Welcome to 747 Oakland Valley Road in Cuddebackville, NY—a rare Neversink Riverfront gem that seamlessly blends rustic charm with thoughtful modern updates. Tucked away on a full acre of land in the Port Jervis School District, this enchanting 4-bedroom, 2-bath two-story home offers just under 1,400 square feet of inviting living space, perfect for year-round living or as a weekend retreat. Pull into the paved driveway, spacious enough to accommodate multiple vehicles and even your river boat, and be greeted by the oversized, two-car pull-through garage—an ideal setup for hobbyists, outdoor enthusiasts, or anyone in need of serious storage space. A quaint front yard and front porch welcome you with warmth and charm, while the wood siding and five-year-old metal roof hint at the craftsmanship within. To the side, a fenced-in yard area and private patio offer a secure play space for pets or children. Step out back and be captivated by sweeping river views from the large rear deck—an entertainer’s dream. Stroll along the cobblestone pathway to the river’s edge, where you'll find a rustic outhouse, a shed, and energy-saving owned solar panels, all thoughtfully placed for convenience and enjoyment along the way. Inside, character and comfort come together in a space that’s rich with hardwood floors, knotty pine accents, an exposed brick wall and unique wood finishes across walls and ceilings. The main-level side entry leads into a welcoming enclosed porch/mudroom, which flows into the beautifully updated kitchen, complete with stainless steel appliances, a six-burner gas stove, and charming copper ceiling tiles and backsplash. The home’s cozy living room is centered around a wood-burning fireplace set within a tiled wall and built-in home bar—perfect for cozy nights in or entertaining guests. Sliding glass doors off the living area make for an effortless connection to the outdoor living space. The lower level also includes a full bath, a dedicated dining area, a pantry/laundry room, and one of the four bedrooms—ideal for guests or single-level living. Upstairs, you'll find three additional bedrooms, including one with a walk-in closet and another with a fun lofted space ideal for a play area or creative nook. The high ceilings in the upper rooms add a light and airy feel to the home, complementing the abundant natural light throughout. Additional updates and features include central air conditioning, a water softener, new well pump and furnace, and updated 220-amp electric. Ideally located just 10 minutes the NJ Transit train to NYC in NYC, this home offers the perfect balance of privacy and convenience. Whether you’re launching a boat from your backyard or enjoying the wineries, specialty shops, restaurants, and endless hiking and biking trails nearby, this is truly where the Hudson Valley meets the Catskills. The Neversink River flows just steps away and eventually into the Delaware—making this a boater’s and angler’s dream come true. This isn’t just a home—it’s a riverside lifestyle. Come experience all that 747 Oakland Valley Rd has to offer.