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Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes laundry, creating true one-floor convenience. Main living spaces are warm, bright, and inviting, with hardwood floors, bay windows, abundant natural light, and a distinctive two-sided brick fireplace with gas insert anchoring both the living and dining rooms. Built-in shelving adds character and function, while the easy flow between rooms makes the home comfortable for everyday living and welcoming for guests. The galley kitchen sits at the center of the home, with space for a breakfast table and direct access to the large deck. Big picture windows frame the surrounding greenery and mountain view, bringing the setting beautifully indoors. The finished lower level adds substantial flexibility, featuring a spacious rec room with wet bar, pool table, and gas stove. It's an ideal space to enjoy game nights, hobbies, movie watching, or relaxed entertaining. This level also includes a half bath, updated utilities, and a large storage room. With both an attached 2-car garage and a detached 2-car garage, there is outstanding room for vehicles, storage, equipment, workshop space, or recreational gear. Outside, the property feels private and established, with open lawn, mature landscaping, garden space, and room to enjoy the quiet surroundings. Built in 1987 and offered by its original owner, this property presents a special opportunity for buyers seeking space, privacy, mountain views, main-level living, and exceptional utility in one complete package.

2 Beds ⋅ 3 Baths ⋅ 5094280 MLS

Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes laundry, creating true one-floor convenience. Main living spaces are warm, bright, and inviting, with hardwood floors, bay windows, abundant natural light, and a distinctive two-sided brick fireplace with gas insert anchoring both the living and dining rooms. Built-in shelving adds character and function, while the easy flow between rooms makes the home comfortable for everyday living and welcoming for guests. The galley kitchen sits at the center of the home, with space for a breakfast table and direct access to the large deck. Big picture windows frame the surrounding greenery and mountain view, bringing the setting beautifully indoors. The finished lower level adds substantial flexibility, featuring a spacious rec room with wet bar, pool table, and gas stove. It's an ideal space to enjoy game nights, hobbies, movie watching, or relaxed entertaining. This level also includes a half bath, updated utilities, and a large storage room. With both an attached 2-car garage and a detached 2-car garage, there is outstanding room for vehicles, storage, equipment, workshop space, or recreational gear. Outside, the property feels private and established, with open lawn, mature landscaping, garden space, and room to enjoy the quiet surroundings. Built in 1987 and offered by its original owner, this property presents a special opportunity for buyers seeking space, privacy, mountain views, main-level living, and exceptional utility in one complete package.

193 Finley Dr, Bennington

$595,000

Step into this beautifully built post-and-beam house by well-known local builders Blue Heron Construction. Built in 1989 in classic Blue Heron style with an earthy exterior and a warm, glowing, golden interior, the house retains its original features, just waiting to be embraced by its next occupant. The location of the home couldn’t be better, nestled on 9+ secluded acres in North Bennington. Create your own walking trails or explore the lovely rural roads in the neighborhood. Practical and cultural amenities are just minutes away by foot, car, bike or snowshoes. Entering the home through the brick-floored mudroom, you arrive in a large, open living/kitchen area with high ceilings, exposed beams and a cozy wood stove. Surrounding this inviting space, you will find a master bedroom with bathroom annex, a dining room, an office/library, and a second ground floor bedroom. Up the bespoke wooden staircase are 3 more rooms with bathroom and separate entrance, perfect for extended family or multi-generational living. Back downstairs, you will be stunned by the size of the huge, heated workshop, with plenty of room for a woodworker, potter, jeweler, painter or sculptor to work their magic. Above this workspace is a large second-floor studio apartment with private entrance and a spacious screened porch. A substantial barn/garage with a loft area provides even more space for vehicles, equipment, storage, or future expansion. If you’re looking for multi-generational living, short or long term rental opportunities, or room for home-based business, this house could be perfect for you. The property is accessible from College Road but also has approximately 100 feet of road frontage on Matteson Road which could present future building opportunities, subject to local approvals. This house is a spacious North Bennington jewel. Move in right away, or take your time with a retrofit, as this house offers the versatility and flexibility to be whatever you want it to be.

