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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.

21 West, Bennington, VT

Price$2,200,000

MLS Number 4669893

  • Commercial
  • Listing Agent Name Pamela Long
  • Village Old Bennington
  • Year Built 1913
  • Acreage 11

This going concern inn business is one of the strongest financial performers in Vermont with annual occupancy over 60%. The 11 guest rooms and suites are stylishly updated and furnished with an eye to preserving the inn's old world charm. All have private baths, flat screen TV's and individually controlled heat and air-conditioning. Most have working fireplaces and luxurious bathrooms with jetted tubs. Due to its strategic location, architectural style and appeal, this inn attracts both business and leisure travelers.

Listed by Pamela Long of East Coast Inn Brokers

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Hoisington Realty
489 Main Street
Bennington VT, 05201
Office: 802-442-8337

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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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11 West Road, Bennington, VT 05201

Price$995,000

Est. Mortgage: $/month

MLS Number 4701683

  • Residential Single Family
  • Listing Agent Name Kathleen Hoisington
  • Village Old Bennington
  • Construction Existing
  • Bathroom 5

One of the finest Revolutionary Period properties in Vermont completely restored under the guidance of historical consultants. The Isaac Tichenor House c. 1788 is a living masterpiece of elegant historical design graced with the finest modernizations of kitchen, baths and mechanical systems. The grounds include gardens modeled after the 1930s garden plans along with a restored clay tennis court, renewed pond and designated wetlands for a fabulous outdoor setting that frames both the Bennington Battle Monument and Mount Anthony. Historical detail, a complete list of improvements and floor plans available on request. Governor Isaac Tichenor was the third Governor of Vermont who was also Chief Justice of the Vermont Supreme Court and a United States Senator. If you are passionate about the history of the beginning of our country and the State of Vermont you will be passionate about this house and the story that goes with it. 3-car heated garage, 5.7 acres.

Listed by Kathleen Hoisington of Hoisington Realty, Inc.

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Hoisington Realty
489 Main Street
Bennington VT, 05201
Office: 802-442-8337

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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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40 Monument Avenue, Bennington, VT 05201

Price$595,000

Est. Mortgage: $/month

MLS Number 4649624

  • Residential Single Family
  • Listing Agent Name Brenda Jones
  • Village Old Bennington
  • Bedrooms 6
  • Bathroom 6

Nestle yourself amidst the trees and next to the fireplace in this grand Colonial home on 3.40 acres in Old Bennington. Great features include 6 bedrooms, 4.5 bathrooms, formal dining room with butler's pantry, welcoming family room with fireplace, master suite with separate shower and fireplace, elegant formal living room with hardwood floors and fireplace, second-floor laundry, traditional kitchen, mud room to contain the mess, den with fireplace and built-in book shelves, solid wood floors and security system. Outside you'll experience a plethora of features including an in-ground pool, shaded yard, mature plants, carriage barn with 2-car garage, tool storage shed, deck, patio, and large covered porch. A magnificent home in a historic location.

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

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Hoisington Realty
489 Main Street
Bennington VT, 05201
Office: 802-442-8337

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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 A VisitAsk A QuestionMore Details

1 Monument Avenue, Bennington, VT 05201

Price$549,900

Est. Mortgage: $/month

MLS Number 4490469

  • Residential Single Family
  • Listing Agent Name Kathleen Hoisington
  • Village Old Bennington
  • Bedrooms 5
  • Bathroom 2

This c. 1790 Center Hall Colonial was built by Captain David Robinson Jr, son of Major General David Robinson, and grandson of the founder of Bennington. On his death Captain Robinson deeded it to the historic First Congregational Church and it served as the parsonage for 100 years. Property includes the restored late 18th century carriage barn.Restored and in turn key condition, this home is adjacent to and frames The Bennington Battle Monument from several rooms. The center hall leads to a front to back living room with fireplace and bookcases on the south side. On the north side of the hall a formal dining room overlooks the Bennington Battle Monument. Newly appointed kitchen, informal sitting room and in-law guest suite or private office with its own living room, bedroom, full bath and entrance complete the first floor. Central air on first floor. The second floor embraces a wide open hall with beckoning window seat flanked by bookcases overlooking the tree-lined Avenue. Four more bedrooms with corner ventilation in all rooms and a new full bath. Walk up attic and full basement with wine cellar and large playroom/laundry/ office. Ground level access to gardens and patio. Separate interior staircase from the basement garage to the first floor. Showcase perennial gardens and restored Carriage barn/Garage with electricity, and underground wiring at the site preserve the tranquil 19th Century setting at the center of Vermont's Revolutionary History.

Listed by Kathleen Hoisington of Hoisington Realty, Inc.

