luxury seaside houses for sale Chatham, United States

Step into a timeless Cape Gambrel built by family for family as the perfect retreat for making lasting memories. Whether it's lazy beach days, cozy afternoons with a book, or rainy-day puzzles, this home captures the essence of Cape Cod living. Idea in town location just a short distance from everything in Brewster! This property includes deeded beach rights and a rare 1/100 share of the highly sought-after Sea Pines Neighborhood Association Beach--widely regarded as one of the most beautiful bay beaches in the area. The home features 4 bedrooms and an open-concept living, kitchen, and dining area with two sliders opening to outside living areas!. A full basement provides additional space and flexibility. Outdoors, enjoy multiple seating areas, a deck, firepit, and two outdoor showers--a true Cape Cod luxury. Recent updates include: New windows and rear slider Durable Azek trim and new gutters; 45-year architectural roof shingles (installed Summer 2012) Natural gas furnace, central A/C, and newer appliances. On a private, level lot, this home offers a peaceful setting with gentle scenic proximity to the shores of Cape Cod Bay. Your own sandy toes and salty kisses can start now!

Tucked away on more than 20 acres with breathtaking, panoramic views of Cape Cod Bay, this extraordinary Eastham estate presents a rare opportunity to own a true piece of Cape Cod history. Set in its own private world, this remarkable property embodies a timeless connection between heritage, nature, and coastal living. Originally constructed in 1780 and later relocated from Bridge Road, the home has a rich and storied past. For generations, it served as a beloved family retreat—a rustic hunting and fishing camp, a gathering place for simple pleasures, and a peaceful escape from the modern world. Known affectionately as “The House that Lives in Nature,” this special property continues to honor that legacy, seamlessly blending antique charm with the serenity of its stunning natural surroundings. The setting is nothing short of extraordinary. Encompassing 20.3 acres, including 16 acres preserved in conservation, the land offers unparalleled privacy and sweeping views that stretch across the bay to the distant horizon. Every moment here is shaped by the rhythm of the tides, the shifting light, and the ever-changing landscape of coastal Eastham. Whether enjoying morning coffee as the sun rises over the dunes, taking a contemplative walk along winding paths framed by mature trees, or watching vibrant sunsets melt into the water, this is a property that invites you to slow down, breathe deeply, and reconnect with nature in a way few homes can offer. The conservation land ensures that this serene environment will remain untouched, preserving both tranquility and natural beauty for generations to come. Inside, the home retains its authentic character, with period details that speak eloquently to its historic roots. The warmth of rich wood paneling, hand-hewn beams, and a central fireplace creates an atmosphere of comfort, nostalgia, and timeless craftsmanship. Each room feels intimate and inviting, offering glimpses into a bygone era when simplicity, quality, and a connection to the environment were paramount. The living room, in particular, captures the essence of this special setting, with expansive windows framing uninterrupted views of Cape Cod Bay—a living work of art that changes with the seasons, light, and tides. Every glance offers a new perspective, a new story, and a constant reminder of the extraordinary location and natural splendor surrounding the home. While steeped in history, the property also presents remarkable potential for the future. Whether preserved as a family retreat, thoughtfully restored as a historic residence, or reimagined to harmonize old and new, the possibilities are as boundless as the surrounding landscape. The land’s conservation component ensures that its privacy and beauty will endure, offering peace of mind, a sense of sanctuary, and an unparalleled connection to the Cape Cod environment. Located in one of Eastham’s most picturesque areas, this exceptional property offers seclusion while remaining conveniently close to the best of the Outer Cape. Enjoy easy access to the Cape Cod National Seashore, pristine beaches, scenic conservation trails, charming local shops, renowned restaurants, and the unique coastal culture that defines this cherished community. Whether envisioned as a year-round residence, seasonal retreat, or historic restoration project, this home offers an extraordinary opportunity to own not just a house, but a piece of Eastham’s living heritage. Truly one of a kind, this is more than a property—it is a place where history, nature, and possibility converge. From its origin as a humble seaside retreat to its role today as a treasured sanctuary, The House that Lives in Nature invites you to become part of its enduring story. With its expansive acreage, timeless character, and breathtaking panoramic water views, this Eastham estate stands as a singular offering on Cape Cod’s Bay side, ready to inspire its next chapter and captivate all who experience it.

Experience the ultimate Cape Cod summer, where every day begins with breathtaking Bay views and ends with spectacular sunsets painting the sky.This stunning 4-bedroom beachfront retreat is summer living at its absolute finest. Completely renovated in 2025, it showcases beautiful craftsmanship, panoramic vistas from every room, and top-of-the-line Viking appliances.With a proven rental history and a loyal base of returning guests, this property truly has it all, whether you're seeking a smart investment or the summer sanctuary you've always dreamed of.

Tucked between the iconic sandy paths of Mayflower and Chapin Beaches, this charming two-bedroom bungalow offers a rare chance to own in one of Cape Cod's most coveted areas. Just 350 feet to the beach, the home sits in a prime location surrounded by dunes, salty breezes, and summer magic. This is more than just a getaway, it's a canvas for your dream beach house. Architectural plans are already in place and included with the sale, allowing the future owner to transform the property into a stunning three-bedroom, two-story home. Whether you're envisioning a serene retreat or a family summer escape, this is your opportunity to reimagine coastal living at its finest.

This is a great, solid home with excellent rental history and added rental potential, offering lots of different options with a Main home and separate apartment above a free-standing garage. The home is lovingly cared for and offers lots of space - yet cozy with its beautiful wood beams and cathedral ceilings. Great oceanside location close to Duck pond, the main home features an airy, open layout with newly refinished wide pine flooring, a cathedral-ceiling living room, and a large kitchen. The layout is thoughtfully designed for privacy: a first-floor primary suite and two ensuite upstairs bedrooms connected by a signature catwalk, each with its own bathroom. Energy-efficient solar panels incredible value and versatility. Whether you're looking for a multi-generational family compound or a high-performing vacation rental, this is a great home.

Set above the Great Outer Beach and Atlantic Ocean, this unparalleled coastal home is where time stands still, and every moment is filled with awe. Enter the expansive ocean view deck and take in the vastness of the sea. Completely rebuilt in 2013, year-round jewel offers panoramic ocean views from every corner. Thoughtfully designed across three levels, each featuring a bedroom and bathroom, the main floor boasts a dining, living & kitchen area perfectly positioned to capture the waves' rhythm. Upstairs is the primary bedroom suite with a private bath and balcony, while the lower level offers relaxation with direct access to an outside shower and another set of indescribable vistas. Outside, decks and a gorgeous patio provide ideal spots for watching the most unforgettable sunrises. With private access to the beach, this property epitomizes the Cape Cod experience, offering endless seaside adventures within the pristine National Seashore. Solid rental history available. See 3D Tour & Video.