luxury seaside house for sale Old Saybrook, United States

Step into timeless New England charm with this enchanting antique home, circa 1760, ideally set in the heart of the beloved shoreline community of Westbrook. Rich in character and history, this beautifully maintained residence blends classic period details with modern comforts for effortless coastal living. Featuring five inviting fireplaces, the home offers warmth and ambiance throughout, with thoughtfully preserved architectural details that celebrate its heritage. An in-ground heated pool creates a private backyard retreat—perfect for summer gatherings, relaxation, or entertaining after a day at the shore. Enjoy an unbeatable walk-to-everything location just moments from the beach, playground, charming town center, dining and community events. The spacious two-story barn includes valuable extra storage or flexible space for hobbies, beach gear, game room or workshop use. Located in a desirable beach community, this special property also boasts a proven and successful rental history, offering excellent income potential or a seamless blend of personal use and investment opportunity. A rare opportunity to own a piece of history in a prime shoreline setting—where coastal lifestyle, character, and convenience come together beautifully.

Charming direct waterfront beach cottage in sought-after Hawk's Nest Beach, where life slows down and every day feels like a vacation. Perfect for all ages, this vibrant shoreline community offers something for everyone-swimming, sailing, kayaking, fishing, paddle boarding, and endless sand and fun. Start your mornings with beautiful sunrises over Long Island Sound and unwind in the evening with stunning sunsets over the salt marsh watching the Osprey in the nests. Set in a unique & rare road-end location, this property enjoys exceptionally low traffic, offering a peaceful, private feel that's hard to find along the shoreline. This beautiful sun-filled cottage is light, bright, and welcoming. It features a covered waterfront porch perfect for spending long lazy summer days relaxing, a main level bedroom & full bath with 3 bedrooms and another half bath up. With electric heat and a fireplace, the home stays cozy in the shoulder seasons, extending enjoyment from spring through fall. Offering approximately six months of prime use, this property also presents a fantastic investment opportunity with a strong rental history from May through October, and excellent income potential. Whether you're seeking peaceful waterfront relaxation or lively beachside gatherings, this quintessential New England waterfront retreat is your chance to become part of the cherished Hawk's Nest community-and create a lifetime of memories by the shore. Don't miss this rare coastal gem!

Nestled in the heart of picturesque Madison, this charming 2-bedroom, 1-bathroom seasonal cottage offers a serene sanctuary for enjoying summers along the shoreline. With a cozy living space, this quaint abode is perfectly designed for those seeking a peaceful beachside getaway. As you step inside, you're greeted by a warm and inviting atmosphere that captures the essence of coastal living. The open-plan living area maximizes the cottage's compact footprint, providing a comfortable space for relaxation and intimate gatherings. The kitchen is well-equipped for preparing light bites and beach picnics, while the two snug bedrooms offer a restful night's sleep after a day of fun in the sun. The loft space above the bedrooms awaits your imagination and offers an abundance of possibilities - pre-wired and ready to be finished to your heart's content! The cottage's prime location means you're just a short walk from the expansive sandy shores of Hammonasset Beach State Park. Madison's vibrant community is also at your doorstep, with its quaint downtown area, boutique shops, excellent restaurants, and attractions like the Madison Art Cinema and the historic E.C. Scranton Library. Whether you're looking for outdoor adventure or small-town charm, this cottage is the perfect seasonal home. Embrace the simplicity of cottage living and the beauty of coastal Connecticut with this delightful property, where endless summer memories await. Land lease - currently $5,400 per year.