5 Beds ⋅ 3 Baths ⋅ 5093651 MLS

Step into this beautifully built post-and-beam house by well-known local builders Blue Heron Construction. Built in 1989 in classic Blue Heron style with an earthy exterior and a warm, glowing, golden interior, the house retains its original features, just waiting to be embraced by its next occupant. The location of the home couldn’t be better, nestled on 9+ secluded acres in North Bennington. Create your own walking trails or explore the lovely rural roads in the neighborhood. Practical and cultural amenities are just minutes away by foot, car, bike or snowshoes. Entering the home through the brick-floored mudroom, you arrive in a large, open living/kitchen area with high ceilings, exposed beams and a cozy wood stove. Surrounding this inviting space, you will find a master bedroom with bathroom annex, a dining room, an office/library, and a second ground floor bedroom. Up the bespoke wooden staircase are 3 more rooms with bathroom and separate entrance, perfect for extended family or multi-generational living. Back downstairs, you will be stunned by the size of the huge, heated workshop, with plenty of room for a woodworker, potter, jeweler, painter or sculptor to work their magic. Above this workspace is a large second-floor studio apartment with private entrance and a spacious screened porch. A substantial barn/garage with a loft area provides even more space for vehicles, equipment, storage, or future expansion. If you’re looking for multi-generational living, short or long term rental opportunities, or room for home-based business, this house could be perfect for you. The property is accessible from College Road but also has approximately 100 feet of road frontage on Matteson Road which could present future building opportunities, subject to local approvals. This house is a spacious North Bennington jewel. Move in right away, or take your time with a retrofit, as this house offers the versatility and flexibility to be whatever you want it to be.

81 Honeysuckle Ln, Bennington

$69,900

Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington and its vibrant Main Street, which offers shops, restaurants, and year-round community events. It is also conveniently located just 30 minutes from Manchester, VT, and Williamstown, MA. Additionally, it is within approximately 45 minutes of several ski resorts, including Mount Snow, Stratton Mountain, Bromley Mountain, and Jiminy Peak.

5092066 MLS

Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington and its vibrant Main Street, which offers shops, restaurants, and year-round community events. It is also conveniently located just 30 minutes from Manchester, VT, and Williamstown, MA. Additionally, it is within approximately 45 minutes of several ski resorts, including Mount Snow, Stratton Mountain, Bromley Mountain, and Jiminy Peak.

Brambley Ln, Bennington

$350,000

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. 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.

2 Beds ⋅ 2 Baths ⋅ 5090266 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. 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.

524 Jennings Brook Dr, Bennington

$179,000

Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to own a large condo unit with the space and versatility of a single-family home, paired with the ease of low-maintenance living. The main living level boasts an open-concept kitchen, dining, and living area ideal for entertaining, along with a half bath with laundry, a spacious bedroom with en-suite bath, and an additional bedroom. The third floor serves as a stunning private retreat featuring a second primary en-suite, skylights, and flexible bonus space perfect for a home office, library, exercise area, or cozy reading nook. Just minutes from downtown Bennington’s shops, restaurants, recreation, and cultural attractions, this move-in ready condo offers low-maintenance living without sacrificing space or style. A truly unique offering in a highly convenient location!

3 Beds ⋅ 3 Baths ⋅ 5089968 MLS

Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to own a large condo unit with the space and versatility of a single-family home, paired with the ease of low-maintenance living. The main living level boasts an open-concept kitchen, dining, and living area ideal for entertaining, along with a half bath with laundry, a spacious bedroom with en-suite bath, and an additional bedroom. The third floor serves as a stunning private retreat featuring a second primary en-suite, skylights, and flexible bonus space perfect for a home office, library, exercise area, or cozy reading nook. Just minutes from downtown Bennington’s shops, restaurants, recreation, and cultural attractions, this move-in ready condo offers low-maintenance living without sacrificing space or style. A truly unique offering in a highly convenient location!

