Homes for Sale near Grace Christian School

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  /50

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft

  55 Monument Ave, Bennington, VT 05201

  Step back in time while enjoying modern comforts in this stunning c. 1787 Colonial home located in the heart of Old Bennington. Brimming with character and charm, this 3BR/3BA residence combines historic elegance with contemporary updates for today’s lifestyle. Inside, you’ll find a brand-new chef’s kitchen designed for culinary enthusiasts, complete with high-end appliances and ample counter

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 849-4742

  55 Monument Ave, Bennington, VT 05201
• 

  

  

  /22

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft

  203 Northside Dr, Bennington, VT 05201

  Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 471-3591

  203 Northside Dr, Bennington, VT 05201
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  /46

  $850,000

  • 5 Beds
  • 2 Baths
  • 2,424 Sq Ft

  2 Cold Spring Rd, North Bennington, VT 05257

  Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 810-8434

  2 Cold Spring Rd, North Bennington, VT 05257
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  /41

  $295,000

  • 5 Beds
  • 2 Baths
  • 2,418 Sq Ft

  226 North St, Bennington, VT 05201

  This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 327-7149

  226 North St, Bennington, VT 05201
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  /72

  $339,000

  • 4 Beds
  • 2 Baths
  • 2,203 Sq Ft

  167 Burgess Rd, Hoosick Falls, NY 12090

  Step back in time as you arrive at this countryside paradise offering majestic views of Vermont's Green Mountains. This mini farm retains original charm showcasing rare original woodwork, hardwood floors a built-in pass-through and a classic rocking chair front porch with breathtaking views that stretch for miles. Outside, the rolling pastures prime farmland amazes you, and you will also find a

  Richard Tinkham Berkshire Hathaway Home Services Blake

  167 Burgess Rd, Hoosick Falls, NY 12090
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  /48

  $325,000

  • 4 Beds
  • 3 Baths
  • 2,994 Sq Ft

  165 Pippin Knoll, Bennington, VT 05201

  Set well back from the road, this mid-century modern home emphasizes simple lines, an indoor-outdoor connection, and panoramic views. The main level centers on an open living/dining/kitchen area anchored by a fireplace and oversized windows that overlook the pond and rolling landscape beyond. The primary suite on this level provides private comfort. A second-floor bedroom offers a rare

  Kelley Mccarthy Mahar McCarthy Real Estate

  165 Pippin Knoll, Bennington, VT 05201
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  /35

  $475,000

  • 5 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  115 Grandview St, Bennington, VT 05201

  Step into timeless elegance with this beautifully restored Victorian home, showcasing stunning woodwork and thoughtful updates throughout. This spacious residence offers five bedrooms, one being on the first floor, and two updated bathrooms blending classic character with modern comfort. A whimsical hidden quarter bath under the stairs adds both charm and function. The home’s gracious

  Cassie Barbeau Mahar McCarthy Real Estate

  115 Grandview St, Bennington, VT 05201
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  /43

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  683 Water St, North Bennington, VT 05257

  Completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
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  /30

  $349,995

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  374 Overlea Rd, North Bennington, VT 05257

  A stunning three bedroom, two bath home on a wooded lot with mountain views and bordered on several sides by serene farm pastures! Just a few minutes from downtown Bennington and even closer to the village of North Bennington! Tons of natural light inside that compliments the updated kitchen and open dining / living room areas. First floor includes enclosed rear sun porch/mudroom, laundry and

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
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  /36

  $399,000

  • 5 Beds
  • 3 Baths
  • 3,118 Sq Ft

  100 McCarthy Acres, North Bennington, VT 05257

  Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

  Nicholas Charest Maple Leaf Realty

  100 McCarthy Acres, North Bennington, VT 05257
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  /45

  $350,000

  • 4 Beds
  • 1 Bath
  • 1,680 Sq Ft

  19 Royal St, North Bennington, VT 05257

  Charming North Bennington Home in a Desirable Neighborhood.Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College.Step inside to discover a freshly

  Lindsey Martin Maple Leaf Realty

  19 Royal St, North Bennington, VT 05257
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  /41

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  245 Southshire Dr, Bennington, VT 05201

  Nestled in one of Bennington's most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm--all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System(BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  245 Southshire Dr, Bennington, VT 05201
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  /50

  $374,900

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft

  927 Water St, North Bennington, VT 05257

  Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres.Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  927 Water St, North Bennington, VT 05257
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  /48

