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Bennington, VT Homes for Sale

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  • /11

    $185,000

    • 4 Beds
    • 2 Baths
    • 2,643 Sq Ft

    905 County St, Bennington, VT 05201

    Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 204-5943

    905 County St, Bennington, VT 05201
  • /39

    $289,000

    • 3 Beds
    • 1 Bath
    • 1,608 Sq Ft

    30 Harbour Rd, Bennington, VT 05201

    Welcome to the charming ranch home nestled in a desirable and quiet neighborhood! This beautifully maintained three bedroom home offers comfort, style, and fantastic features throughout. The recently renovated full bathroom is a true highlight, featuring a stunning fully tiled walk in shower complete with a built in bench.Enjoy the comfort and efficiency of a brand new mini split, and cook with

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 858-4107

    30 Harbour Rd, Bennington, VT 05201
  • /4

    $225,000

    • 5 Beds
    • 2 Baths
    • 1,478 Sq Ft

    32-34 Sage St, Bennington, VT 05257

    Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 402-4994

    32-34 Sage St, Bennington, VT 05257
  • /20

    $750,000

    • 4 Beds
    • 5 Baths
    • 6,650 Sq Ft

    338 Main St, Bennington, VT 05201

    Don't miss your opportunity to own one of the area's most prestigious properties. The "Marble Bank" is located at the intersection of US Route 7 and Vermont Route 9 and is currently the landmark Fiddlehead Gallery. This property offers unique and grand architecture to go along with its high visibility location. Downtown's redevelopment and thriving new businesses make this location even more

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 347-6655

    338 Main St, Bennington, VT 05201
  • /4

    $279,000

    • 4 Beds
    • 4 Baths
    • 2,080 Sq Ft

    123 Bradford St, Bennington, VT 05201

    4 unit apartment building with great rental history and income. Front and back porches and balcony. Great location. Showings to begin 6/10/2024

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 210-1728

    123 Bradford St, Bennington, VT 05201
  • /32

    $189,900

    • 3 Beds
    • 1 Bath
    • 1,576 Sq Ft

    7 Scarey Ln, North Bennington, VT 05257

    Walking distance to Bennington College! Perfect for college housing. The property has a scenic path alongside the river so students can walk or bike to school without having to be on the road. Currently used as a single family home or can easily be converted to a duplex. This 3 bedroom North Bennington home is set in a quiet location with only ten homes in the little neighborhood with dead end

    Agent Photo

    Lisa Friedman

    Great American Dream Realty

    (802) 523-3998

    7 Scarey Ln, North Bennington, VT 05257
  • /46

    $425,000

    • 3 Beds
    • 3 Baths
    • 1,728 Sq Ft

    4 Bank St, Bennington, VT 05201

    Across from the 5th Fairway of the Mount Anthony Country Club you’ll find this charming, meticulously maintained 3 bedroom 2 bath home. The spacious open layout, custom kitchen, and expansive deck are warm and inviting. Relax on your front porch and enjoy the scenic mountain vistas of Mount Anthony and the Bennington Monument. Fabulous, convenient location! The home began as a bungalow, the

    Margretta Fischer Wohler Realty Group

    4 Bank St, Bennington, VT 05201
  • /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 enhanced by

    Kelley Mccarthy Mahar McCarthy Real Estate

    34 Southshire Dr, Bennington, VT 05201
  • /12

    $575,000

    • 6 Beds
    • 4 Baths
    • 15,179 Sq Ft

    423 Main St, Bennington, VT 05201

    Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor

    Chris Long BHG Masiello Brattleboro

    423 Main St, Bennington, VT 05201
  • /37

    $675,000

    • 9 Beds
    • 8.5 Baths
    • 4,995 Sq Ft

    722 Main St, Bennington, VT 05201

    Imagine owning the oldest home in downtown Bennington full of history and amazing detail. Built by Joseph Safford after opening Bennington's first Grist Mill, then fully renovated during the Italianate Victorian area for much of it's current design. This historic Inn along the Walloomsac River is now being used as an Air BnB rental as well as a separate leased 2 bedroom apartment. The Fully

    Lilli West Maple Leaf Realty

    722 Main St, Bennington, VT 05201
  • /54

    $215,000

    • 4 Beds
    • 3 Baths
    • 2,162 Sq Ft

    304 North St Unit 6, Bennington, VT 05201

    Great Investment Opportunity! This well-maintained 3-unit property is a fantastic opportunity for savvy investors. Two of the units are currently rented, providing immediate income potential. Situated just a short stroll from downtown, you'll find charming shops, popular restaurants, and close proximity to the Bennington trail system—perfect for outdoor enthusiasts. Just 1 hour from Albany and

    Thomas Martins Maple Leaf Realty

    304 North St Unit 6, Bennington, VT 05201
  • /32

    $185,000

    • 2 Beds
    • 1.5 Baths
    • 1,155 Sq Ft

    106 Park St Unit 1, Bennington, VT 05201

    Welcome to Unit #1 at Norton Potters, a quaint and quiet townhouse community nestled in a lovely neighborhood setting. This end-unit two-bedroom home is full of character and natural light, offering a peaceful retreat with a deck that overlooks a serene stream.The main level features a spacious living room, dining area, kitchen with a generous pantry, a convenient half bath, and laundry area.

