3-5 Hickory Hill Road, Windham, NY, 12496
About This Home
Experience an exceptional mountain retreat in one of Windham's most desirable locations. Set on 2.7 private acres and just a short walk to the heart of the village, this remarkable estate offers breathtaking panoramic views of the Windham Mountain Club, the ski slopes, and the surrounding Catskill Mountains. The main residence features 5 spacious bedrooms and 3 full bathrooms, designed for comfortable everyday living and effortless entertaining.The spectacular mountain scenery, filling the home with natural light and creating a seamless connection to the outdoors. Step outside to your own private oasis featuring an outdoor swimming pool, generous entertaining space, and unforgettable views that can be enjoyed year-round. Adding incredible versatility is a charming A-frame guest house complete with 1 bedroom and 1 full bathroom-perfect for hosting family and friends, creating a private workspace, or generating additional rental income. Whether you're searching for a full-time residence, a luxury weekend escape, or an investment opportunity in the heart of the Catskills, this unique property delivers an unmatched combination of privacy, convenience, and iconic mountain views. Just minutes from skiing, golf, hiking, restaurants, and all that Windham has to offer, this is a rare opportunity to own one of the area's most captivating properties.
Getting Around
Car-Dependent
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Property condition: Updated/Remodeled
- Year built: 2007
Materials
- Roof: Asphalt,Shingle
- Construction materials: Wood Siding
Type & Style
- Home type: SingleFamily
- Architectural style: Chalet
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Washer/Dryer,Refrigerator,Microwave,Gas Oven,Gas Cooktop,Dishwasher
Basement
- Has basement: Yes
- Basement: Finished,Full,Walk-Out Access
Bedrooms & Bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
Features
- Flooring: Hardwood,Tile
- Finished area below ground: 1,080
- Finished area above ground: 1,080
Heating & Cooling
- Heating features: Baseboard,Propane,Wood Stove
- Cooling features: Ductless,Heat Pump,Multi Units,Zoned
Interior Area
- Total structure area: 2,974
- Total interior livable area: 2,974 sqft
Property
Details
- Parcel number: 194600 78.000673
- Zoning: 01
Features
- Levels: Bi-Level
- Pool features: In Ground
- Patio & porch: Deck,Front Porch,Rear Porch
- Has view: Yes
- View description: Mountain(s)
Lot
- Lot size: 2.75 Acres
- Features: Landscaped,Views
Parking
- Total spaces: 8
- Parking features: Garage Faces Front,Paved,Driveway
- Has garage: Yes
- Attached garage spaces: 2
- Covered spaces: 2
- Has uncovered spaces: Yes
- Uncovered spaces: 6
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Inland Flooding
- Cold Wave
- Hurricane
- Tornado
- Winter Weather
How This Home’s Risks Compare
FEMA Declared Disasters in Greene County and New York
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $8,039 | $96,468 |
| Home Insurance * | $1,156 | $13,872 |
| Property Taxes | $1,841 | $22,092 |
| Electricity | $491 | $5,897 |
| Total | $11,527 | $138,324 |
Income You'd Need if You Spent...
New York FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-07-13 | Listed for sale | $1,590,000 |
| 2025-05-01 | Listing removed | $1,399,000 |
| 2024-09-11 | Listed for sale | $1,399,000 |
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