You are viewing all listings Homes with 4 or more Bedrooms between $0 and $30000000 dollars.
$210,000 $95 per sq.ft. Bennington VT Home »
5 Beds | 2 Baths | Total Sq. Ft. 2200 | Acres: 5.54Listed on Friday Jul 3, 2026
Description: 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 bedrooms and one bathroom, with a comfortable, inviting layout that flows seamlessly from the kitchen to the dining area and into the living room, creating an ideal space for everyday living and entertaining. A rear deck overlooks the serene landscape, offering the perfect place to relax and enjoy the beauty of the outdoors. The detached guest house includes two bedrooms, one bathroom, and a kitchen space, presenting endless possibilities for extended family, visitors, or supplemental income. While the guest house would benefit from updates, it offers tremendous potential to create a charming secondary living space. With expansive acreage, privacy, and versatility, this property is a rare opportunity to bring your vision to life and enjoy the best of country living with convenient access to town. See Listing Details & 59 images.
$259,000 $146 per sq.ft. Bennington VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1768 | Acres: 1Listed on 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 Listing Details & 36 images.
$260,000 $178 per sq.ft. Bennington VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1458 | Acres: 0.25Listed on 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 Listing Details & 39 images.
$269,900 $236 per sq.ft. Bennington VT Home »
Price Change! Reduced by $19,100 down 7% on July 7th 2026
4 Beds | 2 Baths | Total Sq. Ft. 1146 | Acres: 0.13
Listed on Tuesday Jun 23, 2026
Description: 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 improvements include a brand new roof, all new windows, energy-efficient insulation, new flooring throughout, new appliances, and countless modern finishes designed for comfort, style, and peace of mind. The bright and inviting main level showcases an eat-in kitchen with stylish finishes and direct access to a spacious deck and fully fenced yard, perfect for summer dining, entertaining, or simply relaxing outdoors. A first floor bedroom, full bathroom, and laundry area offer the convenience and flexibility of single-level living. Upstairs, you'll find three additional bedrooms and a generously sized bathroom featuring a beautifully tiled shower, providing plenty of space for family, guests, or a home office. With all the major updates already completed and every detail thoughtfully refreshed, this is truly low-maintenance living. Just a short stroll to downtown shops, restaurants, cafes, and community events, this is a rare opportunity to enjoy a completely renovated home in one of Bennington's most convenient locations. Just unpack and enjoy! See Listing Details & 37 images.
Under Contract
$357,500 $206 per sq.ft. Village of North Bennington in Town of Bennington VT Home »
Price Change! Reduced by $7,500 down 2% on June 25th 2026
4 Beds | 2 Baths | Total Sq. Ft. 1735 | Acres: 0.54
Listed on 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 Listing Details & 45 images.
$389,000 $240 per sq.ft. Bennington VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2516 | Acres: 0Listed on Thursday Jun 11, 2026
Description: 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 designed floor plan offers the flexibility and convenience of one-level living--with a bedroom, full bath, laundry, kitchen, dining area, and living room all located on the main level. Love the idea of extra space? The walkout basement provides incredible future potential and may be finished for an additional price--perfect for expanding living space, creating a family room, home office, gym, or guest suite. Enjoy all the benefits of energy-efficient new construction in a location close to walking trails, shopping, healthcare, and everything Bennington has to offer. ?? New Construction ?? 4 Bedrooms | 2 Full Baths ?? Main-Level Living Option ?? First-Floor Laundry ?? Walkout Basement with Expansion Potential ?? Customize Your Finishes ?? Energy Efficient Design Don't wait until it's finished--this is your opportunity to personalize your future home and make it uniquely yours. Reach out today for details and available selections! Listing Agent is owner. See Listing Details & 15 images.
Under Contract
$399,900 $211 per sq.ft. Bennington VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1896 | Acres: 0.33Listed on Monday May 11, 2026
Description: This c. 1936 4BR/2BA home has been beautifully updated to blend timeless architectural character with modern comfort and convenience. Meticulously maintained throughout, it features gleaming hardwood floors, vintage details and thoughtful updates designed for today's lifestyle. The stunning granite kitchen offers rich cherry cabinetry and stainless steel appliances, all new in 2024, creating a warm and functional space for cooking and gathering. The expansive primary suite is a true retreat, complete with an oversized walk-in shower, double vanity with granite countertop, and abundant space to unwind. Three additional guest bedrooms and a full guest bath provide flexibility for family, guests, or home office needs. The finished attic is perfect for a playroom or creative space and the home offers abundant storage throughout. Step outside to enjoy the brand-new expansive deck overlooking the yard, along with a shed and additional outbuilding for hobbies, gardening, or extra storage. Located in the Clarks Woods neighborhood, this charming home is convenient to the country club, hospital, and other local amenities while offering the comfort of a lovely residential setting. 0.33 acre. See Listing Details & 59 images.
