11

Bennington, VT Homes for Sale with Acreage

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  • 93 Russett Dr, Bennington, VT 05201
    93 Russett Dr, Bennington, VT 05201
    93 Russett Dr, Bennington, VT 05201
    /35

    $379,900

    • 4 Beds
    • 2.5 Baths
    • 2,530 Sq Ft

    93 Russett Dr, Bennington, VT 05201

    Welcome to this charming mid-century home set on 1.27 acres, offering 4 bedrooms and 3 bathrooms. This property blends character, functionality, and unique design throughout.At the heart of the home, a beautiful open concept kitchen and living area creates the perfect space for gathering and entertaining. A stunning fireplace anchors the room, offering warmth and ambiance whether you’re

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 416-3661

    93 Russett Dr, Bennington, VT 05201
  • 399 Bard Rd, Bennington, VT 05201
    399 Bard Rd, Bennington, VT 05201
    399 Bard Rd, Bennington, VT 05201
    /60

    $220,000

    • Land
    • 54 Acres
    • $4,074 per Acre

    399 Bard Rd, Bennington, VT 05201

    Escape to your own private sanctuary on this sprawling 54+/- acre wooded retreat in beautiful Bennington, VT. Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond situated entirely within its southeastern boundary, perfect as a future homestead centerpiece. Enjoy easy access via a paved, town-maintained road leading to level

    Curtis Trousdale Preferred Properties

    399 Bard Rd, Bennington, VT 05201
  • 80 Crossover Rd, Bennington, VT 05201
    80 Crossover Rd, Bennington, VT 05201
    80 Crossover Rd, Bennington, VT 05201
    /17

    $65,000

    • Land
    • 5.6 Acres
    • $11,607 per Acre

    80 Crossover Rd, Bennington, VT 05201

    This 5.6-acre lot is ideally situated at the edge of town, offering a peaceful retreat surrounded by nature. Furnace Brook winds through the backside of the property, providing a soothing sound that lulls you to sleep each night. Observe the abundant wildlife as they visit the stream with the Mountain view as the backdrop, this location is perfect for building your Vermont dream home.

    Dan Mason Perrott Realty

    80 Crossover Rd, Bennington, VT 05201
  • 2041 East Rd, Bennington, VT 05201
    2041 East Rd, Bennington, VT 05201
    2041 East Rd, 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.

    Dan Mason Perrott Realty

    2041 East Rd, Bennington, VT 05201
  • 16 West Rd, Bennington, VT 05201
    16 West Rd, Bennington, VT 05201
    16 West Rd, Bennington, VT 05201
    /58

    $1,495,000

    • 7 Beds
    • 5.5 Baths
    • 6,392 Sq Ft

    16 West Rd, Bennington, VT 05201

    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

    Kelley Mccarthy Mahar McCarthy Real Estate

    16 West Rd, Bennington, VT 05201
  • 1086 West Rd, Bennington, VT 05201
    1086 West Rd, Bennington, VT 05201
    1086 West Rd, Bennington, VT 05201
    /58

    $1,950,000

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

    1086 West Rd, Bennington, VT 05201

    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,

    Kelley Mccarthy Mahar McCarthy Real Estate

    1086 West Rd, Bennington, VT 05201
  • 38 Oak Ridge Ln, Bennington, VT 05201
    38 Oak Ridge Ln, Bennington, VT 05201
    38 Oak Ridge Ln, Bennington, VT 05201
    /39

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    38 Oak Ridge Ln, Bennington, VT 05201

    Convenient one-level living meets modern style and design in this beautifully crafted ranch home, situated on a spacious 1.4-acre lot within a newer, private four-home subdivision. Relax on the impressive 52-foot farmer’s porch—perfect for enjoying cool summer breezes, stunning sunsets, entertaining guests, or simply taking in the expansive yard and thoughtfully designed plantings. Inside the

    Matt Waddington Hoffman Real Estate

    38 Oak Ridge Ln, Bennington, VT 05201
  • 720 N Branch St, Bennington, VT 05201
    720 N Branch St, Bennington, VT 05201
    720 N Branch St, Bennington, VT 05201
    /10

    $1,950,000

    • Land
    • 7 Acres
    • $278,571 per Acre

    720 N Branch St, Bennington, VT 05201

    Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street. The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit on the

    Paul Carroccio TPW Real Estate

    720 N Branch St, Bennington, VT 05201
  • 00 Silk Rd, Bennington, VT 05201
    00 Silk Rd, Bennington, VT 05201
    00 Silk Rd, Bennington, VT 05201
    /7

    $175,000

    • Land
    • 15.49 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
  • 301 Northside Dr, Bennington, VT 05201
    301 Northside Dr, 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
  • 682 Fox Hill Rd, Bennington, VT 05201
    682 Fox Hill Rd, Bennington, VT 05201
    682 Fox Hill Rd, Bennington, VT 05201
    /47

    $625,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft

    682 Fox Hill Rd, Bennington, VT 05201

    Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct access

    Jenifer Prouty Hoffman Hoffman Real Estate

    682 Fox Hill Rd, Bennington, VT 05201
Vermont Bennington County Bennington

Homes for Sale with Acreage in Bennington, VT

Home Trends in Bennington, VT

On average, homes in Bennington, VT sell after 53 days on the market compared to the national average of 55 days. The median sale price for homes in Bennington, VT over the last 12 months is $258,000, down 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$258,000
Median Single Family Sale Price
$275,000
Median Townhouse Sale Price
$199,000
Median 2 Bedroom Sale Price
$164,950
Median 1 Bedroom Sale Price
$20,000
Average Price Per Sq Ft
$195
Number of Homes for Sale
17
Last 12 months Home Sales
109
Months of Supply
1.90
Median List Price
$275,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-1%
How to Buy a Home How to Finance a Home How to Sell a Home

In Bennington, there are currently 11 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Bennington, VT offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Bennington and discover the potential and freedom that comes with owning your own piece of property.

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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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