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    Litchfield County, CT Sports & Entertainment Properties for Sale

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    Historic Theater and Street-Front Retail
    Updated: Jun 22
    Historic Theater and Street-Front Retail

    27 Railroad Street, North Canaan, CT 06018

    $695,000
    10,383 sqft 0.24 AC lot
    Built in 1923, this three‑level entertainment venue includes a massive main theatre with soaring ceilings and flat tiered flooring.
    The theatre has structural seating for approximately 120 guests, with additional room to add seating.
    Two primary floors provide space for approximately 400 guests, plus separate, street‑front commercial retail units.
    Street‑facing marquee with neon lighting, along with a custom mural, vintage ticket booth, and concession stand inside.
    Comprehensive $1M+ restoration in the early 2000s restored original Art Deco details.
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    Colonial Theatre with Retail Front
    Updated: Jun 22
    Colonial Theatre with Retail Front

    25 + 27 Railroad Street, North Canaan, CT 06018

    $870,000
    10,383 sqft 0.42 AC lot
    Historic Colonial Theatre landmark built in 1923, with central air and public water and public sewer
    Three‑level entertainment venue with structural seating for approx. 120 guests in the main theatre and soaring ceilings
    Approximately 400 guests across two primary floors, plus a vintage ticket booth and concession stand
    Street‑front facade includes separate, high‑visibility commercial retail units
    Completed $1M+ restoration in the early 2000s, reviving original Art Deco details
    View details
    Indoor Sports Complex Facility
    Indoor Sports Complex Facility

    32 Still River Drive, New Milford, CT 06776

    $6,500,000
    42,000 sqft

    Air-conditioned indoor sports complex with turf field, multiple courts, concessions, and locker rooms.

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    Turn Any Listing Into an Investment Snapshot Owner equity, real caprate, demand score for every listing. Go To Analytics Center
    Colonial Theatre with Street-Front Retail
    Colonial Theatre with Street-Front Retail

    27 Railroad St, Canaan, CT 06018

    $695,000

    Historic, restored three-level theatre offers on-site entertainment space plus separate street-front commercial retail units.

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    Historic Theater with Retail Frontage
    Historic Theater with Retail Frontage

    25 + 27 Railroad St, Canaan, CT 06018

    $870,000

    Multi-level theater with street-front retail units and a landmark marquee in downtown North Canaan.

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    Turnkey Golf Cart Rental Business
    Turnkey Golf Cart Rental Business

    57 Watertown Rd, Morris, CT 06763

    $449,900

    Established golf cart business sells, services, and rents golf carts, with included vehicles, parts inventory, and operating assets.

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    Indoor Movie Theater Property
    Indoor Movie Theater Property

    27 & 37 North Main Street, Plymouth, CT 83455

    Contact for pricing
    3,350 sqft 0.25 AC lot

    Renovated indoor movie theater property includes adjacent parcels to the south and rear.

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    Single-Story Cinema with Mezzanine
    Single-Story Cinema with Mezzanine

    89 Farley Pl, Torrington, CT 06790

    Contact for pricing

    Single-story cinema facility with mezzanine level for digital projection equipment and long-term net lease structure.

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    Based on your search, we've compiled 30 Potential Opportunities for your consideration. Besides 8 Active listings in Litchfield County, CT, we suggest exploring several alternatives: similar 18 Off-Market properties to explore as potential leads, 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.

    Prime Commercial Land Opportunity
    Prime Commercial Land Opportunity

    3013 Route 22, Patterson, NY 12563

    $1,390,000
    40.72 AC lot

    40.72 acres of commercially zoned land on Route 22.

    View details
    Master Planned Development Land
    Master Planned Development Land

    South Road, Marlborough, CT 06447

    $8,250,000
    426.50 AC lot

    426.5-acre development site zoned multifamily, with prior approval for open space and an 18-hole golf course layout.

    View details
    Ossining Land with Hudson Views
    Ossining Land with Hudson Views

    Van Wyck Street, Ossining, NY

    $1,900,000
    5.92 AC lot

    5.92 acres in Ossining, NY, with Hudson River views.