New Listing!
$439,900 $176 per sq.ft. Bennington NH Home »
5 Beds | 2 Baths | Total Sq. Ft. 2500 | Acres: 1Listed on 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 Listing Details & 44 images.
$475,000 $53 per sq.ft. Bennington VT Home »
Price Change! Reduced by $24,000 down 5% on June 30th 2026
6 Beds | 6 Baths | Total Sq. Ft. 9000 | Acres: 0.28
Listed on 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 Listing Details & 20 images.
$480,000 $145 per sq.ft. Bennington VT Home »
Price Change! Reduced by $15,000 down 3% on July 29th 2026
4 Beds | 3 Baths | Total Sq. Ft. 3312 | Acres: 56.44
Listed on 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 Listing Details & 54 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
Listed on 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 Listing Details & 37 images.
Under Contract
$550,000 $279 per sq.ft. Village of Bennington in Town of Bennington VT Home »
5 Beds | 2 Baths | Total Sq. Ft. 1974 | Acres: 17.62Listed on 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 Listing Details & 41 images. Includes a Virtual Tour
Under Contract
$565,000 $265 per sq.ft. Bennington NH Home »
4 Beds | 2 Baths | Total Sq. Ft. 2136 | Acres: 1.5Listed on Wednesday Jun 17, 2026
Description: Nestled on a quiet dead-end road right on the Greenfield-Bennington line, this beautifully renovated Cape-style home offers an unparalleled blend of privacy and outdoor adventure. Situated perfectly at the base of Crotched Mountain, the unique property close to hundreds of acres of pristine conservation land, with the Crotched Mountain Hiking Trail accessible right at the end of the driveway. Outdoor living shines with a sprawling composite deck with an attached greenhouse that overlooks well manicured grounds, vibrant gardens, and a patio, all wrapped in serene seclusion. Inside, the feature-rich home boasts exposed beams, built in cabinets, a formal dining room, a dedicated office space, and cozy wood stoves and fireplace to gather around. Full house basement including large main workspace, multiple storage rooms and an attached garage. Complete with a detached 2 car garage and easy access to a charming town beach on Whittemore Lake, this remarkable estate truly has it all--allowing you to walk to the lake, drive to Crotched Mountain in minutes, and fully embrace the quintessential lifestyle of the Monadnock Region. See Listing Details & 32 images. Includes a Virtual Tour
$650,000 $118 per sq.ft. Village of North Bennington in Town of Bennington VT Home »
5 Beds | 3 Baths | Total Sq. Ft. 5524 | Acres: 9.89Listed on Tuesday Jun 9, 2026
Description: Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space combining a kitchen and spacious living room, where a cozy wood stove creates a warm and welcoming atmosphere. Additional living spaces include a formal dining room, private office, library space and a large mudroom with attractive brick flooring that provides a practical transition from the outdoors. Upstairs, you'll find a wonderful studio space ideal for artists, hobbyists, or anyone seeking a creative retreat. The property also boasts a huge, heated workshop, offering endless possibilities for craftspeople, entrepreneurs, or storage needs. Adding to the home's versatility is a second-floor studio apartment with its own private entrance and screened porch, making it ideal for guests, extended family, rental income, or multi-generational living. A substantial barn/garage with a loft area provides even more space for vehicles, equipment, storage, or future expansion possibilities. Recent updates include a newer boiler and hot water heater, providing peace of mind and modern efficiency. The expansive grounds offer privacy and room to roam, while approximately 100 feet of road frontage on Matteson Road may present future building opportunities, subject to local approvals. A rare North Bennington offering that combines space, charm, flexibility, and potential in a beautiful country setting. See Listing Details & 49 images.
$695,000 $626 per sq.ft. Bennington VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1614 | Acres: 14.7Listed on 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 Listing Details & 60 images. Includes a Virtual Tour
