395 Boston Post Road

Introducing the historic Ebenezer Dudley Home, circa 1828, a beautifully preserved residence set along the iconic stretch of Boston Post Road in the charming shoreline town of Madison, Connecticut. Situated on nearly an acre of picturesque grounds, this special property seamlessly blends early New England character with thoughtful modern updates, offering both historic charm and everyday comfort. During the past five years of ownership, the current homeowners have undertaken extensive improvements and updates throughout the property. Among them are the addition of a spectacular wraparound screened porch with bluestone flooring, a birch board ceiling and wood burning stove, the conversion to natural gas heat and tankless hot water, installation of a new 50-year architectural shingle roof, an updated kitchen, and a beautifully renovated first-floor bathroom, are just a few of the many thoughtful enhancements made to the home. A significant addition completed in 2003 expanded the home's living space to include the kitchen, family room, and a spacious primary bedroom suite designed for modern living. The private primary suite features a generous full bath, a dressing room and walk-in closet, creating a comfortable and elegant retreat. Two additional ensuite bedrooms complete the second floor, along with a large, gracious landing that connects the three bedrooms and enhances the sense of space. Wide original floorboards run throughout much of the home, while abundant windows fill the rooms with beautiful natural light. The interior offers a flexible layout, including a first-floor office and the beautiful new full bath that allows for a convenient guest suite or potential fourth bedroom. The bright, updated eat-in kitchen includes granite counters, an island, double ovens, a large pantry and heated tile flooring. French doors open to the home's newest and most spectacular addition: the wraparound screened porch designed for relaxed shoreline living. This inviting space is perfect for summer dining, morning coffee, or evening gatherings while enjoying views of the beautiful grounds. The property itself is nothing short of enchanting. Mature landscaping and established gardens create a private and colorful setting that changes with the seasons. In bloom, the grounds overflow with peonies and daffodils, while morning glories, an arbor of wisteria, graceful Japanese maples, and a magnificent magnolia tree add layers of beauty and character to the landscape. A detached two-car garage with a studio above includes a full bath, offering wonderful flexibility for guests, a home office, gym, or creative space. An outdoor shower adds a classic shoreline touch after a day at the nearby beach, walking distance away. Ideally located, the home is just a short walk or bike ride to the historic Madison Green, where residents gather for summer concerts, weekend antique shows, and the popular Friday farmer's market. Madison's beautiful beaches, charming shops, restaurants, and coastal attractions are all close by. Rich in history, filled with light, and surrounded by beautiful gardens, the Ebenezer Dudley Home offers a rare opportunity to own a piece of Madison's past while enjoying the comfort and lifestyle of shoreline living today. A truly special property ideal as a full-time residence or a cherished coastal retreat.