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 3,742 Sq Ft

  34 Southshire Dr, Bennington, VT 05201

  Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

  Kelley Mccarthy Mahar McCarthy Real Estate

  34 Southshire Dr, Bennington, VT 05201
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  /12

  $499,000

  • 6 Beds
  • 4 Baths
  • 15,179 Sq Ft

  423 Main St, Bennington, VT 05201

  Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor

  Chris Long BHG Masiello Brattleboro

  423 Main St, Bennington, VT 05201
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  /52

  $399,900

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft

  263 Elm St, North Bennington, VT 05257

  New Price! Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light graces this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining

  Margretta Fischer Wohler Realty Group

  263 Elm St, North Bennington, VT 05257
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  /35

  $575,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  704 Fox Hill Rd, Bennington, VT 05201

  House hunting in Vermont and can't find what you want? Or it sold before you had time to tour or think it through? This brand new custom built home could be the answer. Desirable neighborhood with paved town roads, close to SVMC hospital, Bennington College, downtown restaurants and events, and one hour from Albany Int'l Airport. Nestled at the base of Mount Anthony, there's direct access to

  Jenifer Prouty Hoffman Hoffman Real Estate

  704 Fox Hill Rd, Bennington, VT 05201
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  /31

  $219,000

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  50 Ledgely Dr, Shaftsbury, VT 05262

  Welcome to 50 Ledgely Drive, a charming and well-cared-for home located in one of Shaftsbury’s smaller neighborhoods. This 2 bedroom, 1 bath home is ideal for first-time buyers, downsizers, or anyone looking for a more manageable space with potential to grow. Solidly built and lovingly maintained over the years, this home offers great bones and a warm, inviting feel throughout. The efficient

  Erika Floriani Hoffman Real Estate

  50 Ledgely Dr, Shaftsbury, VT 05262
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  /21

  $120,000

  • Land
  • 20 Acres
  • $6,000 per Acre

  1319 Vail Rd, Bennington, VT 05201

  Discover an exceptional opportunity to build your dream home on this prime 20-acre parcel located in the desirable west end of Bennington. This expansive property offers a perfect blend of privacy and convenience, ready for immediate development.Key features of this remarkable land include an established driveway providing easy access to your future homesite, and a completed perk test

  Lilli West Maple Leaf Realty

  1319 Vail Rd, Bennington, VT 05201
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  /15

  $269,000

  • 2 Beds
  • 1 Bath
  • 2,500 Sq Ft

  624 Main St, Bennington, VT 05201

  Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

  Kelley Mccarthy Mahar McCarthy Real Estate

  624 Main St, Bennington, VT 05201
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  /26

  $234,900

  • 4 Beds
  • 2 Baths
  • 1,278 Sq Ft

  215 Maple St, Bennington, VT 05201

  Enjoy the charm and comfort of this beautifully renovated home, ideally nestled in the heart of Bennington. As you arrive, you'll be greeted by a spacious front porch, perfect for relaxation, entertaining, and enjoying cool breezes. This property has undergone a complete transformation from a two-family to a stunning single-family home. It now offers convenient one-floor living. The first floor

  Matt Waddington Hoffman Real Estate

  215 Maple St, Bennington, VT 05201
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  /8

  $59,000

  • Land
  • 0.29 Acre
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
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  /10

  $245,000

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  209 Grove St Unit 11, Bennington, VT 05201

  Well-maintained 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, an eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice backyard, 2 covered parking spaces

  Julie Glover Mahar McCarthy Real Estate

  209 Grove St Unit 11, Bennington, VT 05201
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  /27

  $134,950

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  3 Farmers Inn Rd, Hoosick Falls, NY 12090

  🔥 NEW PRICE - This Charming 4-Bed, 2-Bath Farmhouse delivers 1,728 SF of flexible space loaded with potential. Formerly a two-family—now a spacious single-family—giving you endless options for multi-gen living or income potential. Huge 5-bay detached garage with workshop is a rare find and perfect for car enthusiasts, contractors, or serious storage needs. Relax on the oversized front

  Kelly Sharifipour Darby Real Estate of New York Inc

  3 Farmers Inn Rd, Hoosick Falls, NY 12090
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  /28

  $279,000

  • 9 Beds
  • 3 Baths
  • 3,176 Sq Ft

  26 Sage St, Bennington, VT 05257

  A wonderful investment opportunity in the desirable village of North Bennington! This income-producing property with three units has been well kept and updated over the years - most recently with a brand new roof. Two of the three-bedroom units have been freshly renovated and all are currently occupied with a strong rental history. Two of the units have two stories, giving it a townhouse feel,

