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92,94,96,98,100 Pierce Hill, Bennington
$4,750,000
11 Beds ⋅ 7 Baths ⋅ 5106118 MLS
Located in the heart of the Monadnock Region, reknown for its cultural offerings, close knit communities, protected landscapes and recreational amenities including Crotched Mountain Ski area in town and nearby Crotched Mountain Golf Club. An impressive farm since the early 1800's, Pierce Hill Farm was transformed to a gentleman's estate in 1909. . Its over 306 acres feature extensive hayfields managed by a local farmer, cut stone walls built by Irish masons, gravel carriage roads, walking paths, a private pond, and mountain views. The three story main house has been conscientiously maintained and enjoys lovely grounds with gardens, broad lawn, in-ground pool with patio, tennis court and beautiful views. The first floor boasts large, gracious rooms for entertaining or family gathering. The second floor had a primary suite, two guest bedrooms and four small bedrooms in the kitchen wing. On the third floor are four large bedrooms and two more baths. Also dating from 1909 are the two bedroom, two bath guest house, the five bedroom, two bath farm manager's residence, and the former milk house, now a two bedroom one bath residence. An additional two bedroom 1 bath residence was built in 1961. All the houses enjoy a screened porch with a lovely, private outlook. Farm buildings incude the old dairy barn with slate roof, full hayloft, 2 bay vehicle storage, 4 animal pens and water hydrant. Its attached ell has a tractor bay, box stalls,hayloft, and more animal pens below. The horse barn was built as a showplace with a vaulted two story entry. Clerestory windows light the hayloft below the slate roof. The main aisle is floored with wood bricks and the stall walls have been removed, creating a light open space. The main floor also has a heated workshop, old plumbing, and storage rooms. A full, walkout lower level is used for storage. Additional outbuidings include a garden house, sap house, equipment barn, and old ice house now used for storage.

92,94,96,98,100 Pierce Hill, Bennington
301 Northside Dr, Bennington
$2,190,000
5072776 MLS
Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand drivers. Ideal for investors seeking a site with traffic, frontage, and future upside in an established commercial corridor.

301 Northside Dr, Bennington
1944 Monument Ave, Bennington
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 5105174 MLS
Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom guest cottage. The stunning chef's kitchen is truly the centerpiece of the home, featuring high-end appliances, a dramatic quartz waterfall countertop, and a generous 10-foot island designed for both everyday living and entertaining. Just off the kitchen is a gorgeous screened-in porch, creating a wonderful extension of the living space and the perfect place to enjoy the tranquil setting. Throughout the main level, beautiful white oak floors add warmth and elegance. The home retains the charm and character expected of a historic property while offering the comfort and efficiency of today's modern systems. The thoughtful renovation continues throughout the home, with details such as automated shades in the primary bedroom and library and a convenient second-floor laundry closet. A fireplace adds warmth and character, while expansive views bring the beauty of the surrounding landscape indoors. The separate one-bedroom guest cottage provides even more versatility for guests, extended family, a private office, or potential rental use. Outside, the property is equally impressive, with gorgeous front and side patios designed for outdoor dining and entertaining, a screened-in porch, beautiful grounds, and a storage shed. A rare combination of historic architecture, exceptional renovation, modern technology, expansive acreage, and flexible living spaces, this property offers a level of quality and versatility rarely found in the Bennington market.

1944 Monument Ave, Bennington
153 Northside Dr, Bennington
$997,000
5081713 MLS
Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for financing and insurance. The property’s value is anchored by a substantial, two-story detached storage garage located on the back corner of the lot. This structure is in excellent condition, offering immediate utility for secure equipment storage, a workshop, or contractor inventory while a primary building is being constructed. With 114 feet of direct frontage on Northside Drive and high daily traffic counts, the visibility for signage and branding is exceptional. Located within the Northside Design Review District, this site ensures long-term investment protection, making it a sophisticated gateway location for your next business venture. Ground Lease option available

