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Bennington VT Real Estate

Historic Bennington, Vermont is the largest town in Southern Vermont, situated between the Taconic and Green Mountains in southwestern Vermont, not far from Massachusetts and Albany, New York. Bennington is a thriving community with a rich history, beautiful architecture, locally owned businesses, and small-town charm. Fall in love with a Bennington home and discover Southern Vermont.

Search the latest real estate in Bennington, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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You may also be interested in browsing all Bennington County real estate listings.

160 Benmont Avenue Bennington VT 05201

Bennington, VT160 Benmont Avenue

Price$5,000,000The price has recently decreased

MLS Number 4888929

  • Commercial
  • Year Built 1865
  • Acreage 10.7

Opportunity of a lifetime! Imagine owning one of America's largest historic mills? Built in 1865 additions into 1935 and strategically placed in the heart of the thriving Bennington town, this mill began with Civil war uniforms, then continued as a woolen mill for decades, went on to become a knitting factory and a paper mill too. In the early 1900's over 1/3 of the area was employed here. Since the current owner invested into in the 1980's and 90's, it has continued to grow and is now a booming mixed use building nearly at full occupancy creating space for medical and counseling offices, College classrooms, Gyms and health oriented spaces, Manufacturing companies, design studios, attorney offices, retails stores, auto work, graphic designers, artist studios, storage spaces and even housing! You name it, it can be done here. The potential is unlimited. There is a huge need for housing in our area and the prospect for condo units in this place is viable. To rebuild this incredible structure with the wood beams, steel infrastructure and brick construction would cost over 25 million in todays dollars. The entire building has been updated with electrical, plumbing, heating and an elevator system. With all the new, there is still so much character from the many lifetimes this property has traveled through. The outbuildings in the back could be sold for hundreds of thousands of dollars themselves if listed separately. With nearly 11 acres and plenty of parking plus river frontage!

Listed by Lillian West of Maple Leaf Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

230 School Street Bennington VT 05201

Bennington, VT230 School Street

Price$3,050,000The price has recently decreased

MLS Number 4831584

  • Commercial
  • Acreage 3

This is your chance to own an established multi-sport training/camp facility in downtown Bennington, Vermont. The former Catamount School has been converted and refurbished as a sports training complex. Space including several indoor turf facilities, full cafeteria, dorm rooms, parking, and outdoor fields - this facility is ready and turn key! Whether you want to run a soccer, lacrosse, basketball, baseball, or any other sport camp or training operation - this is the place for you. In addition, there is unused indoor space ready for expansion! The former Catamount School with street footage on route 7 is available separately. Also included in sale is all kitchen equipment, furnishings, sporting equipment, and facility maintenance tools/equipment.

Listed by Paul William Carroccio and Marek Kovac of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

141 West Main Street Bennington VT 05201

Bennington, VT141 West Main Street

Price$2,990,000The price has recently decreased

MLS Number 4834579

  • Commercial
  • Year Built 1963
  • Acreage 4.29

Turn key operation, development opportunity, you decide! Large and loyal clientele. Elegant property. Owner home on site. No commute to work. First time offered. PRICED TO SELL! The Paradise Motor Inn is located in Bennington, Vermont. Don't miss on this unique opportunity to own one of the finest hospitality establishments in the heart of Southern Vermont. The property is well maintained and offers a variety of added values and experiences: extensive gardens and lawns, tennis courts, pool, pickle ball. Ski, golf, hike, all within a few miles from the Inn.

Listed by Marek Kovac and Paul William Carroccio of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

217-219 Northside Drive Bennington VT 05201

Bennington, VT217-219 Northside Drive

Price$1,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4853014

  • Land
  • Village Bennington
  • Acreage 3.25
  • Zoning Planned Commercial

NOW INCLUDES both the bowling alley & dairy bar! With 3.25 acres on Northside Drive, one of Bennington County's busiest roads (14K cars daily). Close to major shopping centers, hotels/motels, restaurants, etc. Easily accessed by all major highways (Rt 7, 7A, 67A, 279 bypass). Two successful businesses ready for new owner to take the reins. Premier location for any business. Zoning with DRB approval includes but is not limited to: retail, restaurant, indoor recreation, self storage, car wash, daycare, financial institution, gas station, hotel, medical clinic, motor vehicle sales and service, RV park, business office, and warehouse. Originally built as a bowling alley, and taken over by current owner 40 years ago, and invested in substantial improvements consistently. Modern interior design, new pins bought last year, everything front & back is computerized, including sound & security systems. Two state-of-the-art high-definition golf simulators bring in a different crowd and stream of revenue. Full kitchen with gas range, fryers, flat top, proper hood ventilation, freezers, and adjacent storage room. Bar has 2 beer coolers and 8-tap kegerator. Two accessible restrooms, janitorial room, security office, utility room, mechanics workshop, attached garage. Includes most furniture, fixtures, and equipment. Billy T's Northside Dairy Bar is a local hotspot, serving favorite foods & ice cream all summer long. Oversized storage building, plus 2 rentals generating $1250/month income.

