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Bennington County Real Estate

Bennington is the oldest county in Vermont.  Bennington not only has abundant cultural resources like the Bennington Museum and Southern Vermont Art Center but is also served by well respected institutions such as Southern Vermont College and Bennington College. The largest towns in Bennington County are Bennington and Shaftsbury. Browse available Bennington County real estate below. 

Bennington County VT Homes for Sale

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303 Westview Estates Manchester VT 05255

Manchester, VT303 Westview Estates

Price$995,000

Est. Mortgage: $/month

MLS Number 4971678

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 4,432

Welcome to your dream log home retreat! Located on the ski side of town, this log home provides a serene escape from the hustle and bustle of daily life. Whether you are hitting the slopes or exploring the charm of Manchester, you will find that this location offers the perfect balance of outdoor adventure and cultural experiences. With five bedrooms, three baths, a massive stone fireplace, and a finished lower level, this home is the place to sip hot cocoa by the fire, share stories of the day's adventures, and create cherished memories that will last a lifetime. The open-concept living area seamlessly connects the kitchen, dining, and living spaces, creating an ideal environment for entertaining and socializing. The attached two-car garage offers convenient storage and parking for your vehicles and outdoor gear. Contact us today to schedule a viewing and start living the Vermont lifestyle you've always dreamed of. All measurements approximate. Showings begin Saturday, September 30th at 1:00 pm.

Listed by Carol O'Connor of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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Barney Orchard Road Sunderland VT 05250

Sunderland, VTBarney Orchard Road

Price$75,000

Est. Mortgage: $/month

MLS Number 4971643

  • Land
  • Acreage 2.5
  • Zoning Rural Residential

Welcome to serenity! Peace and quiet abound in this 2.5-acre private building lot. Sweet wooded lot is ready for the next owner. Come build your dream home with the potential for beautiful mountain vistas. Conveniently located less than 10 minutes to Manchester, 20 minutes to Bromley and 30 minutes to Stratton. Come breathe the fresh Vermont air and relax on your own slice of heaven. Call today!

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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13-84 Marshall Drive Shaftsbury VT 05262

Shaftsbury, VT13-84 Marshall Drive

Price$549,000

Est. Mortgage: $/month

MLS Number 4971617

  • Multifamily
  • Units 2
  • Bathroom 3
  • Square Feet 2,646
  • Acreage 3.6

So many opportunities are afforded by this property! It includes a 4BR/3BA Colonial farmhouse built in 2000, oversized heated garage, horse barn with water and electricity and a separate c. 1940 3BR/1BA cottage on a 3.6 acre parcel with fenced in pasture. Main house is open and bright on the first level with half/bath laundry room, kitchen with great storage open to the back deck and dining room, large living room and family room/office. Second floor includes the primary ensuite with soaking tub and walk-in shower plus 3 guest bedrooms and additional full bath. All new vinyl flooring throughout. Cottage is sweet and bright! Kitchen, large dining room, living room, 2 bedrooms and full bath on first floor and large bedroom on the second floor. All located within the commercial overlay zone but bordered on two sides by conserved agricultural lands. Bring your imagination and entrepreneurial spirit!

Listed by Vicki Wilson of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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6923 Vermont Route 9 Woodford VT 05201

Woodford, VT6923 Vermont Route 9

Price$80,000

Est. Mortgage: $/month

MLS Number 4971553

  • Residential Single Family
  • Square Feet 715
  • Bathroom 1
  • Construction Existing
  • Bedrooms 1

This camp is in the best location for everything outdoors! This property backs up to the Green Mountain National Forest. Therefore, just walk out of your front door to hunt, snowmobile and hike. Or, just relax on the back deck overlooking the year-round brook that runs through the property. This camp is also being conveyed with the original 3 story camp (with) power that is curranty being used for storage. This structure could be brought back to a livable state with some work.

