Keelerfamily.com Search Results

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

9 Beds ⋅ 7 Baths ⋅ 5074314 MLS

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

1086 West Rd, Bennington

$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

$838,500

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

3 Beds ⋅ 3 Baths ⋅ 5092136 MLS

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

682-704 Fox Hill Rd, Bennington

$700,000

Rare opportunity to own a high-performing multi-family portfolio on a spacious .75-acre lot in Bennington. This property features 9 total units spread across two well-maintained buildings. The primary 6-unit building has seen significant recent capital improvements, including a brand-new metal roof and five fully renovated apartments featuring modern finishes. The sixth unit remains occupied by a long-term, reliable tenant at their request. Adding to the property’s unique character and income stream is a dedicated basement commercial space, home to a master upholsterer who has operated there for 40 years ($600/mo). The second building on-site contains three additional units, providing a diversified rental mix and excellent scale. With major updates already completed, this is a low-maintenance addition to any portfolio.

5073362 MLS

Rare opportunity to own a high-performing multi-family portfolio on a spacious .75-acre lot in Bennington. This property features 9 total units spread across two well-maintained buildings. The primary 6-unit building has seen significant recent capital improvements, including a brand-new metal roof and five fully renovated apartments featuring modern finishes. The sixth unit remains occupied by a long-term, reliable tenant at their request. Adding to the property’s unique character and income stream is a dedicated basement commercial space, home to a master upholsterer who has operated there for 40 years ($600/mo). The second building on-site contains three additional units, providing a diversified rental mix and excellent scale. With major updates already completed, this is a low-maintenance addition to any portfolio.

202-204 Beech St, Bennington

$665,000

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

3 Beds ⋅ 3 Baths ⋅ 5065403 MLS

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

134 Monument Ave, Bennington

$640,000

Step back in time while enjoying modern comforts in this stunning c. 1787 Colonial home located in the heart of Old Bennington. Brimming with character and charm, this 3BR/3BA residence combines historic elegance with contemporary updates for today’s lifestyle. Inside, you’ll find a brand-new chef’s kitchen designed for culinary enthusiasts, complete with high-end appliances and ample counter space. The updated baths bring a fresh, modern feel, while the library with a wet bar sets the perfect scene for entertaining guests. Enjoy warm summer evenings on the screened porch overlooking the peaceful backyard—an ideal spot for gatherings or quiet relaxation. With its timeless architecture and thoughtful upgrades, this home offers the best of both worlds: classic Colonial character and modern-day comfort.

3 Beds ⋅ 3 Baths ⋅ 5060833 MLS

Step back in time while enjoying modern comforts in this stunning c. 1787 Colonial home located in the heart of Old Bennington. Brimming with character and charm, this 3BR/3BA residence combines historic elegance with contemporary updates for today’s lifestyle. Inside, you’ll find a brand-new chef’s kitchen designed for culinary enthusiasts, complete with high-end appliances and ample counter space. The updated baths bring a fresh, modern feel, while the library with a wet bar sets the perfect scene for entertaining guests. Enjoy warm summer evenings on the screened porch overlooking the peaceful backyard—an ideal spot for gatherings or quiet relaxation. With its timeless architecture and thoughtful upgrades, this home offers the best of both worlds: classic Colonial character and modern-day comfort.

55 Monument Ave, Bennington

$625,000

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

4 Beds ⋅ 3 Baths ⋅ 5099185 MLS

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

34 Monument Ave, Bennington

$605,000

Magnificent Views & 7.05 Acres in North Bennington Experience the beauty and tranquility of the Vermont countryside from this inviting three-bedroom, three-and-a-half-bath home, privately situated on 7.05 scenic acres in North Bennington. A circular driveway welcomes you to a picturesque setting of expansive lawns, mature trees, and magnificent long-range mountain views, offering an exceptional combination of privacy, open space, and classic Vermont scenery. Inside, generous, versatile living spaces include a family room, recreation room, dining room, and kitchen, providing plenty of room for everyday living and entertaining. Two fireplaces add warmth and character, while a four-season sunroom directly off the living room offers an inviting place to relax year-round. The magnificent mountain views can be enjoyed from inside the home as well, including a picture-perfect view directly from the kitchen. One of the property's most impressive features is the massive deck overlooking the countryside and distant mountains, perfect for morning coffee, outdoor dining, entertaining, or simply relaxing and enjoying Vermont's spectacular changing seasons. A fenced area provides additional space for outdoor living and activities. A solar array significantly reduces electric costs, adding energy efficiency and substantial savings. The two-car garage features an oversized storage area behind it, providing exceptional space for equipment, recreational gear, lawn and garden supplies, or additional storage. With 7.05 acres, breathtaking views, spacious living areas and a peaceful country setting, this special North Bennington property captures the beauty of Vermont living.

3 Beds ⋅ 4 Baths ⋅ 5108314 MLS

Magnificent Views & 7.05 Acres in North Bennington Experience the beauty and tranquility of the Vermont countryside from this inviting three-bedroom, three-and-a-half-bath home, privately situated on 7.05 scenic acres in North Bennington. A circular driveway welcomes you to a picturesque setting of expansive lawns, mature trees, and magnificent long-range mountain views, offering an exceptional combination of privacy, open space, and classic Vermont scenery. Inside, generous, versatile living spaces include a family room, recreation room, dining room, and kitchen, providing plenty of room for everyday living and entertaining. Two fireplaces add warmth and character, while a four-season sunroom directly off the living room offers an inviting place to relax year-round. The magnificent mountain views can be enjoyed from inside the home as well, including a picture-perfect view directly from the kitchen. One of the property's most impressive features is the massive deck overlooking the countryside and distant mountains, perfect for morning coffee, outdoor dining, entertaining, or simply relaxing and enjoying Vermont's spectacular changing seasons. A fenced area provides additional space for outdoor living and activities. A solar array significantly reduces electric costs, adding energy efficiency and substantial savings. The two-car garage features an oversized storage area behind it, providing exceptional space for equipment, recreational gear, lawn and garden supplies, or additional storage. With 7.05 acres, breathtaking views, spacious living areas and a peaceful country setting, this special North Bennington property captures the beauty of Vermont living.

436 Matteson Rd, Bennington

$600,000

Welcome to this stunning 1850s home, perfectly sited on 2.72 acres with breathtaking mountain views. With 5 bedrooms, 2 full baths, and over three decades of loving ownership, this property offers the perfect blend of historic charm and modern updates in a peaceful, scenic setting. Inside, you'll find spacious, light-filled rooms enhanced by large windows and a calming palette of neutral colors throughout. The main level boasts beautiful hardwood floors, a formal living room, and an elegant dining room -ideal for entertaining or family gatherings. The updated kitchen is both functional and stylish, complemented by a large island. The cozy family room features a gas fireplace and a stunning bay window that frames the natural beauty outside, making it a perfect space to relax year-round. Step out onto the architect-designed covered porch and take in the mountain views-it’s a tranquil retreat like no other. Outbuildings include a former four-stall horse barn, now used as excellent storage, and a second barn that has been transformed into a four-car garage with additional storage above -perfect for hobbies, vehicles, or workshop space. This rare property offers historic charm, modern comfort, and unbeatable views-an exceptional opportunity for those seeking space, serenity, and timeless New England character.

5 Beds ⋅ 2 Baths ⋅ 5042759 MLS

Welcome to this stunning 1850s home, perfectly sited on 2.72 acres with breathtaking mountain views. With 5 bedrooms, 2 full baths, and over three decades of loving ownership, this property offers the perfect blend of historic charm and modern updates in a peaceful, scenic setting. Inside, you'll find spacious, light-filled rooms enhanced by large windows and a calming palette of neutral colors throughout. The main level boasts beautiful hardwood floors, a formal living room, and an elegant dining room -ideal for entertaining or family gatherings. The updated kitchen is both functional and stylish, complemented by a large island. The cozy family room features a gas fireplace and a stunning bay window that frames the natural beauty outside, making it a perfect space to relax year-round. Step out onto the architect-designed covered porch and take in the mountain views-it’s a tranquil retreat like no other. Outbuildings include a former four-stall horse barn, now used as excellent storage, and a second barn that has been transformed into a four-car garage with additional storage above -perfect for hobbies, vehicles, or workshop space. This rare property offers historic charm, modern comfort, and unbeatable views-an exceptional opportunity for those seeking space, serenity, and timeless New England character.

126 Fox Hill Rd, Bennington

$565,000

Nestled on a quiet dead-end road right on the Greenfield-Bennington line, this beautifully renovated Cape-style home offers an unparalleled blend of privacy and outdoor adventure. Situated perfectly at the base of Crotched Mountain, the unique property close to hundreds of acres of pristine conservation land, with the Crotched Mountain Hiking Trail accessible right at the end of the driveway. Outdoor living shines with a sprawling composite deck with an attached greenhouse that overlooks well manicured grounds, vibrant gardens, and a patio, all wrapped in serene seclusion. Inside, the feature-rich home boasts exposed beams, built in cabinets, a formal dining room, a dedicated office space, and cozy wood stoves and fireplace to gather around. Full house basement including large main workspace, multiple storage rooms and an attached garage. Complete with a detached 2 car garage and easy access to a charming town beach on Whittemore Lake, this remarkable estate truly has it all—allowing you to walk to the lake, drive to Crotched Mountain in minutes, and fully embrace the quintessential lifestyle of the Monadnock Region.

4 Beds ⋅ 2 Baths ⋅ 5095203 MLS

Nestled on a quiet dead-end road right on the Greenfield-Bennington line, this beautifully renovated Cape-style home offers an unparalleled blend of privacy and outdoor adventure. Situated perfectly at the base of Crotched Mountain, the unique property close to hundreds of acres of pristine conservation land, with the Crotched Mountain Hiking Trail accessible right at the end of the driveway. Outdoor living shines with a sprawling composite deck with an attached greenhouse that overlooks well manicured grounds, vibrant gardens, and a patio, all wrapped in serene seclusion. Inside, the feature-rich home boasts exposed beams, built in cabinets, a formal dining room, a dedicated office space, and cozy wood stoves and fireplace to gather around. Full house basement including large main workspace, multiple storage rooms and an attached garage. Complete with a detached 2 car garage and easy access to a charming town beach on Whittemore Lake, this remarkable estate truly has it all—allowing you to walk to the lake, drive to Crotched Mountain in minutes, and fully embrace the quintessential lifestyle of the Monadnock Region.

19 Rogers Rd, Bennington

$545,000

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

$540,000

Discover 22 Merrill Drive, a masterpiece of modern efficiency and Monadnock charm. Set on two sprawling acres in Bennington, this home has undergone a stunning transformation within the past year. Experience energy independence with a brand-new solar system and the luxury of full-home AC via sleek mini-splits. The interior radiates with new flooring throughout and a chef-inspired kitchen refresh featuring premium quartz countertops and a deep new sink. For cozy NH evenings, light the new pellet stove or rely on the top-tier Buderus furnace for high-efficiency warmth. The layout offers unmatched versatility. A semi-finished basement bonus room provides the perfect flex space, while the primary suite features a spa-like jet tub and gleaming hard wood floors. Hobbyists will love the insulated garage and the massive new carport built for all your recreational toys. Above the garage, a bonus room with dual access (interior and exterior) beckons as an ideal home office or potential apartment—complete with a custom built-in train set! Step out from the deck to your refreshing above-ground pool or explore the vast, open yard that leads directly to a network of serene hiking and snowmobiling trails. Your paved driveway offers easy access to the vibrant culture and acclaimed schools of nearby Peterborough. With Crotched Mountain Ski Area, local rivers, and pristine lakes just minutes away, this property is the ultimate gateway to the New Hampshire lifestyle. This isn’t just a house; it’s your future sanctuary.

3 Beds ⋅ 2 Baths ⋅ 5073875 MLS

Discover 22 Merrill Drive, a masterpiece of modern efficiency and Monadnock charm. Set on two sprawling acres in Bennington, this home has undergone a stunning transformation within the past year. Experience energy independence with a brand-new solar system and the luxury of full-home AC via sleek mini-splits. The interior radiates with new flooring throughout and a chef-inspired kitchen refresh featuring premium quartz countertops and a deep new sink. For cozy NH evenings, light the new pellet stove or rely on the top-tier Buderus furnace for high-efficiency warmth. The layout offers unmatched versatility. A semi-finished basement bonus room provides the perfect flex space, while the primary suite features a spa-like jet tub and gleaming hard wood floors. Hobbyists will love the insulated garage and the massive new carport built for all your recreational toys. Above the garage, a bonus room with dual access (interior and exterior) beckons as an ideal home office or potential apartment—complete with a custom built-in train set! Step out from the deck to your refreshing above-ground pool or explore the vast, open yard that leads directly to a network of serene hiking and snowmobiling trails. Your paved driveway offers easy access to the vibrant culture and acclaimed schools of nearby Peterborough. With Crotched Mountain Ski Area, local rivers, and pristine lakes just minutes away, this property is the ultimate gateway to the New Hampshire lifestyle. This isn’t just a house; it’s your future sanctuary.

22 Merrill Dr, Bennington

$525,000

Mountain views, walkable access to downtown Bennington, and a complete 2023 renovation make this beautifully reimagined home a rare turnkey opportunity in one of the area’s most desirable neighborhoods. Smartly redesigned from the inside out with an emphasis on quality, comfort, and long-term efficiency, resulting in a fully refreshed interior with modern systems and an effortless flow throughout the living spaces. The flexible 4–5 bedroom layout offers exceptional versatility, featuring two spacious primary suites, a stunning bonus room with vaulted ceilings and a gas fireplace ideal for a bedroom or office, and a finished lower level with two additional bedrooms and a generous family room—perfect for hosting guests, extended family, or creating multiple living areas. At the heart of the home is a bright, beautifully designed white kitchen featuring luxury appliances and seamless access to the new deck and backyard—ideal for entertaining or enjoying peaceful mornings with mountain views. Extensive system upgrades provide true peace of mind, including a new boiler, energy-efficient mini-split heat pumps providing heating and central air conditioning, and a heat pump water heater. Additional improvements include spray-foam insulation throughout to meet Vermont energy efficiency standards and large basement egress windows that enhance both safety and natural light. The one-car garage has been thoughtfully transformed into a game room and additional storage space, creating a fun and functional recreation area while still offering the option to easily restore traditional parking if desired. Located less than a mile from the Four Corners, the property offers the best of both worlds—peaceful neighborhood living with convenient walkability to Bennington’s shops, restaurants, and community events. Currently operating as a very successful short-term rental and offered fully furnished, this exceptional home is the epitome of a Vermont retreat. Don't wait, book today!

5 Beds ⋅ 4 Baths ⋅ 5078093 MLS

Mountain views, walkable access to downtown Bennington, and a complete 2023 renovation make this beautifully reimagined home a rare turnkey opportunity in one of the area’s most desirable neighborhoods. Smartly redesigned from the inside out with an emphasis on quality, comfort, and long-term efficiency, resulting in a fully refreshed interior with modern systems and an effortless flow throughout the living spaces. The flexible 4–5 bedroom layout offers exceptional versatility, featuring two spacious primary suites, a stunning bonus room with vaulted ceilings and a gas fireplace ideal for a bedroom or office, and a finished lower level with two additional bedrooms and a generous family room—perfect for hosting guests, extended family, or creating multiple living areas. At the heart of the home is a bright, beautifully designed white kitchen featuring luxury appliances and seamless access to the new deck and backyard—ideal for entertaining or enjoying peaceful mornings with mountain views. Extensive system upgrades provide true peace of mind, including a new boiler, energy-efficient mini-split heat pumps providing heating and central air conditioning, and a heat pump water heater. Additional improvements include spray-foam insulation throughout to meet Vermont energy efficiency standards and large basement egress windows that enhance both safety and natural light. The one-car garage has been thoughtfully transformed into a game room and additional storage space, creating a fun and functional recreation area while still offering the option to easily restore traditional parking if desired. Located less than a mile from the Four Corners, the property offers the best of both worlds—peaceful neighborhood living with convenient walkability to Bennington’s shops, restaurants, and community events. Currently operating as a very successful short-term rental and offered fully furnished, this exceptional home is the epitome of a Vermont retreat. Don't wait, book today!

706 Jefferson Hts, Bennington

$505,000

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

$500,000

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

3 Beds ⋅ 3 Baths ⋅ 5082188 MLS

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

4 Stonehedge Dr, Bennington

$480,000

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

3 Beds ⋅ 3 Baths ⋅ 5102749 MLS

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

82 Pine Meadows Cir, Bennington

$480,000

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

5073533 MLS

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

8 Main St, Bennington

$480,000

Nestled in one of Bennington’s most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm—all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System (BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious living room featuring a wood-burning fireplace and French doors that open to a private deck overlooking the park-like backyard. A separate study offers space for work or reading, while a dedicated laundry room, half bath, and entry to the attached two-car garage add convenience. Upstairs, you’ll find four generously sized bedrooms, including a serene primary suite with a walk-in closet, an additional shoe closet, and a private en suite bath. A full hall bath serves the remaining bedrooms. The fully insulated basement provides excellent storage and features a new electric hot water tank with temperature controls. Outside, mature trees, lilacs, hydrangeas, berry bushes, herbs, and chestnut trees create a lush, beautifully landscaped setting. Move-in ready and meticulously maintained, this turn-key home offers classic comfort in a truly idyllic location. --

4 Beds ⋅ 3 Baths ⋅ 5045672 MLS

Nestled in one of Bennington’s most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm—all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System (BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious living room featuring a wood-burning fireplace and French doors that open to a private deck overlooking the park-like backyard. A separate study offers space for work or reading, while a dedicated laundry room, half bath, and entry to the attached two-car garage add convenience. Upstairs, you’ll find four generously sized bedrooms, including a serene primary suite with a walk-in closet, an additional shoe closet, and a private en suite bath. A full hall bath serves the remaining bedrooms. The fully insulated basement provides excellent storage and features a new electric hot water tank with temperature controls. Outside, mature trees, lilacs, hydrangeas, berry bushes, herbs, and chestnut trees create a lush, beautifully landscaped setting. Move-in ready and meticulously maintained, this turn-key home offers classic comfort in a truly idyllic location. --

245 Southshire Dr, Bennington

$469,000

MOVE IN READY - BEAUTIFUL NEW CONSTRUCTION with an AWESOME FLOOR PLAN! Peaceful rural location set on 3 acres, with room for expansion. Close to lots of Skiing including right next door at Crotched Mountain. This Home was Built with Sensible Thought, Care, and Quality Workmanship. It features Gleaming Hardwood Floors throughout the first floor, as well as a Spacious, Bright Kitchen Appointed with Brazilian Granite Counters, Stainless Steel Appliances, and an Adjoining Dining Area a with glass slider leading to the New Deck. The Large Living Room runs from End to End - Great for any Layout, and a First Floor Laundry Room and Half Bath. Upstairs you will find a Master Suite with its Own Bathroom, Walk in Closet, and a Second Closet, 2 other Spacious Bedrooms both with Large Closets, and a Full Bath Complete the Second Floor. The Full Basement is open and easily finish-able, also equipped with a generator hook up. Outside is Surrounded by a Nice, Private, Tree Lined Yard, with Room to Expand. Vinyl Siding and Pressure Treated Decking make for Years of Maintenance Free Enjoyment. Make an appointment to view your Brand New Home today. Open House Saturday 11-1pm.

3 Beds ⋅ 3 Baths ⋅ 5052812 MLS

MOVE IN READY - BEAUTIFUL NEW CONSTRUCTION with an AWESOME FLOOR PLAN! Peaceful rural location set on 3 acres, with room for expansion. Close to lots of Skiing including right next door at Crotched Mountain. This Home was Built with Sensible Thought, Care, and Quality Workmanship. It features Gleaming Hardwood Floors throughout the first floor, as well as a Spacious, Bright Kitchen Appointed with Brazilian Granite Counters, Stainless Steel Appliances, and an Adjoining Dining Area a with glass slider leading to the New Deck. The Large Living Room runs from End to End - Great for any Layout, and a First Floor Laundry Room and Half Bath. Upstairs you will find a Master Suite with its Own Bathroom, Walk in Closet, and a Second Closet, 2 other Spacious Bedrooms both with Large Closets, and a Full Bath Complete the Second Floor. The Full Basement is open and easily finish-able, also equipped with a generator hook up. Outside is Surrounded by a Nice, Private, Tree Lined Yard, with Room to Expand. Vinyl Siding and Pressure Treated Decking make for Years of Maintenance Free Enjoyment. Make an appointment to view your Brand New Home today. Open House Saturday 11-1pm.

128 Onset Rd, Bennington

$460,000

Check out this inviting 3-bedroom, 2-bath Colonial in a quiet, very private neighborhood. Onset road is a scenic residential loop with no through traffic, serving only the homes along it and providing a peaceful atmosphere beside Crotched Mountain Ski and Ride. Built in 2005, the home features approximately 1,656 square feet of finished living space, along with additional finished basement space for added flexibility. A mudroom/laundry room as you enter addition adds practical everyday convenience. This home offers a comfortable layout with plenty of space to make your own! Outside, enjoy the benefits of a unique 1-acre landscaped lot with a detached 22' x 34' garage with attic space, a 10' x 18' storage shed, and a 12' x 12' deck- providing plenty of room for vehicles, storage, hobbies, and outdoor enjoyment. This property has been thoughtfully maintained over the years. Located in the charming town of Bennington, on the Francestown border, this property offers the opportunity to enjoy a comfortable home with useful outbuildings and plenty of space both inside and out. Being moments from Crotched Mountain Ski area and Crotched Mountain Golf Resort has it's perks! This area is rich with hiking trails, lakes and rivers to enjoy and explore.

3 Beds ⋅ 2 Baths ⋅ 5104531 MLS

Check out this inviting 3-bedroom, 2-bath Colonial in a quiet, very private neighborhood. Onset road is a scenic residential loop with no through traffic, serving only the homes along it and providing a peaceful atmosphere beside Crotched Mountain Ski and Ride. Built in 2005, the home features approximately 1,656 square feet of finished living space, along with additional finished basement space for added flexibility. A mudroom/laundry room as you enter addition adds practical everyday convenience. This home offers a comfortable layout with plenty of space to make your own! Outside, enjoy the benefits of a unique 1-acre landscaped lot with a detached 22' x 34' garage with attic space, a 10' x 18' storage shed, and a 12' x 12' deck- providing plenty of room for vehicles, storage, hobbies, and outdoor enjoyment. This property has been thoughtfully maintained over the years. Located in the charming town of Bennington, on the Francestown border, this property offers the opportunity to enjoy a comfortable home with useful outbuildings and plenty of space both inside and out. Being moments from Crotched Mountain Ski area and Crotched Mountain Golf Resort has it's perks! This area is rich with hiking trails, lakes and rivers to enjoy and explore.

115 Onset Rd, Bennington

$455,000

Mountain Views • Privacy • Monadnock Region Rare Gem! Set on 8 private acres with a seasonal brook, this beautifully maintained custom-built home offers stunning views of Crotched Mountain in the heart of the Monadnock Region. Owned by the same family since it was built, this property blends warmth, craftsmanship, and opportunity. Features include hardwood floors throughout, a sun-filled solarium (passive solar system for heating) and an attached greenhouse, perfect for year-round gardening. Relax on the large screened-in porch or entertain on the spacious deck while taking in peaceful mountain views. The partially finished basement includes existing plumbing, offering expansion potential. A 3-bedroom leach field and septic system installed in 2018 adds peace of mind. Possibly subdividable. Multiple mature fruit trees, berry bushes and 30x50 garden area! Ideal for homesteading, livestock, or the avid gardener, this property offers endless possibilities in a serene private setting. Please see the attached list of special property features!

3 Beds ⋅ 2 Baths ⋅ 5073719 MLS

Mountain Views • Privacy • Monadnock Region Rare Gem! Set on 8 private acres with a seasonal brook, this beautifully maintained custom-built home offers stunning views of Crotched Mountain in the heart of the Monadnock Region. Owned by the same family since it was built, this property blends warmth, craftsmanship, and opportunity. Features include hardwood floors throughout, a sun-filled solarium (passive solar system for heating) and an attached greenhouse, perfect for year-round gardening. Relax on the large screened-in porch or entertain on the spacious deck while taking in peaceful mountain views. The partially finished basement includes existing plumbing, offering expansion potential. A 3-bedroom leach field and septic system installed in 2018 adds peace of mind. Possibly subdividable. Multiple mature fruit trees, berry bushes and 30x50 garden area! Ideal for homesteading, livestock, or the avid gardener, this property offers endless possibilities in a serene private setting. Please see the attached list of special property features!

185 Larkin Hill Rd, Bennington

$450,000

Location! Welcome to this charming and very well maintained home on desirable Elm Street. Featuring three bedrooms and two bathrooms, this sweet property offers plenty of space, character, and versatility. One of the bedrooms has been thoughtfully transformed into a spacious walk-in closet/dressing room, but it can easily be converted back into a bedroom to restore the home's full three bedroom layout. For added convenience, there are two sets of washers and dryers; one located in the basement and another on the second floor in the converted bedroom/closet. The chefs kitchen has a perfect layout for cooking at home and easily flows to the dining room for family meals, or entertaining friends. Beautiful wood floors add warmth and character throughout the home, while the fireplace in the living room creates a cozy spot to gather on cool evenings. The covered front porch is perfect for enjoying your morning coffee or unwinding at the end of the day. Outside, the property boasts an impressive 1.50-acre double lot, providing plenty of room for gardens, entertaining, outdoor activities, and family fun. Easy drive to Albany, Amtrak train station and Albany Airport in 45 minutes. A two minute drive to the hospital, close to town for walking to restaurants, library and close to the country club for golfing. Monument Elementary School is close by and easily accessed. The best skiing on the east coast and plenty of recreation is not far. Come see all that this lovely home has to offer. I'd love to show you around!

3 Beds ⋅ 2 Baths ⋅ 5111024 MLS

Location! Welcome to this charming and very well maintained home on desirable Elm Street. Featuring three bedrooms and two bathrooms, this sweet property offers plenty of space, character, and versatility. One of the bedrooms has been thoughtfully transformed into a spacious walk-in closet/dressing room, but it can easily be converted back into a bedroom to restore the home's full three bedroom layout. For added convenience, there are two sets of washers and dryers; one located in the basement and another on the second floor in the converted bedroom/closet. The chefs kitchen has a perfect layout for cooking at home and easily flows to the dining room for family meals, or entertaining friends. Beautiful wood floors add warmth and character throughout the home, while the fireplace in the living room creates a cozy spot to gather on cool evenings. The covered front porch is perfect for enjoying your morning coffee or unwinding at the end of the day. Outside, the property boasts an impressive 1.50-acre double lot, providing plenty of room for gardens, entertaining, outdoor activities, and family fun. Easy drive to Albany, Amtrak train station and Albany Airport in 45 minutes. A two minute drive to the hospital, close to town for walking to restaurants, library and close to the country club for golfing. Monument Elementary School is close by and easily accessed. The best skiing on the east coast and plenty of recreation is not far. Come see all that this lovely home has to offer. I'd love to show you around!

349 Elm St, Bennington

$450,000

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

3 Beds ⋅ 3 Baths ⋅ 5079776 MLS

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

32 Cortland Ln, Bennington

$450,000

3 Beds ⋅ 3 Baths ⋅ 5076595 MLS

356 Elm St, Bennington

$450,000

Welcome to 301 Greenfield Road, a beautifully updated lakefront retreat on the shores of Whittemore Lake. This charming 2 bedroom, 1 bathroom home combines modern comforts with rustic New England character, offering the perfect getaway or year round residence. Step inside to find a warm and inviting interior with exposed wood accents, a cozy fireplace, and expansive glass doors that frame breathtaking water views. The updated kitchen features stainless steel appliances, butcher block counters, and thoughtful storage, while the dining area and living spaces are designed for both comfort and style. Wake up to lake views from the bedroom, then enjoy your morning coffee on the screened porch or expansive deck overlooking the water. Outdoor living is unmatched here, with multiple gathering spaces including a lakeside fire pit, private dock for kayaking or fishing, and plenty of room for entertaining. Nestled among mature trees, this property offers privacy and tranquility while still being conveniently located just minutes to the town of Bennington and Crotched Mountain Ski Resort. Whether you’re seeking a cozy lakeside lifestyle, a weekend retreat, or an investment opportunity, this home delivers it all. Schedule your private showing or come see us at one of our Open Houses on 10/4/25 and 10/5/25 from 12pm to 2pm!

2 Beds ⋅ 1 Baths ⋅ 5063703 MLS

Welcome to 301 Greenfield Road, a beautifully updated lakefront retreat on the shores of Whittemore Lake. This charming 2 bedroom, 1 bathroom home combines modern comforts with rustic New England character, offering the perfect getaway or year round residence. Step inside to find a warm and inviting interior with exposed wood accents, a cozy fireplace, and expansive glass doors that frame breathtaking water views. The updated kitchen features stainless steel appliances, butcher block counters, and thoughtful storage, while the dining area and living spaces are designed for both comfort and style. Wake up to lake views from the bedroom, then enjoy your morning coffee on the screened porch or expansive deck overlooking the water. Outdoor living is unmatched here, with multiple gathering spaces including a lakeside fire pit, private dock for kayaking or fishing, and plenty of room for entertaining. Nestled among mature trees, this property offers privacy and tranquility while still being conveniently located just minutes to the town of Bennington and Crotched Mountain Ski Resort. Whether you’re seeking a cozy lakeside lifestyle, a weekend retreat, or an investment opportunity, this home delivers it all. Schedule your private showing or come see us at one of our Open Houses on 10/4/25 and 10/5/25 from 12pm to 2pm!

301 Greenfield Rd, Bennington

$440,000

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

3 Beds ⋅ 3 Baths ⋅ 5087236 MLS

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

125 Pine Meadows Cir, Bennington

$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

$436,400

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

3 Beds ⋅ 2 Baths ⋅ 5080205 MLS

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

Lot 10-48-2 Old Stagecoach, Bennington

$435,000

Step into Bennington’s past with the Norton-Fenton House, a distinguished Greek Revival building located at 206–208 Pleasant Street in the heart of the Downtown Historic District. Built in 1838, this stately structure was originally constructed as a double home for Judge Luman Norton and his daughter and son-in-law. The Norton family was deeply involved in Bennington’s celebrated pottery industry, and their legacy is woven into the fabric of the town’s history. Over the years, this building has served many purposes, most recently as the longtime home of Heritage Family Credit Union. Today, it offers over 6,200 square feet of flexible space, ideal for continued commercial use, adaptive reuse, or mixed-use redevelopment. Its tall windows, symmetrical façade, and classic proportions exemplify the elegance of Greek Revival architecture, while its solid construction and historic charm make it a standout in the downtown landscape. Perfectly situated just steps from Main Street, the property is surrounded by restaurants, shops, galleries, and civic amenities. It benefits from high visibility, steady foot traffic, and easy access to public parking. As a contributing structure in Bennington’s Downtown Historic District, the Norton-Fenton House may also be eligible for historic preservation tax credits and incentives.

5041984 MLS

Step into Bennington’s past with the Norton-Fenton House, a distinguished Greek Revival building located at 206–208 Pleasant Street in the heart of the Downtown Historic District. Built in 1838, this stately structure was originally constructed as a double home for Judge Luman Norton and his daughter and son-in-law. The Norton family was deeply involved in Bennington’s celebrated pottery industry, and their legacy is woven into the fabric of the town’s history. Over the years, this building has served many purposes, most recently as the longtime home of Heritage Family Credit Union. Today, it offers over 6,200 square feet of flexible space, ideal for continued commercial use, adaptive reuse, or mixed-use redevelopment. Its tall windows, symmetrical façade, and classic proportions exemplify the elegance of Greek Revival architecture, while its solid construction and historic charm make it a standout in the downtown landscape. Perfectly situated just steps from Main Street, the property is surrounded by restaurants, shops, galleries, and civic amenities. It benefits from high visibility, steady foot traffic, and easy access to public parking. As a contributing structure in Bennington’s Downtown Historic District, the Norton-Fenton House may also be eligible for historic preservation tax credits and incentives.

206 Pleasant St, Bennington

$435,000

Step into timeless elegance with this beautifully restored Victorian home, showcasing stunning woodwork and thoughtful updates throughout. This spacious residence offers five bedrooms, one being on the first floor, and two updated bathrooms blending classic character with modern comfort. A whimsical hidden quarter bath under the stairs adds both charm and function. The home’s gracious layout highlights detailed millwork, soaring ceilings, and large updated and energy efficient windows that flood each room with natural light. A welcoming front porch and stately exterior details reflect the home’s historic charm. It has been meticulously restored and maintained from top to bottom in recent years. The carriage house, with its new, custom doors, provides endless possibilities—perfect for storage, a workshop, or conversion into a creative studio space. With its blend of period craftsmanship and modern updates, this property offers a rare opportunity to own a piece of history while enjoying all the conveniences of today. Just steps from downtown and the hospital and less than an hour to the Albany airport, this is the one you've been waiting for.

5 Beds ⋅ 3 Baths ⋅ 5061216 MLS

Step into timeless elegance with this beautifully restored Victorian home, showcasing stunning woodwork and thoughtful updates throughout. This spacious residence offers five bedrooms, one being on the first floor, and two updated bathrooms blending classic character with modern comfort. A whimsical hidden quarter bath under the stairs adds both charm and function. The home’s gracious layout highlights detailed millwork, soaring ceilings, and large updated and energy efficient windows that flood each room with natural light. A welcoming front porch and stately exterior details reflect the home’s historic charm. It has been meticulously restored and maintained from top to bottom in recent years. The carriage house, with its new, custom doors, provides endless possibilities—perfect for storage, a workshop, or conversion into a creative studio space. With its blend of period craftsmanship and modern updates, this property offers a rare opportunity to own a piece of history while enjoying all the conveniences of today. Just steps from downtown and the hospital and less than an hour to the Albany airport, this is the one you've been waiting for.

115 Grandview St, Bennington

How much is your home worth?

How much is your home worth?