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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.

Old Bennington

11 West Road Bennington VT 05201

Price$945,000

Est. Mortgage: $/month

MLS Number 4701683

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

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

74 Monument Avenue Bennington VT 05201

Price$675,000

Est. Mortgage: $/month

MLS Number 4642740

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

Rich in Revolutionary War history and reputed to be the oldest continuously occupied home in Vermont, this handsome 1763 Federal is listed on the National Register of Historic Places. Retaining many original features including 4 marble fireplaces, 22" wideboard pine flooring and paneling throughout, along with a hand painted mural above the former kitchen fireplace depicting Old Bennington at the beginning of the 19th Century. A tasteful 1920 addition, featuring a recently renovated, stunning and tastefully appointed kitchen with marble countertops, top of the line stainless appliances including separate steam oven, blend in seamlessly with the original structure. Offering 4 large en-suite bedrooms with full baths, including one currently in use as a den; large living room and adjoining library with built in bookcases; large dining room with fireplace; bright Butler's pantry with prep sink, corian counters and ample storage perfect for entertaining. Handsome foyer, bright office/study and half bath round out this well laid out and proportioned first floor. Elegantly situated on 3.64 lush acres offering a private bluestone terrace off the kitchen, marble courtyard, scenic mountain views, manicured lawns, mature landscaping with stonewalls and gazeebo present this property magnificently. Separate 3 bedroom guest cottage off the courtyard and 35' x 23' lightfilled studio with hard wood floors and vaulted ceiling round out this exquisite offering.

Listed by Suzan Yucht of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

Price$579,000

Est. Mortgage: $/month

MLS Number 4716607

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

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: 3.55% last updated on Aug 22, 2019
* 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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77 Monument Avenue Bennington VT 05201

Price$499,000

Est. Mortgage: $/month

MLS Number 4756327

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

Located in the prestigious Village of Old Bennington, this beautiful 4,000+ sq. ft. center hall Colonial sits on 1.6 nicely landscaped acres with a year round creek and a footbridge. Off the large foyer is a parlor with a fireplace and ½ bath, beautiful dining room and stairway to the second floor. Further down the foyer leads to the kitchen and large family room with fireplace/pellet stove. Off the family room is a south facing 3 season porch. The gourmet's dream kitchen features a 6 burner professional stovetop, warming drawer, built in microwave oven, refrigerator, beverage refrigerator, 2 convection ovens and 3 sinks all in stainless steel. The extensive counter space and island are topped with Brazilian granite and compliment the overabundance of cabinetry. The first floor finishes up with a large private office off the kitchen with a back stairway to the second floor bedrooms. Upstairs are 4 large bedrooms, two of which are master suites with walk-in showers. The 3rd bathroom features a whirlpool tub with shower. A large linen closet and laundry complete the second floor. An attic with stairwell is accessed from the main center hall of the second floor. The full basement features a work shop area and has access for parking two cars in tandem. The home has been well cared for with electrical and plumbing upgrades, roofing, and rebuilt chimneys. Available turn-key.

Listed by Kathleen Hoisington of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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$495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4649624

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

Move right in to this private mint condition historic home with pool and carriage house. Meticulously renovated by its current owners, this sprawling home is nestled in the trees down a long sheltered driveway. A wrap-around porch offers mountain views across the park-like grounds; a luxurious gunite pool with bluestone coping draws you to the secluded side yard. With six bedrooms and 4.5 baths, plus game room, mudroom and family room, there is plenty of space for family and guests. The country kitchen, with Sub-Zero and Bosch appliances and custom Rutt cabinetry, welcomes the serious cook. A butler's pantry with wine storage and sink leads to the dining room with glass chandelier. Gleaming hardwood floors throughout. With fireplaces in the living rooms - and the master bedroom - this home is a perfect all-season retreat. Old Bennington, anchored by the Bennington Monument, is located at the nexus of Southern New England. Enjoy skiing and winter sports at Bromley and Stratton, summer theater and music at Marlboro and Williamstown, and art at Bennington College. Or just settle in next to the fireplace and let the world slip away. Come see this extraordinary home and begin the next chapter of your extraordinary life.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

1 Monument Avenue Bennington VT 05201

Price$495,000

Est. Mortgage: $/month

MLS Number 4490469

  • Residential Single Family
  • Village Old Bennington
  • Construction Existing
  • Bathroom 2
  • Bedrooms 5

