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For sale
    • Price cut: $20K (10/30)
    $499,900

    33 Machine Shop Hill Road, Windham, CT 06266

    4beds
    2,548sqft
    : 
    $3,448/mo
    Get pre-qualified
    Single Family Residence
    Built in 1850
    0.42 Acres Lot
    $-- Zestimate®
    $196/sqft
    $-- HOA

    What's special

    Spacious deckOversized heated garageTwo detached garagesOwn laundry areaDedicated home officeComfortable finished living spaceAdditional first-floor living space
    Looking for a home with a little extra room to spread out? This beautifully renovated single-family home offers the perfect combination of modern updates, comfort, and flexibility! One of its standout features is the additional first-floor living space, offering added privacy and versatility for a variety of lifestyle needs. This separate area features comfortable finished living space, a full bathroom, and its own laundry area, providing convenience and functionality. The bright, open-concept kitchen, dining, and living areas create a welcoming atmosphere perfect for everyday living and entertaining. A dedicated home office provides additional flexibility, while convenient main-level laundry adds even more functionality. Extensively remodeled throughout, this move-in-ready home showcases beautiful modern updates, including a new roof and new furnace, offering added value and peace of mind. Step outside to enjoy the spacious deck, perfect for relaxing or entertaining. The property also features two detached garages, including an oversized heated garage, offering exceptional space for vehicles, storage, a workshop, or hobbies. With its beautifully updated interior, flexible floor plan, additional first-floor living space, and impressive garage accommodations, this property offers more than meets the eye! Enjoy the comfort of single-family living with a little extra space to make your own. Schedule your private showing today!
    22 days
    445
    37

    Zillow last checked:

    Listing updated:

    Listed by:

    Michele Geragotelis (860)917-6090,

    RE/MAX Bell Park Realty 860-774-7600

    Source: Smart MLS,MLS#: 24215433MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Remodeled, Ceiling Fan(s), Walk-In Closet(s)
      • Level: Upper
      • Area: 192 Square Feet
      • Dimensions: 12 x 16
      Bedroom
      • Features: Remodeled, Ceiling Fan(s), Laundry Hookup, Walk-In Closet(s)
      • Level: Main
      • Area: 156 Square Feet
      • Dimensions: 12 x 13
      Bedroom
      • Features: Remodeled, Ceiling Fan(s), Walk-In Closet(s)
      • Level: Upper
      • Area: 247 Square Feet
      • Dimensions: 19 x 13
      Bedroom
      • Features: Remodeled, Ceiling Fan(s)
      • Level: Upper
      • Area: 132 Square Feet
      • Dimensions: 12 x 11
      Primary bathroom
      • Features: Remodeled, Double-Sink, Stall Shower, Tile Floor
      • Level: Upper
      Bathroom
      • Features: Remodeled, Laundry Hookup, Tile Floor
      • Level: Main
      Bathroom
      • Features: Remodeled, Granite Counters, Double-Sink, Stall Shower, Tile Floor
      • Level: Main
      Bathroom
      • Features: Double-Sink, Tub w/Shower, Tile Floor
      • Level: Upper
      Dining room
      • Features: Remodeled, Balcony/Deck, Beamed Ceilings, Tile Floor
      • Level: Main
      • Area: 182 Square Feet
      • Dimensions: 13 x 14
      Kitchen
      • Features: Remodeled, Breakfast Bar, Granite Counters, Tile Floor
      • Level: Main
      • Area: 156 Square Feet
      • Dimensions: 13 x 12
      Kitchen
      • Features: Remodeled, Kitchen Island
      • Level: Main
      • Area: 132 Square Feet
      • Dimensions: 11 x 12
      Living room
      • Features: Remodeled, Beamed Ceilings
      • Level: Main
      • Area: 216 Square Feet
      • Dimensions: 12 x 18
      Living room
      • Features: Remodeled
      • Level: Main
      • Area: 104 Square Feet
      • Dimensions: 8 x 13
      Office
      • Features: Remodeled
      • Level: Main
      • Area: 132 Square Feet
      • Dimensions: 12 x 11
      Heating
      • Forced Air, Oil
      Cooling
      • Ceiling Fan(s)
      Appliances
      • Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Water Heater
      • Laundry: Main Level
      Features
      • Open Floorplan, In-Law Floorplan
      • Basement: Full,Unfinished
      • Attic: Storage,Floored,Walk-up
      • Has fireplace: No
      Interior area
      • Total structure area: 2,548
      • Total interior livable area: 2,548 sqft
      • Finished area above ground: 2,548

