Bennington Real Estate

Welcome to Bennington, Vermont, a charming town nestled in the picturesque Green Mountains. Known for its rich history and vibrant arts scene, Bennington is a place where small-town charm meets stunning natural beauty. With a population of just over 15,000, this tight-knit community offers a welcoming atmosphere that makes newcomers feel right at home.

Bennington is steeped in history, with roots dating back to the late 18th century. The town is home to several historical landmarks, including the Bennington Battle Monument, which commemorates a pivotal battle in the American Revolutionary War. Strolling through the quaint downtown area, you’ll discover unique shops, delightful cafes, and art galleries that showcase the talents of local artisans.

Nature enthusiasts will find plenty to love about Bennington. The surrounding mountains provide ample opportunities for outdoor activities, from hiking and biking to skiing and snowboarding in the winter months. The nearby Green Mountain National Forest offers breathtaking views and trails for all skill levels, ensuring that adventure is always just around the corner.

Bennington also boasts a vibrant cultural scene, with events and festivals happening year-round. The Bennington Museum showcases the region's art and history, while the local theater company offers performances that entertain and inspire.

Whether you’re looking to settle down in a cozy home, explore the great outdoors, or immerse yourself in a rich cultural tapestry, Bennington is the perfect place to call home. Discover the magic of this enchanting town and see why so many are drawn to its beauty and charm.

Newest Listings in Bennington

$299,900

3 Beds ⋅ 2 Baths ⋅ 5116525 MLS

Great ranch style home on 0.83 acre in the Clark's woods neighborhood, just down the hill from the golf course and backing up to the river. Offering 3 bedrooms, 1 and a half bathrooms, large living room, kitchen and dining room. Main level laundry, large basement, and garage. Attached storage and out building. Hurry to see.

13 Hunt St, Bennington

$349,000

3 Beds ⋅ 2 Baths ⋅ 5116415 MLS

Located in the desirable Chester Knoll development, this beautifully maintained 3-bedroom, 2-bath home offers three levels of light-filled living space, thoughtful updates, and exceptional versatility. From the moment you step inside, you'll appreciate the generous floor plan, abundant natural light, and inviting atmosphere that makes this home feel both spacious and cozy. Cork flooring adds warmth and character to the main level, while comfortable carpeting creates a welcoming retreat in the bedrooms. A charming deck off the dining room and a welcoming front balcony provide inviting spaces to enjoy the outdoors. French doors offer an additional connection to the outside, adding to the home's light and airy feel. Energy-efficient mini-splits provide both heating and cooling, offering year-round comfort without the worry of fluctuating oil prices. One of the home's most unique features is the thoughtfully redesigned primary bedroom, complete with a modern kitchenette that creates a suite-like experience. Ideal for extended family, guests, or simply enjoying the luxury of your own private retreat! The finished lower level features a freshly carpeted recreation room, providing flexible space for entertaining, hobbies, a home office, or relaxing. A one-car garage adds everyday convenience. Adding to the appeal is a remarkably affordable HOA that covers trash removal, lawn care, and road maintenance, allowing you to spend less time on upkeep and more time enjoying your home. Exceptionally cared for and move-in ready, this home offers a wonderful combination of comfort, efficiency, and flexibility in a sought-after neighborhood. An easy walk to downtown, yet close to walking and biking trails too. You really can have it all!

309 Chester Knoll Dr, Bennington

$215,000

3 Beds ⋅ 2 Baths ⋅ 5115662 MLS

Good sized home situated on the corner of Weeks Street and Putnam Street. Walking distance to the hospital, corner market and post office. # bedrooms including a large bedroom on the second floor and a main level bedroom as well. Large living room, kitchen and 1 and a half baths. Vinyl sided, large front porch with a 3 season porch as well. Paved driveway and great location.

200 Weeks St, Bennington

$699,000

5115602 MLS

Historic Downtown Bennington Commercial Property – Endless Possibilities! Discover a rare opportunity to own a piece of Bennington’s history! Built in 1840 and listed on the historic registry, this distinctive three-story property offers exceptional potential in a premier Main Street location, just steps from the Four Corners intersection of Main Street and Route 7. Currently operating as a law office, the property offers flexibility for a variety of commercial uses, including professional offices, medical or wellness practices, entrepreneurial ventures, or an investment property. The second and third floors present exciting possibilities for residential conversion, with potential for two separate apartments or a spacious two-story townhouse, subject to applicable zoning, permitting, and historic preservation requirements. Enjoy outstanding visibility, steady traffic exposure, and convenient walkability in the heart of downtown Bennington. Whether you're an investor, business owner, or visionary looking to create something special, this historic property offers a unique opportunity to bring your ideas to life in a location that’s hard to beat!

409 Main St, Bennington

$345,000

3 Beds ⋅ 2 Baths ⋅ 5115368 MLS

Superb location, inviting living spaces, and a private backyard make this raised ranch a wonderful place to call home! Offering three bedrooms, two full bathrooms, and a versatile office complete with a Murphy bed, this home provides flexibility for guests, working from home, or additional living space. The open concept kitchen, dining room, and living room create a bright, welcoming atmosphere that's perfect for everyday living and entertaining. New flooring throughout most of the home adds a fresh, updated feel. Step outside onto the spacious deck, ideal for grilling, outdoor dining, or simply relaxing while overlooking the private backyard. With a functional layout, flexible living spaces, and a fantastic location, this home has so much to offer!

882 Matteson Rd, Bennington

$499,000

3 Beds ⋅ 3 Baths ⋅ 5114993 MLS

New construction with views overlooking Powder Mill Pond! Currently under construction with estimated completion February 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 Knightland Cir, Bennington

$479,000

3 Beds ⋅ 3 Baths ⋅ 5114986 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

$299,000

3 Beds ⋅ 2 Baths ⋅ 5114802 MLS

Move-In Ready 3-Bedroom Raised Ranch with ensuite primary. Fresh paint and new flooring make this three-bedroom, two-bath Raised Ranch, located just outside of town, ready for you to move right in. Keep the fresh finishes or change the paint colors to make the home your own. The eat-in kitchen opens to the living room, creating a spacious, inviting layout that is ideal for entertaining. Sliding glass doors lead to a tiered deck with space ready for an above-ground pool. The lower level offers an office or den, an exercise room, and a workshop currently set up as a hairstyling area. A paved driveway leads to the one-car basement garage. All of this is situated on a 0.44-acre lot.

48 Autumn Acres Rd, Bennington

$835,000

5113984 MLS

Exceptional investment opportunity in downtown Bennington! This income-producing multi-family property features eight apartments across two buildings, offering a versatile mix of four 2-bedroom/1-bath units and four 3-bedroom/1-bath units. With eight rental units and an additional unimproved 0.26-acre lot, this property offers investors an opportunity to build long-term wealth while exploring future value-enhancement possibilities. Three apartments have undergone updates/renovation within the past two years, providing a solid foundation for continued investment and potential rental growth. Ideally situated just off Main Street, the property benefits from convenient access to downtown Bennington's shops, restaurants, services, and amenities. A rare opportunity to acquire a substantial multi-unit investment with room to maximize its potential in a desirable downtown location.

127-133 Webb St, 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

$219,000

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

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Bennington Real Estate

Newest Listings in Bennington

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