Bennington Real Estate

Nestled in the scenic Green Mountains of southwestern Vermont, Bennington is a charming town that beautifully blends rich history with vibrant community life. Known for its picturesque landscapes and welcoming atmosphere, Bennington offers a unique quality of life that attracts both residents and visitors alike.

With a population of just over 15,000, this quaint town is steeped in history, dating back to the Revolutionary War. Bennington is home to several historical landmarks, including the Bennington Battle Monument, which commemorates a pivotal battle in American history. Strolling through the charming downtown area, you'll find an array of boutique shops, delightful cafes, and art galleries that showcase the creativity of local artisans.

Nature enthusiasts will find Bennington to be a paradise, with countless opportunities for outdoor activities. The nearby Green Mountain National Forest offers hiking trails, fishing spots, and breathtaking views that change with the seasons. The fall foliage here is nothing short of spectacular, drawing visitors from all around to witness the vibrant colors.

Bennington also boasts a strong sense of community, with numerous events throughout the year, such as the Bennington Potters' Festival and summer farmers' markets. Local schools are well-regarded, making it an ideal place for families looking to settle down.

Whether you're drawn by its historical charm, natural beauty, or the warmth of its community, Bennington is a delightful place to call home. Experience the best of Vermont living in this enchanting town, where every corner tells a story and every day brings new adventures.

Newest Listings in Bennington

$154,000

2 Beds ⋅ 2 Baths ⋅ 5113833 MLS

Enjoy downtown living in Bennington with this 2BR/2BA ground-floor condominium. Convenient single-level living with in-unit laundry and dedicated parking for added comfort and practicality. Ideally located within walking distance of downtown shops, restaurants, the library, and public transportation, you’ll appreciate having everyday amenities close at hand. Whether you’re looking for a full-time residence, downsizing, or seeking a low-maintenance alternative to traditional homeownership, this condo offers a wonderful opportunity to enjoy the convenience of downtown living without the demands of exterior maintenance.

432 South St Unit C3, Bennington

$235,000

5113809 MLS

The Best of Both Worlds! A Home with Room to Grow and Income Potential! Looking for a property that offers more than just a place to call home? Welcome to 224-226 Branch Street, where comfortable living meets incredible versatility! This single-family home features a spacious backyard, a back deck perfect for relaxing or entertaining, and a storage shed for all your outdoor essentials. The expansive yard offers plenty of room for gardening, recreation, pets, or simply enjoying your own outdoor space. But what truly sets this property apart is the converted barn featuring an apartment that is currently rented! Imagine the possibilities of having a separate rental space to help offset your mortgage, accommodate extended family, or potentially create your own home office, studio, or workshop. Whether you’re looking for a primary residence with additional income potential, a multigenerational living arrangement, or simply a property with extra space to pursue your passions, this unique offering provides flexibility that’s hard to find. Live in the house, enjoy the yard, and let the possibilities of the barn work for you!

224-226 Branch St, Bennington

$389,000

4 Beds ⋅ 2 Baths ⋅ 5113804 MLS

Brand New Construction in Desirable Chester Knoll! Welcome home to this beautifully crafted, energy-efficient Cape offering the perfect blend of classic New England charm, modern comfort, and thoughtful design. Built with quality and efficiency in mind, this inviting home offers a wonderful floor plan designed for both everyday living and entertaining. Step inside to discover bright, welcoming living spaces and the convenience of a first-floor bedroom and full bathroom, providing flexibility for guests, a home office, or one-level living. Beautiful Deck off the dining and kitchen area. Upstairs, you’ll find three additional bedrooms and full bathroom, including a spacious primary room. Thoughtful layout and quality built, while energy-efficient construction helps provide year-round comfort and manageable utility costs. The full basement offers excellent storage and additional possibilities for future use with walk out. Located in the desirable Chester Knoll neighborhood, this beautiful BRAND new home offers the opportunity to enjoy the comfort, convenience, and peace of mind that come with new construction. Move right in and start making memories in a home that’s ready for its very first owners! Listing agent is the Seller.

319 Chester Knoll Dr, Bennington

$285,000

3 Beds ⋅ 2 Baths ⋅ 5113739 MLS

Welcome to this spacious three bedroom, two bathroom ranch in a highly desirable neighborhood, offering approximately 3,000 square feet of finished living space and plenty of room to grow. Conveniently located near local shopping and amenities, this home offers the space, location, and flexibility you’ve been looking for. Since purchasing the home, the owners have completed numerous improvements, including installing laminate flooring throughout the upstairs living areas, addressing foundation work, and making necessary plumbing improvements in the bathrooms. These updates, along with a newer boiler and a roof less than six years old, provide a solid foundation for the next owner. The home offers comfortable one-level living with a walkout lower level that provides tremendous flexibility for additional living space, a recreation area, home office, or potential in-law accommodations. With three bedrooms and two full baths, there is plenty of room for a growing family or extended family. Heating options are another great feature, with oil heat, a pellet stove, and a wood-burning fireplace offering three ways to keep the home comfortable. Outside, you’ll find an above-ground pool, a paved driveway, and a spacious two-car garage. If you’ve been looking for a large ranch in a desirable neighborhood with room for family, entertaining, hobbies, or even extended family living, this could be the one you’ve been waiting for. Schedule your showing today!

