
Land with Home for Sale in Montgomery, New York
560 Winding Hill Rd, Montgomery, NY 12549
Welcome to 560 Winding Hill Road, a 4-bedroom, 2.5-bath Colonial set on 15 private acres in the desirable Pine Bush School District. This home offers the perfect combination of comfort, functionality, and outdoor enjoyment for everyday living.
A welcoming front porch opens into a bright and spacious interior featuring hardwood floors throughout much of the main level. The living room, anchored by a wood-burning fireplace, creates a warm and inviting gathering space, while the formal dining room is ideal for dinners and celebrations. The naturally sunlit eat-in kitchen offers stainless steel appliances, tile flooring, and plenty of space for daily meals. Upstairs, the oversized primary suite provides a true retreat with a walk-in closet, jacuzzi tub, and separate shower.
Practical features include a 2-car garage, full unfinished basement with endless storage potential, and generator hook-up for peace of mind. Outdoors, the property invites year-round enjoyment--host summer barbecues on the back deck, gather around the firepit on crisp fall evenings, or take advantage of private trails that wind through your very own 15 acres.
All this is just minutes from local parks, restaurants, shopping, fitness centers, and commuter routes--making it easy to balance country living with modern convenience. 560 Winding Hill Road is more than a home; it's a place to grow, relax, and enjoy every season.
Location
- Street address
- 560 Winding Hill Rd
- County
- Orange County
- School district
- Pine Bush
- Elevation
- 492 feet
Property details
- Acreage
- 15 acres
- MLS #
- MLSLI 907550
- Posted
Property taxes
- 2025
- $14,113
Parcels
- 332600-017-000-0001-057.700-0000
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
- Franchise
- Keller Williams Realty
Exterior
- Parking
- Garage
Structure
- Style
- Colonial
- Heating
- Fireplace(s), Oil
- Cooling
- Central Air
- Materials
- Vinyl Siding
Interior
- Room Count
- 10
- Rooms
- Basement, Bathroom x 3, Bedroom x 4, Dining Room, Family Room, Kitchen, Laundry, Living Room
- Flooring
- Hardwood, Tile, Vinyl
- Appliances
- Dishwasher, Microwave, Refrigerator, Washer
- Features
- Eat-In Kitchen, Entrance Foyer, Formal Dining, Kitchen Island, Open Floorplan, Open Kitchen, Primary Bathroom, Storage, Walk-In Closet(s), Washer/Dryer Hookup
Nearby schools
| Name | Level | District | Description |
|---|---|---|---|
| E J Russell Elementary School | Elementary | Pine Bush | — |
| Crispell Middle School | Middle | Pine Bush | — |
| Pine Bush Senior High School | High | Pine Bush | — |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Oct 11, 2025 | Under contract | $649,999 | — | MLSLI |
| Oct 5, 2025 | Listing removed | $649,999 | — | Listing agent |
| Sept 23, 2025 | New listing | $649,999 | — | MLSLI |











































