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1086 West Rd, Bennington
$1,800,000
9 Beds ⋅ 7 Baths ⋅ 5074314 MLS
Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms, distinguished by 11-foot ceilings on the main level, extensive decorative moldings, and eight fireplaces that create warmth, character, and architectural depth throughout. Elegant formal living spaces flow seamlessly into a grand dining room with rich mahogany floors, perfectly suited for entertaining on an intimate or grand scale. Outdoors, the estate is equally captivating. A heated Gunite pool and expansive stone patio overlook rolling grounds that include a barn, artist’s studio, three-car garage, and a charming three-bedroom caretaker’s cottage-ideal for guests, staff, or extended family. Privately sited yet ideally located on the outskirts of Bennington, the property offers easy access to shopping, fine dining, and live theater, as well as nearby ski mountains and cross-country skiing. Conveniently positioned just 45 minutes from Albany International Airport and approximately three hours from Boston and Manhattan, this extraordinary stone estate presents a rare opportunity to enjoy timeless elegance, exceptional amenities, and an unparalleled Vermont lifestyle.

1086 West Rd, Bennington
16 West Rd, Bennington
$1,495,000
7 Beds ⋅ 6 Baths ⋅ 5075253 MLS
Elegant and stately, this distinguished 1910 home is beautifully set in the heart of Old Bennington, Vermont. Thoughtful renovations began in 2000, carefully preserving the home’s historic character while enhancing comfort and functionality throughout. Offering over 6,000 square feet of gracious living space, the residence features seven bedrooms, six baths, and six fireplaces, with timeless architectural details at every turn. Enter into a large, welcoming foyer highlighted by a grand staircase that sets the tone for the home’s classic elegance. Generous living and gathering spaces flow seamlessly, while the chef’s kitchen enjoys dramatic eastern views, filling the home with morning light. The primary suite is a true retreat, complete with its own fireplace and a large sunroom perfect for quiet mornings or evening relaxation. A convenient second-floor laundry area enhances everyday living. Outside, the 4.5-acre setting is framed by stacked stone walls, a serene spring-fed pond, and lovely birch trees. A two-story carriage barn with garage space complements the property, completing this rare offering where historic beauty, thoughtful updates, and pastoral Vermont charm come together effortlessly.

16 West Rd, Bennington
682-704 Fox Hill Rd, Bennington
$838,500
3 Beds ⋅ 3 Baths ⋅ 5092136 MLS
If you’ve been searching for a home in Vermont and nothing has quite captured what you’re looking for, this is your chance to create it. Set on a quiet, paved road in one of Bennington’s most desirable neighborhoods, this property offers that rare balance: close to everything, yet removed enough to feel peaceful. Morning coffee with mountain views. Evening walks with direct access to the Bennington Area Trail System. A quick drive to SVMC, Bennington College, and downtown—yet home still feels like your own retreat. Albany International Airport is just an hour away when you need it. A thoughtfully designed single-level home is currently envisioned, centered around open, connected living spaces with easy access to the outdoors, a covered front porch, and an attached garage. But this is not a one-size-fits-all build—and that’s the point. This is your chance to shape how your home lives. Prefer a different layout? A more modern aesthetic? A classic Colonial with all the bedrooms upstairs? Need to reconfigure the garage—or expand the footprint? We can adjust, redesign, or start from scratch. Every decision, from the big picture to the smallest details, is an opportunity to create a home that reflects your lifestyle—not someone else’s. You’ll work directly with a trusted local builder with over 40 years of experience, guiding you through a process that is collaborative, thoughtful, and grounded in craftsmanship. The result isn’t just a new house—it’s a home designed with intention, built for how you actually want to live. Offered as a land and construction package. A rare opportunity to create something truly your own in a location that’s becoming harder to find. Seller is a Vermont licensed real estate broker.

682-704 Fox Hill Rd, Bennington
134 Monument Ave, Bennington
$665,000
3 Beds ⋅ 3 Baths ⋅ 5065403 MLS
Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary suite on the main level provide convenience and flexibility. Upstairs, you’ll find two generous bedrooms, a full bath, and a cozy den area perfect for reading or quiet work. Step outside to enjoy the large slate patio framed by handsome stacked stone walls or unwind on the private Trex deck overlooking the .75-acre lot. A rare blend of charm and space just minutes from the historic village of Old Bennington.