432 South St Unit D2, Bennington

$675,000

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.

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

103 Jennings Brook Dr Unit 103, Bennington

$250,000

Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as a home office, adding flexible living space to fit today’s lifestyle. The main level includes a first-floor bedroom and ¾ bath, along with a sunroom perfect for relaxing and enjoying the surroundings. Upstairs are two additional bedrooms, including the primary suite, plus a large storage area. This home does need a little TLC, including some carpet and paint updates, but offers tremendous potential and great bones. Additional features include an attached one-car garage and a large back deck for outdoor enjoyment. Conveniently located within walking distance to downtown, the hospital, and the monument, this condo is a fantastic opportunity to make it your own.

3 Beds ⋅ 2 Baths ⋅ 5088382 MLS

Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as a home office, adding flexible living space to fit today’s lifestyle. The main level includes a first-floor bedroom and ¾ bath, along with a sunroom perfect for relaxing and enjoying the surroundings. Upstairs are two additional bedrooms, including the primary suite, plus a large storage area. This home does need a little TLC, including some carpet and paint updates, but offers tremendous potential and great bones. Additional features include an attached one-car garage and a large back deck for outdoor enjoyment. Conveniently located within walking distance to downtown, the hospital, and the monument, this condo is a fantastic opportunity to make it your own.

103 Jennings Brook Dr Unit 103, Bennington

$550,000

Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home. Situated on over 17 acres, this property offers not one but two barns, established fenced pastures, and the kind of setting that feels like a Vermont dream. Listen to the breeze move through the grass, watch the leaves change color in the fall, and enjoy the privacy and beauty that surround you. Inside, you’ll find five bedrooms and two full bathrooms, with space that invites family dinners, holiday gatherings, and everyday moments that make a house feel special. The usable basement offers excellent storage, workshop potential, tool space, or room for tack and farm equipment. Whether you have horses, farm animals, or simply want the charm and comfort of country living, this property offers the Vermont lifestyle so many people dream about. This is more than a house it’s the feeling of finally coming home.

5 Beds ⋅ 2 Baths ⋅ 5088350 MLS

Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home. Situated on over 17 acres, this property offers not one but two barns, established fenced pastures, and the kind of setting that feels like a Vermont dream. Listen to the breeze move through the grass, watch the leaves change color in the fall, and enjoy the privacy and beauty that surround you. Inside, you’ll find five bedrooms and two full bathrooms, with space that invites family dinners, holiday gatherings, and everyday moments that make a house feel special. The usable basement offers excellent storage, workshop potential, tool space, or room for tack and farm equipment. Whether you have horses, farm animals, or simply want the charm and comfort of country living, this property offers the Vermont lifestyle so many people dream about. This is more than a house it’s the feeling of finally coming home.

971 S Stream Rd, Bennington

$475,000

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.

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

$249,000

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!

3 Beds ⋅ 2 Baths ⋅ 5087836 MLS

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!

8 West St, Bennington

$265,000

BACK ON MARKET! Enjoy low-maintenance living at The Birches of Bennington, ideally located just minutes from Crotched Mountain for skiing, snowboarding, hiking, and year-round outdoor recreation. This spacious 2-bedroom, 2.5-bath condo features a bright and inviting living room with a cozy wood-burning fireplace, perfect for relaxing after a day on the slopes. The open-concept kitchen and dining area offers abundant cabinet and counter space, appliances, a breakfast bar, and sliding doors leading to the back deck for easy indoor-outdoor living. Upstairs, you’ll find two generously sized bedrooms, each with its own ensuite bath. The primary suite includes two oversized double closets and a private balcony with views of the mountain slopes. The unfinished lower level provides excellent potential for a recreation room, home office, gym, or additional living space. Conveniently located just 90 minutes from Boston and about an hour from Manchester and the Seacoast region, this is the perfect opportunity to enjoy four-season living in a sought-after mountain community. Don’t miss your chance to live where you play! SELLER FINANCING AVAILABLE

