Skip main navigation
For sale
    • $549,900

    33 Machine Shop Hill Road, Windham, CT 06266

    4beds
    2,548sqft
    : 
    $3,894/mo
    Get pre-qualified
    Single Family Residence
    Built in 1850
    0.42 Acres Lot
    $540,900 Zestimate®
    $216/sqft
    $-- HOA

    What's special

    Dedicated office spaceFirst-floor livingMain-level laundryDining roomNew roofExtensive interior renovations
    Historic 1850 Charm with Modern Updates & In-Law Living! Step inside this beautifully remodeled 1850 home, thoughtfully updated for today's lifestyle while maintaining the character and charm that makes an older home so special. The main living portion of the home offers 3 spacious bedrooms, 2.5 baths, and a dedicated office space. The heart of the home features a bright and inviting open-concept kitchen, dining room, and living room, providing a comfortable layout for everyday living and entertaining. Main-level laundry adds even more convenience. The separate in-law living area offers first-floor living with 1 bedroom, 1 full bath, its own laundry area, and comfortable living space-ideal for extended family, guests, or multigenerational living. Major improvements include a new roof and new furnace, along with extensive interior renovations throughout. Outside, enjoy a large deck perfect for relaxing, entertaining, or summer gatherings. The property also features 2 detached garages, one that is oversized with heat, providing plenty of room for vehicles, storage, a workshop, or hobbies. It's a must see!!!
    1 day
    |
    154
    |
    9
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Michele Geragotelis (860)917-6090,

    RE/MAX Bell Park Realty 860-774-7600

    Source: Smart MLS,MLS#: 24200058MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Features: Ceiling Fan(s), Walk-In Closet(s)
      • Level: Upper
      Bedroom
      • Features: Ceiling Fan(s)
      • Level: Upper
      Bedroom
      • Features: Ceiling Fan(s)
      • Level: Upper
      Bedroom
      • Features: Ceiling Fan(s), Laundry Hookup, Walk-In Closet(s), Laminate Floor
      • Level: Main
      Primary bathroom
      • Features: Double-Sink, Stall Shower, Tile Floor
      • Level: Upper
      Bathroom
      • Features: Double-Sink, Stall Shower, Tile Floor
      • Level: Main
      Bathroom
      • Features: Double-Sink, Tub w/Shower, Tile Floor
      • Level: Upper
      Bathroom
      • Features: Laundry Hookup, Tile Floor
      • Level: Main
      Dining room
      • Features: Balcony/Deck, Beamed Ceilings, Tile Floor
      • Level: Main
      Kitchen
      • Features: Beamed Ceilings, Breakfast Bar, Granite Counters, Kitchen Island, Tile Floor
      • Level: Main
      Kitchen
      • Level: Main
      Living room
      • Level: Main
      Living room
      • Features: Ceiling Fan(s)
      • Level: Main
      Office
      • Level: Main
      Heating
      • Forced Air, Oil
      Cooling
      • Ceiling Fan(s)
      Appliances
      • Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Water Heater
      • Laundry: Main Level
      Features
      • 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

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: South Windham

      Financial & listing details

      • Price per square foot: $216/sqft
      • Tax assessed value: $166,280
      • Annual tax amount: $4,963
      • Date on market: 8/21/2026

        Estimated market value

        $540,900

        $514,000 - $568,000

        $2,395/mo

        Price history

        DateEventPrice
        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
        5/5/2013Price change$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

        Est. payment

        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.
        See how much you could borrow to make a competitive offer.
        Get pre-qualified

        Climate risks

        Neighborhood: 06266

        Getting around

        12 / 100
        Car-Dependent
        7 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes

              Nearby cities

              Nearby zip codes

              Other South Windham Topics

                Search
                Updates
                Favorites
                Plan
                Inbox