134 Monument Ave, Bennington
34 Monument Ave, Bennington
$625,000
4 Beds ⋅ 3 Baths ⋅ 5099185 MLS
Set along tree-lined Monument Avenue in prestigious and historic Old Bennington, the Spargo House offers a rare opportunity to own a distinctive piece of Vermont history. Dating to circa 1800, this remarkable home was once the longtime residence of noted author, historian and collector John Spargo, founder and longtime director of the Bennington Museum. Just below the Bennington Battle Monument, the home blends historic character with thoughtful updates throughout its 2,692 square feet of living space. The bright kitchen features abundant cabinetry, generous counter space, stainless appliances and a center island, while exposed brick, arched openings and period details preserve the character of the home. Four bedrooms include an expansive primary suite with an exposed beam, sitting area, recently renovated bath and convenient in-suite laundry, while mini-split cooling adds modern comfort throughout the home. Outside, the deep one-acre lot stretches from Monument Avenue to Catamount Lane, offering access from both ends and exceptional space for gardens, recreation and outdoor living. A spacious back deck with a powered retractable awning provides a comfortable place to relax or entertain, while mature trees and established landscaping complement the home's historic setting. A distinctive stone-lined approach leads from the driveway to the home, adding to the character of the property. Enjoy the convenience of nearby golf at Mt. Anthony Country Club, Southwestern Vermont Medical Center, the William H. Morse State Airport, downtown Bennington and the cultural and historic landmarks that make Old Bennington one of Vermont’s most distinctive communities. A home with history, character, space and an extraordinary setting that's ready for its next chapter.

34 Monument Ave, Bennington
19 Rogers Rd, Bennington
$565,000
4 Beds ⋅ 2 Baths ⋅ 5095203 MLS
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.

19 Rogers Rd, Bennington
58 Mount Anthony Rd, Bennington
$505,000
3 Beds ⋅ 3 Baths ⋅ 5067086 MLS
Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized kitchen is perfection for entertaining and for spending time with family and friends. The living room invites a space for conversation, a cozy fire during the chilly Vermont evenings, or simply relaxing taking in the divine views at sunset. More casually, the family room offers exposed beams, vaulted ceilings and abundance of natural light. A formal dining room is strategic to the kitchen for holidays and family gatherings. The second floor boasts three bedrooms and two bathrooms, while the third bath is on the first level for convenience. And have I mentioned the renovated space above the garage? Wow! Breathe in the fresh air, take a walk up a country road and hunker down for the most genuine, spectacular sunsets. This is the type of special property that you will not want to miss.

58 Mount Anthony Rd, Bennington
4 Stonehedge Dr, Bennington
$500,000
3 Beds ⋅ 3 Baths ⋅ 5082188 MLS
Beautiful 3-bedroom, 3-bath home offering stunning views from a spacious two-tier deck-perfect for relaxing or entertaining. Designed for comfortable main-level living, the home features a generous primary suite and an open, light-filled living room with a dramatic wall of windows that captures the surrounding scenery. Warm and inviting, the home includes two gas fireplaces, gleaming wood floors, and a low-maintenance lifestyle ideal for year-round enjoyment. The kitchen is appointed with granite countertops and a convenient slider leading directly to the deck-perfect for easy outdoor grilling. The walk-out lower level offers exceptional flexibility, featuring a large family room, cozy library area, cedar closet, and an expansive craft room or office that could easily be converted into an additional bedroom. With its layout and private access, the lower level presents great potential for an in-law apartment. A standout feature is the 10x26 workshop, complete with a dust collection system already in place—ideal for woodworking or hobbyists. The home is equipped with central air, 200-amp electrical service and is wired for a generator, providing added convenience and peace of mind. Additional highlights include a partially fenced yard and an attached two-car garage, completing this well-rounded and inviting property.

