Newest Homes for Sale in Bennington, VT

Stop paying rent and start building equity! 340 Pleasant Street is a charming two-unit duplex located in the heart of Bennington, offering the perfect opportunity for an owner-occupant to live for less. The vacant lower unit is move-in ready, while the upstairs unit is occupied by a reliable, long-term tenant whose rent can significantly offset your mortgage payments. To make this deal even

Lori Hurley Four Corner Properties LLC

Rare opportunity to own a high-performing multi-family portfolio on a spacious .75-acre lot in Bennington. This property features 9 total units spread across two well-maintained buildings. The primary 6-unit building has seen significant recent capital improvements, including a brand-new metal roof and five fully renovated apartments featuring modern finishes. The sixth unit remains occupied by a

Lori Hurley Four Corner Properties LLC

Welcome to this charming Cape-style home, nestled in a peaceful country setting just moments from Bennington College and scenic walking and hiking trails. This inviting property offers the perfect blend of rural tranquility and convenient access to town. Located just 10 minutes from downtown Bennington, you’ll have quick access to local shops, restaurants, cultural attractions, and everyday

Thomas Martins Maple Leaf Realty

An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

Marek Kovac TPW Real Estate

A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly

Jenifer Prouty Hoffman Hoffman Real Estate

Tastefully renovated antique home that retained it character 4 bed 2 bath home with gleaming hardwood floor in through out with Vinyl plank in the bathrooms and Laundry room. The downstairs Ensuite is currently being used as an in home office with private entrance. This would make a great room for a in-law space with private bath and the 3 season sunroom could easily be converted into a

Dan Mason Perrott Realty

Built in 2000 this charming home is located in Catamount Mobile Home Park, a community with no age restrictions in beautiful Bennington, Vermont. Situated on a large corner lot with front and back decks offering mountain views. Open, light-filled floor plan with bright kitchen, living room, primary suite, second bedroom, full bath, and laundry. Features include a newer shed (1 year old) and

Colleen Zajac Monarch Realty

Classic cape with a twist! The eat-in kitchen has plenty of cooking area plus an eat-in area in a windowed alcove. The dining room is large enough for sit downs and the living room is the whole length of the house so movie nights are a go! In the entry side of the house you have a wonderful enclosed porch to serve as a mud room and a sweet sitting porch out front. AND!!!!... there is a fenced in

Christine Lewis Brattleboro Area Realty

Location, location, location! Own your own private oasis on a dead-end road with nearly 7 acres - only minutes from downtown shopping and dining. Enjoy seasonal mountain views from the deck with sliding doors to the open concept living/dining room with vaulted ceiling. The propane fireplace with gorgeous wood mantle keeps things toasty while providing cozy ambiance. The spacious kitchen has

Justine Curry Maple Leaf Realty

Charming downtown family home with modern upgrades.This beautifully updated 3-bedroom home is perfectly situated on a desirable corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, with a recent addition of a first-floor primary bedroom and new mudroom back entrance.Step inside to find gleaming hardwood floors and a warm, inviting layout. The dining

Lindsey Martin Maple Leaf Realty

Discover this beautifully updated home set directly on the Walloomsac River, offering 123 feet of peaceful river frontage. Enjoy fishing right from your own backyard, hosting gatherings by the water, or simply relaxing to the soothing sounds of the flowing river. Ideally located within walking distance of Main Street, the Rec Center (featuring a gym, sauna, indoor pool, and tennis and basketball

Matt Waddington Hoffman Real Estate

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

Monique Geannelis Mahar McCarthy Real Estate

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

Kelley Mccarthy Mahar McCarthy Real Estate

Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400).

Michael Gilman 3GEN Real Estate Inc

Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

Vicki Wilson Maple Leaf Realty

This inviting in-town home has been nearly completely renovated with only a few more touches to be brought by the new owner, blending fresh updates with classic comfort. Inside, you’ll find 3 bedrooms and a full bath, plus a bonus room that could serve as a 4th bedroom with a half-bath. An additional room with its own separate entrance is ideal for a small home business. The convenient attached

Cassie Barbeau Mahar McCarthy Real Estate

Beautifully Renovated 4-Bedroom Home with Modern Upgrades! Welcome to this stunning, move-in ready home that has been fully renovated with care and style. Offering 4 spacious bedrooms, 2 brand-new bathrooms, and 1,728 square feet of thoughtfully designed living space, this home is the perfect blend of comfort and modern living.Step inside to find gleaming hardwood floors that flow throughout

Timothy Corcoran Mahar McCarthy Real Estate

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

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 the

Jenifer Prouty Hoffman Hoffman Real Estate

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

Jenifer Prouty Hoffman Hoffman Real Estate

Huge Price Reduction. 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

Matt Waddington Hoffman Real Estate

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

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

Welcome to 41 Audrey Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

Welcome to 32 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

Welcome to 10 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

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