153 Northside Dr, Bennington
2100 Monument Ave, 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
127-133 Webb St, 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
97 Onset Rd, Bennington
$739,900
3 Beds ⋅ 3 Baths ⋅ 5102468 MLS
Owner-built and thoughtfully maintained, this spacious home offers room for everyone with three bedrooms, three bathrooms, a three-car direct-entry garage with a walk-up attic, and equestrian amenities including a three-stall stable, fenced pasture, and nearby area trails. Follow the slate walkway to the 16' x 25' storage barn, or enter from the covered porch and enjoy the quiet surroundings. Inside, a bright and welcoming foyer opens to a staircase and balcony hall, a private living room with a rock-faced wood-burning fireplace, and a formal dining room with wainscoting. The kitchen features stainless steel appliances, granite countertops, a pantry closet, desk area, breakfast bar, and a sunny breakfast nook that flows into the family room and out to the 11' 15" x 31' 2" rear deck overlooking an owner’s garden area. Hardwood and tile flooring run throughout the home, and all floors are heated with oil-fired radiant heat. The newly renovated primary bath includes a walk-in shower, double sinks, cabinetry with linen storage, tile flooring, and fresh paint throughout. The basement-level recreation room features new flooring, a built-in entertainment center, and a newly constructed bar area with a sink. The walk-out basement also provides an ideal shop or workspace. A place for everyone, this property is only moments from the center of Bennington, skiing at Crotched Mountain, Crotchet Mountain Golf Club and just 4 miles from NH Route 202.

97 Onset Rd, Bennington
370 Southshire Dr, Bennington
$695,000
4 Beds ⋅ 4 Baths ⋅ 5111572 MLS
Welcome to a home that truly has room for it all! Set in a desirable neighborhood on a beautifully landscaped lot, this impressive property offers an incredible amount of living space inside and out. A paved driveway leads to the attached two-car garage, while the backyard feels like your own private retreat with a gorgeous inground pool, spacious patio and beautiful yard perfect for entertaining or simply enjoying summer at home. Inside, you’ll find generously sized rooms and a layout designed for both everyday living and gathering. The kitchen features granite countertops, plenty of cabinetry and a pantry, while the huge family room is made for entertaining with its own bar area and a cozy pellet stove set into the fireplace. A bright sunroom opens directly to the backyard patio and pool, creating wonderful indoor-outdoor flow. The first-floor primary suite offers the convenience of one-level living, complemented by first-floor laundry, a full bath and a handsome office with built-ins. Upstairs, there are plenty of bedrooms plus additional unfinished space above the garage offering even more possibilities: although with this much space, you may never need it! And there’s still more downstairs. The beautifully finished basement adds an entire additional level of living and recreation space, including a game room, home gym, fireplace and plenty of room to spread out. From the expansive interior to the pool, patio and gorgeous grounds, this is a home designed for living big, entertaining well and enjoying every season.

370 Southshire Dr, Bennington
515 Quarry Rd, Bennington
$675,000
4 Beds ⋅ 2 Baths ⋅ 5089246 MLS
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.

515 Quarry Rd, Bennington
3213 West Rd, Bennington
$595,000
5104539 MLS
Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families gathered. In 1970, the roadside farm stand sold fresh corn, tomatoes warm from the sun, potatoes, pumpkins and seasonal produce. Visitors wandered the fields to pick strawberries, while others stopped to find the day's harvest.The farm was home to beef cattle, horses and the flock of nearly sixty geese. The farm supplied local restaurants and markets with potatoes. Today, the old farm stand still watches over the fields, quietly waiting for its next chapter. Whether restored as a seasonal market, transformed into a cider tasting room with a boutique orchard, an artist's studio, or simply enjoyed as part of a beautiful country estate, the possibilities are as expansive as the landscape itself. Beyond the farm stand, the land rises gently through open meadows to what could be an exceptional homesite with panoramic south facing views. Once part of the pasture and hayfields where cattle and horses grazed, this peaceful hillside offers an extraordinary setting for a country home, where mornings begin with birdsong and evenings end with spectacular sunsets. Although it feels wonderfully private, the property is remarkably convenient. A genuine rural lifestyle with easy access to culture, travel and the city. Bennington is minutes away for shopping/restaurants, healthcare and Bennington College. Williamstown 20 min, Albany Int'l Airport & train station 45 min, Boston 3 hrs/Montreal 4 hrs.Some places are purchased, the rare ones are entrusted to their next caretaker. Come see this spectacular property for yourself, walk the land and absorb how special and unique this Vermont property is!

3213 West Rd, Bennington
55 Mcintosh Ln, 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
00 Ross Rd, 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
22 Morse Rd, Bennington
$475,000
5087850 MLS
Positioned in the heart of Bennington’s commercial corridor on 12.82 open acres, 22 Morse Road present a prime development opportunity. Offering excellent visibility and accessibility along one of the area’s primary commercial arteries, the property is ideally situated for a variety of commercial, retail, service, mixed-use, or redevelopment possibilities. The location provides convenient access to both Vermont Route 7 and Vermont Route 279, creating direct connections to Albany and New York’s Capital Region, as well as Southern Vermont and Western Massachusetts. Surrounded by established businesses, national retailers, restaurants, lodging, and employment centers, the site benefits from strong daily traffic counts and regional connectivity. With existing commercial infrastructure and a highly accessible location near the New York and Massachusetts borders, this property offers exceptional potential for investors, developers, or end users seeking a strategic foothold in the greater Bennington market.