4 Stonehedge Dr, Bennington
82 Pine Meadows Cir, Bennington
$480,000
3 Beds ⋅ 3 Baths ⋅ 5102749 MLS
Welcome to this beautifully maintained Cape-style home in the desirable Pine Meadows neighborhood of Bennington. At only 6 years young and meticulously maintained, this move-in ready home offers the perfect combination of modern construction, energy efficiency, and comfortable living space. The thoughtfully designed floor plan features a sought-after first-floor primary suite with a walk-in closet and private full bath, providing the convenience of single-level living. The bright, open-concept kitchen, dining, and living areas create an inviting space for everyday living and entertaining. Just off the kitchen, a stunning 10' x 20' sunroom extends your living space and serves as the perfect spot to enjoy morning coffee, unwind with a book, or host guests. With direct access to the backyard, it creates a seamless connection between indoor and outdoor living. Upstairs, you'll find two additional bedrooms both with walk-in closets and a full bath between them, while the finished lower-level bonus room offers excellent flexibility as a family room, home office, fitness area, or hobby space. Year-round comfort is provided by an efficient Buderus boiler and a five-head mini-split system offering heating and cooling throughout the home. Additional highlights include a two-car attached garage, generator-ready electrical setup, paved driveway, first floor laundry, and a beautifully maintained one-acre lot offering space to relax, garden, and enjoy the outdoors. Conveniently located just minutes from downtown Bennington, Antrim, Peterborough, hiking trails, golf, and the many amenities of the Monadnock Region, this exceptional home offers the ideal balance of peaceful neighborhood living and modern convenience. With quality construction, thoughtful upgrades, and meticulous care throughout, this is a home you'll be proud to own.

82 Pine Meadows Cir, Bennington
8 Main St, Bennington
$480,000
5073533 MLS
WELCOME HOME!!! This charming Colonial style home is completely renovated and awaits you! 2 units; perfect opportunity to owner occupy one unitand rent out the other, perfect in law opportunity or rent out both as an investment. As you enter into the first unit you will find it is tastefully updated throughout! Stunning eat in kitchen with dining area and eat up bar, spacious living room with tons of natural light and sitting area, lovely full bathroom boasting tiled surround, shiplapped walls and stunning fixtures. Large laundry room with space for workout area, office or storage. Upstairs features two spacious bedrooms with closets and room for many! Let's not forget the charming enclosed porch; perfect for reading, lounging or anything you choose. Hot water baseboard heat as well as a Parlor stovefor a secondary heat source. The second unit doesn't disappoint either!!! Brand new everything!! As you enter the fully applianced kitchen you will be in awe. Tastful cabinetry and countertops as well as lovely fixtures and a large pantry. Open concept dining and living room. Spacious bathroom with large tiled shower and a separate laundry area just outside the bathroom. 2 expansive bedrooms complete this unit. Outside boasts an attractive patio for grilling and enjoying those warm nights, semi secluded back yard, covered side entry and large barn for all of your storage needs. Close to amenities; stores, restaurants, library and schools!!! Such an amazing homeand amazing opportunity!!!

8 Main St, Bennington
32 Cortland Ln, Bennington
$450,000
3 Beds ⋅ 3 Baths ⋅ 5079776 MLS
This well-maintained 1999 Colonial offers the perfect blend of timeless design, functional space, and peaceful surroundings in a desirable neighborhood just outside of town. Set on a wooded lot with a wrap-around covered front porch, this home invites you to slow down and enjoy the best of Vermont living. Inside, you’ll find over 2,100 square feet of thoughtfully designed living space with a bright, spacious layout. The oversized living room with hardwood floors and a cozy gas fireplace creates a warm and welcoming gathering space, while the adjacent dining room flows seamlessly into the kitchen—ideal for everyday living and entertaining. The kitchen features granite countertops, abundant cabinetry, a center island with seating, and a large pantry with shelving and coat closet. A half bath and versatile den—perfect for a home office or additional living space—complete the main level, along with direct entry to the attached two-car garage. Upstairs, the home offers three spacious bedrooms and two full baths, including a comfortable primary suite with walk-in closet. Mini split heat pumps provide energy efficient cooling, with units located in the den and primary bedroom for targeted comfort. The full, dry basement offers laundry space and excellent storage, with potential for future finishing. High-speed internet is available via cable, with the option to install fiber optic service. Outside, the flat backyard features a privacy fence, two sheds for additional storage, and a portable generator for added peace of mind. A quiet, wooded backdrop enhances the home’s privacy and peaceful Vermont setting. Whether you're relaxing on the covered porch, hosting gatherings, or simply enjoying the surroundings, this home delivers comfort, space, and value in one of Bennington’s most convenient locations.