2 Beds ⋅ 3 Baths ⋅ 5087755 MLS

BACK ON MARKET! Enjoy low-maintenance living at The Birches of Bennington, ideally located just minutes from Crotched Mountain for skiing, snowboarding, hiking, and year-round outdoor recreation. This spacious 2-bedroom, 2.5-bath condo features a bright and inviting living room with a cozy wood-burning fireplace, perfect for relaxing after a day on the slopes. The open-concept kitchen and dining area offers abundant cabinet and counter space, appliances, a breakfast bar, and sliding doors leading to the back deck for easy indoor-outdoor living. Upstairs, you’ll find two generously sized bedrooms, each with its own ensuite bath. The primary suite includes two oversized double closets and a private balcony with views of the mountain slopes. The unfinished lower level provides excellent potential for a recreation room, home office, gym, or additional living space. Conveniently located just 90 minutes from Boston and about an hour from Manchester and the Seacoast region, this is the perfect opportunity to enjoy four-season living in a sought-after mountain community. Don’t miss your chance to live where you play! SELLER FINANCING AVAILABLE

69 Birch Glen Dr Unit 12, Bennington

$180,000

Unlock the potential of this spectacular 58.1 +/- acre woodland property in historic Bennington. The groundwork for your future home or getaway is already laid with a State-approved wastewater permit in place for a three-bedroom single-family residence, allowing you the flexibility to design your build. Further simplifying your plans, the property offers the rare advantage of connecting to the municipal water supply at the road. Essential utilities are right at your fingertips, with power readily available along the town-maintained, plowed Chapel Road near utility pole #25, and Xfinity providing high-speed cable internet, TV, and phone services. An existing roughed-in driveway provides a solid starting point for accessing the expansive acreage. Backing directly up to the 926-acre state-owned Bald Mountain recreational area, this woodland is an outdoor enthusiast's dream. The diverse landscape features approximately 30 acres of manageable hardwood timber and 28 acres of softwoods on the higher ground. Beech and red oak provide excellent wildlife habitat, while existing woods roads offer private trails for cross-country skiing, hiking, and ATVing with distant views of the Green Mountain National Forest. The land benefits from reduced taxes by being enrolled in Vermont's Current Use program, with six acres thoughtfully excluded to accommodate your development. Conveniently located just minutes from downtown Bennington, you have quick access to local dining, the Bennington Museum, and the historic Bennington Battle Monument. Seize the rare opportunity to craft your perfect Vermont lifestyle on this expansive woodland canvas!

5087361 MLS

Unlock the potential of this spectacular 58.1 +/- acre woodland property in historic Bennington. The groundwork for your future home or getaway is already laid with a State-approved wastewater permit in place for a three-bedroom single-family residence, allowing you the flexibility to design your build. Further simplifying your plans, the property offers the rare advantage of connecting to the municipal water supply at the road. Essential utilities are right at your fingertips, with power readily available along the town-maintained, plowed Chapel Road near utility pole #25, and Xfinity providing high-speed cable internet, TV, and phone services. An existing roughed-in driveway provides a solid starting point for accessing the expansive acreage. Backing directly up to the 926-acre state-owned Bald Mountain recreational area, this woodland is an outdoor enthusiast's dream. The diverse landscape features approximately 30 acres of manageable hardwood timber and 28 acres of softwoods on the higher ground. Beech and red oak provide excellent wildlife habitat, while existing woods roads offer private trails for cross-country skiing, hiking, and ATVing with distant views of the Green Mountain National Forest. The land benefits from reduced taxes by being enrolled in Vermont's Current Use program, with six acres thoughtfully excluded to accommodate your development. Conveniently located just minutes from downtown Bennington, you have quick access to local dining, the Bennington Museum, and the historic Bennington Battle Monument. Seize the rare opportunity to craft your perfect Vermont lifestyle on this expansive woodland canvas!