Listed by Melissa Nebelski of Skihome Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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318 Spring Hill Lane Dorset VT 05251

Dorset, VT318 Spring Hill Lane

Price$4,875,000

Est. Mortgage: $/month

MLS Number 4971483

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4,922

Hidden at the top of one of Dorset's quiet lanes you will discover the epitome of timeless elegance & modern luxury in this meticulously renovated 5-bedroom, 6-bathroom 1941 Colonial. On a sprawling 9.4-acre estate, this enchanting property offers a harmonious blend of history and sophistication. 6 fireplaces evoke a warm and inviting ambiance, creating the perfect backdrop for cozy and memorable gatherings. The post & beam great room addition is a breathtaking architectural achievement. With soaring ceilings, exposed beams, and expansive windows; a seamless connection between the interior and the natural beauty of the exterior landscape. Outside, meticulously landscaped grounds beckon you to explore. Stone walls add character, while expertly crafted gardens bloom with color. The tranquil brook that meanders through the property offers a soothing soundtrack to your daily life. A short distance from the main residence you arrive at a remarkable stone and timber barn designed for all your recreational needs, by noted architect, Ramsay Gourd. Continuing down the path you arrive at the private, two bedroom/two bath, elegantly appointed guest cottage, with rear private patio to enjoy some quiet down time. Located close to the main house is the free form pool and exquisite pool house. This property is not just a home; it's a lifestyle, a retreat; an opportunity to own a piece of paradise. Don't miss your chance to make this exquisite compound your own. More information attached.

Listed by Richard Slocum of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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41,42,43 Moose Hollow Road Winhall VT 05340

MLS Number 4971446

  • Land
  • Acreage 3
  • Utilities Cable - Available
  • Zoning Residensial

Purchase all three lots: #41, 42, 43 consisting of total 3 acres. All lots are state permitted with individual septic designs. Great spot to be so close to Manchester and Bromley, Stratton Ski areas. Wonderful location to build your vacation or year round homes with family and friends. Partial mountain views.

Listed by Patricia Trudel of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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43 Moose Hollow Road Winhall VT 05340

Winhall, VT43 Moose Hollow Road

Price$75,000

Est. Mortgage: $/month

MLS Number 4971445

  • Land
  • Acreage 1
  • Utilities Cable - Available
  • Zoning Rural Residential

Set in the hills of Winhall build your Vermont get-away or year round home. Permitted lot for 4 bedroom home with septic design included. Site cleared. Close to ski areas Stratton, Bromley and short drive to Manchester for shopping. School Choice.

Listed by Patricia Trudel of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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41 Moose Hollow Road Winhall VT 05340

Winhall, VT41 Moose Hollow Road

Price$79,000

Est. Mortgage: $/month

MLS Number 4971444

  • Land
  • Acreage 1
  • Utilities Cable - Available
  • Zoning Rural Residenial

Great location. Minutes to Bromley, Stratton and Manchester. Country setting. Septic permitted for 4 bedroom home. Cleared parcel makes it easy to picture your home. School choice and close to the snowmobiling VAST trails.

Listed by Patricia Trudel of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

42 Moose Hollow Road Winhall VT 05340

Winhall, VT42 Moose Hollow Road

Price$75,000

Est. Mortgage: $/month

MLS Number 4971443

  • Land
  • Acreage 1
  • Utilities Cable - Available
  • Zoning Residential

Cleared lot with privacy. Short drive to Stratton, Bromley and Manchester Center. Permitted for 4 bedroom home. Septic design included. Build your special home whether year round or a vacation get away. Partial winter view.

Listed by Patricia Trudel of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

287 Hewitt Drive Shaftsbury VT 05257

Shaftsbury, VT287 Hewitt Drive

Price$475,000

Est. Mortgage: $/month

MLS Number 4971351

  • Residential Single Family
  • Village North Bennington
  • Square Feet 3,042
  • Construction Existing
  • Bathroom 2

This is truly a rare find! Beautifully updated with a major addition in 2022, including new windows and entirely new vinyl siding. Much of this home is brand new. Single level living with three generous bedrooms plus a dedicated office/den. The primary bedroom has an oversized closet and ensuite bathroom for convenience. Featuring a large and open layout, it's perfect for entertaining family and friends. A newly added sunroom and plentiful windows add to the light and airy feel of the living space. Not just a "pretty" home, but incredibly comfortable and well thought out too. A wood burning fireplace provides warmth and ambiance on those cold Vermont nights, and a mini split system will keep you cool all summer long! On the lower level you'll find a large Rec Room as well as a dedicated storage room to keep your home clutter free. The oversized two car garage enters through the basement. Outdoors you'll enjoy gorgeous sunsets on your back deck, or dine alfresco with the retractable awning providing much needed shade. A partially fenced yard on a quiet dead end street and elementary school choice are all part of this magnificent offering!

Listed by Angela Bevin of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 September 27, 2023 6:24 PM EDT