32 Cortland Ln, Bennington
125 Pine Meadows Cir, Bennington
$440,000
3 Beds ⋅ 3 Baths ⋅ 5087236 MLS
Welcome to this like-new Colonial in desirable Bennington, NH, offering the perfect blend of modern living and peaceful country charm. Built in 2018, this 3-bedroom, 2.5-bath home features thoughtfully designed space set on a private 1.6-acre lot. Inside, you’ll find a bright, comfortable layout ideal for everyday living. The kitchen flows seamlessly into the dining and living areas, while a finished bonus room in the basement provides flexible space. Upstairs, the primary suite offers a comfortable retreat with its own bath and walk-in closet, along with two additional bedrooms and a full bathroom. Enjoy quality systems including a Buderus boiler, HTP hot water tank, water softener, and portable generator hookup for added peace of mind. Outside, the property is set up for lifestyle, featuring a deck, firepit area, shed, chicken coop, and plenty of open space for recreation, whether it’s a play area, swing set, or future pool. Located near the rail trail, Contoocook River, and Crotched Mountain, this home is perfect for outdoor enthusiasts while still offering convenience just 15 minutes to Peterborough, 40 minutes to Keene, 1 hour to Manchester, and 1.5 hours to Boston. A great opportunity to enjoy newer construction, privacy, and access to everything the Monadnock region has to offer.

125 Pine Meadows Cir, Bennington
15 Polygraphic Ln, Bennington
$439,000
3 Beds ⋅ 3 Baths ⋅ 5097821 MLS
At the end of a quiet road in North Bennington, this beloved 1979 home is being offered for the first time by its original owner. Set on over an acre with a large private backyard, garden beds, wild blackberries, and a peaceful wooded backdrop, the property feels beautifully tucked away while remaining just a short walk to the Henry Bridge and the Walloomsac River. Inside, the home is timeless, warm, and wonderfully livable, with approximately 2,389 finished square feet, hardwood floors throughout, fresh interior paint, and abundant natural light. The main level offers a large living room with built-in shelving, an inviting kitchen and dining area, a mudroom entry, first-floor bedroom, full bath, and a den that provides versatile space for guests, hobbies, or everyday living. Upstairs, the flexible layout features two bedrooms and two bathrooms, a spacious office, generous closet space, a built-in dresser, and a Mitsubishi mini split for added comfort. The lower level expands the living space with a finished family/recreation room, laundry, storage, utilities, and updated mechanicals including a Buderus boiler and five heat zones. A separate exterior entrance leads to a large workshop, ideal for tools, projects, outdoor equipment, or creative use. Additional conveniences include public water and sewer, high-speed internet, cable, and school choice for kindergarten through sixth grade. With its wrap-around deck, natural wood trim, built-ins, generous windows and skylights, end-of-road privacy, and unmistakable sense of care, this is a rare North Bennington opportunity with space, flexibility, and enduring Vermont charm. Homes with this setting, history, and location do not come along often.

15 Polygraphic Ln, Bennington
Lot 10-48-2 Old Stagecoach, Bennington
$436,400
3 Beds ⋅ 2 Baths ⋅ 5080205 MLS
Stunning split-level home in a close-to-town location offers the perfect blend of comfort and convenience. With 3 bedrooms, 2 bathrooms, and 1219 sq ft of living space, this open concept gem is ideal for families & those seeking a spacious retreat. Step inside and be greeted by a beautifully designed kitchen/dining/living area. The seamless flow allows for easy entertaining and quality family time. The kitchen boasts ample storage space, granite countertops & a center island. The primary bedroom comes complete with an en-suite bathroom for privacy and convenience. 2 additional well-appointed bedrooms provide space for guests, children, or a home office. Enjoy the low maintenance vinyl plank flooring throughout the home, providing both durability & a sleek aesthetic. With easy-to-clean surfaces, you can spend less time worrying about maintenance & more time enjoying your new home. Parking is a breeze with the two-car garage located underneath the home, providing shelter for your vehicles and additional storage options. Step outside onto the rear deck and unwind in the fresh air. It's the perfect spot for barbecues, coffee, or reading your favorite book. Conveniently situated close to town, golf course and Crotched Mtn ski area, this home offers the best of both worlds - a quiet residential area w/easy access to everything you need. Located less than 40 minutes from Concord and I-93, ensuring a convenient journey for work or leisure.

