$209,000 $185 per sq.ft. Village of North Bennington in Town of Bennington VT Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1127  |  Acres: 0.23
Tuesday Apr 14, 2026
Description: Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an excellent opportunity to add your own finishing touches and build equity in a highly desirable location. Enjoy true village living with walkable access to cafés, restaurants, and trails, plus close proximity to Lake Paran and the Park-McCullough House. School choice at the elementary level adds flexibility. Just minutes to downtown Bennington for additional shopping, dining, and amenities, with easy access to multiple ski destinations. Conveniently located approximately one hour to Albany International Airport and about three hours to NYC and Boston. A rare opportunity to own in one of North Bennington's most sought-after settings. See MLS Property & Listing Details & 30 images.

$250,000 $171 per sq.ft. Bennington VT Home »

Price Change! Reduced by $10,000 down 4% on August 5th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1458  |  Acres: 0.25
Tuesday Jul 21, 2026
Description: Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to downtown restaurants, theater, and parks, the location is exceptionally convenient while still feeling like a true residential neighborhood. Inside, generous rooms, abundant natural light, hardwood floors, wide moldings, and original architectural details give the home warmth and personality. The spacious living room offers flexibility for gathering, relaxing, or creating multiple seating areas, while the adjoining dining room provides an inviting setting for everyday meals and entertaining. The bright kitchen features abundant wood cabinetry, generous counter space, a farmhouse-style sink, gas range, and direct access to the rear deck. Upstairs are four bedrooms and a full bath, offering ample flexibility for household needs, guests, a home office, or creative space. The primary bedroom includes two closets, and each bedroom has a ceiling fan and overhead light. The full basement houses the laundry and utilities, provides useful storage, and includes an additional toilet. There's a hot air furnace, Rinnai water heater, 100-amp panel, and town water/sewer. Outside, the rear deck overlooks the lawn, established garden beds, and a partially fenced area. A detached one-car garage adds convenient parking, storage, or workshop potential. The home is comfortable and offers a strong foundation. Exterior painting and porch restoration will be up to the next owner, creating an opportunity to refresh the property, make it their own, and build equity over time. With its gracious proportions, original charm, outdoor space, and exceptional location, 301 Elm St is ready for its next chapter. See MLS Property & Listing Details & 39 images.

$259,000 $146 per sq.ft. Bennington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1768  |  Acres: 1
Thursday Jul 9, 2026
Description: Well maintained and thoughtfully updated, this 4-bedroom, 2-bath home offers the ease of single-level living on a beautiful level one-acre lot in Bennington's desirable west end. Enjoy stunning mountain views from the spacious back deck or sip your morning coffee on the covered front porch. Inside, you'll find an updated kitchen, refreshed bathrooms, a cozy fireplace, central air conditioning, a 2023 roof, an updated heating system, and a spacious primary suite featuring a jetted step-in tub and separate shower. Offering the perfect blend of comfort, convenience, and low-maintenance living, there's also room to add your own personal touches over time. Enjoy a peaceful setting just minutes from downtown Bennington for dining, shopping, cultural attractions, and everyday conveniences, with easy access to multiple ski destinations. Conveniently located approximately one hour from Albany International Airport and about three hours from both New York City and Boston. See MLS Property & Listing Details & 36 images.

$264,900 $231 per sq.ft. Bennington VT Home »

Price Change! Reduced by $24,100 down 9% on August 7th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1146  |  Acres: 0.13
Tuesday Jun 23, 2026
Description: The renovations are done, just move in! Nearly everything is NEW at 109 County Street, including the price! In addition, the seller is offering a $5K credit towards the buyer's closing costs. This extensively renovated 4BR/2BA home with a fully fenced yard gives you the opportunity to enjoy the benefits of a much newer home without the time, expense, and stress of renovating one yourself. Featuring 3 generous bedrooms and a bathroom w/tiled shower on the second level, and a first floor bedroom, bathroom, and laundry on the main level. New roof. New windows. New siding. New insulation. New Deck. New electrical. New plumbing. New walls. New flooring. New Appliances. New lighting. New doors and trim. Fresh paint. And that's just the beginning. The beautifully renovated kitchen features brand-new cabinetry, countertops, and stainless-steel appliances, while the updated bathrooms offer modern fixtures and finishes. This renovation goes far beyond a fresh coat of paint- the seller has invested in the major systems and countless details that make home ownership truly low maintenance. This is the kind of house where you can unpack your boxes, and start living. No renovation projects. No wondering what needs to be replaced next. No spending your weekends working on the house. And now there's even more value: the seller is offering $5K toward the buyer's closing costs with an acceptable offer. That's money you can keep in your pocket for moving expenses, furnishings, or simply enjoy the benefit of a lower cash requirement at closing. Whether you're a first-time buyer, downsizing, looking for an investment, or simply want a beautiful home without a renovation project, this property deserves a look. Located just minutes from downtown Bennington, shopping, restaurants, schools, and everyday conveniences, 109 County Street combines extensive updates with practical location and exceptional value. Why buy a home that needs work when you can buy one where the work is already DONE? See MLS Property & Listing Details & 37 images.

