Don't miss this unique opportunity to establish a year-round retreat in the Catskill Mountains, ideal for hosting family and friends on two separate lots. The grounds offer apple picking, fishing in the pond, and swimming, while children can enjoy outdoor activities and grandparents relax on the upper deck with scenic mountain views—all accessible from your own front yard. In winter, prepare for days on nearby Windham Ski slopes and return to a spacious chalet featuring an open great room with a warm fireplace in the sunken living area. The property includes ample space for holiday gatherings or casual meals at the kitchen island. The main floor consists of two large bedrooms, a full bathroom, laundry facilities, and a half bath adjacent to the kitchen. Upstairs, a primary suite and loft provide additional privacy and comfort.
The sought-after family room is equipped with a supplementary kitchen, wood-burning stove, quality ski furnishings, pool table, dart games, extra office/sleeping space, and another full bathroom. A convenient one-car garage ensures secure late-night arrivals and easy access. The home boasts a new heating system, full-house air conditioning, and high-quality finishes including marble, hardwood and carpet flooring, wood doors and trim, skylights, and vaulted ceilings—creating a true mountain chalet ambiance. Offered furnished and turnkey, this custom-built home has never before been on the market and is ready for its next owners. Located just minutes from Windham Club, it offers access to year-round activities and the potential to become your dream mountain residence.
Active
Price cut: $50K (2/28)
$749,000
415 Old Road, Windham, NY 12496
3beds
3,729sqft
Single Family Residence
Built in 1988
4 Acres Lot
$696,300 Zestimate®
$201/sqft
$-- HOA
What's special
Warm fireplaceSpacious chaletOpen great roomQuality ski furnishingsApple pickingPrimary suiteWood-burning stove
- 190 days |
- 1,100 |
- 31 |
Zillow last checked: 7 hours ago
Listing updated: March 16, 2026 at 03:37pm
Listing by:
Hunter Windham Real Estate 518-965-8439,
Laurie Hanenberg,
Dylan Hanenberg,
Hunter Windham Real Estate
Source: HVCRMLS,MLS#: 20254472
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Level: Upper
Bedroom
- Level: Main
Bedroom
- Level: Main
Primary bathroom
- Level: Upper
Bathroom
- Level: Main
Bathroom
- Level: Lower
Other
- Level: Main
Dining room
- Level: Main
Family room
- Level: Lower
Kitchen
- Level: Main
Kitchen
- Level: Lower
Laundry
- Level: Main
Living room
- Level: Main
Loft
- Level: Upper
Office
- Level: Lower
Heating
- Baseboard, Hot Water, Oil
Cooling
- Ceiling Fan(s), Central Air
Appliances
- Included: Washer/Dryer, Microwave, Exhaust Fan, Electric Range, Dishwasher
- Laundry: Laundry Room
Features
- Ceiling Fan(s), Double Vanity, Eat-in Kitchen, High Ceilings, High Speed Internet, Kitchen Island, Open Floorplan, Recessed Lighting, Recreation Room
- Flooring: Carpet, Hardwood, Marble, Tile
- Doors: Mirrored Closet Door(s), Sliding Doors
- Windows: Insulated Windows, Wood Frames
- Basement: Finished,Full,Walk-Out Access
- Number of fireplaces: 1
- Fireplace features: Living Room, Masonry, Wood Burning Stove
Interior area
- Total structure area: 3,729
- Total interior livable area: 3,729 sqft
- Finished area above ground: 2,434
- Finished area below ground: 1,295
Property
Parking
- Total spaces: 1
- Parking features: Garage Faces Side, Driveway
- Attached garage spaces: 1
- Has uncovered spaces: Yes
Features
- Levels: Three Or More
- Stories: 2
- Patio & porch: Deck, Wrap Around
- Exterior features: Private Yard
- Has view: Yes
- View description: Mountain(s), Pond
- Has water view: Yes
- Water view: Pond
Lot
- Size: 4 Acres
- Dimensions: 550 x 350
- Features: Pond on Lot, Corner Lot, Front Yard, Paved, Private, Rectangular Lot
Details
- Additional structures: Shed(s)
- Parcel number: 26.2,26.1
- Zoning: R
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Chalet
- Property subtype: Single Family Residence
Materials
- Batts Insulation, Concrete, Frame, Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1988
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Available, Electricity Connected, Phone Available, Water Connected, Underground Utilities
Community & HOA
Community
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Windham
Financial & listing details
- Price per square foot: $201/sqft
- Tax assessed value: $367,700
- Annual tax amount: $5,789
- Date on market: 9/19/2025
- Listing terms: Cash,Conventional
- Electric utility on property: Yes
- Road surface type: Asphalt
Estimated market value
$696,300
$661,000 - $731,000
$5,832/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 2/28/2026 | Price change | $749,000-6.3%$201/sqft |
Source:  HVCRMLS #20254472 Report a problem | ||
| 9/19/2025 | Listed for sale | $799,000$214/sqft |
Source: HVCRMLS #20254472 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $347,700 |
| 2023 | -- | $347,700 |
| 2022 | -- | $347,700 |
| 2021 | -- | $347,700 |
| 2020 | -- | $347,700 |
| 2019 | -- | $347,700 |
| 2018 | -- | $347,700 -8.3% |
| 2017 | $5,992 | $379,200 |
| 2016 | -- | $379,200 |
| 2015 | -- | $379,200 |
| 2014 | -- | $379,200 |
| 2013 | -- | $379,200 +21.3% |
| 2012 | -- | $312,500 |
| 2011 | -- | $312,500 |
| 2010 | -- | $312,500 |
| 2009 | -- | $312,500 |
| 2008 | -- | $312,500 |
| 2007 | -- | $312,500 |
| 2006 | -- | $312,500 |
| 2005 | -- | $312,500 |
| 2004 | -- | $312,500 |
| 2003 | -- | $312,500 +83.8% |
| 2002 | -- | $170,000 |
| 2001 | -- | $170,000 |
| 2000 | -- | $170,000 |
Find assessor info on the county website
BuyAbility℠ payment
Estimated monthly payment
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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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Neighborhood: 12496
Nearby schools
GreatSchools rating
- 6/10Windham Ashland Central SchoolGrades: PK-12Distance: 2.9 mi
Local experts in 12496
- New York
- Greene County
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- 415 Old Road
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