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  • Price cut: $100K (2/16)
    $2,500,000

    110 Old Road, Windham, NY 12496

    7beds
    5,569sqft
    Single Family Residence
    Built in 2023
    5.3 Acres Lot
    $2,336,200 Zestimate®
    $449/sqft
    $-- HOA

    What's special

    Open loftPanoramic windowsModern eleganceSophisticated mountain styleMassive islandBreathtaking viewsWhole-house generator
    Luxury Mountain Retreat | 7 Bed • 5.5 Bath • 5 Acres | Direct Windham Mountain Views | Smart Home | No HOA. Experience luxury mountain living in this brand-new custom-built 7-bedroom, 5.5-bath chalet with unobstructed views of Windham Mountain Club, set on 5 private acres just minutes from downtown Windham, NY. Designed with impeccable European craftsmanship, high-end technology, and sophisticated mountain style, this home is ideal as a primary residence, ski retreat, or luxury vacation rental. Sophisticated Interior Design- Step inside to discover an open-concept layout with soaring ceilings, panoramic windows, and a grand great room framed by the mountain landscape. The imported German kitchen and bar feature a hidden pantry, Porcelanosa counters and tile, a massive island, double dishwashers, and a professional Viking 8-burner range—a dream for chefs and entertainers. Throughout the home, every detail reflects artisan precision: handmade white oak floors and stair treads from Vermont, custom European doors from Poland (including a front door valued over 13K), and large-format Porcelanosa tile that creates a spa-like atmosphere. Four en-suite bedrooms, including a private guest suite, provide comfort and privacy. Two laundry rooms—one on each floor for added convenience. The floating glass staircase, open loft, and vaulted living spaces embody modern mountain luxury. Smart Home & Comfort Features- This home integrates advanced smart technology and everyday essentials for a seamless lifestyle: Sonos whole-home audio system, Ring cameras, & ADT security. MyQ Smart Garage controls smart thermostats & water control system. Radiant floor heating throughout and a whole-house generator for peace of mind. Two garages for vehicles, gear, and extra storage. Outdoor Living- Enjoy true mountain living on the Trex wraparound deck with a covered outdoor lounge, perfect for sunrise coffee, sunset dinners, or relaxing after a day on the slopes. The inviting front porch provides additional space to take in the crisp Catskill Mountain air and spectacular views year-round. Prime Catskills Location- Located in Windham, New York, one of the Catskills' most sought-after destinations, this property offers easy access to Windham Mountain Club for skiing, golf, hiking, mountain biking, and year-round recreation. The vibrant Windham village nearby offers boutique shopping, fine dining, and small-town charm- all just 2.5 hours from NYC. Investment Opportunity- Currently used as the owner's personal second home and a successful part-time luxury vacation rental, this property presents excellent income potential for buyers seeking a turn-key investment in the Catskills. Its combination of location, design, and amenities appeals to both high-end vacationers and full-time residents. Key Features Overview: 7 Bedrooms | 5.5 Baths | 5 Private Acres | No HOA -Direct Windham Mountain Club views -Imported German kitchen & Porcelanosa finishes -Handmade Vermont white oak floors & Polish doors- Four en-suites + two laundry rooms- Viking 8-burner range & double dishwashers- Radiant heating & whole-house generator- Full smart home system: Ring, Sonos, ADT, Garage, Thermostats, & Water control - Trex wraparound deck with covered lounge Two garages & ample storage space. This is a rare opportunity to own one of Windham's most striking new luxury homes, offering breathtaking views, modern elegance, and exceptional comfort year-round. Whether you're seeking a vacation home in the Catskills, a smart mountain estate, or an investment property near Windham Mountain, this home captures everything there is to love about upstate New York living at its finest. Windham, NY — The Catskills' premier destination for luxury ski homes and mountain retreats. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
    97 days
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    357
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    Zillow last checked: 7 hours ago

    Listing updated: March 09, 2026 at 07:19am

    Listing by:

    Coldwell Banker Village GreenW 518-734-4200,

    Regina Tortorella 914-466-0329,

    Aaron Perer,

    Coldwell Banker Village GreenW

    Source: HVCRMLS,MLS#: 20256123MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 6
      • Full bathrooms: 5
      • 1/2 bathrooms: 1
      Heating
      • Forced Air, Propane, Radiant
      Cooling
      • Central Air
      Appliances
      • Included: Other, Water Heater, Washer, Refrigerator, Range, Propane Cooktop, Microwave, Electric Water Heater, Dryer, Dishwasher
      • Laundry: Inside, Sink
      Features
      • Bar, Entrance Foyer, High Ceilings, High Speed Internet, Kitchen Island, Open Floorplan, Pantry, Smart Home, Smart Thermostat, Walk-In Closet(s), Wet Bar
      • Flooring: Tile, Wood, Other
      • Basement: None
      • Number of fireplaces: 2
      • Fireplace features: Family Room, Gas Log, Great Room
      Interior area
      • Total structure area: 5,569
      • Total interior livable area: 5,569 sqft
      • Finished area above ground: 5,569
      • Finished area below ground: 0
      Video & virtual tour

