT 05201

Bennington, VT10 West Road

Price$349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4816120

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bathroom 2
  • Bedrooms 2

This unique & historic home, the former Old Bennington Schoolhouse, isn't your grandmother's one-room school. The original building, which dates back to 1881, has high ceilings, tall windows, wainscot walls, hardwood floors, a huge living room, a small kitchen and bathroom, & a stage that's closed off with French doors to make it a bedroom. It also has a very bright room on the lower level with four windows & a slate floor that could be used as an office, a sewing room, an art studio, or another bedroom. The modern addition put on in 1999 has a large bedroom with a huge Palladian window that looks out onto the similar Palladian windows of the Old First Church just up the street. The view of the church from the bedroom is particularly stunning when the church is lighted up on winter nights. It also has a large bath and a very large combination kitchen & family room. The one-acre yard has lush gardens, a bluestone patio, stone walls, granite birdbaths, and peach, pear, plum and cherry trees & ten apple trees. It has views of the Battle Monument & Mount Anthony, & the eastern border is a small brook. The amenities include a "Defiant" wood stove, a gas fireplace, ceiling fans, a whirlpool bath, & built-in cabinets and bookcases. It's surrounded by quality properties, including the 18th century home of former Governor Isaac Tichenor & the Four Chimneys Inn, as well as the Bennington Museum & the Old First Church, which includes the grave of Robert Frost.

Listed by Paul William Carroccio and Marek Kovac of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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31 Bank Street Bennington VT 05201

Bennington, VT31 Bank Street

Price$319,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4829025

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3

3BR/2BA home located on 3 rolling acres in the Village of Old Bennington abutting Mount Anthony Country Club. Get right to making memories and incredible meals in the updated kitchen w/ open floor plan living and dining. Cozy up by the fireplace in cooler months or enjoy your coffee in the newly renovated three season sun room. Spacious master suite offers mountain views & private bath. Bonus Room on the lower level is ready for fun, potentially be a 4th BR or would make the perfect home office! Generous basement provides space for the ultimate workshop. The attached 2 car garage keeps your cars and toys clean. Private feel yet minutes to town, dining, shopping, entertainment.

Listed by Abi Gregorio of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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 2020 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 October 30, 2020.