1073 Chapel Rd, Bennington

$475,000

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.

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

$209,900

Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a large garage with an attached storage shed and ample paved parking.

2 Beds ⋅ 1 Baths ⋅ 5086144 MLS

Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a large garage with an attached storage shed and ample paved parking.

1083 Main St, Bennington

$53,000

Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home. Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process. Located on a publicly maintained road, this property combines convenience with a peaceful, well kept neighborhood setting. Enjoy close proximity to local amenities including shopping, dining, and the hospital, while also benefiting from easy access to major routes connecting you to Albany, Boston, and New York City. Outdoor enthusiasts will appreciate nearby walking and biking trails, along with year round Vermont recreation including hiking, skiing, and exploring the natural beauty of the area. Set within the North Bennington area and served by the local elementary school, this lot offers the ideal blend of location, lifestyle, and readiness. A prime opportunity to bring your vision to life in a scenic Vermont setting. Walkway Disclosure: An established walkway currently crosses the property; however, the property is not being conveyed with any obligation for the new owner to maintain or continue the walkway. Upon transfer, the property will become the private property of the new owner, and the walkway will no longer be maintained or used as a throughway. The College will post signage indicating that the property is private and that through access is no longer permitted.

5086024 MLS

Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home. Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process. Located on a publicly maintained road, this property combines convenience with a peaceful, well kept neighborhood setting. Enjoy close proximity to local amenities including shopping, dining, and the hospital, while also benefiting from easy access to major routes connecting you to Albany, Boston, and New York City. Outdoor enthusiasts will appreciate nearby walking and biking trails, along with year round Vermont recreation including hiking, skiing, and exploring the natural beauty of the area. Set within the North Bennington area and served by the local elementary school, this lot offers the ideal blend of location, lifestyle, and readiness. A prime opportunity to bring your vision to life in a scenic Vermont setting. Walkway Disclosure: An established walkway currently crosses the property; however, the property is not being conveyed with any obligation for the new owner to maintain or continue the walkway. Upon transfer, the property will become the private property of the new owner, and the walkway will no longer be maintained or used as a throughway. The College will post signage indicating that the property is private and that through access is no longer permitted.

29 Asas Way, Bennington

$53,000

Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience. Public water and sewer are available, making the lot ready for development and easy to build on. Ideally located just minutes from downtown North Bennington, you’ll enjoy close proximity to local shops, dining, and everyday amenities, along with quick access to major routes for commuting to Albany, New York City, Boston, and beyond. Situated within a desirable school choice embrace the Vermont lifestyle with nearby walking trails, scenic outdoor spaces, and a peaceful country setting, all while being conveniently close to local amenities and the area hospital. This property offers the perfect balance of quiet surroundings and accessibilities, set in a welcoming neighborhood that captures the charm and character Vermont is known for. A prime, build ready parcel bring your vision and get started. Walkway Disclosure: An established walkway currently crosses the property; however, the property is not being conveyed with any obligation for the new owner to maintain or continue the walkway. Upon transfer, the property will become the private property of the new owner, and the walkway will no longer be maintained or used as a throughway. The College will post signage indicating that the property is private and that through access is no longer permitted.

5086022 MLS

Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience. Public water and sewer are available, making the lot ready for development and easy to build on. Ideally located just minutes from downtown North Bennington, you’ll enjoy close proximity to local shops, dining, and everyday amenities, along with quick access to major routes for commuting to Albany, New York City, Boston, and beyond. Situated within a desirable school choice embrace the Vermont lifestyle with nearby walking trails, scenic outdoor spaces, and a peaceful country setting, all while being conveniently close to local amenities and the area hospital. This property offers the perfect balance of quiet surroundings and accessibilities, set in a welcoming neighborhood that captures the charm and character Vermont is known for. A prime, build ready parcel bring your vision and get started. Walkway Disclosure: An established walkway currently crosses the property; however, the property is not being conveyed with any obligation for the new owner to maintain or continue the walkway. Upon transfer, the property will become the private property of the new owner, and the walkway will no longer be maintained or used as a throughway. The College will post signage indicating that the property is private and that through access is no longer permitted.