Listed by Jenifer Hoffman of Hoffman Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

217-219 Northside Drive Bennington VT 05201

Bennington, VT217-219 Northside Drive

Price$1,500,000The price has recently decreased

MLS Number 4853013

  • Commercial
  • Village Bennington
  • Year Built 1954
  • Acreage 3.25

NOW INCLUDES both the bowling alley & dairy bar! With 3.25 acres on Northside Drive, one of Bennington County's busiest roads (14K cars daily). Close to major shopping centers, hotels/motels, restaurants, etc. Easily accessed by all major highways (Rt 7, 7A, 67A, 279 bypass). Two successful businesses ready for new owner to take the reins. Premier location for any business. Zoning with DRB approval includes but is not limited to: retail, restaurant, indoor recreation, self storage, car wash, daycare, financial institution, gas station, hotel, medical clinic, motor vehicle sales and service, RV park, business office, and warehouse. Originally built as a bowling alley, and taken over by current owner 40 years ago, and invested in substantial improvementsconsistently. Modern interior design, new pins bought last year, everything front & back is computerized, including sound & security systems. Two state-of-the-art high-definition golf simulators bring in a different crowd and stream of revenue. Full kitchen with gas range, fryers, flat top, proper hood ventilation, freezers, and adjacent storage room. Bar has 2 beer coolers and 8-tap kegerator. Two accessible restrooms, janitorial room, security office, utility room, mechanics workshop, attached garage. Includes most furniture, fixtures, and equipment. Billy T's Northside Dairy Bar is a local hotspot, serving favorite foods & ice cream all summer long. Oversized storage building, plus 2 rentals generating $1250/month income.

Listed by Jenifer Hoffman of Hoffman Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

North Street Bennington VT 05201

Bennington, VTNorth Street

Price$1,450,000The price has recently decreased

MLS Number 4894343

  • Commercial

This is your chance to own the former Catamount School on Route 7 in Bennington, VT. This property includes road frontage on Route 7, building and improvements. The property is currently deeded together with the property on 230 School street, but will be subdivided in accordance with Purchaser and Seller's agreement on lot lines and easements. Entire property also available for sale under different MLS#4831584.

Listed by Paul William Carroccio and Marek Kovac of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

604 US Route 7 South Bennington VT 05201

Bennington, VT604 US Route 7 South

Price$1,450,000The price has recently decreased

MLS Number 4894235

  • Commercial
  • Acreage 19

Our beloved Apple Barn of Bennington, Vermont is now available for sale. After over fifty years of a family business, the owner is now retiring. This business is known to many from near and afar, searching for the best baked goods, maple syrup and an eclectic retail shop. Known for it's apple cider donuts, holiday pies and fresh apples from the owners apple orchard, this business is thriving and ready for a new proprietor. Open seasonally, the Apple Barn has the potential to produce business all year long, with the possibility of serving a broader spectrum of food to its patrons. The building stands 5600 square feet and is kept impeccably clean, maintained and includes all equipment, fixtures, bakery and ice cream cases and much more. Included on the 19 acres is a farm that yields berries and vegetables, all which are sold for retail in the spacious barn. The business is situated on VT Route 7 close to downtown Bennington and is the stopping point for many traveling on this busy road. This is a dream opportunity for the right buyer, or individual ready to take on a family business.

Listed by Monique Geannelis of Mahar McCarthy Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Kocher Drive Bennington VT 05201

Bennington, VTKocher Drive

Price$1,200,000The price has recently decreased

MLS Number 4689141

  • Commercial
  • Acreage 12

This open, flat parcel is adjacent easterly of The Bennington Square Shopping Center with Penny's, Staples, HallMark Gift Shop, Olympia Sports, and Label Shopper. There is a free standing Burger King and Peoples United Branch Bank located on either side of the front entry. Plans are underway for the new owner Ocean State Job Lot of the shopping center to open one of their stores at this location. Traffic Count at the junction of Route 7 North and Kocher Drive is the highest count in the area with 13,700 vehicles recorded on an average per diem. The property is zoned commercial with all community utilities available at the street.

