$295,000 $122 per sq.ft. Village of Bennington in Town of Bennington VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2418  |  Acres: 0.25
Tuesday Jun 17, 2025
Description: This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level features a newly renovated kitchen and bathroom, adding modern comfort to this historic property. With five bedrooms throughout, there's more than enough space to accommodate guests or create your ideal home layout. Keep it as a turnkey short-term rental, or easily convert it into a large single family residence with plenty of room to spread out. The property sits on a lovely lot with a private yard, perfect for outdoor entertaining, plus a one car garage that could be brought back to full use with some TLC. Located near Bennington's local events, shops, and attractions, this home is a smart opportunity whether you're investing, relocating, or dreaming of a versatile live/work space. Opportunities like this don't come along often. Call today to schedule a private showing and explore the potential. See MLS Property & Listing Details & 41 images.

$325,000 $109 per sq.ft. Bennington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2994  |  Acres: 4.12
Thursday Sep 18, 2025
Description: Set well back from the road, this mid-century modern home emphasizes simple lines, an indoor-outdoor connection, and panoramic views. The main level centers on an open living/dining/kitchen area anchored by a fireplace and oversized windows that overlook the pond and rolling landscape beyond. The primary suite on this level provides private comfort. A second-floor bedroom offers a rare upper-level retreat complete with a private bath - perfect for guests, teenagers, or a dedicated workspace. Though the home's layout and setting are outstanding, it needs thoughtful updating: kitchens and baths could be refreshed, finishes modernized, and mechanicals upgraded to improve energy efficiency. With cosmetic work and systems improvements, this property will be transformed into a stylish, comfortable showpiece that honors its mid-century heritage. This property delivers the best of both worlds - architectural interest and a peaceful natural setting. The pond and views create an immediate sense of escape, while the four-bedroom layout and three baths make it practical for full-time living or a vacation retreat. For buyers who appreciate mid-century lines and want to add modern amenities, this is an inspired canvas. See MLS Property & Listing Details & 48 images.

$339,000 $196 per sq.ft. Bennington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1728  |  Acres: 0.13
Tuesday Sep 23, 2025
Description: 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 the home. The completely updated kitchen is a true showstopper-featuring sleek cabinetry, new appliances, and contemporary finishes that make it ideal for both everyday living and entertaining. Both bathrooms have been fully remodeled with high-end fixtures and stylish finishes, creating serene, spa-like spaces. Additional upgrades include: New high-efficiency heating system, Heat pump water heater, New insulation, New exterior vinyl siding and all-new electrical wiring and panel. Situated on a manageable 0.13-acre lot, the property also includes a detached one-car garage for added convenience and storage. See MLS Property & Listing Details & 31 images.

$350,000 $208 per sq.ft. Village of North Bennington in Town of Bennington VT Home »

Price Change! Reduced by $15,000 down 4% on August 19th 2025
4 Beds | 1 Baths |   Total Sq. Ft. 1680  |  Acres: 0.54
Wednesday Jun 25, 2025
Description: Charming North Bennington Home in a Desirable Neighborhood. 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. 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.

$374,900 $110 per sq.ft. Village of North Bennington in Town of Bennington VT Home »

Price Change! Reduced by $24,000 down 6% on August 26th 2025
5 Beds | 4 Baths |   Total Sq. Ft. 3400  |  Acres: 2.6
Friday May 23, 2025
Description: Charming Historic Home with Garden, Barn & Flexible Living Spaces This beautiful 100+ year-old home offers over 3,400 sq. ft. of warmth, character, and room to grow. Flooded with natural light, this home on 2+ acres has three sunny upstairs bedrooms and three baths. In addition to a large living room and full dining room, the main floor has a laundry/mudroom and front and rear parlors that can serve as additional bedrooms, guest rooms, or cozy living spaces. The second floor features its own 2-bedroom, 1-bath apartment--perfect for multi-generational living, hosting guests, or generating extra income. Mature trees, wrap-around porches, a sunny lawn, and an ample garden offer space for planting, play, and relaxation, while a sturdy two-story barn provides endless possibilities--storage, workshop, studio, or hobby space. There is also separately entranced area at the back of the house that can provide office space. The house has many original details, including pocket doors, hardware, and woodwork, as well as double-pane windows throughout. This exceptional property, located in the North Bennington school district, offers a rare combination of history, space, and flexibility. Come and experience the warmth and potential of this one-of-a-kind home. See MLS Property & Listing Details & 50 images.