24 Asas Way, Bennington

$179,000

Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with rental income from the other, or continue using the property as an investment. Appears well suited for FHA, VA, USDA, and conventional financing. Conveniently located near shopping, dining, schools, medical facilities, and other everyday amenities in downtown Bennington. Bennington continues to benefit from ongoing investment and redevelopment throughout the downtown area, adding to the appeal of this location.

5085882 MLS

Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with rental income from the other, or continue using the property as an investment. Appears well suited for FHA, VA, USDA, and conventional financing. Conveniently located near shopping, dining, schools, medical facilities, and other everyday amenities in downtown Bennington. Bennington continues to benefit from ongoing investment and redevelopment throughout the downtown area, adding to the appeal of this location.

340 Pleasant St, Bennington

$199,900

2-Unit Multi-Family with Professional-Grade Workshop! Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast, or premium climate-controlled storage rental, this workspace provides an incredible environment for any business or hobby. Located directly above the shop are two freshly painted 1BR/1BA apartments with a remarkable decade-long track record of consistent tenancy. The property currently generates a steady $1,850 in monthly income. The property provides plenty of off-street parking suitable for automobiles or equipment, plus a 12' x 20' shed for additional storage. Unmatched versatility and a turnkey footprint.

5085771 MLS

2-Unit Multi-Family with Professional-Grade Workshop! Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast, or premium climate-controlled storage rental, this workspace provides an incredible environment for any business or hobby. Located directly above the shop are two freshly painted 1BR/1BA apartments with a remarkable decade-long track record of consistent tenancy. The property currently generates a steady $1,850 in monthly income. The property provides plenty of off-street parking suitable for automobiles or equipment, plus a 12' x 20' shed for additional storage. Unmatched versatility and a turnkey footprint.

2 Hamlin Ave, Bennington

$135,000

This exceptional piece of property offers exciting development potential with blueprints for storage units approved by the town - saving you time and hassle. The cleared site is ready for your vision and offers flexibility for various uses. Whether you're looking to build a single-family residence, multi-unit development (with town approval), or bring the approved storage unit project to life, this land is a rare find. Located in a desirable area with easy access, the property is being transferred in "Current Use" tax status, offering additional savings. Don't miss your chance to unlock the potential of this diamond in the rough - opportunities like this don't come around often!

5085591 MLS

This exceptional piece of property offers exciting development potential with blueprints for storage units approved by the town - saving you time and hassle. The cleared site is ready for your vision and offers flexibility for various uses. Whether you're looking to build a single-family residence, multi-unit development (with town approval), or bring the approved storage unit project to life, this land is a rare find. Located in a desirable area with easy access, the property is being transferred in "Current Use" tax status, offering additional savings. Don't miss your chance to unlock the potential of this diamond in the rough - opportunities like this don't come around often!

M16-L02 Us Highway 202, Bennington

$319,900

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.

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

$255,000

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.

3 Beds ⋅ 1 Baths ⋅ 5083898 MLS

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.

951 Gage St, Bennington

$199,900

Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an excellent opportunity to add your own finishing touches and build equity in a highly desirable location. Enjoy true village living with walkable access to cafés, restaurants, and trails, plus close proximity to Lake Paran and the Park-McCullough House. School choice at the elementary level adds flexibility. Just minutes to downtown Bennington for additional shopping, dining, and amenities, with easy access to multiple ski destinations. Conveniently located approximately one hour to Albany International Airport and about three hours to NYC and Boston. A rare opportunity to own in one of North Bennington’s most sought-after settings.

