luxury waterfront houses for sale Old Saybrook, United States

Essex Village waterfront enjoys one-level living and truly incredible sunrise colors and direct views of spectacular sunsets over water creating reflective and ever-changing scenery. This three bedroom, modern home is nestled between Middle Cove and the Connecticut River with 190ft of direct waterfront and a completely private outdoor setting you will covet. Set on 3/4 of an acre this home comes with its own bulkhead with dockage for fast boat trips from the river to Long Island Sound and beyond. The stone patio stretches the entire length of the house and will quickly become your favorite spot. The handsome, newly renovated kitchen has extensive built-in cabinets, polished quartz countertops and is open to the family room with a fireplace and cozy dining area. The living room also has a fireplace and a wall of windows with glass sliders affording waterviews from indoors. The primary suite is seperate from the guest rooms for privacy and has a fabulous, newly remodeled bath, tiled walk-in shower, Rhol polished nickel fixtures, custom cabinets, Carrara marble dual-sink counter and soaking tub. There is a barn for all your outdoor and nautical storage needs and a finished shed that acts as a heated studio. This Village home is a quick stroll to all yacht clubs, marinas, the famed Griswold Inn, the Connecticut River Museum, restaurants, and shopping. Resort-style living, all on one level and ready to enjoy as your own year round, in one of New England's most idyllic settings.

Set in a magnificent North Cove waterfront location, this exquisitely designed and masterfully crafted residence captures striking views of the Connecticut River and Long Island Sound, all just moments from the Village of Essex. Built in 2014 with exceptional attention to detail, the nearly 6,000-square-foot home offers a timeless architectural aesthetic, beautifully balanced living spaces, and expansive walls of windows and French doors that frame the inspiring water views. Spacious stone terraces extend the living areas outdoors, while professionally landscaped grounds feature mature gardens, specimen plantings, and graceful shade trees. Inside, custom moldings, wood, tile, and marble flooring, along with a state-of-the-art hydro-air heating and cooling system, reflect the home's quality and thoughtful design. A separate finished bonus room with its own staircase offers exceptional flexibility as an au pair suite, private studio, or home office, while a three-bay garage provides ample space and convenience. The spectacular waterfront grounds are designed for both entertaining and relaxation, featuring expansive bluestone terraces, an outdoor gas fire pit, and a stunning pool and spa complex, all set against the breathtaking backdrop of North Cove and the Connecticut River. Completing this exceptional offering is a shared dock with a slip accommodating a boat up to 25 feet, making this a truly distinctive waterfront retreat.

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!

Set on 2.1 private acres directly along Hamburg Cove, WATERLOT offers an extraordinary opportunity to acquire a premier waterfront estate on one of New England's most cherished maritime retreats. Renowned among boating enthusiasts as one of the region's finest and most secure "hurricane holes," Hamburg Cove provides a beautiful backdrop to this home. The property boasts over 220 feet of direct water frontage and potential for dockage capable of accommodating vessels up to 80 feet - a true unicorn for the region, where private residential slips of this scale and depth are virtually non-existent. Built with exceptional craftsmanship, the home offers a timeless foundation for its next chapter. While impeccably maintained and completely functional to enjoy as-is, the interiors await your bespoke design vision, offering an ideal canvas to craft a world-class waterfront haven.

RARE OPPORTUNITY in the highly sought-after Barberry Farms Association! With only 2 MLS sales since 2021, homes in this premier beach community seldom become available. Enjoy private access to a wonderfully wide & deep sandy beach that has storage bins & an area for kayaks & small sailboats to make life easier. BIG home, BIG rooms. Spanning 4,833 sq ft, this 10 room Colonial features hardwood floors throughout. Off the formal entry foyer sits a den/library w/ built-ins, ideal for a home office, & a formal living room centered by a wood-burning fireplace. The main level also boasts a formal dining room w/ a bow window, & a center island chef's kitchen w/ granite counters, double ovens & a real walk-in pantry. Adjacent to the kitchen, a natural light filled family room offers a gas fireplace, a bow window & sliders out to a broad bluestone patio for outdoor entertaining. Upstairs features cathedral ceilings, a vaulted game room, a large laundry room w/ utility sink that is super convenient, & 4 bedrooms, 3 w/ walk-in closets. Highlights include 2 ensuites! The primary retreat has a spacious bathroom with deluxe spa tub, oversized glass shower, long double vanity, even an English heated towel rack. Set on professionally landscaped grounds, the flat open backyard is ready for lawn games or a future pool. Features include 4 full/2 half baths, a full basement, 8-zone (!) natural gas heat, city water & a 3 car garage. Exceptional coastal living. Don't wait another 5 years!

