40 Simmons Drive, Woodstock, NY 12498

• 3 beds |
• 2 baths |
• 1,814 sqft

Property Description

Originally built by the developer of Simmons Drive as his personal home, this spacious Woodstock property offers a rare combination of Village convenience, mountain views, and a peaceful park-like setting. Situated on a quiet no-outlet street, it's just a five-minute stroll to Good Night restaurant, Tinker Street shopping, cafés, galleries, and everything the Village of Woodstock has to offer, all while enjoying a backyard shaded by mature trees and bordering Andy Lee Field, with no residential neighbors directly behind you. The home offers three bedrooms, though it lives comfortably as four, with plenty of additional flexible space. An enclosed porch and wood-burning stove add warmth and character, while skylights bring natural light into the sunroom. Opening directly onto the deck, the sunroom offers an exciting opportunity to create a generous primary suite. Downstairs, an additional flex room can serve as an office, exercise room, creative space, or extra storage. A two-car garage provides even more room for storage and projects, while the backyard offers space to gather around the fire pit beneath the trees. Lovingly maintained and improved over the years, the home has seen numerous important updates, including bathrooms updated in 2019, a 200-amp electrical service, a furnace rebuilt in 2025, an approximately five-year-old oil tank, a main roof approximately nine years old, and fencing and decking improvements completed in 2019. Big enough for all your friends, flexible enough for the way you actually want to live, and just minutes from the heart of Woodstock by any means of travel.

Listing Status:

Active

Date Added:

August 26, 2026

Data Last Updated:

September 24, 2026 at 3:40AM

Listing Office:

BHHS HUDSON VALLEY PROP-WDST : 845-679-0006

Listing Agent:

James Angelakis : 845-399-0734

MLS ID:

20264927

Interior

• General: Breakfast BarCeiling Fan(s)Smart Camera(s)/Recording3 Seasons RoomSun Room
• Appliances: DishwasherElectric OvenMicrowaveRefrigeratorWasher/Dryer
• Laundry: Lower Level
• Basement: Finished
• Flooring: TileVinylWood
• A/C: Wall/Window Unit(s)
• Heating: OilWood Stove

Exterior

• General: Awning(s)Basketball CourtFire PitPlaygroundPrivate YardTennis Court(s)Second Garage
• Style: Split Level
• Parking: BoatRV Access/Parking

Construction

• Roofing: Tile
• General: ConcreteFoam InsulationStoneVinyl Siding4Slab

Location

• Golf: GolfLakeParkPlaygroundRestaurantSidewalksTennis Court(s)
• Originating MLS: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS®)
• School District: Onteora Central School District
• County: Ulster

Lot

• Zoning: R1.5SBL 27.10-2-25; Town of Woodstock; 40 Simmons Dr; 210 1-family res; FRNT 100.00; ACRES 0.28; Onteora CSD; Deed Bk 671227.10-2-25
• Fencing: Back YardSee RemarksWood

Utilities

• Utilities: 200+ Amp Service
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS®)