Listed by Kathleen Hoisington of Hoisington Realty,Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

300 Gage Street Bennington VT 05201

Bennington, VT300 Gage Street

Price$845,000The price has recently decreased

MLS Number 4894756

  • Commercial
  • Year Built 1800
  • Acreage 0.18

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

108 Northside Drive Bennington VT 05201

Bennington, VT108 Northside Drive

Price$799,000The price has recently decreased

MLS Number 4894911

  • Commercial
  • Year Built 1958
  • Acreage 2.04

Having one of the highest traffic counts in the town this location is ideal for chain drug store, fast food, convenience store, small strip mall or other retail location wanting to take advantage of great daily traffic count. Presently there is a former auto dealer building on the premises.

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

100 & 120 Depot Street Bennington VT 05201

Bennington, VT100 & 120 Depot Street

Price$795,000The price has recently decreased

Active With Contract

MLS Number 4866505

  • Commercial
  • Year Built 1962
  • Acreage 1.7

A wonderful business opportunity in a well-trafficked area in the heart of Bennington. Great visibility and plenty of parking. Consists of five units totalling 22,900 square feet on a 1.7-acre parcel. There's room to move your business here while supplementing your income with rent from existing tenants.

Listed by Kathleen Hoisington of Hoisington Realty,Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

338 Main Street Bennington VT 05201

Bennington, VT338 Main Street

Price$770,000The price has recently decreased

MLS Number 4850968

  • Commercial
  • Year Built 1931

Iconic property located in the center of historic Bennington, Vermont. This is a unique opportunity to live and/or work in a renovated former bank building in the heart of Downtown Bennington. Upstairs features a 4 bedroom, 2 bathroom 2,960sf penthouse residence with private entrance. Large windows overlook the Green Mountains, as well as the parades, events, and daily life of Four Corners. The ground and mezzanine levels feature approximately 3,700sf of elegant commercial space suitable for retail, professional, office, restaurant, etc... Creative use of the property might include using the upstairs as your residence while leasing the commercial space downstairs, or keep the commercial space for your own business. This landmark property has been meticulously preserved with original ornate moldings, polished brass chandeliers, ceiling medallion, marble floor, three working vaults, and imported marble teller counter. Its neoclassical facade boasts Vermont marble and copper details. Located directly across the street from the $50 million Putnam Block redevelopment project, which includes residential, office, restaurant, and retail spaces (occupancy began in January 2021). Adjacent to two beautiful new parks. The prime location puts you close to world class skiing, 1 hour to Albany, 3 hours to Boston, and 3.5 hours to New York City.

Listed by Jason Saphire of www.HomeZu.com

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

338 Main Street Bennington VT 05201

Bennington, VT338 Main Street

Price$770,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4828352

  • Residential Single Family
  • Square Feet 6,650
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4

Iconic property located in the center of historic Bennington, Vermont. This is a unique opportunity to live and/or work in a renovated former bank building in the heart of Downtown Bennington. Upstairs features a 4 bedroom, 2 bathroom 2,960sf penthouse residence with private entrance. Large windows overlook the Green Mountains, as well as the parades, events, and daily life of Four Corners. The ground and mezzanine levels feature approximately 3,700sf of elegant commercial space suitable for retail, professional, office, restaurant, etc... Creative use of the property might include using the upstairs as your residence while leasing the commercial space downstairs, or keep the commercial space for your own business. This landmark property has been meticulously preserved with original ornate moldings, polished brass chandeliers, ceiling medallion, marble floor, three working vaults, and imported marble teller counter. Its neoclassical facade boasts Vermont marble and copper details. Located directly across the street from the $50 million Putnam Block redevelopment project, which includes residential, office, restaurant, and retail spaces (occupancy began in January 2021). Adjacent to two beautiful new parks. The prime location puts you close to world class skiing, 1 hour to Albany, 3 hours to Boston, and 3.5 hours to New York City.

Listed by Jason Saphire of www.HomeZu.com

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

59 HARWOOD HILL Road Bennington VT 05201

Bennington, VT59 HARWOOD HILL Road

Price$649,000The price has recently decreased

MLS Number 4867182

  • Commercial
  • Year Built 1970
  • Acreage 0.62

Opportunity to own a newly renovated climate control storage facility with loading dock and multi-tenant office/storage building on Northside Drive and Harwood Hill in Bennington, Vermont. The property includes two parcels totaling 0.62 acres with the opportunity for more construction/buildings/parking, etc. Current cash flow from tenants supports a 8% cap rate and continues to improve. New HVAC, dividing walls, flooring, lighting, and much much more!