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    Middletown Land with Recreational Amenities
    Middletown Land with Recreational Amenities

    422 M And M Road, Middletown, NY 10940

    $1,100,000
    18,000 sqft 40.60 AC lot

    40-acre property with pavilion, sports fields, and development potential.

    View details

    Off-Market Properties in Litchfield County, CT

    Consider similar Off-Market properties in Litchfield County, CT. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    27 Railroad St
    THEATER (MOVIE)

    27 Railroad St, Canaan, CT 06018

    Value Estimation by Request
    10,383 sqft 0.24 AC lot
    View details
    266 Main St
    BOWLING ALLEY

    266 Main St, Winsted, CT 06098-1642

    Value Estimation by Request
    8,582 sqft 0.35 AC lot
    View details
    89 Farley Pl
    THEATER (MOVIE)

    89 Farley Pl, Torrington, CT 06790-3201

    $560,000
    Estimated value
    15,334 sqft 1.10 AC lot
    View details
    300 Torringford St
    GOLF COURSE

    300 Torringford St, Winsted, CT 06098-6023

    Value Estimation by Request
    5,829 sqft 12.00 AC lot
    View details
    135 Main St
    THEATER (MOVIE)

    135 Main St, Watertown, CT 06779-1748

    Value Estimation by Request
    6,119 sqft 0.15 AC lot
    View details
    184 Wolcott Rd
    FISH CAMPS, GAME TARGET SHOOTING

    184 Wolcott Rd, Terryville, CT 06786

    Value Estimation by Request
    560 sqft 94.00 AC lot
    View details
    1231 Bantam Rd
    Specialty properties

    1231 Bantam Rd, Litchfield, CT 06750

    Value Estimation by Request
    1,200 sqft 28.50 AC lot
    View details
    68th E Main St
    THEATER (MOVIE)

    68th E Main St, Torrington, CT 06790-5484

    $805,000
    Estimated value
    29,961 sqft 1.35 AC lot
    View details
    246 Guernseytown Rd
    GOLF COURSE

    246 Guernseytown Rd, Watertown, CT 06795-1819

    Value Estimation by Request
    9,552 sqft 53.00 AC lot
    View details
    246 Guernseytown Rd
    GOLF COURSE

    246 Guernseytown Rd, Watertown, CT 06795-1819

    Value Estimation by Request
    4,320 sqft 0.46 AC lot
    View details
    246 Guernseytown Rd
    GOLF COURSE

    246 Guernseytown Rd, Watertown, CT 06795-1819

    Value Estimation by Request
    14,945 sqft 1.51 AC lot
    View details
    180 Watertown Rd
    BOWLING ALLEY

    180 Watertown Rd, Thomaston, CT 06787-1828

    $750,000
    Estimated value
    20,417 sqft 3.12 AC lot
    View details
    730 Old Northfield Rd
    FISH CAMPS, GAME TARGET SHOOTING

    730 Old Northfield Rd, Thomaston, CT 06787-1117

    Value Estimation by Request
    2,760 sqft 15.12 AC lot
    View details
    726 Old Northfield Rd
    FISH CAMPS, GAME TARGET SHOOTING

    726 Old Northfield Rd, Thomaston, CT 06787-1117

    Value Estimation by Request
    7.80 AC lot
    View details
    728 Old Northfield Rd
    FISH CAMPS, GAME TARGET SHOOTING

    728 Old Northfield Rd, Thomaston, CT 06787-1117

    Value Estimation by Request
    1.74 AC lot
    View details
    Torringford St
    GOLF COURSE

    Torringford St, Winchester, CT 06098

    Value Estimation by Request
    8.00 AC lot
    View details

    Litchfield County, CT Sports & Entertainment Properties Market Trends and Statistics

    Explore 26 sports & entertainment properties for sale in Litchfield County, CT, showcased through 8 active listings on our real estate platform. These investment opportunities span a total of 66,116 square feet of properties for sale, with an estimated market value of $10,079,900.

    Sale prices for sports & entertainment properties in Litchfield County, CT start at $449,900, averaging $1,679,983, and reaching up to $6,500,000 — 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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