    Faith Rhodes Maple Leaf Realty

    106 Park St Unit 1, Bennington, VT 05201
  • /30

    $349,000

    • 3 Beds
    • 1 Bath
    • 2,032 Sq Ft

    198 Weeks St, Bennington, VT 05201

    Step into this beautiful 1930s classic home, filled with character and endless possibilities. This home offers three bedrooms, one bathroom, and a layout that seamlessly combines classic details with comfortable living spaces. The heart of the home is the large dining area, perfect for hosting gatherings or enjoying quiet family meals. Adjacent, you will find a spacious living room with a

    Margretta Fischer Wohler Realty Group

    198 Weeks St, Bennington, VT 05201
  • /54

    $325,000

    • 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 everything:All

    Harvey Roettinger RE/MAX North Professionals

    93 Pace Rd, Bennington, VT 05201
  • /58

    $269,000

    • 7 Beds
    • 4 Baths
    • 4,417 Sq Ft

    200 Depot St, Bennington, VT 05201

    Own a piece of Bennington history! Alex Drysdale House, c. 1850. The grocery store (formerly 138 River Street) operated under the name "A. Drysdale & Son" and was built in 1876. Today this historic property is set up as a four-unit with great income potential. It currently houses three apartments: a freshly renovated four bedroom (used as an Airbnb), three bedroom, and efficiency, along with the

    Justine Curry Maple Leaf Realty

    200 Depot St, Bennington, VT 05201
  • /57

    $215,000

    • 3 Beds
    • 1 Bath
    • 1,416 Sq Ft

    100 Webb St, Bennington, VT 05201

    Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown!Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort.From the moment you arrive, you're greeted by the cobblestone

    Lindsey Martin Maple Leaf Realty

    100 Webb St, Bennington, VT 05201
  • /37

    $229,000

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    73 Woodford City Rd, Bennington, VT 05201

    Step into your woodland paradise! Nestled on 1.1 acres and bordered by a babbling brook and private pond, this lovingly maintained 3-bedroom, 1-bath home offers peace, privacy, and a strong connection to nature. Built by the current owner in 1982, the home has been well cared for over the years.A detached two-car garage with workshop space and a separate shed offer plenty of room for tools, toys,

    Abi Gregorio

    73 Woodford City Rd, Bennington, VT 05201
  • /42

    $1,950,000

    • 9 Beds
    • 7 Baths
    • 6,956 Sq Ft

    1086 West Rd, Bennington, VT 05201

    Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

    Chris DeFelice Four Seasons Sotheby's Int'l Realty

    1086 West Rd, Bennington, VT 05201
  • /35

    $264,900

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft

    115 Jefferson Ave, Bennington, VT 05201

    Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and

    Kelley Mccarthy Mahar McCarthy Real Estate

    115 Jefferson Ave, Bennington, VT 05201
  • /7

    $175,000

    • Land
    • 15 Acres
    • $11,298 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
  • /52

    $199,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    130 Morgan St, Bennington, VT 05201

    200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities.

    Dan Mason Perrott Realty

    130 Morgan St, Bennington, VT 05201
  • /47

    $299,900

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft

    120 Imperial Ave, Bennington, VT 05201

    Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

    Kelley Mccarthy Mahar McCarthy Real Estate

    120 Imperial Ave, Bennington, VT 05201
  • /39

    $297,500

    • 5 Beds
    • 2 Baths
    • 2,294 Sq Ft

    218 Union St, Bennington, VT 05201

    Charming Downtown Victorian - Income Opportunity Meets Timeless StyleTucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each

    Kelley Mccarthy Mahar McCarthy Real Estate

    218 Union St, Bennington, VT 05201
  • /30

    $1,250,000

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    77 Fuller Rd W, Bennington, VT 05201

    Experience the quintessential Vermont lifestyle at the historic Nickerson-Jewett farm. Only 5 minutes to Bennington attractions and amenities and 15 minutes to Williamstown, MA. This appealing country home is located on a town maintained dead-end road. Privately nestled on 134.46 acres of scenic beauty, the charming 4 bedroom, 2.5 bath mid nineteenth century farmstead includes a well-preserved

    Jason Saphire www.HomeZu.com

    77 Fuller Rd W, Bennington, VT 05201
  • /5

    $2,500,000

    • Land
    • 0.88 Acre
    • $2,840,909 per Acre

    113 Depot St, Bennington, VT 05201

    Mixed use development site in the heart of Downtown Bennington. .88 acre site with Zoning, Preservation and Stormwater approvals for a 60,000 sq ft mixed use building with planned commercial occupancy on the first floor and three stories of residential occupancy above - 60 units total with 12 units of workforce housing.