      Property

      Parking
      • Total spaces: 3
      • Parking features: Detached
      • Garage spaces: 3
      Features
      • Patio & porch: Porch, Deck
      • Exterior features: Rain Gutters, Lighting, Stone Wall
      Lot
      • Size: 0.42 Acres
      • Features: Few Trees, Dry, Rolling Slope
      Details
      • Parcel number: 2290405
      • Zoning: RVD

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Stone
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1850
      Details
      • Warranty included: Yes

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public

      Community & HOA

      Community
      • Features: Library, Medical Facilities, Park, Private School(s), Pool, Putting Green, Shopping/Mall
      HOA
      • Has HOA: No
      Location
      • Region: South Windham

      Financial & listing details

      • Price per square foot: $196/sqft
      • Tax assessed value: $166,280
      • Annual tax amount: $4,963
      • Date on market: 10/19/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        10/30/2026Price change$499,900-3.8%$196/sqft
        Source: Smart MLS #24215433 Report a problem
        10/19/2026Listed for sale$519,900-1%$204/sqft
        Source: Smart MLS #24215433 Report a problem
        10/14/2026Listing removed$524,900$206/sqft
        Source: Smart MLS #24200058 Report a problem
        9/28/2026Price change$524,900-1.9%$206/sqft
        Source: Smart MLS #24200058 Report a problem
        9/22/2026Price change$534,900-2.7%$210/sqft
        Source: Smart MLS #24200058 Report a problem
        8/21/2026Listed for sale$549,900+243.7%$216/sqft
        Source: Smart MLS #24200058 Report a problem
        12/24/2025Sold$160,000-5.9%$63/sqft
        Source: Smart MLS #24109877 Report a problem
        12/2/2025Pending sale$170,000$67/sqft
        Source: Smart MLS #24109877 Report a problem
        11/6/2025Price change$170,000-12.8%$67/sqft
        Source: Smart MLS #24109877 Report a problem
        9/13/2025Pending sale$195,000$77/sqft
        Source: Smart MLS #24109877 Report a problem
        9/8/2025Price change$195,000-17.9%$77/sqft
        Source: Smart MLS #24109877 Report a problem
        7/10/2025Listed for sale$237,500+84.1%$93/sqft
        Source: Smart MLS #24109877 Report a problem
        9/29/2014Listing removed$129,000$51/sqft
        Source: Hammett Real Estate #G680457 Report a problem
        5/27/2014Price change$129,000-7.8%$51/sqft
        Source: HAMMETT REAL ESTATE #G680457 Report a problem
        4/25/2014Listed for sale$139,900+8.4%$55/sqft
        Source: HAMMETT REAL ESTATE #G680457 Report a problem
        8/16/2013Listing removed$129,000$51/sqft
        Source: HAMMETT REAL ESTATE #G612292 Report a problem
        5/5/2013Listed for sale$129,000-13.9%$51/sqft
        Source: HAMMETT REAL ESTATE #G612292 Report a problem
        1/27/2012Listed for sale$149,900$59/sqft
        Source: HAMMETT REAL ESTATE #G612292 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,963 -0.1%$166,280
        2024$4,970 +20.5%$166,280 +56.5%
        2023$4,124 +2.6%$106,260
        2022$4,018 -4.1%$106,260
        2021$4,188 +1.3%$106,260
        2020$4,134 +1.3%$106,260
        2019$4,080 +9.2%$106,260 +8.6%
        2017$3,737 +5.9%$97,830
        2015$3,531 +11.3%$97,830
        2014$3,171 -23%$97,830 -30.9%
        2013$4,116 -3.9%$141,630
        2012$4,281 +6.2%$141,630
        2011$4,032 +0.4%$141,630
        2010$4,017 +6.4%$141,630
        2009$3,777 +6.9%$141,630
        2008$3,532 -5.9%$141,630
        2007$3,752 +3.6%$141,630
        2006$3,623 +18.7%$141,630 +36.9%
        2005$3,051 +0.3%$103,460
        2004$3,041 +27.1%$103,460 +22.4%
        2001$2,393 $84,539
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 06266

        Getting around

        12 / 100
        Car-Dependent
        7 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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