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Homes for Sale in 05201

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  • /53

    $599,000

    $96K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,715 Sq Ft

    58 Mount Anthony Rd, Bennington, VT 05201

    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

    Agent Photo

    Monique Geannelis

    Mahar McCarthy Real Estate

    58 Mount Anthony Rd, Bennington, VT 05201
  • /38

    $325,000

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

    89 Merson St, Woodford, VT 05201

    Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    89 Merson St, Woodford, VT 05201
  • /33

    $279,000

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    8 West St, Bennington, VT 05201

    Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    8 West St, Bennington, VT 05201
  • /41

    $550,000

    • 5 Beds
    • 2 Baths
    • 1,974 Sq Ft

    971 S Stream Rd, Bennington, VT 05201

    Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home.Situated on over 17 acres, this property offers not one but two barns, established fenced pastures,

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    971 S Stream Rd, Bennington, VT 05201
  • /19

    $179,000

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    106 Park St Unit 9, Bennington, VT 05201

    Looking for easy, low maintenance living in a location that puts everything within reach? This inviting first floor condo offers comfort, convenience, and affordability all in one package.Featuring two bedrooms, a bright and welcoming living room filled with natural light, a spacious kitchen with generous counter space, ample storage, and the convenience of having your kitchen, bathroom,

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    106 Park St Unit 9, Bennington, VT 05201
  • /27

    $209,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,075 Sq Ft

    1083 Main St, Bennington, VT 05201

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

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    1083 Main St, Bennington, VT 05201
  • /29

    $250,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    103 Jennings Brook Dr, Bennington, VT 05201

    Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

    Kelley Mccarthy Mahar McCarthy Real Estate

    103 Jennings Brook Dr, Bennington, VT 05201
  • /14

    $237,700

    • 3 Beds
    • 2 Baths
    • 1,222 Sq Ft

    117 Putnam St, Bennington, VT 05201

    This beautifully renovated 2-unit home by JDN Properties offers exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize

    Dan Mason Perrott Realty

    117 Putnam St, Bennington, VT 05201
  • /28

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    107 Jefferson Ave, Bennington, VT 05201

    Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    107 Jefferson Ave, Bennington, VT 05201
  • /50

    $160,000

    • 5 Beds
    • 2 Baths
    • 1,575 Sq Ft

    127 Dewey St, Bennington, VT 05201

    Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single-family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again.Inside, you'll find generous living space ready for your vision and updates. A

    Lindsey Martin Maple Leaf Real Estate

    127 Dewey St, Bennington, VT 05201
  • /31

    $90,000

    $35K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft

    109 Evergreen Dr, Bennington, VT 05201

    House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch,

    Zachary Zupan EXP Realty

    109 Evergreen Dr, Bennington, VT 05201
  • /6

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft

    2 Hamlin Ave, Bennington, VT 05201

    2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

    Lori Hurley Four Corner Properties LLC

    2 Hamlin Ave, Bennington, VT 05201
  • /11

    $179,900

    • 2 Beds
    • 1 Bath
    • 848 Sq Ft

    302 U S 7 S, Woodford, VT 05201

    Over 3 acres, a brook and lots of woods for walking. Room for a terraced garden, tons of parking and minutes to Bennington! This 2 bedroom ranch style home has a huge eat in kitchen and a lovely big living room with lots of windows. There is a bonus sun room with laundry. Owners are using an attached shed as a chicken coop! Sweet find at this affordable price!

    Christine Lewis Brattleboro Area Realty

    302 U S 7 S, Woodford, VT 05201
  • /52

    $230,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    113 Main St, Bennington, VT 05201

    Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

    Lindsey Martin Maple Leaf Real Estate

    113 Main St, Bennington, VT 05201
  • /27

    $189,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,485 Sq Ft

    432 South St Unit D2, Bennington, VT 05201

    Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

    Abi Gregorio

    432 South St Unit D2, Bennington, VT 05201
  • /7

    $997,000

    • Land
    • 23,086 Sq Ft
    • $1,881,132 per Acre

    153 Northside Dr, Bennington, VT 05201

    Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

    Lori Hurley Four Corner Properties LLC

    153 Northside Dr, Bennington, VT 05201
  • /9

    $279,000

    $16K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,206 Sq Ft

    116 S Branch St Unit 118, Bennington, VT 05201

    Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

    Julie Glover Mahar McCarthy Real Estate

    116 S Branch St Unit 118, Bennington, VT 05201
  • /42

    $180,000

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft

    105 Hicks Ave, Bennington, VT 05201

    Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn

    Angela Bevin Maple Leaf Real Estate

    105 Hicks Ave, Bennington, VT 05201
  • /15

    $389,000

    New Construction
    • 4 Beds
    • 2 Baths
    • 2,516 Sq Ft

    319 Chester Knoll Dr, Bennington, VT 05201

    Build Your Dream Home—Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own.This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision.Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully

    Lilli West Maple Leaf Real Estate

    319 Chester Knoll Dr, Bennington, VT 05201
  • /52

    $289,000

    • 3 Beds
    • 1.5 Baths
    • 1,411 Sq Ft

    262 Union St, Bennington, VT 05201

    Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

    William Paquin Maple Leaf Real Estate

    262 Union St, Bennington, VT 05201
  • /48

    $230,000

    • 3 Beds
    • 1.5 Baths
    • 1,128 Sq Ft

    104 Short St, Bennington, VT 05201

    Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the

    Lindsey Martin Maple Leaf Real Estate

    104 Short St, Bennington, VT 05201
  • /24

    $215,000

    $20K PRICE DROP
    • 1,300 Sq Ft

    340 Pleasant St, Bennington, VT 05201

    Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

    Melissa Nebelski Real Broker LLC

    340 Pleasant St, Bennington, VT 05201
  • /38

    $309,900

    $15K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    2 Pine Rd, Bennington, VT 05201

    Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

    Brenda Jones KW Vermont - Brenda Jones Real Estate Group

    2 Pine Rd, Bennington, VT 05201
  • /37

    $289,000

    • 4 Beds
    • 2 Baths
    • 1,146 Sq Ft

    109 County St, Bennington, VT 05201

    Welcome to your like-new home in the heart of Bennington! Within easy walking distance of the vibrant downtown district, this beautifully renovated 4-bedroom, 2-bath New Englander has been completely transformed into a truly turnkey property. Nearly every aspect of the home has been updated, allowing you to enjoy the benefits of modern, low-maintenance living from day one.Extensive

    Angela Bevin Maple Leaf Real Estate

    109 County St, Bennington, VT 05201
  • /54

    $495,000

    • 4 Beds
    • 2.5 Baths
    • 3,312 Sq Ft

    498 Townline Rd, Bennington, VT 05201

    If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

    Betty McEnaney Diamond Realty

    498 Townline Rd, Bennington, VT 05201
  • /45

    $275,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    951 Gage St, Bennington, VT 05201

    This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

    Dan Mason Perrott Realty

    951 Gage St, Bennington, VT 05201
  • /7

    $145,000

    $30K PRICE DROP
    • Land
    • 15.49 Acres
    • $9,361 per Acre

    00 Silk Rd, Bennington, VT 05201

    Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

    David White OwnerEntry.com

    00 Silk Rd, Bennington, VT 05201
  • /18

    $219,900

    • 3 Beds
    • 2 Baths
    • 1,372 Sq Ft

    420 Gore Rd, Bennington, VT 05201

    Welcome home to this charming 3-bedroom, 2-bath split-level home nestled on a beautiful 1-acre lot with stunning mountain views. Offering the perfect blend of comfort and privacy, this home features an attached garage, a spacious layout, and a peaceful backyard ideal for relaxing or entertaining.Enjoy your morning coffee or evening sunsets from one of two decks overlooking the private yard

    Kelley Mccarthy Mahar McCarthy Real Estate

    420 Gore Rd, Bennington, VT 05201
  • /25

    $950,000

    $300K PRICE DROP
    • 8,888 Sq Ft

    124 Elm St, Bennington, VT 05201

    An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

    Marek Kovac TPW Real Estate

    124 Elm St, Bennington, VT 05201
  • /2

    $2,190,000

    • Land
    • 1.16 Acres
    • $1,887,931 per Acre

    301 Northside Dr, Bennington, VT 05201

    Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

    Paul Carroccio TPW Real Estate

    301 Northside Dr, Bennington, VT 05201
  • /42

    $277,700

    $1K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 2,142 Sq Ft

    32 Albe Dr, Bennington, VT 05201

    MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances.The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large

    Beatrice O'Connell Maple Leaf Real Estate

    32 Albe Dr, Bennington, VT 05201
  • /15

    $169,000

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

    415 County St, Bennington, VT 05201

    STOP RENTING and start building equity! Call your lender today to discover the latest programs that could MAKE HOMEOWNERSHIP A REALITY. Owning may be closer than you think. The transformation inside this home is nothing short of spectacular. This move-in-ready, one-floor living bungalow has been thoughtfully designed to maximize every square foot, including a brand-new bathroom and updated

    Lori Hurley Four Corner Properties LLC

    415 County St, Bennington, VT 05201
  • /60

    $695,000

    • 4 Beds
    • 2 Baths
    • 1,614 Sq Ft

    515 Quarry Rd, Bennington, VT 05201

    Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

    Vicki Wilson Maple Leaf Real Estate

    515 Quarry Rd, Bennington, VT 05201
  • /4

    $80,000

    • 2 Beds
    • 2 Baths
    • 1,465 Sq Ft

    107 Lyons St, Bennington, VT 05201

    Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    107 Lyons St, Bennington, VT 05201
  • /8

    $65,000

    • Land
    • 1.24 Acres
    • $52,419 per Acre

    2041 East Rd, Bennington, VT 05201

    Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life. Perk test were positive for a inground leaching system, results available.

    Dan Mason Perrott Realty

    2041 East Rd, Bennington, VT 05201
  • /59

    $249,900

    • 3,569 Sq Ft

    406 Gage St, Bennington, VT 05201

    Bring this historic gem back to life and unlock its incredible potential! Rich with the timeless character and charm of a late-1800s home, this unique property features spacious rooms and many original architectural details waiting to shine again. The building includes three two-bedroom units, including a generously sized two-story unit with a kitchenette and full bathroom on the upper level.

    Justine Curry Maple Leaf Real Estate

    406 Gage St, Bennington, VT 05201
  • /33

    $295,000

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    254 Union St, Bennington, VT 05201

    Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms.

    Cassie Barbeau Mahar McCarthy Real Estate

    254 Union St, Bennington, VT 05201
  • /29

    $399,000

    $16K PRICE DROP
    • 5,208 Sq Ft

    126 Washington Ave, Bennington, VT 05201

    Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

    Vicki Wilson Maple Leaf Real Estate

    126 Washington Ave, Bennington, VT 05201
  • /20

    $475,000

    $24K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 9,000 Sq Ft

    425 Main St, Bennington, VT 05201

    15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

    Chris Long BHG Masiello Brattleboro

    425 Main St, Bennington, VT 05201
  • /43

    $550,000

    • 2 Beds
    • 2.5 Baths
    • 3,105 Sq Ft

    193 Finley Dr, Bennington, VT 05201

    Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes

    Jenifer Prouty Hoffman Hoffman Real Estate

    193 Finley Dr, Bennington, VT 05201

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