$425,000 $140 per sq.ft. Bennington VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3040  |  Acres: 0.58
Friday Aug 22, 2025
Description: Beautiful Colonial-style home with an oversized two-car attached garage, set in one of Bennington's most desirable neighborhoods. This inviting home features an open kitchen and family room, a bright sunroom, formal living and dining rooms, and 2.5 baths. The primary suite is complemented by three additional bedrooms, offering plenty of space for family and guests. A versatile, walkout finished basement adds even more options for work, play, or hobbies. Outside, you'll find a partially fenced yard perfect for pets or gardening, attractive landscaping, and lovely mountain views. Situated on a .58-acre lot, this is the only home currently available on sought-after Fox Hill-an opportunity not to be missed! See MLS Property & Listing Details & 49 images. Includes a Virtual Tour

$475,000 $226 per sq.ft. Bennington VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2104  |  Acres: 0.29
Saturday Sep 13, 2025
Description: Step into timeless elegance with this beautifully restored Victorian home, showcasing stunning woodwork and thoughtful updates throughout. This spacious residence offers five bedrooms, one being on the first floor, and two updated bathrooms blending classic character with modern comfort. A whimsical hidden quarter bath under the stairs adds both charm and function. The home's gracious layout highlights detailed millwork, soaring ceilings, and large updated and energy efficient windows that flood each room with natural light. A welcoming front porch and stately exterior details reflect the home's historic charm. It has been meticulously restored and maintained from top to bottom in recent years. The carriage barn, with its new, custom doors, provides endless possibilities--perfect for storage, a workshop, or conversion into a creative studio space. With its blend of period craftsmanship and modern updates, this property offers a rare opportunity to own a piece of history while enjoying all the conveniences of today. Just steps from downtown and the hospital and less than an hour to the Albany airport, this is the one you've been waiting for. See MLS Property & Listing Details & 35 images.

$499,000 $33 per sq.ft. Bennington VT Home »

Price Change! Reduced by $76,000 down 15% on August 13th 2025
6 Beds | 4 Baths |   Total Sq. Ft. 15179  |  Acres: 0.28
Wednesday Apr 2, 2025
Description: Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor direct entry parking for the resident(s) with ingress and egress stairs from Main Street in the front or from Union Street and the indoor parking in the rear. The space has been prepped with plumbing and electrical for kitchens and baths and also for HVAC to be installed. There are new framed walls with sheetrock and base coat of paint. This is not a blank slate! The hard work has been done and awaits your vision. The space even has south facing roof top decks possible and a sliding glass door already installed to this outdoor area. An awesome opportunity for those who want to be in the heart of a vibrant Vermont town with endless year-round recreation a short drive away in all directions. The area offers some of the best skiing, snowmobiling, hiking, biking, fishing, boating and much more and the Green Mountain National Forest is a short distance away. A fantastic alternative to an expensive single family due to income from two core commercial tenants on the main level. Very unique situation at an affordable price point. Residential use is permitted but may require permits. See MLS Property & Listing Details & 12 images.

$499,900 $236 per sq.ft. Bennington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2116  |  Acres: 2.93
Monday Jun 9, 2025
Description: Nestled in one of Bennington's most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm--all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System (BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious living room featuring a wood-burning fireplace and French doors that open to a private deck overlooking the park-like backyard. A separate study offers space for work or reading, while a dedicated laundry room, half bath, and entry to the attached two-car garage add convenience. Upstairs, you'll find four generously sized bedrooms, including a serene primary suite with a walk-in closet, an additional shoe closet, and a private en suite bath. A full hall bath serves the remaining bedrooms. The fully insulated basement provides excellent storage and features a new electric hot water tank with temperature controls. Outside, mature trees, lilacs, hydrangeas, berry bushes, herbs, and chestnut trees create a lush, beautifully landscaped setting. Move-in ready and meticulously maintained, this turn-key home offers classic comfort in a truly idyllic location. -- See MLS Property & Listing Details & 41 images.

$550,000 $195 per sq.ft. Bennington NH Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2814  |  Acres: 3.03
Saturday Mar 15, 2025
Description: Seller is motivated!The perfect four-season retreat with great views to Crotched Mountain! Ideally situated just across the road from the slopes, offering effortless ski access in the winter. When the snow melts, enjoy the nearby Crotched Mountain Golf Club just down the road for a relaxing day on the course followed by a bite to eat at their tavern restaurantThis 3 bedroom, 3.5 bath home offers great space with a back deck off the family room and an enclosed porch and deck off the primary suite. Whether you're carving through fresh powder, hiking scenic trails, or playing a round of golf, this location offers the ultimate balance of adventure and a great place to unwind. Includes a lot across the road with pond frontage. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour

$599,900 $160 per sq.ft. Bennington VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3742  |  Acres: 2.4
Monday May 19, 2025
Description: Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood - Bennington, Vermont Set on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all enhanced by gleaming wood floors. A large formal living room and dining room provide excellent flow for entertaining. Practicality meets charm with a mudroom, dedicated laundry area, and a substantial walk-in pantry. The primary suite includes a private bath and a serene sunroom retreat-perfect for morning coffee or quiet reflection. Two additional bedrooms and a recently updated bathroom with a new walk-in shower complete the main level. The walk-out lower level is a true bonus-featuring new laminate wood flooring throughout, it offers incredible potential as an in-law suite, home office, or recreation space, with plenty of room to add a kitchenette. Enjoy the peaceful surroundings from your large private deck, ideal for outdoor dining, relaxing, or entertaining guests. A rare find in a prime location-don't miss your opportunity to own this versatile and spacious home in beautiful Bennington. See MLS Property & Listing Details & 48 images.