Lot 10-48-2 Old Stagecoach, Bennington
131 Pine Cir, Bennington
$408,000
4 Beds ⋅ 3 Baths ⋅ 5087824 MLS
A must-see! Nestled in a quiet neighborhood just minutes from downtown dining and shopping, this beautifully maintained home offers comfort, flexibility, and thoughtful upgrades throughout. Completely renovated approximately 10 years ago, the home features a well-designed gourmet kitchen with granite countertops, a copper sink, soft-close cabinetry, and a custom built-in wine rack. French doors lead to a charming screened porch, perfect for relaxing or entertaining. The upper level offers three bedrooms, including a spacious primary suite with a private ensuite bath, as well as an additional full bathroom. A separate first-floor bedroom w/living space is currently being used as an in-law suite with its own private feel, offering excellent potential for guest accommodations, multigenerational living, or possible Airbnb/rental income. Sliding doors open to a stone patio and a semi-wooded backyard offering privacy and seclusion. Additional highlights include a large attached two-car garage, a semi-finished basement with ample storage space, a newer roof and gutters, paved driveway with drainage system, newer garage door, and updated furnace. The major improvements have already been taken care of — simply move in and enjoy. Schedule your showing today!

131 Pine Cir, Bennington
307 North St, Bennington
$405,000
5077756 MLS
Exceptional mixed-use opportunity in Bennington’s MU-2 District. Sale includes 307 & 307.5 North Street on one 0.70-acre parcel with approximately 150 feet of frontage along North Street (VT Route 7). The front building (approx. 3,446 SF, c. 1840) is currently configured for professional office use with reception, private offices, meeting rooms, kitchen space, and updated mechanical systems. The detached rear structure (approx. 1,200 SF) is a 3BR residence providing supplemental income or on-site occupancy potential. Flexible zoning supports residential, commercial, or mixed-use configurations (subject to approvals).

307 North St, Bennington
848 Coleville Rd, Bennington
$405,000
4 Beds ⋅ 3 Baths ⋅ 5065182 MLS
The House that Love Built-Multigenerational Comfort &Thoughtful Design Tucked away in a peaceful neighborhood, set back from a well maintained town road. This beautifully maintained home is perfect for wildlife watching and enjoying serene solitude. Designed with multigenerational or accessible living in mind, the home features a private in-law suite with it's own ramp entry, wide doorways, and a custom roll in shower. Just outside the suite, enjoy a private deck offering easy access and a peaceful place to relax. The main level includes custom woodwork, hardwood floors, passive solar windows, and fresh paint throughout. The cozy kitchen has a window over the porcelain sink, a pantry and newer appliances. Upstairs features new vinyl flooring, a sunlit primary bedroom, a second spacious bedroom, and a full bath. Bonus features include a 3-year old roof with leaf guard gutters, A Webb Pro Boiler (recently serviced) and a 15kw backup generator. The laundry offers front-load washer/dryer, a sink and access to a 448 sq ft attic roughed in for future living space (with plumbing, heating and structural framing in place). Peaceful setting, thoughtful design-this truly is The House That Love Built.

848 Coleville Rd, Bennington
15 Eaton Ave, Bennington
$400,000
3 Beds ⋅ 2 Baths ⋅ 5089639 MLS
HISTORIC CHARM MEETS MODERN COMFORT AND A SETTING THAT SHINES IN EVERY SEASON! Perfectly positioned to capture morning and afternoon sunlight and maximize sweeping sight lines across the land, this thoughtfully updated historic home blends character with practical improvements for modern living. Inside, neutral tones and wood-look vinyl flooring create a welcoming backdrop while the open-concept layout encourages connection from room to room. The bright white kitchen draws guests in to linger around the bar counter with appetizers and refreshments while conversation flows. Clever built-in banquette seating defines the eat-in kitchen inviting everything from lively card games and homework sessions to holiday brunches and memorable dinners with friends. On football Sundays or movie nights, the cook will appreciate clear sight lines into the family room where everyone can be part of the action. Enjoy changing seasonal views of a flowering cherry tree and expansive yard that provides a beautiful backdrop for outdoor play, gardening or evenings under the stars. A rustic outbuilding with chicken coop offers the perfect start for homesteading dreams and the simple pleasure of gathering fresh eggs each morning. Back inside, a versatile collection of rooms adapts to evolving needs. A multipurpose room with built-in organization and laundry keeps things tidy, while just beyond knotty pine offers wonderful flexibility as primary bedroom, or even a bunk area for ski weekends or bonus guest suite complete with ensuite bath. After a day spent skiing or golfing at nearby Crotched or biking the rail trail recreation corridor, the second-floor bedroom with cathedral ceiling and calming coastal-inspired tones is a welcome escape. A second light-filled bedroom delights guests while an oversized landing can serve as an office, reading nook or study zone. FROM SKI WEEKENDS TO SUMMER GARDENS, THIS IS A HOME TO LOVE FOR YEARS TO COME!

