Land with Home for Sale in Windham, New York

Turn-Key Catskills Timber Frame Retreat | Sold Fully Furnished | Mountain Views | Walk to Restaurants | Minutes to Windham Mountain Club This is the kind of authentic Catskills mountain retreat buyers spend years searching for. Proudly perched on a hill in one of Windham's most charming locations, this true 1900s timber frame home seamlessly blends historic character with the modern finishes and comforts today's second-home and STR buyers crave. Sold fully furnished and completely turn-key (minus two rugs in the dining and living rooms), this beautifully curated property is ready to enjoy immediately or continue operating as a proven vacation rental with approximately 20k already booked for the summer season and multiple winter rental inquiries already rolling in. From the moment you arrive, the craftsmanship and warmth of this home are undeniable. Stunning reclaimed hand-hewn beams are exposed throughout the house, their rich dark stain dramatically contrasted against crisp white walls and ceilings, creating the perfect blend of rustic luxury and modern mountain design. Hand-hewn posts and beams, gleaming wood floors, solid split front door details, and thoughtfully selected blue, gray, and earthy brown tones create the calming Catskills aesthetic buyers are actively searching for in today's luxury vacation home market. The kitchen perfectly balances old-world charm and modern functionality with white subway tile backsplash, stone countertops, breakfast bar seating, stainless steel appliances, and slate tile floors ideal for entertaining after a day on the slopes or golf course. The living room offers exposed timber frame details and a cozy fireplace that anchors the space perfectly for apres-ski evenings. Upstairs, you'll find three bedrooms including a stunning primary en-suite featuring vaulted ceilings accented by exposed hand-hewn beams and a spa-like bathroom complete with a soaking tub positioned against a large picture window overlooking mountain views, plus an oversized tiled walk-in shower. Two additional upstairs bedrooms are connected by a beautiful, modern Jack-and-Jill bathroom. The finished walk-out lower level adds exceptional flexibility and additional entertaining space with radiant heated slate floors, a spacious family room, wood accent wall, full bathroom, laundry area, and a flex room currently being utilized as a fourth bedroom/bunk room -- ideal for maximizing sleeping capacity and future Airbnb rental potential. Outside, the grounds are equally impressive with lush lawn space, eye-catching stone walls, mature landscaping, and a beautiful stone patio perfect for outdoor dining, relaxing, or gathering around a firepit under the Catskills sky. Location is everything -- and this property absolutely delivers. Enjoy being within walking distance to The Chicken Run, just minutes to golfing at Christman's Windham House, skiing at Windham Mountain Club, and the restaurants, shopping, coffee shops, and nightlife along Windham's vibrant Main Street. A rare additional opportunity exists for investors or large families looking to expand their Catskills portfolio -- the neighboring property at 7 Karlstadt Road is also available for purchase. Owning side-by-side homes in a thriving resort town like Windham creates an incredibly unique investment opportunity with simplified property management, stronger rental flexibility, and long-term upside in one of the Catskills' most desirable vacation destinations. Few opportunities exist to own neighboring turn-key properties within walking distance to town, restaurants, and four-season recreation. Additional highlights include city sewer, private well water with a new well pump installed in 2024, radiant heat in the lower level, and an unmatched combination of authentic historic timber frame architecture, modern amenities, STR income potential, and true Catskills charm.