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Bennington Homes with Virtual Tours

Scroll down to browse all homes in Bennington, Vermont that feature virtual tours. Select the "Virtual Tour" button below a listing to view the tour. Keep in mind, some listings may have virtual tours coming soon! 

Bennington Homes for Sale with Virtual Tours

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1086 West Road Bennington VT 05201

Bennington, VT1086 West Road

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4905858

  • Residential Single Family
  • Square Feet 6,956
  • Bedrooms 9
  • Bathroom 7
  • Construction Existing

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining pantry, formal dining and living rooms. The private estate includes a three car garage, four bedroom caretakers cottage, artist studio and gunite in-ground pool. Set on the outskirts of the historic town of Bennington offering shopping, live theatre, restaurants, horseback riding and proximity to mountain and cross-country skiing. This is a rare opportunity to own an exquisite estate property with a myriad of possibilities as a family compound or country retreat. Only 45 minutes to Albany International Airport and approximately three hours to Manhattan. All measurements approximate.

Listed by Chris DeFelice and Elena Atwill of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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257 Austin Hill Road Bennington VT 05201

Bennington, VT257 Austin Hill Road

Price$849,000

Est. Mortgage: $/month

MLS Number 4921198

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Square Feet 7,034
  • Bedrooms 5

This stunning contemporary home is all you could ever want and more! An easy drive to town, but why would you ever want to leave? A resort-like setting which includes a media room, large Rec Room with bar area, heated indoor swimming pool, golf range, and gorgeous stamped concrete patios with propane fire pit and Tiki torches! Practice your three point shot on your designated mini court, and store your toys in the oversized detached garage. Nothing has been overlooked inside either. Five beautiful bedrooms, three of which have private ensuite bathrooms. The primary suite is privately located on the second floor and includes a luxurious bathroom with a walk in closet, soaking tub, separate steam shower, double sinks and premium cabinetry. The living areas are all thoughtfully appointed with high end finishes. Vaulted ceilings and generous windows create bright and airy living spaces. An inviting and modern kitchen features top of the line appliances; separate freezer and refrigerator, steamer and convection ovens. The cabinets allow for plentiful storage and display options so you can live clutter free! The Rec Room is large and welcoming as it overlooks the pool and outdoor seating areas. A cozy media room for "movie nights" is a total bonus as well. These rooms flow seamlessly and make entertaining a breeze! Indoors or outdoors, this property was designed with comfort and casual luxury in mind. Enjoy the best of Vermont without sacrificing convenience!

Listed by Angela Bevin of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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195 Walloomsac Road Bennington VT 05201

Bennington, VT195 Walloomsac Road

Price$695,000

Est. Mortgage: $/month

MLS Number 4929131

  • Residential Single Family
  • Bathroom 4
  • Square Feet 3,870
  • Construction Existing
  • Bedrooms 3

In the shadows of the historic district of Bennington and the Bennington Battle Monument, there is a unique carriage house that emulates charm and character. This meticulously restored 1902 carriage house was once part of an estate that sits just adjacent to this special property. The grounds are lush, adorned with established gardens, mature plantings of trees, all highlighted with a gorgeous stone wall, built stone by stone by the current owner. The backyard is level, spacious and even includes a greenhouse for your plantings. Total acreage for this lovely home is 1.48 acres, enough to feel the beauty that surrounds and not overwhelmed by outdoor maintenance. Once inside this elegant home, you'll find three bedrooms and three and half baths, all spacious, all invitingly comfortable. The loft is a highlight that overlooks the first floor and provides additional living space to the first-floor family room that includes a gas burning fireplace for those chilly evenings. The kitchen is well built for the gourmet chef, but practical for family gatherings and meals. The kitchen flows easily to the formal dining room for entertaining, or family holidays. This enchanting property has a three-car garage, a workshop and a loft for storage. This is one of those special properties that rarely become available, come and see for yourself!