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see.

Rare opportunity to own a uniquely private 7.49-acre bay front estate in Orient Village. This exceptional waterfront property features a spacious 5700 sq ft main residence with 6 bedrooms, 7 baths, three wood burning fireplaces, three bay garage, expansive front and rear covered porches and panoramic bay views. The 20 x 44 heated pool is complemented with a 860 sq ft pool house featuring open common area, kitchenette, full bath, laundry, two changing rooms, outdoor shower, & porch – creating an ideal setting for entertaining and summer living. A fully fenced clay 60 x 120 ft tennis court is expertly sited, so sun glare is never an issue. The property offers an additional free-standing two-bay garage with second floor bonus space providing flexible options for recreation, boat/bike storage or studio space. The 195 ft wide private walkout bay beach offers sweeping Harbor views of Long Beach State Park, Bug Light House and Orient Yacht Club. The property is ideally located within walking or biking distance to the Village of Orient, Orient Yacht Club, local marinas, Post Office, the Country Store, Oysterponds Historical Society and all village amenities.

Perched over the CT River on one of the largest lots on Main, the David Watrous House offers water views from each room. This 1850 architectural treasure offers over 4,000 square feet of living space, plus an additional 1,500+ square foot walkout lower level. A detached oversized 3-bay post-and-beam carriage house offers exceptional workshop/studio space, stained glass windows and crowned by a copper cupola with antique weathervane. A side porch entry leads to chef's kitchen with handcrafted Vermont solid cherry cabinetry, granite countertops, stainless appliances, a tin ceiling and dramatic 10-foot island. Formal dining with antique chandelier and fireplace make for elevated home entertaining. The dramatic riverfront great room with wall-to-wall windows, a river-facing 2nd kitchen, fireplace, and expansive deck captures ever-changing water views. A den, living room, office with cherry built-ins, 10+ foot ceilings and full bath offer flexibility on 1st flr. Upstairs, restored original chestnut floors lead to multiple living spaces, full laundry, a 3rd kitchen and a primary suite with gas fireplace with marble en suite. Recent upgrades include new windows, patio, driveway, refreshed landscaping, Buderus furnace, upgraded 400-amp electrical, restored chimneys, whole-house generator, and updated roofing. Stone pathways lead to private riverside seating areas for amazing sunsets. Rare chance to claim a home of notable architectural significance with recognized press coverage.

BEACH HOME! BEACH RIGHTS! NEEDS WORK! It is not everyday that an opportunity to own a double lot in such a shoreline area. This charming English Cottage-style Cape, situated on a generous footprint for the area, is ready for it's next chapter-whether that involves a thoughtful renovation or the construction of a brand-new coastal home perhaps. Residents enjoy deeded rights to a private association sandy beach located just at the end of the street! The main residence of which there are no photos for obvious reasons once you see it (NEEDS WORK) currently features three bedrooms and 1.5 baths but adding to the property's versatility is a delightful in good condition accessory apartment, which offers a full kitchen, full bath, a private bedroom and a cozy living area anchored by a stone fireplace and two separate exterior entrances. This setup is ideal for multi-generational living, a great guest suite or potential rental income. Maybe live in this while redoing the other portion. The property is a double lot that accommodates four dedicated parking spaces - a true luxury for beachside living. Best of all, the property is located where no flood insurance is required, offering peace of mind alongside the salt air. Whether you choose to polish this unique gem or start fresh with a custom build, this is the perfect canvas for your seaside lifestyle.

Discover the perfect opportunity to build your dream home on this beautiful 1.67-acre waterview lot in the heart of Greenport. Just five blocks from Greenport Village, you’ll have easy access to charming boutiques, renowned restaurants, lively bars, and more—all while enjoying the tranquility of your own private retreat. This property includes deeded bay beach rights at the end of 9th Street, where you can , take a refreshing swim, or set off on a peaceful kayak adventure around Pipes Cove. Please note: Showings are by appointment only. No one is permitted to walk the grounds without an agent present. Don’t miss this rare chance to own a prime piece of North Fork paradise! No one is permitted to walk the property without an appointment and must sign a Hold Harmless.