  Lilli West Maple Leaf Realty

  26 Sage St, Bennington, VT 05257
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  /14

  $470,000

  • 3 Beds
  • 7 Baths
  • 2,148 Sq Ft

  106 School St, Bennington, VT 05201

  Investors take note. This 7 unit building features three one bedroom units and four studio units. Tenants pay their own electric and internet. The boiler servicing the building is an efficient pellet boiler. The hot water is also pre-heated with solar to help keep costs low. Five of the units have been updated in the past several years. At current rents and assumed 100% occupancy the building

  William Paquin Maple Leaf Realty

  106 School St, Bennington, VT 05201
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  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs.Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
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  /18

  $147,000

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft

  432 South St Unit C6, Bennington, VT 05201

  A fresh perspective on easy living! Welcome to this beautifully maintained 2BR/1.5 BA second-floor condo in Nathanial Court offering the perfect blend of comfort, convenience, and low-maintenance living. Step into a bright and airy open floor plan, where large windows flood the space with natural light. The tidy kitchen boasts ample cabinet space, sleek stainless steel appliances, and a clean

  Angela Bevin Maple Leaf Realty

  432 South St Unit C6, Bennington, VT 05201
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  /16

  $145,000

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft

  755 Main St, Bennington, VT 05201

  Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  755 Main St, Bennington, VT 05201
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  /19

  $219,500

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft

  14 Robinson Ave, Bennington, VT 05201

  Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

  Timothy Corcoran Mahar McCarthy Real Estate

  14 Robinson Ave, Bennington, VT 05201
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  /2

  $225,000

  • 6 Beds
  • 2 Baths
  • 2,112 Sq Ft

  303-305 Gage St, Bennington, VT 05201

  Low maintenance duplex in Bennington. Offering good rental history and income. 2 -3 bedroom units, newer systems, vinyl siding and more. Walking distance to town. schools and recreation.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  303-305 Gage St, Bennington, VT 05201
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  /4

  $249,000

  • 5 Beds
  • 3 Baths
  • 2,184 Sq Ft

  137 Park St, Bennington, VT 05201

  Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  137 Park St, Bennington, VT 05201
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  /10

  $1,950,000

  • Land
  • 7 Acres
  • $278,571 per Acre

  720 N Branch St, Bennington, VT 05201

  Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street.The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit

  Paul Carroccio TPW Real Estate

  720 N Branch St, Bennington, VT 05201
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  /44

  $69,900

  • 5 Beds
  • 1 Bath
  • 1,952 Sq Ft

  273 Union St, Bennington, VT 05201

  This village property has great bones and potential!! First floor includes generously sized kitchen, formal dining room and living room as well as a small office offering the opportunity to expand the full bath to include laundry. The second floor includes four bedrooms including a primary that has a sitting area/dressing room/nursery, whatever suits your needs. Separate barn that while

  Catherine Cairns Maple Leaf Realty

  273 Union St, Bennington, VT 05201
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  /31

  $150,000

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  109 Evergreen Dr, Bennington, VT 05201

  House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
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  /11

  $179,900

  • 4 Beds
  • 2 Baths
  • 2,643 Sq Ft

  905 County St, Bennington, VT 05201

  Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  905 County St, Bennington, VT 05201
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  /42

  $795,000

  • 5 Beds
  • 1.5 Baths
  • 2,450 Sq Ft

  126 Fox Hill Rd, Bennington, VT 05201

  Welcome to this stunning 1850s home, perfectly sited on 2.72 acres with breathtaking mountain views. With 5 bedrooms, 2 full baths, and over three decades of loving ownership, this property offers the perfect blend of historic charm and modern updates in a peaceful, scenic setting.Inside, you'll find spacious, light-filled rooms enhanced by large windows and a calming palette of neutral

  Kelley Mccarthy Mahar McCarthy Real Estate

  126 Fox Hill Rd, Bennington, VT 05201
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  /42

  $1,950,000

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  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

  Chris DeFelice Four Seasons Sotheby's Int'l Realty

  1086 West Rd, Bennington, VT 05201
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  /7

  $175,000

  • Land
  • 15.49 Acres
  • $11,298 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision.Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
• 

  

  /52

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities.

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201

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