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Hoisington Realty
489 Main Street
Bennington VT, 05201
Office: 802-442-8337

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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 A VisitAsk A QuestionMore Details

9 Monument, Bennington, VT 05201

Price$499,000

Est. Mortgage: $/month

MLS Number 4665617

  • Residential Single Family
  • Listing Agent Name Kathleen Hoisington
  • Village Old Bennington
  • Bedrooms 5
  • Bathroom 6

PPresenting the Governor John S. Robinson home, Circa 1862. The original home was razed by his Widow Mary Staniford Robinson and she actually built the home that is to this day one of the outstanding historical homes in Old Bennington. Designed in the Greek Revival Style with elaborate dentil work on the exterior. Gracious entry hall with original door, open stairwell with mahogany balusters and powder room. The living room has a fireplace, window seat and French doors to the heated sunroom with westerly views. Music room with fireplace and full paned door to the open veranda, dining room with crown moldings and indirect lighting and sunroom access, Kitchen with spectacular views of Mount Anthony, Cozy side entry/mudroom with separate outside entrance to the Apartment. The 2nd floor has 4 bedrooms - 2 of which are ensuite as well as two other bedrooms with a hall bathroom and rear staircase to kitchen. The westerly facing bedroom also has a charming fireplace. . The attic is finished with sheetrock and heat with original board flooring. The basement is under the entire house and is compartmentalized into several pristine rooms with freshly painted walls and a utility bathroom. 2 car garage with automatic door openers. There is an attached 2 bedroom 1 bath apartment with front and rear entries. On the south side of the house there is a private wood planked patio flanked by stone walls and plantings.

Listed by Kathleen Hoisington of Hoisington Realty, Inc.

{$office->Name}

Hoisington Realty
489 Main Street
Bennington VT, 05201
Office: 802-442-8337

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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 A VisitAsk A QuestionMore Details

25 Monument Avenue, Bennington, VT 05201

Price$399,900

Est. Mortgage: $/month

MLS Number 4702286

  • Residential Single Family
  • Listing Agent Name Kelley McCarthy
  • Village Old Bennington
  • Construction Existing
  • Bathroom 4

One of Old Bennington's premier properties offered for the first time in over a half century. Cape Cod style home with amazing views and location on 2 acres that blends seamlessly with the 18th and 19th century homes lining Monument Avenue. Gracious living room with fireplace overlooking the beautiful setting and Mt. Anthony. Four bedrooms, including master suite, and 3 additional baths. Partially finished basement with historical, folk art mural. Floor plan invites many options for entertaining and living!

Listed by Kelley McCarthy of Hoisington Realty, Inc.

{$office->Name}

Hoisington Realty
489 Main Street
Bennington VT, 05201
Office: 802-442-8337

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

38 Monument Avenue, Bennington, VT 05201

Price$349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4620824

  • Residential Single Family
  • Listing Agent Name Brenda Jones
  • Village Old Bennington
  • Bedrooms 3
  • Bathroom 3

Entertain...In the great room of this updated gambrel style home in a historic location. Has 3 bedrooms, 2.5 bathrooms, gracious great room with fireplace for winter nights, master suite with dual sinks, separate shower and privacy room, bright kitchen with breakfast bar, pantry and solid-surface countertops, 1-car attached garage, deck, security system, and radiant-floor heating. Amazing home in historic Old Bennington.

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

{$office->Name}

Hoisington Realty
489 Main Street
Bennington VT, 05201
Office: 802-442-8337

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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 A VisitAsk A QuestionMore Details

81 Monument Avenue, Bennington, VT 05201

Price$339,000

Est. Mortgage: $/month

MLS Number 4660848

  • Residential Single Family
  • Listing Agent Name Angela Bevin
  • Lister Office Name Maple Leaf Realty
  • Village Old Bennington
  • Construction Existing

Stately Colonial in the heart of Old Bennington Village on a picturesque tree lined street. Once the home of Captain Isaiah Hendryx, a retired Captain in the Revolutionary War, it now features a beautiful blend of historic details with modern amenities. The home has been lovingly updated and meticulously cared for. Original wide plank flooring throughout, updated kitchen with classic soapstone countertops, plenty of storage and pantry space. The generous living and family rooms are flooded with sunlight. Upstairs are 4 bedrooms, 2 bathrooms, and a dedicated laundry room. A lovely sleeping porch is connected to one of the bedrooms, perfect for cool summer nights! The main bathroom features a large clawfoot tub and custom tiled shower. A nice flat back yard, fully fenced, with mature trees is great for outdoor fun. This village home is just a stroll away from the historic First Church, the Bennington Battle Monument, Monument Elementary School and the many outdoor festivals at Camelot Village! "Settledown" on the prettiest street in Bennington!

Listed by Angela Bevin of Maple Leaf Realty

{$office->Name}

Hoisington Realty
489 Main Street
Bennington VT, 05201
Office: 802-442-8337

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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 A VisitAsk A QuestionMore Details

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Copyright 2018 Northern 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. Subject to errors, omissions, prior sale, change or withdrawal without notice. This web site is updated daily.