Old Bennington Real Estate

Old Bennington today is a graceful village of historic homes from the Revolutionary,
Antebellum and Victorian years of our country. The entire village was designated a National
Historic District in 1984. The dominant architectural style is Federal and homes built later, into
the 20th century also favored this style.


Directly across from the village green lies a remarkable cemetery of Revolutionary War heroes
as well as other notable’s 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.
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. It was the first church in Vermont.


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


When the post office officially made the move in 1848 to the valley, Bennington on The Hill or
Bennington Centre became Old Bennington and Bennington was reorganized. Old Bennington,
over time, took advantage of becoming a residential village as businesses followed the commerce
down the hill. It is quite unique that now, Old Bennington is limited to residential zoning with
some home occupations.

One outstanding example of bygone days is reflected in the
Walloomsac Inn which had originally been the home of Jedidiah Dewey’s son Elijah and still
stands, though closed to the public. A few other grandfathered businesses remained but are no
longer there. The grandest feature of all is The Bennington Battle Monument, commemorating
The Battle of Bennington, a significant turning point in The Revolutionary War.

There are 97 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.


If you cherish history and elegant historic and vintage homes you must put this village on your
list of possibilities.

Hoisington Realty is pleased to provide the following Old Bennington Village Real Estate listings. If you don't find the property you seek here, or if you need more information about Bennington, Please contact us.

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: 2.8% last updated on Jul 29, 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

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: 2.8% last updated on Jul 29, 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

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: 2.8% last updated on Jul 29, 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

230 Walloomsac Road Bennington VT 05201

Bennington, VT230 Walloomsac Road

Price$499,000

Est. Mortgage: $/month

Active With Contract

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: 2.8% last updated on Jul 29, 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

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: 2.8% last updated on Jul 29, 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

Broker Reciprocity

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 August 3, 2021.