$795,000 $324 per sq.ft. Bennington VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2450  |  Acres: 2.72
Friday May 23, 2025
Description: Welcome to this stunning 1850s home, perfectly sited on 2.72 acres with breathtaking mountain views. With 5 bedrooms, 2 full baths, and over three decades of loving ownership, this property offers the perfect blend of historic charm and modern updates in a peaceful, scenic setting. Inside, you'll find spacious, light-filled rooms enhanced by large windows and a calming palette of neutral colors throughout. The main level boasts beautiful hardwood floors, a formal living room, and an elegant dining room -ideal for entertaining or family gatherings. The updated kitchen is both functional and stylish, complemented by a large island. The cozy family room features a gas fireplace and a stunning bay window that frames the natural beauty outside, making it a perfect space to relax year-round. Step out onto the architect-designed covered porch and take in the mountain views-it's a tranquil retreat like no other. Outbuildings include a former four-stall horse barn, now used as excellent storage, and a second barn that has been transformed into a four-car garage with additional storage above -perfect for hobbies, vehicles, or workshop space. This rare property offers historic charm, modern comfort, and unbeatable views-an exceptional opportunity for those seeking space, serenity, and timeless New England character. See MLS Property & Listing Details & 42 images. Includes a Virtual Tour

$1,950,000 $280 per sq.ft. Bennington VT Home »

9 Beds | 7 Baths |   Total Sq. Ft. 6956  |  Acres: 94.56
Wednesday May 21, 2025
Description: Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining pantry, formal dining and living rooms. The private estate includes a three car garage, 3 bedroom caretakers cottage, artist studio and gunite heated in-ground pool. Set on the outskirts of the historic town of Bennington offering shopping, live theatre, restaurants, horseback riding and proximity to mountain and cross-country skiing. This is a rare opportunity to own an exquisite estate property with a myriad of possibilities as a family compound or country retreat. Only 45 minutes to Albany International Airport and approximately three hours to Manhattan and Boston. All measurements approximate. See MLS Property & Listing Details & 42 images.

$249,000 $89 per sq.ft. Benton NH Home »

Price Change! Reduced by $20,000 down 8% on September 25th 2025
4 Beds | 2 Baths |   Total Sq. Ft. 2800  |  Acres: 29.84
Monday Sep 15, 2025
Description: Benton, NH Antique White Mountain Retreat. Featuring 29.84 acres with stunning Mountain views and 2100+'on the Whitcher Brook this property awaits its next owner.The Antique homestead includes an18th century 2800+-sf, four bedroom home and detached 36 X 48 Barn. There some tilting here over the past couple hundred years and significant structural renovations will be required. The land is sloping and features a series of plateaus with mostly steep access to Whitcher Brook with some wonderful mountain views including Kinsman Notch. See MLS Property & Listing Details & 30 images.

$1,795,000 $452 per sq.ft. Benton NH Home »

Price Change! Reduced by $100,000 down 6% on September 20th 2025
5 Beds | 5 Baths |   Total Sq. Ft. 3973  |  Acres: 6.41
Wednesday Aug 20, 2025
Description: Discover the perfect retreat in this spectacular 5-bedroom, 5-bath timber frame home nestled in the heart of the North Country. From the moment you enter, you will be captivated by the careful attention to detail and design throughout. The luxurious, spacious kitchen opens seamlessly into a large dining area and an inviting Great Room, complete with a grand stone fireplace. From here, step onto the expansive front deck and take in the panoramic mountain views stretching from the Kinsman Range to Burke Mountain, Whiteface, and beyond. The first-floor primary suite offers a private escape with direct access to a screened porch, while the second level features three bedrooms and two guest baths. On the lower level, a dedicated entertaining space makes hosting family and friends effortless. Set on over 6 private acres, this property is a haven for outdoor living. Enjoy multiple seating areas, a cozy fire pit, and wooded walking trails created by the owners. The property abuts the White Mountain National Forest, placing endless hiking, wildlife, and natural beauty at your doorstep. Tranquil Long Pond and countless trailheads are just minutes away, while Lincoln and Cannon Mountain are only a short 20-minute drive. Whether it is skiing, hiking, or simply soaking in the peace and serenity, this home offers year-round enjoyment. Do not miss the opportunity to make this stunning property your sanctuary in the White Mountains! (Please note, town has property as 4-bdrm, septic is for 5) See MLS Property & Listing Details & 57 images. Includes a Virtual Tour