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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531 Apple Hill Road Bennington VT 05201

Bennington, VT531 Apple Hill Road

Price$549,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4913806

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 3,648
  • Bathroom 3
  • Construction Existing

This stately gambrel provides delightful views; historic Bennington Monument among the rolling hills or peruse the beautiful, established gardens, open lawn and stone walls. Two balconies and two covered porches are perfectly oriented to take in the setting. The house was thoughtfully designed and has been meticulously and lovingly cared for. The attached 2 car garage leads to the coveted Vermont “mudroom", past the full bath, an eat-in U-shaped kitchen, which flows to the formal dining room with a fireplace and access to the large front porch. The living room has floor to ceiling bookcases, a fireplace and direct access to yet another porch. From the kitchen or living room is an office/den making working from home private and convenient. The cheery foyer hosts the front door and takes you upstairs where you'll find a large common gathering room and appreciate the value of this space; with floor to ceiling built-ins, fireplace, with media viewing area, built-in desk and a game table area- truly a completely inviting space. An en suite bedroom has glass doors to a private balcony and 2 large closets. The bath includes a tiled shower, linen closet and double sinks. Guest bedrooms share a full bath, each with spacious closet, one with built-ins and private balcony.The lower level with endless pool and sauna is complimented with a semi finished rec/fitness room. Don't miss the 2 storage sheds, one with workshop area and a stand alone generator. A true gem! Showings begin 6/9/22.

Listed by Lavinia Lee Brown and Nancy Jensen of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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355 Elm Street Bennington VT 05201

Bennington, VT355 Elm Street

Price$530,000

Est. Mortgage: $/month

MLS Number 4930595

  • Residential Single Family
  • Bathroom 4
  • Square Feet 4,637
  • Bedrooms 4
  • Construction Existing

Lovely Brick Greek Revival home located on coveted Elm Street. This home has been carefully and tastefully renovated. A light filled foyer leads to a wonderful living room complete with wood burning fireplace perfect for entertaining. Spacious family room handsome gas fireplace with e Large dining room with easy access to a private three season porch and patio Renovated kitchen offers plenty of space. Bright breakfast room off kitchen with access to the three season room and patio. Master Suite with full bath, two additional bedrooms and one full bath, laundry room and powder room complete the first floor. Two car attached garage offers easy access to the kitchen, lovely one bedroom apartment that has its own private entrance. Great location with proximity to downtown, Southwestern Vermont Medical Center, Williamstown Ma and great skiing.

Listed by Moira Spivey of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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649 Walloomsac Road Bennington VT 05201

Bennington, VT649 Walloomsac Road

Price$529,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4920938

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,626

Gorgeous post and beam Adirondack style home situated on 2.27 acres overlooking Mount Anthony. Great spacious and airy design. 4 Bedrooms and 4 bathrooms including private primary suite. Modern kitchen, living room and dining room share a fireplace and open to each other and take in the views. Family room also has a fireplace and built-ins. Outside among the breathtaking views you'll find many plantings, fruit trees and flowers. A great find! Showings to begin 7/20/2022.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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210-214 Main Street Bennington VT 05201

Bennington, VT210-214 Main Street

Price$425,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4912983

  • Multifamily
  • Village Bennington
  • Units 3
  • Acreage 0.28
  • Square Feet 4,410

Wonderful investment opportunity. Located within walking distance to downtown Bennington and the Four Corners and Putnam Block Project. Convenient access to Southwestern Vermont Medical Center, banks and post office. The property includes 3 units. Two three bedroom 1 1/2 baths and one 2 bedroom 1 bath unit. Property includes 6 off street parking spaces and a fenced backyard and lovely front porch. Fully compliant with Bennington regulations and has both handicapped access and a fully compliant sprinkler system.

Listed by Moira Spivey of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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795 Camp Road Bennington VT 05201

Bennington, VT795 Camp Road

Price$379,000

Est. Mortgage: $/month

MLS Number 4929733

  • Residential Single Family
  • Bathroom 1
  • Square Feet 720
  • Construction Existing
  • Bedrooms 2

Chartered in 1749, Bennington was the first town created in Vermont. In June of 1761 twenty-two settlers from Massachusetts came to the wilderness of Vermont in Old Bennington. Nestled in that wilderness, you will find this unique, charming cabin on over 156 acres! Thirty years ago the owners of this property created a dream get away and are now ready to pass the torch (or the s'more stick!) to new owners. Relax on the front porch while taking in the Green Mountain view. Hike, hunt, paint, grill, shoot cans with a BB gun, build a fire, enjoy apples from the apple tree, find the area swimming holes, simply put, breath in the fresh air. This scenic, hidden treasure is tucked away between the hills and the mountains, beckoning those who are looking for that perfect, quiet escape to the Vermont wilderness, a secluded drive away from all the hustle and bustle of the rest of the world, surrounded by hard and soft woods and rolling hills. There is no plowing in the winter so three season or snow mobile or snow shoe in! Taxes are based on the current use program which the land is currently in. This property does not qualify for a conventional loan but does for a camp loan with 25% down.

