Perfectly situated in the heart of Woodstock Village, this charming move-in-ready single-level country cottage is complemented by a separate permitted studio cottage (STR)--an ideal artist's studio, guest cottage, home office, creative retreat, or potential income-producing opportunity. Together, they offer exceptional flexibility just moments from Woodstock's renowned restaurants, galleries, boutiques, markets, music venues, and year-round attractions. The main residence features two spacious bedrooms, each with walk-in closets, random-width pegged hardwood floors, recessed lighting, ceiling fans, updated windows with removable grilles, and a custom built-in entertainment center. The inviting living room is centered around a wood-burning fireplace, creating a warm and welcoming gathering space. The eat-in kitchen offers shaker-style knotty pine cabinetry, a farmhouse sink, all-new appliances, and a convenient laundry area. A standout feature is the stunning three-season screened porch with vaulted A-frame ceilings, floor-to-ceiling screens, and a built-in entertainment center--perfect for relaxing, entertaining, or simply enjoying views of the beautifully landscaped grounds. Step outside to discover mature gardens, a tranquil frog pond, charming fencing, winding gravel pathways, and a private patio ideal for outdoor dining and gatherings. The attractive novelty siding enhances the property's timeless Woodstock character. Additional amenities include a whole-house generator servicing both the main residence and studio cottage, a fully waterproofed crawl space with excellent storage, a spacious attic, a two-car carport, and a private driveway accommodating up to five vehicles. Whether you're searching for a full-time residence, a weekend escape, or a downsizing opportunity, this special Woodstock property offers the rare combination of a charming village home and a versatile detached artist's studio cottage, blending character, functionality, and income potential in one of the Hudson Valley's most sought-after locations.