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

Pending

MLS Number 4864908

  • Residential Single Family
  • Village Old Bennington
  • Bathroom 4
  • Square Feet 4,541
  • Construction Existing

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: 3.09% last updated on Oct 21, 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: 3.09% last updated on Oct 21, 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

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: 3.09% last updated on Oct 21, 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

55 Monument Avenue Bennington VT 05201

Bennington, VT55 Monument Avenue

Price$485,000

Est. Mortgage: $/month

MLS Number 4884333

  • Residential Single Family
  • Village Old Bennington
  • Bathroom 3
  • Square Feet 2,675
  • Construction Existing

Located on one of the prettiest streets in Bennington, this proud Colonial has been lovingly cared for and is ready to invite you home. Built in 1787, this gem has stood the test of time! Known as the Asa Hyde house, a cabinet maker from Connecticut who came to Bennington to work on the building of the Old First Church. Walk across the street to see his craftsmanship or take a stroll to the Bennington Battle Monument. A short walk to downtown and the Putnam Block with dining, shops and so much more. This grand home has gorgeous wide plank flooring throughout and beautiful exposed beams in the dining room. A lovely guest suite or master suite is located just off the kitchen, and two generous bedrooms (one with a fireplace) plus a study/playroom are on the second floor. Large living room and family rooms are light filled and feature wood burning fireplaces and built in cabinetry. Overlooking the lush back yard and gazebo is a coveted screened-in porch which can be accessed from the foyer, the living room and the dining room. It's the perfect space for al-fresco dining and entertaining! Enjoy the beauty and history of "Picturesque New England" from your front door. This Old Bennington charmer has so much to offer; Three bedrooms, three bathrooms, three fireplaces, an attached garage, and a walkable village location. Easy access to NY and MA.

Listed by Angela Bevin of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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 October 24, 2021.