Discover this charming 1928 Colonial in the desirable waterfront community of Shippan Point! This elegant home has been lovingly maintained by the same family for over 50 years & is now ready for new owners to infuse their own style. As you enter, you're greeted by a gracious foyer leading into a spacious Living Room, complete w/fireplace, original hardwood floors & crown moldings-ideal for entertaining & family gatherings. The formal Dining Room features beautifully detailed period corner cupboards, while the Eat-in Kitchen awaits your personal updates. The main level also includes a cozy Den with built-in bookcases and powder room. Upstairs, you'll find a generous Primary Bedroom boasting two walk-in closets and access to an ample Jack & Jill bath, easily transformable into a luxurious primary suite. This level also includes three additional bedrooms (one currently serving as an Office/Laundry Room) and hall Full Bath. The third floor features a fifth bedroom, full bath, along with a cedar closet and plenty of storage. The expansive lower level provides ample space for a gym and a recreation room. Outside, enjoy a large screened porch surrounded by mature plantings, a new two-car garage & a generator. All of this is just a short stroll from the Stamford Yacht Club and Woodway Beach Club & beach, with water access for kayaking & breathtaking sunset views. Also, you're only 7 minutes from Metro North trains & vibrant downtown Stamford. Don't miss this opportunity!