4 Beds ⋅ 1 Baths ⋅ 5083528 MLS

Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an excellent opportunity to add your own finishing touches and build equity in a highly desirable location. Enjoy true village living with walkable access to cafés, restaurants, and trails, plus close proximity to Lake Paran and the Park-McCullough House. School choice at the elementary level adds flexibility. Just minutes to downtown Bennington for additional shopping, dining, and amenities, with easy access to multiple ski destinations. Conveniently located approximately one hour to Albany International Airport and about three hours to NYC and Boston. A rare opportunity to own in one of North Bennington’s most sought-after settings.

20 Sage St, Bennington

$265,000

Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a wide range of commercial uses including retail, food and beverage, office, studio, and personal services. The second-floor apartment, renovated by a prior owner approximately 10 years ago, provides comfortable living space ideal for an owner-occupant or steady rental income. The first floor and basement, formerly home to a long-standing florist shop, now offer a bright, open layout with the removal of the walk-in cooler, making the space feel larger and more adaptable than ever. Recent updates include fresh paint, new flooring, LED lighting, and a convenient half bath. For investors or those seeking a full residential conversion, the layout and separate entrances offer a clear opportunity to reconfigure the first floor into a second living unit, establishing a true duplex. The basement adds valuable storage with built-in shelving, while the walk-up attic offers additional storage or future expansion potential. Additional features include separate electric meters, shared boiler and oil tank (both replaced in 2020), vinyl siding and windows, architectural shingle roof, town water and sewer, and high-speed internet. Off-street parking for both units enhances functionality. Situated along one of North Street’s most traveled corridors, the property benefits from excellent visibility, signage potential, and proximity to established neighbors like Blue Benn Diner, Wassick’s Tire Service, and the Vermont Veterans Home. Whether you’re looking for an investment property, live/work setup, or a redevelopment opportunity, this flexible property is ready to meet your vision.

5081898 MLS

Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a wide range of commercial uses including retail, food and beverage, office, studio, and personal services. The second-floor apartment, renovated by a prior owner approximately 10 years ago, provides comfortable living space ideal for an owner-occupant or steady rental income. The first floor and basement, formerly home to a long-standing florist shop, now offer a bright, open layout with the removal of the walk-in cooler, making the space feel larger and more adaptable than ever. Recent updates include fresh paint, new flooring, LED lighting, and a convenient half bath. For investors or those seeking a full residential conversion, the layout and separate entrances offer a clear opportunity to reconfigure the first floor into a second living unit, establishing a true duplex. The basement adds valuable storage with built-in shelving, while the walk-up attic offers additional storage or future expansion potential. Additional features include separate electric meters, shared boiler and oil tank (both replaced in 2020), vinyl siding and windows, architectural shingle roof, town water and sewer, and high-speed internet. Off-street parking for both units enhances functionality. Situated along one of North Street’s most traveled corridors, the property benefits from excellent visibility, signage potential, and proximity to established neighbors like Blue Benn Diner, Wassick’s Tire Service, and the Vermont Veterans Home. Whether you’re looking for an investment property, live/work setup, or a redevelopment opportunity, this flexible property is ready to meet your vision.

318 North St, Bennington

$997,000

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

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

$269,000

Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With a level lot just over half-acre, off-street parking, and 1 car garage/barn with additional storage, plus a prime location near downtown shops and restaurants, this is an ideal opportunity for both investors and owner-occupants!

5081521 MLS

Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With a level lot just over half-acre, off-street parking, and 1 car garage/barn with additional storage, plus a prime location near downtown shops and restaurants, this is an ideal opportunity for both investors and owner-occupants!

124 S Branch St, Bennington

$259,000

Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car garage. Ideally located just minutes from downtown shops, restaurants, and nightlife. A fantastic opportunity for owner-occupants or investors alike!

5081518 MLS

Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car garage. Ideally located just minutes from downtown shops, restaurants, and nightlife. A fantastic opportunity for owner-occupants or investors alike!

