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  • $1,200,000

    5344 Main St., Windham, NY 12496

    3beds
    6,400sqft
    Single Family Residence
    Built in 1975
    7,840.8 Square Feet Lot
    $1,222,600 Zestimate®
    $188/sqft
    $4,898 Estimated rent

    Home value

    $1,222,600

    Estimated sales range

    Not available

    $4,898/mo

    Zestimate® history
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    $8,385/mo

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    What's special

    One of the most iconic pieces of Real Estate in Windham, New York is Back on the Market!! Seller Financing Available! Nestled in the Heart of Windham on bustling Main Street, this unique mixed-use property offers a blend of commercial & retail opportunity plus income generating apartments. The perfect investment that is fully rented and generating great returns that could easily carry a financing element! A community staple that houses The Main Street Market, formerly Todaro's, plus 3 additional 1 Bedroom 1 Bath Apartments upstairs. Situated on Main Street, this building benefits from high visibility and foot traffic, ideal for any retail business looking to thrive in a vibrant community setting. Whether you continue its current successes or attempt a new venture, the possibilities are endless. The ground floor features a spacious retail area, perfect for a variety of businesses. The space is designed to attract both locals and the influx of tourists Windham sees throughout the year. Above the retail space lie three spacious apartments that have been rented for years. This property presents an excellent opportunity for investors looking for dual income streams. The rental potential from both the retail and residential components ensures a steady cash flow, with the added benefit of appreciation in a sought-after location. With the right vision, there's potential for expansion or modification. The property could be an ideal candidate for those looking to add their personal touch or capitalize on Windham's growing popularity. The property being mixed-use, offers flexibility in how the space can be utilized. Have it be owner / operator and live upstairs or just rent of all 4 spaces and generate great monthly cash flow, the choice is yours. The building not only serves as a community hub but also as a cultural landmark on Main Street. This property on Main Street, Windham, is more than just a building; it's an opportunity to own a piece of a thriving small town. Whether you're looking to start or expand a business, invest in real estate, or find a unique place to call home, this property offers the best of both worlds. Contact us today to arrange a viewing and explore the possibilities this gem on Main Street has to offer. There's an additional back lot not included in the sale but can be if interested that's already subdivided as a blank canvas ready to build another retail or residential structure with access Municipal Water & Sewer!

    Zillow last checked: 7 hours ago

    Listing updated: May 09, 2025 at 06:07pm

    Listed by:

    Philippe Uhrik 518-528-6186,

    Win Morrison Realty - Catskill

    Bought with:

    Mary Donovan

    Gallagher & Company

    Source: HVCRMLS,MLS#: 156927MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 3
    • Full bathrooms: 3
    Heating
    • Other
    Appliances
    • Included: Water Heater, Electric Water Heater
    Features
    • High Speed Internet
    • Flooring: Other
    • Basement: Full
    • Has fireplace: No
    Interior area
    • Total structure area: 6,400
    • Total interior livable area: 6,400 sqft

    Property

    Features
    • Levels: Two
    • Stories: 2
    • Has view: Yes
    • View description: Mountain(s)
    Lot
    • Size: 7,840 sqft
    Details
    • Parcel number: 78.19112

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    • Attached to another structure: Yes
    Materials
    • Other
    • Foundation: Concrete Perimeter
    • Roof: Other
    Condition
    • Year built: 1975

    Utilities & green energy

    • Electric: 200+ Amp Service
    • Sewer: Public Sewer
    • Water: Public

    Community & neighborhood

    Location
    • Region: Windham

    HOA & financial

    HOA
    • Has HOA: No

    Other

    Other facts
    • Road surface type: Paved

    Price history

    DateEventPrice
    4/30/2025Sold$1,200,000-7.3%$188/sqft
    Source: HVCRMLS #156927 Report a problem
    4/29/2025Contingent$1,295,000$202/sqft
    Source: Columbia Greene Northern Dutchess MLS #156927 Report a problem
    4/29/2025Listed for sale$1,295,000$202/sqft
    Source: Columbia Greene Northern Dutchess MLS #156927 Report a problem
    4/29/2025Contingent$1,295,000$202/sqft
    Source: Columbia Greene Northern Dutchess MLS #156927 Report a problem
    3/10/2025Price change$1,295,000-0.4%$202/sqft
    Source: Columbia Greene Northern Dutchess MLS #154461 Report a problem
    2/20/2025Price change$1,300,000+0.4%$203/sqft
    Source: Columbia Greene Northern Dutchess MLS #154461 Report a problem
    10/16/2024Price change$1,295,000-0.4%$202/sqft
    Source: Columbia Greene Northern Dutchess MLS #154461 Report a problem
    9/13/2024Listed for sale$1,300,000-3.7%$203/sqft
    Source: Columbia Greene Northern Dutchess MLS #154461 Report a problem
    7/1/2024Listing removed--
    Source: Columbia Greene Northern Dutchess MLS #150929 Report a problem
    5/31/2024Contingent$1,350,000$211/sqft
    Source: Columbia Greene Northern Dutchess MLS #150929 Report a problem
    5/3/2024Pending sale$1,350,000$211/sqft
    Source: Columbia Greene Northern Dutchess MLS #150929 Report a problem
    3/9/2024Price change$1,350,000-8.1%$211/sqft
    Source: Columbia Greene Northern Dutchess MLS #150929 Report a problem
    12/13/2023Listed for sale$1,469,000+4.9%$230/sqft
    Source: Columbia Greene Northern Dutchess MLS #150929 Report a problem
    10/1/2023Listing removed--
    Source: Columbia Greene Northern Dutchess MLS #149858 Report a problem
    9/9/2023Listed for sale$1,400,000$219/sqft
    Source: Columbia Greene Northern Dutchess MLS #149858 Report a problem
    9/7/2023Listing removed--
    Source: Columbia Greene Northern Dutchess MLS #147174 Report a problem
    7/27/2023Listed for sale$1,400,000-6.7%$219/sqft
    Source: Columbia Greene Northern Dutchess MLS #147174 Report a problem
    7/1/2023Listing removed--
    Source: OneKey® MLS as distributed by MLS GRID #H6243518 Report a problem
    4/20/2023Price change$1,500,000+99900%$234/sqft
    Source: OneKey® MLS as distributed by MLS GRID #H6243518 Report a problem
    4/17/2023Price change$1,500-99.9%
    Source: OneKey® MLS as distributed by MLS GRID #H6243518 Report a problem
    2/9/2023Listed for sale$1,500,000$234/sqft
    Source: Columbia Greene Northern Dutchess MLS #145285 Report a problem

    Public tax history

    Tax history is unavailable.

    Neighborhood: 12496

    Nearby schools

    GreatSchools rating