Bennington Homes under $500,000

Beautifully renovated inside and out, this 3-bedroom, 2-bath Ranch offers 1,788 square feet of comfortable single-level living in a highly coveted Bennington location. Tucked into an established neighborhood on the outskirts of town, the property feels private and peaceful while remaining just minutes from major shopping, services, and everyday conveniences. Thoughtfully remodeled with a gorgeous new kitchen featuring KraftMaid cabinetry, stainless steel appliances, generous counter space, and a contrasting center island. New vinyl plank flooring, additional overhead lighting, and larger windows create a bright, fresh feel throughout. The spacious living room is anchored by a dramatic feature-wall fireplace with a new mantel and woodstove insert, creating a warm focal point for the home. In addition to three bedrooms and two full baths, the main level includes a dedicated office and separate laundry room, making the floor plan especially practical for today’s lifestyle. The primary bedroom is generously sized and includes a private bath and walk-in closet. Outside, mature trees and lush perennial gardens surround the home, while the rear patio and side deck offer quiet places to relax and enjoy the wooded setting. An attached two-car garage with a new automatic opener adds everyday convenience, and the full basement has been professionally improved by Northern Basement Systems to provide a clean, dry space with excellent storage potential. Other improvements include a newer Buderus boiler, a 200-amp electrical panel, heat pump mini splits for energy-efficient heating and cooling, and leased solar panels. A beautifully reimagined home, a highly functional one-level layout, and a location that offers both neighborhood living and quick access to town make 78 Astrachan Drive a true standout.

78 Astrachan Dr, Bennington

$145,000

2 Beds ⋅ 2 Baths ⋅ 5112929 MLS

Enjoy the convenience and value of this two bedroom, 1.5 bathroom end-unit condo. Offering easy first-floor living, this home is a great option for first-time buyers, downsizers, or anyone looking for a comfortable, manageable place to call home. The practical layout includes two bedrooms, providing flexibility for guests, a home office, or additional living space. Discover the simplicity of condo living and the ease of having everything on one level. Ideally located just minutes from downtown shops and restaurants, while still within walking distance of peaceful hiking and nature trails. Whether you're looking to simplify your lifestyle or find an affordable path to homeownership, this is an opportunity worth exploring.

432 South St Unit B3, 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

$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

$329,000

3 Beds ⋅ 2 Baths ⋅ 5111698 MLS

Charming Bennington home with classic character, hardwood floors, and a bright enclosed sun porch! This inviting property offers a comfortable blend of traditional charm and everyday functionality, with spacious living areas. The generous living room provides plenty of room for comfortable seating and entertaining, while the sun porch offers a wonderful additional space to enjoy the changing seasons, morning coffee, reading, or simply relaxing surrounded by natural light. The home offers a warm, practical layout with attractive wood flooring and ample windows throughout. Outside, the property sits above the street with stone retaining walls, creating a private and inviting setting. The attached garage provides convenient parking and storage, with additional driveway space. Located in Bennington, this home provides easy access to the area's shops, restaurants, services, schools, and outdoor recreation. Whether you're looking for a home with classic Vermont character, 110 Coulter St offers a great opportunity to make a property your own.

110 Coulter St, 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

$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

$219,000

2 Beds ⋅ 1 Baths ⋅ 5111442 MLS

As the old saying goes... LOCATION, LOCATION, LOCATION! Situated on a large corner lot in the desirable village of North Bennington, this one level home is brimming with potential. There is plenty of space inside and several rooms that can be configured to fit your needs. The great room has a vaulted ceiling and a slider to an enclosed porch that overlooks a private backyard. The kitchen with island has brand new flooring. The spacious primary bedroom has a big closet and connects to a room that could be an office or study with a walk-in closet. A metal roof and vinyl siding are both a plus. The property itself extends right to the banks of Paran Creek with direct access to the water. It's the perfect spot for a picnic table as you listen to the soothing sounds of nature. Set just 0.6 miles from Lake Paran, this location puts swimming, kayaking, fishing, walking trails, and events right at your fingertips. The village itself is part of the appeal. Stroll to local shops, eateries, and community gathering places. Whether you're looking for an incredible investment or a wonderful place to call home, this property is truly a catch.

2 North St, Bennington

$249,500

3 Beds ⋅ 2 Baths ⋅ 5111369 MLS

Conveniently located in the heart of Bennington, this charming 3-bedroom, 2-bath Cape offers a wonderful combination of comfort, privacy, and walkability. Set along a newly paved road with sidewalks, you can leave the car at home and head downtown for a meal or enjoy some of Bennington’s favorite local events. Easy highway access is nearby, yet the home feels surprisingly tucked away with its spacious yard and privacy fencing. Inside, 1,271 square feet of finished living space offers a comfortable, open feel, with the living room flowing naturally into the dining and kitchen areas, perfect for everyday living and gathering with friends and family. The well-appointed kitchen features abundant wood cabinetry, a double sink, newer black appliances. Newly refinished hardwood floors add character throughout the main living areas. The generously sized main-floor primary bedroom features an ensuite full bath with wainscoting. while two additional bedrooms are upstairs. A second full bath off the living room includes full-size laundry, adding to the ease of main-floor living. Both baths have been updated with tile floors, pedestal sinks, and fiberglass tub/shower surrounds. Two additional bedrooms upstairs, one features a walk-in closet. Recent improvements include a hybrid heat-pump water heater and 200 AMP electrical panel, meaningful updates to the home’s major systems. Outside, the fully fenced side yard is a true highlight, with plenty of room for gardens, play, pets, entertaining, or simply enjoying your own private outdoor space, complete with apple tree. The large .41 acre lot includes more land between garage and stone wall to meet your expanding needs. The garage/barn accommodates one vehicle with additional storage or hobby space. Ample driveway parking allows for multiple cars. An inviting and affordable opportunity to put down roots, with room to enjoy both home and yard while keeping downtown Bennington close at hand.

230 Beech St, Bennington

$449,900

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

$165,000

2 Beds ⋅ 1 Baths ⋅ 5111064 MLS

Affordable homeownership awaits at 128 Burgess Road in Bennington! This compact 2-bedroom, 1-bath home offers approximately 840 square feet of living space with a practical layout and low utility costs. Several recent exterior improvements include brand-new siding, new rear entry stairs and a new electrical meter board in Spring 2026. The home also features vinyl replacement windows, including one newly installed side window. The main level includes the kitchen, dining area, living room and first-floor laundry. Upstairs are two bedrooms with hardwood flooring and a full bathroom with tile flooring that includes a shower/tub combo with a tile surround. Outside, the manageable 0.08-acre lot includes a fully fenced yard that slopes gently and is easy to mow. Exterior basement access provides additional utility and storage space. The property is accessed via deeded right-of-way driveway and parking, tucked off the street for added privacy. Conveniently located near downtown Bennington, you can walk to parades, festivals, and restaurants. An attainable opportunity for an investor or owner-occupant who wants to add their own finishing touches.

128 Burgess Rd, 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

Bennington Homes under $500,000

Newest Bennington Homes under $500,000