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  • $735,000

    355 South Street, Windham, NY 12496

    2beds
    1,438sqft
    Single Family Residence
    Built in 1975
    1.3 Acres Lot
    $693,000 Zestimate®
    $511/sqft
    $-- HOA

    What's special

    Comfortable bright primary bedroomReading nookLarge walk-in closetExtra sleeping loftStone walkwaysAdditional loft sleeping areaWarm woodstove
    Excellent location with ease of access to Windham Mountain Club and town of Windham! Tucked up amongst the tress at the foot of Windham Mountain you will find this truly picturesque and enchanting home featuring 2 bedrooms and 2 full bath, plus extra sleeping loft and a 2 car garage with a cozy 1 bedroom apt! This home is brimming with character; the gable roof lines and classic detailing add visual interest and charm. The unique floor plan makes for an ideal mountain get away. Relax in the cozy sitting area, the sun filled, well-appointed kitchen offers plenty of counter space to create memorable meals to enjoy around the banquet styled table, with sliding doors out to the beautiful, private patio. The timber frame vaulted ceilings in the living area create an open airy feeling, while the warm woodstove adds to the rustic charm. The main floor also offers an elegant, full bath with a tastefully tiled walk in shower. The second floor offers a comfortable, bright primary bedroom, a cheerful bunkroom, an additional loft sleeping area and a large full bath with jetted tub, large walk-in closet and reading nook adding to the charm and functionality of this offering. The spacious 2 car garage offers a lovely 1 bedroom apt. with kitchenette, full bath and cozy living area with extra sleeping to use for guests or rental opportunity. The property will delight you with its striking circular stone fire pit with wood and stone seating, prominent attractive gazebo, stone walkways, flowering trees and evergreen shrubs. This offering may be the closet you'll come to stepping inside a storybook setting. A nature lovers paradise where you will enjoy skiing, snowboarding, hiking, biking, golf, yoga, day saps, indie bookstore, walking the Windham Path, fine restaurants, seasonal farmers markets and so much more.
    22 days
    |
    815
    |
    105
    |

    Zillow last checked: 8 hours ago

    Listing updated: November 18, 2025 at 12:05pm

    Listing by:

    Brainard Ridge Management 518-734-5333,

    Patricia Charbonneau 914-420-6873

    Source: HVCRMLS,MLS#: 20255740MLS Logo

    Tour with a local agent

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 2
    • Bathrooms: 2
    • Full bathrooms: 2
    Bedroom
    • Level: Upper
    Primary bathroom
    • Level: Upper
    Bathroom
    • Level: First
    Bathroom
    • Level: Upper
    Dining room
    • Level: First
    Great room
    • Level: First
    Kitchen
    • Level: First
    Living room
    • Level: First
    Loft
    • Level: Upper
    Heating
    • Baseboard, Electric, Oil
    Appliances
    • Included: Refrigerator, Microwave, Electric Range, Dishwasher
    • Laundry: Laundry Closet
    Features
    • Flooring: Carpet, Ceramic Tile, Wood
    • Has basement: No
    Interior area
    • Total structure area: 1,438
    • Total interior livable area: 1,438 sqft
    • Finished area above ground: 1,438
    • Finished area below ground: 0

    Property

    Parking
    • Total spaces: 2
    • Parking features: Garage
    • Garage spaces: 2
    Features
    • Levels: Two
    • Patio & porch: Patio
    • Has view: Yes
    • View description: Garden, Meadow, Mountain(s), Trees/Woods
    Lot
    • Size: 1.3 Acres
    • Features: Landscaped
    Details
    • Additional structures: Garage(s), Gazebo, Shed(s)
    • Parcel number: 95.06121.1
    • Zoning: res

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Cottage
    • Property subtype: Single Family Residence
    Materials
    • Board & Batten Siding, Frame
    • Foundation: Block
    • Roof: Shake,Shingle
    Condition
    • New construction: No
    • Year built: 1975

    Utilities & green energy

    • Electric: 200+ Amp Service
    • Sewer: Public Sewer
    • Water: Well
    • Utilities for property: Cable Connected, Sewer Connected

    Community & HOA

    Location
    • Region: Windham

    Financial & listing details

    • Price per square foot: $511/sqft
    • Tax assessed value: $332,300
    • Annual tax amount: $5,854
    • Date on market: 11/18/2025
    • Road surface type: Paved

    Estimated market value

    $693,000

    $658,000 - $728,000

    Not available

    Price history

    Price history
    DateEventPrice
    11/18/2025Listed for sale$735,000-15%$511/sqft
    Source: HVCRMLS #20255740 Report a problem
    12/25/2023Listing removed--
    Source: Columbia Greene Northern Dutchess MLS #146850 Report a problem
    11/1/2023Price change$865,000-3.8%$602/sqft
    Source: Columbia Greene Northern Dutchess MLS #146850 Report a problem
    8/31/2023Price change$899,000-9.6%$625/sqft
    Source: Columbia Greene Northern Dutchess MLS #146850 Report a problem
    6/24/2023Listed for sale$995,000$692/sqft
    Source: Columbia Greene Northern Dutchess MLS #146850 Report a problem

    Public tax history

    Public tax history
    Tax history is unavailable.

    BuyAbility℠ payment

    Estimated monthly payment
    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.
    Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
    See how much you could borrow to make a competitive offer.

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    Learn more*Terms apply. Match provided by Foyer. Account offered by Pacific West Bank, Member FDIC.

    Climate risks

    Neighborhood: 12496

    Nearby schools

    GreatSchools rating

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