This is a Once in a Lifetime Opportunity. Some properties can be reproduced, this one cannot. Built in 1914 by industrialist Samuel Hird and later lovingly stewarded by cosmetics magnate Bob Ruttenberg, this extraordinary Shelter Island Estate is a surviving expression of a more gracious era when great waterfront homes were created with scale, permanence and a sense of place rarely possible today. Set on 1.6 acres with approximately 245 feet of waterfront with a private deep water dock, the approximately 4,500-square-foot residence commands sweeping western views across Dering Harbor. Mature grounds, covered porches and a heated gunite pool with spa create the privacy and romance of a true country estate. The property provides ultimate privacy, a secluded oasis sheltered from the world outside. A three-car garage and pool cabana with changing rooms, both retaining historic details, further enhance the property, with the garage and cabana offering the opportunity to be thoughtfully refreshed or reimagined. Inside the home, beautifully proportioned rooms unfold toward the water. Expansive windows, French doors and multiple wood burning fireplaces give the house warmth and character, while gracious living and dining rooms, an inviting kitchen with butler's pantry, intimate den and generous bedroom accommodations make the home equally suited to relaxed living and elegant entertaining. The primary suite is a private retreat with its own sitting room or office, fireplace and ensuite bath. Upper-level guest rooms capture elevated harbor views, allowing the water to remain a constant presence throughout the house. The opportunity extends well beyond the waterfront estate itself. The residence, waterfront grounds, garage, pool and private dock are now offered at $15,995,000, together with a right of first refusal to purchase 3.2+ additional buildable acres. For those who envision a larger compound, the additional acreage may be acquired with the estate for a total offering of $17,995,000, creating the rare possibility for a substantial guest residence, tennis, or expanded gardens and recreation. Few waterfront properties offer the opportunity to acquire an estate of this character today while also preserving the ability to substantially expand its scale for the future. This is more than waterfront real estate, it is an opportunity to live with the grandeur and graciousness of the Gilded Age, with the comforts of modern life. Proudly presenting 6 Harbor Lane, what is a century in the making, impossible to recreate, and a once-in-a-lifetime opportunity to become its next steward.

This 2024 constructed 5,800-square-foot modern waterfront residence, built by Fountainhead Construction Inc., offers 250 feet of sandy beach and extraordinary panoramic water views. 180 degrees of sweeping water views from Crab Creek to North Haven Point and across Great Peconic Bay, with 250 feet of sandy beach along the shoreline. Walls of glass in the kitchen, dining area, living room, and select bedrooms frame the remarkable water views and glowing sunsets, creating a seamless connection between indoors and out. Step onto the waterfront patio or terrace to experience the setting even more fully. The sleek five-bedroom home includes six full baths and two half baths, with sophisticated finishes and amenities throughout, including 10-foot doors, a kitchen with custom Italian cabinetry and natural stone countertops, a fireplace, media room, and heated waterside pool. Set on 2.12 secluded acres, this exceptional property offers a rare opportunity for refined waterfront living

A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.

17 Brander Parkway, Shelter Island, NY 11964

Rare opportunity to own this stunning 13.85 acres bay front parcel with over 450ft of secluded beach. This property boasts a depth of over 1000ft, creating a huge blank canvas to design your dream legacy estate. Offering scenic trails, serene ponds, and glorious sunrises. The perfect place to build your dream home and weave your everlasting story.

Waterfront.. Sachems Head - Welcome to a Unique opportunity to purchase some of the finest waterfront properties to ever become available on the entire Connecticut Shoreline. Combined 3 properties span 13.03 rolling green Acres w/1900 feet of waterfront, 3 Docks, Boat Lift, Vineyard, Orchards, Beautiful Gardens, Fruit Trees, Tennis/Basketball Court, Go Kart Track, 2 Houses and a Carriage House. The Main House, a testament to exceptional craftsmanship, showcases approximately 5,534 square feet of living space, with six well-appointed bedrooms and 4.1 bathrooms. Designed with the finest materials, this home seamlessly blends timeless elegance and modern conveniences, providing a harmonious living environment. Outdoor area includes a Pool, Spa & Outdoor kitchen. Guest House with 3,583 sq feet, 3 bedrooms, 3 baths, Separate 942 sq ft. 1 bedroom in-law/ staff quarters. This property shares a Common border with the main residence. The separated property which can possibly be subdivided into 2 building sites, features a Carriage House, Dock & Sandy Beach. To say there are many possibilities here would be an enormous understatement! Private residence, Family compound or High-end development. Bring your Dream here; this opportunity will not let you down. All 3 properties must be sold together unless otherwise agreed to by the current owners. Please respect the privacy of current owners. BY APPOINTMENT ONLY. Taxes represent all 3 properties.

