27 Old Wagon Road, Woodstock, NY 12498

• 4 beds |
• 5 baths |
• 3,080 sqft

Property Description

Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths measuring 2200 sq. ft. The detached cottage has one bedroom with one full bath measuring 480 sq.ft and the detached studio has another full bath measuring 400 sq ft. The main house is a light-filled classic Woodstock modern home built around the original Woodstock's artist's cabin. Thoughtfully designed to frame the surrounding forest through expansive glass sightlines, allowing for views of deer, birds, and other wildlife throughout the seasons. Inside, the home showcases unique historical details such as chestnut beams in the dining room, a bluestone fireplace, a built-in library, and a mix of slate, Spanish tile, pine, and oak flooring. The multi-level living area features a lofted tongue-and-groove wood ceiling and five architectural skylights that bring the outdoors in. Upon entry, you're greeted by a bright and inviting sunroom that opens into a formal foyer. Just off the foyer is a room that can serve as a home office, reading nook, or playroom, conveniently located next to a full guest bathroom. This level also features a cozy bedroom and a hallway office nook—perfect for remote work or quiet study. The eat-in kitchen includes a charming breakfast nook that offers serene views of the surrounding landscape and seamlessly flows into the dining room, creating a warm and inviting connection between the spaces. The dining area doubles as a music room, enhanced by vintage wide-plank pine flooring and a wood-burning fireplace that adds warmth and character. Step down into the sunken living room, where high ceilings and built-in bookshelves create a bright, welcoming space ideal for relaxing or entertaining. The primary suite features an en-suite bathroom with Parisian influences, including a bidet and a deep, one-person soaking tub with jacuzzi jets. Sliders walk out to the private multi-level deck and your own private atrium. Just off the main area, a newly designed mason-laid bluestone patio features a seamless transition into an expansive deck, offering the perfect setting for quiet evenings or vibrant dinner parties. The second floor features a loft area, ideal as a TV or family room, providing a comfortable space to relax or entertain. Tucked away for privacy, the second primary suite includes a full bath, creating a serene retreat separate from the main living areas. The one-bedroom cottage evokes the feel of an English guesthouse, with wood floors, a full kitchen and bathroom, and its own dedicated utilities, making it a wonderful space for guests or potential rental income. The detached studio, adjoining the three-car garage, feels like a New York City loft, complete with wide-plank floors, an open-concept layout, a bathroom, and a kitchenette. With its own electric and utilities, the space lends itself well to use as an office, yoga or art studio, or another income-producing rental. The garage offers three bays—two for vehicles and one ideal for workshop or storage use. For decades, this special property has been a gathering place for artists, musicians and writers. The home is designed to inspire and connect, all within minutes of Woodstock's vibrant center. It's an exceptional retreat with comfort, character, and potential in every direction. Please see addendum for recent updates and improvements on the home.

Listing Status:

Active

Date Added:

July 10, 2025 at 05:00AM

Listing Office:

Berardi Realty : 845-201-1111

Listing Agent:

Megan Rios : 914-388-5794

MLS ID:

20252879

Interior

• General: Beamed CeilingsBuilt-in FeaturesBidetBookcasesCeiling Fan(s)Entrance FoyerEat-in KitchenHigh CeilingsHigh Speed InternetPrimary DownstairsStorageTrack LightingVaulted Ceiling(s)Walk-In Closet(s)Sun Room
• Appliances: DryerDishwasherMicrowaveRangeRefrigeratorWasher
• Laundry: In HallMain Level
• Basement: Crawl SpacePartialUnfinished
• Flooring: CarpetCeramic TileTileWood
• A/C: Ceiling Fan(s)Wall/Window Unit(s)
• Heating: BaseboardElectricOil
• Fireplace: Dining RoomStoneFireplaceFireplaces: 1

Exterior

• General: GardenLightingPrivate YardStorageGarage(s)GreenhouseGuest HouseOutbuildingOtherSecond ResidenceShed(s)
• Style: Contemporary
• Parking: DrivewayGarage Faces SideGravelOff Street

Construction

• Roofing: AsphaltBuilt-UpMembraneRubber
• Windows: Double Pane WindowsInsulated WindowsSkylight(s)Storm Window(s)Double Hung Window(s)
• General: Board & Batten SidingFrameVertical SidingWood Siding2BlockStone

Location

• Road/Access: County Road
• Originating MLS: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS®)
• School District: Onteora Central School District
• County: Ulster

Lot

• Zoning: R327.14-2-1727.14
• View: Rural
• Fencing: Wood

Utilities

• Utilities: Cable ConnectedNatural Gas Not AvailablePhone AvailableSewer Not Available200+ Amp Service
• Water: Well
• Sewer: Septic Tank

Financial

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

This listing courtesy of Megan Rios, Berardi Realty