Listed by Paul William Carroccio and Marek Kovac of TPW Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

757 Main Street Bennington VT 05201

Bennington, VT757 Main Street

Price$595,000The price has recently decreased

MLS Number 4894520

  • Commercial
  • Acreage 1.37

A great old brick factory building with huge potential. The first floor is currently rented out to an antique/used furniture store and a machine shop. The vast second floor is vacant. Bring your ideas: loft apartments, a studio, a maker's space... the possibilities are limited only by your imagination! There's plenty of parking, with spaces out front and more behind the building.

Listed by Phil Lewis of Mahar McCarthy Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

704 Main Street Bennington VT 05201

Bennington, VT704 Main Street

Price$575,000The price has recently decreased

MLS Number 4888335

  • Commercial
  • Acreage 0.1

Unique opportunity to own a full downtown business and multi unit property. Love-A-Bagel is for sale. It will include all equipment and inventory. In addition there is a fully rented office space and 3 upstairs residential 1 bedroom units. A great opportunity for investment. Well known business and location.

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

226-228 Northside Drive Bennington VT 05201

Bennington, VT226-228 Northside Drive

Price$550,000The price has recently decreased

MLS Number 4865526

  • Commercial
  • Acreage 1.78

Approx. 200 sq. ft. Feed Store and Salon sits on lot #19 on the corner of Northside Drive and Harmon Road. An unoccupied three bedroom 1500 sq. ft. home with detached barn/garage and mobile home currently sits on lot #16. To the left of lot 16 is an entrance driveway to Price Chopper, Walmart Shopping Center. Super Walmart, Chili's Restaurant , Hampton and numerous car dealerships reside on this corridor. Other business established in the area are Pizza Hut, Dunkin Donuts, McDonalds, Cumberland Farms and Home Depot. Road Frontage 237' on Northside Drive, 270' on Harmon Road. Zoning Cl-40 Planned Commercial.

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

722 Main Street Bennington VT 05201

Bennington, VT722 Main Street

Price$529,000The price has recently decreased

MLS Number 4884403

  • Commercial
  • Year Built 1774
  • Acreage 0.74

A unique opportunity to become the next steward of one of Bennington's most relevant historic properties. Built in 1774 by Joseph Safford for his son, Samuel Safford, and known as the oldest standing home in the east village, this notable property currently operates as a quintessential Vermont Inn but could easily be returned to a single family home, used as a therapeutic facility or provide distinguished office space. 4 fully renovated guest bedrooms w/private baths, each thoughtfully designed and outfitted for guest comfort while preserving historic detail and charm. The additional 5 bedrooms, 5 bathrooms and 3 kitchens, include 2 main level kitchens, a 2nd floor owner apartment w/private entry/kitchen/living/dining, as well as a private inn keeper suite and the potential to convert more bedrooms to inn, office or common space. Recent updates include, Buderus multi zone boiler, oil tank, plumbing, electric and driveway, along with ongoing exterior maintenance. Offered fully furnished with business essentials. Ideally located, walk-able to downtown Bennington but also close proximity to Williamstown, Manchester and nearby ski towns means fun, food and culture in every direction for yourself or guests! 1 hour from Albany Airport, 3 hours to NYC and Boston. This prestigious property has been lovingly maintained by only 4 previous owners, it's your turn to become part of Vermont history!

Listed by Abi Gregorio of Maple Leaf Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

722 Main Street Bennington VT 05201

Bennington, VT722 Main Street

Price$529,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4884362

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Square Feet 4,995

A unique opportunity to become the next steward of one of Bennington's most relevant historic properties. Built in 1774 by Joseph Safford for his son, Samuel Safford, and known as the oldest standing home in the east village, this notable property currently operates as a quintessential Vermont Inn but could easily be returned to a single family home, used as a therapeutic facility or provide distinguished office space. 4 fully renovated guest bedrooms w/private baths, each thoughtfully designed and outfitted for guest comfort while preserving historic detail and charm. The additional 5 bedrooms, 5 bathrooms and 3 kitchens, include 2 main level kitchens, a 2nd floor owner apartment w/private entry/kitchen/living/dining, as well as a private inn keeper suite and the potential to convert more bedrooms to inn, office or common space. Recent updates include, Buderus multi zone boiler, oil tank, plumbing, electric and driveway, along with ongoing exterior maintenance. Offered fully furnished with business essentials. Ideally located, walk-able to downtown Bennington but also close proximity to Williamstown, Manchester and nearby ski towns means fun, food and culture in every direction for yourself or guests! 1 hour from Albany Airport, 3 hours to NYC and Boston. This prestigious property has been lovingly maintained by only 4 previous owners, it's your turn to become part of Vermont history!

