Currently operating as an award winning B&B, this thoughtfully designed, flexibly configured income property is also ideal as a primary residence. Situated at 45 Pleasant Street, just a short stroll from the shops, restaurants and galleries of Woodstock Village, the property overlooks East End Park and the Ottauquechee River Trail, offering an exceptional blend of village convenience as well as natural beauty and outdoor recreation. Inside, historic Vermont charm meets sophisticated contemporary design, with rich finishes, warm hardwood floors, dramatic tilework, custom built-ins and thoughtfully designed lighting throughout. Beautifully appointed baths feature contemporary tile, glass-enclosed showers and upscale finishes reminiscent of a luxury boutique hotel. Guest accommodations offer comfort and privacy, with each principal guest room featuring a king bed, private bath and wet bar equipped with refrigerator, microwave and coffee maker. The expansive 420-square-foot suite includes a separate living room and spa-inspired bath with double vanity, heated floors, heated towel rack and jetted tub. Inviting common areas, a guest lounge, wraparound porch, decks, gardens and fire-pit areas create wonderful spaces for entertaining or relaxation. A dedicated yoga/Pilates studio offers additional flexibility for wellness activities or personal enjoyment. The private upper-level owner's quarters feature two bedrooms, two beautifully appointed baths, a full eat-in kitchen and finished attic space, providing exceptional flexibility for an owner/operator, extended family or full-time residence. Enjoy Woodstock's four-season lifestyle, from skiing and snowshoeing to hiking, golf, cycling and exploring Vermont's scenic countryside. Whether envisioned as a private residence, hospitality venture or investment property, this distinctive offering combines an established rental platform, exceptional location and versatile living spaces. A rare opportunity to make it your own!