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$365,000

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.

3 Beds ⋅ 2 Baths ⋅ 5101687 MLS

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

12 Hall St, Bennington

$260,000

Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to downtown restaurants, theater, and parks, the location is exceptionally convenient while still feeling like a true residential neighborhood. Inside, generous rooms, abundant natural light, hardwood floors, wide moldings, and original architectural details give the home warmth and personality. The spacious living room offers flexibility for gathering, relaxing, or creating multiple seating areas, while the adjoining dining room provides an inviting setting for everyday meals and entertaining. The bright kitchen features abundant wood cabinetry, generous counter space, a farmhouse-style sink, gas range, and direct access to the rear deck. Upstairs are four bedrooms and a full bath, offering ample flexibility for household needs, guests, a home office, or creative space. The primary bedroom includes two closets, and each bedroom has a ceiling fan and overhead light. The full basement houses the laundry and utilities, provides useful storage, and includes an additional toilet. There's a hot air furnace, Rinnai water heater, 100-amp panel, and town water/sewer. Outside, the rear deck overlooks the lawn, established garden beds, and a partially fenced area. A detached one-car garage adds convenient parking, storage, or workshop potential. The home is comfortable and offers a strong foundation. Exterior painting and porch restoration will be up to the next owner, creating an opportunity to refresh the property, make it their own, and build equity over time. With its gracious proportions, original charm, outdoor space, and exceptional location, 301 Elm St is ready for its next chapter.

4 Beds ⋅ 2 Baths ⋅ 5101031 MLS

Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to downtown restaurants, theater, and parks, the location is exceptionally convenient while still feeling like a true residential neighborhood. Inside, generous rooms, abundant natural light, hardwood floors, wide moldings, and original architectural details give the home warmth and personality. The spacious living room offers flexibility for gathering, relaxing, or creating multiple seating areas, while the adjoining dining room provides an inviting setting for everyday meals and entertaining. The bright kitchen features abundant wood cabinetry, generous counter space, a farmhouse-style sink, gas range, and direct access to the rear deck. Upstairs are four bedrooms and a full bath, offering ample flexibility for household needs, guests, a home office, or creative space. The primary bedroom includes two closets, and each bedroom has a ceiling fan and overhead light. The full basement houses the laundry and utilities, provides useful storage, and includes an additional toilet. There's a hot air furnace, Rinnai water heater, 100-amp panel, and town water/sewer. Outside, the rear deck overlooks the lawn, established garden beds, and a partially fenced area. A detached one-car garage adds convenient parking, storage, or workshop potential. The home is comfortable and offers a strong foundation. Exterior painting and porch restoration will be up to the next owner, creating an opportunity to refresh the property, make it their own, and build equity over time. With its gracious proportions, original charm, outdoor space, and exceptional location, 301 Elm St is ready for its next chapter.

301 Elm St, Bennington

$439,000

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.

3 Beds ⋅ 3 Baths ⋅ 5097821 MLS

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

15 Polygraphic Ln, Bennington

$495,000

If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the owners in the '80s. The 3300+ square feet of living area on the upper level and another 3300+ on the lower level ready to be finished. As you can see, the lower level has plenty of windows and will be very flexible space to use. The two-car garage is attached to the house. From there, into the mudroom. The kitchen is very generous...There's room for your breakfast table, a couple of easy chairs and a love seat, and the woodstove will make this a cozy country kitchen to be. This is a 'cooks dream'. The commercial range will make your friends jealous, as will the pantry and stained glass on the upper cabinets. Off the kitchen is a large sunroom which leads out to the deck. Large dining room perfect for entertaining and a very comfortable formal living room. There are two guest rooms that share a tile bath. The primary suite has its own tile bath and a room that could be a nursery or an office. The lower level is ready to finish into living space if you need it. A few spots will need a bit of TLC, but the end result will be fantastic. Several updates have been done. For the handyman or animal lover, there is a 23x46 foot barn with room for several vehicles or machinery. There are two garage doors, and it even has a pit for working under your vehicles. The open land is gorgeous. Stonewalls and woodland await. If you enjoy sunny locations, this is a perfect spot. There is enough land to enroll the property into Vermont's Current Use program. This may be the spot you have been waiting for!

4 Beds ⋅ 3 Baths ⋅ 5095717 MLS

If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the owners in the '80s. The 3300+ square feet of living area on the upper level and another 3300+ on the lower level ready to be finished. As you can see, the lower level has plenty of windows and will be very flexible space to use. The two-car garage is attached to the house. From there, into the mudroom. The kitchen is very generous...There's room for your breakfast table, a couple of easy chairs and a love seat, and the woodstove will make this a cozy country kitchen to be. This is a 'cooks dream'. The commercial range will make your friends jealous, as will the pantry and stained glass on the upper cabinets. Off the kitchen is a large sunroom which leads out to the deck. Large dining room perfect for entertaining and a very comfortable formal living room. There are two guest rooms that share a tile bath. The primary suite has its own tile bath and a room that could be a nursery or an office. The lower level is ready to finish into living space if you need it. A few spots will need a bit of TLC, but the end result will be fantastic. Several updates have been done. For the handyman or animal lover, there is a 23x46 foot barn with room for several vehicles or machinery. There are two garage doors, and it even has a pit for working under your vehicles. The open land is gorgeous. Stonewalls and woodland await. If you enjoy sunny locations, this is a perfect spot. There is enough land to enroll the property into Vermont's Current Use program. This may be the spot you have been waiting for!

