Bennington, VT Homes for Sale under $400,000

Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

Max Squiers KW Vermont - Brenda Jones Real Estate Group

Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

Kelley Mccarthy Mahar McCarthy Real Estate

This beautifully renovated 2-unit home by JDN Properties offers exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize

Dan Mason Perrott Realty

Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".

Max Squiers KW Vermont - Brenda Jones Real Estate Group

Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again.Inside, you'll find generous living space ready for your vision and updates. A

Lindsey Martin Maple Leaf Real Estate

2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

Lori Hurley Four Corner Properties LLC

Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

Lindsey Martin Maple Leaf Real Estate

Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

Lindsey Martin Maple Leaf Real Estate

Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

Julie Glover Mahar McCarthy Real Estate

Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street.

Julie Glover Mahar McCarthy Real Estate

Build Your Dream Home—Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own.This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision.Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully

Lilli West Maple Leaf Real Estate

Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the

Lindsey Martin Maple Leaf Real Estate

Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

Melissa Nebelski Real Broker LLC

Tucked into a private wooded setting on the outskirts of town, this distinctive 3-bedroom, 1.5-bath Adirondack-inspired chalet blends rustic character, flexible living space, and an exceptional connection to the outdoors. Its steep roofline, front balcony, exposed beams, and metal roof give the home memorable architectural presence, while the peaceful surroundings create a true retreat from the

Jenifer Prouty Hoffman Hoffman Real Estate

Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

Welcome to your like-new home in the heart of Bennington! Within easy walking distance of the vibrant downtown district, this beautifully renovated 4-bedroom, 2-bath New Englander has been completely transformed into a truly turnkey property. Nearly every aspect of the home has been updated, allowing you to enjoy the benefits of modern, low-maintenance living from day one.Extensive

Angela Bevin Maple Leaf Real Estate

This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

Dan Mason Perrott Realty

Opportunity is knocking... answer the door! This home in a sought-after neighborhood on an almost half acre lot is the investment you've been looking for. Close to downtown shopping and dining, as well as the award-winning Southwestern Vermont Medical Center. Features include an attached two car garage, wood floors, mini-split in living room, fireplace, wood floors, dining room, primary bedroom

Justine Curry Maple Leaf Real Estate

MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances.The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large

Beatrice O'Connell Maple Leaf Real Estate

STOP RENTING and start building equity! Call your lender today to discover the latest programs that could MAKE HOMEOWNERSHIP A REALITY. Owning may be closer than you think. The transformation inside this home is nothing short of spectacular. This move-in-ready, one-floor living bungalow has been thoughtfully designed to maximize every square foot, including a brand-new bathroom and updated

Lori Hurley Four Corner Properties LLC

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 bedrooms.

Cassie Barbeau Mahar McCarthy Real Estate

Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

William Paquin Maple Leaf Real Estate

Set on over 5.5 acres of private, natural surroundings, this unique split-level ranch with an auxiliary dwelling unit offers an exceptional opportunity for multi-generational living, rental income, or a private guest retreat. Surrounded by peaceful woodlands, the property provides a tranquil rural setting while remaining just a short drive from town amenities.The main residence features three

Lindsey Martin Maple Leaf Real Estate

Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a

Jenifer Prouty Hoffman Hoffman 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

Welcome to this 3 bedroom, 1.5-bath Cape style home located in a planned commercial zone. Offering 1,688 square feet of well-designed living space on a manageable 0.26-acre lot, this inviting residence is perfect for comfortable family living. Offers beautiful hardwood floors gracing the upstairs bedrooms, as well as the spacious living and dining rooms—ideal for gathering with loved ones. The

Timothy Corcoran Mahar McCarthy Real Estate

Convenient one-level living meets modern style and design in this beautifully crafted ranch home, situated on a spacious 1.4-acre lot within a newer, private four-home subdivision. Relax on the impressive 52-foot farmer’s porch—perfect for enjoying cool summer breezes, stunning sunsets, entertaining guests, or simply taking in the expansive yard and thoughtfully designed plantings. Inside the

Matt Waddington Hoffman Real Estate

Townhouse style condo on the north side of Nathaniel court. Living room, kitchen, and half bath downstairs. Upstairs is the full bath with laundry and 2 bedrooms. No pets allowed.

Max Squiers KW Vermont - Brenda Jones Real Estate Group

This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family. use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 2-bedroom and 3-bedroom units, this property is designed to adapt to

Dan Mason Perrott Realty

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 Real Estate