You are viewing all listings Homes between $250000 and $500000 dollars.
$269,000 $200 per sq.ft. Village of Bennington in Town of Bennington VT Home »
Price Change! Reduced by $26,000 down 10% on July 27th 2026
3 Beds | 1 Baths | Total Sq. Ft. 1344 | Acres: 0.25
Listed on Thursday Apr 16, 2026
Description: This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back deck. Featuring replacement windows for energy efficiency, a paved driveway, and ample yard space, this property is ideal for anyone seeking extra room to play and entertain. Sidewalks and streetlights make evening strolls safe and pleasant, and the proximity to downtown ensures you're close to shopping, dining, and public transportation. For outdoor enthusiasts, the location is unbeatable: just 10 minutes from Prospect Ski Area, 30 minutes to Mt. Snow, 45 minutes to Albany Airport, 3 hours to New York City or Boston, and 2 hours to Hartford. This home is ready for your finishing touches to make it truly your own. See Listing Details & 45 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
$275,000 $205 per sq.ft. Bennington VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1526 | Acres: 0.21Listed on Thursday Apr 30, 2026
Description: Welcome to this lovely Colonial home, formerly a charming carriage house, nestled in one of Bennington's most desirable walkable neighborhoods. Offering over 1,500 square feet of inviting living space, this well maintained home features 3 bedrooms, 2 bathrooms, and a versatile bonus room perfect for a home office or potential fourth bedroom. Inside, you'll find beautiful wood floors and trim, rustic beams, and newly installed plush carpeting. The sunny interior is filled with natural light thanks to large windows that flood the home with brightness. The kitchen offers stainless steel appliances direct access to the back deck. Updated bathrooms and ample closet space blend modern convenience with the timeless charm of the home. Step outside to enjoy the beautifully landscaped yard, complete with a newly painted deck ideal for entertaining and gatherings, as well as stunning mountain views. The level, usable yard offers plenty of space for outdoor enjoyment, room for a garden, and a large paved driveway accommodates up to six vehicles. A generously sized shed offers perfect storage for your outdoor items. Additional highlights include low-maintenance vinyl siding, replacement tilt-out windows for easy cleaning, and an updated metal roof. In the basement you will find a finished rec room, laundry area and extra storage with peg wall for your tools and a sump pump. Connected to town water and sewer, this home offers added ease of maintenance. Enjoy the peace and comfort of this quiet neighborhood while being just minutes from the hospital, shopping, and vibrant downtown Bennington. An hour from Albany International Airport, close to all Southern Vermont and the tri-state area has to offer. A true gem in the heart of town--you won't want to miss this one! See Listing Details & 34 images.
Under Contract
$275,000 $248 per sq.ft. Bennington VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1302 | Acres: 1.84Listed on Friday Jul 17, 2026
Description: Tucked into a private wooded setting on the outskirts of town, this distinctive 3-bedroom, 1.5-bath Adirondack-inspired chalet blends rustic character, flexible living space, and an exceptional connection to the outdoors. Its steep roofline, front balcony, exposed beams, and metal roof give the home memorable architectural presence, while the peaceful surroundings create a true retreat from the everyday. Inside, hardwood floors and dark ceiling beams add warmth and character to the main living and dining area, where a propane stove set against a brick hearth creates a cozy focal point. Brand-new windows throughout bring in abundant natural light, complemented by new French doors that open directly to the deck. The efficient kitchen offers generous cabinetry and slate-finish appliances, all included. An adjacent unfinished mudroom provides an opportunity to create a convenient entry and additional storage. A main-level bedroom and full bath offer the flexibility of one-floor living, comfortable guest accommodations, or work-from-home space. Upstairs, two bedrooms feature dramatic cathedral ceilings and exposed beams. One opens to a private covered balcony overlooking the yard and woods... an inviting place to enjoy morning coffee, read, or simply take in the quiet surroundings. A half bath completes the upper level. The basement adds valuable versatility with a laundry room, finished bonus room, workshop, and utility room. The detached 1-car garage provides even more space for a vehicle, tools, equipment, or recreational gear. Outside, there is plenty of room to enjoy every season, including a spacious deck, fire pit, private backyard, multiple woodland trails, and a charming screened outbuilding for bug-free relaxation, dining, or summer gatherings. Full of personality and surrounded by nature, this wonderfully distinctive Vermont home offers space to live, work, gather, and unwind. See Listing Details & 46 images.