15 Eaton Ave, Bennington
23 Pageant St, Bennington
$399,900
4 Beds ⋅ 2 Baths ⋅ 5088223 MLS
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.

23 Pageant St, Bennington
231 Washington Ave, Bennington
$398,000
3 Beds ⋅ 2 Baths ⋅ 5084174 MLS
Charming vintage 1920s Arts & Crafts-style cottage in a prime village location. This inviting home offers seven main rooms, including three bedrooms and two baths, blending timeless character with modern comfort. The updated kitchen features abundant storage and flows nicely into the living spaces, highlighted by beautiful wood floors and a cozy fireplace. Central air ensures year-round comfort. Enjoy outdoor living with a large, inviting front porch perfect for relaxing, as well as a private back deck ideal for entertaining or a quiet retreat. A two-car detached garage adds convenience and additional storage. Classic architectural details and thoughtful updates make this a truly special property in a highly desirable setting.

231 Washington Ave, Bennington
185 Jewett Dr, Bennington
$389,000
3 Beds ⋅ 2 Baths ⋅ 5103003 MLS
Welcome home to this 3-bedroom, 2-bath raised ranch nestled on 1.72 beautifully landscaped acres in a peaceful neighborhood. The picturesque property is adorned with a variety of mature fruit trees and offers stunning mountain views. A spacious back deck overlooks the above-ground pool, making it the perfect setting for relaxing, entertaining, or taking in the scenery. Inside, you'll find an oversized, updated kitchen featuring soft-close cabinetry and plenty of space for gathering. The breakfast nook overlooks the inviting living room, where a cozy pellet stove creates a warm and welcoming atmosphere. A formal dining room provides additional space for hosting family and friends. The mostly finished basement offers endless possibilities, whether you're looking for a recreation room, home office, workout space, or the ultimate man cave, while still providing ample storage. The heated two-car garage is equipped with an electric vehicle charger, adding modern convenience to this thoughtfully cared-for home. Combining comfortable living spaces, beautiful outdoor amenities, and a sought-after location, this home is ready for its next chapter!

185 Jewett Dr, Bennington
317 Chester Knoll Dr, Bennington
$388,800
4 Beds ⋅ 2 Baths ⋅ 5092590 MLS
Brand New Construction in Bennington! Looking for the perfect blend of modern comfort, energy efficiency, and outdoor adventure? This stunning new construction home has it all! Featuring 4 spacious bedrooms, 2 full baths, and thoughtfully designed living spaces, this home was built with today’s lifestyle in mind. Enjoy lower utility costs and year-round comfort thanks to its energy-efficient construction. Step outside onto the expansive back deck, the perfect place to host summer barbecues, sip your morning coffee, or unwind while taking in the peaceful surroundings. Love the outdoors? You’ll appreciate the nearby walking trails that connect you to the beautiful grounds of the Bennington Museum and beyond. Plus, you’re just minutes from the hospital, shopping, dining, and everything Bennington has to offer. Brand New Construction 4 Bedrooms | 2 Bathrooms Energy Efficient Design Huge Rear Deck Walking Trails Nearby Convenient Location Close to Shopping & Healthcare This is more than a house—it’s a lifestyle. Agent is seller.

317 Chester Knoll Dr, Bennington
328 Chester Knoll Dr, Bennington
$386,000
3 Beds ⋅ 4 Baths ⋅ 5075963 MLS
Well-maintained 2005 tri-level home offering comfortable, easy living in a desirable residential neighborhood. Features include efficient radiant floor heat, mini-split system for added comfort and new vinyl plank flooring on the lower and main levels. The kitchen is outfitted with attractive cherry cabinets and offers a functional layout for everyday living. Located within a PUD, the HOA covers landscaping, snow plowing, and trash removal—ideal for low-maintenance living. Conveniently situated close to downtown Bennington, the Bennington Museum, shopping, dining, and local amenities.