      Property

      Parking
      • Total spaces: 4
      • Parking features: Off Street, Driveway
      • Attached garage spaces: 4
      • Has uncovered spaces: Yes
      Features
      • Levels: Tri-Level
      • Patio & porch: Deck, Porch
      • Has view: Yes
      • View description: Mountain(s), Trees/Woods, Other
      Lot
      • Size: 5.3 Acres
      • Features: Landscaped, Private, Secluded, Views
      Details
      • Parcel number: 79.0071
      • Zoning: 01
      • Other equipment: Generator

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary
      • Property subtype: Single Family Residence
      Materials
      • Frame, Wood Siding, Other
      • Foundation: Concrete Perimeter, Slab
      • Roof: Asphalt,Shingle
      Condition
      • New construction: No
      • Year built: 2023

      Utilities & green energy

      • Electric: 200+ Amp Service
      • Sewer: Engineered Septic, Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Security: Security System
      Location
      • Region: Windham

      Financial & listing details

      • Price per square foot: $449/sqft
      • Tax assessed value: $994,400
      • Annual tax amount: $16,770
      • Date on market: 12/21/2025
      • Road surface type: Paved

        Estimated market value

        $2,336,200

        $2.22M - $2.45M

        $7,477/mo

        Price history

        Price history
        DateEventPrice
        3/6/2026Contingent$2,500,000$449/sqft
        Source: HVCRMLS #20256123 Report a problem
        2/16/2026Price change$2,500,000-3.8%$449/sqft
        Source: HVCRMLS #20256123 Report a problem
        2/1/2026Price change$2,599,999-3.7%$467/sqft
        Source: HVCRMLS #20256123 Report a problem
        12/21/2025Listed for sale$2,699,999-3.6%$485/sqft
        Source: HVCRMLS #20256123 Report a problem
        12/15/2025Listing removed$2,800,000$503/sqft
        Source: Global MLS #202524965 Report a problem
        11/17/2025Price change$2,800,000-3.4%$503/sqft
        Source: Global MLS #202524965 Report a problem
        9/1/2025Listed for sale$2,900,000+11.6%$521/sqft
        Source: Global MLS #202524965 Report a problem
        10/8/2024Listing removed$2,599,000$467/sqft
        Source: Columbia Greene Northern Dutchess MLS #152967 Report a problem
        6/29/2024Price change$2,599,000-10.3%$467/sqft
        Source: Columbia Greene Northern Dutchess MLS #152967 Report a problem
        5/30/2024Listed for sale$2,899,000+11.5%$521/sqft
        Source: Columbia Greene Northern Dutchess MLS #152967 Report a problem
        1/31/2024Listing removed--
        Source: Columbia Greene Northern Dutchess MLS #150990 Report a problem
        1/16/2024Price change$2,600,000+8.3%$467/sqft
        Source: Columbia Greene Northern Dutchess MLS #150990 Report a problem
        12/27/2023Listed for sale$2,400,000+1510.7%$431/sqft
        Source: Columbia Greene Northern Dutchess MLS #150990 Report a problem
        12/26/2018Listing removed$149,000$27/sqft
        Source: Coldwell Banker Village Green - Windham #120902 Report a problem
        7/2/2018Listed for sale$149,000-57.3%$27/sqft
        Source: Coldwell Banker Village Green - Windham #120902 Report a problem
        12/2/2012Listing removed$349,000$63/sqft
        Source: Coldwell Banker Village Green Realty #85500 Report a problem
        10/20/2012Price change$349,000-7.9%$63/sqft
        Source: Coldwell Banker Village Green Realty #85500 Report a problem
        9/13/2012Price change$379,000-5.2%$68/sqft
        Source: Coldwell Banker Village Green Realty #85500 Report a problem
        8/31/2012Listed for sale$399,800$72/sqft
        Source: Coldwell Banker Village Green Realty #85500 Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2024-- $994,400 +155.9%
        2023-- $388,650 +180.3%
        2022-- $138,650 +207.4%
        2021-- $45,100
        2020-- $45,100
        2019-- $45,100
        2018-- $45,100
        2017$369 $45,100
        2016-- $45,100

        Find assessor info on the county website

        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.
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        Climate risks

        Neighborhood: 12496

        Getting around

        9 / 100
        Car-Dependent
        4 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        Local experts in 12496

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