$357,500 $206 per sq.ft. Village of North Bennington in Town of Bennington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1735  |  Acres: 0.54
Wednesday Jun 25, 2025
Description: Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience, just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the home. Brand new first floor half bath and mudroom entrance recently added. The dining room features a sliding glass door that opens to a spacious back deck, perfect for outdoor dining and relaxing. A covered front porch adds classic New England charm and a welcoming touch. With a large attached garage offering plenty of storage and workspace, this home is as practical as it is inviting. Whether you're enjoying the peaceful surroundings or entertaining guests, this home provides comfort, style, and a true sense of place in a friendly, walkable neighborhood. Don't miss this North Bennington gem, schedule your showing today! See MLS Property & Listing Details & 45 images.

$395,000 $218 per sq.ft. Bennington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1816  |  Acres: 0.42
Monday Aug 24, 2026
Description: Charming 4-bedroom, 1.5 bathroom house on private lane in desirable North Bennington, steps from Bennington College and a short walk to the Village center's restaurants, library, and shops. The home's first floor features an updated eat-in kitchen with granite countertops, dining room, living room with fireplace, half bath, and study with built-in bookcases, as well as a sun room which leads to the covered back porch. Upstairs, there are 4 bedrooms and a full bath. An airy sunroom off the primary bedroom could function as an office or a yoga/exercise room. With beautiful hardwood floors and kitchen and bathroom tile installed in 2018, the house features wildlife and tree-filled views from nearly every window. There is a 1-car attached garage with automatic opener, off-street parking, and a large, picturesque front yard with fruit trees and beds for gardening if desired. Park McCullough's bucolic trails are just a half-mile away. A half-hour drive to Williamstown and Manchester, North Bennington is a quiet, historic area. North Bennington Village School and close to downhill and cross-country skiing, hiking, and snowmobile trails. A quintessential New England village. See MLS Property & Listing Details & 31 images.

$439,900 $176 per sq.ft. Bennington NH Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2500  |  Acres: 1
Wednesday Jul 29, 2026
Description: Bennington is a great small town rich in history where you will find the Contoocook River. Students attend the wonderful schools in the Contoocook School District. Full of timeless charm and character, this unspoiled Village Colonial offers warm, inviting spaces and the opportunity to make it your own. Inside, you'll find lovely, homey rooms accented by wood flooring and original details that reflect the home's classic New England heritage. The kitchen is typical for an antique colonial with plenty of storage, a tin ceiling, and a view of the side yard. With five bedrooms, there is plenty of space for a growing family, guests, or flexible use such as a home office or hobby room. Currently, there is a first-floor bedroom that could be turned back to its original parlor. There is a "mud-room" where you will find the laundry, a walk-up attic, plenty of sitting areas, and space to spread out. Adding to its appeal is a spacious 18x28 barn, perfect for hobbyists, storage, or workshop space. The property is connected to town water and sewer, adding everyday convenience to its historic appeal. A rare chance to bring new life to a charming village home with great bones, character, and potential. See MLS Property & Listing Details & 44 images.

$460,000 $139 per sq.ft. Bennington VT Home »

Price Change! Reduced by $35,000 down 8% on August 24th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3312  |  Acres: 56.44
Wednesday Jun 17, 2026
Description: If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the owners in the '80s. The 3300+ square feet of living area on the upper level and another 3300+ on the lower level ready to be finished. As you can see, the lower level has plenty of windows and will be very flexible space to use. The two-car garage is attached to the house. From there, into the mudroom. The kitchen is very generous...There's room for your breakfast table, a couple of easy chairs and a love seat, and the woodstove will make this a cozy country kitchen to be. This is a 'cooks dream'. The commercial range will make your friends jealous, as will the pantry and stained glass on the upper cabinets. Off the kitchen is a large sunroom which leads out to the deck. Large dining room perfect for entertaining and a very comfortable formal living room. There are two guest rooms that share a tile bath. The primary suite has its own tile bath and a room that could be a nursery or an office. The lower level is ready to finish into living space if you need it. A few spots will need a bit of TLC, but the end result will be fantastic. Several updates have been done. For the handyman or animal lover, there is a 23x46 foot barn with room for several vehicles or machinery. There are two garage doors, and it even has a pit for working under your vehicles. The open land is gorgeous. Stonewalls and woodland await. If you enjoy sunny locations, this is a perfect spot. There is enough land to enroll the property into Vermont's Current Use program. This may be the spot you have been waiting for! Available due to owner relocation. See MLS Property & Listing Details & 54 images.