498 Town Line Rd, Bennington

$185,000

Fantastic opportunity to acquire your own Condo steps away from Crotched Mountain Ski Area (a Vail/Epic Resort). This cozy 2 story townhome has been Freshly Painted and has New Flooring throughout. It features an Open Concept Living Room/Kitchen with an Enormous Slider to the Very Spacious Private Deck. There is a Full Bath on the Main Level and up the Spiral Staircase is the Bedroom. There are Skylights that let in some Natural Sunlight, a Generously Sized Closet and a Ceiling Fan for those warm summer nights. Minutes to Crotched Mountain Golf Club and access to great Hiking and Biking trails this location is ideal for outdoor enthusiasts in all seasons. Less than an hour from Nashua, Manchester, Concord and Keene, NH the condo is very centrally located. Enjoy Shopping, Restaurants and Antique Shops in the quaint town of Peterborough, NH just minutes away. Whether you are looking for a Permanent Home, Second Home or possible Income Property this condo could be for you! With a Low Monthly HOA fee too! Don't miss out on this Mountainside Condo, schedule your showing today!

1 Beds ⋅ 1 Baths ⋅ 5094341 MLS

Fantastic opportunity to acquire your own Condo steps away from Crotched Mountain Ski Area (a Vail/Epic Resort). This cozy 2 story townhome has been Freshly Painted and has New Flooring throughout. It features an Open Concept Living Room/Kitchen with an Enormous Slider to the Very Spacious Private Deck. There is a Full Bath on the Main Level and up the Spiral Staircase is the Bedroom. There are Skylights that let in some Natural Sunlight, a Generously Sized Closet and a Ceiling Fan for those warm summer nights. Minutes to Crotched Mountain Golf Club and access to great Hiking and Biking trails this location is ideal for outdoor enthusiasts in all seasons. Less than an hour from Nashua, Manchester, Concord and Keene, NH the condo is very centrally located. Enjoy Shopping, Restaurants and Antique Shops in the quaint town of Peterborough, NH just minutes away. Whether you are looking for a Permanent Home, Second Home or possible Income Property this condo could be for you! With a Low Monthly HOA fee too! Don't miss out on this Mountainside Condo, schedule your showing today!

10 Onset Rd Unit 9A, Bennington

$209,000

Opportunity is knocking... answer the door! This home in a sought-after neighborhood on an almost half acre lot is the investment you've been looking for. Close to downtown shopping and dining, as well as the award-winning Southwestern Vermont Medical Center. Features include an attached two car garage, wood floors, mini-split in living room, fireplace, wood floors, dining room, primary bedroom with ensuite 3/4 bathroom, deck, and more. All four bedrooms and two bathrooms are on one level. The walk-out basement was once partially finished and could be plenty of extra living space. Come bring this property back to life! Offered well below appraised value.

4 Beds ⋅ 2 Baths ⋅ 5093692 MLS

Opportunity is knocking... answer the door! This home in a sought-after neighborhood on an almost half acre lot is the investment you've been looking for. Close to downtown shopping and dining, as well as the award-winning Southwestern Vermont Medical Center. Features include an attached two car garage, wood floors, mini-split in living room, fireplace, wood floors, dining room, primary bedroom with ensuite 3/4 bathroom, deck, and more. All four bedrooms and two bathrooms are on one level. The walk-out basement was once partially finished and could be plenty of extra living space. Come bring this property back to life! Offered well below appraised value.

142 Pine Cir, Bennington

$650,000

Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space combining a kitchen and spacious living room, where a cozy wood stove creates a warm and welcoming atmosphere. Additional living spaces include a formal dining room, private office, library space and a large mudroom with attractive brick flooring that provides a practical transition from the outdoors. Upstairs, you'll find a wonderful studio space ideal for artists, hobbyists, or anyone seeking a creative retreat. The property also boasts a huge, heated workshop, offering endless possibilities for craftspeople, entrepreneurs, or storage needs. Adding to the home's versatility is a second-floor studio apartment with its own private entrance and screened porch, making it ideal for guests, extended family, rental income, or multi-generational living. A substantial barn/garage with a loft area provides even more space for vehicles, equipment, storage, or future expansion possibilities. Recent updates include a newer boiler and hot water heater, providing peace of mind and modern efficiency. The expansive grounds offer privacy and room to roam, while approximately 100 feet of road frontage on Matteson Road may present future building opportunities, subject to local approvals. A rare North Bennington offering that combines space, charm, flexibility, and potential in a beautiful country setting.