$279,000 $198 per sq.ft. Village of North Bennington in Town of Bennington VT Home »
Price Change! Reduced by $20,000 down 7% on June 6th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1408 | Acres: 0.25
Listed on Friday May 8, 2026
Description: Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout. Enjoy the convenience of first floor laundry, a beautiful front porch perfect for morning coffee or evening cocktails, and a private backyard ideal for entertaining, gardening, or simply relaxing while still enjoying the benefits of in town living. Owned and cherished by the same family for many years, this property has been exceptionally cared for and offers too many updates to count. From the inviting turquoise staircase to the unique character and charm found throughout the home, every corner tells a story. Take a stroll to local coffee shops, dinner spots, and community events, or enjoy hearing music drifting from the nearby Park-McCullough concert series on summer evenings. This home offers the perfect balance of neighborhood living, privacy, and small town charm. A true North Bennington gem full of warmth, character, and uniqueness this is a must see property. Call today for your private showing. This one will not last long! See Listing Details & 33 images. Includes a Virtual Tour
$299,000 $163 per sq.ft. Bennington VT Home »
Price Change! Reduced by $26,000 down 9% on July 14th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1829 | Acres: 0.93
Listed on Wednesday Jun 17, 2026
Description: Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you'll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026. What truly sets this property apart is its incredible versatility. The bonus space presents endless possibilities for a home based business, professional office, hobby space, expanded living area, or potential in-law accommodations. Whether you're looking for room to grow, work from home, or create a space tailored to your lifestyle, this home offers the flexibility to make it happen. The generous lot and rear garage access provide additional opportunities for future improvements. Buyers may appreciate the potential to enhance accessibility and functionality with a redesigned driveway configuration, such as a circular drive, while maximizing the usefulness of the garage space and expansive yard. Enjoy the convenience of being just minutes from downtown Bennington's shops, restaurants, coffee houses, and local attractions, while still enjoying the privacy of a large lot. With easy access to area hiking trails, ski resorts, and major routes to Boston and New York, this property combines location, character, and opportunity in one exceptional package. See Listing Details & 38 images.
Under Contract
$309,900 $163 per sq.ft. Bennington VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1900 | Acres: 0.31Listed on Tuesday Apr 21, 2026
Description: Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a must see location. See Listing Details & 38 images.
$319,900 $213 per sq.ft. Village of North Bennington in Town of Bennington VT Home »
Price Change! Reduced by $20,000 down 6% on July 10th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1500 | Acres: 0.53
Listed on Monday Apr 20, 2026
Description: 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. See Listing Details & 43 images.
Under Contract
$335,000 $237 per sq.ft. Bennington VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1414 | Acres: 0.28Listed on Tuesday Jul 21, 2026
Description: Welcome home to this meticulously maintained 3 bedroom, 1.5 bath ranch, perfectly nestled in a highly desirable neighborhood. Offering over 1,400 square feet of single level living space, this home combines classic charm, everyday comfort, and an unbeatable location. Rich hardwood floors flow throughout most of the home creating a warm and inviting atmosphere from the moment you step inside. The spacious layout offers comfortable living areas filled with natural light, generous-sized bedrooms, and a floor plan designed for effortless everyday living and easy entertaining. A charming breezeway connects the home to the attached one-car garage, providing a practical transition space that's perfect in every season while adding timeless New England character. Outside, the yard offers room to garden, play, or simply relax and enjoy the peaceful surroundings. Location is everything, and this home delivers. Tucked into an established neighborhood known for its welcoming feel, you'll be just minutes from downtown, where you can enjoy local shops, restaurants, community events, and everyday conveniences. Nearby walking trails offer the perfect setting for morning jogs, leisurely evening strolls, or weekends spent enjoying the outdoors. Whether you're buying your first home, looking to simplify with one-level living, or searching for a property in a neighborhood you'll love for years to come, this home offers the perfect blend of comfort, convenience, and lasting appeal. Don't miss your opportunity to make this exceptional ranch your own! See Listing Details & 38 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.
Under Contract New Listing!
$365,000 $230 per sq.ft. Village of North Bennington in Town of Bennington VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1588 | Acres: 0.14Listed on Friday Jul 24, 2026
Description: 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. See Listing Details & 31 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.
$429,000 $352 per sq.ft. Bennington NH Home »
Price Change! Reduced by $10,000 down 2% on July 23rd 2026
3 Beds | 2 Baths | Total Sq. Ft. 1219 | Acres: 0.54
Listed on Saturday Mar 21, 2026
Description: 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. See Listing Details & 18 images.
Under Contract
$439,000 $220 per sq.ft. Village of North Bennington in Town of Bennington VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 2389 | Acres: 1.16Listed on Thursday Jul 2, 2026
Description: 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. See Listing Details & 37 images.