    Paul Carroccio TPW Real Estate

    113 Depot St, Bennington, VT 05201
  • /8

    $59,000

    • Land
    • 0.29 Acre
    • $203,448 per Acre

    420 Burgess Rd, Bennington, VT 05201

    Level building lot with town sewer and water at the edge of town.Possible owner financing.

    Dan Mason Perrott Realty

    420 Burgess Rd, Bennington, VT 05201
  • /2

    $49,900

    • Land
    • 11 Acres
    • $4,455 per Acre

    0 Mount Anthony Rd, Bennington, VT 05201

    A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont—11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds.Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building

    Kelley Mccarthy Mahar McCarthy Real Estate

    0 Mount Anthony Rd, Bennington, VT 05201
  • /2

    $850,000

    • 7,504 Sq Ft

    5 Hunt St, Bennington, VT 05201

    Historic structure on the Walloomsac River and close to the Northside Drive/Kocher Driver commercial core.

    Paul Carroccio TPW Real Estate

    5 Hunt St, Bennington, VT 05201
  • /45

    $795,000

    • Land
    • 80 Acres
    • $9,981 per Acre

    0 Rd, Bennington, VT 05201

    Take a look at an incredible development opportunity located in the heart of Bennington. These two adjacent parcels of land, one situated off Fillmore Street encompassing 31.19 acres and the other off Gore Road spanning 48.46 acres, together offer over 75 acres of prime, buildable terrain.Notably, the property is bordered by two existing housing developments to the east (East St, West St and

    Lilli West Maple Leaf Realty

    0 Rd, Bennington, VT 05201
  • /20

    $98,999 New Construction

    • 2 Beds
    • 2 Baths
    • 825 Sq Ft

    72 Ethans Way, Bennington, VT 05201

    Welcome to 72 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Lewis model manufactured home offers 2 bedrooms, 2 bathroom, and 825 sq. ft. (16 x 56 ft.) 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

    72 Ethans Way, Bennington, VT 05201
  • /25

    $98,999 New Construction

    • 2 Beds
    • 2 Baths
    • 825 Sq Ft

    86 Ethans Way Unit Lot 86E, Bennington, VT 05201

    Welcome to 78 86 Ethans Way, Lot 86E Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polo model manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. 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 energy-efficient

    Kate Barry EXP Realty

    86 Ethans Way Unit Lot 86E, Bennington, VT 05201
  • /23

    $89,499 New Construction

    • 2 Beds
    • 2 Baths
    • 746 Sq Ft

    92 Ethans Way, Bennington, VT 05201

    Welcome to 92 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polo model manufactured home offers 2 bedrooms, 1 bathroom, and 746 sq. ft. (14 x 56 ft.) 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

    92 Ethans Way, Bennington, VT 05201

Why Live in Bennington

Nestled within the Green Mountains of southwestern Vermont, Bennington is a town celebrated for its rich history, outdoor trails and skiing, as well as its historic buildings along Main Street. Dating back to 1749, Bennington holds a significant place in the state’s heritage as the first town chartered in Vermont. The Old Bennington Historic District is a window to the past, where the Bennington Monument and the Old First Church Cemetery teach new residents about times of old. Today, downtown is investing in a bandstand for summer concerts, a s ...

Frequently Asked Questions

What is the average home price in Bennington, VT?
Homes for sale in Bennington, VT have an average home price of $351,284.
How many homes have sold over the last 12 months in Bennington, VT?
96 homes have sold in Bennington, VT over the last 12 months.
What are the most popular zip codes in Bennington, VT?
The most popular zip codes in Bennington, VT include 01247, 05356, 05201, 01267 and 05363.
How much do you need to make to afford a house in Bennington?
The median home price in Bennington is $275,000. If you put a 20% down payment of $55,000 and had a 30-year fixed mortgage with an interest rate of 6.89%, your estimated principal and interest payment would be $1,450 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $62K a year to afford the median home price in Bennington.
How are the schools in Bennington, VT?
Bennington, VT has highly rated public and private schools. Some of the best schools in Bennington based on Niche Grades are Grace Christian School, Hoosick Falls Elementary School and Hoosick Falls Junior/Senior High School. Browse all the schools in Bennington, VT to learn more.

Home Trends in Bennington, VT

Housing Trends

Median Sale Price
$262,500
Median Single Family Sale Price
$270,000
Median 2 Bedroom Sale Price
$165,000
Average Price Per Sq Ft
$172
Number of Homes for Sale
15
Last 12 months Home Sales
96
Months of Supply
1.90
Median List Price
$275,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
5%
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