Location, Charm and History. Circa 1790 Center Hall Colonial in the heart of Old Bennington Village. Restored turn-key condition. Prominent location in the Historic District, on the hill and adjacent to the Bennington Battle Monument. Light-filled rooms with views of the Monument. Walking distance to downtown Bennington shops along one of the prettiest residential streets in New England. Two garages, one under the main house and one in the restored carriage barn. Underground wiring preserves the tranquil 19th Century setting at the center of Vermont's Revolutionary History. Built by Captain David Robinson Jr., grandson of the founder of Bennington. The center hall leads to a front-to-back living room with fireplace and bookcase. Many built-ins throughout. Formal dining room, newly appointed kitchen and informal sitting room. In-law guest suite or private office with its own living room, bedroom, full bath and entrance. Large light-filled second floor master with views of the Monument to the north and Mt. Anthony to the south. Three more bedrooms on the second floor and a new full bath. Full basement with workshop, wine cellar and large laundry/play space. Separate interior staircase from the basement garage to the first floor. Town water. Propane heat. Recent improvements include central air and heat pump on the first floor, electrical upgrades, and new sewer line connecting to town service.

Listed by Kathleen Hoisington of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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9 Monument Avenue Bennington VT 05201

Price$450,000

Est. Mortgage: $/month

MLS Number 4758455

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

Presenting 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 Monument Avenue Bennington VT 05201

Price$369,900

Est. Mortgage: $/month

MLS Number 4730296

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

Located in historic and prestigious Old Bennington this colonial style home offers old world charm and modern convenience. Known locally as The Spargo House, the home was owned by the historic author John Spargo, who later went on to be the founder and curator of The Bennington Museum in 1927. Situated on 1.0 +/- acre and offering 4 bedrooms including a large master suite, 2 full and 1 half baths, large eat-in kitchen that has been completely updated, bright and sunny formal dining room, living room, family room with fireplace, den/office and much more. Some terrific wood floors, a wonderful rear deck and patio, 1 car basement garage and large rear yard complete this great home.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

25 Monument Avenue Bennington VT 05201

Price$339,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4702286

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

GREAT NEW PRICE! One of Old Bennington's premier properties offered for New Price. Long admired for its classic New England charm this 4 bedrooms, 3.5 bath home with a fireplace and a 2 car garage has beautifully maintained hardwood floors on the 1st level. The location is unbeatable, surrounded by classic and historic New England style homes and offers a commanding view of Mt. Anthony from the patio and inground pool. For those looking for quality and a first floor master bedroom suite this must be viewed. This residence has GREAT BONES AND ONLY NEEDS YOUR INTERIOR DESIGN TO make it irresistible and better than anything on the market in the $500,000 range. 1.85 acres. Come see for yourselves. Our sellers want this home sold this summer - it could be yours!!!! New price of $339,900.

Listed by Kelley McCarthy of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

31 Bank Street Bennington VT 05201

Price$335,000

Est. Mortgage: $/month

MLS Number 4769107

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

No box left unchecked in this 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 or could potentially be a 4th BR. 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: 3.55% last updated on Aug 22, 2019
* 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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12 West Road Bennington VT 05201

Price$334,000

Est. Mortgage: $/month

MLS Number 4755890

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

A terrific opportunity in Old Bennington awaits you. Well cared for and modestly updated, she still has the feeling of history. Offering 4 bedrooms, 4 baths, hard wood floors throughout, eat in kitchen with adjacent large Butler's pantry, dining room, large living room with wood burning fire place and French doors that open onto terrific light filled enclosed porch, mudroom and laundry round out her first floor. You will find a sweet spot to perch on the mid-level landing with window seat as you head up to the second floor, where you will find 4 bedrooms, 3 baths, plenty of linen and storage built-ins. The Master suite opens into a terrific sitting room or studio, your choice. You may never want to leave your bedroom again. Three of the 4 bathrooms in the house have all been updated, while 4th bath with claw foot tub remains as it was back in the day. Huge walk up 5 dormer attic with cedar closet can be put to its next best use. New spray foam insulation in attic and basement, partial new roof, painted interior and exterior are among the many benefits the next steward will appreciate. A pleasure to show.

Listed by Suzan Yucht of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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$299,000

Est. Mortgage: $/month

MLS Number 4660848

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

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. And if you need more space, there's a large bonus room that is partially finished with endless possibilities. Once used to store a large collection of books, the reinforced flooring can take on a new pool table so make this into the Rec room of your dreams! 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 2019 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 24, 2019.