Perfectly positioned along the tranquil shores of Winchester Creek, at the base of the Chester River in the sought-after waterfront community of Homeport, this exceptional brick-front residence with coastal flair offers sweeping water views, refined interior updates, and resort-style living designed to embrace Maryland's Eastern Shore lifestyle. Nestled on a beautifully landscaped homesite with direct water access and a private natural shoreline, the property captures the beauty of waterfront living with peaceful views, ever-changing sunsets, and a seamless connection between indoor and outdoor spaces. Inside, more than 4,400 square feet of light-filled living space unfolds across three finished levels, where expansive windows frame the sparkling waterfront setting from nearly every angle. Curated upgrades including hardwood flooring, fresh interior paint, custom millwork and designer finishes create a relaxed luxury aesthetic throughout the home. The welcoming foyer is flanked by a cozy living room with fireplace and a formal dining room ideal for entertaining. Beyond, the foyer opens into a dramatic two-story family room anchored by an upgraded fireplace, soaring custom millwork surround and a waterside-wall of stacked windows that showcase breathtaking water views and fill the open plan home with natural light. Designed for everyday comfort and effortless entertaining, the gourmet kitchen has been beautifully updated with abundant cabinetry, a contrast center island in coastal blue with breakfast bar seating, quartz countertops, designer tile backsplash, pendant lighting, heated floors and ss appliances that are positioned to enjoy the waterfront backdrop at every meal. Multiple gathering spaces provide exceptional flexibility for modern lifestyles. An upper-level flex space serves perfectly as a reading lounge, hobby area, home office or secondary family room. The third floor features a wet bar, beverage cooler, and full bath, ideal for movie nights with surround-sound, game days, guest accommodations or multigenerational living. The main-level primary suite offers a luxurious retreat with peaceful water views, hardwood flooring, and a fully remodeled spa-inspired bath featuring Kohler fixtures, a sunlit soaking tub, glass-enclosed shower, designer tilework and walk-in California Closets. A second waterside ensuite bedroom on the main level also enjoys beautiful water views and a private bath. Outside, the serpentine paver walkway leads to an open front porch framed by two-story columns and custom coastal blue front door. The waterfront setting is a centerpiece of daily living where the waterside elevation includes a newly expanded dining deck, updated covered porch and grand stairs that lead to a comfortable backyard, side brick paver patio for grilling and professional planting areas create an outdoor retreat designed for relaxation and entertaining. Whether enjoying morning coffee overlooking the glistening water, afternoon siestas by the water, hosting sunset gatherings, heading out for water activities from the deeded boat slip from Homeport's private pier, this property offers an exceptional opportunity to experience the very best of Eastern Shore waterfront living. Extensive recent improvements provide both comfort and peace of mind, including dual high- efficiency Bosch HVAC systems (2023 & 2024), a Rinnai Sensei tankless water heater, Honeywell smart thermostats on all three levels, whole-house water treatment and smart water management systems, updated baths with Kohler fixtures, ceiling fans, fresh interior paint, and professionally enhanced landscaping with regrading and privacy enhancements.