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.

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.

This is a one of a kind fully reimagined, architectural masterpiece on Shelter Island, NY, boasting a flawless 2022 full-gut contemporary renovation by a serial tastemaker with an elite portfolio spanning NYC, California, and Hawaii. Located in the coveted Shorewood area, this premier estate offers a lifestyle of pure perfection and absolute privacy. Passing through the gated driveway, you instantly realize you are about to have an elevated experience. Indoor-outdoor living reveals breathtaking views at every turn, where the vast southwestern sky offers beautiful sunsets and truly magical light. Multiple designated spots allow you to dine alfresco while taking in the landscape. The interior spaces flow onto enchanted gardens, lawns, a private sandy beach, and a spectacular waterside pool, crowned by a roof deck with jaw-dropping panoramic views-leaving one to ask, why would you ever leave? Yet, when you do, a dinner excursion to Sag Harbor is entirely effortless, whether you choose to take a quick drive to the South Ferry or launch a boat trip straight off your own private dock.

Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the relaxed waterfront lifestyle. Designed for both entertaining and everyday enjoyment, the property features two private docks ideal for boating, paddleboarding, and kayaking, along with a spacious waterside deck overlooking the sparkling water. The first floor has a large waterfront room that opens directly onto the deck, complemented by 4 generously sized bedrooms and 4 full bathrooms. Upstairs, soaring cathedral ceilings frame an open-concept great room encompassing the living, dining, and kitchen areas. Walls of glass capture stunning panoramic water views, creating a light-filled and inviting gathering space. Privately situated off the great room, the expansive primary suite offers a large walk-in closet and a spa-inspired bathroom. Completing the property is a detached 2-car garage with a finished upper level, providing the perfect space for recreation, a home office, artist’s studio, or additional guest accommodations. A rare opportunity to enjoy waterfront living with private docks, beach access, tennis, and some of Shelter Island’s most captivating water views.

Waterfront Living on the North Fork- Wake up to breathtaking views of the Peconic Bay, where sunlight dances across the water, birds soar above the neighboring nature preserve, and a tranquil deep-water inlet stretches beyond your deck. This charming beach cottage offers a rare opportunity to experience the very best of North Fork waterfront living. Featuring 3 bedrooms and 2 baths, the home offers a comfortable, open-concept layout connecting the waterside living room, dining room, kitchen, and entertainment areas—perfect for relaxed summer mornings, afternoon gatherings, and memorable evenings with family and friends. Step outside onto the spacious wraparound deck and take in 120 feet of pristine waterfront. Spend your days swimming, kayaking, sunbathing, or simply enjoying the ever-changing beauty of the bay. The property is extremely private and peaceful, yet just steps from the private sandy association beach. A rare and special waterfront retreat, this quintessential cottage captures the effortless beauty of North Fork living—a place where every day feels like summer.

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.

An extraordinary offering on the Peconic Bay, this refined Cedar Beach waterfront estate presents over 200 feet of direct, sun drenched, south facing shoreline and beach with a protected, private dock deep enough for a mid twenty ft boat, a truly rare combination of attributes to find on the North Fork. Thoughtfully designed to embrace its breathtaking setting, the house is set on a double lot whose southern exposure also produces the luxuries of southerly breezes and a true, useable and enjoyable beach not encumbered by prolific rocks or muck. The home itself is defined by soaring cathedral ceilings, sun-drenched interiors, and elegant entertaining spaces that seamlessly transition to expansive waterside terraces overlooking endless bay views and spectacular sunsets. Private ensuite accommodations and beautifully curated living spaces evoke a sense of understated coastal sophistication. Complementing the property, a separate waterfront parcel directly across the street features a newly refurbished private dock with direct bay access, offering an exceptional opportunity for boating, fishing, quick trips to Shelter Island, Sag Harbor, the Hamptons and other beautiful East End destinations. A exceptional and rare North Fork lifestyle centered around the beach, sun and water.