5 Beds ⋅ 3 Baths ⋅ 5093651 MLS

Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space combining a kitchen and spacious living room, where a cozy wood stove creates a warm and welcoming atmosphere. Additional living spaces include a formal dining room, private office, library space and a large mudroom with attractive brick flooring that provides a practical transition from the outdoors. Upstairs, you'll find a wonderful studio space ideal for artists, hobbyists, or anyone seeking a creative retreat. The property also boasts a huge, heated workshop, offering endless possibilities for craftspeople, entrepreneurs, or storage needs. Adding to the home's versatility is a second-floor studio apartment with its own private entrance and screened porch, making it ideal for guests, extended family, rental income, or multi-generational living. A substantial barn/garage with a loft area provides even more space for vehicles, equipment, storage, or future expansion possibilities. Recent updates include a newer boiler and hot water heater, providing peace of mind and modern efficiency. The expansive grounds offer privacy and room to roam, while approximately 100 feet of road frontage on Matteson Road may present future building opportunities, subject to local approvals. A rare North Bennington offering that combines space, charm, flexibility, and potential in a beautiful country setting.

81 Honeysuckle Ln, Bennington

$325,000

This well-maintained ranch-style home offers the convenience of one-level living with 3 bedrooms plus a spacious primary suite. Set on a large lot, the property features two decks, providing plenty of outdoor space for entertaining, relaxing, or enjoying the backyard. An easy walk to the local golf course adds to the appeal of this desirable location. The updated kitchen boasts beautiful granite countertops and a convenient pass-through to the oversized dining room, creating an open and inviting atmosphere for gatherings. A bright and welcoming living room is filled with natural light and showcases hardwood floors throughout most of the home. Both bathrooms have been tastefully updated, complementing the home's move-in-ready condition. Recent upgrades include central air conditioning, a newer forced-air furnace, and an energy-efficient hybrid hot water heater, offering year-round comfort and efficiency. The home is also equipped with 200-amp electrical service and is wired for a generator, providing added convenience and peace of mind. With its functional floor plan, modern mechanical updates, and desirable single-level layout, this property is ready for its next owner to move in and enjoy. The large yard, two decks, updated interior, and proximity to the golf course make it an ideal place to relax, entertain, and embrace an active lifestyle. This is easy living at its best.

4 Beds ⋅ 2 Baths ⋅ 5092315 MLS

This well-maintained ranch-style home offers the convenience of one-level living with 3 bedrooms plus a spacious primary suite. Set on a large lot, the property features two decks, providing plenty of outdoor space for entertaining, relaxing, or enjoying the backyard. An easy walk to the local golf course adds to the appeal of this desirable location. The updated kitchen boasts beautiful granite countertops and a convenient pass-through to the oversized dining room, creating an open and inviting atmosphere for gatherings. A bright and welcoming living room is filled with natural light and showcases hardwood floors throughout most of the home. Both bathrooms have been tastefully updated, complementing the home's move-in-ready condition. Recent upgrades include central air conditioning, a newer forced-air furnace, and an energy-efficient hybrid hot water heater, offering year-round comfort and efficiency. The home is also equipped with 200-amp electrical service and is wired for a generator, providing added convenience and peace of mind. With its functional floor plan, modern mechanical updates, and desirable single-level layout, this property is ready for its next owner to move in and enjoy. The large yard, two decks, updated interior, and proximity to the golf course make it an ideal place to relax, entertain, and embrace an active lifestyle. This is easy living at its best.

21 Pageant St, 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

$695,000

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

$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

$399,900

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.

4 Beds ⋅ 2 Baths ⋅ 5088223 MLS

This c. 1936 4BR/2BA home has been beautifully updated to blend timeless architectural character with modern comfort and convenience. Meticulously maintained throughout, it features gleaming hardwood floors, vintage details and thoughtful updates designed for today’s lifestyle. The stunning granite kitchen offers rich cherry cabinetry and stainless steel appliances, all new in 2024, creating a warm and functional space for cooking and gathering. The expansive primary suite is a true retreat, complete with an oversized walk-in shower, double vanity with granite countertop, and abundant space to unwind. Three additional guest bedrooms and a full guest bath provide flexibility for family, guests, or home office needs. The finished attic is perfect for a playroom or creative space and the home offers abundant storage throughout. Step outside to enjoy the brand-new expansive deck overlooking the yard, along with a shed and additional outbuilding for hobbies, gardening, or extra storage. Located in the Clarks Woods neighborhood, this charming home is convenient to the country club, hospital, and other local amenities while offering the comfort of a lovely residential setting. 0.33 acre.

23 Pageant St, Bennington

$1,495,000

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

7 Beds ⋅ 6 Baths ⋅ 5075253 MLS

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

16 West Rd, Bennington

$529,000

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

3 Beds ⋅ 3 Baths ⋅ 5067086 MLS

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

58 Mount Anthony Rd, Bennington

$357,500

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!

4 Beds ⋅ 2 Baths ⋅ 5048567 MLS

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!

19 Royal St, Bennington