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    Winchester, CT Apartment Buildings for Sale

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    New Hartford, CT Canton, CT Torrington, CT
    Winsted Multifamily Investment Opportunity
    $579,000
    Winsted Multifamily Investment Opportunity

    150 Oak St, Winchester, CT 6098

    Charming 5-unit apartment building in residential neighborhood. Fully rented.
    • Fully rented 5‑family apartment home in a desirable residential neighborhood.
    • Recent major upgrades including new roof, 4 hot water heaters, and 3 furnaces (2021‑2023).
    • Features original 1920's charm with original woodwork, high ceilings, and some hardwood floors.
    • Includes a 4‑bay detached garage, with rental income potential.
    • Convenient location: walking distance to Northwestern CT Community College and Downtown Winsted.
    Updated: Apr 21
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    Mixed-Use Building with Income Potential
    $540,000
    7,405 SF
    Mixed-Use Building with Income Potential

    45 Elm Street, Winchester, CT 6098

    Seven-unit brick building with residential and commercial spaces for sale.
    • Solid 7‑unit brick building with 5 residential apartments and 2 commercial office spaces.
    • Potential to convert office spaces into additional residential units (with approvals).
    • Spacious rear lot provides ample off‑street parking for tenants.
    • Convenient location near Routes 8 and 44, shopping, dining, and Northwestern Connecticut Community College.
    • Ideal for investors seeking reliable cash flow or developers exploring expansion opportunities.
    Updated: Oct 14, 2025
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    Restaurant and Apartments in Winchester
    $750,000
    5,389 SF
    Restaurant and Apartments in Winchester

    Turnkey restaurant with apartments in high-traffic Litchfield County location.

    436 Main Street, Winchester, CT 6098

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    Based on your search, we've compiled 11 Potential Opportunities for your consideration. Besides 3 Active listings in Winchester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 4 Land Listings that present a potential for development.

    Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Bristol Multifamily Portfolio For Sale
    $2,750,000
    2,687 SF
    Bristol Multifamily Portfolio For Sale

    Five multifamily properties with 22 units in Bristol, Connecticut.

    29 Landry Street, Bristol, CT 06010

    View details
    Turnkey Income Property in Torrington
    $975,000
    5,755 SF
    Turnkey Income Property in Torrington

    Fully updated, income-producing 5-unit property with separate deeded lot.

    243 N Elm Street, Torrington, CT 06790

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    Gothic Church and School Conversion
    $595,000
    21,808 SF
    Gothic Church and School Conversion

    Historic church plus 1960s school on a corner lot, with approved exception to convert the school to apartments.

    85 Pulaski Street, Torrington, CT 6790

    View details
    Multifamily Investment Opportunity in Bristol
    $1,264,000
    0.25 Acres
    Multifamily Investment Opportunity in Bristol

    10-unit multifamily property in Bristol, CT with upside potential.

    7 Upson St, Bristol, CT 6010

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    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.

    Brooklyn Two-Family Home with Development Potential
    $1,888,888
    2,660 SF
    Brooklyn Two-Family Home with Development Potential

    Two-family home on a large lot with significant development potential.

    69 Martense Street, Brooklyn, NY 11226

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    Land Near Shepherd University
    $650,000
    3.70 Acres
    Land Near Shepherd University

    Prime land near Shepherd University with development potential.

    8285 MARTINSBURG Pike, Shepherdstown, WV 25443

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    Central Business Zoned Development Land
    $250,000
    0.23 Acres
    Central Business Zoned Development Land

    Central Business zoned parcel with plans for a three-story mixed-use building and 15 parking spaces.

    107 HOWARD Street, La Plata, MD 20646

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    Multifamily Development Opportunity in Charlotte
    $559,700
    0.47 Acres
    Multifamily Development Opportunity in Charlotte

    Prime 0.47-acre parcel zoned for multifamily development near UNC Charlotte.

    4312 Tantilla Circle, Charlotte, NC 28215

    View details

    Winchester, CT Apartment Buildings Investment Opportunities Market Analysis

    Explore 3 apartment buildings for sale in Winchester, CT, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 12,794 square feet of properties for sale, with an estimated market value of $1,290,000.

    Sale prices for two-family homes in Winchester, CT start at $540,000, averaging $645,000, and reaching up to $750,000 — 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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    Demographics Overview

    Population 14K
    Population Growth (5Y) -2.6%
    Median Household Income $85,212
    College Educated 77.5%

    High-Yield Neighborhoods for Investment

    Identify Winchester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

    Neighborhood Average Price
    Winsted - 06098 $623K

    Listings Trend

    New vs delisted commercial listings in Litchfield County

    New Delisted

    Total CRE Inventory on Market (SF)

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