A Shoreline Masterpiece: Custom Cape Cod Living on 1.10 Private Acres Welcome to 85 Fawn Brook Circle, an immaculate Cape Cod retreat nestled at the end of a quiet, picturesque cul-de-sac. This 4-bedroom, with a first floor primary suite; 2.5-bathroom home has been thoughtfully reimagined with a level of detail rarely seen. Rich hardwood floors flow through every room, complemented by crisp custom moldings and elegant built-in bookcases that frame the living room with timeless charm. At the heart of the home lies a gourmet kitchen, designed for both the serious chef and the frequent host. Featuring a professional-grade gas range, an expansive eat-at island, and an abundance of custom storage, it's a space where culinary dreams meet daily convenience. A finished lower level with a recreation/gym. The exterior is equally impressive, is a large Pergola just off the kitchen set on pavers for relaxation and enjoying the outdoors Set on 1.10 lush acres, the property features a standout additional detached three-car garage barn. With an upper level, this versatile space is the ultimate solution for a quiet home office, a professional workshop, or a creative studio. Just minutes from Madison's iconic beaches and vibrant downtown, this home offers the peace of the woods with the soul of the shoreline.

Coastal Living, Without the CrowdsnSet along one of East Marion's most coveted waterfront stretches, 785 The Strand offers a rare blend of privacy, natural beauty, and effortless coastal living. Experience quiet luxury with direct beach access-without the crowds. Perched above the shoreline and directly across from the Long Island Sound, this thoughtfully designed residence captures the understated elegance of the North Fork lifestyle. Surrounded by mature landscaping and sited to take full advantage of its coastal setting, the .56-acre property features a light-filled, two-story home with five bedrooms and four baths, complemented by an oversized pool, two fireplaces, and multiple outdoor spaces designed for both entertaining and relaxation. Open, airy, and filled with natural light, the home is designed to maximize comfort and connection to its surroundings, which include protected Pebble Beach-communally-owned no development lots to the east and south. Expansive windows frame the landscape, while clean architectural lines and warm finishes create a refined yet relaxed atmosphere. Here, beach access is part of everyday life, not an occasion. Also ideally located near marinas, farm stands, wineries, golf courses, and a short drive to Greenport Village. This is a rare opportunity to own in one of the North Fork's most desirable and tightly held locations.

Set along one of East Marion's most coveted waterfront stretches, 785 The Strand offers a rare blend of privacy, natural beauty, and effortless coastal living. Experience quiet luxury with direct beach access-without the crowds. Perched above the shoreline and directly across from the Long Island Sound, this thoughtfully designed residence captures the understated elegance of the North Fork lifestyle. Surrounded by mature landscaping and sited to take full advantage of its coastal setting, the .56-acre property features a light-filled, two-story home with five bedrooms and four baths, complemented by an oversized pool, two fireplaces, and multiple outdoor spaces designed for both entertaining and relaxation. Open, airy, and filled with natural light, the home is designed to maximize comfort and connection to its surroundings, which include protected Pebble Beach-communally-owned no development lots to the east and south. Expansive windows frame the landscape, while clean architectural lines and warm finishes create a refined yet relaxed atmosphere. Here, beach access is part of everyday life, not an occasion. Also ideally located near marinas, farm stands, wineries, golf courses, and a short drive to Greenport Village. This is a rare opportunity to own in one of the North Fork's most desirable and tightly held locations.

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.

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.

Welcome to this delightful 2-bedroom, 1-bath condo offering the perfect blend of comfort and convenience! Located just minutes from Ocean Beach Park, this move-in-ready home features a freshly updated kitchen with new appliances, ready for your culinary adventures. Enjoy easy living in this low maintenance condo.

It’s All About the Location! Perfectly situated along the Long Island Sound in the coveted hamlet of Southold. This quintessential North Fork beach cottage captures the very essence of coastal living, offering 100 feet of prime, sandy beachfront—a rare and exceptional find. While intimate in scale, the property delivers a lifestyle that’s nothing short of extraordinary. Spend your days seaside, basking in the sun amid Mediterranean-like surroundings, and your evenings savoring a cocktail as the sky transforms into a canvas of breathtaking sunsets. Set on .8 of an acre, this property presents a unique opportunity—enjoy it in its current charming form or plan and build your custom waterfront dream home. Either way, this offering embodies the timeless appeal of beach front living at its finest.