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    Middlesex County, CT Bed & Breakfasts for Sale

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    Waterbury, CT Hartford, CT Bridgeport, CT
    Historic Mixed-Use Property For Sale
    $849,900
    2,616 SF

    Historic Mixed-Use Property For Sale

    323 Main Street, Old Saybrook, CT 6475

    Antique property in Old Saybrook with retail and residential spaces.

    • Completely restored antique property (circa 1790) with modern conveniences.
    • Multi‑use investment property with retail space equipped for restaurant/cafe and 3 second‑floor units, each with a full, remodeled bath.
    • Located in the historic district of Old Saybrook, Connecticut.
    • Walkable to downtown restaurants, cafes, boutique shops, and the Katherine Hepburn Performing Arts Center.
    • Close proximity to public beaches and Saybrook Point Resort & Marina.
    Updated: Mar 19
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    Restored Colonial with Modern Comfort
    $1,199,999
    4,982 SF

    Restored Colonial with Modern Comfort

    209 Main Street, Deep River, CT 06417

    Meticulously restored 1854 Colonial in Deep River, Connecticut.

    • Meticulously restored 1854 Colonial blending historic charm with modern comfort.
    • Seven bedrooms, each with its own private bath.
    • Six fireplaces, including a 12' natural stone Rumford.
    • Recent kitchen addition provides true in‑law apartment flexibility.
    • Third‑floor suite with wood‑burning fireplace offers serene separation.
    Updated: Nov 18, 2025
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    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 Active listings in Middlesex County, CT, 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.

    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
    Calverton Land with Permitted Uses
    $550,000
    4.00 Acres

    Calverton Land with Permitted Uses

    4 acres of land with multiple permitted uses in Calverton.

    (Left of 2080 River Road) River Road, Calverton, NY 11933
    View details
    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
    View details
    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

    Middlesex County, CT Bed & Breakfasts Investment Opportunities Market Analysis

    Explore 2 bed & breakfasts for sale in Middlesex County, CT on our real estate platform. These investment opportunities span a total of 7,598 square feet of properties for sale, with an estimated market value of $2,049,899.

    Sale prices for inns in Middlesex County, CT start at $849,900, averaging $1,024,949, and reaching up to $1,199,999 — 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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