Properties Near 58 Mount Anthony Road Bennington, VT

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 colors throughout. The main level boasts beautiful hardwood floors, a formal living room, and an elegant dining room -ideal for entertaining or family gatherings. The updated kitchen is both functional and stylish, complemented by a large island. The cozy family room features a gas fireplace and a stunning bay window that frames the natural beauty outside, making it a perfect space to relax year-round. Step out onto the architect-designed covered porch and take in the mountain views-it’s a tranquil retreat like no other. Outbuildings include a former four-stall horse barn, now used as excellent storage, and a second barn that has been transformed into a four-car garage with additional storage above -perfect for hobbies, vehicles, or workshop space. This rare property offers historic charm, modern comfort, and unbeatable views-an exceptional opportunity for those seeking space, serenity, and timeless New England character.

Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary suite on the main level provide convenience and flexibility. Upstairs, you’ll find two generous bedrooms, a full bath, and a cozy den area perfect for reading or quiet work. Step outside to enjoy the large slate patio framed by handsome stacked stone walls or unwind on the private Trex deck overlooking the .75-acre lot. A rare blend of charm and space just minutes from the historic village of Old Bennington.

Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized kitchen is perfection for entertaining and for spending time with family and friends. The living room invites a space for conversation, a cozy fire during the chilly Vermont evenings, or simply relaxing taking in the divine views at sunset. More casually, the family room offers exposed beams, vaulted ceilings and abundance of natural light. A formal dining room is strategic to the kitchen for holidays and family gatherings. The second floor boasts three bedrooms and two bathrooms, while the third bath is on the first level for convenience. And have I mentioned the renovated space above the garage? Wow! Breathe in the fresh air, take a walk up a country road and hunker down for the most genuine, spectacular sunsets. This is the type of special property that you will not want to miss.

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 space. The updated baths bring a fresh, modern feel, while the library with a wet bar sets the perfect scene for entertaining guests. Enjoy warm summer evenings on the screened porch overlooking the peaceful backyard—an ideal spot for gatherings or quiet relaxation. With its timeless architecture and thoughtful upgrades, this home offers the best of both worlds: classic Colonial character and modern-day comfort.

Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct access to Bennington Area Trail System (BATS). Construction will meet or exceed Vermont's energy efficiency standards. Proposed house is a Ranch with one floor living: 3 bedrooms, 2 bathrooms, open concept kitchen/dining/living room, laundry room, mudroom, attached 2-car garage, covered front porch and rear patio. Realtor & Builder design team will walk you through all the choices you get to make, from exterior siding to interior paint colors, flooring and light fixtures, cabinets to countertops, and more. Base price includes luxury vinyl plank throughout the main rooms, carpeted bedrooms, tiled bathrooms, quartz or granite counters, and Stainless Steel kitchen appliances. If you love the location but want to consider a different layout or house style, we can redesign, renegotiate and build it to your satisfaction. Sold as a package with land and construction by Jonathan G. Hoffman Builder, a local general contractor with 40 years of experience. Seller is a Vermont licensed real estate broker.

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 three additional income-producing units, it offers immediate revenue potential for investors or owner-occupants alike. Set in one of the most unique and convenient locations in our community, this property enjoys steady foot traffic by day yet remains quiet and peaceful at night. Whether you envision keeping it as a multi-unit income generator, creating a live/work space, or converting it back into a single-family home, the possibilities are endless. Don’t miss the chance to own this one-of-a-kind property with built-in income opportunities right at your fingertips. Call today before it’s gone!

Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, Vermont Set 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 enhanced by gleaming wood floors. A large formal living room and dining room provide excellent flow for entertaining. Practicality meets charm with a mudroom, dedicated laundry area, and a substantial walk-in pantry. The primary suite includes a private bath and a serene sunroom retreat-perfect for morning coffee or quiet reflection. Two additional bedrooms and a recently updated bathroom with a new walk-in shower complete the main level. The walk-out lower level is a true bonus-featuring new laminate wood flooring throughout, it offers incredible potential as an in-law suite, home office, or recreation space, with plenty of room to add a kitchenette. Enjoy the peaceful surroundings from your large private deck, ideal for outdoor dining, relaxing, or entertaining guests. A rare find in a prime location-don’t miss your opportunity to own this versatile and spacious home in beautiful Bennington.