$475,000 $53 per sq.ft. Bennington VT Home »

6 Beds | 6 Baths |   Total Sq. Ft. 9000  |  Acres: 0.28
Tuesday May 5, 2026
Description: 15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R & D, climate controlled storage, or if you are a service provider company (electrical, plumbing and heating, etc.) in need of more space for at grade storage of inventory, vehicles and offices with easy access it is ideal space to run a service business from. Significant renovations have been completed to the interior 2nd floor of the building. This space is roughly 6,000 sq ft and is a blank slate at present but has been prepped for a residential buildout including plumbing for bathrooms, fire alarm and full sprinkler system, electrical service and other new systems in place. Informal plans have configured 2 to 7 possible apartments in this space depending on size and cost vs. income analysis OR possibly a large in-town owners' residence with skiing, hiking and other year-round outdoor recreational opportunities in the Green Mountain National Forest and Lakes and Rivers within it just a short drive away. Final state and local permits required for finalized development plan. This space combined with the flex space and retail storefronts along main street would be an ideal mixed-use income property. If creating value and optimizing income with creative development of a fantastic building is intriguing, this is an unbelievable and very unique opportunity. At this price point it would be challenging to find another commercial/residential building of this size and condition with this much potential to be solid income property with tremendous equity gain in a very quick timeframe. See MLS Property & Listing Details & 20 images.

$539,900 $436 per sq.ft. Bennington VT Home »

Price Change! Reduced by $10,000 down 2% on July 19th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2376  |  Acres: 1.94
Tuesday Jun 30, 2026
Description: Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with hardwood floors, and a stunning primary suite featuring a custom walk-in closet and a spa-inspired bath with heated tile floors. Offering exceptional flexibility, two of the four bedrooms are currently configured as home offices, while the versatile floor plan easily adapts to a variety of lifestyles. The bonus room includes plumbing for a future kitchenette, creating excellent potential for an in-law suite or multi-generational living. Step outside to enjoy the expansive deck, impressive stone patio, terraced gardens, and peaceful outdoor spaces designed for relaxing or entertaining. The detached two-car garage offers additional storage along with a heated workshop complete with water and electricity, making it ideal for hobbies, projects, or extra workspace. Additional highlights include an updated heating system, updated septic system, pull-down attic access with generous storage, and a whole-house fan for added comfort. This exceptional property combines timeless character, thoughtful updates, and remarkable versatility in a peaceful country setting. See MLS Property & Listing Details & 37 images.

$550,000 $279 per sq.ft. Village of Bennington in Town of Bennington VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 1974  |  Acres: 17.62
Tuesday May 12, 2026
Description: Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home. Situated on over 17 acres, this property offers not one but two barns, established fenced pastures, and the kind of setting that feels like a Vermont dream. Listen to the breeze move through the grass, watch the leaves change color in the fall, and enjoy the privacy and beauty that surround you. Inside, you'll find five bedrooms and two full bathrooms, with space that invites family dinners, holiday gatherings, and everyday moments that make a house feel special. The usable basement offers excellent storage, workshop potential, tool space, or room for tack and farm equipment. Whether you have horses, farm animals, or simply want the charm and comfort of country living, this property offers the Vermont lifestyle so many people dream about. This is more than a house it's the feeling of finally coming home. See MLS Property & Listing Details & 41 images. Includes a Virtual Tour

$595,000 $108 per sq.ft. Village of North Bennington in Town of Bennington VT Home »

Price Change! Reduced by $55,000 down 9% on August 21st 2026
5 Beds | 3 Baths |   Total Sq. Ft. 5524  |  Acres: 9.89
Tuesday Jun 9, 2026
Description: Step into this beautifully built post-and-beam house by well-known local builders Blue Heron Construction. Built in 1989 in classic Blue Heron style with an earthy exterior and a warm, glowing, golden interior, the house retains its original features, just waiting to be embraced by its next occupant. The location of the home couldn't be better, nestled on 9+ secluded acres in North Bennington. Create your own walking trails or explore the lovely rural roads in the neighborhood. Practical and cultural amenities are just minutes away by foot, car, bike or snowshoes. Entering the home through the brick-floored mudroom, you arrive in a large, open living/kitchen area with high ceilings, exposed beams and a cozy wood stove. Surrounding this inviting space, you will find a master bedroom with bathroom annex, a dining room, an office/library, and a second ground floor bedroom. Up the bespoke wooden staircase are 3 more rooms with bathroom and separate entrance, perfect for extended family or multi-generational living. Back downstairs, you will be stunned by the size of the huge, heated workshop, with plenty of room for a woodworker, potter, jeweler, painter or sculptor to work their magic. Above this workspace is a large second-floor studio apartment with private entrance and a spacious screened porch. A substantial barn/garage with a loft area provides even more space for vehicles, equipment, storage, or future expansion. If you're looking for multi-generational living, short or long term rental opportunities, or room for home-based business, this house could be perfect for you. The property is accessible from College Road but also has approximately 100 feet of road frontage on Matteson Road which could present future building opportunities, subject to local approvals. This house is a spacious North Bennington jewel. Move in right away, or take your time with a retrofit, as this house offers the versatility and flexibility to be whatever you want it to be. See MLS Property & Listing Details & 32 images. Includes a Virtual Tour