116-118 S Branch St, Bennington

$198,000

Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level Class IV gravel frontage (gravel portion is not plowed or maintained by the town – 400+/- ft). A gate is currently in place, but the town will remove or relocate upon request. Essential utilities are highly accessible: town water runs along the frontage with confirmed adequate pressure for development, while power and high-speed cable internet sit just 250 feet west. State mapping indicates favorable conditions for a wastewater system and a previous purchaser performed soils test indicating a 6-bedroom residential mound system but opted not to purchase; they wanted a home much closer to the road, where the State maps indicate a small wetland. This should be easily avoidable. Experience the best of both worlds - a secluded, off-the-beaten-path atmosphere with immediate access to the Route 7 corridor. You are just minutes from historic downtown Bennington’s shops, dining, and the iconic Bennington Battle Monument. For outdoor lovers, enjoy proximity to the Green Mountain National Forest and premier skiing at Mount Snow and Stratton. Whether dreaming of an expansive recreational haven or a brilliant investment opportunity, this versatile acreage is ready for your vision.

5081020 MLS

Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level Class IV gravel frontage (gravel portion is not plowed or maintained by the town – 400+/- ft). A gate is currently in place, but the town will remove or relocate upon request. Essential utilities are highly accessible: town water runs along the frontage with confirmed adequate pressure for development, while power and high-speed cable internet sit just 250 feet west. State mapping indicates favorable conditions for a wastewater system and a previous purchaser performed soils test indicating a 6-bedroom residential mound system but opted not to purchase; they wanted a home much closer to the road, where the State maps indicate a small wetland. This should be easily avoidable. Experience the best of both worlds - a secluded, off-the-beaten-path atmosphere with immediate access to the Route 7 corridor. You are just minutes from historic downtown Bennington’s shops, dining, and the iconic Bennington Battle Monument. For outdoor lovers, enjoy proximity to the Green Mountain National Forest and premier skiing at Mount Snow and Stratton. Whether dreaming of an expansive recreational haven or a brilliant investment opportunity, this versatile acreage is ready for your vision.

399 Bard Rd, Bennington

$375,000

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.

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

$2,190,000

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.

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

$950,000

A rare opportunity to acquire one of Southern Vermont's most adaptable residential investment properties. Currently known as the South Shire Inn, this landmark Victorian estate offers investors immediate income potential along with exceptional opportunities for future residential or mixed-use redevelopment. The property includes nine guest accommodations, owner's quarters, expansive common areas, a detached carriage house with additional guest accommodations, a commercial kitchen, and an established Thai restaurant providing existing rental income. Its flexible floor plan and MU1 zoning support a variety of permitted residential and mixed-use possibilities, including multifamily conversion, long-term or short-term rentals, workforce housing, owner occupancy, senior living, residential care, and other redevelopment opportunities, subject to local approvals. Originally built in 1887 by renowned architect William C. Bull, the property has been thoughtfully restored while preserving its architectural character. Located within walking distance of downtown Bennington's shops, restaurants, and cultural attractions, it offers investors a distinctive asset with exceptional long-term flexibility and redevelopment potential. Seller financing and lease-to-own opportunities may be available for qualified buyers.

5072098 MLS

A rare opportunity to acquire one of Southern Vermont's most adaptable residential investment properties. Currently known as the South Shire Inn, this landmark Victorian estate offers investors immediate income potential along with exceptional opportunities for future residential or mixed-use redevelopment. The property includes nine guest accommodations, owner's quarters, expansive common areas, a detached carriage house with additional guest accommodations, a commercial kitchen, and an established Thai restaurant providing existing rental income. Its flexible floor plan and MU1 zoning support a variety of permitted residential and mixed-use possibilities, including multifamily conversion, long-term or short-term rentals, workforce housing, owner occupancy, senior living, residential care, and other redevelopment opportunities, subject to local approvals. Originally built in 1887 by renowned architect William C. Bull, the property has been thoughtfully restored while preserving its architectural character. Located within walking distance of downtown Bennington's shops, restaurants, and cultural attractions, it offers investors a distinctive asset with exceptional long-term flexibility and redevelopment potential. Seller financing and lease-to-own opportunities may be available for qualified buyers.

124 Elm St, Bennington