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    Middlesex County, CT Duplexes for Sale

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    Duplex with Covered Front Porch
    Updated: Jul 23
    Duplex with Covered Front Porch

    242 Main Street, Durham, CT 06422

    $539,000
    2,339 sqft 0.60 AC lot
    Built in 1820 duplex on a 0.6‑acre level yard
    Configured as two primary units plus an additional accessory living area
    Front unit with covered porch, original wood flooring, fireplace
    Renovated rear apartments with one bedroom each and custom kitchens with stainless steel appliances
    Energy‑efficient windows plus walk‑up attic and basement storage
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    Duplex with Mixed-Use Flex Space
    Updated: Dec 9, 2025
    Duplex with Mixed-Use Flex Space

    33 Deep River Road, Essex, CT 06409

    $829,000
    7,309 sqft 0.74 AC lot
    Two existing apartments within mixed‑use/flex space
    Historic building built in 1830
    0.74‑acre level lot with gravel parking lot
    7,309 SF property size
    Central air plus window unit(s) and baseboard heat
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    Duplex with Office/Flex Spaces
    Duplex with Office/Flex Spaces

    33 Deep River Road, Essex, CT 06409

    $829,000
    7,309 sqft 0.74 AC lot

    Zoned C, this property includes two apartments plus multiple office/flex spaces on a 0.74-acre lot with gravel parking.

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    Renovated Historic Multifamily Duplex
    Renovated Historic Multifamily Duplex

    242 Main Street, Durham, CT 06422

    $539,000
    2,339 sqft

    Well-maintained multifamily home with renovated interiors, multiple residential units, and off-street parking.

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    Two-Unit Duplex with Garage
    Two-Unit Duplex with Garage

    46 Main Street, Essex, CT 06409

    $449,999
    1,252 sqft 0.67 AC lot

    Two-unit duplex on 0.67 acres with private entrances, garage parking, and washer/dryer hookups in the basement.

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    Fire-Damaged Two-Family Duplex
    Fire-Damaged Two-Family Duplex

    18 Portland Street, Middletown, CT 06457

    $90,000
    1,558 sqft 0.08 AC lot

    Two-family duplex on a level lot offered strictly as-is with public water and public sewer access.

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    Historic Multi-Family Home
    Historic Multi-Family Home

    13 Platt Lane, Deep River, CT 06417

    $525,000
    2,033 sqft

    Multi-family property built in 1840, offering a spacious yard and flexible investment or owner-occupied use.

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    Two-Unit Residential Income Property
    Two-Unit Residential Income Property

    74 Johnson Street, Middletown, CT 06457

    $375,000
    2,848 sqft

    Two separate residential units each feature in-unit laundry and fully applianced kitchens, with ample off-street parking and yard space.

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    8-Bedroom Duplex with Attics
    8-Bedroom Duplex with Attics

    37-39 Loveland Street, Middletown, CT 06457

    $399,900
    2,916 sqft

    Duplex offers two units with separate utilities and finished attic space for additional bedrooms.

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    Two-Dwelling Residential Income Property
    Two-Dwelling Residential Income Property

    11 Phelps Road, East Haddam, CT 06423

    $749,000
    2,648 sqft

    Two residences on one parcel, including a historic Mill House and a restored chapel ADU with updated mechanicals.

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    Middletown Income Property Package
    Middletown Income Property Package

    28 Portland Street, Middletown, CT 06457

    Contact for pricing
    5,176 sqft 0.45 AC lot

    Four income-producing units, workshop, and vacant land parcels.

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    Two-Family Home with Three-Season Porch
    Two-Family Home with Three-Season Porch

    22 West Street, Cromwell, CT 06416

    $425,000
    1,872 sqft

    Two separate units feature in-unit laundry, a three-season porch, and a full unfinished basement with additional space.

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    Historic Westbrook Duplex Near Beach
    Historic Westbrook Duplex Near Beach

    29 Salt Island Road, Westbrook, CT 06498

    $375,000
    1,665 sqft

    Charming two-family property near Middle Beach with income potential.

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    As-Is Fire-Damaged Duplex
    As-Is Fire-Damaged Duplex

    18 Portland Street, Middletown, CT 06457

    $90,000
    1,558 sqft

    Two-family property sold as-is with fire damage, located on a level lot with public water and public sewer access.

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    Well-Maintained Brick Two-Family Home
    Well-Maintained Brick Two-Family Home

    7 Olson Avenue, Cromwell, CT 06416

    $400,000
    2,724 sqft

    Brick two-family cape with separate electric meters, individual A/C units, and a partially finished basement with added kitchen and bath.

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    Two-Unit Residential Income Property
    Two-Unit Residential Income Property

    2 Nooks Hill Rd, Cromwell, CT 06416

    $250,000

    Spacious 2-family home with six bedrooms and two full bathrooms, with both units delivered vacant at closing.

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    Two-Family Duplex Investment
    Two-Family Duplex Investment

    12 Fairview St, Portland, CT 06480

    $449,000

    For sale two-family duplex in Portland producing rental income and offering convenient commuter access.

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    Centerbrook Two-Unit Income Property
    Centerbrook Two-Unit Income Property

    46 Main St, Essex, CT 06409

    $469,900

    Well-maintained two-unit property in the heart of Centerbrook.

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    Middletown Duplex in Desirable Location
    Middletown Duplex in Desirable Location

    58 Durant Ter, Middletown, CT 06457

    $369,900
    0.15 AC lot

    Well-maintained duplex near downtown, ideal for investors or owner-occupants.

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    Two-Family Residential Investment
    Two-Family Residential Investment

    20 Maple St, Middletown, CT 06457

    $174,900

    Two 2BR units with recent roof, gutters, updated windows, and covered porches, offered as-is to cash buyers.

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    Two-Family Residential Income Property
    Two-Family Residential Income Property

    22 W High St, East Hampton, CT 06424

    $375,000

    Victorian two-family with separate entrances, high ceilings, fireplaces, and shared front foyer on an in-town level lot.

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    Two-Family Residential Income
    Two-Family Residential Income

    10-12 Glover Pl, Middletown, CT 06457

    $349,900

    Two-unit property features 3 bedrooms on each level with separate utilities and central air in both units.

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    Two-Family Residential Income Property
    Two-Family Residential Income Property

    118 Grove St, Middletown, CT 06457

    $359,900

    Two separate units offer natural gas, laundry in each, and separate utilities with multiple electric panels.

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    Mixed-Use Commercial Property Opportunity
    Mixed-Use Commercial Property Opportunity

    369 Boston Post Rd, Old Saybrook, CT 06475

    Contact for pricing
    2,700 sqft 0.61 AC lot

    Mixed-use property near Old Saybrook center with income potential.

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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 24 Active Listings in Middlesex County, CT

    Middlesex County, CT Duplexes Market Trends and Statistics

    Explore 24 duplexes for sale in Middlesex County, CT, showcased through 24 active listings on our real estate platform. These investment opportunities span a total of 48,246 square feet of properties for sale, with an estimated market value of $9,413,399.

    Sale prices for duplexes in Middlesex County, CT start at $90,000, averaging $427,881, and reaching up to $829,000 — 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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