22 Morse Rd, Bennington
425 Main St, Bennington
$475,000
6 Beds ⋅ 6 Baths ⋅ 5087015 MLS
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.

425 Main St, Bennington
498 Town Line Rd, Bennington
$460,000
4 Beds ⋅ 3 Baths ⋅ 5095717 MLS
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! Owner relocating. Offer encouraged.

498 Town Line Rd, Bennington
Lot 10-48-1 Old Stagecoach, Bennington
$449,000
3 Beds ⋅ 3 Baths ⋅ 5106158 MLS
UNDER CONSTRUCTION ENERGY STAR HOME WITH UPDATED INSULATION REQUIRING NO FOSSIL FUELS: This charming 3-bedroom Cape offers a comfortable and functional layout with a desirable first-floor primary ensuite bedroom, convenient first-floor laundry, and two additional bedrooms on the second level. The home features stylish vinyl plank flooring and granite countertops, blending modern finishes with everyday practicality. Situated in a quiet residential neighborhood close to town, this property provides easy access to local amenities, golf course, and the popular Crotched Mountain ski area. Conveniently located less than 40 minutes from I-89, I-93, and Concord, this home offers both small-town charm and commuter accessibility.

Lot 10-48-1 Old Stagecoach, Bennington
16 Francestown Rd, Bennington
$434,900
5 Beds ⋅ 2 Baths ⋅ 5102441 MLS
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 "mudroom" 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. The location in Bennington is convenient to Crotched Mountain for skiing, hiking trails, and recreation. The close proximity to Peterborough for shopping, dining, and the arts as well as Hillsborough and Concord, are bonuses. The residence could be converted to two units. A rare chance to bring new life to a charming village home with great bones, character, and potential.

16 Francestown Rd, Bennington
18 Greenview Dr, Bennington
$424,900
4 Beds ⋅ 3 Baths ⋅ 5111091 MLS
Come home to the warmth and character of this inviting 4-bedroom, 2.5-bathroom log cabin, tucked into a desirable Bennington neighborhood on .46 acres. From the welcoming front porch to the cozy interior, this home offers the charm of log construction with plenty of space for comfortable everyday living. The living room is the heart of the home, featuring a fireplace and sliding doors that open to the back deck which creates the perfect atmosphere for relaxing, entertaining, or simply enjoying a quiet evening at home. The spacious primary bedroom offers a private retreat with its own bathroom and walk-in closet, while three additional bedrooms provide plenty of flexibility for family, guests, a home office, or hobbies. A full unfinished basement offers tons of storage and the opportunity to create additional living space, while the 2-car attached garage adds everyday convenience. With both a front porch and back deck, you'll have inviting spaces to enjoy the outdoors throughout the seasons. Full of character, comfort, and potential, this distinctive log home is ready to welcome you home.

18 Greenview Dr, Bennington
479 Us Highway 202, 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
479 Us Highway 202, Bennington
$400,000
5111661 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
2 Bromley Ln, Bennington
$395,000
4 Beds ⋅ 2 Baths ⋅ 5106470 MLS
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.

2 Bromley Ln, Bennington
319 Chester Knoll Dr, 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
527 Jennings Brook Dr, Bennington
$375,000
2 Beds ⋅ 2 Baths ⋅ 5080868 MLS
Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. Custom Kitchen with granite countertops, custom tile shower unit. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy feel. Enjoy year-round comfort with radiant heat throughout and efficient mini-split heat pumps. Step outside to a private back deck: perfect for relaxing or entertaining. A one-car attached garage adds convenience and additional storage. Located in a well-maintained and welcoming HOA, this property offers excellent walkability to nearby amenities, making it ideal for a variety of lifestyles. Listing agent is owner.