Listed by Carrie Mathews of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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357 Chapel Road Bennington VT 05201

Bennington, VT357 Chapel Road

Price$349,900

Est. Mortgage: $/month

MLS Number 4931822

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,308

Best of both worlds! This beautiful property consists of two lots totaling more than 10 acres with mountain views and a picturesque barn. A peaceful and private retreat yet so close to town amenities! The house is warm and inviting with beautiful wood details. Heated mudroom, front porch is insulated and heated for bright, extra living space. One garage space underneath house, carport and parking space in pole barn. Oil furnace with backup wood furnace or vice versa! One of the sellers is an arborist so a list of perennials/plantings will be available.

Listed by Nancy Stagnitti of Mahar McCarthy Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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2080 Harwood Hill Road Bennington VT 05201
Active With Contract

MLS Number 4901598

  • Multifamily
  • Units 4
  • Bathroom 4
  • Acreage 17.55
  • Square Feet 3,412

GREAT OPPORTUNITY to own a four unit with 17+ acres. The main level of this center hall colonial has over 2000 square feet with a working fireplace, gorgeous wood floors, large eat-in kitchen, three bedrooms and one bath. Separate laundry room and its own covered porch. Upstairs has two units with private entrances, each are one bedroom. The last unit is a one-bedroom ranch style home with a large deck to enjoy. Come take a look!!!

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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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120 Convent Avenue Bennington VT 05201

Bennington, VT120 Convent Avenue

Price$284,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4932003

  • Residential Single Family
  • Bedrooms 5
  • Square Feet 3,288
  • Bathroom 3
  • Construction Existing

Spacious Center Hall Colonial with detached 2-car garage and paved driveway. Walkable to downtown, schools, museum and the Monument. Inside you'll find hardwood and tile floors throughout. Main floor has Living room with brick fireplace, a formal dining with modern chandelier, den/office with pellet stove, large eat-in kitchen with island, laundry room, and a colorful powder room. Upstairs are five bedrooms and two full bathrooms, and the most beautiful staircase I've ever seen. Finished 3rd floor offers bonus rooms for office, studio, storage and more. Heating system is oil hot water baseboard with a newer Buderus boiler; sellers love supplementing with the pellet stove for that cozy warmth. On town water and sewer. Work from home is a breeze with Comcast Xfinity high-speed internet, as well as other providers available. Enclosed front and rear porches offer the much-desired mudroom, and additional living spaces for you, your pets or plants! Sprawling yard with 0.62 acres and abundant sunlight. There's a basketball court, swings, chicken coop, and a partially fenced area to keep your pets close to home. It's a lot of house, awesome location, and a great deal for the right buyer!

Listed by Jenifer Hoffman of Hoffman Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

101 Observatory Street Bennington VT 05201
Active With Contract

MLS Number 4926063

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 1,428
  • Construction Existing
  • Bathroom 2

Fall in love with this picture perfect ranch just steps away from the hospital, walking and biking trails, and the center of town. Three bedrooms and two bathrooms, a spacious living room with a wood burning fireplace, and a bright galley kitchen all on a single level. The genious of this home is the thoughtful split floor plan. Two generous bedrooms share a bathroom on one end, while the primary suite with its own bathroom is on the other end. At one point the primary suite was converted into an efficiency unit, so there's great potential for those needing an in-law suite or home office space. A lovely enclosed porch is the perfect spot to enjoy your morning coffee, or relax after a long day. Featuring a one car garage and a carport, this great property is as attractive as it is functional. Meticulously maintained and cared for, there's nothing that needs attention. The yard is nicely landscaped and has plenty of space for outdoor fun. You will most definitely be proud to call this your Home Sweet Home!

Listed by Angela Bevin of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 6, 2022 6:54 AM EDT.

 
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