Perfectly positioned along the Chester River in the sought-after waterfront community of Homeport, this exceptional brick-front residence offers expansive water views, refined interior updates, and resort-style outdoor living designed to embrace Maryland's Eastern Shore lifestyle. Set on a beautifully landscaped homesite with direct access to the water, the property combines timeless architecture with thoughtful modern improvements completed throughout the home. Inside, over 4,400 square feet of living space unfolds across three finished levels filled with natural light and panoramic water views. Hardwood flooring, updated lighting, fresh paint, and custom finishes create an inviting atmosphere throughout the main living areas. The spacious foyer opens to elegant formal living and dining rooms, while the heart of the home features a beautifully appointed kitchen with generous cabinetry, ample prep space, and seamless flow into the adjoining breakfast and family rooms overlooking the water. The impressive family room is anchored by a striking stone fireplace and expansive windows that frame the tranquil river setting. Designed for both everyday comfort and entertaining, the home offers multiple gathering spaces throughout, including study space on the upper level adds even more flexibility, perfect for a secondary lounge, reading area or workspace, and additional loft space on the second-level showcases a recreation area, complete with a wet bar, beverage cooler, and full bath, ideal for game nights, movie viewing, guest accommodations, or flexible lifestyle needs. The main-level primary suite serves as a luxurious retreat with water views, hardwood flooring, and a fully remodeled spa-inspired bath featuring Kohler fixtures, a soaking tub, glass-enclosed shower, updated tilework, and a custom California Closet-designed walk-in closet. Additional upper-level bedrooms and flexible living spaces provide versatility for guests, home offices, fitness areas, or multigenerational living. Extensive recent upgrades enhance both comfort and peace of mind, including dual high-efficiency Bosch HVAC systems installed in 2023 and 2024, a Rinnai Sensei tankless water heater, Honeywell smart thermostats on all three levels, whole-house water treatment and smart water management systems, updated bathrooms with Kohler fixtures, new lighting, ceiling fans, fresh interior paint, and improved landscaping with regrading, retaining walls, perennial gardens, and added privacy plantings. Outdoor living is equally exceptional, featuring a large covered deck, hot tub patio, beautifully maintained grounds, and private dock infrastructure ready for life on the water. Community amenities include a waterfront pool, clubhouse, tennis courts, and deep-water marina access. Conveniently located near Route 50 with easy access to Annapolis, the Bay Bridge, and the Eastern Shore's premier boating destinations, this remarkable property offers the ideal blend of luxury, comfort, and waterfront living.