527 Jennings Brook Dr, Bennington
291 Spring Hill Rd, Bennington
$355,000
3 Beds ⋅ 2 Baths ⋅ 5104363 MLS
Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons. Inside, the living room opens naturally to the kitchen and dining area, creating a connected space for everyday living and entertaining. A separate family room provides plenty of room to spread out and features a woodstove hookup, ready to add warmth and ambiance on chilly evenings. The four season sunroom is a standout, offering a cozy year round spot for morning coffee, reading, relaxing or simply enjoying the backyard views. The home is ready for some cosmetic updating, offering the perfect opportunity to bring your own style and vision while building on an already comfortable and functional layout. Three bedrooms, a deck overlooking the backyard, attached garage and paved driveway, there's plenty here to work with. Add your personal touches and make this Spring Hill home your own. Some photos have been virtually staged to show you how easy it would be to add a fresh, clean touch of your own!

291 Spring Hill Rd, Bennington
110 Short St, Bennington
$350,000
5101907 MLS
Secure a smart, low-maintenance income property featuring four well-kept units—two 2-bedroom and two 1-bedroom—on a dead-end road. This is turnkey living for tenants and hassle-free ownership for you. Three of the four units have dedicated washer/dryer hookups and each unit is fully separated utilities (electric, gas or oil, hot water), so tenants manage their own bills and turnover is smooth. With reliable, long-term renters in place, enjoy immediate cash flow and minimal management effort. The private setting offers privacy and minimal traffic, while consistent occupancy make this an ideal buy-and-hold investment. Don’t miss this rare opportunity to own a dependable, income-producing asset in an out of the way location.

110 Short St, Bennington
710 Main St, Bennington
$349,000
5102985 MLS
Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental history and varied unit sizes, this property is well-suited for continued use as an investment property or for an owner-occupant seeking the ability to adjust housing needs over time. No showing until the open house on Sunday 8/9 Noon - 2 pm

710 Main St, Bennington
1141 Burgess Rd, Bennington
$330,000
2 Beds ⋅ 2 Baths ⋅ 5106263 MLS
Completely renovated, turnkey single-level home offering mountain views, modern finishes, and a beautiful country setting. All major systems and cosmetic updates were completed within the last year, including a brand-new roof and new windows. The light-filled interior layout features 2 bedrooms, 2 full bathrooms, brand-new wood flooring across all main living areas, plush new bedroom carpeting, and a cozy wood-burning fireplace. Enjoy the modern kitchen and designer bathrooms with high-end contemporary finishes, plus the convenience of an in-unit laundry room built directly into the primary suite's walk-in closet. The home also includes an attached 1-car garage and a huge, clean unfinished basement providing exceptional storage, workshop space, or potential future expansion. Outside, the property is fully set up for relaxation and privacy with a fully fenced backyard, multiple front and rear patios, a detached storage shed, a mature apple tree, and a private, fenced-in hot tub accessible directly via a private door off the primary bath. Conveniently located with quick access to Route 9, local amenities, and outdoor recreation.

1141 Burgess Rd, Bennington
208 Onset 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
683 Water St, Bennington
$319,900
3 Beds ⋅ 2 Baths ⋅ 5084514 MLS
Much larger than it looks and completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an additional bedroom. Outside you'll find a large front yard that has been partially fenced, a large covered, wrapping deck for entertaining and outdoor dining and a dog fenced area. Great location across the road from a calm river. This home is larger than it appears from the road. A must see home in move in ready condition that could possibly sold furnished.

683 Water St, Bennington
314 Chester Knoll Dr, Bennington
$315,000
3 Beds ⋅ 2 Baths ⋅ 5110700 MLS
There is something special about a home that has been truly loved, and you can feel it the moment you step inside. Exceptionally clean, beautifully cared for, and thoughtfully maintained, this inviting three-bedroom home is tucked into a peaceful little neighborhood with nearby walking trails and a stream that adds to the sense of calm and community. Inside, the home feels bright, comfortable, and easy to settle into. The spacious kitchen and dining area is meticulously kept and offers plenty of room for everyday meals, conversation, and gathering. The large front-to-back living room gives you even more space to stretch out, relax, or entertain, with sliding doors leading directly to the deck and bringing the outdoors in. A convenient half bath is located on the main level, while upstairs you’ll find three bedrooms and a full bath. Soft neutral paint throughout creates a fresh, welcoming feel and makes it easy to picture your own style here. A chair lift between floors is already in place, offering an added accessibility feature for those who may benefit from easier movement throughout the home. Outside, the same pride of ownership continues. The exterior is in great condition, a carport provides convenient covered parking, and the surrounding neighborhood offers a lovely setting for evening walks, quiet mornings, and time spent outdoors. This is not just a clean, well-kept house, it is a home that has been cared for with pride and ready for its next chapter. Some photos have been virtually staged to show you just how easy it would be to transform this into a fresh, modern home.

314 Chester Knoll Dr, Bennington

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