328 Chester Knoll Dr, Bennington
185 Us Highway 202, Bennington
$384,900
5097060 MLS
Some houses have character. This one has personality. Set in the heart of Bennington, this classic New England farmhouse has the kind of details that stop you mid-tour: wide pine floors, wainscoting, rich wood accents, stained glass windows, and built-ins tucked into all the right places. It's the sort of home that feels lived-in and loved, without feeling dated. The main house offers two bedrooms and two baths upstairs, plus a flexible bonus room just off the primary bedroom, ideal as a nursery, home office, or reading nook depending on what life looks like for you. Downstairs, a fully separate one-bedroom apartment with its own private entrance adds serious versatility. Multi-generational living, rental income, a guest suite, a home studio: the options are there. Outside, a fully fenced yard gives you room to garden, let the dog run, or just breathe. The attached two-car garage handles the practical side of things, and the detached 20x40 barn (two full floors of it) handles everything else. Tools, equipment, hobbies, overflow storage: it's all accounted for. This is the kind of property that doesn't come around often in a town this charming. Come see it for yourself.

185 Us Highway 202, Bennington
303 Prospect St, Bennington
$372,000
3 Beds ⋅ 2 Baths ⋅ 5080054 MLS
Nestled on a quiet residential street, this beautifully maintained home effortlessly blends timeless charm with modern convenience, creating a space that is as inviting as it is impressive. From the moment you arrive, you’ll appreciate the character and warmth that set this property apart. At the heart of the home is a thoughtfully designed kitchen featuring modern appliances, rich cherry cabinetry, and granite countertops. With abundant storage and a dedicated pantry, the space is both functional and perfect for entertaining. Graceful arched doorways lead into the dining and living areas, where gleaming hardwood floors and an abundance of natural light create a bright, welcoming atmosphere. A cozy pellet stove adds warmth and comfort during cold Vermont winters. Upstairs, you’ll find three bedrooms, including a versatile smaller room ideal for a home office, nursery, or guest space, along with a spacious full bathroom. The basement has been sealed and painted and is perfect for storage or added recreation space. Outside you'll enjoy a manageable, level yard accented by established flowerbeds and lovely views of Mount Anthony. A beautiful, maintenance-free deck offers an ideal space for relaxing or entertaining in a peaceful setting. A standout feature of the property is the expansive four-car garage, offering exceptional space for vehicles, hobbies, or a workshop, along with a generous overhead storage area to keep everything organized. The home is also thoughtfully equipped to support modern living with wiring in place for an electric vehicle charging station as well as generator readiness for added peace of mind. An ideal location close to downtown shops and restaurants, yet just a few blocks from the Y Woods walking trails. You truly can have it all!

303 Prospect St, Bennington
12 Hall St, Bennington
$365,000
3 Beds ⋅ 2 Baths ⋅ 5101687 MLS
Located in the heart of the charming North Bennington Village, this beautifully renovated home offers the perfect blend of classic character and modern convenience. Completely renovated interior in 2022, including a new roof, this move-in-ready home features three bedrooms and two beautifully updated bathrooms, with the added convenience of a first-floor bedroom and main-level laundry. The spacious kitchen is designed for both everyday living and entertaining, featuring a gas range, pantry, and ample cabinetry. The flexible living and dining area is highlighted by a cozy fireplace, while gleaming hardwood floors run throughout the home. An enclosed front porch serves as the perfect mudroom or welcoming entry, and the bright living room is filled with natural light. Upstairs, you'll find two additional bedrooms and a beautifully tiled bathroom with a walk-in shower. The home's extensive 2022 renovation included a new roof, furnace, electrical, plumbing, and insulation, along with updated finishes throughout, providing the comfort and peace of mind of a nearly new home. Outside, enjoy a partially fenced yard, ideal for gardening, pets, or outdoor gatherings, along with a detached one-car garage. Located within walking distance of North Bennington Village's shops, restaurants, parks, and local amenities, this thoughtfully renovated home is truly move-in ready.

12 Hall St, Bennington
169 Us Route 202, Bennington
$360,000
2 Beds ⋅ 1 Baths ⋅ 5084696 MLS
Welcome to 169 US Route 202 — Where Modern Living Meets New Hampshire Adventure. Bright, clean, and move-in ready, this stylish 2-bedroom, 1-bath home in the heart of Bennington offers the perfect blend of modern design and outdoor lifestyle. From the moment you step inside, you'll notice the sun-drenched interiors and sleek finishes that give this home a fresh, contemporary feel. The kitchen shines with stainless steel appliances, with the layout flowing effortlessly into a versatile flex room — currently used as a living area — giving you the freedom to make the space truly your own. Step right outside of the current living room and the fun continues. Situated on a generous .75-acre lot, the concrete patio is perfect for entertaining, and the yard comes complete with a trampoline and swing set — ready for everything summer has to offer. With Sawyer Park just a short walk away, as well as Powder Mill Pond trails and access to Powder Mill Pond minutes away, nature is practically at your doorstep. Crotched Mountain Ski Resort and the Crotched Mountain Golf Club are just minutes away, giving you four seasons of adventure right outside your door. Rounding it out: forced hot air heat, an unfinished basement offering excellent storage or future potential, and 1,124 sq ft of thoughtfully designed finished living space. Schedule your showing today! OPEN HOUSE SATURDAY 4/25 10:00am-12:00pm!!

