Introducing "Topside," a truly iconic coastal retreat located at 645 South Orleans Road in Orleans. This rare offering presents a remarkable opportunity to own a piece of Cape Cod history in one of the most coveted waterfront settings. With unparalleled views of Pleasant Bay and direct access to the water, this property is the epitome of coastal living, offering charm, character, and a lifestyle that few properties can match. Designed in a manner that recalls the elegance and simplicity of a bygone era, this is the type of home that could never be built today—a unique piece of real estate destined to become a treasured legacy.
"Topside" is a thoughtfully designed and larger-than-it-appears 5-bedroom, 4.5-bathroom home with multiple spaces for entertaining, relaxing, and enjoying the Cape Cod lifestyle. The property has a distinctive nautical feel, with an upper-level deck accessible through the charming bunk room, offering a front-row seat to breathtaking views of Pleasant Bay. From this vantage point, you can take in sweeping views that stretch from the Wequassett Resort on your right, across to Eastward Ho, Chatham Yacht Club, and even the Atlantic Ocean beyond. This upper deck gives the home the ambiance of being aboard a ship, evoking the feeling of being at sea while remaining firmly rooted in this peaceful, serene setting.
Inside, the home is filled with natural light and exudes Cape Cod charm throughout, from the cozy living spaces to the spacious bedrooms. The first floor is centered around a welcoming living room, dining area, and kitchen designed for gatherings with family and friends. Upstairs, you'll find the primary suite along with additional bedrooms, all designed to make the most of the water views and tranquil surroundings. Whether you're hosting guests or simply enjoying a quiet weekend retreat, "Topside" offers flexibility and space for everyone to relax and unwind.
Step outside, and you'll discover a property designed for making the most of Cape Cod’s natural beauty. The outdoor spaces are perfect for al fresco dining, entertaining, or simply relaxing by the water’s edge. Private dock access for at least one boat, a mooring, and a staircase leading to the water offer direct access to Pleasant Bay, where boating, swimming, and water sports await. Imagine setting sail to Nauset Beach for a day on the water, or taking a short walk or boat ride to Wequassett Resort to enjoy their amenities. With views across to Chatham and beyond, this property’s waterfront position is truly special.
The outdoor area also includes several quiet nooks, perfect for reading, contemplation, or simply soaking in the serene surroundings. Whether you're enjoying a morning coffee with the sun rising over the bay or hosting an evening gathering with friends, this outdoor space is designed to capture the essence of Cape Cod living.
Importantly, the property includes private dock access, allowing you to fully embrace the Cape Cod lifestyle with boating, swimming, and waterfront recreation at your doorstep. The condo association has yet to be formed, so there is flexibility in terms of how parking, maintenance, and shared spaces might be managed in the future. This is an opportunity to shape the next chapter of this unique property’s story while preserving its charm and history.
Situated on Pleasant Bay, "Topside" enjoys an enviable location that offers both privacy and convenience. Just a few steps down the road, you'll find a small beach, perfect for those who love the sand and sea. The proximity to Wequassett Resort and Eastward Ho provides opportunities for fine dining, golf, and recreation, all just a short walk or boat ride away. With Orleans and Chatham village centers close by, you'll have easy access to shopping, dining, and all the best that Cape Cod has to offer.
Homes like "Topside" rarely come on the market. This is a property that could never be replicated today—its charm, history, and iconic location make it one of a kind. Whether you're looking for a peaceful retreat, an investment property with strong rental potential, or a place to create new memories with family and friends, "Topside" offers boundless potential. This is a home that truly captures the spirit of Cape Cod, providing a lifestyle defined by sun, sea, and serenity.
