Circa 1921, this charming and thoughtfully updated 4-bedroom, 2.5-bath residence beautifully blends historic character with modern comfort. Lovingly maintained and improved throughout, this exceptional home offers a spacious and versatile layout designed for today's lifestyle. Inside, you'll find a warm and inviting floor plan featuring a stunning wood-burning stone fireplace, original pine floors throughout much of the home that add warmth and timeless character, an updated kitchen with granite countertops and newer appliances, beautifully renovated bathrooms, a convenient first-floor laundry/mud room, and an oversized Andersen sliding glass door overlooking the expansive backyard. A second staircase provides easy access to the primary bedroom while adding to the home's unique character and functionality. Numerous updates and improvements provide peace of mind, including a newer boiler, updated mechanicals, 200-amp electric service, smart thermostats, a central vacuum system, and thoughtful upgrades throughout. The basement and generous attic space offer additional storage and flexibility. Outside, enjoy a beautifully landscaped property designed for entertaining and relaxation. The backyard features a saltwater in-ground pool with new coping and a new filter, a new paver patio, in-ground sprinklers with a private well water irrigation system, and plenty of room for gatherings, recreation, and outdoor enjoyment. A huge detached two-car garage with new windows, equipped with an electric car charging station, provides ample parking and storage, along with a newly finished climate-controlled bonus roomperfect for a hobby space, studio, gym, workshop, home office, or private retreat. Combining timeless charm, modern updates, and exceptional outdoor living, this rare property offers the opportunity to own a piece of history with all the conveniences of today. Perfectly situated in the heart of Riverhead, this home offers the best of East End living. Enjoy easy access to downtown waterfront, local dining, shops, entertainment, and year-round events, while being just minutes from farms, vineyards, beaches, golf courses, and everything the East End has to offer.