38 Center St, Bennington

$480,000

4 Beds ⋅ 3 Baths ⋅ 5113685 MLS

Love character, craftsmanship and room to gather? Welcome home. At first sight you will notice the artistry of the hand selected stone used to create the garage exterior design surrounding the oversized, insulated doors. The garage itself is oversized with insulated and sheetrock walls. As guests arrive they are welcomed by lush ivy gracefully framing the entryway, setting an inviting and charming tone The charm continues inside with Vermont maple flooring throughout the first floor with exposed beams that add to the ambiance. The newly updated kitchen features granite countertops. custom cabinetry, stainless steel appliances and a spacious center island. Expansive windows in the dining area frame the Vermont Mountain Views. A light-filled living room has vaulted ceilings and a cozy fireplace with an efficient insert. The alcove lit hallway leads to the first floor bedroom suite with a full bath that features a soaking tub and a lovely stain glassed window. A conveniently located laundry room and half bath add everyday convenience. A finely handcrafted staircase accented by wrought iron hand rails leads to the upper-level where rich Canadian cherry flooring continues throughout with 3 bedrooms including one with a private bath, another full bath and linen closet add to convenience. The finished lower level adds another layer of versatility with a generous bonus family room that provides valuable additional space, complemented by spray foam insulation for enhanced energy efficiency. The attic has enough height to comfortably stand and move around throughout the space with potential for a home office or additional storage.Step outside and discover your own private sanctuary with beautifully established grounds and two full sized decks. At the heart of it all your very own salt water spa provides the perfect place to unwind, relax and enjoy. All nestled in a sought-after neighborhood just moments from town makes this home a rare blend of character and convenience.

55 Mcintosh Ln, Bennington

$425,000

3 Beds ⋅ 2 Baths ⋅ 5113018 MLS

Beautifully renovated inside and out, this 3-bedroom, 2-bath Ranch offers 1,788 square feet of comfortable single-level living in a highly coveted Bennington location. Tucked into an established neighborhood on the outskirts of town, the property feels private and peaceful while remaining just minutes from major shopping, services, and everyday conveniences. Thoughtfully remodeled with a gorgeous new kitchen featuring KraftMaid cabinetry, stainless steel appliances, generous counter space, and a contrasting center island. New vinyl plank flooring, additional overhead lighting, and larger windows create a bright, fresh feel throughout. The spacious living room is anchored by a dramatic feature-wall fireplace with a new mantel and woodstove insert, creating a warm focal point for the home. In addition to three bedrooms and two full baths, the main level includes a dedicated office and separate laundry room, making the floor plan especially practical for today’s lifestyle. The primary bedroom is generously sized and includes a private bath and walk-in closet. Outside, mature trees and lush perennial gardens surround the home, while the rear patio and side deck offer quiet places to relax and enjoy the wooded setting. An attached two-car garage with a new automatic opener adds everyday convenience, and the full basement has been professionally improved by Northern Basement Systems to provide a clean, dry space with excellent storage potential. Other improvements include a newer Buderus boiler, a 200-amp electrical panel, heat pump mini splits for energy-efficient heating and cooling, and leased solar panels. A beautifully reimagined home, a highly functional one-level layout, and a location that offers both neighborhood living and quick access to town make 78 Astrachan Drive a true standout.

78 Astrachan Dr, Bennington

$145,000

2 Beds ⋅ 2 Baths ⋅ 5112929 MLS

Enjoy the convenience and value of this two bedroom, 1.5 bathroom end-unit condo. Offering easy first-floor living, this home is a great option for first-time buyers, downsizers, or anyone looking for a comfortable, manageable place to call home. The practical layout includes two bedrooms, providing flexibility for guests, a home office, or additional living space. Discover the simplicity of condo living and the ease of having everything on one level. Ideally located just minutes from downtown shops and restaurants, while still within walking distance of peaceful hiking and nature trails. Whether you're looking to simplify your lifestyle or find an affordable path to homeownership, this is an opportunity worth exploring.

