Historic waterfront pool home with dock and legal guest house in downtown New Port Richey. Set on Grand Boulevard on one of the largest lots in the district, this 4 bedroom, 3 bath estate has never flooded and offers direct Cotee River access with a private dock, boat lift, and deep-water connection. A rare Sears Roebuck Osborn model, the residence showcases original hardwoods, wide baseboards, vintage glass windows, and a show-stopping stone fireplace. The main home features a spacious dining room, sun-filled enclosed porch overlooking the river, and an updated kitchen with granite counters and modern appliances. The primary suite opens to the pool and includes an ensuite bath and interior laundry; secondary bedrooms offer tall ceilings and abundant natural light. Outdoors is a true Florida oasis with lush landscaping, screened pool, private courtyard, and majestic oaks for shade and privacy. The permitted detached in-law suite/guest house/ADU provides a full kitchen, living room, bedroom, and bathideal for multigenerational living, guests, or rental income. A newer oversized 2-car garage with workshop and storage loft, gated driveway, and ample off-street parking complete the property. Enjoy walkable access to downtown shops and restaurants, golf-cart-friendly streets, and a front-row seat to historic New Port Richey livingan exceptional riverfront opportunity with character, functionality, and location. (ROOF-2012)(A/C-2013)(W/H-2013)(IMPACT FRONT DOOR-2025)