169 Us Route 202, Bennington
695 Dermody Rd, Bennington
$355,000
3 Beds ⋅ 2 Baths ⋅ 5081523 MLS
This inviting ranch has been thoughtfully cared for and filled with warmth throughout. What truly sets it apart is the location, offering wide, beautiful views you can enjoy everyday. The level lot provides plenty of space for gardening, outdoor gatherings, or simply relaxing on the back deck with a morning cup of coffee, or an evening star gazing. With generous road frontage, the possibilities for outdoor living are wide open. Inside, the home features three bedrooms and two bathrooms. The spacious primary bedroom includes its own half bath and a versatile sunroom with a sitting area, or a space of your own design. The two additional bedrooms face west, bringing in soft afternoon light. The kitchen and dining area have a great flow for families, or entertaining. The living room offers a comfortable gathering space with a working fireplace for cooler nights.You will love the large laundry room on the first floor for convenience. In the cellar, you'll find a new heating system that was installed in 2025. The house is equipped with a generator. *Bonus*- the basement is framed and ready to go for extra living space.This is a special property with a lot to offer. I'd love to show it to you!

695 Dermody Rd, Bennington
38 Oak Ridge Ln, Bennington
$354,000
3 Beds ⋅ 2 Baths ⋅ 5073481 MLS
Convenient one-level living meets modern style and design in this beautifully crafted ranch home, situated on a spacious 1.4-acre lot within a newer, private four-home subdivision. Relax on the impressive 52-foot farmer’s porch, perfect for enjoying cool summer breezes, stunning sunsets, entertaining guests, or simply taking in the expansive yard and thoughtfully designed plantings. Inside the open floor plan showcases a stylish kitchen with stainless steel Whirlpool appliances, a walk-in pantry, farmhouse sink, and center island w/ seating, seamlessly flowing into the living room highlighted by a tray ceiling and custom built-in entertainment center. The oversized primary suite offers a private retreat with a spa-like bath, including his-and-her vanity, a glass-enclosed palisade shower, built-ins, window seat, and a generous walk-in closet. The opposite end of the home includes two additional bedrooms, a full bath, and a spacious laundry room with abundant storage. The slider leads out to the covered back deck and overlooks the private, fenced-in backyard. Additionally, the home offers low maintenance flooring, recessed lighting throughout, forced hot air heat via propane, 100 amp electrical, town water, private septic, and Vermont Weatherization including upgraded insulation. Expansion potential for a future garage adds even more value. Constructed in 2023, it is truly move-in ready and offers a wonderful opportunity to create lasting memories. This property is in close proximity to historic downtown Bennington and is just 30 minutes from Manchester VT and Williamstown MA. Additionally, it is within approximately 45 minutes of several ski resorts in Vermont (Mount Snow, Stratton Mountain, and Bromley Mountain) and Massachusetts (Jiminy Peak).

38 Oak Ridge Ln, Bennington
308 Elm St, Bennington
$353,000
3 Beds ⋅ 3 Baths ⋅ 5076747 MLS
Vermont charm meets move-in ready comfort on Elm Street! This inviting 3-bedroom, 2.5-bath Cape offers warm, welcoming spaces throughout. The cozy yet spacious living room features a fireplace — perfect for snowy Vermont evenings — while the generously sized dining room is ideal for hosting holidays and gatherings. The beautifully updated kitchen showcases granite countertops and rich cherry cabinetry, blending classic style with modern convenience. The primary bedroom includes a walk-in closet, and all bedrooms offer comfortable, spacious layouts. Enjoy your morning coffee on the charming front porch or unwind on the back deck overlooking the lovely yard. A detached two-car garage adds practicality and storage. A truly special home that captures Vermont character with the ease of modern updates — ready for its next chapter.

308 Elm St, Bennington

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