Listed by Abi Gregorio of Maple Leaf Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

203-205 Northside Drive Bennington VT 05201

Bennington, VT203-205 Northside Drive

Price$525,000The price has recently decreased

MLS Number 4888449

  • Commercial
  • Year Built 1998
  • Acreage 0.64

Established commercial property on prime location just before the traffic circle for Wal-Mart and Price Chopper Plaza. 2 family residential could be converted to whatever use needed. Currently rented as a single family. Large building in back renovated in the 2000's has been the home to Sheer Jazz beauty salon and is a well loved business and tenant. the front part of the building is a retail office space. In the past has been a video store and real estate office. The large barn in back is great for storage. Plenty of wooded area behind the building if more parking was ever needed. Neighbors with Pizza hut. Paved driveway. Well maintained for decades. Now an opportunity for you.

Listed by Lillian West of Maple Leaf Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

55 Monument Avenue Bennington VT 05201

Bennington, VT55 Monument Avenue

Price$485,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4884333

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

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

139 West Main Street Bennington VT 05201

Bennington, VT139 West Main Street

Price$451,250The price has recently decreased

MLS Number 4834580

  • Commercial
  • Year Built 1977
  • Acreage 0.53

Great location, commercial retail/hospitality opportunity. Solid rental/lease history. First time offered. PRICED TO SELL! Don't miss on this unique opportunity to own a great property in the Village of Bennington. The property is well maintained and offers a variety of added values and experiences: proximity to downtown Bennington, street sign presence.

Listed by Marek Kovac and Paul William Carroccio of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

819-823 Main Street Bennington VT 05201

Bennington, VT819-823 Main Street

Price$419,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 4867399

  • Multifamily
  • Square Feet 5,374
  • Units 6
  • Bathroom 6
  • Acreage 0.26

It's a rare find! A brick Italianate in excellent condition. The gorgeous wrap around porch and marble sidewalk welcomes you in. It's been converted into 6 rental units. They are all up to current code while keeping the integrity of the original details and charm. You will find yourself saying ooh an ahh as you walk through this lovely property. Basement and structural is incredible 9they don't build them like they used to!) It's very easy to find tenants (waiting list in fact) for these lovely units. The cash flow covers all the expenses and brings in great cash flow. Lovely east Main Street location.

Listed by Lillian West of Maple Leaf Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

213 Jefferson Heights Bennington VT 05201

Bennington, VT213 Jefferson Heights

Price$399,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 4892258

  • Residential Single Family
  • Square Feet 2,184
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

Gorgeous 3 bedroom, 2 and a half bath ranch with finished basement in a great neighborhood. Offering large living room, modern kitchen with updated appliances and granite countertops, large dining area, master bedroom suite with brand new bathroom and walk-in closet, 2 additional main level bedrooms and full bathroom. The full walkout basement is beautifully finished with a family room with gas stove, an additional room that could serve many functions, utility and laundry room and a half bath. Additionally this home has an oversized 2 car basement garage, sunset watching deck, full fenced yard, in ground pool with pool heater, built-in gas firepit with improved fire ring. House has "smart" enabled with Lutron light switches, Nest smoke and carbon monoxide detectors, Nest doorbell and Nest thermostats, all you need are your hubs.

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

748 Main Street Bennington VT 05201

Bennington, VT748 Main Street

Price$375,000The price has recently decreased

MLS Number 4891494

  • Commercial
  • Year Built 1944
  • Acreage 0.57

This well-located commercial property enjoys great accessibility and visibility on East Main Street/Rte. 9. There are three strong tenants in place with one additional vacancy ready to be filled. 22 onsite parking spaces plus 10 deeded additional spaces across the street for a total of 32. The current tenants include Domino's Pizza, Jon E. Suds laundromat, and New Beginnings Hair Salon. The total building square footage including a vacant second floor office space, is 8,100 SF. The present vacancy on the ground floor is 1,680 SF.

Listed by Paul Harsch of Harsch Associates

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.56% last updated on 2022-01-20

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2022 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 January 23, 2022.

 

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