luxury seaside houses for sale Old Saybrook, United States

Enjoy exclusive Beach Rights and ultimate coastal living in the highly desirable Chapman Beach community! Just steps from the sand, this bright and airy 3-bedroom, 1-bath seasonal cottage is the ultimate shoreline escape you've been waiting for. Inside, 828 square feet of sun-drenched living space is perfectly optimized for relaxed, carefree seaside vibes. Tucked away on a private lot along a quiet road, your outdoor oasis features a generous deck ready for summer BBQs, an expansive yard for lawn games, and a dedicated shed to stow your surfboards and beach gear. Ready for your personal touch! Just moments from the Connecticut Shoreline's finest dining, marinas, and boutique shopping, this rare gem is the timeless summer escape you've been waiting for.

A rare combination of privacy, functionality, and sweeping water views distinguishes this exceptional year-round shoreline estate, ideally situated in one of Westbrook's most desirable coastal enclaves. Positioned on the quiet, exclusive end of Seaside Avenue just steps from a pristine private beach, the residence is set upon a rare double lot that offers an uncommon sense of openness, tranquility, and room to grow. Thoughtfully designed for effortless coastal living and grand-scale entertaining, the home is bathed in natural light and frames spectacular vistas of Long Island Sound from multiple viewing decks. The heart of the home features a bright, open-concept main level that seamlessly connects the living, dining, and kitchen areas. This floor hosts two bedrooms, including a convenient additional ensuite-perfect for guests, an office, or multi-generational living. The primary suite privately perched on the third floor has it's own living area and a deck for morning coffee or sievening sunsets. The thoughtfully finished lower level serves as a seamless indoor-outdoor transition, complete with a kitchenette and full bath for effortless post-beach gatherings.

Welcome to your ultimate seaside retreat at 3 Mohican Road, nestled in the highly sought-after Grove Beach Terrace neighborhood of Westbrook. This charming 3-bedroom, 2-bathroom home offers the quintessential coastal lifestyle, featuring a direct right-of-way path from your own backyard straight to the sandy shores of Long Island Sound.The main level welcomes you with a bright, open-concept layout where the kitchen, living, and dining rooms create the perfect central hub for entertaining and daily living. In the kitchen, a gas fueled Viking Stove and high end appliances complement the granite countertops, which feature a center island with an additional sink. Just off the dining area is a sun-drenched main-floor sunroom, featuring sliding glass doors that open directly onto the back deck. Additional features include a large pantry and a convenient laundry room with extra storage along with a first-floor full bath.Upstairs, the second level hosts all three bedrooms. The primary suite is a true sanctuary, complete with a spacious walk-in closet and its own private sunroom offering stunning, elevated water views.The outdoor amenities perfectly complement the interior. After a day in the sand, rinse off in the refreshing outdoor shower. When you're ready to unwind, choose between the expansive back deck or the additional side deck, which provides a perfect, shaded oasis for cool summer evenings. Don't miss this rare opportunity to live the beach life you've always dreamed of!

Set along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach non-buildable parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

Rare 1.07-Acre Coastal Compound on The StrandnSet along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach non-buildable parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

Some properties are simply irreplaceable. This is one of them. Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island Shingle beach house sits on a level acre along one of the Island's most coveted stretches of waterfront - 190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour. Deceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. Two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Mature landscaping on all sides for privacy. The expansive side lawn - often mistaken for a separate lot - offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow. A chance to own a piece of Shelter Island's story.

Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island shingled beach house sits on a level acre along one of the Island's most coveted stretches of waterfront -190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour. Deceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Maturenlandscaping on all sides for privacy. The expansive side lawn is often mistaken for a separate lot and offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow.nA chance to own a piece of Shelter Island's story.