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    Middlesex County, CT Duplexes for Sale

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    Seven-Unit Apartment Buildings
    Updated: Sep 2
    Seven-Unit Apartment Buildings

    23 Plains Road, East Haddam, CT 06469

    $895,000
    5,444 sqft 0.88 AC lot
    Two apartment buildings totaling 7 units on one 0.88‑acre parcel
    5,444 square feet of total property size
    Five‑unit Victorian building with 1 bd/1 bth apartments
    Two‑family duplex with a 2 bedroom unit on each floor
    New oil tanks and boilers; updated electrical and plumbing
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    Duplex with Separate Living Suite
    Updated: Sep 26
    Duplex with Separate Living Suite

    9 Ingham Hill Road, Essex, CT 06426

    $1,150,000
    3,308 sqft 1.40 AC lot
    3,308‑square‑foot duplex on 1.4 acres
    Main colonial dates to 1848; first‑floor wing added in 1974
    Separate living area connected to the main residence by a breezeway
    In‑ground gunite pool, two patio areas, and covered front porch
    Two‑car garage at the end of the addition
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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

    Separate apartments offer private entrances, kitchens, full baths, outdoor space, and basement laundry hookups.

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    Historic Duplex with Pool
    Historic Duplex with Pool

    9 Ingham Hill Road, Essex, CT 06426

    $1,150,000
    3,308 sqft 1.40 AC lot

    Two connected living areas provide separate kitchens and private bedroom suites, with a breezeway linking the residences.

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    Two-Unit Duplex with Separate Utilities
    Two-Unit Duplex with Separate Utilities

    61-63 Clark Hill Road, East Hampton, CT 06424

    $424,900
    2,484 sqft 1.38 AC lot

    Both residences include in-unit laundry, a kitchen with dining area, and access to the backyard.

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    Side-by-Side Duplex
    Side-by-Side Duplex

    18 Portland Street, Middletown, CT 06457

    $75,000
    1,558 sqft 0.08 AC lot

    Fire-damaged two-family property on a level lot with public water and sewer.

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    Duplex with Detached Garage
    Duplex with Detached Garage

    149 Spring Street, Middletown, CT 06457

    $524,900
    3,401 sqft 0.33 AC lot

    A finished lower level adds a second kitchen, full bath, and laundry area to the two-unit residence.

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    Two-Story Duplex with Acreage
    Two-Story Duplex with Acreage

    69-71 Stage Harbor Road, Marlborough, CT 06447

    $539,900
    1,120 sqft

    Two mirrored residences offer private patios, outdoor storage, and landscaped grounds for shared or separate household use.

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    Medical Office Space in Colonial Home
    Medical Office Space in Colonial Home

    1721 Saybrook Road, Haddam, CT 06438

    $655,000
    3,000 sqft

    Former veterinary clinic with multiple rooms, plumbing, basement access, and a whole-house automatic generator.

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    Duplex with Separate Driveways
    Duplex with Separate Driveways

    108 High Street, Middletown, CT 06457

    $399,900
    2,584 sqft

    A vacant first-floor residence is paired with a tenant-occupied upper unit, providing two distinct occupancy options.

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    Two-Family Duplex
    Two-Family Duplex

    64 Summer Street, Portland, CT 06480

    $319,900
    2,478 sqft

    Two separate living units offer flexibility for rental occupancy or multi-generational use.

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    Historic Multi-Family Home
    Historic Multi-Family Home

    13 Platt Ln, Deep River, CT 06417

    $499,000
    2,033 sqft

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

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

    46 Main Street, Essex, CT 06409

    $449,999
    1,252 sqft

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

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    Waterfront Duplex with Garage
    Waterfront Duplex with Garage

    157 Baileyville Road, Middlefield, CT 06455

    $699,900
    1,871 sqft

    Updated two-family property with lake views, balconies, a private courtyard, and a separate carriage house above a four-car garage.

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    Two-Unit Duplex with Walk-Up Attic
    Two-Unit Duplex with Walk-Up Attic

    219 Pearl, Middletown, CT 06457

    $274,900
    1,700 sqft

    Two apartments occupy separate floors, with off-street parking and a screened porch serving the upper unit.

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    Duplex with Separate Utilities
    Duplex with Separate Utilities

    61-63 Clark Hill Rd, East Hampton, CT 06424

    $424,900
    2,484 sqft

    Both residences include in-unit laundry, kitchen and dining areas, living rooms, and backyard access.

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    Two-Unit Duplex with Walk-Up Attic
    Two-Unit Duplex with Walk-Up Attic

    42 Grand Street, Middletown, CT 06457

    $369,900
    2,442 sqft

    Both apartments offer three bedrooms, with updated kitchens and full baths in the upper unit.

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    Duplex with Garage Apartment
    Duplex with Garage Apartment

    14 Casper, Middletown, CT 06457

    $365,000
    2,225 sqft

    A partially finished basement and gas forced-air heating add practical features to this two-unit residential property.

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    Character-Filled Duplex with Separate Yards
    Character-Filled Duplex with Separate Yards

    84-86 Spring St, Chester, CT 06412

    $579,900

    Two distinct residences with updated major systems, private outdoor areas, and flexible owner-occupant or rental use.

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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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    Three-Bedroom Duplex Apartment
    Three-Bedroom Duplex Apartment

    71 Prospect Street, Middletown, CT 06457

    Contact for pricing

    Upper-level duplex residence with hardwood flooring, stainless steel appliances, backyard access, and off-street parking.

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    Central Connecticut Two-Family Home
    Central Connecticut Two-Family Home

    31 Burr Ave, Middletown, CT 06457

    $330,000

    Two-unit property near downtown Middletown and Connecticut River.

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

    18 Portland Street, Middletown, CT 06457

    Contact for pricing

    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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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 23 Active Listings in Middlesex County, CT

    Middlesex County, CT Duplexes Market Trends and Statistics

    Explore 23 duplexes for sale in Middlesex County, CT, showcased through 23 active listings on our real estate platform. These investment opportunities span a total of 43,944 square feet of properties for sale, with an estimated market value of $10,947,898.

    Sale prices for two-family homes in Middlesex County, CT start at $75,000, averaging $521,328, and reaching up to $1,150,000 — 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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    Featured Middlesex County Real Estate Agencies

    Realmo connects you with licensed Middlesex County CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Cavanaugh & Company, LLC
    98 Washington Street Middletown, CT 06457
    Phone: (860) 346-8900
    www.cavanaughandcompany.com
    RE/MAX VALLEY SHORE
    103 Main Street Fenwick, CT 06475
    Phone: (860) 388-1228
    Silva-Williams, Inc. dba Sterling, Realtors
    27 Pleasant Street Middletown, CT 06457
    Phone: (860) 343-3820
    www.sterling-realtors.com
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