432 South St Unit B3, Bennington

$479,000

3 Beds ⋅ 3 Baths ⋅ 5112804 MLS

New construction with views overlooking Powder Mill Pond! Currently under construction with estimated completion at the end of January 2027, this thoughtfully designed home is part of a duplex situated on its own lot. Offering 3 bedrooms, 2.5 baths, a first-floor primary suite, and an attached one car garage, the layout combines comfortable everyday living with energy efficient construction. A welcoming front portico leads into an open concept kitchen and dining area, flowing into a spacious living room with access to the rear patio. The first floor primary suite features a private bath and walk in closet, while a separate powder room with laundry adds convenience. Upstairs, two additional bedrooms, a study, and a full hallway bath provide flexible space for family, guests, or working from home. Quality construction includes a sound reducing, fire rated separation wall between residences. Energy efficient Hyper Heat systems provide heating and air conditioning for year round comfort. The direct entry garage and additional off street parking complete the practical design. Enjoy pond views and a Bennington setting with access to the shopping, dining, and cultural offerings of nearby Peterborough. An opportunity to own a new home with a versatile floor plan in the Monadnock Region. Photos show previously completed units with the same floor plan and similar finishes

00 Ross Rd, Bennington

$325,000

3 Beds ⋅ 2 Baths ⋅ 5112061 MLS

Have you bought your seasons pass to Crotched Mountain yet?! If you haven't you better! This sweet little property just around the corner from the ski area is going to make someone very happy. Live here or buy as an investment and enjoy steady income renting it out. This property has new flooring, and is freshly painted. It's a clean slate awaiting your finishing touches. Crotched Mountain Golf resort is a few miles down the road. Whole house generator will keep you up and running even in the worst storms! Cozy up next to the pellet stove and watch the snow fall after hitting the trails. Buyers and Buyers agents to do their own diligence. Property is approximately 250 ft onto a class 6 town road that is not town maintained. Be prepared to have a vehicle with decent ground clearance and 4 wheel drive in the winter months. Buyer will be responsible for road maintenance and winter plowing access. Sold as-is. Seller has not lived at the property so first hand information is limited.

208 Onset Rd, Bennington

$329,000

3 Beds ⋅ 2 Baths ⋅ 5111698 MLS

Charming Bennington home with classic character, hardwood floors, and a bright enclosed sun porch! This inviting property offers a comfortable blend of traditional charm and everyday functionality, with spacious living areas. The generous living room provides plenty of room for comfortable seating and entertaining, while the sun porch offers a wonderful additional space to enjoy the changing seasons, morning coffee, reading, or simply relaxing surrounded by natural light. The home offers a warm, practical layout with attractive wood flooring and ample windows throughout. Outside, the property sits above the street with stone retaining walls, creating a private and inviting setting. The attached garage provides convenient parking and storage, with additional driveway space. Located in Bennington, this home provides easy access to the area's shops, restaurants, services, schools, and outdoor recreation. Whether you're looking for a home with classic Vermont character, 110 Coulter St offers a great opportunity to make a property your own.

110 Coulter St, Bennington

$975,000

4 Beds ⋅ 3 Baths ⋅ 5111680 MLS

Stunning Monument Avenue home offering unparalleled craftsmanship, exceptional style, and beautiful mountain and meadow views. This remarkable ranch-inspired design is equally impressive inside and out, with thoughtfully designed spaces and exceptional millwork throughout. The cook’s kitchen features soapstone countertops, stainless steel appliances, and abundant natural light from large windows. An expansive dining room opens to a vaulted, beamed great room, creating an inviting space for entertaining. A light-filled sunroom with a gas fireplace provides a warm and inviting place to relax, while the gorgeous primary suite offers a peaceful retreat. Three additional bedrooms, a den/office, and ample storage provide plenty of space for family and guests. One of the home’s standout features is the large screened-in porch, complete with a wood-burning fireplace, offering an exceptional setting for outdoor dining, entertaining, or simply enjoying the spectacular surroundings. With stunning views, beautiful craftsmanship, and exceptional indoor and outdoor living spaces, this is truly a must-see Monument Avenue home.

2100 Monument Ave, Bennington

$400,000

3 Beds ⋅ 2 Baths ⋅ 5111662 MLS

Two homes, one property, and plenty of possibilities! Welcome to 479 US Route 202 in Bennington, offering a unique opportunity for investors, owner-occupants, or those looking for flexible multi-generational living. Situated on approximately .75 acres, the property features a 2-bedroom main home and a separate 1-bedroom cottage, each with its own 3/4 bathroom. The main home is currently vacant and ready for its next owner, with recent updates including fresh interior paint that gives the home a clean, refreshed feel. Inside you'll find two bedrooms, a 3/4 bath, eat-in kitchen, and comfortable living spaces. The separate 1-bedroom cottage is currently tenant occupied, providing an existing source of rental income. With two independent living spaces and separate electric meters, this property offers plenty of flexibility. Live in the main home while collecting rent from the cottage, create a multi-generational living arrangement, or take advantage of the property as an investment opportunity. Outside, enjoy approximately .75 acres along with a deck, enclosed porch, outbuilding, and covered parking. Conveniently located along Route 202 with easy access to Bennington, Antrim, and the surrounding Monadnock Region. Whether you're looking for a home that can help offset monthly expenses or an investment property with two separate living spaces, 479 US Route 202 offers a unique opportunity. Come to our Open Houses on 10/3 from 11am to 1pm and 10/4 from Noon to 2pm or schedule your private showing!

479 Us Highway 202, Bennington

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