$695,000 $626 per sq.ft. Bennington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1614  |  Acres: 14.7
Friday May 15, 2026
Description: Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the serenity and natural beauty for years to come. The thoughtfully designed open-concept main level features a bright and inviting living area, ideal for entertaining or relaxing while taking in the surrounding landscape. The primary bedroom and an additional guest bedroom are conveniently located on the main floor, along with a three quarter bath. A versatile loft area provides the perfect space for a home office, study area, or cozy kids' hangout. The finished lower level expands the living space with two additional guest bedrooms, full bath, mechanical room with laundry hookups and ample storage. A one-car garage adds convenience and functionality. Step outside to the expansive deck designed for exceptional three-season living, where you can unwind, entertain, and enjoy amazing views in complete privacy. Fully renovated and move-in ready, including a new roof installed in 2024 as well as new furnace, new skylights, new flooring on the lower level and more, this special property combines modern comfort with the peace and beauty of a protected natural setting. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$255,000 $91 per sq.ft. Benson VT Home »

7 Beds | 3 Baths |   Total Sq. Ft. 2800  |  Acres: 1
Tuesday Apr 28, 2026
Description: A rare opportunity to own a largely renovated, income-producing multi-family property that blends historic Vermont charm with modern efficiency. Listed for under appraised value! Originally built circa 1865, this classic farmhouse has been thoroughly updated, allowing for immediate ownership without additional capital investment. Improvements include new plumbing, HVAC, electrical, vinyl windows, flooring, appliances, and fresh interior paint. Offering approximately 2,800 square feet, the property includes seven bedrooms and three full bathrooms across two separate living units, creating flexible options for investors, owner-occupants seeking rental income, or multi-generational living. Current rental income is $2,450 per month, providing solid cash-flow potential and long-term value. The home sits on a level, landscaped one-acre lot, offering space for gardens, a garage, or future expansion. The property is within walking distance to the library, local restaurant, church, and school. Outdoor recreation is close at hand with Lake Champlain, nearby ATV and snowmobile trails, and Killington Ski Resort less than an hour away. Zoned residential/mixed-use, the property supports residential living alongside rental income or a home-based business. Separate entrances and utilities add privacy and flexibility. 2830 Stage Road delivers a rare combination of turnkey updates, historic character, and dependable income potential. See MLS Property & Listing Details & 56 images.

$629,000 $229 per sq.ft. Benson VT Home »

Waterfront on Pond
4 Beds | 2 Baths |   Total Sq. Ft. 2744  |  Acres: 17
Monday Apr 27, 2026
Description: Seventeen acres. Lake Champlain down the road. A setup that actually delivers on the Vermont lifestyle without the usual compromises. Set along North Lake Road in Benson, just moments from the Benson boat launch, this fully renovated farmhouse sits on a highly usable mix of open pasture and productive land. About five acres are mostly fenced for animals, with the balance level, hayed, and tillable. The home has been completely updated, offering classic farmhouse character without the project list. Inside features four bedrooms, two bathrooms, first-floor laundry, stone countertops, stainless steel appliances, and a large living area with a pellet stove and mini split. Upstairs, the primary suite includes a walk-in closet and private en suite. The basement is dry, and metal roofing adds long-term peace of mind. A covered back porch overlooks your land and pond, perfect for morning coffee or evening sunsets. Outbuildings set this property apart. Attached one-car garage with power, plus a massive metal garage with space for at least six vehicles and ceiling height for lifts. The barn includes power, water, horse stalls, tack room, and hay storage above, and once housed a well-known racehorse. A four-bay pole barn with power adds even more flexibility. The land itself offers more than just usability, it's also a great setting for anyone who enjoys the outdoors, with abundant deer, turkey, and other wildlife regularly passing through the property. Less than a mile to Lake Champlain and an easy drive to Killington. If you've been waiting for usable land, a move-in ready home, and serious infrastructure, this is it. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour