Bennington, VT Homes

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  $450,000

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft

  848 Coleville Rd, Bennington, VT 05201

  The House that Love Built-Multigenerational Comfort &Thoughtful DesignTucked away in a peaceful neighborhood, set back from a well maintained town road. This beautifully maintained home is perfect for wildlife watching and enjoying serene solitude.Designed with multigenerational or accessible living in mind, the home features a private in-law suite with it's own ramp entry, wide

  Beatrice O'Connell Maple Leaf Realty

  848 Coleville Rd, Bennington, VT 05201
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  /10

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  130 Union St Unit D, Bennington, VT 05201

  This 1-bedroom, 1-bathroom apartment located within the downtown of Bennington offers 700 square feet of living space. The living room features ample natural light and connects directly to the kitchen, which includes essential appliances. The bedroom provides sufficient space for a queen-sized bed and includes plenty of closet space for storage. The bathroom is equipped with standard fixtures and

  130 Union St Unit D, Bennington, VT 05201
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  /53

  $345,000 Sold Oct 16, 2025

  • 1,708 Sq Ft
  • $202/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1963

  14 Crescent Ln, Bennington, VT 05201

  An Idyllic Ranch Retreat with 235 Feet of beautiful shoreline totaling 1.3 Acres . This 2 bedroom ranch home has great water views from every room. . The large, bright primary bedroom is a sanctuary unto itself. Imagine waking each morning to the tranquil sight of lake waters stretching beyond the window, or slipping into the adjoining hot tub room for a restorative soak. This unique space leads

  Dan Mason Perrott Realty

  14 Crescent Ln, Bennington, VT 05201
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  /40

  Est $321,002 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  505 Cross Rd, Bennington, VT 05201

  505 Cross Rd, Bennington, VT 05201
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  /31

  $339,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  This inviting in-town home has been nearly completely renovated with only a few more touches to be brought by the new owner, blending fresh updates with classic comfort. Inside, you’ll find 3 bedrooms and a full bath, plus a bonus room that could serve as a 4th bedroom with a half-bath. An additional room with its own separate entrance is ideal for a small home business. The convenient attached

  Cassie Barbeau Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
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  /21

  $300,000 Sold Oct 16, 2025

  • 1,365 Sq Ft
  • $220/SF
  • 77 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1988

  339 Chester Knoll Dr, Bennington, VT 05201

  A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings.Chester Knoll provides an

  Lori Hurley Four Corner Properties LLC

  339 Chester Knoll Dr, Bennington, VT 05201
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  /40

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,976 Sq Ft

  260 Tower Rd, Bennington, VT 05201

  260 Tower Rd, Bennington, VT 05201
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  /39

  $365,000

  • 3 Beds
  • 1 Bath
  • 1,660 Sq Ft

  989 Carpenter Hill Rd, Bennington, VT 05201

  Country charm meets modern comfort... Welcome to your perfect slice of paradise! This lovingly updated ranch home is nestled on a peaceful country road and sits on a generous 2.6 acre lot, offering the ideal blend of privacy, space, and style. Step inside to discover a bright, refreshed interior featuring new vinyl plank flooring, freshly painted walls in a neutral palate, and updated lighting

  Angela Bevin Maple Leaf Realty

  989 Carpenter Hill Rd, Bennington, VT 05201
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  /39

  $250,000 Sold Oct 14, 2025

  • 1,264 Sq Ft
  • $198/SF
  • 25 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1920

  139 Mckinley St, Bennington, VT 05201

  Welcome to 139 McKinley Street in Bennington! This charming 1920 New Englander blends character and convenience in a great village location. Inside, you'll find a first-floor primary bedroom with laundry and a half bath downstairs, a cozy living room with a beautiful woodstove, and hardwood floors upstairs with easy care laminate throughout the main level.A standout feature is the

  Brooke Thomson Drew Mahar McCarthy Real Estate

  139 Mckinley St, Bennington, VT 05201
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  /40

  Est $385,278 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft

  42 Maple Grove Rd, Bennington, VT 05201

  42 Maple Grove Rd, Bennington, VT 05201
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  /35

  $475,000

  • 5 Beds
  • 2.5 Baths
  • 2,104 Sq Ft

  115 Grandview St, Bennington, VT 05201

  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

  Cassie Barbeau Mahar McCarthy Real Estate

  115 Grandview St, Bennington, VT 05201
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  /49

  $435,000 Sold Oct 10, 2025

  • 3,040 Sq Ft
  • $143/SF
  • 7 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2007

  458 Fox Hill Rd, Bennington, VT 05201

  Beautiful Colonial-style home with an oversized two-car attached garage, set in one of Bennington’s most desirable neighborhoods. This inviting home features an open kitchen and family room, a bright sunroom, formal living and dining rooms, and 2.5 baths. The primary suite is complemented by three additional bedrooms, offering plenty of space for family and guests. A versatile, walkout finished

  Kelley Mccarthy Mahar McCarthy Real Estate

  458 Fox Hill Rd, Bennington, VT 05201
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  /40

  Est $170,944 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,866 Sq Ft

  276 Finley Dr, Bennington, VT 05201

  276 Finley Dr, Bennington, VT 05201
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  /48

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 3,742 Sq Ft

  34 Southshire Dr, Bennington, VT 05201

  Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

  Kelley Mccarthy Mahar McCarthy Real Estate

  34 Southshire Dr, Bennington, VT 05201
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  /45

  $46,000 Sold Oct 10, 2025

  • 1,146 Sq Ft
  • $40/SF
  • 10 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1900

  109 County St, Bennington, VT 05201

  Great potential to bring this cute antique home back to life! Step inside from the covered side porch to a large living room that connects to two first floor rooms ready for a variety of different uses. The kitchen has a small dining area and leads to a laundry room and 3/4 bath. Keep going and you'll find a useful attached shed/utility room. Upstairs are more bedrooms with plenty of storage,

  Justine Curry Maple Leaf Realty

  109 County St, Bennington, VT 05201
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  /35

  Est $203,521 Not Listed For Sale

  • 3 Beds

  1213 Gore Rd, Bennington, VT 05201

  1213 Gore Rd, Bennington, VT 05201
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  /49

  $325,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,664 Sq Ft

  93 Pace Rd, Bennington, VT 05201

  Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

  Harvey Roettinger RE/MAX North Professionals

  93 Pace Rd, Bennington, VT 05201
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  /52

  $740,000 Sold Oct 10, 2025

  • 4,032 Sq Ft
  • $184/SF
  • 16 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1807

  77 Monument Ave, Bennington, VT 05201

  Located in the prestigious Village of Old Bennington, this stately 4,000+ sq. ft. center hall Colonial sits on 1.6 beautifully landscaped acres with a year-round creek and charming footbridge. Thoughtfully maintained, it features updates including electrical, plumbing, new roofing, and rebuilt chimneys. A gracious foyer welcomes you, flanked by a formal parlor with fireplace and half bath,

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  77 Monument Ave, Bennington, VT 05201
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  /40

  Est $569,489 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,706 Sq Ft

  402 Middle Pownal Rd, Bennington, VT 05201

  402 Middle Pownal Rd, Bennington, VT 05201
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  /48

  $299,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft

  4 Rockwood St, Bennington, VT 05201

  Found your new home! This well maintained and updated ranch on a lovely corner lot has all of the ease of one-level living with all of the space you need. Relax on the covered side porch next to the stamped concrete patio with privacy fence for outdoor entertaining. Enjoy the sights and sounds of the peaceful brook on the wooded edge of the property. Two driveways provide ample parking for you

  Justine Curry Maple Leaf Realty

  4 Rockwood St, Bennington, VT 05201
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  /34

  $399,900 Sold Oct 06, 2025

  • 1,700 Sq Ft
  • $235/SF
  • 8 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1996

  43 Spur Rd, Bennington, VT 05201

  Private and gorgeous home situated on 3.54 acres in Shaftsbury. Offering 2 bedrooms with a full primary suite (large primary bathroom and walk in closet), 3 total bathrooms and modern design. Enjoy the large airy and open living room with fireplace, modern kitchen with plenty of cupboards and marble counter top and dining area with slider to the private backyard and multi-level deck. Many

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  43 Spur Rd, Bennington, VT 05201
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  /40

  Est $597,748 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,952 Sq Ft

  88 Southshire Dr, Bennington, VT 05201

  88 Southshire Dr, Bennington, VT 05201
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  /31

  $339,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  103 Norton St, Bennington, VT 05201

  Beautifully Renovated 4-Bedroom Home with Modern Upgrades! Welcome to this stunning, move-in ready home that has been fully renovated with care and style. Offering 4 spacious bedrooms, 2 brand-new bathrooms, and 1,728 square feet of thoughtfully designed living space, this home is the perfect blend of comfort and modern living.Step inside to find gleaming hardwood floors that flow throughout

  Timothy Corcoran Mahar McCarthy Real Estate

  103 Norton St, Bennington, VT 05201
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  /4

  $45,000 Sold Oct 06, 2025

  • 1,142 Sq Ft
  • $39/SF
  • 7 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1948

  45 Shady Ln, Bennington, VT 05201

  This property presents a rare opportunity for the right buyer to restore or redevelop a home on a quiet lot at the end of a dead-end street. Tucked away in a peaceful setting with a small stream nearby, the lot offers a sense of privacy while still being within town limits. The structure needs a new roof and there is active water damage and mold. Power and water have been turned off. The house

  Erika Floriani Hoffman Real Estate

  45 Shady Ln, Bennington, VT 05201
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  /40

  Est $565,081 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,183 Sq Ft

  377 Southshire Dr, Bennington, VT 05201

  377 Southshire Dr, Bennington, VT 05201
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  /48

  $325,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,994 Sq Ft

  165 Pippin Knoll, Bennington, VT 05201

  Set well back from the road, this mid-century modern home emphasizes simple lines, an indoor-outdoor connection, and panoramic views. The main level centers on an open living/dining/kitchen area anchored by a fireplace and oversized windows that overlook the pond and rolling landscape beyond. The primary suite on this level provides private comfort. A second-floor bedroom offers a rare

  Kelley Mccarthy Mahar McCarthy Real Estate

  165 Pippin Knoll, Bennington, VT 05201
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  /33

  $230,000 Sold Sep 30, 2025

  • 1,144 Sq Ft
  • $201/SF
  • 9 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1979

  5 Center St, Bennington, VT 05201

  Welcome to 5 Center Street in the heart of Bennington! This charming single level home offers 3 bedrooms and 1 full bath across a well designed 1,144 sq. ft. floor plan the perfect size for easy living and energy efficiency. Whether you’re looking to downsize, purchase your first home, or simply enjoy the convenience of one floor living, this home is a wonderful fit.Inside, you’ll find a

  Brooke Thomson Drew Mahar McCarthy Real Estate

  5 Center St, Bennington, VT 05201
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  /40

  Est $557,967 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  179 Southshire Dr, Bennington, VT 05201

  179 Southshire Dr, Bennington, VT 05201
• 

  

  /25

  $249,000

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  1016 County St, Bennington, VT 05201

  Look no further! This charming, turnkey 2-bedroom, 3/4-bath urban farmhouse is ready to welcome you. Situated on a corner lot with mountain and Roaring Branch river views, it perfectly combines the convenience of in-town living with the beauty of Vermont. Enjoy the scenery from the covered front porch, back stone patio, or second-story balcony. Inside, the bright, open floor plan features an

  Abi Gregorio

  1016 County St, Bennington, VT 05201
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  /41

  $335,000 Sold Sep 29, 2025

  • 1,682 Sq Ft
  • $199/SF
  • 35 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1928

  23 Robinson Ave, Bennington, VT 05201

  Nestled on a quiet street just moments from the golf course, this beautiful two-story brick home offers timeless charm and modern updates. The inviting front porch and lush perennial gardens set the tone for this well-loved property, which also features a fenced-in yard, a small outbuilding, a brand-new shed, and a peaceful backyard water feature. Inside, you'll find 3 bedrooms and 1.5 baths with

  Kelley Mccarthy Mahar McCarthy Real Estate

  23 Robinson Ave, Bennington, VT 05201
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  /37

  Est $309,372 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  1065 Burgess Rd, Bennington, VT 05201

  1065 Burgess Rd, Bennington, VT 05201
• 

  

  /22

  $249,900

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft

  107 Coolidge Ave, Bennington, VT 05201

  Discover this beautifully updated home set directly on the Walloomsac River, offering 123 feet of peaceful river frontage. Enjoy fishing right from your own backyard, hosting gatherings by the water, or simply relaxing to the soothing sounds of the flowing river. Ideally located within walking distance of Main Street, the Rec Center (featuring a gym, sauna, indoor pool, and tennis and basketball

  Matt Waddington Hoffman Real Estate

  107 Coolidge Ave, Bennington, VT 05201
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  /38

  $595,000 Sold Sep 26, 2025

  • 2,184 Sq Ft
  • $272/SF
  • 71 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  359 Hickory Hill Rd, Bennington, VT 05201

  Welcome to 359 Hickory Hill! Tucked away at the end of a peaceful cul-de-sac on 2.58 acres, this beautifully updated Center Hall Colonial offers privacy, space, and convivence just minutes from downtown Bennington and major highways to New York City, Boston, and beyond.This three bedroom, two and a half bath home is truly turnkey and move in ready. Inside, you'll find gleaming hardwood and

  Brooke Thomson Drew Mahar McCarthy Real Estate

  359 Hickory Hill Rd, Bennington, VT 05201
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  /31

  Est $394,733 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,963 Sq Ft

  543 Gore Rd, Bennington, VT 05201

  543 Gore Rd, Bennington, VT 05201
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  /40

  $215,000

  • 5 Beds
  • 2 Baths
  • 2,201 Sq Ft

  317 Pleasant St, Bennington, VT 05201

  Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400).

  Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
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  /19

  $241,000 Sold Sep 25, 2025

  • 1,070 Sq Ft
  • $225/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1990

  20 Rockwood St, Bennington, VT 05201

  As sweet and tidy as can be, this 3BR/1BA home on a residential street offers one level living just outside of town. Gleaming wood floors in the living room and kitchen; kitchen is efficiently laid out and the dining area opens out to a deck overlooking the landscaped back yard and creates a private retreat for your morning coffee. Full basement has been partially finished with a room perfect

  Vicki Wilson Maple Leaf Realty

  20 Rockwood St, Bennington, VT 05201
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  /40

  Est $270,388 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  25 Center St, Bennington, VT 05201

  25 Center St, Bennington, VT 05201
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  /54

  $84,500

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  889 Overlea Rd, Bennington, VT 05201

  Tucked away on a private 1.27-acre lot, this single-wide mobile home offers a comfortable retreat with the space you’ve been looking for. A detached heated garage is perfect for year-round projects or storage, while a handy metal shed adds even more room for your tools and toys. The gently sloping, mostly open yard feels peaceful and easy to care for, with plenty of space to garden, play, or

  Catherine Cairns Maple Leaf Realty

  889 Overlea Rd, Bennington, VT 05201
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  /4

  $96,906 Sold Sep 24, 2025

  • 777 Sq Ft
  • $125/SF
  • 26 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2025

  29 Dustin Dr, Bennington, VT 05201

  Welcome to 29 Dustin Drive, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  29 Dustin Dr, Bennington, VT 05201
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  /40

  Est $288,919 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  14 Center St, Bennington, VT 05201

  14 Center St, Bennington, VT 05201

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