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    Berkshire County, MA Bed & Breakfasts for Sale

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    Boston, MA Worcester, MA Springfield, MA
    Historic Bed & Breakfast Opportunity
    $1,200,000
    10,560 SF

    Historic Bed & Breakfast Opportunity

    74 Wendell Ave, Pittsfield, MA 1201

    Turnkey 9-unit bed & breakfast near downtown.

    • Turnkey historic 9‑unit bed & breakfast with strong income potential.
    • Nine unique guest suites, each with private baths and kitchenettes.
    • Prime location within walking distance to the downtown theater/business district.
    • Potential for a private one‑bedroom owner's unit in the basement.
    • Upgraded, high‑efficiency Viessman boiler and architectural radiators.
    Updated: Apr 10
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    Lee MA Bed & Breakfast
    $3,400,000
    11,945 SF

    Lee MA Bed & Breakfast

    615 Laurel St., Lee, MA 1238

    Bed & Breakfast with 14 bedrooms and lakefront access.

    • 530 feet of lakefront property
    • Exceptional bed & breakfast inn
    • Fourteen bedrooms, each a private sanctuary
    • Sixteen full bathrooms plus one half bathroom
    • Expansive 11,945 sq ft of living space
    Updated: Apr 25
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    Berkshire Lakefront Boutique Inn
    $3,400,000
    11,945 SF

    Berkshire Lakefront Boutique Inn

    Boutique Inn with 14 keys and expansion potential.

    615 Laurel St, Lee, MA 1238
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    Historic Great Barrington Retreat
    $675,000
    3,684 SF

    Historic Great Barrington Retreat

    Historic Berkshire retreat with potential for reimagining and inspired use.

    3 Lake Buel Rd, Great Barrington, MA 01230
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    Based on your search, we've compiled 8 Potential Opportunities for your consideration. Besides 4 Active listings in Berkshire County, MA, we suggest exploring several alternatives: plus 4 Land Listings that present a potential for development.

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Winchester Vacant Wooded Lot
    $33,750
    5.34 Acres

    Winchester Vacant Wooded Lot

    Vacant, wooded lot with high visibility in Winchester, NH.

    0 Ashuelot Main Street, Winchester, NH 03470
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    Commercial Land in Woodridge, NY
    $69,000
    0.46 Acres

    Commercial Land in Woodridge, NY

    Prime commercial land with utilities available in Woodridge, NY.

    *** Mountaindale Road, Fallsburg, NY 12733
    View details
    Cochecton Land on Route 17B
    $68,500
    2.00 Acres

    Cochecton Land on Route 17B

    Two acres in Hamlet District, suitable for commercial or residential.

    2.-1-32.7 State Route 17B, Cochecton, NY 12726
    View details
    Aquebogue Land with Development Potential
    $749,000
    1.17 Acres

    Aquebogue Land with Development Potential

    1.17 acre lot with residential and commercial possibilities.

    730 Main Road, Aquebogue, NY 11931
    View details

    Berkshire County, MA Bed & Breakfasts Investment Opportunities Market Analysis

    Explore 4 bed & breakfasts for sale in Berkshire County, MA, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 26,189 square feet of properties for sale, with an estimated market value of $5,275,000.

    Sale prices for inns in Berkshire County, MA start at $675,000, averaging $1,758,333, and reaching up to $3,400,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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